Startup investing used to be gated, exclusive networks, complex diligence, and full-time fund managers. But what if anyone could build a startup portfolio the same way they’d shop online?

In this episode, Cheryl Kellond, serial founder and CEO of Play Money, shares how her platform is democratizing early-stage investing by pairing curated deals from new fund managers with an experience that feels more like shopping than finance.

We dive into her journey from launching Bia Sport and Apostrophe (acquired by Centivo) to building Play Money, the new “fantasy league” for startup investing.

Expect a candid lesson on why making startup capital more inclusive can reshape who gets funded and who gets to build wealth.

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Chapters

00:00 Introduction to Play Money and Its Mission
04:37 The Challenges of Accessing Capital
11:21 The Evolution of Early Stage Investing
16:59 Understanding the Angel Investment Landscape
22:30 The Role of Education in Angel Investing
28:20 The Founder Experience on Play Money
33:49 Building Trust and Validation in Startups
39:27 The Future Vision for Play Money

Cheryl Kellond

Founder & CEO of Play Money, is a concept-to-launch expert who has driven $750M+ in revenue from healthtech, SaaS, hardware, and media products. She previously founded Apostrophe (Techstars ’17, acquired by Centivo) and Bia Sport (Lemnos ’12), and has launched major products at Adobe, Yahoo, and E*TRADE. Voted Denver’s Most Admired CEO and a 40 Over 40 honoree, she’s passionate about disrupting legacy industries and building founder-friendly ecosystems.

Who Should Listen

Aspiring angel investors who want a smarter, accessible entry point
Founders curious about new funding pathways
Emerging fund managers building their first LP base
Anyone interested in wealth-building through startups without “full-time VC” complexity

Music Credit

“Neptuno” – Phondupe (Album: Onykia)

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