5 Startups That Looked Dumb—Until They Were Worth Billions

My First Million

Hubspot

Entrepreneurship, Investing, Business

4.8 • 2.7K Ratings

🗓️ 23 May 2025

⏱️ 46 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	The headline here is they made the investment.
0:03.0	So it's not like they passed.
0:04.0	They made the investment and their best case scenario they wrote was $400 million as an exit value.
0:10.0	400 million and now it's $140 billion.
0:12.0	I feel like I can rule the world.
0:15.0	I know I could be what I want to.
0:18.0	I put my all in it like no days off.
0:20.0	Let's travel. Never look at me tell you about something that I've been thinking about.
0:24.3	And I thought it was really cool.
0:25.9	And our friend Sheel just shares the best stuff.
0:29.2	The most interesting man on X?
0:31.3	The most interesting man on X.
0:32.7	The most interesting man I know, actually.
0:34.9	He does a lot of amazing stuff.
0:36.9	But he shared something. So I got to give him credit. But basically, I saw, actually, he does a lot of amazing stuff, but he shared something, but so I got to
0:39.1	give him credit. But basically, I saw this Jeff Bezos quote, and I want to know what you think
0:43.1	about it. And he said something where he said, I think it's generally human nature to overestimate
0:48.6	risk and underestimate opportunity. And then he went on to say, and so I think entrepreneurs in
0:53.6	general would be
0:54.2	well advised to try and biased against that. The risks are probably not as big as you perceive. The
0:59.4	opportunities may be a lot bigger than you perceive. And so the interviewer was like, you seem really
1:04.9	confident. And he goes, well, you call it confidence, but maybe I'm just accepting that human
	...

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