Evidence receipt / belief
Published · transcript-backedMatt MacInnis: belief
28 Dec 2025 Lenny's Podcast 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)
“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.”
Source trail
Everything needed to verify it.
- Speaker
- Matt MacInnis
- Attribution
- Verified speaker
- Claim type
- belief
- Recorded
- 28 Dec 2025
- Publisher
- Lenny's Podcast
Transcript context
…This episode is brought to you by Datadog, now home to Eppo, the leading experimentation and feature flagging platform. Product managers at the world's best companies use Datadog, the same platform their engineers rely on every day to connect product insights to product issues like bugs, UX friction, and business impact. It starts with product analytics where PMs can watch replays, review funnels, dive into retention and explore their growth metrics. Where other tools stop, Datadog goes even further. It helps you actually diagnose the impact of funnel drop-offs and bugs and UX friction. Once you know where to focus, experiments prove what works. I saw this firsthand when I was at Airbnb where our experimentation platform was critical for analyzing what worked and where things went wrong. And the same team that built experimentation at Airbnb built Eppo. Datadog then lets you go beyond the numbers with session replay. Watch exactly how users interact with heat maps and scroll maps to truly understand their behavior. And all of this is powered by feature flags that are tied to real-time data so that you can roll out safely, target precisely and learn continuously. Datadog is more than engineering metrics. It's where great product teams learn faster, fix smarter, and ship with confidence. Request a demo at datadoghq.com/lenny. That's datadoghq.com/lenny. Matt, thank you so much for being here and welcome to the podcast. Thank you for having me. I want to start with something that I know is really important to you, something you talk a lot about that I don't think people hear enough on podcasts like this, which is that extraordinary results require extraordinary efforts. Talk about why this is so important, what you think people need to hear. 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, 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. It's like the product function is an instantiation of the general concept of management. 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. 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. 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 own leadership. To make this even more real for people, what are examples of moments that were extraordinarily hard?…
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