The Angels Who Diligence Too Much Get the Worst Deals

Most angels think heavy diligence makes them safer.

Cheryl Kellond says it just makes them slower, and less trusted. She told a founder to skip an angel group's pitch process entirely, because they grill founders for hours before writing checks that barely clear five figures. The math never worked.

Diligence still matters, but it needs to scale with the check size. Cap tables and incorporation checks are hygiene, borrowed trust from whoever vetted the deal before you. What actually matters is reading the founder and reading the market, and even that should run through people you trust, not just your own hours.

Episode outline

• •The over-diligenced deal that never happened: how a founder saved weeks by skipping an angel group's pitch process entirely
• •Hygiene versus real diligence: why cap tables and incorporation checks are borrowed trust, not original work
• •Sizing the ask: why a $5,000 check earns thirty minutes, not three meetings
• •Reading founders, not resumes: what good angels actually dig for in that conversation
• •The adverse selection trap: how bad diligence habits quietly kill an angel's deal flow
• •Trust the network, not just yourself: the proxy model for scaling diligence without burning founders' time

Andy Walsh - https://www.linkedin.com/in/anwalsh/
2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.

Cheryl Kellond - https://www.linkedin.com/in/c2kprofile/
Founder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.

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