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Matt MacInnis

Published podcast speaker

Claims
16
Episodes
1
Shows
1
Named items
3

Books, apps, and tools

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book / recommends

The Effective Executive

“Okay. Two or three books. You give me a heads-up on this. So one book is Conscious Business. I don't have Conscious Business in front of me because it's actually at the office because we have Conscious Business Reading Club at Rippling. And every member of my current, my product leadership team is going through this right now, Conscious Business, Fred Kofman. 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 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 Bryan 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 in Systems, Donna Meadows. I always mispronounce her name, Donella Meadows. She died partway through writing this manuscript. Her fellow professors picked it up and finished it for her. It is the best generic framework for thinking about how systems work. You will extrapolate from this book to every aspect of your life after you read it. And then the third is classic 1960s, The Effective Executive. It's an anachronism. It uses weird pronouns for the secretary and the executive. I'll let you guess which ones. But the book itself is so chock-full of simple enduring advice on how to be effective at leading teams. And the good shit is the stuff that's been in print for 70 years, and that's one of them.”

Lenny's Podcast · 28 Dec 2025

Evidence receipt · Source ↗

book / recommends

Conscious Business

“Okay. Two or three books. You give me a heads-up on this. So one book is Conscious Business. I don't have Conscious Business in front of me because it's actually at the office because we have Conscious Business Reading Club at Rippling. And every member of my current, my product leadership team is going through this right now, Conscious Business, Fred Kofman. 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 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 Bryan 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 in Systems, Donna Meadows. I always mispronounce her name, Donella Meadows. She died partway through writing this manuscript. Her fellow professors picked it up and finished it for her. It is the best generic framework for thinking about how systems work. You will extrapolate from this book to every aspect of your life after you read it. And then the third is classic 1960s, The Effective Executive. It's an anachronism. It uses weird pronouns for the secretary and the executive. I'll let you guess which ones. But the book itself is so chock-full of simple enduring advice on how to be effective at leading teams. And the good shit is the stuff that's been in print for 70 years, and that's one of them.”

Lenny's Podcast · 28 Dec 2025

Evidence receipt · Source ↗

book / recommends

Thinking in Systems

“Okay. Two or three books. You give me a heads-up on this. So one book is Conscious Business. I don't have Conscious Business in front of me because it's actually at the office because we have Conscious Business Reading Club at Rippling. And every member of my current, my product leadership team is going through this right now, Conscious Business, Fred Kofman. 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 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 Bryan 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 in Systems, Donna Meadows. I always mispronounce her name, Donella Meadows. She died partway through writing this manuscript. Her fellow professors picked it up and finished it for her. It is the best generic framework for thinking about how systems work. You will extrapolate from this book to every aspect of your life after you read it. And then the third is classic 1960s, The Effective Executive. It's an anachronism. It uses weird pronouns for the secretary and the executive. I'll let you guess which ones. But the book itself is so chock-full of simple enduring advice on how to be effective at leading teams. And the good shit is the stuff that's been in print for 70 years, and that's one of them.”

Lenny's Podcast · 28 Dec 2025

Evidence receipt · Source ↗

Claim ledger

What Matt said.

16 transcript-backed records

01 / recommendation

Recommends Conscious Business. Recommends Thinking in Systems. Recommends The Effective Executive.

“Okay. Two or three books. You give me a heads-up on this. So one book is Conscious Business. I don't have Conscious Business in front of me because it's actually at the office because we have Conscious Business Reading Club at Rippling. And every member of my current, my product leadership team is going through this right now, Conscious Business, Fred Kofman. 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 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 Bryan 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 in Systems, Donna Meadows. I always mispronounce her name, Donella Meadows. She died partway through writing this manuscript. Her fellow professors picked it up and finished it for her. It is the best generic framework for thinking about how systems work. You will extrapolate from this book to every aspect of your life after you read it. And then the third is classic 1960s, The Effective Executive. It's an anachronism. It uses weird pronouns for the secretary and the executive. I'll let you guess which ones. But the book itself is so chock-full of simple enduring advice on how to be effective at leading teams. And the good shit is the stuff that's been in print for 70 years, and that's one of them.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

03 / belief

You have to apply the same frameworks and concepts to get people to achieve goals together. But one thing that is absolutely universal that I think we, honestly, I think we forget it in Silicon Valley or a lot of people don't sort of internalize it, is that if you want to accomplish something truly extraordinary, if you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult.

“You have to apply the same frameworks and concepts to get people to achieve goals together. But one thing that is absolutely universal that I think we, honestly, I think we forget it in Silicon Valley or a lot of people don't sort of internalize it, is that if you want to accomplish something truly extraordinary, if you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

04 / belief

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 all of them are just really wonderful people. It's just that the incentive structures lead to some real harm, I think, in certain cases.

“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 all of them are just really wonderful people. It's just that the incentive structures lead to some real harm, I think, in certain cases.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

05 / belief

We've spent a lot of time talking about intensity and the grind, and the need to just always be operating at the 99th percentile. And I think if you listen to that in a vacuum, it's very easy to believe that that intensity is soul crushing, that it's a negative, that it's maybe not something that you want.

“We've spent a lot of time talking about intensity and the grind, and the need to just always be operating at the 99th percentile. And I think if you listen to that in a vacuum, it's very easy to believe that that intensity is soul crushing, that it's a negative, that it's maybe not something that you want.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

07 / prediction

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.

“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.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

08 / commitment

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 it's literally my job, literally my job to find things, problems, and make them better, and by virtue of making those specific things better, to iterate on the processes so that the system that builds the system can get better.

“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 it's literally my job, literally my job to find things, problems, and make them better, and by virtue of making those specific things better, to iterate on the processes so that the system that builds the system can get better.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

09 / recommendation

It's got an awesome growth profile. 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.

“It's got an awesome growth profile. 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.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

10 / preference

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, which was somewhere around year four.

“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, which was somewhere around year four.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

11 / evaluation

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 and you're like, "I like that guy.

“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 and you're like, "I like that guy.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

12 / evaluation

This was a quote actually from Sunil, and he found it from a women's basketball team coach. And it is, to my point earlier about you got to run the engine at 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.

“This was a quote actually from Sunil, and he found it from a women's basketball team coach. And it is, to my point earlier about you got to run the engine at 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.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

13 / preference

So your ideal stock is a very high alpha, very low beta stock. They don't really come in that shape because alpha and beta tend to be correlated, but that's what you want when you buy a financial asset.

“So 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.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

14 / preference

" What we missed was there was a fucking feature flag, a fucking feature flag. And 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.

“" What we missed was there was a fucking feature flag, a fucking feature flag. And 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.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

15 / recommendation

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.

“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.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast

16 / evaluation

There's a line that this venture capitalist, whose name I will not mention, said, which was that product market fit is a sort of thing where you absolutely know it when you see it, and therefore if you don't absolutely know it, you don't have it.

“There's a line that this venture capitalist, whose name I will not mention, said, which was that product market fit is a sort of thing where you absolutely know it when you see it, and therefore if you don't absolutely know it, you don't have it.”
Speaker
Matt MacInnis
Publisher
Lenny's Podcast
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