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Ep 28: How Founders Close Rounds on Play Money

Cheryl Kellond + Andy Walsh

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Latest episode · Episode 26

The Riskiest Check Is the One You Never Write

23 Oct 2026 · 18 min

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…

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Live on Fridays

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45 minutes, podcast and AMA

We book shows a few weeks ahead. The next ones will be here as soon as they're booked.

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New to the show?

Start with these 5

Listen in this order and you'll have the basics for your first check.

( 87 minutes, start to finish )

  1. 115 minWhy Angels Aren’t Small VCs (And Why That Matters)Angel investing isn’t complicated. We’ve just made it feel that way. In Ep#13 of Angels Decoded , Cheryl Kellond and Andy Walsh unpack one…Episode 13 · 8 May 2026
  2. 217 minWhy 30 is the Magic Number for Angel Portfolios.There is no such thing as an "expert" angel investor. If you believe a single large return makes you an expert, you’re treating angel…Episode 2 · 20 Feb 2026
  3. 321 minSAFE Notes — Simple, Fast… and FuzzySAFE notes are meant to make early-stage fundraising easy. And they do. But most founders and angels don’t fully understand what they’re…Episode 6 · 20 Mar 2026
  4. 418 minWhy SPVs are the "Professional Grade" Way to Angel Invest.There is no such thing as a "simple" direct investment. If you think being directly on a startup’s cap table is a badge of honor, you’re…Episode 3 · 27 Feb 2026
  5. 516 minWhy Your Angel Thesis Shouldn’t Exist YetMost new angel investors think they need a polished investment thesis before writing their first check. In Ep#15 of Angels Decoded, Cheryl…Episode 15 · 22 May 2026
Your hosts

Cheryl Kellond and Andy Walsh

  • Cheryl KellondCheryl Kellond

    Founder and CEO, Play Money

  • Andy WalshAndy Walsh

    Co-host and producer

Every episode

26 episodes, newest first

( about 8 hours in all )

  1. 26The Riskiest Check Is the One You Never Write23 Oct 2026 · 18 min18 min
  2. 25The Ultimate Play Money: Why Your DAF Should Be Angel Investing16 Oct 2026 · 38 min38 min
  3. 24The Affogato Effect — Why CPG Is Angel Investing's On-Ramp11 Sept 2026 · 13 min13 min
  4. 23The Posse Model — Why One Angel's Gut Isn't Enough28 Aug 2026 · 41 min41 min
  5. 22The Angels Who Diligence Too Much Get the Worst Deals31 Jul 2026 · 15 min15 min
  6. 21Angels, The Power Law Is Lying to You17 Jul 2026 · 16 min16 min
  7. 20The Three Deadly Sins of Angel Investing10 Jul 2026 · 17 min17 min
  8. 19The Best Deals Are Already in Your Backyard.26 Jun 2026 · 19 min19 min
  9. 18Dilution Isn't the Problem. Not Understanding It Is.19 Jun 2026 · 17 min17 min
  10. 17Revenue Lies, AI Tricks, and What Angels Should Actually Ask5 Jun 2026 · 18 min18 min
  11. 16Why Angel Money is the Best Capital a Founder Ever Takes29 May 2026 · 15 min15 min
  12. 15Why Your Angel Thesis Shouldn’t Exist Yet22 May 2026 · 16 min16 min
  13. 14How Hidden Capital Unlocks Angel Investing15 May 2026 · 21 min21 min
  14. 13Why Angels Aren’t Small VCs (And Why That Matters)8 May 2026 · 15 min15 min
  15. 12The Angel Advantage in Venture Capital’s “Black Hole"1 May 2026 · 20 min20 min
  16. 11The New Founder Playbook in the Age of AI24 Apr 2026 · 15 min15 min
  17. 10The Echo Chamber Problem in Venture Capital17 Apr 2026 · 19 min19 min
  18. 9Building Your Own AI Investment Framework9 Apr 2026 · 15 min15 min
  19. 8The Emotional Cost of Optimism in Angel Investing3 Apr 2026 · 19 min19 min
  20. 7Convertible Notes — Complex, Costly, and Mostly Unnecessary27 Mar 2026 · 17 min17 min
  21. 6SAFE Notes — Simple, Fast… and Fuzzy20 Mar 2026 · 21 min21 min
  22. 5Small Checks, Big Impact — The Real Math of Angel Investing13 Mar 2026 · 18 min18 min
  23. 4The Truth About Cap Tables and Angel Investing6 Mar 2026 · 19 min19 min
  24. 3Why SPVs are the "Professional Grade" Way to Angel Invest.27 Feb 2026 · 18 min18 min
  25. 2Why 30 is the Magic Number for Angel Portfolios.20 Feb 2026 · 17 min17 min
  26. 1Beyond the Check: Turning Angel Capital into Strategic Leverage.13 Feb 2026 · 22 min22 min
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