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    Home » 7 Brutal Questions for a $20B Founder

    7 Brutal Questions for a $20B Founder

    webmasterBy webmasterDecember 26, 2025 All Videos 2 Mins Read
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    *Get Sam’s AI Executive Coach Playbook – his exact system for everything from revenue optimization to life decisions:* https://clickhubspot.com/kfd

    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 //

    webmaster

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