Brainstorming business ideas with a billion-dollar founder
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How did Mark Pincus describe his early exits and the ‘right body of water’ idea?
You don't have a lot of money, but you have access to AI. Out loud, let's go through this framework. I almost want to turn this to my whiteboards.
Awesome, great. This is like showing us nudes for My First Million.
This is like exactly what we like. I feel like I can rule the world. I know I can be what I want to. I put my all in it like no day is all for me.
So, all right, you've done everything. You built a $10 billion company. You're, I think, a seed investor in Facebook or early investor in Facebook. One thing you haven't done is sitting still. I'm looking at your biography and your timeline. It seems like you start a company, it either sells or fails. And six months later, you have a new company. And you've done that like eight times, it feels like. Do you ever sit still?
I'm working on sitting still. My partner, Hillary, we said she's like a tree and I'm like a hummingbird. And so I'm trying to be more like a redwood tree.
Why is that? Why not just embrace your nature of just being this extremely generative, creative guy? Who cares? Why be the tree? Be the bird.
Well, I think it's good to have a balance. I'm trying to, I'm not trying to sit still from a creative business work perspective, but in home life, I think it's more, it's good balance. You know, I've added like morning practice with breathing and meditation. So I definitely have extreme ADD. And so But I do better when I focus. But they both work really well together. You know, my daughter Carmen has dyslexia and ADD. And we tried Adderall and some of those things. And she liked it first. And then I was like, wait, your brain is beautiful the way it is. I don't want to normalize your brain and standardize it. Let's... figure out what works best for your brain, you know? So I'm a little bit like that with myself, of just saying, the way I work, I call my investment and incubator Work Play Ventures, because I love this kind of triangulation between work play and usefulness to the world.
And that's why this book, took so long and was difficult because it took me a long time to find the fun kind of narrative and voice for the book.
One of the cool parts is that you're very transparent about money. And that was pretty cool. I think you were in your late 20s or so when you sold Freeloader. I think you said you made like $2 or $3 million. You sold it for $38 million. You walked away, I think, with $3 or $5 million. You can correct me if I'm wrong.
Five after taxes.
Five after taxes.
I had to pay short-term gains because it was so fast.
It was like a 10-month or something like that acquisition, which is crazy. And then you wrote a $38,000 check to Facebook. I think you said that that would be worth $6 billion now. How often are you doing the math as to how much that would be worth had you not sold?
Is that part of your morning meditation? You calculate what 9 million shares of Facebook is worth today?
It's amazing. I say in the book that it is so true in this life. Like some of the patterns that I recognize is if you pick the right body of water and you don't have to pick the right boat. But if you pick the wrong body of water, the best boat isn't going to help you. And it's just been so true. And the internet, obviously, was the right body of water. Now it's like the whole thing. You can't even call it a body of water. And AI is like that now. And there's so many instances where I sold something that I was early, and it would have become worth a lot. But even in selling... My first company, Freeloader, you know, we said no to Yahoo. They had, I think, 35 employees. They'd been public like six weeks.
They were worth $800 million. We would have had 5% of the company. I would have had 1.5%. I remember all these numbers for sure. But I wrote on the back of an envelope, like, if I got fired in year one, which deal would be better if I got fired in year two? I knew I'd get fired. And so I just was trying to figure out, well, what point, how long would I have to make it before the Yahoo deal is better? You know, and I thought I'd have to make it at least like two to three years.
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