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

“DM me on Twitter is easy at Stanine. You can email me my last name at rippling.com. And I'll go that far without giving out my phone number. How's that?”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Look, 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's not DJ, Lenny. It's radio personality. And yeah, I used to do the greatest hits of all time with his from the 60s, the 70s, the 80s, and a little bit of the 90s. 1015, the Hawk. Can turn it on, it's very inauthentic, but it sounds good on the radio. It's cool. I did it when I was in high school. I ended up doing the midday segment right before I went to college. And what a gift. What a huge gift in my most formative years to have developed an ability to be in front of a microphone comfortably, you know, because here we are.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's a dark one, and I'll share this one sort of partially for the humor of it, but it's actually sometimes useful. Immediately, at least it's sort of a moment of smiling when it happens. The model comes from my dad who said, Matt, nothing's ever so bad in life that it couldn't get worse. And it's like we were going through some shit yesterday at work, and we were like, fuck, now that happened. And I looked at the CTO and I'm like, dude, nothing's ever so bad that it couldn't get worse. And we had a good laugh and continued to brace for whatever might come next. So not exactly uplifting, but fun to use.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“I love my fellow coffee maker. It's got an interface that lets you set light, medium, dark rows, it changes the temperature, it blooms the coffee, it tells you how many grams of coffee to put into the basket, slick interface, high quality coffee. It's definitely awesome. And so I have Ashley have one in the office and one at home. And one in the garage.”
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 I'm a little embarrassed by this answer, but I'm going to be honest 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 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 secretly in love with each other. And they start hooking up. And it's been labeled by the media as smutty but delightful. And I would say that's accurate. 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. I said, a little embarrassing because it's very 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“I always mispronounce her name Donella Meadows. She died part way through writing this manuscript. Her fellow professors picked it up and finished it for her. It is the best generic framework for thinking about like how systems work. You will extrapolate from this book to every aspect of your life after you read it. And then the third is classic 1960s, the effective executive. It's an anachronism. It uses weird pronouns for the Enduring advice on how to be effective at leading teams. And the good shit is the stuff that's been in print for 70 years. And that's one of them.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Okay, two or three books. You give me a heads up on this. So, like, one. One book is conscious business. I don't have conscious business in front of me because it's actually at the office because we have consciousness reading club at Ripling 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. It was recommended to me by Brian Schreier at Sequoia when he was on my board at my previous company. I took way too long to take him up on the advice, wished I had read it sooner. Highly recommend conscious business changes your life. Number two, thinking and systems Donna Meadows.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Silicon Valley in 2025 is Florence in the Renaissance. Crazy, like the amount of creativity and insane invention and progress that's happening for our species right now in this place is absolutely unparalleled in all human history. You've got to zoom out and appreciate that magic. And so then you turn around and 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 have to never forget that number one, none of this matters. And number two, it is an absolutely beautiful and amazing phenomenon that we get to be alive doing this right now. So like play the sport, play it with everything you've got, but never forget that it's just a sport and that none of it matters. It's super important as a counterpoint to the intensity that we talked about.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. I think if you listen to that in a vacuum, it's very easy to believe that that intensity is. Soul crus That it's a negative. It's maybe not something that you want. And I think there's a backstop for me that I didn't talk about today that I think is important to share, which is that life is amazing. That like the fact that we all exist on this blue marble, drifting through space and time, that we are some weird instantiation of consciousness, each of us, and that you're here for such a short period of time whittling your stick, doing something 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”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“But it is a thought partner, a nonjudgmental thought partner, where in 20% of the stuff it comes out with, I'm like, that's pretty good. That's a new word I didn't think of that does kind of hit the nail on the head for this concept. And so if I believe that my job is to sort of bring brains along on the journey for some sort of change that I'm trying to bring about, then the most important tool is language. And I do find that 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.”
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, it's not a super exciting thing, but I'll say where I use, so one of the most important functions that I perform as an executive is the synthesis of ideas and the ability to communicate those ideas very clearly to people. So when I talk about like the product quality list and the pickle as something that we've come up with internally, I do turn to AI, ChatGPT and Gemini, where I take like a really, let's say, angular view of some topic and I give really I write the essay for the AI and I'm like, look, this is the crisp idea I want to communicate. Help me come up with pithy ways to articulate these things. And 80% of what it outputs is trash. It's just like sort of middle of the road average low alpha junk.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Like, I actually think that if I were to give you an answer to this question right now, it would be bullshit. I don't have back to my point earlier. I don't have enough relevant experience in the abstract to dole out on a podcast on that topic. But, you know. I wish them”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Some really interesting investors out there who I think are thinking quite deeply about this, and in particular. 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 that's kind of narrow. Uh, now I'm like, no, no, no, that was the right move. And like, 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”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Because look, SaaS software is a bit flipping. All SaaS software applications are bit flippers. It's an interface in a database. It's what it does. Really hard problem like rippling one of Rippling's superpowers is where a coin sorter, you dump 20,000 dollars 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. It'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 Wally. It's going to be great.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“You're in a very difficult place from an economic standpoint because you're not going to be permitted by either of those parties to build a big business on their backs. That's just not how it's going to work. They're going to demand value capture that crushes your unit economics. So I look at the landscape of AI companies that I've seen. And I think you have to have a really durable, interesting insight that gives you a shot at viable unit economics to be an interesting business. And that is going to kill off. 80 or 90 percent of the stuff that I see right now as standalone AI businesses.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“The biggest HCM software company you can think of integrates to the other biggest payroll software company you can think of through flat files via SFTP. What are they going to do? What are they going to do? It's just never going to work. It's just no way. And so I literally have no idea what they're going to do. They're just not going to build AI software, I guess. Point SAS is sort of in a rough solution, in a rough spot, especially when you cleave to really important systems apart and say they have to integrate. It's very, very hard. The other thing that I would say about the world of even just like not SaaS but AI software is that point solutions in the AI world are also in a rough spot for the same reason. It's like if you're selling the shovels like OpenAI and Google with Gemini, you can make money. And if you own the mine like Rippling with the data, you can make money. If you're somewhere in the middle building AI software that then tries to use the shovels from the shovel provider, but then also needs to rent out the mine or get the ore out of somebody else's mine and start refining it. Like you are in.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“No, I think the gist is. A really good quote. I forget who it was attributable to, but it's two ways to make money in software bundling and unbundling. And you just got to get the timing right. So, this is a period of bundling. Points, so here's the problem. Point solutions don't have enough data in the age of AI to be useful. 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.”
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 going to vibe code their way to their payroll system, which I know. Good luck to the employees of those companies”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Riplaning, where less than 1% of the market. And so in 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 sass in terms of what we're building.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Pretty magical things. So we do payroll, we do HCM, we do IT, we do spend, we are about to launch a new product in the category of business intelligence and data management. And there's a whole bunch of other stuff coming beyond that. And then you layer in AI on top of this, where we alone 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 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 Ripling is jaw dropping. So I'm super excited about the tailwind this is going to create for us. You ask about like sort of.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Is who's doing stuff? Who owns it? Who's accountable? And so the people record is a really important component of that. You can argue that the customer record is also very important. And of course, some big businesses have been built on that primitive as well, but we think the people primitive is actually much more important. And the only thing that hasn't been done here is like somebody hasn't been ambitious enough to build a good business on top of that primitive workday is terrible software. Everybody agrees on that. If 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. Like 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“People look at Rippling from the outside. I think they think of us as like payroll in HR or whatever, which is cool. It's a bit like saying Microsoft is a desktop operating system company or it's like every company starts from somewhere and grows out from there. We see ourselves as building the most successful business software platform in history. In fact, that's the mission statement of our product organization under the umbrella of the mission statement of the company, which is to free smart people to work on hard problems. And like when you translate that from where we are to data where we think we're taking things, it's like we really do believe that the core of every workflow and everything that a company has to do, be it AI or manual traditional GUI-based software.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“That I'm just like, I've got them queued up on my to-do list today, and I'm going to take them to the product teams directly and be like, I'd like to understand what happened here, not in a negative way. I just think we'll all get better if we study this one. And so, yeah, escalations are a gift. Feedback like that is a gift and nobody is ever inconveniencing me when they do it.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Have an escalations team at Rippling, which sounds weird, but it's people who are just particularly skilled at pistol whipping other people in the company to get to real root causes, real root causes, not like throw away the word root cause. Like, oh, we fixed the data error and shut the ticket down. Like, no, you went and you found the software that created the data error, and then you found the system that created the software that created the data error, and you saw all of that back to the top. escalation seems extremely good at that at rippling. So we have sort of a dedicated little team that does this for us. Escalations are a gift. And it's like, if you're a listener right now on this podcast and you are a Rippling customer and you have shit that you think we should know, the fact that I might already know it is not a reason for you to withhold the gift of your feedback. So it's an attitude that I take to this every day. I've got a little queue of some stuff that minor things that are from the last couple of days from people who said some nits and issues.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“The part of this that has been interesting to me is that people withhold, escalate, the customers withhold. Customers don't want to escalate to me as an executive. Even the founders in whose businesses I've invested who use Rippling are reluctant to hit me up when something goes wrong because they don't want to bother me. But is literally my job, literally my job to find things, problems and make them better? And by virtue of making those specific things better to iterate on the processes so that the system that builds the system can get better. There's no greater gift to me as a product executive than receiving an escalation from a customer.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Fundamentally, the most selfish thing you can do is withhold feedback from someone who are you optimizing for when you do that? What are you optimizing for when you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable? Well, you're optimizing for your own comfort. And it's fundamentally selfish. It's the most selfish thing you could possibly do is withhold feedback that would otherwise be useful to someone because you don't want to be uncomfortable. Well, that's not how high performance teams operate. So I demand feedback And I give it And doesn't mean that when I give feedback, it's not open to being questioned or discussed. I mean, of course, it is. But like when I observe something, I try to say it. That's the feedback topic.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Man, there's a whole other podcast episode on the concept of leverage. You sell your time, you've only got 24 hours a day to give. But if you can create a product that scales. The marginal cost of a unit of that product is zero, like software. It's going to be competitive, man. Sell your time. It's not going to be super competitive, but like sell that, achieve that level of leverage. And there's just going to, it's a pretty efficient market.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. I mean, again, if you're chill and you move the x axis down 10 or 20 points, the y-axis collapses. Don'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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Reaction is, oh, that is so invigorating. It's like so wonderful to hear that we're going to achieve these great outcomes, or at least we have a shot at doing so, and that you're empowering me to follow my instinct, which is to really push for the best result. The reaction universally is like, ugh, what a relief that I get to go be intense because nobody in a position of leadership wants to be chill. And 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 till p.m. Don't be chill. Chill doesn't accomplish shit. Be intense. Be good, be respectful, be intense. Don't be chill.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
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 was Parker Conrad 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 if you've ever been dragged into it, like, I want to talk about this fucking problem right now and whatever you're doing, unless it's an interview, like I want you to come and have a conversation with me. That intensity is one place where it plays out. Every product team at Ripling, and we have a lot of them now, have public feedback channels. I am in there upside down on everything I find when I use those products and I just model for everybody that this is how 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, you know, boom, boom, boom, boom, boom, and people jump in and respond. The factory inspection process that I mentioned, which is where at the end of the assembly line, I jump out with the pickle and we talk about all of the elements. You have to record a loom of every major flow through the product. I personally review every one of those flows. I got a backlog I got to catch up on today.”
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 all tech. I'll give you concrete examples. Actually, the joke that I sort of played on this one when I presented to the team was that the next sort of slide in my presentation was with the sound effect, the slack huddle thing. And Parker's icon in Slack is just, he uses the generic yellow. 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, which is the sound that Slack makes when someone calls you.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Your job is not to be one of those buffers. Your job is to preserve that intensity at its highest possible level and let the buffering happen somewhere else. And that's the point is that entropy creeps into the system insidiously and slowly over time off your radar. And you have to maintain that intensity every minute of every day to try and fight it if you want to stay at the extreme right end of the power law that obviously governs the outcome of everything that we build.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“That is fucking dangerous because if you go to two layers and it's two orders of magnitude, drop off and signal and intensity, that is a very dysfunctional organization. So what I say to the team was it's not that you need to buffer people from the intensity of the CEO. It's that you need to absolutely mirror that intensity. Are plenty of constituents in the business around you who will advocate for relaxing. Is an infinite supply of people under you who will buffer other team members from the intensity of the demands?”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Means that when you get into the board entire 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 like if the purest form of ambition and the purest and most intense source of energy in the business is the founder CEO At every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Not because they get together and think we should do that, although unions do do that unequivocally, deliberately. 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 fee of the product manager or the engineering manager, every time in public, preferably. It means that every time someone comes to you to hire someone and says that they have skipped the back channel, every time you're like, you can't hire this person unless you do the back channel.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Does this have to do with product? This is really about effort. Only antidote to entropy, the only antidote to decay in a system. Is energy You got to inject energy. So if you have a code base, every line of code that you add to that code base increases the entropy of that system and demands ever more energy from human beings to go 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. You have to relentlessly inject energy at every single step of the game. Teams will sadly, but because we are all human, teams will always optimize for local comfort. Over company outcomes.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Don't just get 10 or 20% more reward. They get 10x the reward or 100x the reward. It's really dramatic. Entropy, the second law of thermodynamics, is a very simple concept. It's the reason your sock drawer becomes messy. It's the reason that potholes form. It's the reason we have to put so much energy into maintaining the aircraft we fly to keep them safe because they really, really, really want to fall apart. And that's the nature of things. If you abandon a city for a few months, it starts to go fallow. And so entropy is just this concept that shit tends toward disorder. The universe, I mean, life itself is a temporary victory against entropy. You and I should not exist. The sun gives energy to the planet. It organizes stuff that we can eat. And we fight entropy until we lose the battle somewhere, as I said earlier at the age of 70 or 80, if we're lucky.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Man, understanding the nature of the universe is a pretty good way to work within it. And so power law distributions happen everywhere. It explains why so few people control so much wealth. It explains why Steph Curry is just so vastly better than the next guy down on the list, on the basketball team. It explains why populations are concentrated into a relatively small number of megacities in the world. 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, but that is absolutely not the case. And the implications are profound. It's like if you build something to 80 or 90%, the Y axis is barely budged yet. You haven't hit the inflection point in terms of reward. And so the implication of the power law more broadly is that people who are in the top 10%, the top 5%,”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“We don't spend time on it, but I think it's actually a really good question. But yeah, like, what are some of your favorite investments? Show me the logos.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm in Langchain. Like, great. So, those are some companies that you maybe have heard of. But how about like I invested in macro. Founder was Derek Lee. Macro's out of business. I invested in debrief Ned Roxan. It's out of business. I invested in verb data with David Hurts out of business. I'm reading from a list. I invested in, what's the number? 70 companies according to this list where I track things. And like most of them went to zero. And all those founders were awesome. All those founders were kick-ass. And all those founders put a shit ton of energy into building their businesses and they went to zero and they're enduring relationships. I can call on any of those people, I think, maybe with the exception of Deal and call in a favor and have, and I've, you know, I've got a few subsequent, and actually a lot of them joined Ripling, 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“I was able to exit that position, and then hopefully that company is going to zero with their criminal behavior, but whatever. I was more recently if you know Decagon, which is doing some really cool stuff on the AI front.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“First of all, okay, so I sort of hate the question, what are some other companies you've invested? It was a fair question, but the problem is like I'm going to give you a bunch of companies I've invested in that won, you know, that are like really notable. So what I would like to do instead of answering that question, I'm going to give, here, let me give you some like some bait. I was one of the first investors in Notion. I was perhaps the first, I don't know, ask Ivan clever, which had a great exit. I was one of the first investors in Xenophon's, if you've heard of it. I was before I joined, one of the first investors in Ripling. 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.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Give up or don't give up 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. Idiosyncrasies of the founder. Rippling succeeds for almost the polar opposite reasons that notion succeeds, but in both cases, the companies succeed on the idiosyncrasies of the founder. And so embracing that, recognizing those idiosyncrasies, that's what great investors do. They spot that element of spikiness and greatness in a candidate investment, and they convert that to a commitment. And then, of course, the investor, the good ones, accept what they get in exchange from that for the universe, from the universe.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“These guys stuck with it. They went through hell. They pivoted. They went to Japan and sat in kimonos and meditated on what they were going to build. And by hook slash crook, they got to where they are today as a really wildly successful business in an extraordinarily difficult market where building businesses is virtually impossible in productivity. It is dominated by Google and Microsoft 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”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Is absolutely true. And when I give these general observations on the patterns in Silicon Valley, the most successful businesses inevitably violate something on that list in some really important way And so notion you can't replicate Notion's success as an entrepreneur. 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. 2011”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Let's talk about alpha beta again. 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 found or does it have, is it a C-corp in Delaware? Like, you know, boom, boom, boom, boom, boom, boom, boom. And these checklists are all about what? They're all about suppressing beta. They're about avoiding avoidable mistakes. They're about bringing stability. Jeff Lewis is an investor who has many angular views on things. And I think one of his most enduring phrases is narrative violations. This idea that like the common wisdom must be violated in some way by every company that has an outsized success”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. This analogy of drug discovery and binding receptors is like nobody at Genentech thinks they can market their way to better performance inside your body. The binding receptors for that drug, they exist or they don't, and when they build their product, their goal is to find out whether the binding receptors exist. But fate already has decided the outcome. This is absolutely true, every software product you build. Fate has already decided the outcome. The market's either going to latch onto your product and run with it or it's not. Do not ship the product, find a lack of success, and then try to market your way through that because the binding receptors likely don't exist. And for me, it was a very liberating mindset because now I just have to find the right drug and I can forget trying to convince the body to develop the binding receptors for whatever it is that I'm building.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source
“Think to myself, like, this is not what this is about. Like, this is not how great companies are built. It can be a nucleating event, but it's not a major thing because nobody cares about your company. Like, your launch doesn't matter. Big, fat pull the 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 or you think about all the effort you're putting into building a product that you believe is going to have product market fit? Well, if you recognize that the market is immutable, no amount of tweeting LinkedIn, posting, advertising is going to change whether the market wants your product. It might raise awareness about your product, but it's not going to change whether somebody wants it.”
2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source