The Best Deals Are Already in Your Backyard.

The startup map is being redrawn. Not by VCs flying in to write checks, but by founders who never left home. Cheryl Kellond has watched it happen from the inside, and this conversation is a real-time dispatch from the ground.

The big insight here is simple: regional founders aren't disadvantaged anymore. AI has erased the knowledge gap. What they have instead is something money can't replicate: deep domain expertise, local networks, and proximity to the actual problem. That's a competitive moat, not a consolation prize.

We also got into why most VCs are just lazy. Not malicious, not strategic, lazy. The best arbitrage in early-stage investing right now is sitting outside San Francisco and New York, and most institutional capital is too comfortable to go look for it.

Episode outline

• •The new startup map: How AI leveled the playing field for founders building outside major tech hubs
• •What regional actually means: Louisiana, Birmingham, Tulsa: different models, same underlying logic
• •The VC blind spot: Why most institutional capital ignores regional deals, and why that's the arbitrage
• •The Portland problem: What happens when exits don't recycle capital locally
• •The angel opportunity: Why angels, not VCs, are best positioned to capture regional upside
• •Play Money's angle: 60% of investors on the platform aren't from California or New York

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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The views and opinions shared on Startups Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.