Things I Wish I'd Known
summary
Startup advice grounded in hard numbers and mistakes: validate the problem before building and avoid falling in love with technology, because earlier product DM Server became a tiny niche; founders went unpaid (one for about five months) and a 2006 cash crunch led to 10–15% layoffs. Legal and company-structure errors cost about $200,000 to fix; missing an option pool before Series A hurt equity. Expect dilution, hire complementary skills, and remember you need more money than you think.
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chapters (27)
- 0:00Introduction
- 1:04An Unexpected Career
- 3:12Memorable Highs
- 9:42My Hopes For This Talk
- 11:05The Cult of the Entrepreneur vs Reality
- 12:56The High Cost of Founding a Startup
- 14:34Be Methodical: Pursue Your Exciting Idea in a Boring Way
- 15:36Identify a Real Problem
- 18:45Validation: Be On the Right Side of History
- 20:54A Balancing Act: Commitment
- 25:54Building Core Team
- 27:00Another Balancing Act For Founders
- 29:52Setting up Company Structure
- 31:46Create a Plan
- 32:58Choose a Funding Strategy
- 35:02You Need More Money than You Think
- 36:26Funding Options
- 37:12Understanding the Investment Game
- 39:25Choose Wisely
- 40:30You Can Afford to Get Things Wrong
- 41:26Legal Details Matter
- 42:59The Big Things We Got Right
- 47:33Why Did We Make These Mistakes?
- 48:27Sample Audit: Me
- 49:38Mistakes We Didn't Make
- 55:39Life After Spring Source
- 56:06Takeaways
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