Uncut Interview with Sam Altman on Masters of Scale [Audio]

Hey, how's it going? This is Craig Cannon, and you're listening to Y Combinator's podcast. So today, we have an uncut interview from the Masters of Scale podcast, and in it, Reed Hoffman, the co-founder of LinkedIn, interviews Sam Altman. All right, here we go!

So I'm here with Sam Altman, president of Y Combinator, who is a good friend and has been involved in many scaling things. Let's start with your entrepreneurial journey: what got you into entrepreneurship? How did you start Loopt, and why did you start Loopt?

Yeah, first of all, thank you for having me here. I fell into it accidentally. I went to college to be a computer programmer; I knew that was all I wanted to do. I started college after the dot-com bubble had bust, and so startups were not on anyone's mind. In fact, I remember one of the things I was surprised by as a freshman in college was that I thought people would still be excited about startups, and if you said you were working on a startup, people would sort of laugh at you in a not nice way.

I actually didn't want to work on a startup. I worked my summer after my freshman year in the Stanford CS department as a researcher, and I loved that. Out of that grew a project which eventually developed into Loopt, but it started as just a project that we worked on sort of like after class and at night. It would not have been a startup if it weren't for Y Combinator.

So it kind of got to the point where we had worked on it during the spring quarter, and it was really fun. I'm very ashamed to say that I had been planning to go be an intern at Goldman Sachs that summer; I accepted a job offer. I realized I was having much more fun working on this project with the other two of us, and we all kind of knew who Paul Graham was. We had followed him online, and he posted this thing saying like, "Hey, not excited about your summer job? Come hack on your project, and you can make a startup."

You know, that seemed like it would be more fun than being an investment banker, so we applied to YC and flew out and interviewed and got funded. We actually were the first company ever funded by YC, and that was how I then just kept going.

Is there anything that—even at the very beginning—is there anything from now, having done Loopt and a bunch of things we're going to get into, that if you could call that younger self of yours going into YC, that you would tell yourself to do differently? Like, key things?

Well, I think one general thing that I didn't understand then and learned pretty quickly, but would have saved me quite a bit of heartache, is about how to calibrate risk. I think most people worry way too much about risk. You know, when you're young and you have nothing to lose, it's absolutely the time to take risks. Unfortunately, that's the time that most people are the most risk-averse in their lives. They need to save; they just want to work for a few years, build up savings, and then they're going to start up. They want to do what their parents want, whatever.

I ended up in the right place, but it could have gone either way. I was totally stupidly nervous about the risk. This idea that most things are not nearly as risky as they seem is a powerful one and one that I always try to tell people in that position. You know, you're like a poor college student with no money and no reputation. If you do a startup and fail, you're just two years older with no money, no reputation, and it's fine. It's actually much harder to wait and let your life ramp up and then do it.

So that's one thing. I think another thing is—I don't know, I think I'm super easy to work with today, but I was sort of infamously difficult to work with when I was 18 or 19. I would have put more effort into trying to be better about that.

And what specifically would you have done to be easier to work with?

I think a lot of it is how you set and communicate expectations with others, and also realizing that if you're the founder of the company and you want to work 100 hours a week and be super focused and productive, that's cool. But like most other people you hire, especially as you get bigger...