Garry's refusal to join Palantir was a multi-billion dollar mistake caused by the same error as leaving web programming: working from external signals instead of direct knowledge
Garry recounts turning down Peter Thiel's invitation to join Palantir because he wanted a promotion at Microsoft. Joe Lonsdale and Stephen Cohen, his smartest fraternity brothers, were starting the company, but he ignored this direct signal in favor of chasing status. ✦ AI generated
Garry Tan · a16z Podcast · 2026-08-12 · original ↗
starts at this moment · 7:26
“You were early there. What did it feel like? Why did you do it?”
Peter said, 'I'm so sure this is the right thing for you. Like here's a check for 70 grand.' That was how much I made at Microsoft at the time. And I said, 'Thank you very much, Mr. Thiel, but I might get promoted to level 60 this year.' Which I did. But I think it's... That was like a $2 billion to $4 billion mistake at this point. And I think about it all the time. Like basically, I did the same thing again. It was like the same thing that got me to go work on Windows Mobile instead of just staying on the thing that I knew and loved... I was working backwards from the map instead of looking down at the territory and saying like, oh, well, these are the smartest people I know.
verbatim transcript · starts at 7:26
7:08like Palantir, either because people were nervous about doing things that were too much in the national interest, or because it was was sort of dismissed as a services business. Now, it's clearly one of the most important companies in the world with one of the most compelling CEOs. You were early there. What did it feel like? Why did you do it? >> Yeah. I mean, uh I have a worse story
7:26than that. I have another mistake story. >> Okay. >> Where um uh Joe Lonsdale and Stephen Cohen uh were my fraternity brothers at Stanford, Phi Psi. >> Uh and then I had a job, and they were like interns at Peter Thiel's hedge fund. >> Okay. >> And uh Peter has this thing where you're supposed to like, you know, when you start a thing, you write down on a piece
7:49of paper all the smartest people who you need to go and hire and like get to join you. And so they said, "Oh, both of them were like, oh, let's go get Gary. He's up in Seattle." Like they flew me down to have dinner with him. >> And he said, you know, Peter said, "I'm so sure this is the right thing for you. Like here's a check for 70 grand." That
8:09was how much I made at Microsoft at the time. >> Yeah. >> And I said, "Thank you very much, Mr. Thiel, but I might get promoted to level 60 this year." >> Oh, no. >> Which I did. >> [laughter] >> But I think it's That was like a $2 billion to $4 billion mistake at this point. >> Oh, no. >> And I think about it all the time. Like
8:27basically, I did the same thing again. It was like the same thing that got me to go work on Windows Mobile instead of >> Yeah. >> um just staying on the thing that I knew and loved. >> Yeah. >> Uh it happened again. I was like, well, I don't know, you know, I was working backwards from the map instead of looking down at the territory and saying
8:46like, oh, well, these are the smartest people I know. Like Joe and Stefan were among the smartest people I'd ever met. >> Yeah. >> Um and you know, if not them, like who was I going to, you know, be a co-founder with? Like it just, you know, the universe was saying like this is the thing you need to do. But all I cared about was what was cool, what was hot,
9:06what would a really good investor say? >> Um >> And the thing is like they're like going off of uh a map. >> Yeah. >> And like you can see, you can look down, you can look around, you can like have first principles knowledge of what's going on. >> Yeah. >> Um and you know, what they were doing is like they were going to governments and three-letter agencies. And it was clear
9:28that um the things that really good computer scientists in Palo Alto could do and create >> Yes. >> uh DC did not have access to that. And you know, it's funny how much that thing that they had identified like Peter and Joe and Stefan and later Alex Karp identified. >> Yeah. >> Um that like runs through almost everything that we do in Silicon Valley. It's just like uh the
- ·Thiel offered $70K check to join Palantir
- ·Garry declined—chased Microsoft level 60 promotion
- ·Smartest fraternity brothers were starting the company
- ·Now estimates it as a $2–4B mistake
- ·Previously chose Windows Mobile over web work
- ·Ignored direct signal: smart people he knew
- ·Chased status signals instead
- ·'Working backwards from the map, not the territory'
- ·External signals: promotions, prestige, map
- ·Direct knowledge: people, territory, intuition
- ·Palantir mistake mirrored Windows Mobile call
- ·Signal-trusting cost billions twice