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Published · transcript-backedMatt MacInnis: prediction
28 Dec 2025 Lenny's Podcast 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)
“Like our top 75 manager offsite 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, and that is 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.”
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Everything needed to verify it.
- Speaker
- Matt MacInnis
- Attribution
- Verified speaker
- Claim type
- prediction
- Recorded
- 28 Dec 2025
- Publisher
- Lenny's Podcast
Transcript context
…So you kicked 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 mega cities in the world. It's like, power law distribution just plays out everywhere, and once you see it, you can't unsee it. It sort of plays out in many dynamics. People tend to think that 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%, 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. 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. 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 and intend 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 over company outcomes. roof, then you have to relentlessly inject energy at every single step of the game. Teams will, sadly, but because we are all human, teams will always optimize for local comfort over company outcomes. Not because they get together and think, "We should do that," although unions do do that unequivocally, deliberately, but even in a collection of product managers or engineers, what's going to happen over time is entropy is going to creep in and people are going to optimize for local comfort. Your job as an executive, as a leader, is to fight that entropy tooth and nail every single day. It means that every time you see a bug, every time you see a bug, not most of the time, every time you go and you drop it at the feet of the product manager or the engineering manager, every time, in public, preferably, it means that every time someone comes to you to hire someone and says that they have skipped the back channel, every time you're like, "You can't hire this person unless you do the back channel," it means that when you get into the board and tired zone on any process, that you as the executive have got to demand the 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 offsite 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, and that is 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. There are plenty of constituents in the business around you who will advocate for relaxing. There is an infinite supply of people under you who will buffer other team members from the intensity of the demands. Your job is not to be one of those buffers. Your job is to preserve that intensity at its highest possible level and let the buffering happen somewhere else, and that's the point is that entropy creeps into the system insidiously and slowly over time off your radar and you have to maintain that intensity every minute of every day to try and fight it if you want to stay at the extreme right end of the power law that obviously governs the outcome of everything that we build. What does that look like to pass along that intensity? 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 off your finger. Maybe that's the example. Okay. Still got them. I got all 10.…
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