EP107 From Founder to VP: What Changes About Product Judgment at Scale

Now, Matt, we're going to be talking about unpicking some of that founder essence that's been part of your life for so long and rolling that into a big organization.

But before we get into that, Matt, every good founder has some war stories.

So can I ask, what was it about being a founder for so long that kept you interested in that space? And why did you want to be a serial founder over and over again?

Yeah, I do believe in nature over nurture in most cases.

And so I come from multiple generations of self-employed people or people who started their own firms, going back to my great grandfather, literally.

So I didn't have that.

I didn't have that as a goal when I started my professional career.

I actually focused on computer science and design, thinking that I was going to go work for someone.

I actually saw the stress that they had in their lives and said, I don't want that.

I want to just do great work for someone else to start.

And that was my goal.

But then I got that itch, read a bunch of Paul Graham articles back in 2004, this book called Hackers and Painters.

So 22 years ago, it's hard to believe.

I got, I got started thinking through, you know, well, what, what's my, what's my thing, what's my idea.

And a couple ideas gripped me and they were all, I could, I would go to work, but it was all I could think about, you know, it was just one of those things where, um, I couldn't, I couldn't let go of the idea and, um, I became relentless to pursue it.

So I think that was always, that was how I got started.

To answer your question about what kept me going, it's ridiculously hard, as you know.

It is an exercise in, it's actually How much pain can you tolerate in terms of just the stress that you carry? So it's one of those things of you don't climb Mount Everest for fun.

You do it because it's there, as they said.

And so you go through it.

And what kept me going is people talk about burnout a lot.

And when I experienced burnout, I actually wrote an article called When to Quit.

And I found it very difficult to answer that question.

Sometimes people are like, well, when would you know when to quit? I get that from family, from friends, from people who are working jobs elsewhere and having more success for me than me in the short term.

And I really believe that Burnout to me is actually a, it's your brain, your heart, your body's way of telling you that the path you're on is not fruitful or it's not, you know, the gold is no longer at the end of this rainbow.