10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

It 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 crust. You'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. If you wanna be in the ninety ninth percentile in terms of outcomes, it's gonna be really difficult. You gotta 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 freaking exhausting. You're a big fan of escalating issues? Fundamentally, 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 of really interesting experiences with your own startup. We talk in Silicon Valley about never quit, but that is complete, absolute venture capital bullshit. Today, my guest is Matt McGinnis, chief product officer and formerly long time chief operating officer at Rippling. If you don't know much about Rippling, it's a massively successful business, last valued at over $16,000,000,000. 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 have not heard anyone else on this podcast share, and I left this conversation feeling that every leader needs to hear his advice. A huge thank you to Albert Strashim and Sunil Raman for suggesting topics and questions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. 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Head to a i.studio/ build to create your first app. This episode is brought to you by Datadog, now home to EPO, the leading experimentation and feature flagging platform. Product managers at the world's best companies use Datadog, the same platform their engineers rely on every day to connect product insights to product issues like bugs, UX friction, and business impact. It starts with product analytics, where PMs can watch replays, review funnels, dive into retention, and explore their growth metrics. Where other tools stop, Datadog goes even further. It helps you actually diagnose the impact of funnel drop offs and bugs and UX friction. Once you know where to focus, experiments prove what works. I saw this firsthand when I was at Airbnb, where our experimentation platform was critical for analyzing what worked and where things went wrong, and the same team that built experimentation at Airbnb built Epo. Datadog then lets you go beyond the numbers with session replay. Watch exactly how users interact with heat maps and scroll maps to truly understand their behavior. And all of this is powered by feature flags that are tied to real time data, so that you can roll out safely, target precisely, and learn continuously. Datadog is more than engineering metrics. It's where great product teams learn faster, fix smarter, and ship with confidence. Request a demo at datadoghq.com/lenny. That's datadoghq.com/lenny. Matt, thank you so much for being here, and welcome to the podcast. Thank you for having me. I wanna 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. I this 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, not just 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, like, the general concept of management. Like, 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, like, 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 wanna be in the ninety ninth percentile in terms of outcomes, it's gonna be really difficult. Like, it's gonna be really uncomfortable. And you gotta sort of remind people of that, that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. Like, they have definitely screwed up somehow. It's not that, 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. To make this even more real for people, what are examples of moments that were extraordinarily hard? It is not about any sort of grand single story. I think the truth 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 is is an reminder that, like, it's supposed to be really freaking exhausting. It's supposed to be. So, like, on Friday night, when you get hit with an escalation on Friday night, when you get sort of, you know, 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 because we're winning. Like, 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 on the revenue foundation that we have is extraordinary, like, really, really compelling. And it 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 is not growing very quickly, if things aren't that great, if your growth rate is 30% or 40%, you know, it doesn't feel as good as a contributor in that business to, like, lean in and give everything you've got on Friday or Saturday or Sunday because you don't know that it's gonna 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, like, 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 is actually contributing to an extraordinary result. It's a it's a 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, you know, when I'm wringing the oil out of somebody who's in the bored and tired zone. I saw the same thing actually at Airbnb with Brian Chesky. I always felt like things were going great, and, like, 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, like, a moment to take a break. I spent seven years at Apple and learned under Steve Jobs, you know, when he was the CEO, learned what we called the death march, which is what we did to the engineers. It was like, the the soon as you ship one version of the the iPhone, like, you were just immediately thrown into the into the pit of building the next one. And there was no break. It was just it was just relentless. And talk about an extraordinary outcome at the end of the day. There is no relief. It's just like every 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, like, 100% chance they're gonna 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 sort of live their lives, of course. And you can't it's not like people are human beings who can't grind the individuals down, but the team as 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, you know, that's the beauty of capitalism. Also, very counterintuitively and, maybe, like, the 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, 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, like, many week break and slowing things down, I find they get more more actually goes down in those in those moments. Here's the so 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 gonna ship something. But, of course, you have to set some default, so you 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 in business in general, everything's emergent. It's these are not things that are knowable top down or a priori, 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, is better. And so let's talk about staffing. Like, when you staff a project, is it better to overstaff, or is it better to understaff? Knowing that you can't get it right. Well, it's better to understaff. If you overstaff, you get everything 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, like, you know that you gotta do the top five, but the next 15 down is kind of ambiguous. But you've overstaffed the project, so, like, 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 understaffing is less evil than overstaffing. In this particular framework, the advice is understaff deliberately, always. And then the wisdom the wisdom element is to know not to under understaff 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. There's a previous guest, I forget who that this who this was. They use this metaphor. They want their team to be dehydrated, to always be wanting more water. And then eventually, they're too dehydrated. And, okay, let's we needed someone's help. Interesting. Yeah. There's a line along the lines of extraordinary efforts I wanna 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 teams' asses. Yes. This was a quote actually from Sunil, and he found it from a from a women's, basketball team coach. And it is it is to my point earlier about, like, you gotta run the engine at in in 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 gonna come in and kick the good team's ass. And it's like, you know, 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. You know, none of this matters. We're not gonna carry it to the grave. It's like you're here 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 that sports, notwithstanding the fact that I watch very little of it, isn't is a very that military. You know, those are very ripe sources of parallel concepts to apply in leadership. I 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 you don't feel that. So I think that's a really important component of this is you need to be winning and succeeding. I mean, one thing that I've learned from Parker is Parker is our CEO at Rippling. He, you know, he said, you don't 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 you learn a bit from mistakes. But I do think that this is sort of, feel good bullshit that, you know, it's like, well, you know, you didn't succeed, but, you know, at least you learned something. I've had failures. Like, 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, Like, 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. Like, I've seen rapid, wild, crazy, off the charts success of the business, and, it's more informative. Like, 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 gonna get on an airplane and one maintenance technician has seen it done right a 100 times, and the other maintenance technician has seen it done wrong a 100 times, but he learned from his mistakes, like, if it still hasn't had any success himself, I mean, give me a break. This is not even a comparison which plane you're gonna feel more comfortable on. And so I do think that, like, learning from your mistakes thing is a bit of a feel good trope that actually has very little substance in reality. It's it's and it's why as an early career product manager or it's it's why, like, frankly, at any stage of your career when you wanna learn, you should join a winning team. Like, 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, like, really good companies when those companies were super exciting and in crazy growth mode. I'm like, I instantly wanna interview that candidate because I wanna hear what they learned from being part of a winning team. And that's, that's sort of one of my go to heuristics when I'm looking at candidate profiles, and I think it's an undertold trope. Like, we're not sorry. Not an untold trope. It's a it's a piece of advice that I don't think people embrace enough in the Valley that, like, success begets success, and you should chase success. Speaking 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 CEOs moving into product. Let me ask you why that why did you move into 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 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. The story at Rippling is pretty interesting. And, I'll tell it because I think it explains why, you know, 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, you know, talking about McGinnis' 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, you know, like, not always wild success. But I did that anywhere everywhere except r and d. I would be I would, you know, think about helping out with components of the sales organization, like our channel team, or I spent time, you know, building out the recruiting function a few times when it needed to be sort of, rethought in response to our growth. And but it never r and d. And so I I sort of 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 gonna go in and deal with that. And, you know, the 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, fuck. That that architecture is not right or this you know, 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, 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 of things and just never really having good executive leadership over both engineering and product at the same time. And, I remember Park sort of Parker sort of slumped down in his seat and said, oh, fuck. I have to run another search. And I said, no. Like, the gig's up. I'm gonna go do it. And he really sprung up in his season. Really? Like, you'll go do that? I'm like, dude, this is what 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 gonna do it and expressed that to Parker in December. I really took it on in January '25. And so it's been eleven 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 eleven months have been to establish, you know, like, greater clarity in terms of how we do things around here, better process, better, you know, general leadership, hiring and firing. I mean, just doing this sort of cleanup on Aisle 3 that needed to be done even though a lot, again, a lot of the people in the in the team were quite talented and doing an excellent job of managing their specific domains. Jumping into the product role has been, like, 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 sort of 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, you know, we need to establish some 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 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, and develop hypotheses for how to amend the system. And that's what I've been doing. I love hearing this because so many people have teams that are not functioning incredibly well. And hearing from someone that is not a long time product person come in and try to fix these problems, I think is really useful and interesting for people to hear. To to dig into this a little bit more, was the big lesson and kind of, eye opening moment that there's a lot of kind 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 the lesson there? The lesson is that everything must be done in its time and order. And you can move really, really quickly. You can you can there's no sort of excuse not to move with urgency on all of these things, but you gotta do them in order. And you have to you have to lead bottom up. Like, you gotta lead from the specific circumstances you observe. And I think for me, one of the best things that's happened over the last eleven months is that I've gained a greater trust in my own instincts that that the that the 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 let 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, like, 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. Like, I realize that that's a tautological 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, like, very happy users. It's got an awesome growth profile. And so we should still we should be really focused on the adoption metrics because I think that's gonna be an important ingredient to low churn over time, you know, 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 to deliver once it's adopted. Now 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? I'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 seeking alpha.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 and 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 is not good. A high beta stock jerks around for no particular reason. It's, like, discorrelated with the index. It just you know, 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. And 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, you know, 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. And 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 gonna 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, 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 the 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 in the product team to know that you're lowering beta in the places where you wanna do that without suppressing alpha in the places where you need it. And so as we've gone through the last, you know, 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. And so examples of this are, let's say, our product quality list, which we lovingly at Rippling call the pickle. Why pickle? Yeah. So it's actually a really important thing. I think if you wanna bring about cultural change in a team like, look, we have we have 1,300 people in our r and d organization. It's a big ship that we have to steer. If you wanna create a moment that sticks in people's brains and sort of becomes a zeitgeist or something that they latch onto, you gotta create an entity, a vessel for meaning, and then you gotta fill that vessel with your meaning. A meme, you might say. Yeah. Well, it's sure. A meme yeah. Like, a meme is actually a good example of this in common culture, you know, and, I, in pop culture I think, like, it's why when people come to the table with with ideas from the outside, I welcome those outside ideas. But if 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 wanna 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. And so with the pickle, 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 you wanna 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. And so Pickle, 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. 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. And 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. And so he also installs any new app that we're gonna 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 in their companies. And he installs it, and he goes in and it dumps him onto an empty screen. And he's like, what the fuck is this? What is this? What's going on? Like, hey. Wow. We're talking about fail. So I, chop another one of my fingers off. I'm down to nine. And, I'm like, what what did we miss? What we missed was there was a fucking feature flag. Fucking feature flag. I'm just I'm not allowed to say feature flag without fucking in front of it because, like, 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 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. Like, 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 pickle for feature flags. And so I added a line to the fucking pickle 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 pickle, 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. And so that's you know, you asked me a very simple question. I gave you a very long winded answer, but these frameworks help me design systems that scale, you know, across one going to 2,000 technical workers. Wow. Okay. By the way, Pickle, is that is that, like, an acronym, or it's just like, I like this word we're gonna call it Pickle? Product quality list. Product. Okay. I see. It's it's the continent. Okay. That's p q l, which Okay. How could you pronounce it other than pickle? I'm imagining all your decks have little pickle emojis and and The pickle emoji thing, the dancing pickle in Slack. There's a lot of yeah. It lends itself to a bit of fun. What I think about is Pickle Rick. Yeah. Do you think do you get that reference? This is a Rorschach test. Okay. So this high alpha, low beta, I 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, we're okay with a lot of variance for this specific project that's Yeah. 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 these or the lack of process that sort of gives them the latitude to do what they wanna do. And so when you're hiring, you're looking for, again, is this person in low beta or not? That's going to be For sure. I mean, it's really quite a useful way. You know, when you meet a candidate and you I mean, my modus operandi, and I think, you know, 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, you know, maybe tens of thousands. I don't know. It's a lot of batting practice and a lot of model training in my brain. And so I rely a lot of my intuition, which, of course, HR people say you're not supposed 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 a reaction to a candidate when you when you're looking at, hiring somebody is you need to decode you need to decode your intuition so that it can be expressed to other people productively. And 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 it's that people are smart, passionate, optimistic, tenacious, adaptable, and kind. Those five things. Six, can't even count. I I told you I lost a finger, right, when I made a mistake. So I was down one. Nine nines ago. Spotac isn't by itself a good top down framework. But when you're thinking about, why did they not why did this candidate just why did it not click? Why did I not like them? You go down the list, like, oh, yeah. I know. This person it's it's that they were not excited about the idea. They weren't passionate. You know, it's like, it's that they talk 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. You know, it's the the framework is super useful to evaluating people, and I think the the alpha beta framework is also super useful. When you come away from a conversation, 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. And so I think it's really useful in that context as well. I love all these frameworks. You're speaking to this audience. Frameworks, frameworks, frameworks. Yeah. So high high alpha, low beta, sometimes, high beta is okay. Spotek. In hiring, is there anything else that you find really useful before we move on to a different topic? When 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. Like, 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 in the 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. I I you know, you never think that, like, giving someone an impossible task and even including the l five person versus the VP on the same thing would be productive. And let's just say our recruiting team still sort of covetches a bit about this and feels like we eliminate people too aggressively at this stage of the interview process. But I 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. You know, they're never gonna get all the way through the wall. It doesn't matter. You're gonna learn a lot. And I found that to be kind of an eye opening new thing for me that that has been fun. I mean, look, the joy of product and the joy of product management and the joy of of being part of I think there's a bunch of joys, actually, if I could give you a sort of running list. But, like, 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, you know, entities. Salespeople are awesome social entities. They're not always the best systems thinkers. You go down the list, but the the magic of product management is that you kinda have to you know, we talk about the the mini CEO. I think it's kind of a stupid misnomer. But there's some there's some wisdom there, and I think the wisdom is that you have to be a polymath. Like, you've gotta be really good at working with other people. You gotta be good at communications and articulation. You gotta be good at project management. You gotta be good at the science and the math and the engineering. It's really fucking cool. And so I think one of the great joys of this job for me has been interacting with, like, the the tippity top of the smartest and 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, the 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, like, optimized itself around what the product was. It was about recruiting and making sure we got people in to work on the product. You kinda go down any function that isn't in r and 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 bid. Not that I didn't sort of understand that, but, like, now I really get that product is the high order bid. 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. And so I think the other joy of of leading the product function is that, I get to set the highest order bit in the business's success to one. This 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, you know, sales folks, CEOs a lot of times. I love that you're seeing this and realizing this and recognizing just how, important and interesting and, and challenging this work is and just how awesome PMs are. You know? As you know, a lot of people are very anti product manager. Why do we need product managers? We don't need them. Just let everything down, all this process. I have a distinction there, which is I'm anti shitty product managers. That's exactly how I put it. If you hate product managers, you just haven't worked with a great product manager. Look, I I love wine. Wine's one of my things. And I've learned a lot about wine. And one of the my favorite lines, like, I don't like Chardonnay. And I'm like, no. No. No. No. No. Chardonnay is the most fucking amazing varieties of of wine in the world. You just haven't had good Chardonnay, you know. And, there's a Chardonnay out there for you. Management is like, you don't like product management. You think product managers suck? It's like, well, you just you just haven't had a good Chardonnay yet. That's exactly what you have. Once you have one, you know, you can't unlearn it. You know, like, let's find that PM ASAP. Oh, let's find that Chardonnay ASAP. Well, that you have with them with some Chardonnay. You bet you touched on this product market fit point, and I wanna double down on this thread. You had a 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? Mhmm. Okay. 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 There's a line that, the this venture capitalist whose name I will not mention said, which was, you know, that that, product market fit is a sort of thing where you you absolutely know it when you see it. And therefore, if you don't absolutely know it, you don't have it. And this kinda 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 that I spent at rippling sorry, inkling. We thought we had it. We thought we had product market fit, maybe maybe, you know. And in hindsight, with the benefit of now having experienced solid product market fit, it was so so obvious that we didn't. And, like, I've invested in, like, 60 companies or 70 companies. I don't know. It's not something I actively do, but but opportunities by virtue, I think, of my 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, you know, 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. And 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. You know, Airbnb, maybe. It's like there's some examples of companies having made wild pivots and succeeded, but, man, is that rare. I mean, just so exceedingly rare. And I think it's important to remember, like, you know, I'm 45 years old. I we're gonna be on the planet. I mean, the average age of a man in The United States when he dies is something in the mid seventies. Like, I got twenty, thirty, maybe, if I'm lucky, forty years left on the planet. Very conscious of the time that I have. And, like, 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. And so it's a 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? Beautiful. The the, the anti the anti VC speech. The I got more where that came from. By the way, it's not it's not anti VC. It's anti VC propaganda. It's the incent everybody's acting in accordance with their incentives in Silicon Valley. The executives, the founders, the the venture cap everybody's, of course, acting, behaving in, you know, 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 have 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 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 wonder all of them. It's really wonderful people. It's it's just that the incentive structures lead to some real harm, I think, in certain cases. And the thing I find is when you do quit, VCs like, I'm always just like, hey. Let me know when you're starting your next day. I'm excited to invest. They're never they're rarely unless they're not a great VC, they're rarely are they just pissed at you for, like, how could you possibly not make this work? That's the thing. Like, as a 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 gonna go to zero. Any seed investor who doesn't take that stance is is off their rocker anyway. You know, they're a very bad investor. Seek investors who play the long game, who wanna 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. I mean, this is like I've had that conversation many times. This episode is brought to you by GoFundMe Giving Funds, the zero fee donor advised fund. 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And this begs the question of just when is the time to quit. You know, people hearing this might be like, oh, man. Like, what are some signs that, okay, it's time to it's time to wrap it up? 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. You know? Like, 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 it is five years from now today. And so I think, like, 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 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 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, you know, with 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 all is, of course, very important to believe in what you're building and to be, you know, like, to be persistent. But there is definitely no shame in saying, look. We've pivoted once or twice. It's not catching. I gotta go do the next thing. And I think, like, 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 gonna, you know, face, from the outset that that that that that now is is gonna convert to something crazy. So that's hard to hear, I I guess. But, man, it can be really liberating when you're like, fuck it. I'm I'm gonna do this. I have the energy. I'm gonna do it again. I'm just gonna do it with a clean sheet. That is really helpful. You have this really fun way of describing product market fit around, receptors and drugs. Oh, yeah. Yeah. I think this is, like, a really fundamentally misunderstood dynamic. When I when when founders message me and they're like, hey, like, like my LinkedIn post and my tweet for this launch, I do it. I retweet it. I like it. Whatever. Nobody follows me on Twitter anyways. It doesn't matter. But like, I do that. And then, but I think to myself, like, this is not what this is about. Like, this is not how great companies are built. It can be a a nucleating a nucleating event, but it's not a major thing because nobody cares about your company. Like, your launch doesn't matter. Big fat pull the 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 gotta build it brick by brick bottom up, and and these launches don't really amount to much. And so how do you think about that? Like, 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 gonna have product market fit? Well, if if you recognize that the market is immutable, no amount of tweeting, LinkedIn posting, advertising is gonna change whether the market wants your product. It's not it might raise awareness about your product, but it's not gonna 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, like, 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 very software product you build. Fate has already decided the outcome. The market's either gonna 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 I 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. What 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 there a lesson from there? Like, is that a rare example where it actually worked and that's not an example to be inspired by because it's extremely, truly rare? Let's talk about alpha beta again. Okay. As an investor, you might build a checklist of things you wanna make sure are true or false about a company and hope that that's going to yield the kind of, like, investment success you're looking for. Does it have this kind of founder? Does it have you know, is it a C corp in Delaware? Like, you know, 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, like, 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. And 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 gonna build. And by hook slash 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 it's a good idea for very many people that happened to work for them. And I look at it as being a function of the founding team and their specific idiosyncrasies, the 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, the good ones, accept what they get in exchange from that for the universe from the universe. I 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 wanna ask another question around investing, what are some other companies you invested in early? First of all okay. So I I I sort of hate the question. Like, what are some other companies you've invested? That's a fair question, but the problem is, like, I'm gonna give you a bunch of companies I've invested in that that won. You know, that are, like, really notable. So, what I would like to do instead of answering that question so I'm gonna get here. Let me let me give you some some, like, some bait. Like, I I was one of the first investors in Notion. I was perhaps the first, I don't know, ask Ivan, Clever, which you had a great exit. I was one of the first investors in Zenefits, if you've heard of it. Heard of it. I, was, before I joined, one of the first investors in Rippling. And then more recently, like, invested in, here's a funny one. I was one of the first investors in Deal, if you've heard of them. I You know, I I was able to exit I was able to exit that position and then, you know, hopefully, that company is going to zero with their criminal behavior, but whatever. I was but more recently, like, you know, if you've if you know, like, Decagon, which is doing some really cool stuff on the AI front. Killing it. I mean, Langchain, like great. So those are some companies that you maybe have heard of. But, like, how about, like, I invested in macro. Founder was Derek Lee. Macro's out of business. I invested in debrief, Ned Roczen. It's it's out of business. You know, 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, like, most of them went to zero. And all those founders were awesome. All those founders were kick ass. And all those founders put a shit 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, you know, call in a favor and and and have and I've, you know, 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. I love that answer. I think, 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 is a win in VC. And so, you're doing very well. But I 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 they've how many had bats they've had. Hey. It's good practice to ask people to give you the full list. Yeah. What are your favorite failures that you've invested in? Oh. Yeah. No. I'm not I'm not actually okay. Well, I was like, you know, we don't spend time on it, but I think it's actually a good question. Yeah. Like, what are some of your family your best failed investments? Show me the logos of the companies that didn't work at. It's a really it's a juicy question. Yeah. There'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. So you you you kick this conversation off sort of invoking the extraordinary outcomes demand extraordinary efforts line. Hat tip to Dan Gill. And these are part and parcel. Like, man, understanding the nature of the universe is a pretty good way to work within it. And so, like, power law distributions happen everywhere. It explains why so few people control so much wealth. It 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 really relatively small number of mega cities in the world. It's like, power law distribution just plays out everywhere. And, like, once you see it, you can't unsee it. It's it sort of plays out in many dynamics. People tend to think that, like, the world plays on a more linear relationship where the x and y axis are sort of, you know, 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 has barely budged yet. You haven't, like, 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, you know, 20% more reward. They get 10 x the reward or 100 x the reward. It's really dramatic. Entropy, the second law of thermodynamics, this 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 wanna fall apart. And that's the nature of things. If you if you abandon a city for a few months, it starts to go fallow. You know? And so entropy is just this concept that shit tends toward disorder. And the 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, and, like, 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 with product? This is really about effort. The only antidote to entropy, the only antidote to decay in a system is energy. You gotta 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 in and tend to it to make sure it doesn't break. And if you want to achieve greatness, if you want an extraordinary outcome, outcome, and in particular, if you wanna 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 ninety ninth 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 off-site that we do roughly every 18 months, was a reminder that, like, if the 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 fucking dangerous, because if you go to two layers and it's two orders of magnitude drop off in signal and intensity, that is a very dysfunctional organization. So what I said 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 wanna stay at the extreme right end of the power law that obviously governs the outcome of everything that we build. What does that look like to pass along that intensity? Like, 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 out, like, you you cut off your finger. Very best example. Okay. Still got them. I got all 10. I'll give you concrete examples. Actually, the joke that I sort of played on this one when I presented to the 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 the egg? Yeah. Oh, wow. Which, you know, it's like it's just it's funny. And so everybody knows the yellow egg is, like, is Parker. And so the next slide in the presentation was, 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, like, if you know, you know, like, if you ever been dragged into an like, I wanna talk about this fucking problem right now and whatever you're doing, unless it's an interview, like, 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 it's this is how at least I wanna do it, which is, I don't like this. I don't understand this. Tell me why this is this way. You know? Boom. Boom. Boom. Boom. Boom. And people jump in and 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 gotta catch up on today. And and provide feedback to people always in a public channel so that every other product manager and engineering manager can jump in and see know, 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 the reaction from the team that received the message that that you have to you have to inject that energy every minute of every day and that there are no exceptions was not like, oh, that's exhausting. The reaction is, that is so invigorating. So it's, like, so wonderful to hear that we're gonna 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, like, push for the best result. The reaction universally is is like, what a relief that I get to go be intense. Because nobody in a position of leadership wants to be chill. You know? And, like, 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. And, again, this advice comes from where we started, which is this is what success looks like. Because somebody that is less chill than you is gonna find that crack and come after your your market. Is that is that the digest? For 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 we do. So, yeah, if you wanna win, you should probably you should probably try. This is what I always say to people trying to build lifestyle businesses. There's always this idea. I'm gonna build a side business. I'm gonna make recurring income. It's gonna be amazing. And I in my experience, anytime there's a market or something shows up that's juicy and there's ways to make money, somebody's gonna come at you and work harder, raise more money, and there's only so long you can maintain that. Well, man, there's a whole other podcast episode on the concept of leverage. If you sell your time, you've only got twenty four hours a day to give. But if you can create a product that that scales, you know, the the the marginal cost of a unit of that product is zero, like software. It's gonna be competitive, man. Sell your time. It's not gonna be super competitive, but, like, sell that you know, achieve that level of leverage, and it's just gonna there's it's a pretty efficient market. To close out this, threat of intensity and 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. I mean, both those two. Fundamentally, 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 wanna be uncomfortable. Well, that's not how high performance teams operate. So I demand feedback, and I give it. And doesn't mean that when I give feedback, it's not open to being questioned or discussed. I mean, of course, it is. But, like, when I observe something, I try to say it. That's the feedback topic. The the part of this that that has been interesting to me is that people withhold escalate. The customers withhold. Customers don't wanna escalate to me as an executive. Even, like, the 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 wanna 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. Like, no. You went and you found the software that created data error, and then you found the system that created the software that created the dare data error and you solved all of that back to the to the 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 I and I was 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 you know, minor things that are, from the last couple of days from people who who'd had some nits and issues that I'm just like, I've got them queued up on my to do list today, and I'm gonna take them to the product teams directly. 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. For people that are listening to this and feeling like, man, this is so stressful and intense and just, like, I I don't know if I wanna work this way. Give them a sense of just how successful Rippling is. I think a lot of people may not even heard 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? They give people a sense of just how massive this business has become. People look at Rippling from the outside. I think they think of us as, like, payroll and HR or whatever, which is cool. Like, it's it's a bit like saying Microsoft is a desktop operating system company or, you know, it's like every 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, like, 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, like, the the core of every workflow and everything that a company has to do, be it AI or manual traditional GUI based software is, like, 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 is also very important, and, of course, some big business have been built on that primitive as well, but we think the people primitive is actually much more important. And then the only thing that hasn't been done here is, like, somebody hasn't been ambitious enough to build a good business on top of that primitive. Workday is terrible software. Everybody agrees on that. If Workday agrees on that, good luck to them. But, like, 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 primitives. So we're gonna do that. And, we're successful because we deliver on that promise at the scale we're at today. Like, the fact that you can do and this is not this is not a sales pitch or sort of, like, an 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 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 gonna show next year, and it is going to set the standard. It is going to be the most like, 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 gonna create for us. You ask about, like, sort of, 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 so the, you know and, like, the market cap at 16,000,000,000, I think, now undervalues where we are from a revenue perspective by a long shot. There there is just so much upside to to do what we're doing. SaaS might be dead ish in terms of point solutions, but long live SaaS in terms of what we're building. Let me follow that thread. And in AI, there's been a lot of talk about AI is gonna replace SaaS, as you maybe just said. People are gonna vibe code their way to their payroll system, which I you know, good luck to the employees of those companies. And so what I'm hearing here is the the 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 is that the gist? No. I think the gist is is a really good quote. I forget who it's attributable to, but it's, yeah, there's two ways to make money in software bundling and unbundling. And, you just gotta get the timing right. So this is a this is a period of bundling. Point so here's the problem. Point solutions don't have enough data in the age of AI to be useful. You gotta 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 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, you know, there are the 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 s t SFTP. Like, what are they gonna do? What are they gonna do? It's just never gonna work. It's just no way. And so I it's, like, literally have no idea what they're gonna do. They're just not gonna build AI software, I guess. Like, Point SaaS is is sort of in a in a rough salute 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 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 sorry. 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 mine and start refining it. Like, you are in you're in a very difficult place from an economic standpoint because you're not gonna be permitted by either of those parties to build a big business on their backs. This is not how it's gonna work. They're gonna demand value capture that crushes your unit economics. So I look at the the, like, 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 gonna kill off 80 or 90% of the stuff that I I see right now as stand alone AI businesses. So 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? Yep. Because look. SaaS software is a bit flipping all SaaS software applications are bit flippers. Like, it's a it's an interface changing yeah. Changing values in a database is what it does. It's really hard probably. Like, Rippling one of Rippling's superpowers is where a coin sorter. You dump, like, let you know, $20,000 for 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 four zero one k, 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, like, abstracts us a little bit further from having to think because our future is Wall E. It's gonna be great. Speaking of Wall E, actually, I I I have this Matic robot. You have one of these? Mm-mm. It's a it's like a it's a, like, a human it's like a self driving car robot, basically. A self driving car people build this robot that cleans your your house. It's, maybe I didn't mention that. It's like a, house cleaning robot that just, like, goes around. It's like a Rumba. You should get one. They're they're expensive, but incredibly cool. And, actually, in Wall E, if there's a scene where they actually have what basically, what these things look like. Yeah. So it's not so it's not so far fetched to that movie. The direction was actually quite prescient, perhaps with the exception of the gravity defying daybeds. Yeah. I don't know, but that's not good news. You've seen that movie. Oh, man. So on this AI stuff, which is which I'm hearing is you're probably we're gonna see a lot more consolidation where these point solution companies realize they need this data. This is, like, essential, and they're gonna combine and and merge and bundle as you described. It's possible. I am not a part of an investigator on this stuff. I think, like, there's some really interesting investors out there who who I think are thinking quite deeply about this. And in particular, like, I did Conviction, which is, like, Mike Fernall and Sarah Guo. Mhmm. Like, I think those are two investors who are hyper focused on AI. And when they made the decision to sort of take that approach, at the time, I thought, like, as that's kinda narrow. Now I'm like, no. No. No. That was the right move. And and, like, they it just means that they, like, they have a very deep, deep, deep, set of hypotheses that they've formed over the course of of kind of seeing every AI deal in the valley. And, you know, there are better people to ask this question of than I am, and I, and I think if you're an entrepreneur, I recommend them to you because I think they're really smart. Awesome. I love I love those guys. Also, Sarah and a lot have a podcast called No Priors that I'd also recommend. We'll point and see 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 here? They think you're seeing of, like, here's how you need to here's what you need to do to win in an AI company. Oh, god. So much. Like, I actually think that if I were to give you an answer to this question right now, it would be bullshit. Mhmm. Yep. I don't have anything back to my point earlier. I don't have, like, I don't have enough relevant experience in the abstract to, like, dole out on a podcast on that topic, but I, you know, I wish them luck. I love that. The the circling back to your advice, don't ask for advice. Ask for a relevant experience, and I love that that's what your mind immediately went. I'm gonna 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 I mean, it's not a super exciting thing, but I'll say, like, where I use so I like, 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, like, the product quality list and the pickle as something that we've come up with internally, I do turn to, to AI, ChatGPT and Gemini, where I I take, like, 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 wanna communicate. Help me come up with pithy ways to articulate these things. And 80% of what it outputs is trash. It's just, like, sort of middle of the road, average, low alpha junk. But it is a thought partner, a nonjudgmental thought partner, where they in 20% of the stuff it comes out with, I'm like, it's pretty good. That's a new word I didn't think of that does kinda hit the nail on the head for this concept. And so if you if I believe that my job is 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 that ChatGPT and Gemini do a great job of helping me refine how to articulate the concepts that I want to to articulate. They are not useful in coming up with the ideas themselves. That'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. I have not spent a lot of time with Claude. I do I have used it, but by virtue of this conversation, I'll probably go give it a shot. 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. It's always, 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, anything else you wanted to touch on or leave listeners with? We've we've spent a lot of time talking about intensity and the grind and the need to just always be operating at the ninety ninth 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 that it's a negative, that it's maybe not something that you want. And I I think there's a backstop for me that I didn't talk about today that I think I'd I is important to share, which is that life is amazing. That, like, 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, like, if you remember how insignificant we are and all of this is, it brings this levity to what we do and and to the work we put into building this, because this is, like, rip like, Silicon Valley in 2025 is is Florence in the Renaissance. It's crazy. Like, 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 gotta zoom out and appreciate that magic. And so then you turn around, you're like, fuck. I gotta work on Friday night. Right? Like, I I've gotta go give it my all. I gotta go compete in the arena of business. Just you have to you never 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, like, 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. And it's super important as a counterpoint to the intensity that we we talked about. That is beautiful. I think about Pale Blue Dot, Carl Sagan's whole thing. Just stunning photograph that literally changed the way I think about who I am as a person when I saw it. Yeah. Well, going in a completely different direction with that, Matt, we reached our very exciting lightning round. Alright. We've got five questions for you. Are you ready? Okay. Here we go. What are two or three books that you find yourself recommending most to other people? Okay. Two or three books. You you give me a heads up on this. So, like, one 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 Kaufman, 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, like, people in their twenties and thirties 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 Brian 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 and 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, like, 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 nineteen sixties, 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, like, 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 seventy years, and that's that's one of them. Beautiful. I love the first one is you don't have it because you're you're using it with your team Yeah. Constantly. You you mentioned it one point, before we started recording, you have, like, eight copies of that book that you just give out to everyone. Yeah. And we handed out, like, candy. Okay. Is there a favorite recent movie or TV show you've really enjoyed? Yeah. So I'm a little embarrassed by this answer, but I'm gonna be honest. Please. There's a 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, like, just heated rivals on the ice, and it's a huge thing that the the world is watching, but, actually, they're secret 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 it might not be for everybody, but it is a 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 very, it's it's a little chintzy, but it's a lot of fun. It's also really fun to see, like, gay people represented in the media as though they're normal. That's fun. And soon to be on Netflix with the acquisition if that goes through. Oh, yeah. That's crazy. Amazing. Okay. Is there a favorite product you recently discovered that you really love? My Fellow Coffee Maker. I love My Fellow Coffee Maker. It's got an interface that lets you, like, 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, like, it's definitely awesome. And so I have actually, I have one in the office and one at home and one in the garage. Wow. That is a favorite product. You have three of them in in the same cold space. Yeah. Yeah. Oh, no. In the office. Okay. Fellow is also a Ripline customer, and that's, like, a a nice side effect when we get to Have they ever escalated anything to you? No. If you're listening and you're from Fellow, I want to hear all your gripes. Perfect. Two more questions. Do you have a favorite life motto that you find yourself coming back to often in work or in life? It's a dark one, and I'll share this one sort of, partially for the humor of it, but it's it's actually sometimes useful. Immediately, at least, it's sort of a a moment of smiling when it happens. It's like the the model 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're 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 cut might come next. So not not exactly uplifting, but fun to use. Use. No. That is it is uplifting. It's an like, 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 a waste. And it might get there. So it's an insurance 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 DJ voice to give people a sense of Well, it's so first of all, we it's not DJ, Lenny. It's it's radio personality. And, yeah, I used to do the greatest hits of all time with hits from the sixties, the seventies, the eighties, and a little bit of the nineties. 01/00/2015, the hawk. Yeah. It's a 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, the midday segment when, right before I went to college. And what a gift. What a huge gift in my most formative years to have developed, like, an ability to be in front of a microphone comfortably, you know, because here we are. I love for people that weren't watching this YouTube, you, like, lean really close to the mic to get that to get that, radio personality voice. Yeah. You gotta be able to hear, like, the saliva in the mouth. Incredible. And it's like the same person talking. Like, 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. What do you is there something you wanna plug, point people to, and how can listeners be useful to you? Look. My life is rippling. I point people there, and that's this is my life's work. It's gonna be, it's gonna be a banger, so stay tuned. And, and the way that you can help me is that if you're a customer, you gotta tell me when you have problems because that's how we get better. What's the way they get to you? Is there any place you wanna point people to? DM me on Twitter is easy at Stay Nine. You can email me my last name@Rippling.com, And, I'll go that far without giving out my phone number. How's that? Perfect. The perfect boundary. Yeah. Matt, thank you so much for being here. It's my pleasure. Thank you for having me, Lenny, and, congrats on all the success with this podcast. It's been great. Same to you. It's always a good sign at the end of a conversation. We're like, oh, I gotta get me some of that stock of that. Gotta get into that rippling. So It's a good buy. For sure. Recommended by the guy. Yeah. But you're, you know, hard to hard to get. Very. Alright, man. Thank you so much. Thanks. Thank 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 lenny'spodcast.com. See you in the next episode.