The biggest mistake I ever made
summary
Starts with three failed startups: raised $10M at 21 then sold after hiring executives, builds the first StubHub prototype from first line of code to launch in six weeks and later launches a retail chain that fails because passion is missing. Founders start Twilio in 2008 to give developers an API for phone and SMS, endure fundraising during Lehman collapse, bootstrap with ~$20–30K from parents, launch November 2008, get immediate paying users and grow from there.
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chapters (11)
- 0:00Introduction at Collision
- 1:03Conviction over testing
- 2:27First startup failure
- 4:12StubHub beginnings
- 5:59Finding the right idea
- 7:25Extreme sports retail mistake
- 9:35Learning from big companies
- 10:58Conviction for Twilio
- 14:37Fundraising in 2008 crash
- 16:02Launching Twilio
- 17:27Why conviction matters
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