The Three Deadly Sins of Angel Investing

Cheryl Kellond is back, and this time she’s calling out angel group sins.

Three of them. Hoarding diligence, forcing minimum check sizes, and treating a cap table seat like a status symbol. If you’ve spent more than five minutes around an angel group, you’ve watched at least one of these play out.

The pattern underneath all three is the same, scarcity thinking dressed up as process. Groups that sit on diligence instead of sharing it, groups that force $10K minimums on people who’d rather write ten $1K checks, groups that need a direct cap table seat to feel like they matter. Cheryl’s watched the same founder gain or lose a million dollars in funding, purely based on whether the group backing them chose to open up or lock down.

The fix isn’t complicated. Share your diligence, drop the arbitrary minimums, use an SPV instead of clogging the cap table. Do that, and you’re not just getting a founder funded faster, you’re setting up a better return for yourself too.

Episode outline

• •The three deadly sins: hoarding diligence, forcing big minimum checks, and cap table ego, named and unpacked one by one
• •Sin #1, hoarding diligence: why sharing your diligence can be the difference between a founder raising $200K or pulling in a $1M follow-on check
• •Sin #2, minimum check sizes: the old $10K rule pushing out a newer, busier, more distributed generation of angels
• •Sin #3, cap table obsession: why insisting on a direct seat can actually cost the founder money and momentum
• •The SPV fix: how automated tools make the old excuses about cost and admin obsolete
• •The abundance mindset: what changes for a local ecosystem when the anchor angel group chooses to amplify instead of gatekeep

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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