Sam Altman on the Paul Graham advice that not enough founders take to heart

One of the things that Paul Graham used to say that I think has never, never became as venerated advice to the degree it should have, is this idea that you should try to be relentlessly resourceful and that surprisingly often if you just keep looking for new attack vectors on a problem in front of you, you can figure it out. And I think this is one of the most important skills in life and it's surprisingly learnable or teachable, whatever you want to say, and it works in almost all scenarios.

Can you give us an example of a time it worked?

I think even just to use the example that you were going on, we needed to figure out how to get a deal done with this mobile operator. And they didn't really work with startups or technology companies in general. And we probably tried 30 different paths into this company. At one point, the key decision maker said, I'm finally going to meet with you because I want you to stop bothering us. It's too many things, but you can just keep doing that until something works. I think most people at kind of like the first ignored email or the first path where you don't find the right person into a company, or at least the second would just stop. And it was probably like, I mean, it was like a life and death thing for our company, so we were very motivated to do it, but it was probably like, yeah, 30 different points of contact. Right, right.

And how do you know when or if to quit? You're 19 years old, you're sending these emails to the chief technology office, some giant company. Your emails keep getting ignored. At what point does it become kind of crazy?

I think there's definitely a balance. You can clearly take it too far and not learn or not adapt or whatever. But I've never figured out the question when I was running YC that startups would always ask is how do I know when to give up on my startup? And I spent a lot of time trying to come up with a here's the rubric for it. I never did. I think all of these things are judgment calls. You can learn them by like very large data sets and trying a lot of times, but it's hard to say, here's like, here's the one recipe that always works, okay?