YouSaid · the spoken record

Matt MacInnis

lines on the record: 110
first: 2025-12-28
most recent: 2025-12-28
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Oh, yeah, yeah. I think this is like a really fundamentally misunderstood dynamic. When founders messaged me and they're like, hey, 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. It doesn't matter. But I do that. And then.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Which was somewhere around year four. It is, of course, very important to believe in what you're building and to be persistent. But there is definitely no shame in saying, look, we've pivoted once or twice. It's not catching. I got to go do the next thing. And I think if you're year four, you're five and you're entrepreneurship journey and it's not just obviously a screaming, rip-roaring growth story. It's extraordinarily difficult. This is so extremely rare. So beyond even already the rare scores you're going to face from the outset that now is going to convert to something crazy. So that's hard to hear, I guess, but man, it can be really liberating when you're like, fuck it, I'm going to do this. I have the energy. I'm going to do it again. I'm just going to do it with a clean sheet.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“If you ask them for advice, they will always give it. But if you ask them for relevant experience, they rarely have any to offer. And if they don't have any to offer, then don't ask for their advice. So ask people for relevant experience, and I try to do this with my own entrepreneurs when I work with them. It's like, let me offer you whatever relevant experience I have. And my relevant experience on this topic of when to quit is like, I think we could have called it after the second or third pivot.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Here, look, history provides us with a clear guide. When you look at companies having hit it big, they hit big pretty quick. It's very, very dangerous to be late to the party. It's very, very dangerous to be early to the party. And the vast majority of the time, that's the problem. Rippling had it been started in 2014 would not be what it is today. I think Rippling had it been started today would not be what it is five years from now today. And so I think like timing is a lot and it's very hard to control for. But when you get the timing right and the market is real and the product works, product market fit. 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 the rocker anyway. They're a very bad investor. Sikh 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“I got more where that came from. By the way, it's not anti-VC. It's anti-VCV. It's the incentive everybody's acting in accordance with their incentives in Silicon Valley. The executives, the founders, the 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. Trust me. The 45-year-old entrepreneur or the 50-year-old venture capitalist who have been in the game for a while, they get it. They've observed it. They know what it's like. The system is there to take advantage of the people who 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, which is really wonderful people. It's just that the incentive structures lead to some real harm, I think, in certain cases.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, 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. 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. 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?”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“And so the only logical desire that they would have is for you to keep trying. Against all odds, because there is the occasional example where someone pivoted from A to X and it was wildly different and it worked, slack was originally some sort of a gaming company and became corporate chat, you know, Airbnb maybe. It's like there's some examples of companies having made wild pivots and succeeded. But man, is that rare? I mean, just so exceedingly rare. And I think it's important to remember, like 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“I've invested in like 60 companies or 70 companies. I don't know. It's not something I actively do, but opportunities by virtue, I think, of my role at Ripling sort of show up. And I talked 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 I read the updates from them that I sent to my investors in 2011 and 2012. I'm kind of heartbroken. We talk in Silicon Valley about never quit, but that is complete, absolute venture capital bullshit. Incentive of venture capitalist is to put money into your company. And milk you dry. Never get their money back. There is no way for them to take that investment back.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“There's a line that this venture capitalist whose name I will not mention said, which was that product market fit is the sort of thing where you absolutely know it when you see it. Therefore, if you don't absolutely know it, you don't have it. 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. In hindsight, with the benefit of now having experienced solid product market fit, it was so, so obvious that we didn't.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Like, look, I love wine. Wine is one of my things, and I've learned a lot about wine. One of my favorite lines, like, I don't like Chardonnon. Like, no, no, no, no. Chardonnay's the most fucking amazing varieties of wine in the world. You just haven't had good chardonnay. And there's a Chardonnay out there for you. Product management. It's like, you don't like product management, you think product managers suck. It's like, well, you just haven't had a good chardonnay yet.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“And now that I lead product, I'm like, oh wow, this is the high order bid. Not that I didn't sort of understand that, but like now I really get the 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. 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“A CO My job was to accept the product as it was and optimize everything around that. Job was to make sure that the product operations in our business, the interface to the insurance carriers, the interface to the payment entities, the government regulators, that stuff all just sort of worked. It was to make sure that our sales engine, our marketing engine, all the go-to-market stuff optimized itself around what the product was. It was about recruiting and making sure we got people in to work on the product. You kind of go down any function that isn't in R&D, and I had some hand in trying to figure out how to make that function work to the best of its ability given what the product was.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 talk about the mini CEO. I think it's kind of a stupid misnomer. But there's some wisdom there. And I think the wisdom is that you have to be a polymath. Like you've got to be really good at working with other people. You've got to be good at communications and articulation. You got to be good at project management. You got to be good at the science and the math and the engineering. It's really fucking cool. And so I think one of the great joys of this job for me has been interacting with the tippity top of the smartest and most polymathic people in the industry. I'll say one other thing about what I love about leading product, which is”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Lot of the sort of basic human interaction models. You never think that giving someone an impossible task and even including the L5 person versus the VP on the same thing would be productive. And let's just say our recruiting team still sort of covets a bit about this and feels like we eliminate people too aggressively at this stage of the interview process. But I've found the wisdom in it and think it's actually quite useful to give everyone the same simple, complicated prompt and just see hand them a drill bit, give them the concrete wall, and see if they can get a millimeter or an inch into the concrete. 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 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 it was 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Everybody comes away from that interview feeling like poop, like they had failed it. Whereas on our side of it, we're like, wow, that person got really far. They saw around three or four corners in a really impressive way. There was 10 they didn't see around, but they saw around four of the hardest ones. And they were not defensive when we gave the new information that called in the question the validity of their solution. And they were willing to interrupt us to ask more questions. And like a”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“When I first started working in the product organization, I was introduced to a 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Spotak isn't by itself a good top down framework, but when you're thinking about, oh, why did I not, why did this candidate just click? Why did I not like them? You go down the list, you're like, oh, yeah, no, this person, it's that they were not excited about the idea. They weren't passionate. It's that they talked shit about their previous manager and that they were a victim of the performance of their last two companies. That's what it was. They're not optimistic. The framework is super useful to evaluating people. And I think the alpha beta framework is also super useful when you come away from a conversation. 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Spotak. It's a very ugly acronym. There's a hat tip to somebody out there in the universe who originally thought of this as not me, but I adopted it. And it's that people are smart, passionate, optimistic, tenacious, adaptable, and kind, those five things. Six can't even count. I told you I lost a finger, right? When I made a mistake, so that's down one.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 talk about hiring for a second, I think. I've spent a lot of time with teams at Ripling talking about how I hire. It is born of batting practice. It'd be super interesting to actually be able to rewind the tape on my life and sort of contemplate how many candidates I've met in every context. Many thousands, maybe tens of thousands. I don't know. It's a lot of batting practice and a lot of model training in my brain. 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. If you have a good intuition, you should absolutely rely on your intuition.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, we're willing to accept a bunch of volatility in this area in exchange for the upside we'd get from the creativity and risk taking of these people or these lack of process that sort of gives them the latitude to do what they want to do”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Are allowed to have one future 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 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 across one go into 2,000 technical workers.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a feature flag. He gets a blank screen when he installs the application. What did I do? My reaction was ug. 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. Future flags. And so I added a line to the pickle that said.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Companies. And he installs it and he goes in and it dumps them onto an empty screen. And he's like, what the fuck is this? What is this? What's going on? 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 without fucking in front of it because feature flags are the bane of my existence and the worst things in the world that constantly cause problems. Engineers put one in temporarily and forget them. 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”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Lightweight in the sense that it just articulates in the simplest ways the standards we want you to meet when you ship a product. Doesn't apply to every product, not every line applies to every product, but it's comprehensive and it provides me with a framework for iterating over time as we learn. And so just yesterday, we shipped the product to Parker. This is part of our process. When we ship a new product, it goes to Parker, who is the big admin for rippling at Rippling. If you're not aware, Parker is the sole payroll administrator for rippling for all five thousand two hundred employees. He personally runs payroll always. There is no exception for all fifty two hundred 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 another feedback.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“And it forces them to break it down into its constituent parts. And if they can articulate it clearly without using that word, I know that they know what they're talking about. And if they just fumble around with the word strategy again, I'm like, okay, you actually haven't thought this through. And so with the pickle, with the product quality list, it's like, I could come up with some generic term for this. But I really want a new joiner at the company to understand that this is an idiosyncratic thing to Rippling. This is unique to us. You 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”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, well, sure, a meme. A meme is actually a good example of this in common culture. In pop culture, I think like, Why when people come to the table with ideas from the outside, I welcome those outside ideas. But if the first thing I ask the person to do is to tell me what they mean without using those words. So when someone comes in and says, hey, I want to do this thing on strategy. I'm like, cool, tell me what you mean without using the word strategy.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. It's a big ship that we have to steer. If you want to create a moment that sticks in people's brains and sort of becomes a zeitgeist or something that they latch onto, you got to create an entity, a vessel for meaning, and then you got to fill that vessel with your meaning.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 Lobeta. So examples of this are, let's say, our product quality list, which we lovingly at Ripland call the pickle.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 outsize return relative to whatever the default solution is. When you have a more mature product or if you have somebody in the product operations group or whatever, you probably want a more low beta environment where it's like it cranks it out, it does it very reliably. Our payroll product, we badly want the payroll product to be very low beta. We really don't want the payroll product to have any unpredictability or aberration. And so we're willing to accept more process. And here's a fundamental principle of design in an organization, which is that processes, processes in a business exist for the sole purpose of lowering beta.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Give you another framework that I like to use. 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. Beta is just volatility. Beta's not good. A high beta stock jerks around for no particular reason. It's like discorrelated with the index. It just, you know, it's very high beta. Great if you're an options trader, but other than that, it's not really something you want in an asset.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Tracking system, a recruiting product because it's in a really good place from a usability standpoint. It's very well instrumented. It's got like very happy users. It's got an awesome growth profile. And so we should be really focused on the adoption metrics because I think that's going to be an important ingredient to low churn over time, removing friction from the implementation process as an example. There are other parts of our product where I would say I don't care at all about adoption and am much more focused on foundational things like I said earlier, test coverage or whatever, just to make sure that the thing is stable and good and delivering exactly what it's supposed to deliver to deliver once it's adopted.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Greater trust in my own instincts, the sort of patterns I've matched across other functions do indeed apply in product, but I have both the advantage and disadvantage of not having led a product function before and therefore must think about every problem from first principles. I have no choice. I can read shit on the internet. I can like listen to clear thinkers on topics and import their ideas, but I'm very reluctant to import an idea without breaking it down into its constituent parts and figuring out how it applies at Rippling. And so I don't actually give a shit about adoption metrics as a matter of principle. I care about adoption metrics when I care about adoption metrics. Like I realize that that's a tautological statement, but it's like, I'll get there. And so in certain parts of our product, I really do care about adoption metrics. I care a lot about adoption metrics in our applicant.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“The lesson is Everything Must be done in its time and order. And you can move really, really quickly. There's no sort of excuse not to move with urgency on all of these things, but you got to do them in order. And you have to lead bottom up. Like you got to lead from the specific circumstances you observe. And I think for me, one of the best things that's happened over the last 11 months is that I've gained”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“For our customers, but I feel, as I said, a little dumb for the way I was thinking about it before I jumped into the deep end. There is just no excuse as an executive for sitting outside of the mess and thinking you know the answers. It's a cardinal sin as an executive to do that. You need to go and see. You need to be in the boiler room. You need to study the system bottom up and develop hypotheses for how to amend the system. And that's what I've been doing.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Elements of that hierarchy higher up the triangle and sort of impugn the failure of that organization for not, as an example, measuring adoption metrics very carefully and not closely tracking those metrics as a means by which to drive execution. When I jumped in, I was like, man, we need to establish some basic standards for test coverage. We need to establish some basic standards for how we do what I call a factory inspection on a product once it's ready to roll off the assembly line. Do we have a checklist for what we call product quality? And what does product quality mean? Those basic things weren't there. And so the idea that we should be spending time measuring adoption metrics is absolute insanity. You're skipping a lot of steps between here and there. And so we have made great strides. And I think it's translating to product quality improvement.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Job of managing their specific domains. Jumping into the product role has been. Quite eye-opening I feel a little bashful about the naivety of my view from the outside a year ago. Product teams have a hierarchy of needs. And we like to sort of point at the failures to meet.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Jumping into the product role when the product function itself, although staffed with really talented people wildly understaffed and without a single spiritual leader on top of it to drive consistency and process excellence had become locally optimized but globally incoherent. And if you know Conway's law, you are destined to ship your org chart. And so with a locally optimized, globally incoherent team, you had a locally optimized globally incoherent product experience that needed to be resolved. And so my efforts over the last 11 months have been to establish greater clarity in terms of how we do things around here, better process, better general leadership, hiring and firing. I mean, just doing this sort of cleanup on IL-3 that needed to be done, even though a lot, again, a lot of the people in the team were quite talented in doing an excellent.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Agree that they weren't the right people. We had a hiring mistake in engineering leadership where the product leader at the time had to sort of run engineering. We subsequently had a mistake in product hiring and a lot of us had to sort of pitch in. And Parker and I sort of stared at each other through two years of this kind of disarray or this chaos or this agony of things, just never really having good executive leadership over both engineering and product at the same time. And I remember Parker sort of slumped down in his seat and said, oh, fuck, I have to run another search. And I said, no. Like the gig's up, I'm going to go do it. And he really sprung up in his seat. He's like, really? Like, you'll go do that? I'm like, dude, this is what the business needs. And so that's what I did. And that really started about a year ago in sort of, I realized I was going to do it and express that to Parker in December. I really took it on in January of 25. And so it's been 11 months of learning.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“I did that everywhere except RD, I would think about helping out with components of the sales organization, like our channel team, or I spent time building out the recruiting function a few times when it needed to be sort of rethought in response to our growth. But 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 the smoke takes various forms. And when you're growing as quickly as rippling is growing, it's not always something that necessarily even impacts customers, but it's the sort of thing where you're like, fuck, that architecture is not right. Or they're not measuring adoption correctly. From the outside, I actually had quite a few criticisms that I could lob in. And what happened at Rippling was we made some hiring mistakes. I think the folks that we had in those roles would have”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Story at Rippling is pretty interesting. And I'll tell it because I think it explains why I'm making this transition, but this isn't really about me. I think it's sort of a pattern that your listeners would find useful. In general Your best executives are the ones that you can mostly toss into any challenge and they will bring order to chaos. They will fix the thing. And I do appreciate the terms that people have used at Rippling for me talking about McGuinness'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”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Good luck to you. The odds are not in your favor. But the folks who, when I look at a resume and I see that someone's joined, they were at really good companies when those companies were super exciting and in crazy growth mode. I'm like, I instantly want to interview that candidate because I want to hear what they learned from being part of a winning team. And that's sort of one of my go-to heuristics when I'm looking at candidate profiles. And I think it's an undertold trope. Sorry, not an undertold trope. It's a piece of advice that I don't think people embrace enough in the valley that success begets success and you should chase success.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“And it's more informative. Like there's more to glean from seeing how it's done right than there is to glean from seeing how it's done wrong. If I tell you you're going to get on an airplane and one maintenance technician has seen it done right a hundred times and the other As an early career product manager, or why like.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, one thing that I've learned from Parker is Parker's our CEO at Rippling. He said you don't really learn from your mistakes. You learn from your successes. And it's like, you do, of course, and he would admit, you learn a bit from mistakes, but I do think that this is sort of feel-good bullshit that's like, well, you didn't succeed, but at least you learned something. I've had failures. Like when I look back at the nine years I spent working on inkling from day one in 2009 until we sold that business to a private equity firm in 2018, up the curve of Silicon Valley coolness back down the other side into obscurity. Like, of course I learned and grew a ton during that time, but in now what I think is six or seven years, I'm trying to do the math, seven years coming up on at Ripling, 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, this was a quote actually from Senil, and he found it from a women's basketball team coach. And it is, to my point earlier about like, you got to run the engineet 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 watch very little of it, is a very, that military.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“And sort of knowing the difference between those two things. And so that's the way we work at rippling. Everyone is constantly asking for more resources. And of course, where we can afford to and where it's appropriate, new resources arrive. But it is really important to me that we feel that we've deliberately understaffed every project at the company.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“People working, I think most importantly, on things that are further down the priority list than necessary, you have 20 things on a stack ranked list and you know that you got to do the top five, but the next 15 down is kind of ambiguous, but you've overstaffed the project. So like the next 10 things down are getting worked on before you even know if they're necessary. That is poison. It's wasteful. It slows you down. It creates cruft. And so it's very clear that understaffing is less evil than overstaffing. In this particular framework, the advice is understaff deliberately, always. And then the wisdom, the wisdom element is to know not to understaff.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“So here's a management framework that I used fairly often As an executive, you don't know how to get any decision exactly right. It's not knowable. You don't know how much budget to allocate. You don't know how many people to put on a project. You don't know how to set a deadline for when you're going to ship something. But of course, you have to set some default. So you make your best guess, and then you manage to that best guess. And you learn as you go. Because in software development and in business in general, everything's emergent. These are not things that are knowable top-down or a priori. And so you take a best guess. And knowing that you're not going to get the right answer, you need to decide whether over steering or 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 understand. If you overstaff, you get everything you just said. You get politics.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“People are human beings. You can't grind the individuals down, but the team as a collective group of people has to be sort of on the ball all the time. There can't be a break. And if you leave one, you're just begging for the slightly more hungry competitor to community your lunch. And that's the beauty of capitalism.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source