Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072

If you go and you watch the Tech Crunch pitch, there's a judge at the end of it. And he asks, "What's your vision?" And I was like, "Our vision is to run the internet." Mic drop.

Matthew, I am so excited for this. I've wanted to do this one for a while. So first, thank you so much for joining me today.

I'm, uh, I'm, I'm happy to be here, although I feel a little bit like a cheap date. Um, you know, I, I get all these... I, I see your posts where you're saying, like, you had to email, you know, Benioff, like, 70 times before he wrote back. You had to... I simply reply to one tweet and the next thing you know, I'm on a podcast. So, I, I, I, uh... anyway, hopefully, hopefully, uh, next time I'm gonna be harder to get.

And you strongly disagreed, Matthew. (laughs)

Yes. (laughs)

Which is a much better way to start a podcast though. I think it's fantastic. Before we get into the, um, debate, let's call it, um, take me back to when you were a child, Matthew. What did you want to be when you were growing up?

A magician, I think. Um-

Why?

You know, I don't know. Both my parents were, um, were... Uh, they, this isn't how they would have described themselves, but they were both entrepreneurs and both bootstrapped entrepreneurs. They, they weren't, they weren't going and talking to people like you, they were, you know, building, you know, small businesses and had a lot of, um, both, uh, you know, success, um, but, but also a lot of failure along the way. I think as a result, uh, I didn't really ever know how to app-... I didn't know how to do anything else, like I didn't know how to apply for a job. I just assumed that, you know, kind of what you did, uh, when you were an adult was you started, started businesses, most of which failed, but some of, sometimes they occasionally worked and you hopefully made enough money to, to put food on, on the, on the table for your family, which is what my, my parents were, uh, again, you know, uh, nice enough to, to be able to do for, for me and my, my, my family.

How did you first make money? I ask this of every founder that I meet on the investing side. I think it's very indicative of one's mindset.

I, I mean, uh, the first thing that comes to mind, and I don't know if they're something earlier was, you know, in about fourth grade or so, um, I, uh, I, I, I, I had access to a bunch of illegal fireworks, and I would sell them at school, which was... it made me really popular with the other kids, but not so popular with their parents. Um, and, and so I think that that, that... probably something around that. Um, there, there, there are a bunch of, again, sort of strange little entrepreneurial things that we did, did in, in school. Though, um, again, it was, uh, none of them were necessarily big moneymakers, but that was, uh, that, that was probably, that was probably the first thing that I, I, I charged someone money for.