Brainstorming business ideas with a billion-dollar founder
My First Million
Hubspot
4.7 • 2.9K Ratings
🗓️ 10 July 2026
⏱️ 87 minutes
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| 0:00.0 | You don't have a lot of money, but you have access to AI. |
| 0:23.6 | 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 could be what I want to. I put my all in it like no days off. On the road, let's travel. So, all right, you've done everything. |
| 0:37.8 | 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, |
| 0:42.7 | and six months later, you have a new company. And you've done that like eight times, it feels like. |
| 0:49.4 | Do you ever sit still? I'm working on sitting still. My partner, Hillary, we said she's like a tree, |
| 0:53.7 | 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 |
| 0:56.0 | nature of just being this extremely generative, creative guy? Who cares? Why be the tree? Be the bird? |
| 1:01.4 | Well, I think it's good to have a balance. I'm not trying to sit still from a creative |
| 1:07.6 | business work perspective, but in home life, I think it's more, it's good balance. |
| 1:15.7 | You know, I've added like morning practice with breathing and meditation. So I definitely have |
| 1:20.5 | extreme ADD, and so, but I do better when I focus, but they both work really well together. |
| 1:27.1 | You know, my daughter, |
| 1:28.2 | Carmen, has dyslexia and ADD, and we tried Adderall and some of those things, and she liked it |
| 1:35.3 | first, and then I was like, wait, your brain is beautiful the way it is. I don't want to normalize your brain |
| 1:41.2 | and standardize it. Let's figure out what works best for your brain, |
| 1:45.9 | you know? So I'm a little bit like that with myself of just saying, the way I work, |
| 1:51.2 | I call my investment and incubator work play ventures because I love this kind of triangulation |
| 2:00.1 | between workplay and usefulness to the world. |
| 2:03.6 | And that's why this book took so long and was difficult because it took me a long time to find |
| 2:09.6 | the fun kind of narrative and voice for the book. |
| 2:14.6 | One of the cool parts is that you're very transparent about money. And |
| 2:19.3 | that was pretty cool. I think you were in your late 20s or so when you sold Freeloader. |
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