Michael Seibel - Startup Investor School Day 2

TL;DR

Michael Seibel frames angel investing as a high-risk activity akin to charity, where most investments fail but rare big wins can be life-changing. He advises writing checks large enough to matter at a billion-dollar exit, creating a system to invest within hours or days, and following the "FOMO/friend rule" to invest in friends' startups.

Key insights

• Most angel investments fail; a typical investor should expect a very low hit rate even with rigorous analysis.
• Writing a $25k check is often too small to yield a meaningful return from a billion-dollar exit after dilution and taxes; Seibel moved from $25k to $50k to $100k checks.
• The ability to move quickly (hear a pitch, sign paperwork, wire money) is a core differentiator between A-grade and lesser investors.