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Founders should pursue what they know and love rather than chasing what's hot — earnestness requires courage to trust your own direct experience over crowd consensus.

Garry Tan recounts leaving web programming for Windows Mobile because it seemed hot, only to miss the social/web boom. He argues the right question isn't 'what's hot?' but 'what do you know uniquely?' ✦ AI generated

Garry Tan · a16z Podcast · 2026-08-12 · original ↗

starts at this moment · 2:36

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maybe talk to me a bit about the beginning of your journey 2003. What did it feel like when you first got in the game back in 2003 coming out of Stanford?

the classic question I'm sure you get that, you know, all investors get all the time is, 'What's hot and what should I work on?' And that's the wrong question to ask. Like the right question is like, 'What are you interested in? What do you know uniquely?'

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2:24>> Yeah, it was smart and you know, I mean this is true now. Um you know, in in front of all these people at Startup School, uh you know, I sort of started this don't LARP >> Right. >> um meme. >> I saw that. >> Uh but I think like that's that's embedded in this idea that like you should just be earnest >> Yeah. >> and then you shouldn't follow what the

2:45crowd is saying, right? Like at that moment people said the web was dead, but that was sort of the perfect time to work on web and social and things like that. Um and you know, I didn't do it. I I ran off and said like "Oh, well, the next hot thing will be mobile." So I wanted to work at Windows Mobile, which was true, but um why I

3:06give up like the thing that could have been the next thing. >> What I love about what you're saying though is often when we hear earnest, we think naive, but actually what it sounds like you're saying is there's like earnestness is a sort of result of maturity and courage. >> Courage is actually I think the right thing. >> Yes. >> Like if you know something that's sort

3:25of if someone just like comes and contradicts you or even if like a blog post or like someone on Twitter uh contradicts you, >> Yeah. >> you're like, well, I I don't I don't agree with that because I believe my own direct experience. >> Yes. >> I know that I'm not a time traveler because if I was a time traveler, I would have I would have sent a message

3:45back to myself and said, "Just stay on working on web stuff." Like you literally have um 5 years of experience on top of everyone else. Like you could do an end run around everyone. Like you could have built like any kind of social software. >> Yes. >> But instead I was, um, you know, I was 22. So I was like being whipped around by, uh, whatever I could read in The

4:06Wall Street Journal. And, you know, I the the classic question I'm sure you get that, you know, all investors get all the time is, "What's hot and what should I work on?" >> Right. >> And that's the wrong question to ask. Like the right question is like, "What are you interested in? What do you know uniquely?" And so I was that's like, you know, one of a great many mistakes I

4:28made in my career. I feel like I'm a little bit, uh, doomed to be the first principle storyteller of, uh, all the mistakes that I made >> Well, I think that it's it's very inspiring for founders to hear your own journey and your own mistakes. And then not feel so bad about the ones that we've all made along the way. >> I mean, maybe talk about the culture of

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