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Lenny Rachitsky: evaluation

26 Oct 2025 Lenny's Podcast How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

“Like, "Okay, cool, we built it in a weekend and now it's years of endless maintenance and requests and support.”

— Lenny Rachitsky

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Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
evaluation
Recorded
26 Oct 2025
Publisher
Lenny's Podcast

Transcript context

…I think there's a trap in getting away from your core purpose as a company. And our core purpose is economic empowerment. So getting customers or merchants or artists the ability to make a sale or pay their rent or upload their latest creation to TIDAL. And I think that anything that serves that purpose, we should encourage and we should invest in, but if we're just purely looking at dollars versus dollars, then that's pulling us off that purpose. The savings and costs that there might be in replacing a vendor tool by something you build in-house is probably not worth it in the mental bandwidth that you've lost and the amount of the team's technical focus that's being taken away. So yeah, I would say it just keep coming to the thing that matters to you as a company and then the rest will follow from that. Yeah, I think people forget just how much maintenance it takes to keep something you've built. Like, "Okay, cool, we built it in a weekend and now it's years of endless maintenance and requests and support. " And also to your point, it feels like it comes back to the always motto of just focus on your core competencies and then buy everything else. Yeah, it's the classic 80/20 problem, and we have that enough with the apps that we build for our customers. We'll build some great experiments that really resonate, and then we have to spend a lot of time ironing out the long tail of problems. So in Cash Card, for example, we built the entire functionality of Cash Card, I would say pretty much in a weekend or maybe a week of integration and work. And then it took a really long time to iron out all these edge cases where someone would tip twice the value of the bill and then it would completely break something in the back end, or people would use it as a gas station and they have a different way of billing your card. So yeah, it's very much that. And to your point, I would always come back to what is the reason we're doing this? Why does it matter to us and to our customers? And if it doesn't clearly satisfy that, I would just push it off as a not interesting thing.…

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