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

25:27Now that you're on the inside of the product team, what's something that you think people outside of product, say Matt two years ago or other, I don't know, go to market leads, other execs should hear, need to understand about product that they don't until they're on the inside? I'll give you another framework that I like to use. In the financial world, there's this concept of alpha. Alpha is outperformance relative to the index. So that's why you have seekingalpha.com as a very popular website. What they mean by that is you're looking to buy something, some combination of assets that will outperform, let's say, the S &P 500, if that's your benchmark.

26:09So alpha is the outperformance relative to the index. And then you have the concept of beta. Beta is just volatility. Beta is not good. A high beta stock jerks around for no particular reason. It's like discorrelated with the index. It's very high beta. great if you're an options trader, but other than that, it's not really something you want in an asset. And so your ideal stock is a very high alpha, very low beta stock. They don't really come in that shape because alpha and beta tend to be correlated, but that's what you want when you buy a financial asset. So what's the analogy? I think you have high alpha people who are very valuable.

26:47And 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 so when you're building a product from zero to one you're probably proceed pursuing alpha you're looking for some angle on this market or this customer problem where the product is actually going to provide an outsized return relative to whatever the default solution is when you have a more mature product or if you have somebody in the product operations group or whatever, you probably want a more low beta environment where it's like it cranks it out, it does it very reliably.

27:44Our payroll product, we badly want the payroll product to be very low beta. We really don't want the payroll product to have any unpredictability or aberration. And so we're willing to accept more process. And here's a fundamental principle of design in an organization, which is that processes, processes in a business exist for the sole purpose of lowering beta. Processes are for decreasing volatility in the output of the system. The downside of a process is that it suppresses alpha. And you have to be super, super careful and judicious in the application of process 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.

28:34And so as we've gone through the last year of reforming the way that we build product at Rippling, it's been a game of recognizing those places where I need to implement a touch of process, just a touch. Other places where I need to implement a very clear, rigid process where I don't want alpha, I just want low beta. And so examples of this are, let's say, our product quality list, which we lovingly at Rippling call the pickle. Why pickle? Yeah, so it's actually a really important thing. I think if you want to bring about cultural change in a team, like, look, we have 1 ,300 people in our R &D organization.

29:08It's a big ship that we have to steer. If you want to create a moment that sticks in people's brains and sort of becomes a zeitgeist or something that they latch onto, you got to create an entity, a vessel for meaning, and then you got to fill that vessel with your meaning. A meme, you might say. Yeah, well, sure. A meme is actually a good example of this in common culture. I, in pop culture, I think it's why when people come to the table with ideas from the outside, I welcome those outside ideas. But the first thing I ask the person to do is to tell me what they mean without using those words.

29:43So 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, OK, you actually haven't thought this through. And so with the pickle, with the product quality list, it's like I could come up with some generic term for this. But I really want a new joiner at the company to understand that this is an idiosyncratic thing to Rippling.

30:11This 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. 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.

30:50And 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. If you're not aware, Parker is the sole payroll administrator for rippling for all 5 ,200 employees. He personally runs payroll always. There is no exception for all 5 ,200 people. He does complain about it sometimes, but it's a remarkable achievement for the software and perhaps for him. And so he also installs any new app that we're going to install for ourselves because we dog food the hell out of everything we build.

31:22Yesterday, he goes to install this new application. We're about to ship a new app for feedback, allowing people to give one another's feedback in their companies and he installs it and he goes in and it dumps him onto an empty screen and he's like what the fuck is this what is this what's going on like hey wow talk about fail so i um chop another one of my fingers off i'm down to nine and uh i'm like what did we miss what we missed was there was a fucking feature flag fucking feature flag i'm just i'm not allowed to say feature flag without fucking in front of it because like feature flags are the bane of my existence and the worst things in the world that constantly cause problems engineers put one in temporarily and forget it's like shims if you're building a house and the general contractor puts little shims in places and then forgets that they put the shims there and then builds a wall over them and eventually the shim fails and all of a sudden your door doesn't fit like feature flags are super dangerous and need to be managed carefully so fucking feature flags anyway we had one parker installs it they forgot to disable the feature flag he gets a blank screen when he installs the application.

32:26What did I do? My reaction was, ugh, go back to the team, give them direct feedback, tell them not to make that mistake again, but also ask the question, how do we miss this in the factory inspection process? And the answer is, we didn't have any line item in the pickle for feature flags. And so I added a line to the fucking pickle that said, you are allowed to have one feature flag that governs your entire product at ship. It's an extreme standard that might not be achievable, but it's the standard we aspire to. This framework, the pickle, given these lightweight checklists, iterated on consistently in response to everything we learn as we go, constitutes a very nice lightweight way to lower the beta of the system with hopefully only a modicum of negative impact on the alpha for how we build product.

33:21And 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 2000 technical workers. Wow. Okay. By the way, PICL, is that, is that like an acronym or it's just like, I like this word we're going to call it PICL? Product quality list. Product. Okay. I see. So it's the consonant. Okay. P-Q-L, which how could you pronounce it other than PICL? I'm imagining all your decks have little pickle emojis. The pickle emoji thing, the dancing pickle in Slack. There's a lot of, yeah, it lends itself to a bit of fun.

33:58What I think about is Pickle Rick. Do you get that reference? This is a Rojac 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 we're okay with a lot of variance for this specific project. Yeah, we're willing to accept a bunch of volatility in this area in exchange for the upside we get from the creativity and risk-taking of these people or 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 low beta or not?

34:29For 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, And I think I've spent a lot of time with teams at Rippling talking about how I hire. And it is born of batting practice. It would 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 on my intuition, which of course HR people say you're not supposed to do.

35:12That's complete bullshit. If you have a good intuition, you should absolutely rely on your intuition. And what you have to do after you have a reaction to a candidate when you're looking at hiring somebody is you need to decode your intuition so that it can be expressed to other people productively. And so one of the frameworks that I use for this is SPOTAC. It's a very ugly acronym. There's a hat tip to somebody out there in the universe who originally thought of this. It's not me, but I adopted it. And it's that people are smart, passionate, optimistic, tenacious, adaptable, and kind. Those five things.

35:48Six, can't even count. I told you I lost a finger, right, when I made a mistake. So I was down one. Nine to go. Spotac isn't by itself a good top-down framework, but when you're thinking about, oh, why did this candidate just like, why did it not click? Why did 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. 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 it's the the framework is super useful to evaluating people and i think the the alpha beta framework is also super useful when you come away from a conversation you're like i like that guy i think he'd be really really good why is it that i don't think he would do a good job on this product in particular and the answer is like this is a high alpha product area and he's a low beta person valuable but definitely not the right fit for this and so i think it's really useful in that context as well i love all these frameworks you're speaking to this audience frameworks frameworks frameworks yeah so high high alpha low beta sometimes high beta is okay spotac um in hiring is there anything else that you find really useful before we move on to a different topic when i first started working in the product organization i was introduced to a an interview framework or an interview tactic that i hadn't really used much at all i think in my career, which is that every product person at every seniority level is given the same case study.

37:26And the case study is extraordinarily difficult. It requires you to think about many, many dimensions simultaneously to think about data propagation issues. It's 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.

38:08There was 10 they didn't see around, but they saw around four of the hardest ones. And they were not defensive when we gave them new information that called in the question, the validity of their solution. And they were willing to interrupt us to ask more questions and, and, and like a lot of the sort of basic human interaction models. I, 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 kvetchis a bit about this and feels like we eliminate people too aggressively at this stage of the interview process.

38:41But I've found the wisdom in it and think it's actually quite useful to give everyone the same simple, complicated prompt and just see, hand them a drill bit, give them the concrete wall and see if they can get a millimeter or an inch into the concrete. 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, I think there's a bunch of joys, actually, if I could give you a sort of running list.

39:11But 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 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 be talking about the mini CEO. I think it's kind of a stupid misnomer, but there's some wisdom there. And I think the wisdom is that you have to be a polymath. Like you've got to be really good at working with other people. You've got to be good at communications and articulation.

39:46You'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. I'll say one other thing about what I love about leading product, which is as a COO, my job was to accept the product as it was and optimize everything around that. My job was to make sure that the product operations, in our business, the interface to the insurance carriers, the interface to the payment entities, the government regulators, that stuff all just sort of worked.

40:26It was to make sure that our sales engine, our marketing engine, all the go-to-market at stuff, like 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 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.

41:04Everything else gets easier. Finance is easier. Sales is easier. Marketing is easier. Recruiting is easier. Everything gets fucking easier. And so I think the other joy of leading the product function is that I get to set the highest order bit in the business's success to one. This is really great to hear. A lot of times people outside product don't understand these sorts of things. and look down on product a lot of times, especially 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 is and just how awesome PMs are.

41:44As you know, a lot of people are very anti-product manager. Why do we need product managers? We don't need them. Just let everything down, all this process. I have a distinction there, which is I'm anti-shitty product manager. 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. And I've learned a lot about wine. And one of my favorite wines is, I don't like Chardonnay. And I'm like, no, no, no, no, no. Chardonnays are the most fucking amazing varieties of wine in the world. You just haven't had good Chardonnay.

42:14And there's a Chardonnay out there for you. Product management. It's like, you don't like product management. You think product managers suck. It's like, well, you just haven't had a good Chardonnay yet. Once you have one, you can't unlearn it. you know like let's find that pm asap no let's find that chardonnay but let you have with some chardonnay you met you touched on this product market fit point and i want to double down on this thread you had a you've had a couple really interesting experiences of struggling to find product market fit with your own startup you said you worked on it for nine years you said okay and then with rippling uh 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.

42:59There's a line that this venture capitalist whose name I will not mention said, which was that product market fit is a sort of thing where you absolutely know it when you see it. And therefore, if you don't absolutely know it, you don't have it. And this kind of gets back to my point about learning from mistakes versus successes. It's like, ah, man, over and over again, over the course of the many years that I spent at Rippling, sorry, Inkling. We thought we had it. We thought we had product market fit, maybe, maybe, you know, and in hindsight, with the benefit of now having experienced solid product market fit, it was so, so obvious that we didn't.

43:45And like, I've invested in like 60 companies or 70 companies. I don't know. it's not something I actively do. Um, but, but opportunities by virtue, I think of my, my role at Rippling sort of show up and I talk to lots of entrepreneurs and I love it and I find it super stimulating and I love the fresh ideas. And it's just something I do as a real cherry on top of the sport that I play already. Um, but when I get the investor updates for the guys who've been it for like three four you know years and i read the updates from them that i sent to my investors in 2011 and 2012 i'm kind of heartbroken we talk in silicon valley about never quit but that is complete absolute venture capital the incentive of venture capitalist is to put money into your company and milk you dry.

44:45They 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. 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, I'm 45 years old. We're going to be on the planet.

45:25I mean, the average age of a man in the United States when he dies is something in the mid-70s. I got 20, 30, maybe if I'm lucky, 40 years left on the planet, very conscious of the time that I have. And like, I don't regret what I did at Inkling. I learned a lot. It informed what I do now. I don't think the chapter I'm in right now could have come without the chapters before it. And so it's a, it's a beautiful, wonderful thing that I did what I did. But when I read the investor update and I'm like, you're where I was and you are not getting out of this. the silicon valley try until you die mindset is not pro-entrepreneur it's pro-venture capitalist and i know why that is but i think it's important to say out loud that you should fucking quit you should reset the clock you should reset the cap table because trust me product market fit when it arrives is insane and it's exciting and you should pursue it and never delude yourself into believing you have it when you don't.

46:24It is dangerous and regrettable. How's that for a speech? Beautiful. The anti-VC speech. I got more where that came from. By the way, it's not anti-VC. It's anti-VC propaganda. 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 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.

47:12Trust me, the 45-year-old entrepreneur or the 50-year-old venture capitalist who have been in the game for a while, they get it. They've observed it. They know what it's like. The system is there to take advantage of the people who don't. Or at least it is the easiest prey for the incentive structures. Not for venture capitalists as individual people who are beautiful and wonder all of them are just 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, VCs, I'm always just like, hey, let me know when you're starting your next thing.

47:42I'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? That's the thing, like as a founder, when it's time to throw in the towel on your business and you're so obsessed with giving money back to the cap table, I always remind the entrepreneur like, hey, if you're in the seed investing game, your forecast is zero. Your assumption on every investment is that it's going to go to zero. Any seed investor who doesn't take that stance is off their rocker anyway. You know, they're a very bad investor.

48:16Seek 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-end giving easy. GoFundMe Giving Funds is the DAF, or donor advised fund, supported by the world's number one giving platform, and trusted by over 200 million people. It's basically your own mini foundation without the lawyers or admin costs.

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49:26That's gofundme.com slash Lenny to get started. This begs the question of just when is it time to quit? You know, 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. 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.

50:06And so I think like timing is a lot and it's very hard to control for. But when you get the timing right, and the market is real and the product works, product market fit, like I said earlier, it's super clear. And so if I were to pick a number out of a hat just from my lived experience, I think it's very important. One aside, don't ask people for advice. Ask people for relevant experience. If you ask them for advice, they will always give it. But if you ask them for relevant experience, they rarely have any to offer. And if they don't have any to offer, then don't ask for their advice. So ask people for relevant experience.

50:42And I try to do this with my own entrepreneurs when I work with them. It's like, let me offer you whatever relevant experience I have. And my relevant experience on this topic of when to quit is like, I think we could have called it after the second or third pivot, which was somewhere around year four. It is, of course, very important to believe in what you're building and to be persistent. consistent. 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, rip roaring growth story, it's extraordinarily difficult.

51:27This is so extremely rare. So beyond even already the rare scores you're going to face from the outset that now is going to convert to something crazy. So that's hard to hear, I guess. But man, it can be really liberating when you're like, fuck it, I'm going to do this. I have the energy. I'm going to do it again. I'm just going to do it with a clean sheet. That is really helpful. You have this really fun way of describing product market fit around receptors and drugs. Oh, yeah. Yeah. I think this is like a really fundamentally misunderstood dynamic. um when i when founders message me and they're like hey like like my linkedin posts and my tweet for this launch i do it i retweeted i like it whatever nobody follows me on twitter anyways doesn't matter but like i you know i do that and then um but i think to myself like this is not what this is about like this is not this is not how great companies are built it can be a nucleating a nucleating event, but it's not a major thing because nobody cares about your company.

52:27Like your launch doesn't matter. Big fat pull the slingshot back launches amount to the teeniest thimble of water in the ocean of noise about startups and companies. And so you just got to build it brick by brick, bottom up, and these launches don't really amount to much. And so how do you think about that? Like, how do you think about the insignificance of your launch? You think about all the effort you're putting into building a product that you believe is going to have product market fit. Well, if you recognize that the market is immutable, no amount of tweeting, LinkedIn posting, advertising is going to change whether the market wants your product.

53:08It's not, it might raise awareness about your product, but it's not going to change whether somebody wants it. Then you take a different mindset. You have to view your startup as running an experiment in the universe to see what you get in return for that. And this analogy of like drug discovery and binding receptors is like nobody at Genentech thinks they can market their way to better performance inside your body. The binding receptors for that drug, they exist or they don't. And when they build their product, their goal is to find out whether the binding receptors exist. But fate already has decided the outcome.

53:45This is absolutely true of every software product you build. Fate has already decided the outcome. The market's either going to latch onto your product and run with it or it's not. Do not ship the product, find a lack of success, and then try to market your way through that because the binding receptors likely don't exist. For me, it was a very liberating mindset because now I just have to find the right drug and I can forget trying to convince the body to develop the binding receptors for whatever it is that I'm building. What I love about your advice here is you were an early investor in Notion, which is one of the classic stories of it took them, I think it was four years to get to something.

54:20They moved to Japan. They worked on the whole thing. And so is there a lesson from there? Like, is that a rare example where it actually worked? And that's not an example to be inspired by because it's extremely, 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. Does it have this kind of founder? Does it have, you know, is it a C corp in Delaware? where boom, boom, boom, boom, boom, boom, boom.

54:51And these checklists are all about what? They're all about suppressing beta. They're about avoiding avoidable mistakes. They're about bringing stability. Jeff Lewis is an investor who has many angular views on things. And I think one of his most enduring phrases is narrative violations. This idea that the common wisdom must be violated in some way by every company that has an outsized success. It is absolutely true. And when I give these general observations on the patterns in Silicon Valley, the most successful businesses inevitably violate something on that list in some really important way.

55:36And so Notion, you can't replicate Notion's success as an entrepreneur. You can't replicate it because you're not Ivan. You can't replicate it because you're not Notion. You can't replicate it because it's not 2010 when they started the company. Do the math on that. Or 2011, actually. These guys stuck with it. They went through hell. They pivoted. They went to Japan and sat in kimonos and meditated on what they were going to build. And by hook 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.

56:20It is dominated by Google and Microsoft. Carving out your own niche in that market is just unthinkable. And so I look at Notion as having succeeded by virtue of the narrative violation of persistence. I don't think it's a good idea for very many people. 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.

57:11The idiosyncrasies of the founder. Rippling succeeds for almost the polar opposite reasons that Notion succeeds. But in both cases, the companies succeed on the idiosyncrasies of the founder. And so embracing that, recognizing those idiosyncrasies, that's what great investors do. They spot that element of spikiness and greatness in a candidate investment, and they convert that to a commitment. And then, of course, the investor or the good ones accept what they get in exchange from that for the universe, from the universe. I love that we went in this direction. I wasn't planning to talk about your investing career.

57:47Just to give people a reason to listen to this and maybe rewind, and I want to ask another question around investing. What are some other companies you invested in early? First of all, okay, so I sort of hate the question. Like, what are some other companies you've invested in? That's a fair question, but the problem is 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, I'm going to give you here, let me, let me give you some, some, like some bait. Like I was one of the first investors in notion.

58:16I was perhaps the first, I don't know, ask Ivan clever, which had a great exit. I was one of the first investors in Zenefits. If you've heard of it, I was before I joined one of the first investors in Rippling and then more recently like invested in, here's a funny one. I was one of the first investors in deal, if you've heard of them. I was able to exit, 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, like, you know, if you know, like Decagon, which is doing some really cool stuff on the AI front.

58:58Killing it. I mean, Langchain, like great so those are some companies that you maybe you've heard of but like how about like i invested in macro the founder was derrick lee macros out of business i invested in debrief ned roxson it's it's out of business you know i invested in verb data with david hertz out of business i'm reading from a list i invested in um what's the number 70 companies according to this list where i track things and like most of them went to zero and all those founders were awesome All those founders were kick ass. And all those founders put a shit ton of energy into building their businesses.

59:33And 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 have, and I've, you know, I've got a few subsequent. And actually, a lot of them joined Rippling, believe it or not. So, I don't know. Companies I've invested in is a long list. And I love to give you names of companies that don't exist anymore because it's self-serving and a horrible survivorship bias to just list the good ones. I love that answer. I think you're being modest in the context of your hit rate is clearly very high.

1:00:07Even 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 at-bats they've had. It's good practice to ask people to give you the full list. What are your favorite failures that you've invested in? Oh, no, I'm not actually, okay. Well, obviously, like, you know, we don't spend time on it, but I think it's actually a good question. Yeah, like, what are some of your, what are your best failed investments?

1:00:37Show me the logos of the companies that didn't work out. 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.

1:01:19And so like power law distributions happen everywhere. It explains why so few people control so much wealth. It explains why Steph Curry is just so vastly better than the next guy down on the list on the basketball team. It explains why populations are concentrated into a really relatively small number of mega cities in the world. It's like power law distribution just plays out everywhere. And like once you see it, you can't unsee it. It 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 Y equals X.

1:01:54But that is absolutely 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%, the top 5%, don't just get 10 % or 20 % more reward. They get 10x the reward or 100x the reward. It's really dramatic. Entropy, the second law of thermodynamics, is a very simple concept. It's the reason your sock drawer becomes messy. It's the reason that potholes form. It's the reason we have to put so much energy into maintaining the aircraft we fly to keep them safe because they really, really, really want to fall apart.

1:02:37And that's the nature of things. If you abandon a city for a few months, it starts to go fallow. And so entropy is just this concept that shit tends toward disorder. 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 we fight entropy until we lose the battle somewhere, as I said earlier, at the age of 70 or 80, if we're lucky. What does this have to do with product? This is really about effort. The only antidote to entropy, the only antidote to decay in a system is energy.

1:03:24You 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. 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.

1:04:08over company outcomes. Not because they get together and think we should do that, although unions do do that unequivocally, deliberately. But even in a collection of product managers or engineers, what's going to happen over time is entropy is going to creep in and people are going to optimize for local comfort. Your job as an executive, as a leader, is to fight that entropy tooth and nail every single day. It means that every time you see a bug, every time you see a bug, not most of the time, every time you go and you drop it at the feet of the product manager or the engineering manager, every time in public, preferably.

1:04:51It 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 bored and tired zone on any process that you as the executive have got to demand the 99th percentile of energy because otherwise entropy creeps in and the system decays. You have to do this. One of the messages that I delivered recently at our big executive big, like our top 75 manager off-site that we do roughly every 18 months, was a reminder that if the purest form of ambition and the purest and most intense source of energy in the business is the founder CEO, that every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity.

1:05:52And that is fucking dangerous because if you go to two layers and it's two orders of magnitude drop off and signal an intensity, that is a very dysfunctional organization. So what I said to the team was, it's not that you need to buffer people from the intensity of the CEO. It's that you need to absolutely mirror that intensity. There are plenty of constituents in the business around you who will advocate for relaxing. There is an infinite supply of people under you who will buffer other team members from the intensity of the demands. Your job is not to be one of those buffers. Your job is to preserve that intensity at its highest possible level and let the buffering happen somewhere else.

1:06:39And that's the point is that entropy creeps into the system insidiously and slowly over time off your radar. And you have to maintain that intensity every minute of every day to try and fight it. If you want to stay at the extreme right end of the power law that obviously governs the outcome of everything that we build. what does that look like to pass along that intensity like what does that feel like what does that look like so say parker comes to you this bug sucks i got this broken screen you cut 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 um actually the joke that i sort of played on this one when i presented to the to the team was that the next sort of slide in my presentation was with the sound effect, the Slack huddle thing.

1:07:36And 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 presentation was boop, boop, boop, boop, boop, boop, boop, which is the sound that Slack makes when someone calls you. And it was Parker Conrad is inviting you to a huddle. And then the next slide was Parker Conrad is modeling personal intensity. And the idea is if you know, you know, like 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.

1:08:13That intensity is one place where it plays out. Every product team at Rippling, and we have a lot them now have public feedback channels. I am in there upside down on everything I find when I use those products. And I just model for everybody that this is how at least I want to do it, which is, I don't like this. I don't understand this. Tell me why this is this way. Boom, boom, boom, boom, boom. And people jump in and respond. The factory inspection process that I mentioned, which is where at the end of the assembly line, I jump out with the pickle and we talk about all of the elements. You have to record a loom of every major flow through the product.

1:08:47I personally review every one of those flows. I got a backlog I got to catch up on today and provide feedback to people always in a public channel so that every other product manager and engineering manager can jump in and see how the process has worked for other teams. It's about modeling the intensity publicly so that other people can say, okay, this is how we do things around here. And it gives the reaction from the team that received the message that you have to inject that energy every minute of every day and that there are no exceptions was not like, ooh, that's exhausting. The reaction is, oh, that is so invigorating.

1:09:25It's like so wonderful to hear that we're going to achieve these great outcomes, or at least we have a shot at doing so, and that you're empowering me to follow my instinct, which is to really like push for the best result. The reaction universally is like, what a relief that I get to go be intense because nobody in a position of leadership wants to be chill. And like, what's worse than a chill boss? No, don't work for a chill boss. Don't be a chill boss. It's the most pejorative label I could give you. Chill boss or chill PM. Don't be chill. Chill doesn't accomplish shit. Be intense. Be good.

1:10:05Be respectful. Be intense. Don't be chill. And again, this advice comes from where we started, which is this is what success looks like because somebody that is less chill than you is going to find that crack and come after your market. Is that the gist? For sure. I mean, again, if you're chill and you move the X axis down 10 or 20 points, the Y axis collapses. It doesn't just drop 10 or 20%. The Y axis collapses. And this is just kind of true in everything we 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.

1:10:50I'm going to make recurring income. It's going to be amazing. And I, in my experience, anytime there's a market or something shows up, that's juicy and there's ways to make money. Somebody is 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.

1:11:25Sell your time. It's not gonna be super competitive, but like sell that, you achieve that level of leverage. And there's just going to, there's, it's a pretty efficient market. To close out this, uh, thread of intensity and adding energy to everything. Something I've heard about you is you're big on, uh, 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. Well, I mean, fundamentally the most selfish thing you can do is withhold feedback from someone. Who are you optimizing for when you do that?

1:11:54What are you optimizing for when you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable? Well, you're optimizing for your own comfort and it's fundamentally selfish. It's the most selfish thing you could possibly do is withhold feedback that would otherwise be useful to someone because you don't want to be uncomfortable. Well, that's not how high performance teams operate. So I demand feedback and I give it. And it doesn't mean that when I give feedback, it's not open to being questioned or discussed. I mean, of course it is.

1:12:29But 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, the customers withhold. Customers don't want to escalate to me as an executive. Even like the founders in whose businesses I've invested who use Rippling are reluctant to hit me up when something goes wrong because they don't want to bother me. But it's literally my job, literally my job to find things, problems, and make them better. And by virtue of making those specific things better, to iterate on the processes so that the system that builds the system can get better.

1:13:09There's no greater gift to me as a product executive than receiving an escalation from a customer. We have an escalations team at Rippling, which sounds weird, but it's people who are just particularly skilled at pistol whipping other people in the company to get to real root causes, real root causes, not like throw away the word root cause, like, we fixed the data error and shut the ticket down. No, you went and you found the software that created the data error, and then you found the system that created the software that created the data error, and you solved all that back to the top. Escalation seems extremely good at that, at Rippling.

1:13:47So we have sort of a dedicated little team that does this for us. Escalations are a gift. And I'd 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, So the fact that I might already know it is not a reason for you to withhold the gift of your feedback. So it's an attitude that I take to this every day. I've got a little cue of some stuff that I've, you know, minor things that are from the last couple of days from people who had some nits and issues that I'm just like, I've got them cued up on my to do list today.

1:14:15And I'm going to take them to the product teams directly. Like, I'd like to understand what happened here. Not in a negative way. I just think we'll all get better if we study this one. And so, yeah, escalations are a gift. Feedback like that is a gift and nobody is ever inconveniencing me when they do it. 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.

1:14:46What are some things you can share that are public or not public that give people a sense of just how massive this business has become? People look at Rippling from the outside. I think they think of us as like payroll and HR or whatever, which is cool. Like it's 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.

1:15:17And like when you translate that from where we are today to where we think we're taking things. It's like, we really do believe that like the core of every workflow and everything that a company has to do, be it AI or manual, traditional GUI based software is like, is who's doing stuff, who owns it, who's accountable. And so the people record is a really important component of that. You can argue that the customer record is also very important. And of course, some big 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.

1:15:49Everybody agrees on that. Workday agrees on that. Good luck to them. But they have failed, actually, despite their success, to build a really broad general purpose software platform for business software on the foundation of the people primitive. So we're going to do that. And we're successful because we deliver on that promise at the scale we're at today. The fact that you can do, and this is not a sales pitch or sort of like an advertisement for Rippling. I just think it's important to sort of contemplate that when you bring together a bunch of disparate business processes into one system on a common business data graph, an object graph, a data lake with a consistent interface, you can do some pretty magical things.

1:16:27So we do payroll, we do HCM, we do IT, we do spend, we are about to launch a new product in the category of business intelligence and data management. And there's a whole bunch of other stuff coming beyond that. And then you layer in AI on top of this, where we alone, where we alone have all of your business data organized into this nice, neat package with a beautiful semantic layer on top of it, the AI can work magic. And we have shipped nothing, nothing yet in this category that I would say gets anywhere near what we're going to show next year. And it is going to set the standard. It is going to be the most, 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.

1:17:16So I'm super excited about the tailwind this is going to create for us. You ask about what can I share about the success of the company, what I can say. There are tens of thousands of companies that now run on Rippling. We're less than 1 % of the market. And the market cap at$16 billion, I think now undervalues where we are from a revenue perspective by a long shot. There is just so much upside to do what we're doing. SaaS might be dead-ish in terms of point solutions, but long live SaaS in terms of what we're building. Let me follow that thread. And in AI, there's been a lot of talk about AI is going to replace SaaS, as you maybe just said.

1:17:55People are going to vibe code their way to their payroll system, which I 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 do a lot of things for people, for them to continue to pay for your software. Is that the gist? No, 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.

1:18:29And you just got to get the timing right. So this is a period of bundling. Point solutions don't have enough data in the age of AI to be useful. You've got to be able to provide the AI with a lot of context about a lot of data so it can do things. It can do joins. It can do correlations. And so if you're a point solution, you're in hard water because you've got to now rely on data from other sources. You've got to integrate to third-party systems. And when you integrate to a third-party system, even the best ones are still sort of drinking their data through a straw, which is a real problem. I mean, 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.

1:19:20Like, what are they going to do? What are they going to do? This is never going to work. It's just no way. And so I literally have no idea what they're going to do. They're just not going to build AI software, I guess. 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 is that point solutions in the AI world are also in a rough spot for the same reason. It's like if you're selling the shovels like OpenAI and Google with Gemini, you can make money.

1:19:53And 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 and start refining it, you're in a very difficult place from an economic standpoint because you're not going to be permitted by either of those parties to build a big business on their backs. That's just not how it's going to work. They're going to demand value capture that crushes your unit economics. So I look at the landscape of AI companies that I've seen, and I think you have to have a really durable, interesting insight that gives you a shot at viable unit economics to be an interesting business.

1:20:45And 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 that's exactly what I want. what I'm hearing is it's less about how difficult it is to build the SaaS product. It's about do you have first-party data that allows you to build an incredible AI product on top of what you've got. Yeah, because look, SaaS software is a bit flipping. All SaaS software applications are bit flippers. Like it's an interface changing values into data. It's what it does. It's a really hard product.

1:21:20Like Rippling, one of Rippling's superpowers is we're a coin sorter. You dump like, you know,$20 ,000 for an employee in the top of the coin sorter and it figures out what goes to the government, what goes to health insurance, what goes to your 401k, what goes to you, and it has to move all that money very, very reliably and seamlessly, very challenging software to build and manage, what's it doing? Even that is just flipping bits in a database. And so AI is a new way to flip bits. AI is just a new way to flip bits. Hopefully a way that like abstracts us a little bit further from having to think because our future is WALL-E.

1:21:56It's going to be great. speaking of WALL-E actually I have this Matic robot you have one of these it's like a it's like a human it's like a self-driving car robot basically a self-driving car people build this robot that cleans your house it's maybe I didn't mention that it's like a house cleaning robot that just like goes around it's like a Roomba you should get one they're expensive but incredibly cool and actually in WALL-E there's a scene where they actually have basically what these things look like so it's not so far That movie was actually quite prescient, perhaps with the exception of the gravity-defying daybids.

1:22:32Yeah. I don't know, but that's not good news. You've seen that movie. Oh, man. So on this AI stuff, which I'm hearing is you're probably going to see a lot more consolidation where these point solution companies realize they need this data. This is existential. They're going to combine and merge and bundle, as you described. It's possible. I am not a part of an investigator on this stuff. I think like there's some really interesting investors out there who, who I think are thinking quite deeply about this. And in particular, uh, like I, the conviction, which is like Mike for now and Sarah Goa.

1:23:03Like, I think those are two investors who are hyper-focused on AI. And when they made the decision to sort of take that approach at the time, I thought like, as, um, that's kind of narrow. Uh, now I'm like, no, no, no, that was the right move. And it just means that they have a very deep, deep, deep set of hypotheses that they've formed over the course of kind of seeing every AI deal in the Valley. And there are better people to ask this question of than I am. And I think if you're an entrepreneur, I recommend them to you because I think they're really smart. Awesome. I love those guys. Also, Sarah and Ilad have a podcast called No Priors that I'd also recommend.

1:23:40We'll point to you in the show notes. so on this ai note i guess is there anything else that you think would be really helpful for founders that are working in this space building an ai startup to here they think you're seeing of like here's how you need to here's what you need to do to win in an ai company oh 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 anything back to my point earlier i don't have like I don't have enough relevant experience in the abstract to like dole out on a podcast on that topic. But I, you know, I wish them luck.

1:24:17I 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 us to AI Quarter, which is a recurring segment on this podcast. And the question is just what's one way you've found AI to be useful in your work day to day? Is there something that you found it unlocked? I mean, it's not a super exciting 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.

1:24:48So 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, um, to AI, chat GPT and Gemini where I, I take like a really, let's say, angular view of some topic. And I give, really, I write the essay for the AI. And I'm like, look, this is the crisp idea I 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 middle of the road, average, low alpha junk. But it is a thought partner, a nonjudgmental thought partner where in 20 % of the stuff it comes out with, I'm like, it's pretty good.

1:25:32That's a new word I didn't think of that does kind of hit the nail on the head for this concept. And so if I believe that my job is to sort of bring brains along on the journey for some sort of change that I'm trying to bring about, then the most important tool is language. And I do find that ChatGPT and Gemini do a great job of helping me refine how to articulate the concepts that I want to articulate. They are not useful in coming up with the ideas themselves. 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.

1:26:05I have not spent a lot of time with Claude. I have used it, but by virtue of this conversation, I'll probably go give her a shot. There we go. So 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. It's always there's always some new. Matt, we've covered so much ground. We've touched on everything I was hoping to touch on. Before we get to our very exciting lightning round, is there anything else that you were hoping to share? Anything else you wanted to touch on or leave listeners with? We've spent a lot of time talking about intensity and the grind and the need to just always be operating at the 99th percentile.

1:26:45and um i think if you listen to that in a vacuum it's very easy to believe that that intensity is soul crushing that that it's a negative um that it's maybe not something that you want and i i think there's a backstop for me that i didn't talk about today that i think i i is important to share, which is that life is amazing. That like the fact that we all exist on this blue marble, drifting through space and time, that we are some weird instantiation of consciousness, each of us, and that you're here for such a short period of time whittling your stick, doing something. That like, if you remember how insignificant we are and all of this is, It brings this levity to what we do and to the work we put into building this because this is like Silicon Valley in 2025 is Florence in the Renaissance.

1:27:56It'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 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? Like I've got to go give it my all. I got to go compete in the arena of business. Just you have to, you never, you have to never forget that number one, none of this matters. And number two, it is an absolutely beautiful and amazing phenomenon that we get to be alive doing this right now.

1:28:35So 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 stunning photograph that literally changed the way I think about who I am as a person when I saw it. Yeah. Well, going in a completely different direction with that, Matt, we reached our very exciting lightning round. All right. 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?

1:29:16Okay, two or three books. Give me a heads up on this. So like one, one book is conscious business. I don't have Conscious Business in front of me because it's actually at the office because we have Conscious Business Reading Club at Rippling. And every member of my current, my product leadership team is going through this right now. Conscious Business, Fred Kaufman, it's been used in many businesses, LinkedIn, most notably as a framework for thinking about effectively, it's a user manual for human beings. So if you are a leader, a manager, an executive, whatever, particularly younger, like people in their 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.

1:29:51It was recommended to me by Brian Schreier at Sequoia when he was on my board at my previous company. I took way too long to take him up on the advice. Wished I had read it sooner. Highly recommend Conscious Business. Changes your life. Number two, thinking and systems. Donna Meadows. I always mispronounce her name. Donella Meadows. she died partway through writing this manuscript. Her fellow professors picked it up and finished it for her. It is the best generic framework for thinking about 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.

1:30:27It's an anachronism. It uses weird pronouns for the secretary and the executive. I'll let you guess which ones. But the book itself is so chock full of simple enduring advice on how to be effective at leading teams and uh the good shit is the stuff that's been in print for 70 years and that's that's one of them beautiful i love the first one is you don't have it because you're using it with your team yeah constantly you mentioned at one point uh before we started recording you have like eight copies of that book that you just give everyone yeah and we hand it out like candy okay is there a favorite recent movie or tv show you've really enjoyed um yeah so i'm a little embarrassed by this answer but i'm gonna be honest please um there's a new series called heated rivalry and it's about i'm canadian and i'm gay so it's about two hockey players um in canada rivals between the bruins and the maple leaves 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 but actually they're secret secretly in love with each other and they start hooking up.

1:31:32And it's been labeled by the media as smutty but delightful. And I would say that's accurate. So it might not be for everybody, but it is a smash hit right now. It's on HBO Max and Crave. And it's only six episodes. But like I said, a little embarrassing because it's a little chintzy, but it's a lot of fun. It's also really fun to see gay people represented in the media as though they're normal. And soon to be on Netflix with the acquisition if that goes through. Oh yeah, that's crazy. Amazing. Okay. Is there a favorite product you recently discovered that you really love? My fellow coffee maker.

1:32:09I love my fellow coffee maker. It's got an interface that lets you like set light, medium, dark roast. It changes the temperature. It blooms the coffee. It tells you how many grams of coffee to put into the basket. Slick interface, high quality coffee. It's like, it's definitely awesome. And so I have actually have one in the office and one at home and one in the garage. wow that is a favorite product you have three of them in the same space yeah yeah oh no in the office okay fellow is also a rippling customer and that's like a a nice side effect when we get to have they ever escalated anything to you no if you're listening and you're from fellow i want to hear all your gripes perfect two more questions do you have a favorite life motto that you find yourself coming back to often in work or in life it's a dark one and i'll share this one sort of partially for the humor of it, but it's actually sometimes useful.

1:32:58At least it's sort of a moment of smiling when it happens. It's like the motto comes from my dad who said, Matt, nothing's ever so bad in life that it couldn't get worse. And it's like, we were going through some shit yesterday at work and we were like, fuck, now that happened. And I looked at the CTO and I'm like, dude, nothing's ever so bad that it couldn't get worse. And we had a good laugh and continued to brace for whatever might come next. So not exactly uplifting, but fun to use. No, it is uplifting. I'm an optimist and I find myself thinking that often with my wife. Just like, it could be worse.

1:33:32It could be worse than this. Definitely could be worse. 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 were a younger person. Can you just give us a little DJ voice to give people a sense of your other skills? it's not dj lenny it's 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 101.5 the hawk yeah you can turn it on it's very inauthentic but it sounds good on the radio uh it's cool i did it when i was in high school i ended up doing the midday uh the midday segment when uh right before I went to college and what a gift, what a huge gift in my most formative years to have developed like, uh, an ability to be in front of a microphone comfortably, you know, cause here we are.

1:34:28I love for people that weren't watching this YouTube, you like lean really close to the mic to get that, to get that, uh, radio personality voice. Yeah. You gotta 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? Uh, that was great. You nailed it, Matt. Uh, this was incredible. I really appreciate being here. I really appreciate sharing all this advice that I have not heard other people share. Two final questions. Is there something you want to plug, point people to? And how can listeners be useful to you?

1:34:55Look, my life is rippling. I point people there. And this is my life's work. It's going to be a banger. So stay tuned. And the way that you can help me is that if you're a customer, you got to tell me when you have problems. Because that's how we get better. What's the way they get to you? Is there any place you want to point people to? DM me on Twitter. is easy at stay nine you can email me my last name at rippling.com um and uh i'll go that far without giving out my phone number how's that perfect the perfect boundary yeah matt thank you so much for being here it's my pleasure thank you for having me lenny and uh congrats on all the success with this podcast it's been great same to you it's always a good sign at the end of a conversation we're like oh i gotta get me some of that stock of that gotta get into that rippling so it's a good buy recommended but you're you know hard to get hard to come by all right man thank you so much thanks thank you so much for listening if you found this valuable you can subscribe to the show on Apple Podcasts Spotify or your favorite podcast app also please consider giving us a rating or leaving a review as that really helps other listeners find the podcast you can find all past episodes or learn more about the show at lennyspodcast.com.

1:36:11See you in the next episode.