'"I deliberately understaff every project" | Leadership lessons from Rippling''s $16B journey'

Matt MacInnisIt is really important to me that we feel that we've deliberately understaffed every project at the company. If you overstaff, you get politics, you get people working on things that are further down the priority list than necessary. That is poison. It's wasteful. It slows you down. It creates cruft.

Lenny RachitskyYou've been a long time COO at Rippling. Recently, you moved into CPO, Chief Product Officer at Rippling. Something you talk a lot about is that extraordinary results require extraordinary efforts.

Matt MacInnisIf you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. You got to sort of remind people that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. It's supposed to be really fricking exhausting.

Lenny RachitskyYou're a big fan of escalating issues.

Matt MacInnisFundamentally, the most selfish thing you can do is withhold feedback from someone. When you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable. Well, you're optimizing for your own comfort, and it's fundamentally selfish. So many people have teams that are not functioning incredibly well. Teams will always optimize for local comfort over company outcomes. The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity. That is fucking dangerous.

As an executive, as a leader, your job is to preserve that intensity at its highest possible level. You've had a couple really interesting experiences with your own startup. We talk in Silicon Valley about never quit, but that is complete absolute venture capital.

Lenny RachitskyToday, my guest is Matt MacInnis, Chief Product Officer and formerly longtime Chief Operating Officer at Rippling. If you don't know much about Rippling, it's a massively successful business last valued at over $16 billion. They have over 5,000 employees, and Matt has been instrumental to that success. He's also got a really rare combination of brutal honesty, a ton of experience building a very complex and very successful business, and being able to clearly articulate what he has learned really well. Matt shared a lot of insights and advice that I've not heard anyone else on this podcast share, and I left this conversation feeling that every leader needs to hear his advice.

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Matt, thank you so much for being here and welcome to the podcast. Thank you for having me. I want to start with something that I know is really important to you, something you talk a lot about that I don't think people hear enough on podcasts like this, which is that extraordinary results require extraordinary efforts. Talk about why this is so important, what you think people need to hear.

Matt MacInnisThis is a term, that phrasing I actually attribute to a friend of mine, Dan Gill, who's the chief product officer at Carvana, which as a company also doesn't get enough credit for how much of a tech company it actually is. Super interesting. And I think as a general framework for me, and a lot of what I say with you today is not really specific to product in any way. We should actually talk about that. It's like the product function is an instantiation of the general concept of management. Being a chief product officer is not that different from being a chief whatever officer. You have to apply the same frameworks and concepts to get people to achieve goals together. But one thing that is absolutely universal that I think we, honestly, I think we forget it in Silicon Valley or a lot of people don't sort of internalize it, is that if you want to accomplish something truly extraordinary, if you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult.

It's going to be really uncomfortable. And you got to sort of remind people of that, that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. They have definitely screwed up somehow. It's not that an extraordinary effort is sufficient to an extraordinary outcome, but it is 100% true that it is necessary. And so I do use that framework as a sort of guiding principle in my own leadership.

Lenny RachitskyTo make this even more real for people, what are examples of moments that were extraordinarily hard?

Matt MacInnisIt is not about any sort of grand single story. I think the story is actually told through a thousand little things. And so for me, the story is told through a thousand Jira tickets, not through a thousand grand events. The extraordinary effort thing is a reminder that it's supposed to be really fricking exhausting. It's supposed to be. So on Friday night, when you get hit with an escalation on Friday night, when you get sort of hit with a bunch of new bugs from someone in the engineering team that you've got a triage, those are the moments where great players and great teams are separated from good players and good teams. And it's so easy to say this at a company like Rippling because we're winning. As a company, for all of our foibles, and we should spend time today talking about where things are not perfect and not great, but the growth rate of the company on the revenue foundation that we have is extraordinary, really, really compelling.

And it gives you, as a leader, the air cover to get up in front of your team and say, "Hey guys, I need the last ounce of oil that you've got left." And if your company's not growing very quickly, if things aren't that great, if your growth rate is 30% or 40%, it doesn't feel as good as a contributor in that business to lean in and give everything you've got on Friday or Saturday or Sunday because you don't know that it's going to yield much. And so extraordinary results, outcomes demand extraordinary efforts, but if there's no chance at an extraordinary outcome, it's very hard to get the extraordinary effort. And so I like to remind people at Rippling at least that it's so rare to have the opportunity to be able to be a part of a team where the extraordinary effort that you do put in on Friday or whatever, whenever it is actually contributing to an extraordinary result.
It's a very special and rare thing, and it gives me a superpower as a leader because I can lean on that when I'm ringing the oil out of somebody who's in the bored and tired zone.

Lenny RachitskyI saw the same thing actually at Airbnb with Brian Chesky. It always felt like things were going great and maybe we could take a break after something we shipped was killing it. And it always felt like the opposite. It always felt like, how do we press the gas pedal further? How do we go faster? How do we go bigger? There's never a moment to take a break.

Matt MacInnisI spent seven years at Apple and learned under Steve Jobs when he was the CEO, learned what we called the death march, which is what we did to the engineers. It was like as soon as you shipped one version of the iPhone, you were just immediately thrown into the pit of building the next one and there was no break. It was just relentless and talk about an extraordinary outcome at the end of the day. There is no relief. In a competitive market, and if the market is valuable, it's competitive, no question. If you leave anything on the field, if you sort of leave a crack for your competitor, 100% chance they're going to go fill that crack. And so you have to be relentless. There can be no relaxation of the organization. It doesn't mean people can't come and go or people can't take vacations or live their lives, of course.

And it's not like people are human beings. You can't grind the individuals down, but the team as a collective group of people has to be sort of on the ball all the time. There can't be a break. And if you leave one, you're just begging for the slightly more hungry competitor to come in and eat your lunch. And that's the beauty of capitalism.

Lenny RachitskyAlso, very counterintuitively, and maybe the more optimistic perspective here is when you do give your team space to just twiddle their thumbs, bad things start to happen. Morale actually dips in my experience. People get distracted. They're like, "Oh, what are we even doing? It's not interesting." I find that keeping people busy and motivated and fired up, even though you may think they'll be happier taking a many week break and slowing things down, I find they get more, the more I actually goes down in those moments.

Matt MacInnisSo here's a management framework that I use fairly often. As an executive, you don't know how to get any decision exactly right. It's not knowable. You don't know how much budget to allocate. You don't know how many people to put on a project. You don't know how to set a deadline for when you're going to ship something. But of course, you have to set some default so you make your best guess and then you manage to that best guess and you learn as you go because in software development and in business in general, everything's emergent. These are not things that are knowable top down or a priority. And so you take a best guess and knowing that you're not going to get the right answer, you need to decide whether over-steering or under-steering relative to your perceived midpoint is better. And so let's talk about staffing. When you staff a project, is it better to overstaff or is it better to under-staff knowing that you can't get it right? Well, it's better to under-staff. If you overstaff, you get everything that you just said. You get politics, you get people working, I think most importantly on things that are further down the priority list than necessary. You have like 20 things on a stack rank list and you know that you got to do the top five, but the next 15 data's kind of ambiguous, but you've overstaffed the project. So the next 10 things down are getting worked on. Before you even know if they're necessary, that is poison. It's wasteful, it slows you down, it creates crust. And so it's very clear that under-staffing is less evil than over-staffing. In this particular framework, the advice is under-staff deliberately, always. And then the wisdom, the wisdom element is to know not to under-under-staff and sort of knowing the difference between those two things.

And so that's the way we work at Rippling. Everyone is constantly asking for more resources and of course where we can afford to and where it's appropriate new resources arrive, but it is really important to me that we feel that we've deliberately understaffed every project at the company.

Lenny RachitskyThere's a previous guest, I forget who this was. They used this metaphor if they want their team to be dehydrated to always be wanting more water. And then eventually they're too dehydrated and okay, we needed someone to help. Interesting. Yeah. There's a line along the lines of extraordinary efforts I want to make sure I read because I think this is really good. This may be a way to summarize what you're saying, that good teams get tired and that's when great teams kick the good team's asses.

Matt MacInnisYes. This was a quote actually from Sunil, and he found it from a women's basketball team coach. And it is, to my point earlier about you got to run the engine at the red line at all times because the minute you let your guard down, the minute you slow down, the minute you relax, the minute you leave a crack for your competition, the great teams are going to come in and kick the good team's. And it's like sports, I'm not a very sporty guy, but sports analogies are sort of irresistible because at the end of the day, business is a game and none of this matters. We're not going to carry it to the grave. It's like you're here to do this stuff because it somehow fulfills you while you're on the planet. And I love the sport of business and I find that sports, notwithstanding the fact that I watched very little of it, that military, those are very ripe sources of parallel concepts to apply in leadership.

Lenny RachitskyI find also those most intense, stressful, long nights are the moments you remember most and remember most fondly back to when you're building something. The key though is that it has to go well. As you said, if you are succeeding and winning, all of this is romantic in the end and nostalgic. Remember that time we built this thing and worked late nights and shipped this thing? If it doesn't go anywhere, you don't feel that. So I think that's a really important component of this is you need to be winning and succeeding.

Matt MacInnisOne thing that I've learned from Parker, Parker's our CEO at Rippling, he said, "You don't really learn from your mistakes, you learn from your successes." And it's like you do, of course, and he would admit you learn a bit from mistakes, but I do think that this is sort of feel good that it's like, "Well, you didn't succeed, but at least you learned something." I've had failures. When I look back at the nine years I spent working on inkling from day one in 2009 until we sold that business to a private equity firm in 2018, up the curve of Silicon Valley coolness, back down the other side into obscurity. Of course, I learned and grew a ton during that time, but in now what I think is six or seven years, I'm trying to do the math, seven years coming up on at Rippling, I've learned so much more because I've seen success.

I've seen rapid, wild, crazy off the charts success of the business and it's more informative. There's more to glean from seeing how it's done right than there is to glean from seeing how it's done wrong. If I tell you you're going to get on an airplane and one maintenance technician has seen it done right a hundred times and the other maintenance technician has seen it done wrong a hundred times, but he learned from his mistakes, but still hasn't had any success himself. I mean, give me a break. There's not even a comparison which plane you're going to feel more comfortable on. And so I do think that learning from your mistakes thing is a bit of a feel good trope that actually has very little substance in reality. And it's why as an early career product manager, or it's why frankly at any stage of your career when you want to learn, you should join a winning team.
It's cool to go and start a company at 22. Good luck to you. The odds are not in your favor, but the folks who, when I look at a resume and I see that someone's joined, they were at really good companies when those companies were super exciting and in crazy growth mode. I'm like, "I instantly want to interview that candidate because I want to hear what they learned from being part of a winning team." And that's sort of one of my go to heuristics when I'm looking at candidate profiles and I think it's an under-told trope. Sorry, not an under-told trope. It's a piece of advice that I don't think people embrace enough in the valley that success begets success and you should chase success.

Lenny RachitskySpeaking of success and learning, you've been a long time COO at Rippling and the reason you're here recently you moved into CPO, chief product officer at Rippling, which is very exciting and very rare. I don't see a lot of COOs moving into product. Let me ask you why did you move into that role? I feel like you've been killing it at COO. Maybe that's the reason. Be careful what you're good at. And also just what are some surprises about this, about moving into product? Because a lot of people imagine what it's like and then you're actually doing it.

Matt MacInnisThe story at Rippling is pretty interesting and I'll tell it because I think it explains why I'm making this transition, but this isn't really about me. I think it's sort of a pattern that your listeners would find useful. In general, your best executives are the ones that you can mostly toss into any challenge and they will bring order to chaos. They will fix the thing. And I do appreciate the terms that people have used at Rippling for me, talking about MacInnis's injured birds, where at any given moment some function is in disarray or in jeopardy and I go and focus very carefully on that function to get it back in order batting 800 maybe, like not always wild success, but I did that everywhere except R&D. I would think about helping out with components of the sales organization like our channel team, or I spent time building out the recruiting function a few times when it needed to be sort of rethought in response to our growth, but it never R&D.

And so I would have my feet up on the table looking out across the floor at this dumpster fire off in the distance, just sort of emitting smoke and wondering if someone was going to go in and deal with that. And the smoke takes various forms and when you're growing as quickly as rippling is growing, it's not always something that necessarily even impacts customers, but it's the sort of thing where you're like, that architecture's not right or they're not measuring adoption correctly." From the outside, I actually had quite a few criticisms that I could lob in. And what happened at Rippling was we made some hiring mistakes. I think the folks that we had in those roles would agree that they weren't the right people. We had a hiring mistake in engineering leadership where the product leader at the time had to sort of run engineering.
We subsequently had a mistake in product hiring and a lot of us had to sort of pitch in. And Parker and I sort of stared at each other through two years of this kind of disarray or this chaos or this agony of things and just never really having good executive leadership over both engineering and product at the same time. And I remember Parker sort of slumped down in his seat and said, "Oh, I have to run another search." And I said, "No, the gig's up. I'm going to go do it." And he really sprung up in his seat. He's like, "Really? You'll go do that?" I'm like, "Dude, this is what the business needs." And so that's what I did. And that really started about a year ago in sort of, I realized I was going to do it and expressed that to Parker in December. I really took it on in January of '25.
And so it's been 11 months of learning. Jumping into the product role when the product function itself, although staffed with really talented people, wildly under understaffed, and without a single spiritual leader on top of it to drive consistency and process excellence had become locally optimized but globally incoherent. And if you know Conway's law, you are destined to ship your org chart. And so with a locally optimized, globally incoherent team, you had a locally optimized, globally incoherent product experience that needed to be resolved. And so my efforts over the last 11 months have been to establish greater clarity in terms of how we do things around here, better process, better general leadership, hiring and firing. I mean, just doing the sort of cleanup on aisle three that needed to be done, even though, again, a lot of the people in the team were quite talented and doing an excellent job of managing their specific domains.
Jumping into the product role has been quite eye-opening. I feel a little bashful about the naivety of my view from the outside a year ago. Product teams have a hierarchy of needs, and we like to point at the failures to meet elements of that hierarchy higher up the triangle and sort of impugn the failure of that organization for not, as an example, measuring adoption metrics very carefully and not closely tracking those metrics as a means by which to drive execution. When I jumped in, I was like, "Man, we need to establish some basic standards for test coverage. We need to establish some basic standards for how we do what I call a factory inspection on a product once it's ready to roll off the assembly line." Do we have a checklist for what we call product quality and what does product quality mean? Those basic things weren't there. And so the idea that we should be spending time measuring adoption metrics is absolute insanity.
You're skipping a lot of steps between here and there. And so we have made great strides and I think it's translating to product quality improvements for our customers, but I feel, as I said, a little dumb for the way I was thinking about it before I jumped into the deep end. There is just no excuse as an executive for sitting outside of the mess and thinking you know the answers. It's a cardinal sin as an executive to do that. You need to go and see. You'd be in the boiler room, you need to study the system, bottom up and develop hypotheses for how to amend the system. And that's what I've been doing.

Lenny RachitskyI love hearing this because so many people have teams that are not functioning incredibly well and hearing from someone that is not a longtime product person come in and try to fix these problems, I think is really useful and interesting for people to hear. To dig into this a little bit more, was the big lesson and kind of eye-opening moment that there's a lot of foundational work that needs to happen to achieve this outcome that you're trying to achieve, which is measure engagement and adoption well? Is it like tracking and metrics and data science? Is that kind of the lesson there?

Matt MacInnisThe lesson is that everything must be done in its time and order, and you can move really, really quickly. There's no sort of excuse not to move with urgency on all of these things, but you got to do them in order and you have to lead bottom up. You got to lead from the specific circumstances you observe. And I think for me, one of the best things that's happened over the last 11 months is that I've gained a greater trust in my own instincts, that sort of patterns I've matched across other functions do indeed apply in product, but I have both the advantage and disadvantage of not having led a product function before and therefore must think about every problem from first principles. I have no choice. I can read shit on the internet. I can listen to clear thinkers on topics and import their ideas, but I'm very reluctant to import an idea without breaking it down into its constituent parts and figuring out how it applies at Rippling.

And so I don't actually give a shit about adoption metrics as a matter of principle. I care about adoption metrics when I care about adoption metrics. I realize that that's a total logical statement, but it's like I'll get there. And so in certain parts of our product, I really do care about adoption metrics. I care a lot about adoption metrics in our applicant tracking system, our recruiting product, because it's in a really good place from a usability standpoint, it's very well instrumented, it's got very happy users, it's got an awesome growth profile, and so we should still ...

Matt MacInnisIt's got an awesome growth profile. So we should be really focused on the adoption metrics because I think that's going to be an important ingredient to low churn over time, removing friction from the implementation process as an example.

There are other parts of our product where I would say I don't care at all about adoption and am much more focused on foundational things like I said earlier, test coverage or whatever, just to make sure that the thing is stable and good and delivering exactly what it's supposed to deliver once it's adopted.

Lenny RachitskyNow that you're on the inside of the product team, what's something that you think people outside of product, say Matt two years ago or other, I don't know, go to market leads, other execs should hear, need to understand about product that they don't until they're on the inside?

Matt MacInnisI'll give you another framework that I like to use. In the financial world, there's this concept of alpha. Alpha is outperformance relative to the index. So that's why you have seekingalpha.com as a very popular website. What they mean by that is you're looking to buy something, some combination of assets that will outperform, let's say the S&P 500, if that's your benchmark. So alpha is the outperformance relative to the index.

And then you have the concept of beta. Beta is just volatility. Beta's not good. A high beta stock jerks around for no particular reason. It's discorrelated with the index. It's very high beta. Great if you're an options trader, but other than that, it's not really something you want in an asset.
So your ideal stock is a very high alpha, very low beta stock. They don't really come in that shape because alpha and beta tend to be correlated, but that's what you want when you buy a financial asset.
So what's the analogy? I think you have high alpha people who are very valuable. I think you also have low beta people who are also very valuable people. Dennis Rodman, basketball player, nut job, very high alpha. And there's room on every team for one Dennis Rodman is a favorite of mine. It's like you can have one difficult employee who's got a ton of upside.
So this alpha beta thing, I use it pretty often when contemplating what kind of person I want and also what kind of process I want. So when you're building a product from zero to one, you're probably pursuing alpha. You're looking for some angle on this market or this customer problem where the product is actually going to provide an outsized return relative to whatever the default solution is. When you have a more mature product or if you have somebody in the product operations group or whatever, you probably want a more low beta environment where it's like it cranks it out, it does it very reliably.
Our payroll product, we badly want the payroll product to be very low beta. We really don't want the payroll product to have any unpredictability or aberration, and so we're willing to accept more process.
And here's a fundamental principle of design in an organization, which is that processes, processes in a business exist for the sole purpose of lowering beta. Processes are for decreasing volatility in the output of the system. The downside of a process is that it suppresses alpha. And you have to be super, super careful and judicious in the application of process and the product team to know that you're lowering beta in the places where you want to do that without suppressing alpha in the places where you need it.
So as we've gone through the last year of reforming the way that we build product at Rippling, it's been a game of recognizing those places where I need to implement a touch of process, just a touch. Other places where I need to implement a very clear, rigid process where I don't want alpha, I just want low beta. So examples of this are let's say our product quality list, which we lovingly at Rippling call the PQL.

Lenny RachitskyWhy PQL?

Matt MacInnisYeah, so it's actually a really important thing. I think if you want to bring about cultural change in a team ... Look, we have 1,300 people in our R&D organization. It's a big ship that we have to steer. If you want to create a moment that sticks in people's brains and sort of becomes a zeitgeist or something that they latch onto, you got to create an entity, a vessel for meaning, and then you got to fill that vessel with your meaning.

Lenny RachitskyA meme, you might say.

Matt MacInnisYeah, well, sure, a meme. A meme is actually a good example of this in common culture. In pop culture. I think it's why, when people come to the table with ideas from the outside, I welcome those outside ideas. But the first thing I ask the person to do is to tell me what they mean without using those words. So when someone comes in and says, "Hey, I want to do this thing on strategy." I'm like, "Cool. Tell me what you mean without using the word strategy." And it forces them to break it down into its constituent parts. And if they can articulate it clearly without using that word, I know that they know what they're talking about. And if they just fumble around with the word strategy again, I'm like, "Okay, you actually haven't thought this through."

So with the PQL, with the product quality list, it's like I could come up with some generic term for this, but I really want a new joiner at the company to understand that this is an idiosyncratic thing to Rippling. This is unique to us. You want to understand this thing. I also want it to become a component of common parlance in the day-to-day work of the product management and engineering teams. So PQL, as cheeky or silly as it sounds, was deliberately sort of angular or stood out as a vessel I could fill with a particular meaning, and so we have a product quality list.
And the product quality list is lightweight in the sense that it just articulates in the simplest ways the standards we want you to meet when you ship a product. It doesn't apply to every product, not every line applies to every product, but it's comprehensive and it provides me with a framework for iterating over time as we learn.
So just yesterday, we shipped the product to Parker. This is part of our process. When we ship a new product, it goes to Parker, who is the big admin for Rippling at Rippling. If you're not aware, Parker is the sole payroll administrator for Rippling for all 5,200 employees. He personally runs payroll always, there is no exception, for all 5,200 people. He does complain about it sometimes, but it's a remarkable achievement for the software and perhaps for him. So he also installs any new app that we're going to install for ourselves because we dog food the hell out of everything we build.
Yesterday, he goes to install this new application. We're about to ship a new app for feedback, allowing people to give one another feedback on their companies. And he installs it and he goes in and it dumps them onto an empty screen. And he's like, "What the fuck is this? What is this? What's going on? Hey, wow, talk about fail." So I chop another one of my fingers off, I'm down to nine. And I'm like, "Well, what did we miss?"
What we missed was there was a fucking feature flag, a fucking feature flag. And I'm not allowed to say feature flag without fucking in front of it because feature flags are the bane of my existence and the worst things in the world that constantly cause problems. Engineers put one in temporarily and forget about it. It's like shims if you're building a house and the general contractor puts little shims in places and then forgets that they put the shims there and then builds a wall over them and eventually the shim fails and all of a sudden your door doesn't fit. Feature flags are super dangerous and need to be managed carefully, so fucking feature flags.
Anyway, we had one. Parker installs it, they forgot to disable the feature flag. He gets a blank screen when he installs the application. What did I do? My reaction was, "Ugh." Go back to the team, give them direct feedback, tell them not to make that mistake again. But also ask the question, "How do we miss this in the factory inspection process?"
And the answer is we didn't have any line item in the PQL for feature flags. So I added a line to the fucking PQL that said, "You are allowed to have one feature flag that governs your entire product at ship." It's an extreme standard that might not be achievable, but it's the standard we aspire to.
This framework, the PQL, given these lightweight checklists, iterated on consistently in response to everything we learn as we go, constitutes a very nice lightweight way to lower the beta of the system with hopefully only a modicum of negative impact on the alpha for how we build product.
You asked me a very simple question, I gave you a very long-winded answer, but these frameworks help me design systems that scale across one going to 2,000 technical workers.

Lenny RachitskyWow. Okay. By the way, PQL, is that like an acronym or it's just like, I like this word we're going to call it PQL?

Matt MacInnisProduct quality list.

Lenny RachitskyOkay, I see. So it's the . Okay.

Matt MacInnisPQL, which how could you pronounce it other than pickle?

Lenny RachitskyI'm imagining all your decks have little PQL emojis and the-

Matt MacInnisThe pickle emoji thing, the dancing pickle in Slack, there's a lot of-

Lenny Rachitsky.

Matt MacInnisYeah. It lends itself to a bit of fun.

Lenny RachitskyWhat I think about is pickle Rick. Do you get that reference?

Matt MacInnisThis is a Rorschach test.

Lenny RachitskyOkay. So this high alpha, low beta, I love this concept. So the idea is depending on the team, depending on the problem, we need a high alpha, low beta person or actually okay with a lot of variants for this specific project that's actually -

Matt MacInnisYeah, we're willing to accept a bunch of volatility in this area in exchange for the upside we get from the creativity and risk taking of these people or the lack of process that sort of gives them the latitude to do what they want to do.

Lenny RachitskySo when you're hiring, you're looking for, again, is this person low beta or not? That's going to -

Matt MacInnisFor sure. It's really quite a useful way. You know when you meet a candidate and you ... My modus operandi, and I think with talk about hiring for a second, I think I've spent a lot of time with teams at Rippling talking about how I hire. And it is born of batting practice. It'd be super interesting to actually be able to rewind the tape on my life and sort of contemplate how many candidates I've met in every context. Many thousands, maybe tens of thousands, I don't know. It's a lot of batting practice and a lot of model training in my brain.

So I rely a lot of my intuition, which of course HR people say you're not supposed to do. That's complete bullshit. If you have a good intuition, you should absolutely rely on your intuition.
And what you have to do after you have a reaction to a candidate when you're looking at hiring somebody is you need to decode your intuition so that it can be expressed to other people productively. So one of the frameworks that I use for this is SPOTAC. It's a very ugly acronym. There's a hat tip to somebody out there in the universe who originally thought of this. It's not me, but I adopted it. And it's that people are smart, passionate, optimistic, tenacious, adaptable, and kind. Those five things. Six, can't even count. I told you I lost a finger when I made a mistake, so I was down one.

Lenny RachitskyNine to go.

Matt MacInnisSPOTAC isn't by itself a good top down framework, but when you're thinking about, "Oh, why did this candidate just ... Why did it not click? Why did I not like them?" You go down the list, you're like, "Oh, yeah, no, this person, it's that they were not excited about the idea. They weren't passionate." It's that they talked shit about their previous manager and that they were a victim of the performance of their last two companies. That's what it was, they're not optimistic.

The framework is super useful to evaluating people. And I think the alpha beta framework is also super useful when you come away from a conversation and you're like, "I like that guy. I think he'd be really, really good. Why is it that I don't think he would do a good job on this product in particular?" And the answer is like, "This is a high alpha product area and he's a low beta person." Valuable, but definitely not the right fit for this. So I think it's really useful in that context as well.

Lenny RachitskyI love all these frameworks. You're speaking to this audience, framework to frameworks, frameworks.

Matt MacInnisYeah.

Lenny RachitskySo high alpha, low beta, sometimes high beta is okay, SPOTAC. In hiring, is there anything else that you find really useful? Before we move on to a different topic.

Matt MacInnisWhen I first started working in the product organization, I was introduced to an interview framework or an interview tactic that I hadn't really used much at all, I think in my career, which is that every product person at every seniority level is given the same case study. And the case study is extraordinarily difficult. It requires you to think about many, many dimensions simultaneously, to think about data propagation issues. It gets quite technical.

And the rubric that we use to sort of evaluate performance of that case study is it gives you guidance on what for us, like an entry level PM looks like, what a junior, mid-career, senior executive PM might look like. And everybody comes away from that interview feeling like poop, like they had failed it. Whereas on our side of it, we're like, "Wow, that person got really far." They saw around three or four corners in a really impressive way. There was 10 they didn't see around, but they saw around four of the hardest ones. And they were not defensive when we gave them new information that called into question the validity of their solution. And they were willing to interrupt us to ask more questions," and and and, like a lot of the sort of basic human interaction models.
You never think that giving someone an impossible task and even including the L5 person versus the VP on the same thing would be productive. And let's just say our recruiting team still sort of kvetches a bit about this and feels like we eliminate people too aggressively at this stage of the interview process. But I've found the wisdom in it and think it's actually quite useful to give everyone the same simple, complicated prompt and just see. Hand them a drill bit, give them the concrete wall and see if they can get a millimeter or an inch into the concrete. They're never going to get all the way through the wall. It doesn't matter. You're going to learn a lot. And I've found that to be kind of an eye-opening new thing for me that has been fun.
Look, the joy of product and the joy of product management and the joy of being part of product, I think there's a bunch of joys actually, if I could give you a sort of running list, but one of the big joys is that you get to work with some of the smartest people in software. Engineers are very smart. They're not always the best sort of social entities. Salespeople are awesome social entities. They're not always the best systems thinkers. You go down the list.
But the magic of product management is that you kind of have to ... We talk about the mini CEO. I think it's kind of a stupid misnomer, but there's some wisdom there. And I think the wisdom is that you have to be a polymath. You've got to be really good at working with other people. You got to be good at communications and articulation. You got to be good at project management. You got to be good at the science and the math and the engineering. And it's really fucking cool. So I think one of the great joys of this job for me has been interacting with the tippity top of the smartest and most polymathic people in the industry.
I'll say one other thing about what I love about leading product, which is as a COO, my job was to accept the product as it was and optimize everything around that. My job was to make sure that the product operations, in our business, the interface to the insurance carriers, the interface to the payment entities, the government regulators, that stuff all just sort of worked. It was to make sure that our sales engine, our marketing engine, all the go to-market stuff optimized itself around what the product was. It was about recruiting and making sure we got people in to work on the product. You kind of go down any function that isn't in R&D, and I had some hand in trying to figure out how to make that function work to the best of its ability, given what the product was.
And now that I lead product, I'm like, "Oh, wow. This is the high order bit." Not that I didn't sort of understand that, but now I really get that product is the high order bit. If you get the product right, it fits in the market, everything else gets easier. Finance is easier, sales is easier, marketing is easier, recruiting is easier, everything gets fucking easier. So I think the other joy of leading the product function is that I get to set the highest order bit in the business's success to one.

Lenny RachitskyThis is really great to hear. A lot of times people outside product don't understand these sorts of things and look down on product a lot of times, especially sales folks, COOs a lot of times. I love that you're seeing this and realizing this and recognizing just how important and interesting and challenging this work is and just how awesome PMs are. As you know, a lot of people are a very anti-product manager. "Why do we need product managers? We don't need them. Slow everything down, all this process."

Matt MacInnisYeah. I have a distinction there, which is that I'm anti-shitty product managers.

Lenny RachitskyThat's exactly how I put it. If you hate product managers, you just haven't worked with a great product manager.

Matt MacInnisWell, it's like, look, I love wine, wine's one of my things. And I've learned a lot about wine. And one of my favorite lines is like, "I don't like Chardonnay." And I'm like, "No, no, no, no, no. Chardonnay's are the most fucking amazing varieties of wine in the world. You just haven't had good Chardonnay. And there's a Chardonnay out there for you." Product management, it's like you don't like product management, you think product managers suck. It's like, well, you just haven't had a good Chardonnay yet.

Lenny RachitskyThat's exactly what I -

Matt MacInnisOnce you have one, you can't unlearn it.

Lenny RachitskyYou're like, "Let's find that PM ASAP."

Matt MacInnisNo, let's find that Chardonnay ASAP.

Lenny Rachitskywith some Chardonnay. You touched on this product market fit point, and I want to double down on this thread. You've had a couple really interesting experiences of struggling to find product market fit with your own startup. You said you worked on it for nine years, you said?

Matt MacInnisMm-hmm.

Lenny RachitskyOkay. And then with Rippling, complete opposite, extreme product market fit, up and to the right. What's something you've learned about just that that you think people maybe don't understand about what it feels like, what it takes to get to product market fit, how things change?

Matt MacInnisThere's a line that this venture capitalist, whose name I will not mention, said, which was that product market fit is a sort of thing where you absolutely know it when you see it, and therefore if you don't absolutely know it, you don't have it.

And this kind of gets back to my point about learning from mistakes versus successes. It's like, ah, man, over and over again, over the course of the many years that I spent at Inkling, we thought we had it. We thought we had product market fit, maybe, maybe. And in hindsight, with the benefit of now having experienced solid product market fit, it was so, so obvious that we didn't.
And I've invested in like 60 companies or 70 companies. I don't know, it's not something I actively do. But opportunities, by virtue, I think, of my role at Rippling, sort of show up. And I talk to lots of entrepreneurs and I love it and I find it super stimulating and I love the fresh ideas and it's just something I do as a real cherry on top of the sport that I play already. But when I get the investor updates for the guys who've been at it for like three, four years and I read the updates from them that I sent to my investors in 2011 and 2012, I'm kind of heartbroken.
We talk in Silicon Valley about never quit, but that is complete absolute venture capital bullshit. The incentive of venture capitalist is to put money into your company and milk you dry. They never get their money back. There is no way for them to take that investment back. So the only logical desire that they would have is for you to keep trying against all odds because there is the occasional example where someone pivoted from A to X and it was wildly different and it worked. Slack was originally some sort of a gaming company and became corporate chat. Airbnb maybe. It's like there's some examples of companies having made wild pivots and succeeded, but man, is that rare. Just so exceedingly rare.
And I think it's important to remember, I'm 45 years old, we're going to be on the planet, the average age of a man in the United States when he dies is something in the mid 70s. I got 20, 30, maybe if I'm lucky, 40 years left on the planet. Very conscious of the time that I have. And I don't regret what I did at Inkling, I learned a lot. It informed what I do now. I don't think the chapter I'm in right now could have come without the chapters before it. So it's a beautiful, wonderful thing that I did what I did. But when I read the investor update and I'm like, "You're where I was and you are not getting out of this."
The Silicon Valley try until you die mindset is not pro-entrepreneur, it's pro-venture capitalist. And I know why that is, but I think it's important to say out loud that you should fucking quit. You should reset the clock, you should reset the cap table because trust me, product market fit when it arrives is insane and it's exciting and you should pursue it. And never delude yourself into believing you have it when you don't. It is dangerous and regrettable. How's that for a speech?

Lenny RachitskyBeautiful. The anti-VC speech. The-

Matt MacInnisI got more where that came from. By the way, it's not anti-VC. It's anti-

Lenny RachitskyVC propaganda.

Matt MacInnisEverybody's acting in accordance with their incentives in Silicon Valley, the executives, the founders, the venture ... Everybody's, of course, behaving in accordance with their incentives. And the venture capitalists have very strong enduring incentives that have shaped the dynamic of how Silicon Valley works. There's nothing wrong with that. It's just really, really important to point them out and scream at them for the 25-year-old entrepreneur who has no fucking clue how this stuff works.

Trust me, the 45-year-old entrepreneur or the 50-year-old venture capitalist who've been in the game for a while, they get it. They've observed it. They know what it's like. The system is there to take advantage of the people who don't, or at least it is the easiest prey for the incentive structures, not for venture capitalists as individual people who are beautiful and all of them are just really wonderful people. It's just that the incentive structures lead to some real harm, I think, in certain cases.

Lenny RachitskyAnd the thing I find is when you do quit, VCs ... I'm always just like, "Hey, let me know when you're starting your next thing. I'm excited to invest." They're rarely, unless they're not a great VC, rarely are they just pissed at you for how could you possibly not make this work .

Matt MacInnisThat's the thing, as a founder, when it's time to throw in the towel on your business and you're so obsessed with giving money back to the cap table, I always remind the entrepreneur like, "Hey, if you're in the seed investing game, your forecast is zero. Your assumption on every investment is that it's going to go to zero." Any seed investor who doesn't take that stance is off their rocker anyway. They're a very bad investor. Seek investors who play the long game, who want to be in your second and third company and are willing to take a bet on the first one and let it go to zero so that you can get on with stuff. This is like, I've had that conversation many times.
Here, look, history provides us with a clear guide. When you look at companies having hit it big, they hit big pretty quick. It's very, very dangerous to be late to the party, it's very, very dangerous to be early to the party, and the vast majority of the time, that's the problem. Rippling, had it been started in 2014, would not be what it is today. I think Rippling, had it been started today, would not be what-
...Not be what it is today. I think Rippling, had it been started today, would not be what it is five years from now today, and so I think timing is a lot and it's very hard to control for, but when you get the timing right and the market is real and the product works, product market fit, like I said earlier, it's super clear, and so if I were to pick a number out of a hat just from my lived experience, I think it's very important, one aside, don't ask people for advice, ask people for relevant experience. If you ask them for advice, they will always give it, but if you ask them for relevant experience, they rarely have any to offer, and if they don't have any to offer, then don't ask for their advice.

So ask people for relevant experience, and I try to do this with my own entrepreneurs when I work with them, it's like, let me offer you whatever relevant experience I have, and my relevant experience on this topic of when to quit is like, I think we could have called it after the second or third pivot, which was somewhere around year four. It is of course very important to believe in what you're building and to be persistent, but there is definitely no shame in saying, "Look, we've pivoted once or twice. It's not catching. I got to go do the next thing," and I think if you're year four, year five in your entrepreneurship journey, and it's not just obviously a screaming rip-roaring growth story, it's extraordinarily difficult. This is so extremely rare. So beyond even already the rare scores you're going to face from the outset that now is going to convert to something crazy. So that's hard to hear, I guess, but man, it can be really liberating when you're like, "Fuck it, I'm going to do this. I have the energy. I'm going to do it again. I'm just going to do it with a clean sheet."

Lenny RachitskyThat is really helpful. You have this really fun way of describing product market fit around receptors and drugs.

Matt MacInnisOh yeah. Yeah. I think this is a really fundamentally misunderstood dynamic. When founders message me and they're like, "Hey, like my LinkedIn post and my tweet for this launch," I do it. I retweet it, I like it, whatever. Nobody follows my Twitter anyways, it doesn't matter, but I do that, but I think to myself, this is not what this is about. This is not how great companies are built. It can be a nucleating event, but it's not a major thing, because nobody cares about your company. Your launch doesn't matter. Big, fat, pull the slingshot back, launches amount to the teeniest thimble of water in the ocean of noise about startups and companies, and so you just got to build it brick by brick bottom up, and these launches don't really amount to much, and so how do you think about that? How do you think about the insignificance of your launch or you think about all the effort you're putting into building a product that you believe is going to have product market fit?

Well, if you recognize that the market is immutable, no amount of tweeting, LinkedIn posting, advertising is going to change whether the market wants your product. It might raise awareness about your product, but it's not going to change whether somebody wants it. Then you take a different mindset. You have to view your startup as running an experiment in the universe to see what you get in return for that, and this analogy of drug discovery and binding receptors is like nobody at Genentech thinks they can market their way to better performance inside your body. The binding receptors for that drug, they exist or they don't, and when they build their product, their goal is to find out whether the binding receptors exist, but fate already has decided the outcome. This is absolutely true of every software product you build. Fate has already decided the outcome. The market's either going to latch onto your product and run with it or it's not. Do not ship the product, find a lack of success, and then try to market your way through that, because the binding receptors likely don't exist, and for me, it was a very liberating mindset, because now I just have to find the right drug, and I can forget trying to convince the body to develop the binding receptors for whatever it is that I'm building.

Lenny RachitskyWhat I love about your advice here is you were an early investor in Notion, which is one of the classic stories of it took them... I think it was four years to get to something. They moved to Japan, they worked on the whole thing, and so is from there? Is that a rare example where it actually worked? And that's not an example to be inspired by, because it's extremely, extremely rare. Let's talk about alpha beta again.

Matt MacInnisOkay. As an investor, you might build a checklist of things you want to make sure are true or false about a company and hope that that's going to yield the kind of investment success you're looking for. Does it have this kind of founder? Is it a C Corp in Delaware? Boom, boom, boom, boom, boom, boom, boom, and these checklists are all about what? They're all about suppressing beta. They're about avoiding avoidable mistakes. They're about bringing stability. Jeff Lewis is an investor who has many angular views on things, and I think one of his most enduring phrases is narrative violations. This idea that the common wisdom must be violated in some way by every company that has an outsized success. It is absolutely true, and when I give these general observations on the patterns in Silicon Valley, the most successful businesses inevitably violate something on that list in some really important way.

So Notion, you can't replicate Notion's success as an entrepreneur. You can't replicate it because you're not Ivan. You can't replicate it because you're not Notion. You can't replicate it because it's not 2010 when they started the company. Do the math on that. Or 2011, actually. These guys stuck with it. They went through hell. They pivoted. They went to Japan and sat in kimonos and meditated on what they were going to build, and by hook/crook, they got to where they are today as a really wildly successful business in an extraordinarily difficult market where building businesses is virtually impossible in productivity. It is dominated by Google and Microsoft. Carving out your own niche in that market is just unthinkable, and so I look at Notion as having succeeded by virtue of the narrative violation of persistence, I don't think is a good idea for very many people that happen to work for them, and I look at it as being a function of the founding team and their specific idiosyncrasies, the absolute insistence on craftsmanship from Ivan. This is him. That's his thing.
The takeaway lesson is not give up or don't give up. The takeaway lesson is certainly not go do what Notion did. The takeaway lesson is that every company succeeds on the foundations of the idiosyncrasies of the founder. The idiosyncrasies of the founder. Rippling succeeds for almost the polar opposite reasons that Notion succeeds, but in both cases, the companies succeed on the idiosyncrasies of the founder, and so embracing that, recognizing those idiosyncrasies, that's what great investors do. They spot that element of spikiness and greatness in a candidate investment, and they convert that to a commitment, and then of course the investor or the good ones accept what they get in exchange from that for the universe, from the universe.

Lenny RachitskyI love that we went in this direction. I wasn't planning to talk about your investing career. Just to give people a reason to listen to this and maybe rewind, and I want to ask another question around investing. What are some other companies you invested in early?

Matt MacInnisFirst of all, okay, so I sort of hate the question. What are some other companies you've invested in? It's a fair question, but the problem is I'm going to give you a bunch of companies I've invested in that won, that are really notable. So what I would like to do instead of answering that question ... Here, let me give you some bait. I was one of the first investors in Notion. I was perhaps the first, I don't know, ask Ivan. Clever, which had a great exit. I was one of the first investors in Zenefits, if you've heard of it.

Lenny RachitskyHeard of it.

Matt MacInnisI was, before I joined, one of the first investors in Rippling, and then more recently invested in ... Here's a funny one. I was one of the first investors in Deal, if you've heard of them.

I was able to exit that position, and then hopefully that company's going to zero with their criminal behavior, but whatever, but more recently, if you know Decagon, which is doing some really cool stuff on the AI front.

Lenny RachitskyKilling it.

Matt MacInnisI'm in laying chain. Great. So those are some companies that you maybe have heard of, but how about I invested in Macro. Founder was Derek Lee. Macro's out of business. I invested in Debrief, Ned Rockson. It's out of business. I invested in Verb Data with David Hertz out of business. I'm reading from a list. I invested in... What's the number? 70 companies according to this list where I track things and most of them went to zero and all those founders were awesome, all those founders were kick, and all those founders put a ton of energy into building their businesses, and they went to zero and they're enduring relationships.

I can call on any of those people, I think, maybe with the exception of Deal, and call in a favor and have... and I've got a few subsequent... and actually a lot of them joined Rippling, believe it or not. So I don't know. Companies I've invested in is a long list, and I love to give you names of companies that don't exist anymore because it's self-serving and a horrible survivorship bias to just list the good ones.

Lenny RachitskyI love that answer. I think you're being modest in the context of your hit rate is clearly very high. Even one or two incredibly successful companies out of 70 is a win in VC, and so you're doing very well, but I think that's a really important perspective. When you see people's logos on their websites of all the companies they've invested in, you have no idea how many hit bats they've had.

Matt MacInnisI think it's good practice to ask people to give you the full list. Yeah.

Lenny RachitskyWhat are your favorite failures that you've invested in?

Matt MacInnisOh, no. I'm not actually... Okay.

Lenny RachitskyWell, obviously, no, we don't need spend time on it, but I think it's actually a really good question, but yeah, what are some of your best failed investments? Show me the logos of the companies that didn't work out.

Matt MacInnisIt's a juicy question. Yeah.

Lenny RachitskyThere's a topic around this area that I wanted to spend time on, and I haven't heard anyone think of things this way, which is this idea you talk about of compounding plus power law plus entropy and how that's a really useful frame to think about business.

Matt MacInnisSo you kicked this conversation off sort of invoking the extraordinary outcomes, demand, extraordinary efforts line, hat tip to Dan Gill, and these are part and parcel. Man, understanding the nature of the universe is a pretty good way to work within it, and so power law distributions happen everywhere. It explains why so few people control so much wealth. It explains why Steph Curry is just so vastly better than the next guy down on the list on the basketball team. It explains why populations are concentrated into a relatively small number of mega cities in the world. It's like, power law distribution just plays out everywhere, and once you see it, you can't unsee it. It sort of plays out in many dynamics.

People tend to think that the world plays on a more linear relationship where the X and Y axis are sort of Y equals X, but that is absolutely not the case, and the implications are profound. It's like if you build something to 80 or 90%, the Y axis is barely budged yet. You haven't hit the inflection point in terms of reward, and so the implication of the power law more broadly is that people who are in the top 10%, the top 5%, don't just get 10 or 20% more reward. They get 10X the reward or 100X the reward. It's really dramatic.
Entropy, the second law of thermodynamics is a very simple concept. It's the reason your sock drawer becomes messy. It's the reason that potholes form. It's the reason we have to put so much energy into maintaining the aircraft we fly to keep them safe because they really, really, really want to fall apart, and that's the nature of things. If you abandon a city for a few months, it starts to go fallow, and so entropy is just this concept that shit tends toward disorder.
The universe, I mean, life itself is a temporary victory against entropy. You and I should not exist. The sun gives energy to the planet. It organizes stuff that we can eat and we fight entropy until we lose the battle somewhere, as I said earlier at the age of 70 or 80, if we're lucky. What does this have to do with product? This is really about effort.
The only antidote to entropy, the only antidote to decay in a system is energy. You got to inject energy. So if you have a code base, every line of code that you add to that code base increases the entropy of that system and demands ever more energy from human beings to go and intend to it to make sure it doesn't break, and if you want to achieve greatness, if you want an extraordinary outcome, and in particular, if you want to be in the top 10%, top 5% on the X axis so that the Y axis is through the roof, then you have to relentlessly inject energy at every single step of the game. Teams will, sadly, but because we are all human, teams will always optimize for local comfort over company outcomes.
Not because they get together and think, "We should do that," although unions do do that unequivocally, deliberately, but even in a collection of product managers or engineers, what's going to happen over time is entropy is going to creep in and people are going to optimize for local comfort. Your job as an executive, as a leader, is to fight that entropy tooth and nail every single day. It means that every time you see a bug, every time you see a bug, not most of the time, every time you go and you drop it at the feet of the product manager or the engineering manager, every time, in public, preferably, it means that every time someone comes to you to hire someone and says that they have skipped the back channel, every time you're like, "You can't hire this person unless you do the back channel," it means that when you get into the board and tired zone on any process, that you as the executive have got to demand the 99th percentile of energy, because otherwise entropy creeps in and the system decays. You have to do this.
One of the messages that I delivered recently at our big executive big... Like our top 75 manager offsite that we do roughly every 18 months, was a reminder that if the purest form of ambition and the purest and most intense source of energy in the business is the founder CEO, that every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity, and that is dangerous because if you go to two layers and it's two orders of magnitude drop off and signal and intensity, that is a very dysfunctional organization. So what I say to the team was, it's not that you need to buffer people from the intensity of the CEO, it's that you need to absolutely mirror that intensity.
There are plenty of constituents in the business around you who will advocate for relaxing. There is an infinite supply of people under you who will buffer other team members from the intensity of the demands. Your job is not to be one of those buffers. Your job is to preserve that intensity at its highest possible level and let the buffering happen somewhere else, and that's the point is that entropy creeps into the system insidiously and slowly over time off your radar and you have to maintain that intensity every minute of every day to try and fight it if you want to stay at the extreme right end of the power law that obviously governs the outcome of everything that we build.

Lenny RachitskyWhat does that look like to pass along that intensity? What does that feel like? What does that look like? So say Parker comes to you, "This bug sucks. I got this broken screen." You cut off your finger. Maybe that's the example.

Okay. Still got them. I got all 10.

Matt MacInnisI'll give you concrete examples. Actually, the joke that I sort of played on this one when I presented to the team was that the next sort of slide in my presentation was with the sound effect, the Slack huddle thing, and Parker's icon in Slack is just, he uses the generic yellow...

Lenny RachitskyThe egg?

Matt MacInnisYeah.

Lenny RachitskyOh, wow.

Matt MacInnisIt's funny, and so everybody knows the yellow egg is Parker, and so the next slide in the presentation was boop, boop, boop, boop, boop, boop, boop, which is the sound that Slack makes when someone calls you, and it was Parker Conrad is inviting you to a huddle, and then the next slide was Parker Conrad is modeling personal intensity, and the idea is that if you know, you know, if you've ever been dragged into an... "I want to talk about this fucking problem right now and whatever you're doing, unless it's an interview, I want you to come and have a conversation with me."

That intensity is one place where it plays out. Every product team at Rippling, and we have a lot of them now, have public feedback channels. I am in there upside down on everything I find when I use those products, and I just model for everybody that this is how at least I want to do it, which is, "I don't like this. I don't understand this. Tell me why this is this way." Boom, boom, boom, boom, boom, and people jump in and respond. The factory inspection process that I mentioned, which is where at the end of the assembly line, I jump out with the pickle and we talk about all of the elements. You have to record a loom of every major flow through the product. I personally review every one of those flows, I got a backlog I got to catch up on today and provide feedback to people always in a public channel so that every other product manager and engineering manager can jump in and see how the process has worked for other teams.
It's about modeling the intensity publicly so that other people can say, "Okay, this is how we do things around here," and it gives the reaction from the team that received the message that you have to inject that energy every minute of every day and that there are no exceptions, was not like, "Ooh, that's exhausting." The reaction is, "Oh, that is so invigorating." It's so wonderful to hear that we're going to achieve these great outcomes, or at least we have a shot at doing so, and that you're empowering me to follow my instinct, which is to really push for the best result.
The reaction universally is like, "Ugh, what a relief that I get to go be intense," because nobody in a position of leadership wants to be chill, and what's worse than a chill boss? No, don't work for a chill boss. Don't be a chill boss. It's the most pejorative label I could give you. Chill boss or chill PM. Don't be chill. Chill doesn't accomplish shit. Be intense. Be good, be respectful, be intense. Don't be chill.

Lenny RachitskyAgain, this advice comes from where we started, which is this is what success looks like, because somebody that is less chill than you is going to find that crack and come after your market. Is that the gist?

Matt MacInnisFor sure. I mean, again, if you're chill and you move the X axis down 10 or 20 points, the Y axis collapses. It doesn't just drop 10 or 20%. The Y axis collapses, and this is just kind of true in everything we do. So yeah, if you want to win, you should probably try.

Lenny RachitskyThis is what I always say to people trying to build lifestyle businesses. There's always this idea, "I'm going to build a side business, I'm going to make recurring income, it's going to be amazing," and in my experience, anytime there's a market or something shows up that's juicy and there's ways to make money, somebody's going to come at you and work harder, raise more money, and there's only so long you can maintain that.

Matt MacInnisWell, man, there's a whole other podcast episode on the concept of leverage. If you sell your time, you've only got 24 hours a day to give, but if you can create a product that scales, the marginal cost of a unit of that product is zero like software, it's going to be competitive, man. Sell your time, it's not going to be super competitive, but achieve that level of leverage and it's a pretty efficient market.

Lenny RachitskyTo close out this thread of intensity and adding energy to everything, something I've heard about you is you're big on escalating. You're a big fan of escalating issues, and also you always tell people to never not give you negative feedback, to always share feedback to not hide anything. Tell me about those two.

Matt MacInnisFundamentally, the most selfish thing you can do is withhold feedback from someone. Who are you optimizing for when you do that? What are you optimizing for when you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable? Well, you're optimizing for your own comfort and it's fundamentally selfish. It's the most selfish thing you could possibly do, is withhold feedback that would otherwise be useful to someone because you don't want to be uncomfortable. Well, that's not how high performance teams operate. So I demand feedback, and I give it, and it doesn't mean that when I give feedback, it's not open to being questioned or discussed. I mean, of course it is, but when I observe something, I try to say it. That's the feedback topic.

The part of this that has been interesting to me is that people withhold, escalate, the customers withhold. Customers don't want to escalate to me as an executive. Even the founders in whose businesses I've invested who use Rippling are reluctant to hit me up when something goes wrong because they don't want to bother me, but it's literally my job, literally my job to find things, problems, and make them better, and by virtue of making those specific things better, to iterate on the processes so that the system that builds the system can get better.
There's no greater gift to me as a product executive than receiving an escalation from a customer. We have an escalations team at Rippling, which sounds weird, but it's people who are just particularly skilled at pistol whipping other people in the company to get to real root causes, real root causes. Not like throw away the word root cause, like, "Oh, we fixed the data error and shut the ticket down." No, you went and you found the software that created the data error, and then you found the system that created the software that created the data error, and you solved all of that back to the top.
Escalation seems extremely good at that at Rippling. So we have sort of a dedicated little team that does this for us. Escalations are a gift, and it's like, if you're a listener right now on this podcast and you are a Rippling customer and you have shit that you think we should know, the fact that I might already know it is not a reason for you to withhold the gift of your feedback. So it's an attitude that I take to this every day. I've got a little cue of some stuff that I've... Minor things that are from the last couple of days from people who had some knits and issues that I'm just like, I've got them queued up on my to do list today and I'm going to take them to the product teams directly and be like, "I'd like to understand what happened here." Not in a negative way. I just think we'll all get better if we study this one, and so yeah, escalations are a gift, feedback like that is a gift, and nobody is ever inconveniencing me when they do it.

Lenny RachitskyFor people that are listening to this and feeling like, "Man, this is so stressful and intense and just like, I don't know if I want to work this way," give them a sense of just how successful Rippling is. I think a lot of people may not even have heard of Rippling. A lot of people are like, "Yeah, it's doing great." What are some things you can share that are public or not public that give people a sense of just how massive this business has become?

Matt MacInnisPeople look at Rippling from the outside, I think they think of us as payroll and HR or whatever, which is cool. It's a bit like saying Microsoft is a desktop operating system company or it's like every company starts from somewhere.
... system company or ... It's like every company starts from somewhere and grows out from there. We see ourselves as building the most successful business software platform in history. In fact, that's the mission statement of our product organization under the umbrella of the mission statement of the company, which is to free smart people to work on hard problems. And when you translate that from where we are today to where we think we're taking things, it's like we really do believe that the core of every workflow and everything that a company has to do, be it AI or manual traditional GUI based software, is who's doing stuff, who owns it, who's accountable? And so the people record is a really important component of that. You can argue that the customer record's also very important. And of course some big businesses have been built on that primitive as well, but we think the people primitive is actually much more important.

And that the only thing that hasn't been done here is somebody hasn't been ambitious enough to build a good business on top of that primitive. Workday is terrible software. Everybody agrees on that. I think Workday agrees on that. Good luck to them. But they have failed actually, despite their success, to build a really broad general purpose software platform for business software on the foundation of the people primitive. So we're going to do that.
And we're successful because we deliver on that promise at the scale we're at today. The fact that you can do ... and this is not a sales pitch or sort of like an advertisement for Rippling. I just think it's important to sort of contemplate that when you bring together a bunch of disparate business processes into one system on a common business data graph, an object graph, a data lake with a consistent interface, you can do some pretty magical things.
So we do payroll, we do HCM, we do IT, we do spend. We are about to launch a new product in the category of business intelligence and data management. And there's a whole bunch of other stuff coming beyond that. And then you layer in AI on top of this, where we alone, where we alone have all of your business data organized into this nice, neat package with a beautiful semantic layer on top of it. The AI can work magic. And we have shipped nothing, nothing yet in this category that I would say gets anywhere near what we're going to show next year. And it is going to set the standard. It is going to be the most ... The back flips that the AI is doing reading and writing data for the user just on our internal use cases at Rippling is jaw dropping. So I'm super excited about the tailwind this is going to create for us.
You ask about what can I share about the success of the company? What I can say, there are tens of thousands of companies that now run on Rippling. We're less than 1% of the market. And the market cap at 16 billion, I think now undervalues where we are from a revenue perspective by a long shot. There is just so much upside to do what we're doing. And SaaS might be dead-ish in terms of point solutions, but long live SaaS in terms of what we're building.

Lenny RachitskyLet me follow that thread in AI. There's been a lot of talk about AI is going to replace SaaS, as you maybe just said.

Matt MacInnisYeah. People are going to vibe code their way to their payroll system, which I ... good luck to the employees of those companies.

Lenny RachitskyAnd so what I'm hearing here is that you actually do believe a lot of SaaS companies that are selling individual solutions are in big trouble. The answer implied here is this kind of compound startup idea of you need to do a lot of things for people for them to continue to pay for your software. Is that the gist?

Matt MacInnisNo. I think the gist is ... there's a really good quote. I forget who it's attributable to, but it's, "There's two ways to make money in software, bundling and unbundling." And you just got to get the timing right. So this is a period of bundling. So here's the problem; point solutions don't have enough data in the age of AI to be useful. You got to be able to provide the AI with a lot of context about a lot of data so it can do things. It can do joins. It can do correlations.

And so if you're a point solution, you're in hard water because you've got to now rely on data from other sources. You've got to integrate to third party systems. And when you integrate to a third party system, even the best ones are still sort of drinking their data through a straw, which is a real problem. I mean, the biggest HCM software company you can think of integrates to the other biggest payroll software company you can think of through flat files via SFTP. What are they going to do? What are they going to do? It's just never going to work. It's just no way. And so I literally have no idea what they're going to do. They're just not going to build AI software, I guess. Point SaaS is sort of in a rough spot, especially when you cleave two really important systems apart and say they have to integrate. It's very, very hard.
The other thing that I would say about the world of, even just like not SaaS, but AI software is that point solutions in the AI world are also in a rough spot for the same reason. It's like if you're selling the shovels like OpenAI and Google with Gemini, you can make money. And if you own the mine, like Rippling, with the data, you can make money. If you're somewhere in the middle, building AI software that then tries to use the shovels from the shovel provider, but then also needs to rent out the mine, or get the ore out of somebody else's mind and start refining it, you're in a very difficult place from an economic standpoint. Because you're not going to be permitted by either of those parties to build a big business on their backs.
That's just not how it's going to work. They're going to demand value capture that crushes your unit economics. So I look at the landscape of AI companies that I've seen and I think you have to have a really durable, interesting insight that gives you a shot at viable unit economics to be an interesting business. And that is going to kill off 80 or 90% of the stuff that I see right now as standalone AI businesses.

Lenny RachitskySo what I'm hearing here ... I love that you correct me when I get these things wrong, and that's exactly what I want. What I'm hearing is it's less about how difficult it is to build the SaaS product. It's about, do you have first party data that allows you to build an incredible AI product on top of what you've got?

Matt MacInnisYep. Because look, SaaS software is a bit flipping. All SaaS software applications are bit flippers. It's an interface changing-

Lenny RachitskyYour database?

Matt MacInnisYeah. Changing values in your database, that's what it does. It's a really hard problem. One of Rippling's superpowers is we're a coin sorter. You dump $20,000 for an employee in the top of the coin sorter, and it figures out what goes to the government, what goes to health insurance, what goes to your 401k, what goes to you. And it has to move all that money very, very reliably and seamlessly, very challenging software to build and manage. What's it doing? Even that is just flipping bits in a database. And so AI is a new way to flip bits. AI is just a new way to flip bits. Hopefully a way that abstracts us a little bit further from having to think because our future is Wally. It's going to be great.

Lenny RachitskySpeaking of Wally, actually, I have this Matic Robot. You have one of these?

Matt MacInnisUh-huh.

Lenny RachitskyNo. It's like a self-driving car robot, basically, a self-driving car. People built this robot that cleans your house. Maybe I didn't mention that. It's like a house cleaning robot that just goes around.

Matt MacInnisOh, okay.

Lenny RachitskyIt's like a Roomba. You should have one. They're expensive, but incredibly cool. And actually in Wally, there's a scene where they actually have basically what these things look like. So it's not so far-fetched for that movie.

Matt MacInnisI definitely was actually quite prescient, perhaps with the exception of the gravity defying day beds.

Lenny RachitskyYeah. I don't know, but that's not good news. You've seen that movie. Oh, man. So on this AI stuff, which I'm hearing is we're going to see a lot more consolidation where these point solution companies realize they need this data. This is existential, and they're going to combine and merge and bundle, as you described?

Matt MacInnisIt's possible.

Lenny RachitskyOr for now.

Matt MacInnisI am not an investigator on this stuff. I think there's some really interesting investors out there who I think are thinking quite deeply about this. And in particular, the conviction, which is like Mike Fornell and Sarah Guo. I think those are two investors who are hyper focused on AI. And when they made the decision to take that approach, at the time I thought that's kind of narrow. Now I'm like, no, no, no, that was the right move. And it just means that they have a very deep, deep, deep set of hypotheses that they've formed over the course of seeing every AI deal in the valley. And there are better people to ask this question of than I am. And I think if you're an entrepreneur, I recommend them to you because I think they're really smart.

Lenny RachitskyAwesome. I love those guys. Also, Sarah and Elad have a podcast called No Priors that I'd also recommend. We'll point it to you in the show notes. So on this AI note, I guess is there anything else that you think would be really helpful for founders that are working in this space building an AI startup to hear they think you were seeing of like, here's what you need to do to win in an AI company?

Matt MacInnisSo much. I actually think that if I were to give you an answer to this question right now, it would be bullshit. Yeah. I don't have anything ... Back to my point earlier, I don't have enough relevant experience in the abstract to dole out on a podcast on that topic, but I wish them luck.

Lenny RachitskyI love that. Circling back to your advice, don't ask for advice, ask for a relevant experience. And I love that that's where your mind immediately went. I'm going to take us to AI Quarter, which is a recurring segment on this podcast. And the question is just what's one way you've found AI to be useful in your work day-to-day? Is there something that you found it unlocked in how you work?

Matt MacInnisI mean, it's not a super exciting thing, but I'll say where I use ... So one of the most important functions that I perform as an executive is the synthesis of ideas, and the ability to communicate those ideas very clearly to people. So when I talk about the product quality list and the pickle, as something that we've come up with internally, I do turn to AI, ChatGPT and Gemini, where I take a really, let's say, angular view of some topic and I give ... really, I write the essay for the AI and I'm like, "Look, this is the crisp idea I want to communicate. Help me come up with pithy ways to articulate these things." And 80% of what it outputs is trash. It's just sort of middle of the road, average, low alpha junk.

But it is a thought partner, a non-judgemental thought partner where in 20% of the stuff it comes out with, I'm like, yeah, it's pretty good. That's a new word I didn't think of. That does kind of hit the nail on the head for this concept. And so if I believe that my job is to sort of bring brains along on the journey for some sort of change that I'm trying to bring about, then the most important tool is language. And I do find that the ChatGPT and Gemini do a great job of helping me refine how to articulate the concepts that I want to articulate. They are not useful in coming up with the ideas themselves.

Lenny RachitskyThat's an awesome tip. I don't know if you've played with Claude much, but I actually find Claude is better at writing and words and language.

Matt MacInnisI have not spent a lot of time with Claude. I have used it, but by virtue of this conversation, I'll probably go give it a go.

Lenny RachitskyRight. Yeah. They're all great, but there's something about Claude that is just at writing specifically is much better, but they're all getting better all the time. There's always something new.

Matt, we've covered so much ground. We've touched on everything I was hoping to touch on. Before we get to our very exciting lightning round, is there anything else that you were hoping to share or anything else you wanted to touch on or leave listeners with?

Matt MacInnisYeah. We've spent a lot of time talking about intensity and the grind, and the need to just always be operating at the 99th percentile. And I think if you listen to that in a vacuum, it's very easy to believe that that intensity is soul crushing, that it's a negative, that it's maybe not something that you want. And I think there's a backstop for me that I didn't talk about today that I think is important to share, which is that life is amazing. That the fact that we all exist on this blue marble drifting through space and time, that we are some weird instantiation of consciousness, each of us, and that you're here for such a short period of time whittling your stick, doing something, that if you remember how insignificant we are and all of this is, it brings this levity to what we do and to the work we put into building this.

Because Silicon Valley in 2025 is Florence and the Renaissance. It's crazy. The amount of creativity and insane invention and progress that's happening for our species right now in this place is absolutely unparalleled in all human history. You've got to zoom out and appreciate that magic. And so then you turn around and you're like, fuck, I've got to work on Friday night, right? I've got to go give it my all. I've got to go compete in the arena of business.
You have to never forget that number one, none of this matters. And number two, it is an absolutely beautiful and amazing phenomenon that we get to be alive doing this right now. So play the sport, play it with everything you've got, but never forget that it's just a sport and that none of it matters. I think it's super important as a counterpoint to the intensity that we talked about.

Lenny RachitskyThat is beautiful.

Matt MacInnisI think about Pale Blue Dot, Carl Sagan's whole thing. Just a stunning photograph that literally changed the way I think about who I am as a person when I saw it. Yeah.

Lenny RachitskyWell, going in a completely different direction, with that, Matt, we reached our very exciting lighting round.

Matt MacInnisOkay.

Lenny RachitskyAll right, five questions for you. Are you ready?

Matt MacInnisOkay.

Lenny RachitskyHere we go. What are two or three books that you find yourself recommending most to other people?

Matt MacInnisOkay. Two or three books. You give me a heads-up on this. So one book is Conscious Business. I don't have Conscious Business in front of me because it's actually at the office because we have Conscious Business Reading Club at Rippling. And every member of my current, my product leadership team is going through this right now, Conscious Business, Fred Kofman. It's been used in many businesses, LinkedIn most notably, as a framework for thinking about ... effectively, it's a user manual for human beings. So if you are a leader, a manager, an executive, whatever, particularly younger people in their 20s and 30s who are just sort of getting the hang of being a CEO or a product leader for the first time, this book is absolute fucking gold. It was recommended to me by Bryan Schreier at Sequoia when he was on my board at my previous company. I took way too long to take him up on the advice, wished I had read it sooner. Highly recommend Conscious Business. Changes your life.

Number two, Thinking in Systems, Donna Meadows. I always mispronounce her name, Donella Meadows. She died partway through writing this manuscript. Her fellow professors picked it up and finished it for her. It is the best generic framework for thinking about how systems work. You will extrapolate from this book to every aspect of your life after you read it.
And then the third is classic 1960s, The Effective Executive. It's an anachronism. It uses weird pronouns for the secretary and the executive. I'll let you guess which ones. But the book itself is so chock-full of simple enduring advice on how to be effective at leading teams. And the good shit is the stuff that's been in print for 70 years, and that's one of them.

Lenny RachitskyBeautiful. I love the first one is you don't have it because you're using it with your team constantly. You mentioned at one point before we started recording, you have eight copies of that book that you just give out to everyone.

Matt MacInnisYeah, and we handed out like candy.

Lenny RachitskyOkay. Is there a favorite recent movie or TV show you've really enjoyed?

Matt MacInnisYeah. So I'm a little embarrassed by this answer, but I'm going to be honest.

Lenny RachitskyPlease.

Matt MacInnisThere's a new series called Heated Rivalry and it's about ... I'm Canadian and I'm gay. So it's about two hockey players. In Canada, rivals between the Bruins and the Maple Leafs, although they don't use those names, who are just heated rivals on the ice. And it's a huge thing that the world is watching, but actually they're secretly in love with each other and they start hooking up. And it's been labeled by the media as smutty but delightful. And I would say that's accurate. So it might not be for everybody, but it is a smash hit right now. It's on HBO Max and Crave, and it's only six episodes. But like I said, a little embarrassing because it's a little chintzy, but it's a lot of fun. It's also really fun to see gay people represented in the media as though they're normal, and it's fun.

Lenny RachitskyAnd soon to be on Netflix with the acquisition if that goes through.

Matt MacInnisOh, yeah.

Lenny RachitskyIt's crazy. Amazing. Okay. Is there a favorite product you recently discovered that you really love?

Matt MacInnisMy Fellow coffee maker. I love my Fellow coffee maker. It's got an interface that lets you set light, medium, dark roast. It changes the temperature. It blooms the coffee. It tells you how many grams of coffee to put into the basket, slick interface, high quality coffee. It's definitely awesome. And so I have Ashley have one in the office and one at home and one in the garage.

Lenny RachitskyWow. That is a favorite product. You have three of them in the same cool space.

Matt MacInnisYeah.

Lenny RachitskyOh no, in the office. Okay.

Matt MacInnisFellow is also a Rippling customer and that's a nice side effect when we get to ...

Lenny RachitskyHave they ever escalated anything to you?

Matt MacInnisNo. If you're listening and you're from Fellow, I want to hear all your gripes.

Lenny RachitskyPerfect. Two more questions. Do you have a favorite life motto that you find yourself coming back to often in work or in life?

Matt MacInnisIt's a dark one, and I'll share this one sort of partially for the humor of it, but it's actually sometimes useful immediately. At least it's sort of a moment of smiling when it happens. The motto comes from my dad who said, "Matt, nothing's ever so bad in life that it couldn't get worse." And it's like we were going through some shit yesterday at work and we were like, "Fuck, now that happened." And I looked at the CTO and I'm like, "Dude, nothing's ever so bad that it couldn't get worse." And we had a good laugh and continued to brace for whatever might come next. So not exactly uplifting, but fun to use.

Lenny RachitskyNo, it is uplifting. I'm an optimist and I find myself thinking that often with my wife just like, "It could be worse. It could be worse than this. " Definitely. It's actually .

Matt MacInnisAnd it might get there.

Lenny RachitskySo let's enjoy this less worse version. Final question. Something you shared with me is that you were a DJ when you were a younger person. Can you just give us a little DJ voice to give people a sense of your skills?

Matt MacInnisWell, so first of all, it's not DJ, Lenny. It's radio personality. And yeah, I used to do the greatest hits of all time with hits from the '60s, the '70s, the '80s, and a little bit of the '90s, 101.5 The Hawk. Yeah. You can turn it on. It's very inauthentic, but it sounds good on the radio. It's cool. I did it when I was in high school. I ended up doing the midday segment right before I went to college. And what a gift. What a huge gift in my most formative years to have developed an ability to be in front of a microphone comfortably, because here we are.

Lenny RachitskyI love for people that weren't watching this YouTube, you lean really close to the mic to get that radio personality voice.

Matt MacInnisYeah, you got to be able to hear the saliva in the mouth.

Lenny RachitskyIncredible, and it's like the same person talking. If you're not watching this, you're like, "Where did that guy come from?" That was great. You nailed it. Matt, this was incredible. I really appreciate being here. I really appreciate you sharing all this advice that I have not heard other people share. Two final questions. Is there something you want to plug, point people to, and how can listeners be useful to you?

Matt MacInnisLook, my life is rippling. I point people there, and this is my life's work. It's going to be a banger, so stay tuned. And the way that you can help me is that if you're a customer, you got to tell me when you have problems, because that's how we get better.

Lenny RachitskyWhat's the way to get to you? Is there any place you want to point people to?

Matt MacInnisDM me on Twitter, is easy @stanine. You can email me my last name at rippling.com, and I'll go that far without giving out my phone number. How's that? Perfect.

Lenny RachitskyA perfect boundary.

Matt MacInnisYeah.

Lenny RachitskyMatt, thank you so much for being here.

Matt MacInnisIt's my pleasure. Thank you for having me, Lenny, and congrats on all the success with this podcast. It's been great.

Lenny RachitskySame to you. It's always a good sign at the end of a conversation when you're like, oh, I got to get me some of that stock and I got to get into that Rippling.

Matt MacInnisIt's a good buy.

Lenny RachitskyA great job.

Matt MacInnisRecommended by-

Lenny Rachitsky15 billion.

Matt MacInnisYeah, but you're

Lenny RachitskyYou're hard to get All right, man. Thank you so much.

Matt MacInnisThanks.

Lenny RachitskyThank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

Matt MacInnisIt is really important to me that we feel that we've deliberately understaffed every project at the company. If you overstaff, you get politics, you get people working on things that are further down the priority list than necessary. That is poison. It's wasteful. It slows you down. It creates cruft.

Lenny RachitskyYou've been a long time COO at Rippling. Recently, you moved into CPO, Chief Product Officer at Rippling. Something you talk a lot about is that extraordinary results require extraordinary efforts.

Matt MacInnisIf you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. You got to sort of remind people that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. It's supposed to be really fricking exhausting.

Lenny RachitskyYou're a big fan of escalating issues.

Matt MacInnisFundamentally, the most selfish thing you can do is withhold feedback from someone. When you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable. Well, you're optimizing for your own comfort, and it's fundamentally selfish. So many people have teams that are not functioning incredibly well. Teams will always optimize for local comfort over company outcomes. The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity. That is fucking dangerous.

As an executive, as a leader, your job is to preserve that intensity at its highest possible level. You've had a couple really interesting experiences with your own startup. We talk in Silicon Valley about never quit, but that is complete absolute venture capital.

Lenny RachitskyToday, my guest is Matt MacInnis, Chief Product Officer and formerly longtime Chief Operating Officer at Rippling. If you don't know much about Rippling, it's a massively successful business last valued at over $16 billion. They have over 5,000 employees, and Matt has been instrumental to that success. He's also got a really rare combination of brutal honesty, a ton of experience building a very complex and very successful business, and being able to clearly articulate what he has learned really well. Matt shared a lot of insights and advice that I've not heard anyone else on this podcast share, and I left this conversation feeling that every leader needs to hear his advice.

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Matt, thank you so much for being here and welcome to the podcast. Thank you for having me. I want to start with something that I know is really important to you, something you talk a lot about that I don't think people hear enough on podcasts like this, which is that extraordinary results require extraordinary efforts. Talk about why this is so important, what you think people need to hear.

Matt MacInnisThis is a term, that phrasing I actually attribute to a friend of mine, Dan Gill, who's the chief product officer at Carvana, which as a company also doesn't get enough credit for how much of a tech company it actually is. Super interesting. And I think as a general framework for me, and a lot of what I say with you today is not really specific to product in any way. We should actually talk about that. It's like the product function is an instantiation of the general concept of management. Being a chief product officer is not that different from being a chief whatever officer. You have to apply the same frameworks and concepts to get people to achieve goals together. But one thing that is absolutely universal that I think we, honestly, I think we forget it in Silicon Valley or a lot of people don't sort of internalize it, is that if you want to accomplish something truly extraordinary, if you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult.

It's going to be really uncomfortable. And you got to sort of remind people of that, that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. They have definitely screwed up somehow. It's not that an extraordinary effort is sufficient to an extraordinary outcome, but it is 100% true that it is necessary. And so I do use that framework as a sort of guiding principle in my own leadership.

Lenny RachitskyTo make this even more real for people, what are examples of moments that were extraordinarily hard?

Matt MacInnisIt is not about any sort of grand single story. I think the story is actually told through a thousand little things. And so for me, the story is told through a thousand Jira tickets, not through a thousand grand events. The extraordinary effort thing is a reminder that it's supposed to be really fricking exhausting. It's supposed to be. So on Friday night, when you get hit with an escalation on Friday night, when you get sort of hit with a bunch of new bugs from someone in the engineering team that you've got a triage, those are the moments where great players and great teams are separated from good players and good teams. And it's so easy to say this at a company like Rippling because we're winning. As a company, for all of our foibles, and we should spend time today talking about where things are not perfect and not great, but the growth rate of the company on the revenue foundation that we have is extraordinary, really, really compelling.

And it gives you, as a leader, the air cover to get up in front of your team and say, "Hey guys, I need the last ounce of oil that you've got left." And if your company's not growing very quickly, if things aren't that great, if your growth rate is 30% or 40%, it doesn't feel as good as a contributor in that business to lean in and give everything you've got on Friday or Saturday or Sunday because you don't know that it's going to yield much. And so extraordinary results, outcomes demand extraordinary efforts, but if there's no chance at an extraordinary outcome, it's very hard to get the extraordinary effort. And so I like to remind people at Rippling at least that it's so rare to have the opportunity to be able to be a part of a team where the extraordinary effort that you do put in on Friday or whatever, whenever it is actually contributing to an extraordinary result.
It's a very special and rare thing, and it gives me a superpower as a leader because I can lean on that when I'm ringing the oil out of somebody who's in the bored and tired zone.

Lenny RachitskyI saw the same thing actually at Airbnb with Brian Chesky. It always felt like things were going great and maybe we could take a break after something we shipped was killing it. And it always felt like the opposite. It always felt like, how do we press the gas pedal further? How do we go faster? How do we go bigger? There's never a moment to take a break.

Matt MacInnisI spent seven years at Apple and learned under Steve Jobs when he was the CEO, learned what we called the death march, which is what we did to the engineers. It was like as soon as you shipped one version of the iPhone, you were just immediately thrown into the pit of building the next one and there was no break. It was just relentless and talk about an extraordinary outcome at the end of the day. There is no relief. In a competitive market, and if the market is valuable, it's competitive, no question. If you leave anything on the field, if you sort of leave a crack for your competitor, 100% chance they're going to go fill that crack. And so you have to be relentless. There can be no relaxation of the organization. It doesn't mean people can't come and go or people can't take vacations or live their lives, of course.

And it's not like people are human beings. You can't grind the individuals down, but the team as a collective group of people has to be sort of on the ball all the time. There can't be a break. And if you leave one, you're just begging for the slightly more hungry competitor to come in and eat your lunch. And that's the beauty of capitalism.

Lenny RachitskyAlso, very counterintuitively, and maybe the more optimistic perspective here is when you do give your team space to just twiddle their thumbs, bad things start to happen. Morale actually dips in my experience. People get distracted. They're like, "Oh, what are we even doing? It's not interesting." I find that keeping people busy and motivated and fired up, even though you may think they'll be happier taking a many week break and slowing things down, I find they get more, the more I actually goes down in those moments.

Matt MacInnisSo here's a management framework that I use fairly often. As an executive, you don't know how to get any decision exactly right. It's not knowable. You don't know how much budget to allocate. You don't know how many people to put on a project. You don't know how to set a deadline for when you're going to ship something. But of course, you have to set some default so you make your best guess and then you manage to that best guess and you learn as you go because in software development and in business in general, everything's emergent. These are not things that are knowable top down or a priority. And so you take a best guess and knowing that you're not going to get the right answer, you need to decide whether over-steering or under-steering relative to your perceived midpoint is better. And so let's talk about staffing. When you staff a project, is it better to overstaff or is it better to under-staff knowing that you can't get it right? Well, it's better to under-staff. If you overstaff, you get everything that you just said. You get politics, you get people working, I think most importantly on things that are further down the priority list than necessary. You have like 20 things on a stack rank list and you know that you got to do the top five, but the next 15 data's kind of ambiguous, but you've overstaffed the project. So the next 10 things down are getting worked on. Before you even know if they're necessary, that is poison. It's wasteful, it slows you down, it creates crust. And so it's very clear that under-staffing is less evil than over-staffing. In this particular framework, the advice is under-staff deliberately, always. And then the wisdom, the wisdom element is to know not to under-under-staff and sort of knowing the difference between those two things.

And so that's the way we work at Rippling. Everyone is constantly asking for more resources and of course where we can afford to and where it's appropriate new resources arrive, but it is really important to me that we feel that we've deliberately understaffed every project at the company.

Lenny RachitskyThere's a previous guest, I forget who this was. They used this metaphor if they want their team to be dehydrated to always be wanting more water. And then eventually they're too dehydrated and okay, we needed someone to help. Interesting. Yeah. There's a line along the lines of extraordinary efforts I want to make sure I read because I think this is really good. This may be a way to summarize what you're saying, that good teams get tired and that's when great teams kick the good team's asses.

Matt MacInnisYes. This was a quote actually from Sunil, and he found it from a women's basketball team coach. And it is, to my point earlier about you got to run the engine at the red line at all times because the minute you let your guard down, the minute you slow down, the minute you relax, the minute you leave a crack for your competition, the great teams are going to come in and kick the good team's. And it's like sports, I'm not a very sporty guy, but sports analogies are sort of irresistible because at the end of the day, business is a game and none of this matters. We're not going to carry it to the grave. It's like you're here to do this stuff because it somehow fulfills you while you're on the planet. And I love the sport of business and I find that sports, notwithstanding the fact that I watched very little of it, that military, those are very ripe sources of parallel concepts to apply in leadership.

Lenny RachitskyI find also those most intense, stressful, long nights are the moments you remember most and remember most fondly back to when you're building something. The key though is that it has to go well. As you said, if you are succeeding and winning, all of this is romantic in the end and nostalgic. Remember that time we built this thing and worked late nights and shipped this thing? If it doesn't go anywhere, you don't feel that. So I think that's a really important component of this is you need to be winning and succeeding.

Matt MacInnisOne thing that I've learned from Parker, Parker's our CEO at Rippling, he said, "You don't really learn from your mistakes, you learn from your successes." And it's like you do, of course, and he would admit you learn a bit from mistakes, but I do think that this is sort of feel good that it's like, "Well, you didn't succeed, but at least you learned something." I've had failures. When I look back at the nine years I spent working on inkling from day one in 2009 until we sold that business to a private equity firm in 2018, up the curve of Silicon Valley coolness, back down the other side into obscurity. Of course, I learned and grew a ton during that time, but in now what I think is six or seven years, I'm trying to do the math, seven years coming up on at Rippling, I've learned so much more because I've seen success.

I've seen rapid, wild, crazy off the charts success of the business and it's more informative. There's more to glean from seeing how it's done right than there is to glean from seeing how it's done wrong. If I tell you you're going to get on an airplane and one maintenance technician has seen it done right a hundred times and the other maintenance technician has seen it done wrong a hundred times, but he learned from his mistakes, but still hasn't had any success himself. I mean, give me a break. There's not even a comparison which plane you're going to feel more comfortable on. And so I do think that learning from your mistakes thing is a bit of a feel good trope that actually has very little substance in reality. And it's why as an early career product manager, or it's why frankly at any stage of your career when you want to learn, you should join a winning team.
It's cool to go and start a company at 22. Good luck to you. The odds are not in your favor, but the folks who, when I look at a resume and I see that someone's joined, they were at really good companies when those companies were super exciting and in crazy growth mode. I'm like, "I instantly want to interview that candidate because I want to hear what they learned from being part of a winning team." And that's sort of one of my go to heuristics when I'm looking at candidate profiles and I think it's an under-told trope. Sorry, not an under-told trope. It's a piece of advice that I don't think people embrace enough in the valley that success begets success and you should chase success.

Lenny RachitskySpeaking of success and learning, you've been a long time COO at Rippling and the reason you're here recently you moved into CPO, chief product officer at Rippling, which is very exciting and very rare. I don't see a lot of COOs moving into product. Let me ask you why did you move into that role? I feel like you've been killing it at COO. Maybe that's the reason. Be careful what you're good at. And also just what are some surprises about this, about moving into product? Because a lot of people imagine what it's like and then you're actually doing it.

Matt MacInnisThe story at Rippling is pretty interesting and I'll tell it because I think it explains why I'm making this transition, but this isn't really about me. I think it's sort of a pattern that your listeners would find useful. In general, your best executives are the ones that you can mostly toss into any challenge and they will bring order to chaos. They will fix the thing. And I do appreciate the terms that people have used at Rippling for me, talking about MacInnis's injured birds, where at any given moment some function is in disarray or in jeopardy and I go and focus very carefully on that function to get it back in order batting 800 maybe, like not always wild success, but I did that everywhere except R&D. I would think about helping out with components of the sales organization like our channel team, or I spent time building out the recruiting function a few times when it needed to be sort of rethought in response to our growth, but it never R&D.

And so I would have my feet up on the table looking out across the floor at this dumpster fire off in the distance, just sort of emitting smoke and wondering if someone was going to go in and deal with that. And the smoke takes various forms and when you're growing as quickly as rippling is growing, it's not always something that necessarily even impacts customers, but it's the sort of thing where you're like, that architecture's not right or they're not measuring adoption correctly." From the outside, I actually had quite a few criticisms that I could lob in. And what happened at Rippling was we made some hiring mistakes. I think the folks that we had in those roles would agree that they weren't the right people. We had a hiring mistake in engineering leadership where the product leader at the time had to sort of run engineering.
We subsequently had a mistake in product hiring and a lot of us had to sort of pitch in. And Parker and I sort of stared at each other through two years of this kind of disarray or this chaos or this agony of things and just never really having good executive leadership over both engineering and product at the same time. And I remember Parker sort of slumped down in his seat and said, "Oh, I have to run another search." And I said, "No, the gig's up. I'm going to go do it." And he really sprung up in his seat. He's like, "Really? You'll go do that?" I'm like, "Dude, this is what the business needs." And so that's what I did. And that really started about a year ago in sort of, I realized I was going to do it and expressed that to Parker in December. I really took it on in January of '25.
And so it's been 11 months of learning. Jumping into the product role when the product function itself, although staffed with really talented people, wildly under understaffed, and without a single spiritual leader on top of it to drive consistency and process excellence had become locally optimized but globally incoherent. And if you know Conway's law, you are destined to ship your org chart. And so with a locally optimized, globally incoherent team, you had a locally optimized, globally incoherent product experience that needed to be resolved. And so my efforts over the last 11 months have been to establish greater clarity in terms of how we do things around here, better process, better general leadership, hiring and firing. I mean, just doing the sort of cleanup on aisle three that needed to be done, even though, again, a lot of the people in the team were quite talented and doing an excellent job of managing their specific domains.
Jumping into the product role has been quite eye-opening. I feel a little bashful about the naivety of my view from the outside a year ago. Product teams have a hierarchy of needs, and we like to point at the failures to meet elements of that hierarchy higher up the triangle and sort of impugn the failure of that organization for not, as an example, measuring adoption metrics very carefully and not closely tracking those metrics as a means by which to drive execution. When I jumped in, I was like, "Man, we need to establish some basic standards for test coverage. We need to establish some basic standards for how we do what I call a factory inspection on a product once it's ready to roll off the assembly line." Do we have a checklist for what we call product quality and what does product quality mean? Those basic things weren't there. And so the idea that we should be spending time measuring adoption metrics is absolute insanity.
You're skipping a lot of steps between here and there. And so we have made great strides and I think it's translating to product quality improvements for our customers, but I feel, as I said, a little dumb for the way I was thinking about it before I jumped into the deep end. There is just no excuse as an executive for sitting outside of the mess and thinking you know the answers. It's a cardinal sin as an executive to do that. You need to go and see. You'd be in the boiler room, you need to study the system, bottom up and develop hypotheses for how to amend the system. And that's what I've been doing.

Lenny RachitskyI love hearing this because so many people have teams that are not functioning incredibly well and hearing from someone that is not a longtime product person come in and try to fix these problems, I think is really useful and interesting for people to hear. To dig into this a little bit more, was the big lesson and kind of eye-opening moment that there's a lot of foundational work that needs to happen to achieve this outcome that you're trying to achieve, which is measure engagement and adoption well? Is it like tracking and metrics and data science? Is that kind of the lesson there?

Matt MacInnisThe lesson is that everything must be done in its time and order, and you can move really, really quickly. There's no sort of excuse not to move with urgency on all of these things, but you got to do them in order and you have to lead bottom up. You got to lead from the specific circumstances you observe. And I think for me, one of the best things that's happened over the last 11 months is that I've gained a greater trust in my own instincts, that sort of patterns I've matched across other functions do indeed apply in product, but I have both the advantage and disadvantage of not having led a product function before and therefore must think about every problem from first principles. I have no choice. I can read shit on the internet. I can listen to clear thinkers on topics and import their ideas, but I'm very reluctant to import an idea without breaking it down into its constituent parts and figuring out how it applies at Rippling.

And so I don't actually give a shit about adoption metrics as a matter of principle. I care about adoption metrics when I care about adoption metrics. I realize that that's a total logical statement, but it's like I'll get there. And so in certain parts of our product, I really do care about adoption metrics. I care a lot about adoption metrics in our applicant tracking system, our recruiting product, because it's in a really good place from a usability standpoint, it's very well instrumented, it's got very happy users, it's got an awesome growth profile, and so we should still ...

Matt MacInnisIt's got an awesome growth profile. So we should be really focused on the adoption metrics because I think that's going to be an important ingredient to low churn over time, removing friction from the implementation process as an example.

There are other parts of our product where I would say I don't care at all about adoption and am much more focused on foundational things like I said earlier, test coverage or whatever, just to make sure that the thing is stable and good and delivering exactly what it's supposed to deliver once it's adopted.

Lenny RachitskyNow that you're on the inside of the product team, what's something that you think people outside of product, say Matt two years ago or other, I don't know, go to market leads, other execs should hear, need to understand about product that they don't until they're on the inside?

Matt MacInnisI'll give you another framework that I like to use. In the financial world, there's this concept of alpha. Alpha is outperformance relative to the index. So that's why you have seekingalpha.com as a very popular website. What they mean by that is you're looking to buy something, some combination of assets that will outperform, let's say the S&P 500, if that's your benchmark. So alpha is the outperformance relative to the index.

And then you have the concept of beta. Beta is just volatility. Beta's not good. A high beta stock jerks around for no particular reason. It's discorrelated with the index. It's very high beta. Great if you're an options trader, but other than that, it's not really something you want in an asset.
So your ideal stock is a very high alpha, very low beta stock. They don't really come in that shape because alpha and beta tend to be correlated, but that's what you want when you buy a financial asset.
So what's the analogy? I think you have high alpha people who are very valuable. I think you also have low beta people who are also very valuable people. Dennis Rodman, basketball player, nut job, very high alpha. And there's room on every team for one Dennis Rodman is a favorite of mine. It's like you can have one difficult employee who's got a ton of upside.
So this alpha beta thing, I use it pretty often when contemplating what kind of person I want and also what kind of process I want. So when you're building a product from zero to one, you're probably pursuing alpha. You're looking for some angle on this market or this customer problem where the product is actually going to provide an outsized return relative to whatever the default solution is. When you have a more mature product or if you have somebody in the product operations group or whatever, you probably want a more low beta environment where it's like it cranks it out, it does it very reliably.
Our payroll product, we badly want the payroll product to be very low beta. We really don't want the payroll product to have any unpredictability or aberration, and so we're willing to accept more process.
And here's a fundamental principle of design in an organization, which is that processes, processes in a business exist for the sole purpose of lowering beta. Processes are for decreasing volatility in the output of the system. The downside of a process is that it suppresses alpha. And you have to be super, super careful and judicious in the application of process and the product team to know that you're lowering beta in the places where you want to do that without suppressing alpha in the places where you need it.
So as we've gone through the last year of reforming the way that we build product at Rippling, it's been a game of recognizing those places where I need to implement a touch of process, just a touch. Other places where I need to implement a very clear, rigid process where I don't want alpha, I just want low beta. So examples of this are let's say our product quality list, which we lovingly at Rippling call the PQL.

Lenny RachitskyWhy PQL?

Matt MacInnisYeah, so it's actually a really important thing. I think if you want to bring about cultural change in a team ... Look, we have 1,300 people in our R&D organization. It's a big ship that we have to steer. If you want to create a moment that sticks in people's brains and sort of becomes a zeitgeist or something that they latch onto, you got to create an entity, a vessel for meaning, and then you got to fill that vessel with your meaning.

Lenny RachitskyA meme, you might say.

Matt MacInnisYeah, well, sure, a meme. A meme is actually a good example of this in common culture. In pop culture. I think it's why, when people come to the table with ideas from the outside, I welcome those outside ideas. But the first thing I ask the person to do is to tell me what they mean without using those words. So when someone comes in and says, "Hey, I want to do this thing on strategy." I'm like, "Cool. Tell me what you mean without using the word strategy." And it forces them to break it down into its constituent parts. And if they can articulate it clearly without using that word, I know that they know what they're talking about. And if they just fumble around with the word strategy again, I'm like, "Okay, you actually haven't thought this through."

So with the PQL, with the product quality list, it's like I could come up with some generic term for this, but I really want a new joiner at the company to understand that this is an idiosyncratic thing to Rippling. This is unique to us. You want to understand this thing. I also want it to become a component of common parlance in the day-to-day work of the product management and engineering teams. So PQL, as cheeky or silly as it sounds, was deliberately sort of angular or stood out as a vessel I could fill with a particular meaning, and so we have a product quality list.
And the product quality list is lightweight in the sense that it just articulates in the simplest ways the standards we want you to meet when you ship a product. It doesn't apply to every product, not every line applies to every product, but it's comprehensive and it provides me with a framework for iterating over time as we learn.
So just yesterday, we shipped the product to Parker. This is part of our process. When we ship a new product, it goes to Parker, who is the big admin for Rippling at Rippling. If you're not aware, Parker is the sole payroll administrator for Rippling for all 5,200 employees. He personally runs payroll always, there is no exception, for all 5,200 people. He does complain about it sometimes, but it's a remarkable achievement for the software and perhaps for him. So he also installs any new app that we're going to install for ourselves because we dog food the hell out of everything we build.
Yesterday, he goes to install this new application. We're about to ship a new app for feedback, allowing people to give one another feedback on their companies. And he installs it and he goes in and it dumps them onto an empty screen. And he's like, "What the fuck is this? What is this? What's going on? Hey, wow, talk about fail." So I chop another one of my fingers off, I'm down to nine. And I'm like, "Well, what did we miss?"
What we missed was there was a fucking feature flag, a fucking feature flag. And I'm not allowed to say feature flag without fucking in front of it because feature flags are the bane of my existence and the worst things in the world that constantly cause problems. Engineers put one in temporarily and forget about it. It's like shims if you're building a house and the general contractor puts little shims in places and then forgets that they put the shims there and then builds a wall over them and eventually the shim fails and all of a sudden your door doesn't fit. Feature flags are super dangerous and need to be managed carefully, so fucking feature flags.
Anyway, we had one. Parker installs it, they forgot to disable the feature flag. He gets a blank screen when he installs the application. What did I do? My reaction was, "Ugh." Go back to the team, give them direct feedback, tell them not to make that mistake again. But also ask the question, "How do we miss this in the factory inspection process?"
And the answer is we didn't have any line item in the PQL for feature flags. So I added a line to the fucking PQL that said, "You are allowed to have one feature flag that governs your entire product at ship." It's an extreme standard that might not be achievable, but it's the standard we aspire to.
This framework, the PQL, given these lightweight checklists, iterated on consistently in response to everything we learn as we go, constitutes a very nice lightweight way to lower the beta of the system with hopefully only a modicum of negative impact on the alpha for how we build product.
You asked me a very simple question, I gave you a very long-winded answer, but these frameworks help me design systems that scale across one going to 2,000 technical workers.

Lenny RachitskyWow. Okay. By the way, PQL, is that like an acronym or it's just like, I like this word we're going to call it PQL?

Matt MacInnisProduct quality list.

Lenny RachitskyOkay, I see. So it's the . Okay.

Matt MacInnisPQL, which how could you pronounce it other than pickle?

Lenny RachitskyI'm imagining all your decks have little PQL emojis and the-

Matt MacInnisThe pickle emoji thing, the dancing pickle in Slack, there's a lot of-

Lenny Rachitsky.

Matt MacInnisYeah. It lends itself to a bit of fun.

Lenny RachitskyWhat I think about is pickle Rick. Do you get that reference?

Matt MacInnisThis is a Rorschach test.

Lenny RachitskyOkay. So this high alpha, low beta, I love this concept. So the idea is depending on the team, depending on the problem, we need a high alpha, low beta person or actually okay with a lot of variants for this specific project that's actually -

Matt MacInnisYeah, we're willing to accept a bunch of volatility in this area in exchange for the upside we get from the creativity and risk taking of these people or the lack of process that sort of gives them the latitude to do what they want to do.

Lenny RachitskySo when you're hiring, you're looking for, again, is this person low beta or not? That's going to -

Matt MacInnisFor sure. It's really quite a useful way. You know when you meet a candidate and you ... My modus operandi, and I think with talk about hiring for a second, I think I've spent a lot of time with teams at Rippling talking about how I hire. And it is born of batting practice. It'd be super interesting to actually be able to rewind the tape on my life and sort of contemplate how many candidates I've met in every context. Many thousands, maybe tens of thousands, I don't know. It's a lot of batting practice and a lot of model training in my brain.

So I rely a lot of my intuition, which of course HR people say you're not supposed to do. That's complete bullshit. If you have a good intuition, you should absolutely rely on your intuition.
And what you have to do after you have a reaction to a candidate when you're looking at hiring somebody is you need to decode your intuition so that it can be expressed to other people productively. So one of the frameworks that I use for this is SPOTAC. It's a very ugly acronym. There's a hat tip to somebody out there in the universe who originally thought of this. It's not me, but I adopted it. And it's that people are smart, passionate, optimistic, tenacious, adaptable, and kind. Those five things. Six, can't even count. I told you I lost a finger when I made a mistake, so I was down one.

Lenny RachitskyNine to go.

Matt MacInnisSPOTAC isn't by itself a good top down framework, but when you're thinking about, "Oh, why did this candidate just ... Why did it not click? Why did I not like them?" You go down the list, you're like, "Oh, yeah, no, this person, it's that they were not excited about the idea. They weren't passionate." It's that they talked shit about their previous manager and that they were a victim of the performance of their last two companies. That's what it was, they're not optimistic.

The framework is super useful to evaluating people. And I think the alpha beta framework is also super useful when you come away from a conversation and you're like, "I like that guy. I think he'd be really, really good. Why is it that I don't think he would do a good job on this product in particular?" And the answer is like, "This is a high alpha product area and he's a low beta person." Valuable, but definitely not the right fit for this. So I think it's really useful in that context as well.

Lenny RachitskyI love all these frameworks. You're speaking to this audience, framework to frameworks, frameworks.

Matt MacInnisYeah.

Lenny RachitskySo high alpha, low beta, sometimes high beta is okay, SPOTAC. In hiring, is there anything else that you find really useful? Before we move on to a different topic.

Matt MacInnisWhen I first started working in the product organization, I was introduced to an interview framework or an interview tactic that I hadn't really used much at all, I think in my career, which is that every product person at every seniority level is given the same case study. And the case study is extraordinarily difficult. It requires you to think about many, many dimensions simultaneously, to think about data propagation issues. It gets quite technical.

And the rubric that we use to sort of evaluate performance of that case study is it gives you guidance on what for us, like an entry level PM looks like, what a junior, mid-career, senior executive PM might look like. And everybody comes away from that interview feeling like poop, like they had failed it. Whereas on our side of it, we're like, "Wow, that person got really far." They saw around three or four corners in a really impressive way. There was 10 they didn't see around, but they saw around four of the hardest ones. And they were not defensive when we gave them new information that called into question the validity of their solution. And they were willing to interrupt us to ask more questions," and and and, like a lot of the sort of basic human interaction models.
You never think that giving someone an impossible task and even including the L5 person versus the VP on the same thing would be productive. And let's just say our recruiting team still sort of kvetches a bit about this and feels like we eliminate people too aggressively at this stage of the interview process. But I've found the wisdom in it and think it's actually quite useful to give everyone the same simple, complicated prompt and just see. Hand them a drill bit, give them the concrete wall and see if they can get a millimeter or an inch into the concrete. They're never going to get all the way through the wall. It doesn't matter. You're going to learn a lot. And I've found that to be kind of an eye-opening new thing for me that has been fun.
Look, the joy of product and the joy of product management and the joy of being part of product, I think there's a bunch of joys actually, if I could give you a sort of running list, but one of the big joys is that you get to work with some of the smartest people in software. Engineers are very smart. They're not always the best sort of social entities. Salespeople are awesome social entities. They're not always the best systems thinkers. You go down the list.
But the magic of product management is that you kind of have to ... We talk about the mini CEO. I think it's kind of a stupid misnomer, but there's some wisdom there. And I think the wisdom is that you have to be a polymath. You've got to be really good at working with other people. You got to be good at communications and articulation. You got to be good at project management. You got to be good at the science and the math and the engineering. And it's really fucking cool. So I think one of the great joys of this job for me has been interacting with the tippity top of the smartest and most polymathic people in the industry.
I'll say one other thing about what I love about leading product, which is as a COO, my job was to accept the product as it was and optimize everything around that. My job was to make sure that the product operations, in our business, the interface to the insurance carriers, the interface to the payment entities, the government regulators, that stuff all just sort of worked. It was to make sure that our sales engine, our marketing engine, all the go to-market stuff optimized itself around what the product was. It was about recruiting and making sure we got people in to work on the product. You kind of go down any function that isn't in R&D, and I had some hand in trying to figure out how to make that function work to the best of its ability, given what the product was.
And now that I lead product, I'm like, "Oh, wow. This is the high order bit." Not that I didn't sort of understand that, but now I really get that product is the high order bit. If you get the product right, it fits in the market, everything else gets easier. Finance is easier, sales is easier, marketing is easier, recruiting is easier, everything gets fucking easier. So I think the other joy of leading the product function is that I get to set the highest order bit in the business's success to one.

Lenny RachitskyThis is really great to hear. A lot of times people outside product don't understand these sorts of things and look down on product a lot of times, especially sales folks, COOs a lot of times. I love that you're seeing this and realizing this and recognizing just how important and interesting and challenging this work is and just how awesome PMs are. As you know, a lot of people are a very anti-product manager. "Why do we need product managers? We don't need them. Slow everything down, all this process."

Matt MacInnisYeah. I have a distinction there, which is that I'm anti-shitty product managers.

Lenny RachitskyThat's exactly how I put it. If you hate product managers, you just haven't worked with a great product manager.

Matt MacInnisWell, it's like, look, I love wine, wine's one of my things. And I've learned a lot about wine. And one of my favorite lines is like, "I don't like Chardonnay." And I'm like, "No, no, no, no, no. Chardonnay's are the most fucking amazing varieties of wine in the world. You just haven't had good Chardonnay. And there's a Chardonnay out there for you." Product management, it's like you don't like product management, you think product managers suck. It's like, well, you just haven't had a good Chardonnay yet.

Lenny RachitskyThat's exactly what I -

Matt MacInnisOnce you have one, you can't unlearn it.

Lenny RachitskyYou're like, "Let's find that PM ASAP."

Matt MacInnisNo, let's find that Chardonnay ASAP.

Lenny Rachitskywith some Chardonnay. You touched on this product market fit point, and I want to double down on this thread. You've had a couple really interesting experiences of struggling to find product market fit with your own startup. You said you worked on it for nine years, you said?

Matt MacInnisMm-hmm.

Lenny RachitskyOkay. And then with Rippling, complete opposite, extreme product market fit, up and to the right. What's something you've learned about just that that you think people maybe don't understand about what it feels like, what it takes to get to product market fit, how things change?

Matt MacInnisThere's a line that this venture capitalist, whose name I will not mention, said, which was that product market fit is a sort of thing where you absolutely know it when you see it, and therefore if you don't absolutely know it, you don't have it.

And this kind of gets back to my point about learning from mistakes versus successes. It's like, ah, man, over and over again, over the course of the many years that I spent at Inkling, we thought we had it. We thought we had product market fit, maybe, maybe. And in hindsight, with the benefit of now having experienced solid product market fit, it was so, so obvious that we didn't.
And I've invested in like 60 companies or 70 companies. I don't know, it's not something I actively do. But opportunities, by virtue, I think, of my role at Rippling, sort of show up. And I talk to lots of entrepreneurs and I love it and I find it super stimulating and I love the fresh ideas and it's just something I do as a real cherry on top of the sport that I play already. But when I get the investor updates for the guys who've been at it for like three, four years and I read the updates from them that I sent to my investors in 2011 and 2012, I'm kind of heartbroken.
We talk in Silicon Valley about never quit, but that is complete absolute venture capital bullshit. The incentive of venture capitalist is to put money into your company and milk you dry. They never get their money back. There is no way for them to take that investment back. So the only logical desire that they would have is for you to keep trying against all odds because there is the occasional example where someone pivoted from A to X and it was wildly different and it worked. Slack was originally some sort of a gaming company and became corporate chat. Airbnb maybe. It's like there's some examples of companies having made wild pivots and succeeded, but man, is that rare. Just so exceedingly rare.
And I think it's important to remember, I'm 45 years old, we're going to be on the planet, the average age of a man in the United States when he dies is something in the mid 70s. I got 20, 30, maybe if I'm lucky, 40 years left on the planet. Very conscious of the time that I have. And I don't regret what I did at Inkling, I learned a lot. It informed what I do now. I don't think the chapter I'm in right now could have come without the chapters before it. So it's a beautiful, wonderful thing that I did what I did. But when I read the investor update and I'm like, "You're where I was and you are not getting out of this."
The Silicon Valley try until you die mindset is not pro-entrepreneur, it's pro-venture capitalist. And I know why that is, but I think it's important to say out loud that you should fucking quit. You should reset the clock, you should reset the cap table because trust me, product market fit when it arrives is insane and it's exciting and you should pursue it. And never delude yourself into believing you have it when you don't. It is dangerous and regrettable. How's that for a speech?

Lenny RachitskyBeautiful. The anti-VC speech. The-

Matt MacInnisI got more where that came from. By the way, it's not anti-VC. It's anti-

Lenny RachitskyVC propaganda.

Matt MacInnisEverybody's acting in accordance with their incentives in Silicon Valley, the executives, the founders, the venture ... Everybody's, of course, behaving in accordance with their incentives. And the venture capitalists have very strong enduring incentives that have shaped the dynamic of how Silicon Valley works. There's nothing wrong with that. It's just really, really important to point them out and scream at them for the 25-year-old entrepreneur who has no fucking clue how this stuff works.

Trust me, the 45-year-old entrepreneur or the 50-year-old venture capitalist who've been in the game for a while, they get it. They've observed it. They know what it's like. The system is there to take advantage of the people who don't, or at least it is the easiest prey for the incentive structures, not for venture capitalists as individual people who are beautiful and all of them are just really wonderful people. It's just that the incentive structures lead to some real harm, I think, in certain cases.

Lenny RachitskyAnd the thing I find is when you do quit, VCs ... I'm always just like, "Hey, let me know when you're starting your next thing. I'm excited to invest." They're rarely, unless they're not a great VC, rarely are they just pissed at you for how could you possibly not make this work .

Matt MacInnisThat's the thing, as a founder, when it's time to throw in the towel on your business and you're so obsessed with giving money back to the cap table, I always remind the entrepreneur like, "Hey, if you're in the seed investing game, your forecast is zero. Your assumption on every investment is that it's going to go to zero." Any seed investor who doesn't take that stance is off their rocker anyway. They're a very bad investor. Seek investors who play the long game, who want to be in your second and third company and are willing to take a bet on the first one and let it go to zero so that you can get on with stuff. This is like, I've had that conversation many times.
Here, look, history provides us with a clear guide. When you look at companies having hit it big, they hit big pretty quick. It's very, very dangerous to be late to the party, it's very, very dangerous to be early to the party, and the vast majority of the time, that's the problem. Rippling, had it been started in 2014, would not be what it is today. I think Rippling, had it been started today, would not be what-
...Not be what it is today. I think Rippling, had it been started today, would not be what it is five years from now today, and so I think timing is a lot and it's very hard to control for, but when you get the timing right and the market is real and the product works, product market fit, like I said earlier, it's super clear, and so if I were to pick a number out of a hat just from my lived experience, I think it's very important, one aside, don't ask people for advice, ask people for relevant experience. If you ask them for advice, they will always give it, but if you ask them for relevant experience, they rarely have any to offer, and if they don't have any to offer, then don't ask for their advice.

So ask people for relevant experience, and I try to do this with my own entrepreneurs when I work with them, it's like, let me offer you whatever relevant experience I have, and my relevant experience on this topic of when to quit is like, I think we could have called it after the second or third pivot, which was somewhere around year four. It is of course very important to believe in what you're building and to be persistent, but there is definitely no shame in saying, "Look, we've pivoted once or twice. It's not catching. I got to go do the next thing," and I think if you're year four, year five in your entrepreneurship journey, and it's not just obviously a screaming rip-roaring growth story, it's extraordinarily difficult. This is so extremely rare. So beyond even already the rare scores you're going to face from the outset that now is going to convert to something crazy. So that's hard to hear, I guess, but man, it can be really liberating when you're like, "Fuck it, I'm going to do this. I have the energy. I'm going to do it again. I'm just going to do it with a clean sheet."

Lenny RachitskyThat is really helpful. You have this really fun way of describing product market fit around receptors and drugs.

Matt MacInnisOh yeah. Yeah. I think this is a really fundamentally misunderstood dynamic. When founders message me and they're like, "Hey, like my LinkedIn post and my tweet for this launch," I do it. I retweet it, I like it, whatever. Nobody follows my Twitter anyways, it doesn't matter, but I do that, but I think to myself, this is not what this is about. This is not how great companies are built. It can be a nucleating event, but it's not a major thing, because nobody cares about your company. Your launch doesn't matter. Big, fat, pull the slingshot back, launches amount to the teeniest thimble of water in the ocean of noise about startups and companies, and so you just got to build it brick by brick bottom up, and these launches don't really amount to much, and so how do you think about that? How do you think about the insignificance of your launch or you think about all the effort you're putting into building a product that you believe is going to have product market fit?

Well, if you recognize that the market is immutable, no amount of tweeting, LinkedIn posting, advertising is going to change whether the market wants your product. It might raise awareness about your product, but it's not going to change whether somebody wants it. Then you take a different mindset. You have to view your startup as running an experiment in the universe to see what you get in return for that, and this analogy of drug discovery and binding receptors is like nobody at Genentech thinks they can market their way to better performance inside your body. The binding receptors for that drug, they exist or they don't, and when they build their product, their goal is to find out whether the binding receptors exist, but fate already has decided the outcome. This is absolutely true of every software product you build. Fate has already decided the outcome. The market's either going to latch onto your product and run with it or it's not. Do not ship the product, find a lack of success, and then try to market your way through that, because the binding receptors likely don't exist, and for me, it was a very liberating mindset, because now I just have to find the right drug, and I can forget trying to convince the body to develop the binding receptors for whatever it is that I'm building.

Lenny RachitskyWhat I love about your advice here is you were an early investor in Notion, which is one of the classic stories of it took them... I think it was four years to get to something. They moved to Japan, they worked on the whole thing, and so is from there? Is that a rare example where it actually worked? And that's not an example to be inspired by, because it's extremely, extremely rare. Let's talk about alpha beta again.

Matt MacInnisOkay. As an investor, you might build a checklist of things you want to make sure are true or false about a company and hope that that's going to yield the kind of investment success you're looking for. Does it have this kind of founder? Is it a C Corp in Delaware? Boom, boom, boom, boom, boom, boom, boom, and these checklists are all about what? They're all about suppressing beta. They're about avoiding avoidable mistakes. They're about bringing stability. Jeff Lewis is an investor who has many angular views on things, and I think one of his most enduring phrases is narrative violations. This idea that the common wisdom must be violated in some way by every company that has an outsized success. It is absolutely true, and when I give these general observations on the patterns in Silicon Valley, the most successful businesses inevitably violate something on that list in some really important way.

So Notion, you can't replicate Notion's success as an entrepreneur. You can't replicate it because you're not Ivan. You can't replicate it because you're not Notion. You can't replicate it because it's not 2010 when they started the company. Do the math on that. Or 2011, actually. These guys stuck with it. They went through hell. They pivoted. They went to Japan and sat in kimonos and meditated on what they were going to build, and by hook/crook, they got to where they are today as a really wildly successful business in an extraordinarily difficult market where building businesses is virtually impossible in productivity. It is dominated by Google and Microsoft. Carving out your own niche in that market is just unthinkable, and so I look at Notion as having succeeded by virtue of the narrative violation of persistence, I don't think is a good idea for very many people that happen to work for them, and I look at it as being a function of the founding team and their specific idiosyncrasies, the absolute insistence on craftsmanship from Ivan. This is him. That's his thing.
The takeaway lesson is not give up or don't give up. The takeaway lesson is certainly not go do what Notion did. The takeaway lesson is that every company succeeds on the foundations of the idiosyncrasies of the founder. The idiosyncrasies of the founder. Rippling succeeds for almost the polar opposite reasons that Notion succeeds, but in both cases, the companies succeed on the idiosyncrasies of the founder, and so embracing that, recognizing those idiosyncrasies, that's what great investors do. They spot that element of spikiness and greatness in a candidate investment, and they convert that to a commitment, and then of course the investor or the good ones accept what they get in exchange from that for the universe, from the universe.

Lenny RachitskyI love that we went in this direction. I wasn't planning to talk about your investing career. Just to give people a reason to listen to this and maybe rewind, and I want to ask another question around investing. What are some other companies you invested in early?

Matt MacInnisFirst of all, okay, so I sort of hate the question. What are some other companies you've invested in? It's a fair question, but the problem is I'm going to give you a bunch of companies I've invested in that won, that are really notable. So what I would like to do instead of answering that question ... Here, let me give you some bait. I was one of the first investors in Notion. I was perhaps the first, I don't know, ask Ivan. Clever, which had a great exit. I was one of the first investors in Zenefits, if you've heard of it.

Lenny RachitskyHeard of it.

Matt MacInnisI was, before I joined, one of the first investors in Rippling, and then more recently invested in ... Here's a funny one. I was one of the first investors in Deal, if you've heard of them.

I was able to exit that position, and then hopefully that company's going to zero with their criminal behavior, but whatever, but more recently, if you know Decagon, which is doing some really cool stuff on the AI front.

Lenny RachitskyKilling it.

Matt MacInnisI'm in laying chain. Great. So those are some companies that you maybe have heard of, but how about I invested in Macro. Founder was Derek Lee. Macro's out of business. I invested in Debrief, Ned Rockson. It's out of business. I invested in Verb Data with David Hertz out of business. I'm reading from a list. I invested in... What's the number? 70 companies according to this list where I track things and most of them went to zero and all those founders were awesome, all those founders were kick, and all those founders put a ton of energy into building their businesses, and they went to zero and they're enduring relationships.

I can call on any of those people, I think, maybe with the exception of Deal, and call in a favor and have... and I've got a few subsequent... and actually a lot of them joined Rippling, believe it or not. So I don't know. Companies I've invested in is a long list, and I love to give you names of companies that don't exist anymore because it's self-serving and a horrible survivorship bias to just list the good ones.

Lenny RachitskyI love that answer. I think you're being modest in the context of your hit rate is clearly very high. Even one or two incredibly successful companies out of 70 is a win in VC, and so you're doing very well, but I think that's a really important perspective. When you see people's logos on their websites of all the companies they've invested in, you have no idea how many hit bats they've had.

Matt MacInnisI think it's good practice to ask people to give you the full list. Yeah.

Lenny RachitskyWhat are your favorite failures that you've invested in?

Matt MacInnisOh, no. I'm not actually... Okay.

Lenny RachitskyWell, obviously, no, we don't need spend time on it, but I think it's actually a really good question, but yeah, what are some of your best failed investments? Show me the logos of the companies that didn't work out.

Matt MacInnisIt's a juicy question. Yeah.

Lenny RachitskyThere's a topic around this area that I wanted to spend time on, and I haven't heard anyone think of things this way, which is this idea you talk about of compounding plus power law plus entropy and how that's a really useful frame to think about business.

Matt MacInnisSo you kicked this conversation off sort of invoking the extraordinary outcomes, demand, extraordinary efforts line, hat tip to Dan Gill, and these are part and parcel. Man, understanding the nature of the universe is a pretty good way to work within it, and so power law distributions happen everywhere. It explains why so few people control so much wealth. It explains why Steph Curry is just so vastly better than the next guy down on the list on the basketball team. It explains why populations are concentrated into a relatively small number of mega cities in the world. It's like, power law distribution just plays out everywhere, and once you see it, you can't unsee it. It sort of plays out in many dynamics.

People tend to think that the world plays on a more linear relationship where the X and Y axis are sort of Y equals X, but that is absolutely not the case, and the implications are profound. It's like if you build something to 80 or 90%, the Y axis is barely budged yet. You haven't hit the inflection point in terms of reward, and so the implication of the power law more broadly is that people who are in the top 10%, the top 5%, don't just get 10 or 20% more reward. They get 10X the reward or 100X the reward. It's really dramatic.
Entropy, the second law of thermodynamics is a very simple concept. It's the reason your sock drawer becomes messy. It's the reason that potholes form. It's the reason we have to put so much energy into maintaining the aircraft we fly to keep them safe because they really, really, really want to fall apart, and that's the nature of things. If you abandon a city for a few months, it starts to go fallow, and so entropy is just this concept that shit tends toward disorder.
The universe, I mean, life itself is a temporary victory against entropy. You and I should not exist. The sun gives energy to the planet. It organizes stuff that we can eat and we fight entropy until we lose the battle somewhere, as I said earlier at the age of 70 or 80, if we're lucky. What does this have to do with product? This is really about effort.
The only antidote to entropy, the only antidote to decay in a system is energy. You got to inject energy. So if you have a code base, every line of code that you add to that code base increases the entropy of that system and demands ever more energy from human beings to go and intend to it to make sure it doesn't break, and if you want to achieve greatness, if you want an extraordinary outcome, and in particular, if you want to be in the top 10%, top 5% on the X axis so that the Y axis is through the roof, then you have to relentlessly inject energy at every single step of the game. Teams will, sadly, but because we are all human, teams will always optimize for local comfort over company outcomes.
Not because they get together and think, "We should do that," although unions do do that unequivocally, deliberately, but even in a collection of product managers or engineers, what's going to happen over time is entropy is going to creep in and people are going to optimize for local comfort. Your job as an executive, as a leader, is to fight that entropy tooth and nail every single day. It means that every time you see a bug, every time you see a bug, not most of the time, every time you go and you drop it at the feet of the product manager or the engineering manager, every time, in public, preferably, it means that every time someone comes to you to hire someone and says that they have skipped the back channel, every time you're like, "You can't hire this person unless you do the back channel," it means that when you get into the board and tired zone on any process, that you as the executive have got to demand the 99th percentile of energy, because otherwise entropy creeps in and the system decays. You have to do this.
One of the messages that I delivered recently at our big executive big... Like our top 75 manager offsite that we do roughly every 18 months, was a reminder that if the purest form of ambition and the purest and most intense source of energy in the business is the founder CEO, that every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity, and that is dangerous because if you go to two layers and it's two orders of magnitude drop off and signal and intensity, that is a very dysfunctional organization. So what I say to the team was, it's not that you need to buffer people from the intensity of the CEO, it's that you need to absolutely mirror that intensity.
There are plenty of constituents in the business around you who will advocate for relaxing. There is an infinite supply of people under you who will buffer other team members from the intensity of the demands. Your job is not to be one of those buffers. Your job is to preserve that intensity at its highest possible level and let the buffering happen somewhere else, and that's the point is that entropy creeps into the system insidiously and slowly over time off your radar and you have to maintain that intensity every minute of every day to try and fight it if you want to stay at the extreme right end of the power law that obviously governs the outcome of everything that we build.

Lenny RachitskyWhat does that look like to pass along that intensity? What does that feel like? What does that look like? So say Parker comes to you, "This bug sucks. I got this broken screen." You cut off your finger. Maybe that's the example.

Okay. Still got them. I got all 10.

Matt MacInnisI'll give you concrete examples. Actually, the joke that I sort of played on this one when I presented to the team was that the next sort of slide in my presentation was with the sound effect, the Slack huddle thing, and Parker's icon in Slack is just, he uses the generic yellow...

Lenny RachitskyThe egg?

Matt MacInnisYeah.

Lenny RachitskyOh, wow.

Matt MacInnisIt's funny, and so everybody knows the yellow egg is Parker, and so the next slide in the presentation was boop, boop, boop, boop, boop, boop, boop, which is the sound that Slack makes when someone calls you, and it was Parker Conrad is inviting you to a huddle, and then the next slide was Parker Conrad is modeling personal intensity, and the idea is that if you know, you know, if you've ever been dragged into an... "I want to talk about this fucking problem right now and whatever you're doing, unless it's an interview, I want you to come and have a conversation with me."

That intensity is one place where it plays out. Every product team at Rippling, and we have a lot of them now, have public feedback channels. I am in there upside down on everything I find when I use those products, and I just model for everybody that this is how at least I want to do it, which is, "I don't like this. I don't understand this. Tell me why this is this way." Boom, boom, boom, boom, boom, and people jump in and respond. The factory inspection process that I mentioned, which is where at the end of the assembly line, I jump out with the pickle and we talk about all of the elements. You have to record a loom of every major flow through the product. I personally review every one of those flows, I got a backlog I got to catch up on today and provide feedback to people always in a public channel so that every other product manager and engineering manager can jump in and see how the process has worked for other teams.
It's about modeling the intensity publicly so that other people can say, "Okay, this is how we do things around here," and it gives the reaction from the team that received the message that you have to inject that energy every minute of every day and that there are no exceptions, was not like, "Ooh, that's exhausting." The reaction is, "Oh, that is so invigorating." It's so wonderful to hear that we're going to achieve these great outcomes, or at least we have a shot at doing so, and that you're empowering me to follow my instinct, which is to really push for the best result.
The reaction universally is like, "Ugh, what a relief that I get to go be intense," because nobody in a position of leadership wants to be chill, and what's worse than a chill boss? No, don't work for a chill boss. Don't be a chill boss. It's the most pejorative label I could give you. Chill boss or chill PM. Don't be chill. Chill doesn't accomplish shit. Be intense. Be good, be respectful, be intense. Don't be chill.

Lenny RachitskyAgain, this advice comes from where we started, which is this is what success looks like, because somebody that is less chill than you is going to find that crack and come after your market. Is that the gist?

Matt MacInnisFor sure. I mean, again, if you're chill and you move the X axis down 10 or 20 points, the Y axis collapses. It doesn't just drop 10 or 20%. The Y axis collapses, and this is just kind of true in everything we do. So yeah, if you want to win, you should probably try.

Lenny RachitskyThis is what I always say to people trying to build lifestyle businesses. There's always this idea, "I'm going to build a side business, I'm going to make recurring income, it's going to be amazing," and in my experience, anytime there's a market or something shows up that's juicy and there's ways to make money, somebody's going to come at you and work harder, raise more money, and there's only so long you can maintain that.

Matt MacInnisWell, man, there's a whole other podcast episode on the concept of leverage. If you sell your time, you've only got 24 hours a day to give, but if you can create a product that scales, the marginal cost of a unit of that product is zero like software, it's going to be competitive, man. Sell your time, it's not going to be super competitive, but achieve that level of leverage and it's a pretty efficient market.

Lenny RachitskyTo close out this thread of intensity and adding energy to everything, something I've heard about you is you're big on escalating. You're a big fan of escalating issues, and also you always tell people to never not give you negative feedback, to always share feedback to not hide anything. Tell me about those two.

Matt MacInnisFundamentally, the most selfish thing you can do is withhold feedback from someone. Who are you optimizing for when you do that? What are you optimizing for when you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable? Well, you're optimizing for your own comfort and it's fundamentally selfish. It's the most selfish thing you could possibly do, is withhold feedback that would otherwise be useful to someone because you don't want to be uncomfortable. Well, that's not how high performance teams operate. So I demand feedback, and I give it, and it doesn't mean that when I give feedback, it's not open to being questioned or discussed. I mean, of course it is, but when I observe something, I try to say it. That's the feedback topic.

The part of this that has been interesting to me is that people withhold, escalate, the customers withhold. Customers don't want to escalate to me as an executive. Even the founders in whose businesses I've invested who use Rippling are reluctant to hit me up when something goes wrong because they don't want to bother me, but it's literally my job, literally my job to find things, problems, and make them better, and by virtue of making those specific things better, to iterate on the processes so that the system that builds the system can get better.
There's no greater gift to me as a product executive than receiving an escalation from a customer. We have an escalations team at Rippling, which sounds weird, but it's people who are just particularly skilled at pistol whipping other people in the company to get to real root causes, real root causes. Not like throw away the word root cause, like, "Oh, we fixed the data error and shut the ticket down." No, you went and you found the software that created the data error, and then you found the system that created the software that created the data error, and you solved all of that back to the top.
Escalation seems extremely good at that at Rippling. So we have sort of a dedicated little team that does this for us. Escalations are a gift, and it's like, if you're a listener right now on this podcast and you are a Rippling customer and you have shit that you think we should know, the fact that I might already know it is not a reason for you to withhold the gift of your feedback. So it's an attitude that I take to this every day. I've got a little cue of some stuff that I've... Minor things that are from the last couple of days from people who had some knits and issues that I'm just like, I've got them queued up on my to do list today and I'm going to take them to the product teams directly and be like, "I'd like to understand what happened here." Not in a negative way. I just think we'll all get better if we study this one, and so yeah, escalations are a gift, feedback like that is a gift, and nobody is ever inconveniencing me when they do it.

Lenny RachitskyFor people that are listening to this and feeling like, "Man, this is so stressful and intense and just like, I don't know if I want to work this way," give them a sense of just how successful Rippling is. I think a lot of people may not even have heard of Rippling. A lot of people are like, "Yeah, it's doing great." What are some things you can share that are public or not public that give people a sense of just how massive this business has become?

Matt MacInnisPeople look at Rippling from the outside, I think they think of us as payroll and HR or whatever, which is cool. It's a bit like saying Microsoft is a desktop operating system company or it's like every company starts from somewhere.
... system company or ... It's like every company starts from somewhere and grows out from there. We see ourselves as building the most successful business software platform in history. In fact, that's the mission statement of our product organization under the umbrella of the mission statement of the company, which is to free smart people to work on hard problems. And when you translate that from where we are today to where we think we're taking things, it's like we really do believe that the core of every workflow and everything that a company has to do, be it AI or manual traditional GUI based software, is who's doing stuff, who owns it, who's accountable? And so the people record is a really important component of that. You can argue that the customer record's also very important. And of course some big businesses have been built on that primitive as well, but we think the people primitive is actually much more important.

And that the only thing that hasn't been done here is somebody hasn't been ambitious enough to build a good business on top of that primitive. Workday is terrible software. Everybody agrees on that. I think Workday agrees on that. Good luck to them. But they have failed actually, despite their success, to build a really broad general purpose software platform for business software on the foundation of the people primitive. So we're going to do that.
And we're successful because we deliver on that promise at the scale we're at today. The fact that you can do ... and this is not a sales pitch or sort of like an advertisement for Rippling. I just think it's important to sort of contemplate that when you bring together a bunch of disparate business processes into one system on a common business data graph, an object graph, a data lake with a consistent interface, you can do some pretty magical things.
So we do payroll, we do HCM, we do IT, we do spend. We are about to launch a new product in the category of business intelligence and data management. And there's a whole bunch of other stuff coming beyond that. And then you layer in AI on top of this, where we alone, where we alone have all of your business data organized into this nice, neat package with a beautiful semantic layer on top of it. The AI can work magic. And we have shipped nothing, nothing yet in this category that I would say gets anywhere near what we're going to show next year. And it is going to set the standard. It is going to be the most ... The back flips that the AI is doing reading and writing data for the user just on our internal use cases at Rippling is jaw dropping. So I'm super excited about the tailwind this is going to create for us.
You ask about what can I share about the success of the company? What I can say, there are tens of thousands of companies that now run on Rippling. We're less than 1% of the market. And the market cap at 16 billion, I think now undervalues where we are from a revenue perspective by a long shot. There is just so much upside to do what we're doing. And SaaS might be dead-ish in terms of point solutions, but long live SaaS in terms of what we're building.

Lenny RachitskyLet me follow that thread in AI. There's been a lot of talk about AI is going to replace SaaS, as you maybe just said.

Matt MacInnisYeah. People are going to vibe code their way to their payroll system, which I ... good luck to the employees of those companies.

Lenny RachitskyAnd so what I'm hearing here is that you actually do believe a lot of SaaS companies that are selling individual solutions are in big trouble. The answer implied here is this kind of compound startup idea of you need to do a lot of things for people for them to continue to pay for your software. Is that the gist?

Matt MacInnisNo. I think the gist is ... there's a really good quote. I forget who it's attributable to, but it's, "There's two ways to make money in software, bundling and unbundling." And you just got to get the timing right. So this is a period of bundling. So here's the problem; point solutions don't have enough data in the age of AI to be useful. You got to be able to provide the AI with a lot of context about a lot of data so it can do things. It can do joins. It can do correlations.

And so if you're a point solution, you're in hard water because you've got to now rely on data from other sources. You've got to integrate to third party systems. And when you integrate to a third party system, even the best ones are still sort of drinking their data through a straw, which is a real problem. I mean, the biggest HCM software company you can think of integrates to the other biggest payroll software company you can think of through flat files via SFTP. What are they going to do? What are they going to do? It's just never going to work. It's just no way. And so I literally have no idea what they're going to do. They're just not going to build AI software, I guess. Point SaaS is sort of in a rough spot, especially when you cleave two really important systems apart and say they have to integrate. It's very, very hard.
The other thing that I would say about the world of, even just like not SaaS, but AI software is that point solutions in the AI world are also in a rough spot for the same reason. It's like if you're selling the shovels like OpenAI and Google with Gemini, you can make money. And if you own the mine, like Rippling, with the data, you can make money. If you're somewhere in the middle, building AI software that then tries to use the shovels from the shovel provider, but then also needs to rent out the mine, or get the ore out of somebody else's mind and start refining it, you're in a very difficult place from an economic standpoint. Because you're not going to be permitted by either of those parties to build a big business on their backs.
That's just not how it's going to work. They're going to demand value capture that crushes your unit economics. So I look at the landscape of AI companies that I've seen and I think you have to have a really durable, interesting insight that gives you a shot at viable unit economics to be an interesting business. And that is going to kill off 80 or 90% of the stuff that I see right now as standalone AI businesses.

Lenny RachitskySo what I'm hearing here ... I love that you correct me when I get these things wrong, and that's exactly what I want. What I'm hearing is it's less about how difficult it is to build the SaaS product. It's about, do you have first party data that allows you to build an incredible AI product on top of what you've got?

Matt MacInnisYep. Because look, SaaS software is a bit flipping. All SaaS software applications are bit flippers. It's an interface changing-

Lenny RachitskyYour database?

Matt MacInnisYeah. Changing values in your database, that's what it does. It's a really hard problem. One of Rippling's superpowers is we're a coin sorter. You dump $20,000 for an employee in the top of the coin sorter, and it figures out what goes to the government, what goes to health insurance, what goes to your 401k, what goes to you. And it has to move all that money very, very reliably and seamlessly, very challenging software to build and manage. What's it doing? Even that is just flipping bits in a database. And so AI is a new way to flip bits. AI is just a new way to flip bits. Hopefully a way that abstracts us a little bit further from having to think because our future is Wally. It's going to be great.

Lenny RachitskySpeaking of Wally, actually, I have this Matic Robot. You have one of these?

Matt MacInnisUh-huh.

Lenny RachitskyNo. It's like a self-driving car robot, basically, a self-driving car. People built this robot that cleans your house. Maybe I didn't mention that. It's like a house cleaning robot that just goes around.

Matt MacInnisOh, okay.

Lenny RachitskyIt's like a Roomba. You should have one. They're expensive, but incredibly cool. And actually in Wally, there's a scene where they actually have basically what these things look like. So it's not so far-fetched for that movie.

Matt MacInnisI definitely was actually quite prescient, perhaps with the exception of the gravity defying day beds.

Lenny RachitskyYeah. I don't know, but that's not good news. You've seen that movie. Oh, man. So on this AI stuff, which I'm hearing is we're going to see a lot more consolidation where these point solution companies realize they need this data. This is existential, and they're going to combine and merge and bundle, as you described?

Matt MacInnisIt's possible.

Lenny RachitskyOr for now.

Matt MacInnisI am not an investigator on this stuff. I think there's some really interesting investors out there who I think are thinking quite deeply about this. And in particular, the conviction, which is like Mike Fornell and Sarah Guo. I think those are two investors who are hyper focused on AI. And when they made the decision to take that approach, at the time I thought that's kind of narrow. Now I'm like, no, no, no, that was the right move. And it just means that they have a very deep, deep, deep set of hypotheses that they've formed over the course of seeing every AI deal in the valley. And there are better people to ask this question of than I am. And I think if you're an entrepreneur, I recommend them to you because I think they're really smart.

Lenny RachitskyAwesome. I love those guys. Also, Sarah and Elad have a podcast called No Priors that I'd also recommend. We'll point it to you in the show notes. So on this AI note, I guess is there anything else that you think would be really helpful for founders that are working in this space building an AI startup to hear they think you were seeing of like, here's what you need to do to win in an AI company?

Matt MacInnisSo much. I actually think that if I were to give you an answer to this question right now, it would be bullshit. Yeah. I don't have anything ... Back to my point earlier, I don't have enough relevant experience in the abstract to dole out on a podcast on that topic, but I wish them luck.

Lenny RachitskyI love that. Circling back to your advice, don't ask for advice, ask for a relevant experience. And I love that that's where your mind immediately went. I'm going to take us to AI Quarter, which is a recurring segment on this podcast. And the question is just what's one way you've found AI to be useful in your work day-to-day? Is there something that you found it unlocked in how you work?

Matt MacInnisI mean, it's not a super exciting thing, but I'll say where I use ... So one of the most important functions that I perform as an executive is the synthesis of ideas, and the ability to communicate those ideas very clearly to people. So when I talk about the product quality list and the pickle, as something that we've come up with internally, I do turn to AI, ChatGPT and Gemini, where I take a really, let's say, angular view of some topic and I give ... really, I write the essay for the AI and I'm like, "Look, this is the crisp idea I want to communicate. Help me come up with pithy ways to articulate these things." And 80% of what it outputs is trash. It's just sort of middle of the road, average, low alpha junk.

But it is a thought partner, a non-judgemental thought partner where in 20% of the stuff it comes out with, I'm like, yeah, it's pretty good. That's a new word I didn't think of. That does kind of hit the nail on the head for this concept. And so if I believe that my job is to sort of bring brains along on the journey for some sort of change that I'm trying to bring about, then the most important tool is language. And I do find that the ChatGPT and Gemini do a great job of helping me refine how to articulate the concepts that I want to articulate. They are not useful in coming up with the ideas themselves.

Lenny RachitskyThat's an awesome tip. I don't know if you've played with Claude much, but I actually find Claude is better at writing and words and language.

Matt MacInnisI have not spent a lot of time with Claude. I have used it, but by virtue of this conversation, I'll probably go give it a go.

Lenny RachitskyRight. Yeah. They're all great, but there's something about Claude that is just at writing specifically is much better, but they're all getting better all the time. There's always something new.

Matt, we've covered so much ground. We've touched on everything I was hoping to touch on. Before we get to our very exciting lightning round, is there anything else that you were hoping to share or anything else you wanted to touch on or leave listeners with?

Matt MacInnisYeah. We've spent a lot of time talking about intensity and the grind, and the need to just always be operating at the 99th percentile. And I think if you listen to that in a vacuum, it's very easy to believe that that intensity is soul crushing, that it's a negative, that it's maybe not something that you want. And I think there's a backstop for me that I didn't talk about today that I think is important to share, which is that life is amazing. That the fact that we all exist on this blue marble drifting through space and time, that we are some weird instantiation of consciousness, each of us, and that you're here for such a short period of time whittling your stick, doing something, that if you remember how insignificant we are and all of this is, it brings this levity to what we do and to the work we put into building this.

Because Silicon Valley in 2025 is Florence and the Renaissance. It's crazy. The amount of creativity and insane invention and progress that's happening for our species right now in this place is absolutely unparalleled in all human history. You've got to zoom out and appreciate that magic. And so then you turn around and you're like, fuck, I've got to work on Friday night, right? I've got to go give it my all. I've got to go compete in the arena of business.
You have to never forget that number one, none of this matters. And number two, it is an absolutely beautiful and amazing phenomenon that we get to be alive doing this right now. So play the sport, play it with everything you've got, but never forget that it's just a sport and that none of it matters. I think it's super important as a counterpoint to the intensity that we talked about.

Lenny RachitskyThat is beautiful.

Matt MacInnisI think about Pale Blue Dot, Carl Sagan's whole thing. Just a stunning photograph that literally changed the way I think about who I am as a person when I saw it. Yeah.

Lenny RachitskyWell, going in a completely different direction, with that, Matt, we reached our very exciting lighting round.

Matt MacInnisOkay.

Lenny RachitskyAll right, five questions for you. Are you ready?

Matt MacInnisOkay.

Lenny RachitskyHere we go. What are two or three books that you find yourself recommending most to other people?

Matt MacInnisOkay. Two or three books. You give me a heads-up on this. So one book is Conscious Business. I don't have Conscious Business in front of me because it's actually at the office because we have Conscious Business Reading Club at Rippling. And every member of my current, my product leadership team is going through this right now, Conscious Business, Fred Kofman. It's been used in many businesses, LinkedIn most notably, as a framework for thinking about ... effectively, it's a user manual for human beings. So if you are a leader, a manager, an executive, whatever, particularly younger people in their 20s and 30s who are just sort of getting the hang of being a CEO or a product leader for the first time, this book is absolute fucking gold. It was recommended to me by Bryan Schreier at Sequoia when he was on my board at my previous company. I took way too long to take him up on the advice, wished I had read it sooner. Highly recommend Conscious Business. Changes your life.

Number two, Thinking in Systems, Donna Meadows. I always mispronounce her name, Donella Meadows. She died partway through writing this manuscript. Her fellow professors picked it up and finished it for her. It is the best generic framework for thinking about how systems work. You will extrapolate from this book to every aspect of your life after you read it.
And then the third is classic 1960s, The Effective Executive. It's an anachronism. It uses weird pronouns for the secretary and the executive. I'll let you guess which ones. But the book itself is so chock-full of simple enduring advice on how to be effective at leading teams. And the good shit is the stuff that's been in print for 70 years, and that's one of them.

Lenny RachitskyBeautiful. I love the first one is you don't have it because you're using it with your team constantly. You mentioned at one point before we started recording, you have eight copies of that book that you just give out to everyone.

Matt MacInnisYeah, and we handed out like candy.

Lenny RachitskyOkay. Is there a favorite recent movie or TV show you've really enjoyed?

Matt MacInnisYeah. So I'm a little embarrassed by this answer, but I'm going to be honest.

Lenny RachitskyPlease.

Matt MacInnisThere's a new series called Heated Rivalry and it's about ... I'm Canadian and I'm gay. So it's about two hockey players. In Canada, rivals between the Bruins and the Maple Leafs, although they don't use those names, who are just heated rivals on the ice. And it's a huge thing that the world is watching, but actually they're secretly in love with each other and they start hooking up. And it's been labeled by the media as smutty but delightful. And I would say that's accurate. So it might not be for everybody, but it is a smash hit right now. It's on HBO Max and Crave, and it's only six episodes. But like I said, a little embarrassing because it's a little chintzy, but it's a lot of fun. It's also really fun to see gay people represented in the media as though they're normal, and it's fun.

Lenny RachitskyAnd soon to be on Netflix with the acquisition if that goes through.

Matt MacInnisOh, yeah.

Lenny RachitskyIt's crazy. Amazing. Okay. Is there a favorite product you recently discovered that you really love?

Matt MacInnisMy Fellow coffee maker. I love my Fellow coffee maker. It's got an interface that lets you set light, medium, dark roast. It changes the temperature. It blooms the coffee. It tells you how many grams of coffee to put into the basket, slick interface, high quality coffee. It's definitely awesome. And so I have Ashley have one in the office and one at home and one in the garage.

Lenny RachitskyWow. That is a favorite product. You have three of them in the same cool space.

Matt MacInnisYeah.

Lenny RachitskyOh no, in the office. Okay.

Matt MacInnisFellow is also a Rippling customer and that's a nice side effect when we get to ...

Lenny RachitskyHave they ever escalated anything to you?

Matt MacInnisNo. If you're listening and you're from Fellow, I want to hear all your gripes.

Lenny RachitskyPerfect. Two more questions. Do you have a favorite life motto that you find yourself coming back to often in work or in life?

Matt MacInnisIt's a dark one, and I'll share this one sort of partially for the humor of it, but it's actually sometimes useful immediately. At least it's sort of a moment of smiling when it happens. The motto comes from my dad who said, "Matt, nothing's ever so bad in life that it couldn't get worse." And it's like we were going through some shit yesterday at work and we were like, "Fuck, now that happened." And I looked at the CTO and I'm like, "Dude, nothing's ever so bad that it couldn't get worse." And we had a good laugh and continued to brace for whatever might come next. So not exactly uplifting, but fun to use.

Lenny RachitskyNo, it is uplifting. I'm an optimist and I find myself thinking that often with my wife just like, "It could be worse. It could be worse than this. " Definitely. It's actually .

Matt MacInnisAnd it might get there.

Lenny RachitskySo let's enjoy this less worse version. Final question. Something you shared with me is that you were a DJ when you were a younger person. Can you just give us a little DJ voice to give people a sense of your skills?

Matt MacInnisWell, so first of all, it's not DJ, Lenny. It's radio personality. And yeah, I used to do the greatest hits of all time with hits from the '60s, the '70s, the '80s, and a little bit of the '90s, 101.5 The Hawk. Yeah. You can turn it on. It's very inauthentic, but it sounds good on the radio. It's cool. I did it when I was in high school. I ended up doing the midday segment right before I went to college. And what a gift. What a huge gift in my most formative years to have developed an ability to be in front of a microphone comfortably, because here we are.

Lenny RachitskyI love for people that weren't watching this YouTube, you lean really close to the mic to get that radio personality voice.

Matt MacInnisYeah, you got to be able to hear the saliva in the mouth.

Lenny RachitskyIncredible, and it's like the same person talking. If you're not watching this, you're like, "Where did that guy come from?" That was great. You nailed it. Matt, this was incredible. I really appreciate being here. I really appreciate you sharing all this advice that I have not heard other people share. Two final questions. Is there something you want to plug, point people to, and how can listeners be useful to you?

Matt MacInnisLook, my life is rippling. I point people there, and this is my life's work. It's going to be a banger, so stay tuned. And the way that you can help me is that if you're a customer, you got to tell me when you have problems, because that's how we get better.

Lenny RachitskyWhat's the way to get to you? Is there any place you want to point people to?

Matt MacInnisDM me on Twitter, is easy @stanine. You can email me my last name at rippling.com, and I'll go that far without giving out my phone number. How's that? Perfect.

Lenny RachitskyA perfect boundary.

Matt MacInnisYeah.

Lenny RachitskyMatt, thank you so much for being here.

Matt MacInnisIt's my pleasure. Thank you for having me, Lenny, and congrats on all the success with this podcast. It's been great.

Lenny RachitskySame to you. It's always a good sign at the end of a conversation when you're like, oh, I got to get me some of that stock and I got to get into that Rippling.

Matt MacInnisIt's a good buy.

Lenny RachitskyA great job.

Matt MacInnisRecommended by-

Lenny Rachitsky15 billion.

Matt MacInnisYeah, but you're

Lenny RachitskyYou're hard to get All right, man. Thank you so much.

Matt MacInnisThanks.

Lenny RachitskyThank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

Matt MacInnis对我来说非常重要的一点是：公司里的每个项目都应该是“有意地人手偏紧”。项目一旦超配，就会出现政治、出现优先级靠后的事情被提前做，这会变成毒药。它浪费资源、拖慢速度，还会制造大量冗余。

Lenny Rachitsky你在 Rippling 做了很长时间 COO，最近转任 CPO（首席产品官）。你经常讲一句话：卓越结果需要卓越投入。

Matt MacInnis如果你想拿到 99 分位的结果，这一定会很难。你得不断提醒团队：如果你在工作中感觉“很舒适”，那大概率你做错了。它本来就应该很他妈累。

Lenny Rachitsky你也是“问题升级（escalation）”的支持者。

Matt MacInnis本质上，最自私的行为就是你明明有能帮助别人进步的反馈，却因为怕尴尬不说。那是在优化你自己的舒适，不是在为团队负责。很多团队效率不高，就是因为大家会优先局部舒适，而不是公司结果。企业里最纯粹的野心和最强能量源头永远是创始 CEO。每往外一层管理圈，都可能出现一个数量级的强度衰减，这非常危险。领导者的职责就是尽可能守住这股强度。

你自己也经历过创业起伏。硅谷常说“永不放弃”，但那套话很多时候就是纯 VC 叙事。

Lenny Rachitsky今天的嘉宾是 Matt MacInnis，Rippling 现任 CPO、前 COO。Rippling 估值超过 160 亿美元，员工超 5000 人，Matt 是关键推动者。他有一个很罕见的组合：极度坦诚、实战经验很深、还能把经验讲得非常清晰。今天有很多观点，我以前在节目里几乎没听别人讲过。

感谢 Albert Scrashim 和 Sunil Raman 提供问题建议。如果你喜欢这档播客，欢迎订阅。
（产品 pass 与赞助口播已省略）
Matt，欢迎来到节目。先从你很在意的主题开始：卓越结果需要卓越投入。为什么这件事这么关键？
Matt MacInnis :
这句话最早来自我朋友 Dan Gill（Carvana CPO）。我今天很多观点也不只针对产品，而是管理本身：CPO 和其他 CXO 的底层职责其实很像，都是让一群人用共同框架达成目标。
其中一个最普遍但常被忽略的事实是：如果你真想做成 99 分位的事，它一定困难、一定不舒服。卓越投入不是卓越结果的充分条件，但几乎是必要条件。

Lenny Rachitsky能不能举些“真正很难”的时刻？

Matt MacInnis :
不是某一个宏大时刻，而是成千上万个小时刻。故事不写在“大事件”里，而是写在上千个 Jira ticket 里。
所谓卓越投入，就是你要接受“这本来就会很累”。周五晚上被 escalation 砸到、临时出现一批 bug 需要你接住，这些才是好团队和伟大团队分野的地方。
在 Rippling 讲这话相对容易，因为公司在赢。增长和体量都很强，这给领导者很大“喊话权”——我可以正当地对团队说：“我需要你把最后一滴油都榨出来。”
如果公司只长 30% 或 40%，让贡献者在周末持续透支就很难有说服力，因为他们不确定付出是否真有结果。卓越投入需要卓越目标来承接。
所以我会提醒团队：能在“高投入真能转化为高结果”的环境里工作，是很稀缺的机会。对领导者来说，这是巨大杠杆。

Lenny Rachitsky我在 Airbnb 也有类似感受：越是赢，越不会松油门，反而会想怎么再快一点、再大一点。

Matt MacInnis :
我在 Apple 跟 Steve Jobs 学到过“死亡行军”节奏：一个版本刚发完，立刻进入下一版。几乎没有“放松窗口”。
在竞争市场里你只要留一条缝，竞争对手就会填上。团队可以轮休、个人可以休假，但组织整体不能松。否则就是把饭碗主动递出去。

Lenny Rachitsky还有个反直觉点：让团队“太闲”反而士气会掉。人会分心、会迷茫，甚至觉得“我们到底在做什么”。

Matt MacInnis完全同意。

Matt MacInnis我常用一个管理框架。作为高管，你不可能把每个决策都调到“绝对正确”。预算该给多少、人手该配多少、什么时候发版，这些都不可能事先精确知道。你只能先给出一个默认值，基于当下最佳判断去管理，然后边做边学。因为软件开发和商业本身就是涌现式的，不是那种能自上而下算清楚的系统。

所以既然你注定不可能一次调准，就要想清楚：相对你心里的“中位点”，是宁可往上偏一点，还是宁可往下偏一点。拿 staffing 来说，项目配人时，到底是过配更好，还是欠配更好？我的答案是：宁可欠配。
如果你过配，就会出现刚才说的那些问题：政治、低优先级工作被提前做掉。你的优先级列表里明明只有前 5 件事是确定必须做的，后 15 件其实都还模糊，但因为人太多了，团队就会自然把第 6 到第 15 件也一起做掉。你甚至都还没确认那些事有没有必要，这就是毒药。它浪费、拖慢，还会制造系统里的脏东西和历史包袱。
所以在这个框架里，欠配的代价明显小于过配。我的建议是：要有意识地长期欠配。但这里的智慧在于，你不能“欠配过头”。要分清“有意偏紧”和“已经荒唐不够”之间的边界。
Rippling 就是这样运作的。每个人永远都在申请更多资源。只要公司负担得起、也确实合理，资源当然会补进来。但对我来说很重要的是：公司里的每个项目，都要让人清楚感受到，我们是有意把人配得偏紧的。

Lenny Rachitsky我记得之前有位嘉宾打过一个比喻：他希望团队始终有点“缺水”，总觉得还想多来一点水，直到真的脱水得太厉害了，再补人。还有一句跟“卓越投入”很相关的话，我想念出来，因为我觉得特别好。它某种程度上很像你刚才说的：好团队会累，而伟大团队就是在这个时刻狠狠干翻好团队。

Matt MacInnis对，这句话其实是 Sunil 给我的，他是从一位女子篮球教练那里看到的。它和我前面说的是一回事：你必须让引擎始终跑在红线附近。因为你只要一放松、一减速、一松懈、给竞争对手留条缝，伟大团队就会冲进来狠狠干翻好团队。

商业和体育很像。我其实不是特别运动型的人，但体育类比总是很难抗拒，因为商业本质上也是一场游戏。说到底，这些东西你也带不进坟墓。你之所以做，是因为它在你活着的时候给你某种满足感。我很喜欢商业这项运动，而体育、军事，哪怕我自己看的不多，都是领导力里非常丰富的平行参照。

Lenny Rachitsky我也发现，那些最紧张、最漫长、最累的夜晚，反而是你最容易记住、甚至后来最怀念的时刻。前提当然是最后得赢。像你说的，如果你一直在成功、一直在赢，回头看这些时刻就会很浪漫、很值得回味。要是最后什么都没成，那感觉就完全不一样。所以关键条件还是：你得赢。

Matt MacInnisParker，也就是 Rippling 的 CEO，给过我一句很重要的话：你并不是真的从错误中学得最多，你更多是从成功中学习。

当然了，你肯定也会从错误里学一点，但我一直觉得“虽然没成功，但至少学到了东西”这句话，多少有点自我安慰。我当然也失败过。回头看我从 2009 年创办 Inkling 到 2018 年卖给 PE 的那 9 年，我当然成长了很多，也学到了很多。但我在 Rippling 这快 7 年里学到的更多，因为我看到了真正的大成功，极速、疯狂、超出图表的成功。
看到事情被正确做成，能学到的东西，远比看它怎么被做错要多得多。就像如果你要上飞机，一个维修员看过 100 次正确做法，另一个看过 100 次错误做法，还说“我从错误里学到了很多”，你会选谁？这根本不是一个级别的比较。
所以我觉得“从错误中学习最多”这件事，很多时候是一种很让人感觉良好的套话，现实里没那么成立。对于职业早期的 PM，或者任何阶段想快速学习的人，我的建议都一样：去加入一个正在赢的团队。
22 岁就创业当然很酷，祝你好运，但概率并不站在你这边。相反，当我看简历时，如果看到一个人在公司最有势能、最兴奋、增长最疯狂的时候待过那家公司，我会立刻想面他，因为我想知道：你在一个真正会赢的团队里学到了什么。
这几乎是我看候选人的一个核心启发式。硅谷对这件事强调得还远远不够：成功会催生下一次成功，你应该主动去追逐成功。

Lenny Rachitsky说到成功和学习，你之前长期是 Rippling 的 COO，现在转成了 CPO，这很少见。我几乎没见过多少 COO 直接转产品。为什么会做这个转变？以及，真的跳进产品之后，有什么和你原来想象不一样？

Matt MacInnisRippling 这件事挺有代表性的，所以我讲讲。它不只是关于我个人，我觉得对听众也有参考价值。通常来说，最强的高管，是那种你把他扔到任何混乱里，他都能把秩序带回来的人。在 Rippling 里，有人半开玩笑地把这些事叫作 “MacInnis 的伤鸟”。

意思是：公司任何时候总会有某个职能失序、出问题、快掉地上了，我就会过去盯住它，把它拉回正轨。成功率大概八成吧，也不是每次都神迹。但我几乎什么都做过，除了 R&D。
我以前会坐在外面，看着远处 R&D 那团不断冒烟的“垃圾火”。那烟有很多形式。像 Rippling 这种增长速度下，问题不一定已经伤到客户，但你会明显感觉到：架构不对、adoption 没量准、很多事情不对劲。从外部看，我其实有一堆批评可以扔进去。
后来我们在工程管理和产品管理上都踩了 hiring 的坑，负责的人自己大概也会承认，他们不是最合适的人选。然后 Parker 和我就这样看着这团混乱持续了两年：工程和产品始终没能同时拥有成熟的高层领导。
我记得有次 Parker 瘫在椅子里说：“唉，我还得再跑一轮 search。”我说：“别找了，到此为止，我去做。”他一下坐直了，说：“真的？你要去接？”我说：“这就是公司现在最需要的事。”
我大概是在 2024 年 12 月明确跟他提的，真正全面接手是在 2025 年 1 月。到现在差不多 11 个月，一直在边做边学。
我跳进去的时候，产品团队里有很多很有才华的人，但整个组织严重缺编，而且缺少一个真正能统一精神、统一流程、统一标准的人。结果就是：局部都优化得还行，整体却非常不连贯。按 Conway 定律，你最终会把组织结构原样发成产品。于是团队是“局部最优、整体失序”，产品体验也变成“局部最优、整体失序”。
过去 11 个月，我做的大量事情，其实就是“3 号通道清场”：建立更清晰的做事方式、更好的流程、更稳定的领导方式、该招的招、该换的换。很多人自己管的模块其实做得不错，但组织层面缺了“整体操作系统”。
真正跳进产品后，最让我吃惊的是：我之前站在外面看问题，真的太天真了。产品团队也有自己的需求层级。站在外面的人很容易盯着金字塔高层，比如“为什么 adoption metrics 没量好”“为什么没用那些指标去驱动执行”。但我一进去就发现，我们连更底层的东西都没立住。
比如：测试覆盖率有没有基本标准？产品“出厂前检查”有没有 checklist？到底什么叫产品质量？这些最基础的东西都还没建立好。在这种状态下，还谈什么 adoption metrics？那简直是疯了。

Matt MacInnis你要从这里走到“精细度量 adoption”，中间还隔着很多台阶。过去这些月我们确实进步很大，我觉得客户已经能感受到产品质量在改善。但老实说，我现在回头看自己跳进来之前的想法，会觉得有点蠢。

作为高管，最不可原谅的事之一，就是站在混乱外面，觉得自己已经知道答案了。你必须走进去，得下到 boiler room 里，得从底层把系统看清楚，再形成你要怎么修这个系统的假设。我过去 11 个月基本都在做这件事。

Lenny Rachitsky我特别喜欢你这么讲。很多团队现在的产品组织并没有运转得很好，听一个并非长期产品背景的人跳进去修这些问题，我觉得很有价值。那是不是说，这次最大的顿悟就是：为了实现“更好地量 engagement / adoption”这种目标，前面其实有一大堆更基础的工作必须先做？

Matt MacInnis核心教训是：所有事情都必须按自己的顺序发生。你当然可以很快地做，但不能乱序做；你必须从底层往上带，必须从你亲眼看到的具体情况出发。

过去 11 个月对我帮助最大的一件事，是我更相信自己的直觉了。我发现自己在别的职能里匹配出来的很多模式，在产品里一样成立。只不过我以前没真正领导过产品，所以我不得不从第一性原理重新思考每个问题。这反而既是劣势，也是优势。
我不在原则层面崇拜 adoption metrics。我只会在“该关心 adoption metrics 的地方”关心它们。听起来像废话，但意思是：我会到那个阶段，只是不是一上来就到。
比如我们的 ATS（招聘产品），我就非常在意 adoption metrics。因为它已经很好用了、埋点也全、用户反馈好、增长也强。到了这个阶段，当然应该盯 adoption，因为那会直接关系到长期低 churn，以及能不能把实施过程里的摩擦继续打掉。

Matt MacInnis但也有另一些产品，我现在完全不在乎 adoption。我更关心的是更基础的东西，比如测试覆盖率。先确保这个产品稳定、可靠，并且一旦被用户采用，它就能准确交付自己该交付的价值。

Lenny Rachitsky你现在站在产品团队内部了。那有没有什么是“团队外的人两年前的 Matt 也不懂、直到真的跳进去才明白”的？

Matt MacInnis我再给你一个框架。金融里有个概念叫 alpha。Alpha 是相对指数的超额收益，比如你跑赢标普 500，那就是 alpha。

还有一个词叫 beta。Beta 说的是波动性。高 beta 股票没有明确原因地乱跳，和指数脱钩。如果你不是做期权交易的，大多数时候你不会想要一个高 beta 资产。
所以理想资产是：高 alpha、低 beta。当然现实里二者常常相关，但大家都想要这种组合。
放到组织里也一样。有些人是高 alpha，他们非常有价值；有些人是低 beta，他们也很有价值。比如 Dennis Rodman 就是典型高 alpha，挺疯，但极有上限。每个团队可能都能容纳一个这样的人。
这个 alpha / beta 框架，我既用来看“该招什么样的人”，也用来看“该设计什么样的流程”。做一个 0 到 1 的产品时，你大概率追求的是 alpha：找到一个能显著跑赢默认解法的角度。产品成熟之后，你反而会想要低 beta，让系统稳定、持续、可靠地产出。
比如我们的 payroll 产品，我们就极度希望它是低 beta。我们不想它有任何不可预测性，所以愿意接受更多流程。
而组织设计里一个很重要的原理是：流程存在的唯一目的，就是降低 beta。流程本质上是在降低系统输出的波动性。但流程的代价，是它会压制 alpha。
所以你必须极其小心：在哪些地方你是为了降低 beta 而加流程，哪些地方你又不能因为流程太多把 alpha 给压没了。过去一年我们在改 Rippling 的产品构建方式，本质上就是在不停判断：这里要不要加一点流程？那里是不是必须用很强、很明确的流程？比如我们的产品质量清单，也就是 PQL。

Lenny Rachitsky为什么叫 PQL？

Matt MacInnis这其实很重要。如果你想在一个大团队里推动文化变化，你不能只讲抽象理念。我们 R&D 有 1300 人，是艘很大的船。你得造一个“承载意义的容器”，然后再把你要的意义灌进去。

Lenny Rachitsky也就是某种 meme？

Matt MacInnis对，某种意义上就是 meme。其实我欢迎别人带外部概念进来，但我第一反应总是：你先别用这个词，换一套词给我解释一遍。比如你说“strategy”，那你不用 strategy 这个词，重新讲一遍你到底什么意思。如果讲不清，那说明你自己也没想明白。

PQL 也是一样。我要让新加入的人明白：这是 Rippling 自己的一套东西，你得理解它。我要让它变成产品和工程团队日常语言的一部分。所以我故意给它起了一个有点棱角、容易记住的名字，让它变成一个我可以装进特定含义的容器。
所谓 product quality list，本质上是一个轻量清单，用最简单的话说明：发一个产品时，我们希望你达到什么标准。不是每条都适用于每个产品，但它足够完整，而且会随着我们持续学习而不断迭代。
就像昨天，我们又发了一个产品给 Parker 体验。Rippling 有个流程：新产品先给 Parker，因为 Parker 自己就是 Rippling 的超级管理员。顺便说一句，他亲自给 Rippling 5200 名员工跑 payroll，这是真的，没有例外。他偶尔会抱怨，但这既说明软件强，也说明他挺强。
昨天他装一个新应用，是我们准备上的 feedback 产品，让同事之间互相反馈。结果一进去，直接是空白页。他当场就炸了：“这他妈什么鬼？”于是我心里又觉得自己少了一根手指，只剩九根了，然后开始追：我们到底漏了什么？
最后发现，是一个该死的 feature flag。对我来说，feature flag 前面必须加“该死的”，因为它们就是我最讨厌的东西之一。工程师临时放一个，回头忘了关，就像装修时垫进去的小楔子，后来墙都封上了，小楔子出问题，门就合不上了。feature flag 非常危险，必须严管。
这次就是这样：Parker 安装产品，团队忘了把那个 feature flag 关掉，于是直接白屏。我第一反应当然是：回去狠狠干反馈，让团队别再犯。但更重要的问题是：为什么这个问题没在 factory inspection 里被挡住？
答案很简单：因为我们的 PQL 里根本没有 feature flag 这一项。所以我就在那份该死的 PQL 里新加了一条：产品发版时，最多只允许有一个控制全局的 feature flag。这个标准可能很激进，甚至暂时做不到，但它是我们明确想追求的标准。
像 PQL 这种轻量清单，随着每次学习持续迭代，就是一种很好的方式：在尽量不伤害 alpha 的前提下，把系统的 beta 慢慢降下来。

Matt MacInnis你问了个很简单的问题，我却讲得特别长。不过这些框架确实是我拿来设计系统的工具，能帮助我把一套机制从 1 个技术员工一路扩到 2000 个技术员工。

Lenny Rachitsky太强了。顺便问一句，PQL 真的是缩写，还是你单纯觉得这个词挺顺口？

Matt MacInnis就是 Product Quality List。

Lenny Rachitsky懂了。

Matt MacInnisPQL 这个词，不念成 pickle 都很难吧。

Lenny Rachitsky我已经开始脑补你们所有 deck 里都有各种 PQL 小表情了。

Matt MacInnis对，腌黄瓜 emoji、Slack 里跳舞的 pickle，已经玩出很多梗了。

Lenny Rachitsky我第一个想到的是 Pickle Rick，你懂这个梗吗？

Matt MacInnis这都快变成罗夏测试了。

Lenny Rachitsky好，那回到刚才那个 high alpha、low beta。我太喜欢这个框架了。也就是说，得看团队、看问题本身。有些场景你就需要低 beta 的人，有些场景反而接受更大的波动，对吗？

Matt MacInnis对。有些区域我们愿意接受更多波动，因为这些人的创造力、冒险精神，或者说流程少一点带来的自由度，能换来更大的上行。

Lenny Rachitsky所以你在招人时，也会判断这个人到底偏 low beta 还是 high alpha，对吧？

Matt MacInnis当然，这个框架非常有用。说到招聘，我在 Rippling 花了很多时间和团队讲我是怎么招人的。坦白讲，这套方法本质上就是大量“打击练习”练出来的。如果能把我人生里的面试录像倒带统计一下，我见过的候选人可能有几千，也可能上万。那就是大量样本在我脑子里做模型训练。

所以我很依赖直觉。HR 往往会说你不该这么做，我觉得那完全是胡扯。前提是，如果你的直觉已经被足够多样本训练过，你就应该用它。
但关键在于：你不能只有直觉。你对一个候选人有了第一反应之后，得把这份直觉拆解出来，变成别人也能理解、也能讨论的语言。我常用的一个框架叫 SPOTAC，缩写很丑，不是我原创的，但我拿来用了。意思是：Smart、Passionate、Optimistic、Tenacious、Adaptable、Kind。

Lenny Rachitsky还剩九根手指可以数。

Matt MacInnisSPOTAC 不是一个自上而下就完美的框架，但当你在想：“为什么这个候选人没让我产生感觉？为什么就是没点上？”时，它特别有用。你顺着这几个维度过一遍，往往就明白了。比如：哦，不是他不聪明，而是他对这件事根本不兴奋，不够 passionate。或者他说起前老板全是抱怨，把自己描述成前两家公司表现不佳的受害者，那问题可能就是他不够 optimistic。

这个框架非常适合评估人。alpha / beta 也一样。当你聊完一个人，会觉得“我挺喜欢他，也觉得他会很强，但为什么总觉得他不适合这个具体产品？”这时候你就可能发现：这个产品领域需要 high alpha，而他是个 low beta 的人。不是他没价值，而是这次不匹配。

Lenny Rachitsky我太喜欢这些框架了。你今天真是框架套框架，完全对这档播客听众的胃口。

Matt MacInnis对。

Lenny Rachitsky所以现在我们有 high alpha / low beta，也有 SPOTAC。招聘这件事上，还有没有别的你觉得特别有用的东西？

Matt MacInnis我刚开始接手产品组织时，接触到一个以前几乎没怎么用过的面试方式：不管资历高低，所有产品候选人都做同一道 case。这个 case 非常难，要同时考虑很多维度，还会牵涉数据传播之类的问题，技术味也挺重。

我们有一套 rubric 来评估表现，里面会定义：在我们这里，初级 PM 会做到什么程度，中级、高级、执行层 PM 又会做到什么程度。几乎每个候选人做完都觉得自己被打爆了，像是彻底失败。但站在我们这边看，会觉得：“哇，这个人已经走得很远了。”也许前面有 10 个弯他没看到，但最难的 3 到 4 个弯，他真的看到了。而且当我们给他新信息、去挑战他原来的解法时，他没有防御性，还会主动打断我们继续追问。很多最基本的人和人互动能力，其实都会在这种 case 里暴露出来。
你直觉上会觉得，把一个根本做不完的题丢给所有人，甚至让 L5 和 VP 做同一题，应该不会太合理。我们的招聘团队直到现在也还会吐槽，说这一关刷人太猛了。但我越来越觉得，这里面是有智慧的。你给每个人同一个“简单但极其复杂”的 prompt，然后就看他能往里钻多深。
你就像递给他一根钻头，再给他一堵混凝土墙，看他到底能钻进去 1 毫米还是 1 英寸。他不可能钻穿整堵墙，这根本不重要。重要的是，你会从这个过程里学到非常多。这对我来说也是最近一个挺开眼的收获。
再说回产品这份工作的乐趣。其实乐趣很多，但其中一个最大的乐趣是：你可以和软件行业里最聪明的一批人一起工作。工程师非常聪明，但未必最擅长社交；销售很擅长社交，但未必是最强的系统思考者。每个职能都有自己的偏向。
而产品管理的迷人之处在于，它逼着你变成一个杂家。大家老说 PM 是 mini CEO，这个说法虽然有点俗，但里面确实有一点道理。你得会和人协作、得会沟通表达、得会项目管理，也得懂科学、数学、工程。说真的，这很酷。对我来说，接手产品之后最大的快乐之一，就是能跟行业里最顶尖、最全能的一群人高强度共事。
还有一点，是我作为 COO 和作为产品负责人最大的感受差异。以前当 COO，我的工作是接受“产品已经是这样了”，然后围绕这个既定产品，把周边一切都优化好。我要确保产品运营能跑起来，确保和保险公司、支付机构、政府监管之间的接口都运转正常；还要让销售、市场和整个 GTM 体系去适配这个产品；还要把人招进来继续做它。基本上，除了 R&D 之外的大多数职能，我都在想：在产品既定的前提下，怎么把它们调到最好。
但现在我接手产品之后，才真正体会到：哦，这才是最高位的那个 bit。不是说我以前不知道产品重要，而是现在我真的切身体会到，产品就是那个最高位。如果产品做对了、和市场贴上了，后面所有事都会变容易。财务更容易，销售更容易，市场更容易，招聘更容易，一切都会容易得多。
所以，领导产品这件事最让我兴奋的另一点，就是我终于能亲手去把公司成功里最上层、最关键的那个 bit 设成 1。

Lenny Rachitsky听你这么说真的很好。很多不在产品里的人其实并不理解这些，甚至会看低产品，尤其销售、COO 这类角色常常会这样。我很喜欢你现在从内部看到了这份工作的难度、重要性和吸引力，也看到了优秀 PM 到底有多强。你也知道，现在有一派人非常反 PM，会说“为什么需要 PM”“PM 只会拖慢一切、制造流程”。

Matt MacInnis我的区分是：我反对的是烂 PM，不是 PM 这个角色本身。

Lenny Rachitsky我也是这么说的。如果你讨厌 PM，大概率只是你没跟真正优秀的 PM 合作过。

Matt MacInnis就像我很喜欢葡萄酒。有人会说“我不喜欢霞多丽”。我就会说，不不不，不是霞多丽不行，霞多丽是世界上最棒的葡萄品种之一，只是你还没喝到好的霞多丽，总有一款是适合你的。

产品管理也一样。你不是讨厌产品管理，你只是还没遇到一位“好的霞多丽”。

Lenny Rachitsky太对了。

Matt MacInnis一旦你遇到一次，你就回不去了。

Lenny Rachitsky你就会想，赶紧帮我找这样的 PM。

Matt MacInnis不，是赶紧给我找那瓶霞多丽。

Lenny Rachitsky边喝霞多丽边继续聊。你刚才提到 product-market fit，我想顺着这条线深挖一下。你自己的创业公司在 PMF 上挣扎了很多年，你说你做了九年，对吧？

Matt MacInnis嗯。

Lenny Rachitsky然后到了 Rippling，完全相反，几乎是极强的 PMF，一路向上。关于这件事，你觉得大家最容易误解什么？不管是 PMF 的体感、代价，还是一旦进入 PMF 后整个状态会怎么变。

Matt MacInnis有位我就不点名的 VC 说过一句话：product-market fit 这种东西，如果你真的看到了，你会百分之百知道；反过来，如果你没有百分之百确定，那你大概率就还没有。

这其实又回到我前面说的“成功比失败更能教会你东西”。在 Inkling 的很多年里，我们一次又一次以为自己“可能有 PMF 了，差不多了吧”。但现在回头看，在真正体验过强 PMF 之后，就会发现：当时没有，就是没有，而且其实明显得不能再明显。

Matt MacInnis我大概投了 60 家，或者 70 家公司吧，我也没认真数过。这不是我刻意去做的事，只是因为我在 Rippling 这个位置上，机会会自己找上门来。我会和很多创业者聊天，我很喜欢这个过程，很受刺激，也喜欢那些新鲜想法。对我来说，这更像是我已经在打的这场“商业之赛”上的额外奖励。

但有时候，当我看到一些已经做了三四年的创业者发来的 investor update，再对照我自己 2011、2012 年发给投资人的那些更新，我心里其实挺难受的。
硅谷常说“永远别放弃”，但那很多时候就是彻头彻尾的 VC 话术。VC 的激励机制很简单：钱一旦投进去了，就拿不回来了。他没有办法把那笔投资撤回。所以从纯理性上说，他们唯一合理的期待，就是你无论如何都继续试下去。因为偶尔确实会有那种从 A 硬拐到 X、而且居然真成了的故事。Slack 一开始是做游戏的，后来变成企业聊天；Airbnb 某种程度上也算。这样的例子当然存在，但实在太罕见了，罕见到几乎不该拿来做默认建议。
我今年 45 岁。按美国男性平均寿命算，人一般也就活到七十几。我可能还剩 20 年、30 年，运气好也许 40 年。我对时间这件事是非常有感知的。
我不后悔当年做 Inkling，那段经历让我学到很多，也塑造了我现在的做事方式。我今天所处的这一章，不可能脱离前面那些章节单独出现。所以它当然是美好的、值得的。但当我看到一些创业者的 investor update，我会想：你现在正站在我当年站过的位置上，而你其实很难从这里走出来。
硅谷那种“试到死为止”的心态，并不是站在创业者一边，而是站在 VC 一边。我知道它为什么会这样，所以我反而觉得，必须把另一句话大声说出来：你应该果断停下来。
你应该重置时钟，重置 cap table。因为请相信我，product-market fit 一旦真的来了，那种感觉是疯狂的、兴奋的，你会知道它值得追。真正危险的，是在没有 PMF 的时候骗自己说“已经有了”。那会让你在错误的路上消耗太久，而且回头看往往很后悔。

Lenny Rachitsky太精彩了。这简直是一段“反 VC”演讲。

Matt MacInnis我还能继续讲。不过严格说，这不是反 VC。

Lenny Rachitsky是反 VC 宣传。

Matt MacInnis对。硅谷里每个人都在按照自己的激励做事。高管、创始人、VC，所有人都是。VC 拥有一套非常强、而且长期稳定的激励机制，这套机制塑造了硅谷今天的运作方式。这里面没什么“道德错误”，但关键是你得把这些激励明确指出来，尤其要讲给那个 25 岁、还完全不知道这套系统怎么运转的创业者听。

相信我，45 岁的创业者、50 岁的投资人，已经在牌桌上待得够久了，他们都明白。真正容易被这套系统拿捏的，是那些还不懂的人。不是说 VC 个人有什么问题，很多人都很好。问题在于，激励结构本身在某些情况下确实会造成伤害。

Lenny Rachitsky而且我发现，真到你决定停下来时，大多数 VC 的反应其实是：“等你做下一个项目时告诉我，我还想投。”除非他本来就不是个好 VC，一般不会真因为你没把这家公司做成就跟你翻脸。

Matt MacInnis对，作为创始人，当你准备给一家公司收摊时，往往会特别执着于“我要把钱还给 cap table 里的人”。但我总会提醒创业者：种子投资这件事，它的默认预期本来就是归零。任何 seed investor 如果不是这么看的，那他本身就不适合做种子投资。

你应该去找那种愿意陪你打长期关系的投资人。第一家公司归零也没关系，他们更在乎你第二家公司、第三家公司还愿不愿意让他们上车。我已经和很多创业者聊过这件事了。

Lenny Rachitsky（GoFundMe Giving Funds 赞助口播已省略）

那问题就来了：到底什么时候该停？如果有人听到这里会想，“糟了，那我是不是也该结束了”，你会怎么看？有哪些信号说明，差不多该收了？

Matt MacInnis历史其实给过我们很清楚的参考。你去看那些最后真正做大的公司，它们通常都是比较快就显出势头的。太晚进场很危险，太早进场也很危险，而绝大多数时候，问题就在这里。

如果 Rippling 是 2014 年开始做的，它今天不会是现在这个样子；如果 Rippling 是今天才开始做，五年后大概率也不会成为今天这样的 Rippling。时机这件事非常关键，但又很难控制。可一旦时机对了、市场真实存在、产品也真有效，那 product-market fit 就会像我前面说的那样，非常清楚。
如果非要我根据自己的经历拍个数字，我会先插一句：不要问别人“建议”，要问别人“有没有相关经历”。你一旦开口问建议，别人总能给你一堆；但你要是问相关经历，很多人其实根本没有。如果他没有相关经历，那就别太把他的建议当回事。
所以回到“什么时候该停”这个问题，我能提供的相关经历是：以我自己的项目来看，我觉得我们在第二次或第三次 pivot 时，大概也就是第 4 年左右，就已经可以停了。
当然，相信你做的东西、保持韧性，依然很重要。但完全没必要把“坚持”神化。你 pivot 过一两次，还是没接住，完全可以坦然地说：“行，这个没接住，我该去做下一件事了。”
如果你已经在创业第 4 年、第 5 年了，业务依旧不是那种明显到刺眼的高速增长故事，那它真的会非常难。你原本就已经在打一场极低概率的仗，这时再指望它突然变成疯狂增长，概率只会更低。听起来可能刺耳，但当你终于说出“算了，我重新来一张白纸”时，那种感觉反而会很解放。

Lenny Rachitsky这真的很有帮助。你讲 product-market fit 还有一个特别形象的比喻，是“药物和受体”。

Matt MacInnis对，我觉得大家对这件事的误解非常深。经常有创始人会来找我说：“帮我转发一下这次上线的 LinkedIn 帖子和推文。”我会转、会点，但心里其实在想：这根本不是重点。伟大公司不是这么建出来的。

发射式的大规模上线，顶多能算一个点火事件，但绝不是决定性因素。说白了，没几个人真的在乎你的公司。你的 launch 没那么重要。你以为自己拉满弓、用尽全力做了一次发布，但它丢进创业世界的噪音海洋里，可能连一小勺水都算不上。
所以你只能一块砖一块砖地往上砌。那些上线动作本身，实际意义往往没那么大。那该怎么理解这件事？
如果你承认“市场是不可被你意志改变的”，那你就会换一种心态。你发多少推、写多少 LinkedIn、砸多少广告，都改变不了市场到底想不想要你的产品。它们顶多提升认知，改变不了需求本身。
你应该把创业理解成：你在这个宇宙里做一次实验，然后看宇宙回给你什么。
我那个“药物和受体”的比喻，就是说，没有哪个药厂会觉得自己能靠营销让药在你身体里表现更好。一个药能不能和受体结合，这件事本来就存在，或者不存在。他们做药的目标，是去验证这些受体到底在不在，而不是靠宣传让身体临时长出受体来。
软件产品也是一样。命运其实早就决定好了结果。市场要么会抓住你的产品一路往前跑，要么不会。你不能在产品推出、反应平平之后，再试图靠营销把这件事“推出来”。如果没反应，大概率是那个“受体”根本不存在。
对我来说，这个心态反而特别解放。因为我只需要继续寻找那种“能和市场结合”的药，而不用再浪费时间去试图说服这个身体，为我临时长出本不存在的受体。

Matt MacInnis好，我们再从投资人的视角说。作为投资人，你很容易做出一张 checklist，试图确认一家公司身上哪些条件是真、哪些是假，然后期待这套清单能带来你想要的投资回报。比如：创始人是不是某种类型？是不是 Delaware 的 C Corp？一项一项往下打勾。

但这些清单本质上是在干什么？它们都在压制 beta。都在避免那些“本可以避免的错误”，都在追求稳定性。
Jeff Lewis 这个投资人有个我很喜欢的说法，叫 narrative violations，也就是：真正能做出巨大成功的公司，一定会在某个关键点上违背主流叙事。这个判断我觉得完全成立。你去看硅谷最成功的公司，它们几乎都会在那套“常识清单”里，狠狠违反其中一条非常重要的规则。
拿 Notion 来说，你作为创业者没法复制 Notion。你复制不了，是因为你不是 Ivan；也不是 Notion；也不是 2010 或 2011 年那个时间点。你算一下就知道了。
他们一路撑下来，吃了很多苦，pivot 过，甚至跑去日本，穿着和服冥想自己到底要做什么。结果硬是做成了一家极其成功的公司，而且还是在一个非常难打的市场里。生产力软件这个赛道几乎不可能做出大公司，因为 Google 和 Microsoft 早就把大盘压得很死了。你想从这个市场里硬切出一块地盘，本来几乎不可想象。
所以我看 Notion 的成功，核心不是“坚持”这个词本身有多伟大，而是他们恰好用“坚持”这种 narrative violation 打穿了一条路。但我不认为这对大多数人都是好建议。它之所以对他们有效，更多是因为 founding team 自身非常独特，尤其是 Ivan 对 craftsmanship 的绝对执念。这是他的个性，也是这家公司成立的底层原因。
所以真正的 takeaway 不是“该放弃”还是“不该放弃”，更不是“去照着 Notion 那样做”。真正的 takeaway 是：每家公司最后成功，都是建立在创始人的那些独特性上。
是创始人的 idiosyncrasies 决定了公司怎么赢。
Rippling 成功的方式，几乎和 Notion 是两极相反的。但两家公司有一个共同点：它们都赢在创始人极其鲜明的个人特质上。真正优秀的投资人，就是能看见这种尖锐、突出、甚至有点异质的地方，然后基于它下注。至于最后宇宙回给你什么结果，好的投资人也会接受。

Lenny Rachitsky我很喜欢我们竟然聊到了这里。我本来没打算聊你的投资经历，但我还想顺着再问一个投资相关问题。你还早期投过哪些公司？

Matt MacInnis首先，我其实有点讨厌这个问题。不是说它不合理，而是因为一旦我回答，几乎注定只会列出那些“赢了”的公司，也就是你听过、也很显眼的那些。

那我不如这样回答。先给你一点“钩子”：我很早就投了 Notion，甚至可能是最早的投资人之一；Clever 也投过，后来 exit 很好；Zenefits 早期我也投了。

Lenny Rachitsky听过。

Matt MacInnis在我加入之前，我也是 Rippling 最早一批投资人之一。再近一点，比如 Deal，如果你知道这家公司，我也很早投过。

后来我退出了那个仓位，而且以他们现在那种近乎犯罪的做法来看，我甚至希望它最后归零。先不说这个。再近一些，像 Decagon，这家公司在 AI 方向上做得很有意思。

Lenny Rachitsky很猛。

Matt MacInnis对，挺好的。所以我当然可以列出这些你听过的名字。

但我更想告诉你另一组名字：我投过 Macro，创始人是 Derek Lee，已经关掉了；投过 Debrief，Ned Rockson 做的，也关掉了；投过 Verb Data，David Hertz 做的，也关掉了。我现在是照着列表念。
按我这边的记录，我一共投了大概 70 家公司，其中大多数都归零了。可那些创始人都很棒，真的都很能打，也都投入了大量精力。只是最后公司还是归零了。但这些关系没有归零。
我现在基本上还能给这些人里任何一个打电话，可能 Deal 除外。很多人后来甚至还加入了 Rippling。对我来说，“我投过哪些公司”其实是一张很长的名单。而且我更愿意讲那些已经不存在的公司，因为如果我只列成功的名字，那会是一种特别自利、也特别糟糕的幸存者偏差。

Lenny Rachitsky这个回答我很喜欢。虽然你有点谦虚了，因为你的命中率显然已经很高了。对 VC 来说，70 家里哪怕只出一两家特别成功的公司都算赢了。不过你这个视角确实很重要。很多人看到网站上挂着一排 logo，会以为那就是全部，却不知道背后到底挥空了多少次。

Matt MacInnis所以我一直觉得，好的做法是让别人把完整名单都拿出来。

Lenny Rachitsky那你最喜欢的那些“失败投资”是什么？

Matt MacInnis这个我可不太想答。

Lenny Rachitsky哈哈，行，不展开了。但我真觉得这是个好问题。把那些没成的 logo 也拿出来看看。

Matt MacInnis这问题很辣。

Lenny Rachitsky我其实还想聊一个相关话题，而且我没怎么听别人用这种方式思考过。就是你讲的“复利 + 幂律 + 熵增”这个框架，来理解商业这件事。

Matt MacInnis你一开始提到“卓越结果需要卓越投入”，那句是 Dan Gill 的。我觉得这和后面这些完全是一体的。你越理解宇宙是怎么运转的，就越知道该怎么在里面做事。

幂律分布几乎无处不在。它解释了为什么极少数人掌控了极大量财富；解释了为什么 Steph Curry 会比名单上下一位球员强出那么多；解释了为什么人口会集中到少数几个超级城市。幂律是到处都在发生的东西，一旦你看见了，就很难再看不见。
很多人默认世界是线性的，觉得横轴走一点，纵轴就跟着平滑上升一点，像 `y = x` 那样。但现实根本不是这样，影响非常深。
很多时候你已经把事情做到 80%、90% 了，可回报那条 y 轴几乎还没怎么动，因为你还没越过真正的拐点。幂律真正可怕的地方在于：处在前 10%、前 5% 的人，得到的不是多 10%、20% 的奖励，而往往是 10 倍、100 倍的奖励。差距极端得多。
再说熵。热力学第二定律其实很好理解。它就是为什么你的袜子抽屉会越来越乱，为什么路上会长坑，为什么飞机必须投入极大精力维护才能安全飞行，因为它本来就非常想散架。你把一座城市丢在那里几个月不管，它就会开始荒掉。熵的本质就是：一切自然地走向无序。
从某种意义上讲，生命本身就是对抗熵的一次短暂胜利。你我本来都不该存在。太阳给地球能量，组织出我们能吃的东西，我们就这样一直和熵对抗，直到某天输掉这场仗，大概在七八十岁，如果运气不错的话。
这和产品有什么关系？本质上，它说的是“投入”。
对抗熵、对抗系统衰败，唯一的解药就是能量。你必须持续往系统里注入能量。
你有一个 codebase，每加一行代码，系统的熵就多一点，也就要求人类投入更多精力去维护，确保它不坏。你想做出伟大的东西，想拿到卓越结果，尤其想把自己放到 x 轴最右边那一小撮位置，让 y 轴的回报真正炸起来，那你就必须在每一个步骤上，持续、不断地注入能量。
而团队呢？很遗憾，但因为我们都是人，团队天然会优先局部舒适，而不是公司结果。
这不是说大家会坐下来明说“我们就这样吧”，虽然有些组织确实会这么干。更常见的是，在一群产品经理和工程师组成的正常团队里，熵会慢慢爬进来，然后大家开始本能地优化自己的舒适区。
所以，作为高管、作为领导者，你的工作就是每天都和熵狠狠干。意思是：每次你看到 bug，都要处理。不是“大多数时候”，是每一次。你要把它扔到 PM 或工程经理脚下，最好还是公开地扔。每次有人来申请招人，说跳过了 back channel，你都要明确说：不做 back channel，这个人就不能招。每当一个流程进入“大家都烦了、都累了”的阶段，你作为高管都必须要求 99 分位的能量。否则熵就会爬进来，系统就会开始腐烂。
我前阵子在一次高层 offsite 上，对大概前 75 位管理者讲过一段话：公司里最纯粹的野心、最强烈的能量源，一定是 founder CEO。而在 founder CEO 外面，每扩一圈管理层，都可能出现一个数量级的强度衰减。这非常危险。
如果只往下传两层，强度和信号就已经掉了两个数量级，那这家公司其实已经病得很重了。所以我对团队说的不是“你们要帮 CEO 把强度缓冲掉”，而是你们必须把这种强度原样映射出去。
公司里永远不缺那种会主张“放松一点”的声音，也永远不缺会替别人挡掉要求的人。你的工作不是再做一个缓冲层。你的工作是把这股强度尽可能完整地保存下来，缓冲的事让别人去干。
因为熵就是这样，它会悄无声息、缓慢地渗进系统，在你没注意的时候一点点把东西搞散。你想一直站在幂律最右边那块地方，就只能每天、每分钟都维持住这股强度，持续跟它对抗。

Lenny Rachitsky那这种“把强度往下传”的动作，具体看起来是什么样？感觉上是什么样？比如 Parker 过来说：“这个 bug 太烂了，我打开就是个坏页面。”你不是会“切掉自己一根手指”吗，也许这就是一个例子。

还好，我十根还都在。

Matt MacInnis我给你一些非常具体的例子。其实我之前给团队做分享时，专门拿这个开过一个玩笑。PPT 下一页一出来，先放的不是内容，而是 Slack huddle 那个来电音效。Parker 在 Slack 里的头像一直用的是那个默认的黄色……

Lenny Rachitsky那个蛋？

Matt MacInnis对。

Lenny Rachitsky哇。

Matt MacInnis所以大家都知道，那个黄蛋就是 Parker。下一页 slide 写的是：“Parker Conrad is inviting you to a huddle。”再下一页写的是：“Parker Conrad is modeling personal intensity。”

意思很简单。如果你经历过那种场景，你就会懂：他说“我现在就要聊这个该死的问题。你手上除非正在面试别人，否则立刻过来和我聊。”这就是强度的一种体现。
在 Rippling，每个产品团队都有公开的反馈频道，现在团队已经很多了。我基本什么产品一用到不对劲的地方，都会直接一头扎进去，在公共频道里连续发问：“这个我不喜欢”“这个我看不懂”“告诉我为什么要这么做。”一条接一条。然后相关的人就会立刻跳出来回应。
我前面说的那个 factory inspection 流程也是一样。产品到了“装配线末端”，我就会带着那根“pickle”跳出来，把所有关键环节都过一遍。你们必须把产品里每个核心流程都录成 loom，我本人会把这些流程一个个看掉。我今天都还有 backlog 要补。然后我会继续给反馈，而且永远是在公开频道里给。这样别的 PM、工程经理也都能看到，别的团队到底是怎么被 review 的。
重点在于：你要公开地示范这种强度，让别人知道，“哦，我们这里就是这么做事的。”
更有意思的是，团队收到这种信号之后，反应并不是“啊，好累”。真正普遍的反应反而是：“这太提气了。”
大家会觉得，太好了，我们真的在争取很大的结果，至少我们有机会去争。而且你其实是在授权我按照自己的直觉去追最好的结果。
所以团队几乎一致的反应都是：“太好了，原来我可以这么 intense。”因为说真的，没有哪个坐在领导位置上的人，内心深处真想当个 chill boss。
还有什么比 chill boss 更糟吗？不要替 chill boss 工作，也不要自己变成 chill boss。这几乎是我能给一个领导者贴上的最负面的标签。什么 chill boss、chill PM，都别做。chill 什么都做不成。你可以善良、可以尊重人，但你必须有强度。别 chill。

Lenny Rachitsky而这又回到了我们最开始那件事：这就是成功长什么样。因为总会有一个比你更不 chill 的人找到那条缝，狠狠干进你的市场。大意是这个意思，对吧？

Matt MacInnis当然。还是那个逻辑：如果你一 chill，x 轴往左掉个 10 点、20 点，y 轴不是跟着掉 10%、20%，而是会直接塌掉。这在很多事情上都成立。所以如果你想赢，最好真的去拼。

Lenny Rachitsky这也是我总跟那些想做 lifestyle business 的人说的话。很多人会想：“我做个副业，搞点 recurring income，多爽。”但按我的经验，只要一个市场里有油水、有人能赚到钱，就一定会有人比你更拼、筹更多钱、跑得更狠，而你能守住这件事的时间其实很有限。

Matt MacInnis这又可以单开一期聊 leverage。如果你卖的是自己的时间，那你一天就只有 24 小时可卖。但如果你做的是一个可规模化的产品，比如软件，边际成本几乎是零，那这个市场就一定会非常卷。卖时间，未必那么竞争；一旦拥有了这种杠杆，市场自然会变得非常有效率。

Lenny Rachitsky说回“强度”和“给系统持续加能量”这件事。我还听说你特别强调 escalation，也特别强调负面反馈不能藏着，要有人说就直接说。讲讲这两件事吧。

Matt MacInnis本质上，最自私的行为就是把本来对别人有帮助的反馈憋着不说。因为你这么做时，你优化的到底是谁？当你脑子里明明有一个想法，知道它能帮助对方进步，却因为怕自己不舒服而不说，那你优化的其实就是自己的舒适感。

这在本质上就是自私。而高绩效团队不是这样运作的。
所以我会要求反馈，也会主动给反馈。这不意味着我给出的反馈不能被质疑、不能被讨论，当然可以。但只要我观察到了什么，我就尽量把它说出来。这是 feedback 的部分。
另一件让我觉得很有意思的事是：人们会压住 escalation，不只是内部的人，客户也会。
很多客户其实不愿意把问题 escalate 到我这里，哪怕我是高管。甚至那些我投过的公司里，只要他们也在用 Rippling，出了问题之后往往也不好意思直接来找我，觉得像是在打扰我。但这明明就是我的工作，字面意义上的工作：发现问题，把问题变得更好；并且通过修这些具体问题，去倒逼流程改进，让“构建系统的系统”也变得更好。
对一个产品高管来说，没有比收到客户 escalation 更好的礼物了。
Rippling 甚至有一个专门的 escalations team，听起来可能有点怪，但这群人特别擅长做一件事：狠狠干着公司里所有人一路往下追，直到把真正的 root cause 追出来。
我说的是真正的 root cause，不是那种嘴上说说的 root cause。不是“数据错了，我们修一下数据然后关单”这种。真正的 root cause 是：你得找到生成这条错误数据的软件，再找到制造这套软件的系统，然后一路把这个问题从最底下往最上面全都打穿。
Rippling 的 escalation 团队在这件事上非常强，所以我们确实专门有一小支队伍干这个。如果你现在正在听这期播客，而且你是 Rippling 客户，手上有任何你觉得我们该知道的问题，请记住：哪怕我可能已经知道了，也不是你不告诉我的理由。你的反馈本身就是礼物。
我每天都用这种心态看待这件事。我手上现在都还排着几个小问题，是最近几天别人提给我的一些小毛刺。我已经把它们记进今天的待办里，准备直接带去找相关产品团队，问一句：“我想知道这里到底发生了什么。”
不是为了追责，而是因为我真心觉得，把这一个案例研究明白，大家都会更强。所以对我来说，escalation 是礼物，反馈是礼物。谁来给我提这些，都不是在打扰我。

Lenny Rachitsky如果有人听到这里，会觉得“天哪，这也太累、太猛、太高压了，我不确定我想不想这么工作”，你能不能给大家一些 Rippling 到底有多成功的背景？我觉得很多人可能甚至都不太了解 Rippling，只是知道“它挺不错”。有没有什么公开或半公开的信息，能让大家感受一下这家公司已经做到了什么量级？

Matt MacInnis很多人从外面看 Rippling，会觉得我们就是 payroll、HR 那类公司。也没错，但这就像说 Microsoft 是一家桌面操作系统公司一样。每家公司都会从某个点起步，然后一路长出去。

而我们对自己的定义是：打造历史上最成功的企业软件平台。
这甚至已经成了我们产品组织内部的 mission statement。当然，它仍然服从公司更大的使命：让聪明人从繁琐事务中解放出来，去做难问题。
如果你把我们今天所处的位置和我们要去的地方连起来看，就会发现，我们真心相信：无论一个公司的工作流长什么样，不管是 AI 驱动的，还是传统 GUI 驱动的，它最核心的问题始终都是“谁在做事、谁拥有这件事、谁对结果负责”。
所以，“人”这条记录是极其重要的底层原语。你当然也可以说 customer record 很重要，也确实有很多大公司建立在那个原语上。但我们认为，people primitive 其实更重要。
而这个方向真正一直没人做成的原因，只是还没有人足够有野心，基于这个原语搭一门真正伟大的生意。Workday 是很糟的软件，这点大家都同意，我觉得连 Workday 自己都知道。尽管它很成功，但它实际上并没有在“people primitive”这层基础上，真正搭起一个广义、通用的企业软件平台。所以这件事，我们来做。
而我们之所以能成功，是因为在今天这个规模上，我们已经在兑现这个承诺。
这不是 sales pitch，也不是给 Rippling 打广告，我只是想让大家认真想一下：如果你把一堆分散的业务流程，真正收进同一个系统，落在同一个业务数据图谱、对象图谱、统一接口之上，你会拥有多大的魔法空间。
我们现在做 payroll、做 HCM、做 IT、做 spend，接下来还要上线新的 BI 和数据管理产品，后面还有很多东西。而当你再把 AI 叠在这一层之上时，你会发现：只有我们手上把企业的业务数据整整齐齐地组织在一起，还有一层漂亮的 semantic layer，AI 才能真正玩出魔法。
说真的，我们在这个方向上到现在还几乎什么都没真正放出来。我认为明年会出现的东西，会把行业标准重新定一遍。光是我们在内部用例里看到的那些 AI 对数据的读写、折腾、翻跟头式的能力，就已经让人下巴掉地上了。所以我对这股顺风非常兴奋。

Matt MacInnis你问我，公司成功这件事能公开讲什么。我能说的是：现在已经有数以万计的公司在跑 Rippling，而我们在整个市场里占比还不到 1%。以 160 亿美元估值来看，我甚至觉得从收入角度讲，市场还远远低估了我们。我们要做的事情，向上的空间还大得惊人。

如果你说的是 point solution 那种 SaaS，也许它确实已经有点“半死不活”了；但如果说的是我们正在搭的这种 SaaS，那它的时代远远没结束。

Lenny Rachitsky那我就顺着 AI 这条线往下问。现在有很多说法都在讲，AI 会替代 SaaS，某种程度上你刚才好像也在这么暗示。

Matt MacInnis对啊，大家准备靠 vibe coding 给自己做 payroll 系统了。那我只能祝这些公司的员工好运。

Lenny Rachitsky所以你的意思其实是：那些只卖单点解决方案的 SaaS 公司，确实会很麻烦。换句话说，未来用户愿意持续付费，不是因为你只做了一件小事，而是因为你替他们做了很多事情。是这个方向吗？

Matt MacInnis不完全是。这里有句很好的话，我忘了最早是谁说的，大意是：“软件里只有两种赚钱方式，bundling 和 unbundling。”关键只是你要踩准时机。

而现在就是一个 bundling 的周期。
问题在于：单点产品在 AI 时代没有足够多的数据，所以很难真正有用。AI 要能做事、能做 joins、能做 correlations，它就必须拿到足够多上下文、足够多数据。
如果你是 point solution，那你就会很难受，因为你不得不依赖别处的数据。你得去接第三方系统，而一旦接第三方系统，再好的集成，本质上也只是“拿吸管喝别人家的数据”。这是个大问题。
举个例子，你能想到的最大 HCM 软件公司，和你能想到的最大 payroll 软件公司之间，很多时候居然还是靠 flat file 走 SFTP 在同步。那他们还能怎么办？根本没法做。真的没法做。
所以我坦白说，我都不知道他们该怎么办。也许他们就是做不出真正的 AI 软件。point SaaS 现在处境挺难，尤其是当你把两个本该紧密咬合的重要系统硬生生拆开，然后要求它们再“集成”回来时，难度会非常高。
再往外一点说，不只是 SaaS，AI 软件里的 point solution 其实也同样难受。逻辑一样。
如果你是卖“铲子”的，比如 OpenAI、Google Gemini 这种基础模型提供商，你能赚钱。
如果你是“矿主”，像 Rippling 一样手里握着数据，你也能赚钱。
但如果你卡在中间，做一层 AI 软件，一边要借“铲子”挖，一边又得去租别人的矿、把矿石从别人那里拿出来再自己提炼，那从经济模型上看你就站在一个很难受的位置。
因为不管是卖铲子的，还是拥有矿的，都不会允许你长期踩着他们的背做出一家超级大的公司。
现实大概率是：他们都会要求自己那一层拿走足够多的价值，而这会直接把你的 unit economics 压垮。
所以我现在看市面上很多 AI 公司，会觉得如果你没有一个特别耐打、特别有意思的核心洞察，能让你有机会建立可持续的 unit economics，那你就很难成为一门真正有意思的生意。
而这会杀掉我现在看到的 80%、甚至 90% 的独立 AI 公司。

Lenny Rachitsky所以你的意思不是“SaaS 好不好做”本身，而是：你手里有没有 first-party data，足不足以让你在这上面搭出真正厉害的 AI 产品。对吗？

Matt MacInnis对。因为说到底，SaaS 软件本质上就是在 flip bits。所有 SaaS 应用，说穿了都是 bit flipper，它们就是换一种接口去改……

Lenny Rachitsky你的数据库？

Matt MacInnis对，就是改数据库里的值，这就是它干的事。

当然，这件事本身很难。Rippling 的一个超能力就是我们像一台“分币机”。你把某个员工 2 万美元的成本从入口倒进去，系统要非常可靠地算清楚：多少给政府、多少给健康保险、多少进 401(k)、多少发到他自己手里。所有这些钱都得极其稳定、顺滑地流向各处。
这当然是很难构建、也很难维护的软件。但说到底，它依然是在数据库里翻 bit。
而 AI 只是翻 bit 的一种新方式。AI 只是另一种翻 bit 的方法。希望它能把我们再往上抽象一层，让我们少操一点心。反正我们的未来就是《WALL-E》，会很棒。

Lenny Rachitsky说到《WALL-E》，我家里 actually 有个 Matic Robot。你有这种东西吗？

Matt MacInnis嗯？

Lenny Rachitsky就是那种像自动驾驶小车一样的家务机器人，会自己在屋里跑来跑去打扫卫生。

Matt MacInnis哦，懂了。

Lenny Rachitsky有点像 Roomba。你该买一个，虽然贵，但真的很酷。其实《WALL-E》里就有点那个意思，所以那部电影也没那么离谱。

Matt MacInnis它确实挺有先见之明的，至少除了那个反重力躺椅以外。

Lenny Rachitsky嗯，也许吧，但听着也不算什么好消息。那回到 AI，这是不是意味着接下来会出现更多整合？这些单点公司会发现，没有数据这件事是生死问题，所以它们会像你说的那样去合并、去 bundling？

Matt MacInnis有可能。

Lenny Rachitsky至少在当下是这样。

Matt MacInnis但我不是研究这个的最佳人选。我觉得有些投资人在这件事上想得非常深，尤其是像 Mike Vernal 和 Sarah Guo。

这两个人对 AI 都是高度聚焦的。当初他们决定这么做时，我还觉得这个方向是不是有点窄。现在我反而觉得，不不不，他们当时完全走对了。这意味着他们在看遍硅谷所有 AI deal 的过程中，已经积累出非常深的一整套假设体系。
这个问题其实有比我更适合回答的人。如果你是创业者，我会推荐你去和他们聊，因为他们真的很聪明。

Lenny Rachitsky太好了，我也很喜欢他们。顺便推荐一下 Sarah 和 Elad 的播客 `No Priors`。那回到 AI，这个领域里如果你还要给创业者留一句话，你会说什么？比如“如果你想赢，你该怎么做”。

Matt MacInnis能说的其实很多。但如果我现在真的给出一个笼统答案，那大概率就是胡扯。还是回到我前面那句话：我在这件事上没有足够多、足够抽象层面的相关经验，适合直接在播客上发一通“建议”。所以，我只能祝他们好运。

Lenny Rachitsky我喜欢这个回答，也很喜欢你前面那句：别要 advice，要 relevant experience。你刚才脑子第一时间就回到了这件事。下面我们进入播客的固定环节 `AI Corner`。问题很简单：AI 在你的日常工作里，具体帮到了你什么？

Matt MacInnis这个答案可能没那么刺激，但我说一个我确实常用的地方。

作为高管，我最重要的工作之一，其实是把各种想法做综合，再把它们非常清晰地表达给别人。比如我刚才讲的 product quality list、pickle 这些内部概念，我会把一整套已经想得很尖锐的观点丢给 AI，用 ChatGPT、Gemini 之类的工具说：“你看，这就是我想表达的核心。帮我想一些更短、更准、更有力的说法。”
它输出的 80% 都是垃圾。中规中矩、平均值、low alpha 的垃圾。
但它确实是一个不会评判你的思维伙伴。而在剩下那 20% 里，有时候它真会给出一句不错的话，一个我自己没想到的词，刚好就把这个概念钉住了。
如果我把自己的工作理解成“带着别人的脑子一起穿过某种变化”，那我手里最重要的工具就是语言。在这件事上，ChatGPT 和 Gemini 确实能很好地帮我把想表达的概念打磨得更利落。但它们并不擅长替我想出那些想法本身。

Lenny Rachitsky这建议很好。你不知道有没有多用过 Claude？我自己的感觉是，Claude 在写作、遣词、语言这件事上更强。

Matt MacInnis我没怎么认真用过 Claude。用是用过一些，但听你这么一说，我大概会去多试试。

Lenny Rachitsky对，它们都很强，只是 Claude 在写作这件事上有点特别好。当然，现在大家都在飞快进步，永远都会有新东西冒出来。

Matt，我们今天已经聊了很多，也基本把我想聊的都聊到了。进入 lightning round 之前，你还有没有什么想补充的？或者有没有什么话想留给听众？

Matt MacInnis有。今天我们花了很多时间在讲强度、讲 grind、讲为什么你必须长期维持在 99 分位的状态。

如果把这些话单独拎出来听，很容易让人以为这种强度是很压垮人的、很负面的、也许根本不是你想要的。
但我自己心里其实一直有一个“托底”的东西，今天还没讲到，我觉得很值得说出来：那就是，生命本身非常神奇。
我们竟然存在在这颗漂浮在时空里的蓝色小球上，我们每个人都是某种奇怪的意识实例，而且你能在这里活着的时间又短得惊人，在这么短的一段时间里拿着你的小棍子在那边削来削去、做点什么事。如果你记得我们自己和我们做的这一切，其实都非常渺小，那你反而会对手头这些工作生出一种轻盈感。
因为 2025 年的硅谷，某种意义上就是文艺复兴时期的佛罗伦萨。真的太疯狂了。我们这个物种此刻在这里爆发出来的创造力、发明、推进速度，在整个人类历史里几乎都无可比拟。
你得跳出来，感受到这件事有多神奇。
然后你再回头看，就会说：好吧，那我周五晚上还是得干。我还是得全力以赴。我还是得走进商业这座竞技场里去打。

Matt MacInnis但你永远不能忘记两件事。

第一，这一切其实都没那么重要。
第二，能在这个时刻活着、站在这里做这些事，本身就是一件极其美妙、极其惊人的事。
所以去打这场比赛吧，拿出你全部的力气去打。但永远别忘了，它终究只是一场比赛，而它本身并不是全部意义所在。我觉得这是我们前面聊“强度”时一个非常重要的配重。

Lenny Rachitsky太美了。

Matt MacInnis我会想到 Carl Sagan 那张 `Pale Blue Dot`。那真的是一张惊人的照片。我第一次看到它时，它几乎直接改变了我理解“自己是谁”的方式。