Lenny's Podcast: Product | Career | Growth - 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Starting point is 00:00:00 It is really important to me that we feel that we've deliberately understaffed every project at the company. If you overstaffed, you get politics, you get people working on things that are further down the priority list than necessary. That is poison. It's wasteful. It slows you down. It creates cruft. 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 want to be in the 99th percentile in terms of outcomes, it's going to be. to be really difficult. You've got to sort of remind people that if they ever find themselves

Starting point is 00:00:33 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 while 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

Starting point is 00:01:12 to be an order of magnitude drop off in intensity. That is fucking dangerous. As an executive, as a leader, your job is to preserve that intensity at its highest possible level. You've had a couple really interesting experiences with your own startup. We talk in Silicon Valley about never quit, but that is complete, absolute venture capital 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 billion. They have over 5,000 employees, and Matt has been instrumental to that success. He's also got a really rare combination of brutal honesty,

Starting point is 00:01:54 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 Strauchim and Seneel Rahman 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. And if you become an annual subscriber of my newsletter, you get a year free of 19 incredible products, an entire year of lovable, replet, bolt, gamma, aneta, and linear, Devon, Post, Hog, Superhuman, Descript, Whisperful of Perplexity, Warp, Grinola, Magic Patterns, R-Cash, Jap, R.D, Mobbin, and Stripe Atlas.

Starting point is 00:02:40 Head on over to Linney's newsletter.com and click Product Pass. With that, I bring you Matt McGinnis, after a short word from our sponsors. This podcast is sponsored by Google. Hey folks, I'm Amar, product and design lead at Google DeepMind. Have you ever wanted to build an app for yourself, your friends, or finally launched that side project you've been dreaming about? Now you can bring any idea to life, no coding background required, with Gemini 3 in Google AI Studio.

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Starting point is 00:04:15 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.cue.com slash Lenny. That's datadoghqq.com slash Lenny. Matt, thank you so much for being here and welcome to the podcast. Thank you for having me. I'm going to start with something that I know is really important to you, something you talk a lot about, that I don't think people hear enough on podcasts like this, which is that extraordinary results require extraordinary efforts.

Starting point is 00:05:00 Talk about why this so important, what you think people need to hear. 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 achieved whatever officer. You have to apply the same frameworks and concepts to get people to achieve goals together.

Starting point is 00:05:40 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 want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. Like, it's going to be really uncomfortable. And you've got to sort of remind people of that, that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. 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 percent. true that it is necessary. And so I do use that framework as a sort of guiding principle in my own

Starting point is 00:06:22 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 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,

Starting point is 00:07:08 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 to say to a company like Rippling 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 revenue foundation that we have is extraordinary, like really, really compelling. And it gives you as a leader the air cover to get up in front of your team and say, hey, guys, I need the last ounce of oil that you've got left. And if your company's not growing very quickly, if things aren't that great, if your growth rate is 30% or 40%, 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 going to yield much. And so extraordinary results, outcomes demand extraordinary efforts. But if there's no chance at an extraordinary outcome, it's very hard to get the extraordinary.

Starting point is 00:08:11 effort. And so I like to remind people at Rippling, at least, 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 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 ringing the oil out of somebody who's in the bored and tired zone. I saw the same thing actually at Airbnb with Brian Chesky. It 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?

Starting point is 00:08:53 How to 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, as soon as you shipped one version of the iPhone, like you were just immediately thrown into the pit of building the next one. And there was no break. It was just relentless.

Starting point is 00:09:20 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 going to go fill that crack. And so you have to be relentless. There can be no relaxation of the organization.

Starting point is 00:09:44 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. You can't grind the individuals down. But the team as a collective group of people has to be sort of on the ball all the time. There can't be a break. And if you leave one, you're just begging for the, the slightly more hungry competitor to come in eat your lunch. And, you know, that's the beauty of capitalism. Also, very

Starting point is 00:10:12 counterintuitively, and maybe the more optimistic perspective here is when you do give your team space to just twiddle their thumbs, bad things start to happen. Morale actually dips in my experience. People get distracted. They're like,

Starting point is 00:10:28 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, the moral actually goes down in those experience, 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

Starting point is 00:10:57 for when you're going to ship something. But of course, you have to set some default. So you make your best guess, and then you manage to that best guess, and you learn as you go, because in software development and in business in general, everything's emergent. These are not things that are knowable top-down or a 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 oversteering or understeering relative to your perceived midpoint 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.

Starting point is 00:11:39 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 ranked list and like you know that you got to do the top five. But the next 15 down, it's 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. poison. It's wasteful. It slows you down. It creates cruft. And so it's very clear that understaffing

Starting point is 00:12:07 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 Ripley. 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 to forget who this was. They use this metaphor. If they want their team to be dehydrated, to always be wanting more water. And then eventually they're too dehydrated. Okay, we need someone to help. Interesting.

Starting point is 00:12:52 Yeah. There's a line along the lines of extraordinary efforts. I want to make sure I read because I think this is really good. This may be a way to summarize what you're saying that good teams get tired and that's when great teams kick the good team asses. Yes, this was a quote actually from Sineel and he found it from a women's basketball team coach. And it is, it is to my point earlier about like you got to run the engine 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 going to 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 going to carry it to the grave. It's like you're here to do this stuff because it somehow fulfills you while you're on the planet. And I love the sport of business. And I find that sports, notwithstanding the fact that I watched very little of it, is a very, that military, you know, those are very ripe sources of parallel concepts to apply in leadership.

Starting point is 00:13:56 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 feel that. So I think that's a really important component of this is you need to be winning and succeeding.

Starting point is 00:14:23 I mean, one thing that I've learned from Parker is, Parker's our CEO, Rippling. He, you know, he said, you don't really learn from your mistakes. You learn from your successes. And it's like, you do, of course, and he would admit you learn a bit from mistakes. But I do think that this is sort of feel good bullshit that, you know, it's like, well, you know, you didn't succeed, but, you know, at least you learn 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.

Starting point is 00:15:04 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 you're going to get on an airplane and one maintenance technician has seen it done right a hundred times and the other maintenance technician has seen it done wrong a hundred times, but he learned from his mistakes.

Starting point is 00:15:33 Like it still hasn't had any success himself. I mean, give me a break. There's not even a comparison, which plane you're going to feel more comfortable on. And so I do think that like learning from your mistakes thing is a bit of a feel good trope that actually has very little substance in reality. And it's why as an early career product manager or it's why like, frankly, at any stage of your career when you want to learn, you should join a winning team. Like it's cool to go and start a company at 22.

Starting point is 00:15:59 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 want to interview that candidate because I want to hear what they learned from being part of a winning team. And that's sort of one of my go-toe churistics when I'm looking at candidate profiles. And I think it's an undertold trope. Sorry, not an under-told trope.

Starting point is 00:16:28 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 C.O. is moving into product. Let me ask you why that,

Starting point is 00:16:54 why did you move into that role? I feel like you've been killing it at C.O. Maybe that's the reason. Be careful what you're good at. And also just what are some surprises about this, about moving into product, because a lot of people imagine what it's like, and then you're actually doing it.

Starting point is 00:17:07 The story at Rippling is pretty interesting. and I'll tell it because I think it explains why I'm making this transition, but this isn't really about me. I think it's sort of a pattern that your listeners would find useful. In general, your best executives are the ones that you can mostly toss into any challenge and they will bring order to chaos. They will fix the thing. And I do appreciate the terms that people have used at rippling for me, you know, talking about McGinnis's injured birds, where at any given moment, some function is in disarray or in jeopardy and I go and focus very carefully on that function to get it back in order, batting 800 maybe, you know, like not always wild success, but

Starting point is 00:18:02 I did that anywhere except R&D. I would be where, 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. But it never R&D. And so 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 going to go in and deal with that. And, you know, the smoke takes various forms and when you're growing as quickly as Ripling is growing, it's not always something that necessarily even impacts customers, but it's the sort of thing where you're like, fuck,

Starting point is 00:18:43 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, uh, in product hiring and, uh, a lot of us had to sort of pitch in. And Parker and I sort of stare at each other, uh, through two years of this kind of disarray or this chaos or this agony of things and just never really having good

Starting point is 00:19:21 executive leadership over both engineering and product at the same time. And I remember Parker 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 gigs up. I'm going to go do it. And he really sprung a, up and it sees like, 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 going to do it and express that to Parker in December. I really took it on in January of 25. And so it's been 11 months of learning. Jumping into the product role when the product function itself, although staffed was really talented people wildly under understaffed. And

Starting point is 00:20:03 without a single spiritual leader on top of it to drive consistency and process excellence, had become locally optimized but globally incoherent. And if you know Conway's law, you are destined to ship your org chart. And so with a locally optimized globally incoherent team, you had a locally optimized globally incoherent product experience that needed to be resolved. And so my efforts over the last 11 months have been to establish. 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 clean

Starting point is 00:20:43 up on aisle three that needed to be done, even though a lot, again, a lot of the people in the, team are quite talented in doing an excellent job of managing their specific domains. Jumping into the product role has been like quite eye-opening. I feel a little bash. 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,

Starting point is 00:21:30 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 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

Starting point is 00:22:18 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 answer is 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 here. To dig into this a little bit more, was the big lesson and kind of eye-opening moment that

Starting point is 00:23:05 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 lesson there? The lesson is that everything must be done in its time and order. And you can move really, really quickly. You can, there's no sort of excuse not to move with urgency on all of these things, but you got to do them in order. And you have to, you have to lead bottom up. Like you got to lead from the specific circumstances you observe.

Starting point is 00:23:47 And I think for me, one of the best things that's happened over the last 11 months is that I've gained a greater trust in. my own instincts, that the sort of patterns I've matched across other functions do indeed apply in product, but I have both of the advantage and disadvantage of not having led a product function before and therefore must think about every problem from first principles. I have no choice. I can read shit on the internet. I can listen to clear thinkers on topics and import their ideas, but I'm very reluctant to import an idea without breaking it down into its constituent parts and figuring out how

Starting point is 00:24:28 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. point. It's very well instrumented. It's got like very happy users. It's got an awesome growth profile. And so we should we should be really focused on the adoption metrics because I think that's going to be an important ingredient to low churn over time. You know, removing friction

Starting point is 00:25:10 from the implementation process as an example. There are other parts of our product where I would say I don't care at all about adoption and am much more focused on foundational things like I said earlier test coverage or whatever just to make sure that the thing is stable and good and delivering exactly what it's supposed to deliver once it's adopted. 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 here need to understand

Starting point is 00:25:41 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&P 500, if that's your benchmark. So alpha is the outperformance relative to the index. And then you have the concept of beta.

Starting point is 00:26:13 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'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.

Starting point is 00:26:37 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. And you also have low beta people who are also very valuable people. Dennis Rodman basketball player, nut job, very high alpha. And there's room on every team for one. Dennis Rodman is a favorite of mine. It's like you can have one difficult employee who's got a ton of upside. 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.

Starting point is 00:27:22 So when you're building a product from zero to one, you're probably pursuing alpha. You're looking for some angle on this market or this customer problem where the product is actually going to provide an outsized return relative to whatever the default solution is. When you have a more mature product or if you have somebody in the product operations group, 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, you badly want the pay. payroll product to be very low beta. We really don't want the payroll product to have any

Starting point is 00:27:50 unpredictability or aberration. And so we're willing to accept more process. And here's a fundamental principle of design in an organization, which is that processes, processes in a business exist for the sole purpose of lowering beta. Processes are for decreasing volatility in the output of the system. The downside of a process is that it suppresses alpha. And you have to be super, super careful and judicious in the application of process in the product team to know that you're lowering beta in the places where you want to do that without suppressing alpha in the places where you need it. And so as we've gone through the last year of reforming the way that we build product at Rippling, it's been a game of recognizing those places where I need to implement

Starting point is 00:28:45 a touch of process, just a touch. Other places where I need to implement a very clear, rigid process where I don't want alpha. I just want low beta. So examples of this are, let's say, our product quality list, which we lovingly at Ripplin called the pickle. White pickle. Yeah.

Starting point is 00:29:01 So it's actually a really important thing. I think if you want to bring about cultural change in a team, like look, we have, we have 1,300 people in our R&D organization. It's a big ship that we have to steer. If you want to create a moment that sticks in people's brains and sort of becomes a zeitgeist or something that they latch on to, you got to create an entity, a vessel for meaning, and then you got to fill that vessel with your meaning. A meme, you might say. Yeah, well, sure, a meme. Like a meme is actually a good example of this in common culture.

Starting point is 00:29:29 I, in pop culture, I think, like, it's why when people come to the table with ideas from the outside, I welcome those outside ideas. but the first thing I ask the person to do is to tell me what they mean without using those words. So when someone comes in and says, hey, I want to do this thing on strategy. I'm like, cool, tell me what you mean without using the word strategy. And it forces them to break it down into its constituent parts. And if they can articulate it clearly without using that word, I know that they know what they're talking about. And if they just fumble around with the word strategy again, I'm like, okay, you actually haven't thought this through. And so with the pickle, with the product quality list, it's like I could come up with some generic term for this.

Starting point is 00:30:06 but I really want a new joiner at the company to understand it. This is an idiosyncratic thing to Rippling. This is unique to us. You want to understand this thing. I also want it to become a component of common parlance in the day-to-day work of the product management and engineering teams. 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.

Starting point is 00:30:30 And so we have a product quality list. And the product quality list is lightweight in the sense that it just, articulates in the simplest ways the standards we want you to meet when you ship a product. It doesn't apply to every product, not every line applies to every product, but it's comprehensive, and it provides me with a framework for iterating over time as we learn. And so just yesterday, we shipped a 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.

Starting point is 00:31:00 If you're not aware, Parker is the sole payroll administrator for Rippling for all 5,200 employees. personally runs payroll always. There is no exception for all 5200 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 going to install for ourselves because we dog food the hell out of everything we build. Yesterday, he goes to install this new application. We're about to ship a new app for feedback, allowing people to give one or other feedback in their companies. And he installs it and he goes in and it dumps them onto an empty screen. And he's like, what the fuck is this?

Starting point is 00:31:37 What is this? What's going on? Like, hey, wow, talk about fail. So I chop another one of my fingers off. I'm down to nine. And I'm like, what did we miss? What we missed was there was a fucking feature flag, fucking feature flag. And I'm just, I'm not allowed to say feature flag

Starting point is 00:31:54 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 a little shim. 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

Starting point is 00:32:16 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 asked the question how do we miss this in the factory 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

Starting point is 00:33:03 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

Starting point is 00:33:39 word we're going to call a pickle? Product quality list. Product. Okay. Okay. Okay. Okay. P-Q-L, which, how could you pronounce it other than pickle?

Starting point is 00:33:49 I'm imagining all your decks have a 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 Picklerick. Do you get that reference? This is a Rojack test. Okay. So this high alpha, low beta, I love this concept. So the idea is depending on the team, depending on the problem, we need a high alpha, low beta person or actually okay with a lot of variants for this specific project. Yeah, we're willing to accept a bunch of volatility in this area in exchange

Starting point is 00:34:18 for the upside we get from the creativity and risk taking of these people or the lack of process that sort of gives them the latitude to do what they want to do. And so when you're hiring, you're looking for again. Is this person in low beta or not? 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 talking about hiring for a second, I think, I've spent a lot of time with teams at

Starting point is 00:34:46 Rippling talking about how I hire. And it is born of batting practice. Meal, you know, I'd be super interesting to actually be able to rewind the tape on my life and sort of contemplate how many candidates I've met in every context, many thousands, maybe tens of thousands, I don't know. It's a lot of batting practice and a lot of model training in my brain. And so I rely a lot of my intuition, which, of course, HR people say you're not supposed to do. That's complete bullshit.

Starting point is 00:35:12 If you have a good intuition, you should absolutely rely on your intuition. And what you have to do after you have a reaction to a candidate when you're looking at hiring somebody is you need to decode your intuition so that it can be. be expressed to other people productively. And so one of the frameworks that I use for this is Spotak. It's a very ugly acronym. There's a hat tip to somebody out there in the universe who originally thought of this is not me, but I adopted it.

Starting point is 00:35:38 And it's that people are smart, passionate, optimistic, tenacious, adaptable, and kind. Those five things. Six, can't even count. I told you I lost a finger, right, when I made a mistake. So it was down one. Nine to go. Spotak. isn't by itself a good top-down framework,

Starting point is 00:35:59 but when you're thinking about, oh, why did I not, why did this candidate just like, why did it not click? Why do I not like them? You go down the list, you're like, oh, yeah, I know, this person, it's that they were not excited about the idea. They weren't passionate.

Starting point is 00:36:13 You know, it's like, it's that they talked shit about their previous manager and that they were a victim of the performance of their last two companies. That's what it was. They're not optimistic. You know, the framework is super useful to evaluating people.

Starting point is 00:36:26 I think 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.

Starting point is 00:36:49 You're speaking to this audience, frameworks, frameworks, frameworks. Yeah. So high alpha, low beta, sometimes high high. Betas okay, Spotac. In hiring, is there anything else that you find releaseful 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

Starting point is 00:37:18 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

Starting point is 00:38:09 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, and, like a lot of the sort of basic human interaction models. I, you know, you never think that like giving someone an impossible task and even including the L5 person versus the VP on the same thing would be productive. And let's just say our recruiting team still sort of kvetches a bit about this and feels like we eliminate people too aggressively at this stage of the interview process. But I've found the wisdom in it and think it's actually quite useful to give everyone the same simple,

Starting point is 00:38:47 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 going to get all the way through the wall. It doesn't matter. You're going to learn a lot. And I've found that to be kind of an eye-opening new thing for me that has been fun. I mean, look, the joy of product and the joy of product management and the joy of being part of product.

Starting point is 00:39:08 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 magic of product management is that you kind of have to, you know, we talk about 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 got to be really good at working with other people. You've got to be good at communications and articulation. You've got to be good at project management. You've got to 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 tippity top of the smartest and most polymathic people in the industry.

Starting point is 00:40:01 I'll say one other thing about what I love about leading product, which is as a C-O, my job was to accept the product as it was and optimize everything around that. my job was to make sure that the product operations, in our business, the interface to the insurance carriers, the interface to the payment entities, the government regulators, that stuff all just sort of worked. It was to make sure that our sales engine, our marketing engine, all the go-to-market stuff optimized itself around what the product was. It was about recruiting and making sure we got people into work on the product. You kind of go down any function that isn't in R&D, and I had some hand in trying to figure out

Starting point is 00:40:41 how to make that function work to the best of its ability given. what the product was. And now that I lead product, I'm like, oh, wow, this is the high order bit. Not that I didn't sort of understand that, but like now I really get that product is the high order bit. If you get the product right, it fits in the market, everything else gets easier. Finance is easier, sales is easier, marketing is easier, recruiting is easier. Everything gets fucking easier.

Starting point is 00:41:11 And so I think the other joy of leading the product function is that, you know, 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 challenging this work isn't just how awesome PMs are. You know, as you know, a lot of people are a very anti-product manager.

Starting point is 00:41:46 Why do we need product managers? We don't need them. Just let everything down on 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 love wine. Wine's one of my things.

Starting point is 00:42:00 And I've learned a lot about wine. And one of my favorite lines is like, I don't like Chardonnay. And I'm like, no, no, no, no, no. Chardonnay is the most fucking amazing varieties of wine in the world. You just haven't had good Chardonnay, you know? And there's a shardinet there for you. Product management is like, you don't like product management. You think product managers suck.

Starting point is 00:42:19 It's like, well, you just, you just haven't had a good shardinay yet. Once you have one, once you have one, you know, you can't unlearn it. Let's find that PM ASAP. No, let's find that shardinay. But that PM with some shardinay. You touched on this product market fit point and I want to double down on this thread. You've had a couple really interesting experiences of struggling to find product market fit with your own startup. You said he worked on it for nine years, you said? Okay. And then with

Starting point is 00:42:48 Rippling, complete opposite, extreme product market fit up into the right. What's something you've learned about just that, that you think people maybe don't understand about what it feels like, what it takes to get to product market fit, how things change. There's a line that this venture capitalist whose name I will not mention said, which was, you know, that product market fit is a sort of thing where you absolutely know it when you see it. And therefore, if you don't absolutely know it. You don't have it. And this kind of gets back to my point about learning for mistakes versus successes. It's like, ah, man, over and over again, over the course of the many years that I spent at Rippling, sorry, inkling, we thought we had it. We thought we had product

Starting point is 00:43:30 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 was, 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 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, you know, and I read the updates from them that I sent to my investors in 2011 and 2012.

Starting point is 00:44:24 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.

Starting point is 00:45:11 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. We're going to be on the planet. I mean, the average age of a man in the United States when he dies is something in the mid-70s. Like I got 2030, maybe if I'm lucky, 40 years left on the planet, very conscious at the time that I have.

Starting point is 00:45:34 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 beautiful one. 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

Starting point is 00:46:10 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 uh 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 incentive. Everybody's acting in accordance with their incentives in Silicon Valley. The executives, the founders, the venture capital. 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 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

Starting point is 00:47:22 of the people who don't. Or at least it is the easiest prey for the incentive structures. Not for venture capitalists as individual people who are beautiful and wonderful, all of them, which is really wonderful people. 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, VC's like, I'm always just like, hey, let me know when you're starting your next thing, I'm excited to invest. They're rarely, unless they're not a great VC, the rarely are they just pissed at you for like, how could you possibly not make this work? 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

Starting point is 00:48:01 the seed investing game, your forecast is zero. Your assumption on every investment is that it's going to go to zero. Any seed investor who doesn't take that stance is off the rocker anyway. You know, they're a very bad investor. Seek investors who play the long game, who want to be in your second and third company and are willing to take a bet on the first one and let it go to zero so that you can get on with stuff. 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. I want to tell you about a new DAF product that GoFundMe just launched that makes year and giving easy. GoFundMe giving funds is the DAF or donor advice fund, supported by the world's number one

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Starting point is 00:49:18 Start your giving fund today at gofundmeet.com slash lenny. If you transfer your existing DAF over, they'll even cover the DAF pay fees. That's gofundme.com slash Lenny to get started. This begs the question of just when is it time to quit? You know, if people hearing this might be like, oh man, like what are some signs that, okay, It's time to wrap it up. Here, look, history provides us with a clear guide.

Starting point is 00:49:40 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,

Starting point is 00:50:14 product market fit. Like I said earlier, it's super clear. And so if I were to pick a number out of a hat just from my lived experience, I think it's very important. One aside, don't ask people for advice. Ask people for relevant experience. If you ask them for advice, they will always give it. But if you ask them for relevant experience,

Starting point is 00:50:35 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 my own entrepreneurs when I work with them. It's like, let me offer you whatever relevant experience I have. And my relevant experience on this topic of when to quit is like, I think we could have called it after the second or third pivot, which was somewhere around year four. It is, of course, very important to believe in what you're building and to be, you know,

Starting point is 00:51:05 like to be persistent. But there is definitely no shame in saying, look, we pivoted once or twice. It's not catching. I got to 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, riproaring growth story, it's extraordinarily difficult. This is so extremely rare. So beyond even already the rare scores you're going to, you know, face from the out. outset that that that now is is going to convert to something crazy.

Starting point is 00:51:39 So that's hard to hear, I guess. But man, it can be really liberating when you're like, fuck it. I'm going to do this. I have the energy. I'm going to do it again. I'm just going to do with a clean sheet. That is really helpful. You have this really fun way of describing product market fit around receptors and drugs.

Starting point is 00:51:53 Oh, yeah. Yeah. This is like a really fundamentally misunderstood dynamic. When I, when founders message me and they're like, hey, like like my LinkedIn post and my tweet for this launch. I do it. I retweeted. I like it, whatever.

Starting point is 00:52:11 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 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.

Starting point is 00:52:34 launches amount to the teeniest thimble of water in the ocean of noise about startups and companies. And so you just got to build it brick by brick bottom up and these launches don't really amount to much. And so how do you think about that? 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 going to have product market fit? Well, if you recognize that the market is immutable, no amount of tweeting, LinkedIn, posting, posting, advertising, is going to change whether the market wants your product. It might raise awareness about your product,

Starting point is 00:53:10 but it's not going to change whether somebody wants it. Then you take a different mindset. You have to view your startup as running an experiment in the universe to see what you get in return for that. And this analogy of drug discovery and binding receptors is like nobody at Genentech thinks they can market their way to better performance inside your body. The binding receptors for that drug,

Starting point is 00:53:34 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 going to latch onto your product and rum 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. 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

Starting point is 00:54:14 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 a inspired bike because it's extremely, extremely rare. Let's talk about alpha beta again. Okay. As an investor, you might build a checklist of things you want to make sure are true or false about a company and hope that that's going to yield the kind of like investment success you're looking for.

Starting point is 00:54:45 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. 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

Starting point is 00:55:06 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, 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 Not Not Not Motion. You can't replicate it because it's not 2010 when they started the company.

Starting point is 00:55:52 Do the math on that. Or 2011, actually. These guys stuck with it. They went through hell. They pivoted. They went to Japan and sat in kimonos and meditated on what they were going to build. And by hook 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.

Starting point is 00:56:24 Carving out your own niche in that market is just. unthinkable. And so I look at notion as having succeeded by virtue of the narrative violation of persistence. I don't think is a good idea for very many people. It happened to work for them. And I look at it as being a function of the founding team. And their specific idiosyncrasies, the absolute insistence on craftsmanship from Ivan, this is him. That's his thing. The takeaway lesson is not give up or don't give up. The takeaway lesson is certainly not go do what Notion did. The takeaway lesson is that every company succeeds on the foundations of the idiosyncrasies of the founder. The idiosyncrasies of the founder. Ripling succeeds for almost the polar opposite reasons

Starting point is 00:57:17 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.

Starting point is 00:57:50 and I want to ask another question around investing. What are some other companies you invested in early? First of all, okay, so I sort of hate the question. Like, what are some other companies you've invested? It's a fair question, but the problem is, like, I'm going to give you a bunch of companies I've invested in that won. You know, that are like really notable. So what I would like to do instead of answering that question is, I'm going to give, here, let me give you some like some bait. Like I was one of the first investors in Notion.

Starting point is 00:58:16 I was perhaps the first, I don't know, ask Ivan, clever, which had a great egg I was one of the first investors in Xenifetz, if you've heard of it. I was before I joined, one of the first investors in Rippling. And then more recently, invested in, here's a funny one, I was one of the first investors in deal, if you've heard of them. I was able to exit that position and then, you know, hopefully that company's going to zero with their criminal behavior. but whatever. I was, but more recently,

Starting point is 00:58:51 like, if you know, like Decagon, which is doing some really cool stuff on the AI front. Killing it. I'm in Langchain. Like,

Starting point is 00:59:02 great. So those are some companies that you maybe have heard of. But like, how about like, I invested in macro. The founder was Derek Lee. Macro's out of business.

Starting point is 00:59:10 I invested in debrief. Ned Roxton. It's out of business. You know, I invested in verb data with David Hertz. It's out of business. I'm reading from a list.

Starting point is 00:59:17 I invested in what's the number of 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

Starting point is 00:59:32 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 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 have invested in is a long list and I love to give you

Starting point is 00:59:52 names of companies that don't exist anymore because it's self-serving and a horrible survivorship by us to just list the good ones. I love that answer. I think you're being modest in the context of your hit rate is clearly very high. Even one or two incredibly successful companies out of 70 is a win in VC. And so you're doing very well. But I think that's a really important perspective. When you see people's logos on their websites of all the companies they've invested in. You have no idea how many they've, how many had bats they've had to get those. 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, no, I'm not actually, okay. Well, I obviously like, you know, we don't spend time on it, but I think it's

Starting point is 01:00:33 actually a very good question. Yeah, like, what are some of your fail, well, your best failed investment? 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 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.

Starting point is 01:01:20 And so, like, power a lot distributions happen everywhere. It explains why so few people control so much wealth. It explains why Steph Curry is just so vastly better than the next guy down on the list on the basketball team. It explains why populations are concentrated into a relatively small number of megacities in the world. It's like power a lot distribution just plays out everywhere. And, like, once you see it, you can't unsee it. 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

Starting point is 01:01:54 not the case. And the implications are profound. It's like if you build something to 80 or 90 percent, the Y axis is 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 percent, the top 5 percent don't just get 10 or, you know, 20 percent more reward. They get 10 X, the reward or 100x the reward. It's really dramatic. Entropy, the second law of thermodynamics is a very simple concept. It's the reason your sock drawer becomes messy. It's the reason that potholes form. It's the reason we have to put so much energy into maintaining the aircraft we fly to keep them safe because they really, really, really want to fall apart. And that's the nature of things.

Starting point is 01:02:38 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 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 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 product? this is really about effort.

Starting point is 01:03:16 The only antidote to entropy, the only antidote to decay in a system is energy. You've got to inject energy. So if you have a code base, every line of code that you add to that code base increases the entropy of that system and demands ever more energy from human beings to go in and tend to it to make sure it doesn't break.

Starting point is 01:03:39 And if you want, to achieve greatness, if you want an extraordinary outcome, and in particular, if you want to be in the top 10%, top 5%, on the X axis, so that the Y axis is through the roof, then you have to relentlessly inject energy at every single step of the game. Teams will, sadly, but because we are all human, teams will always optimize for local comfort over company outcomes. Not because, they get together and think we should do that, although unions do do that unequivocally, deliberately. But even in a collection of product managers or engineers, what's going to happen over time is entropy is going to creep in and people are going to optimize for local comfort.

Starting point is 01:04:28 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 feed of the product manager or the engineering manager, every time in public, preferably. It means that every time someone comes to you to hire someone and says that they have skipped the back channel, every time, you're like, you can't hire this person unless you do the back channel. It means that when you get into the board and tired zone on any process, that you as the executive have got to demand the 99th percentile of energy because otherwise

Starting point is 01:05:14 entropy creeps in and the system decays. You have to do this. One of the messages that I delivered recently at our big executive big, like our top 75 manager offsite that we do roughly every 18 months, was a reminder that like if the purest form of ambition and the purest and most intense source of energy in the business is the founder's CEO, that every next concentric circle of management beyond the founder's 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

Starting point is 01:06:06 of the CEO, it's that you need to absolutely mirror that intensity. There are plenty of constituents in the business around you who will advocate for relaxing. There is an infinite supply of people under you who will buffer other team members from the intensity of the demands. Your job is not to be one of those buffers. Your job is to preserve that intensity at its highest possible level and let the buffering happen somewhere else. And that's the point is that entropy creeps into the system insidiously and slowly over time off your radar and you have to maintain that intensity every minute of every day to try and fight it if you want to stay at the extreme right end of the power law that obviously governs

Starting point is 01:07:00 the outcome of everything that we build. What does that look like to pass along the intensity. Like, what does that feel like? What does that look like? So say, Parker comes to you. Those bugs sucks. I got this broken screen. You cut out, like, you, you cut off your finger. Maybe that's the 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 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 which you know it's like it's funny and so everybody knows the yellow egg is like is Parker and so the next slide in the

Starting point is 01:07:51 presentation was boop bo bo bo boop boop which is the sound that slack makes when someone calls you and it was Parker Conrad as 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've ever been dragged into it, like, I want to 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, but this is how it's, this is how at least I want to do it,

Starting point is 01:08:30 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, and people jump in and respond. The factory inspection process that I mentioned, which is where at the end of the assembly line, I jump out with the pickle, and we talk about all of the elements. You have to record a loom of every major flow through the product. I personally review every one of those flows. I've got to backlog. I've got to catch up on today. And provide feedback to people always in a public channel so that every other product manager and engineering manager can jump in and see, you 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 from the team that received the message that you have to inject that energy every minute of every day and that there are no exceptions. It was not like, ooh, that's exhausting. The reaction is, oh, that is so invigorating. It's like so wonderful to hear that we're going to achieve these great outcomes, or at least we have a shot. 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

Starting point is 01:09:43 intense because nobody in a position of leadership wants to be chill. And like, what's worse than a chill boss? 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 chill doesn't accomplish shit be intense 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 going to find that crack and come after your your market is that the digest for sure i mean again if you're chill and you move the x-axis down to 10 or 20 points, the Y axis collapses. It doesn't just drop 10 or 20 percent.

Starting point is 01:10:32 The Y axis collapses. And this is just kind of true in everything we do. So, yeah, if you want to win, you should probably try. This is what I always say to people trying to build lifestyle businesses. There's always this idea. I'm going to build a side business. I'm going to make recurring income. It's going to be amazing.

Starting point is 01:10:52 And in my experience, anytime there's a market or something shows up that's juicy and there's ways to make money somebody's going to come at you and work harder raise more money and there's only so long you can maintain that well man there's a whole other podcast episode on the concept of leverage if you sell your time you've only got 24 hours a day to give but if you can create a product that that scales you know the the the marginal cost of a unit of that product is zero like software it's going to be competitive man sell your time it's not going to be super competitive, but like sell that, you achieve that level of leverage and it's just going to do it's a pretty efficient market. To close out this thread of intensity and adding energy to

Starting point is 01:11:36 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. Talk about 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 want to be uncomfortable. Well, that's not how high

Starting point is 01:12:17 performance teams operate. So I demand feedback and I give it. And it doesn't mean that when I give feedback, it's not open to being questioned or discussed. I mean, of course it is. But like when I observe something, I try to say it. That's the feedback topic. The part of this that has been interesting to me is that people withhold escalate, like customers withhold. Customers don't want to escalate to me as an executive.

Starting point is 01:12:44 Even like the founders in whose businesses I have invested who use Rippling are reluctant to hit me up when something goes wrong because they don't want to bother me. but it is 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 escalation's 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.

Starting point is 01:13:28 Not like throw away the word root cause. Like, oh, we fix the data error and shut the ticket down. Like, no, you went and you found the software that created the data error. And then you found the system that created the software that created the data error. And you solved all of that back to the top. Escalation seems like extremely good at that at Rippling. So we have sort of a dedicated little team that does this for us. Escalations are a gift.

Starting point is 01:13:51 And I, and I say, 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 have, you know, minor things that are from the last couple of days from people who, who have some nits and issues that I'm just like, I've got them queued up on my to-do list today and I'm going to take them to the product teams directly. 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 don't know if I want to work this way. Give them a sense of just how successful rippling is. I think a lot of people may not even have heard of rippling. A lot of people are like, yeah, it's doing great. What are some things you can share that are public or not public? They do.

Starting point is 01:14:49 give people 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 on 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 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 data where we think we're taking things. It's like we really do believe that like the core of

Starting point is 01:15:24 every workflow and everything that a company has to do, be it AI or manual traditional gooey-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 businesses have been built on that primitive as well, but we think the people primitive is actually much more important. And 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. Workday agrees on that. Good luck to them.

Starting point is 01:15:53 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 primitive. So we're going to do that. And we're successful because we deliver on that promise at the scale we're at today. Like the fact that you can do, and this is not a sales pitch or it's sort of like an advertisement for Rippling, I just think it's important to sort 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,

Starting point is 01:16:30 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 going to show next year. And it is going to set the standard. It is going to be the most, like the backflips 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

Starting point is 01:17:17 excited about the tailwind this is going to 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 RIPLINK. We're less than 1% of the market. And so the, you know, and like the market cap at 16 billion, I think now undervalues where we are from a revenue perspective by a long shot. There is just so much upside to to do what we're doing. Sass might be dead-ish in terms of point solutions, but long-lived 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 going to replace SaaS.

Starting point is 01:17:54 As you maybe just said, people are going to 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 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, you need to to do a lot of things for people, for them to continue to pay for your software. Is that the gist? No.

Starting point is 01:18:18 I think the gist is a really good quote. I forget who it's attributable to, but it's, you know, there's two ways to make money in software, bundling and unbundling. And you just got to get the timing right. So this is a period of bundling. Points. So here's the problem. Point solutions don't have enough data in the age of AI to be useful.

Starting point is 01:18:41 You've got to be able to provide the AI with a lot of content. 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 biggest HCM software company you can think of integrates to the other biggest. payroll software company you can think of through flat files via SFTP. Like, what are they going to do? What are they going to do? It's just never going to work. It's just no way.

Starting point is 01:19:25 And so I literally have no idea what they're going to do. They're just not going to build AI software, I guess. Like point SaaS is sort of in a rough spot, especially when you cleave two really important systems apart and say they have to integrate. It's very, very hard. The other thing that I would say about the world of even just like not SaaS but AI software, that point solutions in the AI world are also in a rough spot for the same reason. It's like if you're selling the shovels like OpenAI and Google with Gemini, you can make money.

Starting point is 01:19:53 And if you own the mine like Rippling with the data, you can make money. If you're somewhere in the middle building AI software that then tries to use the shovels from the shovel provider, but then also needs to rent out the mine or get the ore out of somebody else's mine. start refining it. Like you are in, you're in a very difficult place from an economic standpoint, because you're not going to be permitted by either of those parties to build a big business on their backs. That's just not how it's going to work. They're going to demand value capture that crushes your unit economics. So I look at the 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

Starting point is 01:20:42 at viable unit economics to be an interesting business. And that is going to kill off 80 or 90% of the stuff that I see right now as standalone AI businesses. So what I'm hearing here, I love that you correct me when I get these things wrong. And this is 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? Yeah. Because, look, SaaS software is a bit flipping.

Starting point is 01:21:13 All SaaS software applications are bit flippers. Like it's an in your face. Yeah, changing values into data bits what it does. It's a really hard product. Like Rippling, one of Rippling's superpowers is where a coin sorter, you dump like $20,000 for an employee in the top of the coin sorter, and it figures out what goes to the government, what goes to health insurance, what goes to your 401K,

Starting point is 01:21:31 what goes to you. And it has to move all that money very, very reliably and seamlessly, very challenging software to build and manage. What's it doing? Even that is just flipping bits in a database. And so AI is a new way to flip bits. AI is just a new way to flip bits. Hopefully a way that abstracts us a little bit further from having to think.

Starting point is 01:21:53 Because our future is Wally. It's going to be great. Speaking of Wally, actually, I have this Matic robot. Do you have one of these? It's like a human, it's like a self-driving car robot, basically. Self-driving car people build this robot that cleans your, your house. 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 expensive, but incredibly cool. And actually in Wally, if there's a scene where they actually have what basically what these things look like. So it's not so far.

Starting point is 01:22:25 I had that movie 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 the say, stuff, which I'm hearing is you're probably, we're going to see a lot more consolidation where these point solution companies realize they need this data. This is existential and they're going to combine and merge and bundle, as you described. It's possible. I am not a problem or a investigator on this stuff. I think like there's some really interesting investors out there who I think are thinking quite deeply about this and in particular, like the conviction, which is like Mike Fernal and Sarah Goua, I think those are two investors who are hyper-focused

Starting point is 01:23:07 on AI. And when they made the decision to sort of take that approach, at the time I thought, like, as that's kind of narrow, now I'm like, no, no, no, that was the right move. And, and like, it just means that they, like, they have a very deep, deep, deep, a set of hypotheses that they've formed over the course 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 Elah have a podcast called No Priors that I'd also recommend.

Starting point is 01:23:40 we'll point you in the show notes. So on the AI note, I guess is there anything else that you think would be really helpful for founders that are working in this space building an AI startup to hear. They think you're seeing of like, here's how you need to. Here's what you need to do to win in an AI company. Oh.

Starting point is 01:23:57 So much. Like, I actually think that if I were to give you an answer to this question right now, it would be bullshit. Yeah. I don't have, like, 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. 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 going to take

Starting point is 01:24:25 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've found it unlocked in high? I mean, it's not a super exciting thing. thing, but I'll say like where I use, so 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, chat GPT and Gemini, where 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 want to communicate. Help me come up with pithy ways to articulate these things. And 80% of what it outputs is trash. It's just like sort of middle of the road, average low alpha junk. But it is a thought partner, a non-judgmental

Starting point is 01:25:29 thought partner where like 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 kind of hit the nail on the head for this concept. And so if you, if I believe that my job is to sort of bring brains along on the journey for some sort of change that I'm trying to bring about, then the most important tool is language. And I do find that that chat GPT and Gemini do a great job of helping me refine how to articulate the concepts that I want to articulate. They are not useful in coming up with the ideas themselves. 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,

Starting point is 01:26:07 used it, but by virtue of this conversation, I'll probably go give it. There we go. Yeah, they're all great, but there's something about Claude that is just at writing specifically is much better. But they're all getting better all the time. There's always, there's always something new. Matt, we've covered so much ground. We've touched on everything I was hoping to touch on.

Starting point is 01:26:27 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 spent a lot of time talking about intensity. and the grind and the need to just always be operating at the 99th percentile. And I think if you listen to that in a vacuum, it's very easy to believe that that intensity is soul-crushing, that it's a negative, that it's maybe not something that you want. And I think there's a backstop for me that I didn't talk about today that I think is important to share, which is that life is amazing. That 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.

Starting point is 01:27:34 that like if you remember how insignificant we are and all of this is, it brings this levity to what we do and to the work we put into building this because this is like Silicon Valley in 2025 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've got to zoom out and appreciate that magic. And so then you turn around, you're like, fuck, I got to work on Friday night, right?

Starting point is 01:28:17 Like, I've got to go give it my all. I've got to go compete in the arena of business. Just you have to 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 talked about. That is beautiful. I think about pale blue dot Carl Sagan's whole thing. Just a stunning photograph that literally changed the way I think about

Starting point is 01:28:58 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. I'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. I said 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, links to

Starting point is 01:29:33 in 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 the 20s and 30s who are just sort of getting the hang of being a CEO or a product leader for the first time. This book is absolute fucking gold. It was recommended to me by Brian Shrier at Sequoia when he was on my board at my previous company. I took way too long to take him up on the advice. Wished I had read it sooner. Highly recommend conscious business changes your life. Number two, thinking in systems, Donna Meadows, I always mispronance her name, Donella Meadows. She died partway through writing this manuscript. Her fellow professors

Starting point is 01:30:11 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 1960s, the effective executive. It's an anachronism. It uses weird pronouns for the secretary and the executive. I'll let you guess which ones. But like the book itself is so chalkful of simple, enduring advice on how to be effective at leading teams. And the good shit is the stuff that's been in print for 70 years. And that's that's one of them.

Starting point is 01:30:47 Beautiful. I love the first one is you don't have it because you're using it with your team. You mentioned at one point before we started recording, you have like eight copies of that book that you just give out to everyone. Yeah. Yeah. and we hand it out like candy. Okay. Is there a favorite reason to movie or TV show?

Starting point is 01:31:01 You've really enjoyed. Yeah, so I'm a little embarrassed by this answer, but I'm going to be honest. Please. There's a new series called Heeded 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 world is watching.

Starting point is 01:31:27 but actually they're secretly in love with each other and they start hooking up and it's been labeled by the media as smutty but delightful and I would say that's accurate. So it might not be for everybody, but it is a 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 a little chinty, 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. And soon to be on Netflix with the acquisition if that goes through. Oh, yeah.

Starting point is 01:32:00 That's crazy. Amazing. Okay. Is there a favorite product you recently discover 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.

Starting point is 01:32:14 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 actually have one in the office and one at home. and one in the garage. Wow. That is a favorite product.

Starting point is 01:32:31 You have three of them in the same place. Oh, no, in the office. Fellow is also a rippling customer, and that's like 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.

Starting point is 01:32:45 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 actually sometimes useful. Immediately at least it's sort of a moment of smiling when it happens.

Starting point is 01:33:01 It's like 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 were going through some shit yesterday at work and we were like, fuck, now that happened. And I looked at the CTO and I'm like, dude, nothing's ever so bad that it couldn't get worse. And we had a good laugh and continued to brace for whatever might come next. So not exactly uplifting, but fun to use. No, that is, it is uplifting.

Starting point is 01:33:28 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 very useful. And it might get there. So let's ensure it's less worse version. Final question. Something you shared with me is that you were a DJ when you're a younger person.

Starting point is 01:33:47 Can you just give us a little DJ voice to give people a sense of your other skills? First of all, it's not DJ, Lenny. It's radio personality. And yeah, I used to do the greatest hits of all time with his from the 60s, the 70s, the 80s, and a little bit of the 90s. 1015, the Hawk. Yeah, you can turn it on. It's very inauthentic, but it sounds good on the radio. It's cool.

Starting point is 01:34:10 I did it when I was in high school. I ended up doing the midday segment right before I went to college. And what a gift. What a huge gift in my most formative years to have developed, 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'd like lean really close to the mic to get that, to get that radio personality voice.

Starting point is 01:34:34 Yeah, you got to be able to hear like the saliva in the mouth. Incredible. 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.

Starting point is 01:34:45 I really appreciate being here. I really appreciate sharing all this advice that I have not heard other people share. Two final questions. What do you, is there something you want to plug, point people to, and how can listeners be useful to you? Look, my life is replaying. I appoint people there. And this is my life's work. It's going to be a banger. So stay tuned. And the way that you can help me is that if you're a customer, you got to tell me when you have problems because that's how we get better. What's the way they get to you? Is there any place you want to appoint people to?

Starting point is 01:35:12 DM me on Twitter is easy at stay nine. You can email me my last name at rippling.com. And I'll go that far without giving out my phone number. How's that? The perfect boundary. 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 got to get me some of that stock and that got to get into that rippling.

Starting point is 01:35:40 It's a good buy. It's a good. But you're, you know, hard to go. Hard to come back. All right, man. Thank you so much. Thanks. Thank you so much for listening.

Starting point is 01:35:53 If you found this valuable, you can subscribe to the show on Apple. podcast, 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 lenniespodcast.com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

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