The Riskiest Check Is the One You Never Write

Cheryl has spent the last few weeks on panels where every mention of startup investing came with a risk warning attached.

Nobody issues that warning when someone writes a $10,000 check at the sports boosters gala or buys a $5,000 handbag, and both of those come with zero financial return.

Her view, backed by math, is that the bigger risk sits on the other side of the decision. When you don’t write the check, the problems you need solved stay unsolved, and the companies built on your taste, expertise and spending make money for someone else.

The episode also takes apart the guy on stage who wrote three big checks, lost them all, and told the room nobody should angel invest. His problem was concentration and check size. Cheryl lays out the sizing math that fixes it, deals with the lock-up myth, and closes with what happens if 10% of people who could angel invest put in $1,000 a month.

Episode outline

• •The double standard: why nobody lectures you on risk at the charity gala or the handbag counter, but everyone does when you look at a startup
• •The four bottom lines: your voice, your return, backing a founder without access to capital, and building an industry nobody funds
• •First check calls the game: a $2,000 bet on a swab test for gynecological cancers, and what the real risk was
• •The three-check guy: why losing big on three bets says more about sizing than about angel investing
• •The sizing math: 7% of assets, 30 bets over five to six years, roughly a $2,000 check for every $1M in assets
• •The lock-up myth: most of your money is already tied up for decades in your retirement accounts
• •The 10% scenario: how $12,000 a year from a fraction of eligible angels would outsize the $30B US early-stage VC market

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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