Matthew Prince (Co-founder & CEO of Cloudflare)

**Matthew Prince** (0:00)
Curiosity is the opposite of focus. The biggest criticism of Clouflare is, we're a mile wide and an inch deep, and it's so much fun. I love that. Can we make it super inexpensive to run thousands of experiments? We have a traditional product engineering team, but we also have a less traditional thing we call ETI. And their stated goal is to fail 90 percent of the time, with 90 percent of the products that they launch. They don't meet that goal, they fail only 50 percent of the time, and I get mad at them, because I'm like, you're not taking risks. And there are plenty of people inside of Clouflare who are like, we should focus more. And I'm like, that's a great way to build a nice billion dollar company. But if you want to build the next iconic technology company, you really do have to just keep taking on new things and just being okay. It's got to be lots and lots and lots of small bets, but if they're successful, they can have big impacts. How do you take a small team and say, go build a new developer platform? And that's now turned into what will be a multi-billion dollar line of business for us.

**Nick Grossman** (1:36)
Welcome back to The Slow Hunch. In this episode, I am thrilled to welcome my old friend Matthew Prince, the CEO and co-founder of Cloudflare. Cloudflare is among the most important companies on the internet, processing large portions of internet traffic. We got to know Matthew from when we invested at USV back in 2013 at their Series C, and have followed the journey for a long time. In this episode, we go all the way back to the kernels of Matthew's ideas that would later lead to Cloudflare. We spent a lot of time at the end talking about what's going on today on the internet, the relationship between internet content and AI, and what's happening with the business model of the internet, as we move from a search-based internet economy to an answer-based internet economy. So I really hope you enjoy the conversation with Matthew Prince from Cloudflare. I don't know if you remember this, but I was in your office pre-IPO for one of the Cloudflare board meetings where you guys were doing a prep, a mock earnings call. And I thought that was so cool. It's actually the only time I've ever sat through that in a private company getting ready to go public. That was really cool.

**Matthew Prince** (2:46)
It was only because when Fidelity did our fourth round of funding, we pushed them on like, we want you to treat us like a public company, what would you do? And they're like, okay, you want me to be a public company? You should do actual earnings calls, scripted, give guidance, do the whole thing. And at first view, we were so bad.
But by the time we did our real earnings call, I think it was our 13th at that point. So it had been over basically three years.

**Nick Grossman** (3:24)
And I think there was the idea of having some analysts throw in some softball and also hardball questions.

**Matthew Prince** (3:31)
That was the hardest thing we couldn't find because the VCs is that we live in a jurisdiction that doesn't have no fault divorce.
So as a result, nobody tells each other the truth. But nobody wants to offend each other because it's like the pain of getting divorced is too high. So we had a very hard time finding people who ask hard questions.

**Nick Grossman** (3:57)
I remember that. First time I met you was, I think 2012 or 2013, when you guys were raising the Series A, or Series C rather, and I remember walking out of your office with our team, thinking to myself, holy shit, what these guys are building is incredible, so powerful, and also so scary. I hope we trust these guys to handle it the right way.

**Matthew Prince** (4:22)
Very scary. We're very, very scary. I think we've handled it pretty well, mostly.

**Nick Grossman** (4:28)
I think you have too, and so I know you're on the podcast circuit talking about Cloudflare and your story, and I'll give you the setup for what The Slow Hunch is, and maybe we can cover some new ground or maybe look at it in a slightly different way.

**Matthew Prince** (4:48)
I was trying to think about it because I've been thinking about it to some extent, like what My Slow Hunch has been, and I'm not sure to build a better Internet. I haven't got this pithy, but let me try it with you, which is the thing that extends back before Cloudflare, that extends back before Unspam, was something around the idea that the Internet is a bigger deal than people realize, and it's deeply flawed and needs to be fixed.