May 23, 2025

5 Startups That Looked Dumb—Until They Were Worth Billions

5 Startups That Looked Dumb—Until They Were Worth Billions

Episode 710: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk about how to evaluate risk and upside of new ideas.


Show Notes:

(0:00) Bessemer's $140B misjudgment of Shopify

(5:47) Shaan's Anti-portfolio

(15:26) Goal: Avoid Ruin

(21:30) Outlier personalities

(24:51) Underestimating Uber

(32:16) "You can't overinvest in AI"

Links:

Want Sam's Playbook to Uncover Business Opportunities? Get it here: https://clickhubspot.com/bzo

• “How to miss by a mile” - https://tinyurl.com/2rxubfwa

• Leaked OpenAI emails - https://www.techemails.com/p/elon-musk-and-openai


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