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My First Million

7 Brutal Questions for a $20B Founder

My First Million

Hubspot

Investing, Entrepreneurship, Business

4.72.9K Ratings

🗓️ 26 December 2025

⏱️ 44 minutes

🧾️ Download transcript

Summary

Get Sam's AI Executive Coach Playbook - his exact system for everything from revenue optimization to life decisions: https://clickhubspot.com/dhn Episode 778: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) talks to Brian Halligan ( https://x.com/bhalligan ) about the highs and lows of building HubSpot.  — Show Notes: (0:00) Are you happy? (2:57) Does it ever stop sucking? (5:18) Do you have imposter syndrome? (6:55) Were the trade offs worth it? (11:53) Is AI a bubble? (14:47) Do you have to be liked? (17:02) What would you do if you had to start over? (29:36) What did you get wrong? — Links: • Marketing Lessons From The Grateful Dead - https://tinyurl.com/ydmyh6f9  — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com  • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano //

Transcript

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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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