Lenny Rachitsky: uncertainty

Transcript context

…It's becoming so hard to have contrarian views because I think the algorithms just try and get contrarian views out of people with an insane force. Depending on the era, this may not be contrarian, but I think that inclusivity isn't always all that great. I think I very much believe in small group theory. I think the world is run by group chats of eight people or fewer. And so sometimes it's great to be exclusive. And what I mean by that is I even think about this in terms of Notion. Notion could have the ambition to say, "We are going to have eight billion users." So every single person on the planet uses Notion. And I think if we did that, we would very much upset the first, call it, 500 million because the top of the class wants different things than everybody and everybody is in the top of the class at something. And so I think being okay with being exclusive sometimes is okay. I will have to caveat this with, if you're McDonald's and you have exclusive hiring practices and it's the only job in a location, that is not what I'm talking about. But going back to comfy, air-conditioned job kind of thing is like, great, just work with and for the top of the class is sometimes a winning thing and just build a really, really good product for them, which by definition means you're going to exclude others. The TPPN guys have a really good way of describing this exact concept, which is they had like, I don't know, 8,000 listeners and a conversation. They got acquired for hundreds of millions of dollars, just like what's going on there? And the way they pitch it is, if we have millions of people listening to this thing, we've done something wrong. This is specifically designed for the people in power of tech to influence them, to teach them what's going on, and it worked out. It worked out great for them. So it's exactly what you're describing. Okay, I'm going to take us now to fail corner. So people like you come on this podcast, they're like, "Okay, I'll get all these wonderful things." He's done and he's just killing it all the time. Everything's working. In reality, I'm sure not everything has worked in the course of your career. What's one example where things didn't work out and what did you learn from that experience? Oh my God, it's such a weird ... I don't think about win versus fail. I feel like every day I fail a lot. What are big ones that annoy me? Culturally, I think in running teams, I think a mistake that I made is at some point because hiring ... Now, it's easy, but at the time hiring designers that can code was quite challenging. And so then if you loosen that requirement, I did not predict how quickly that becomes like a slippery slope. And I would rather have had fewer designers that are more polymath. So I think that's one on organizational side. On product, oh my God, I mean GitHub Actions and they're the ... I don't know, it's very technical, but the fact that we also thought we didn't need good package management for the actions. I don't know. I think the world would be better off if we had thought about that slightly harder. This is maybe like I started a competitor to Notion in 2014 and I didn't think of it as ... In fact, it wasn't a competitor of Notion because the week that we were going to get a term sheet from True Ventures, Notion pivoted from website building to document collaboration. And so True Ventures was like, "Hey, sorry, we have a conflict." And we're like, "Yep, no worries." And we spent so much time polishing the editing experience. We did markdown folding, all the stuff that you now have in Obsidian, we did that back in 2014, and we thought that's the thing that really matters. And then Notion, by comparison, the first version of the Notion editor was terrible. It was all blocks. You couldn't even select between two blocks, but it turns out it didn't matter. And so I think that is just working diligently on the wrong thing for way too long, huge fail.…

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