YouSaid · the spoken record

Matt MacInnis

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

  1. “I spent seven years at Apple and learned under Steve Jobs when he was the CEO, learned what we called the death march, which is what we did to the engineers. It was like as soon as you shipped one version of the iPhone, like you were just immediately thrown into the pit of building the next one. And there was no break. It was just relentless. And talk about an extraordinary outcome at the end of the day. There is no relief. It just like every in a competitive market and if the market is valuable, it's competitive. No question. If you leave anything on the field, if you sort of leave a crack for your competitor, like 100% chance they're going to go fill that crack. And so you have to be relentless. There can be no relaxation of the organization. It doesn't mean people can't come and go or people can't take vacations or sort of live their lives, of course. And you can't, it's not like.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “But if there's no chance at an extraordinary outcome, it's very hard to get the extraordinary effort. And so I like to remind people at Ripling at least, like it's so rare to have the opportunity to be able to be a part of a team where the extraordinary effort that you do put in on Friday or whatever, whenever it is, is actually contributing to an extraordinary result. It's a very special and rare thing and it gives me a superpower as a leader because I can lean on that when I'm wringing the oil out of somebody who's in the board and tired zone.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Not perfect and not great. But the growth rate of the company on the revenue foundation that we have is extraordinary, like really, really compelling. And it gives you as a leader the air cover to get up in front of your team and say, hey, guys, I need the last ounce of oil that you've got left. And if your company's not growing very quickly, if things aren't that great, if your growth rate is 30% or 40%, you know. It doesn't feel as good as a contributor in that business to lean in and give everything you've got on Friday or Saturday or Sunday because you don't know that it's going to yield much. And so extraordinary results outcomes demand extraordinary efforts.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “It is not about any sort of grand single story. I think the truth, the story is actually told through a thousand little things. And so for me, the story is told through a thousand JIRA tickets, not through a thousand grand events. The extraordinary effort thing is a reminder that it's supposed to be really freaking exhausting. It's supposed to be. So on Friday night, when you get hit with an escalation on Friday night, when you get sort of hit with a bunch of new bugs from someone in the engineering team that you've got to triage, those are the moments where great players and great teams are separated from good players and good teams. And it's so easy to say to sit at a company like Rippling because we're winning. As a company for all of our foibles, and we should spend time today talking about where things are.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “Product function is an instantiation of the general concept of management, like being a chief product officer is not that different from being a chief whatever officer. 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. Like it's going to be really uncomfortable. And you got to sort of remind people of that, that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. Like they have definitely screwed up somehow. It's not that an extraordinary effort is sufficient to an extraordinary outcome, but it is 100% true that it is necessary. And so I do use that framework as a sort of guiding principle in my.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “I mean, this is a term that phrasing I actually attribute to a friend of mine, Dan Gill, who's the chief product officer at Carvana, which as a company also doesn't get enough credit for how much of a tech company it actually is. Super interesting. And I think as a general framework for me, not just, and a lot of what I say with you today is not really specific to product in any way. We should actually talk about that.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “Teams will always optimize for local comfort over company outcomes. The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity. That is fucking dangerous. As an executive, as a leader, your job is to preserve that intensity at its highest possible level.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “Fundamentally, the most selfish thing you can do is withhold feedback from someone. 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.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “You want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. You got to sort of remind people that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. It's supposed to be really freaking exhausting.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “It is really important to me that we feel that we've deliberately understaffed every project at the company. If you overstaffed, you get politics, you get people working on things that are further down the priority list than necessary. That is poison. It's wasteful. It slows you down. It creates crust.”

    2025-12-28 · Lenny's Podcast · 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · IDENTIFIED FROM THE TRANSCRIPT · source