7 Brutal Questions for a $20B Founder
My First Million
Hubspot
4.7 • 2.9K Ratings
🗓️ 26 December 2025
⏱️ 44 minutes
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| 0:00.0 | We were constantly like, |
| 0:01.1 | Salesforce is going to crush us tomorrow. |
| 0:03.7 | Did you see their announcement? |
| 0:05.0 | We're dead. |
| 0:06.0 | We said that so many times. |
| 0:08.5 | I feel like I can rule the world. |
| 0:12.2 | I know I could be what I want to. |
| 0:15.2 | I put my all in it like no days on. |
| 0:17.3 | I'm excited to be on your show. |
| 0:19.3 | It's kind of our show, Brian. Yeah, that's true. |
| 0:21.6 | You consider yourself retired? |
| 0:22.6 | I don't think I'll ever retire. |
| 0:24.6 | But you're not the CEO of a company. |
| 0:26.6 | No. |
| 0:27.6 | I have a whole bunch of interesting stuff going on. |
| 0:30.6 | Are you happier in this phase of your life than when you're running a $20 billion |
| 0:35.6 | company? |
| 0:36.6 | Or how about happier compared to when you're running a $10 million company? Where's like your life than when you were running a 20 or 30 billion dollar company or how about happier |
| 0:38.1 | compared to when you're running a 10 million dollar company where's like your levels of happiness |
| 0:42.3 | been because you've founded a company that is now has i don't know five six seven thousand employees |
| 0:47.1 | billions in revenue now you're retired and you're not retired but you're not running a company |
| 0:52.3 | and you're a little bit of a VC and advisor. So tell me about your happiness levels between each one. |
... |
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