Cheryl Kellond made her first angel investment in an at-home fertility startup and watched it get written off to zero. She still says it was worth it, and she built Play Money to make sure more women get the chance to find out for themselves how to start angel investing.

Cheryl is the founder and CEO of Play Money and a serial entrepreneur who has raised more than $20 million in venture capital and led nearly a billion dollars in product revenue. On Getting Rich Together, host Syama Bunten asks Cheryl about the founder who went silent after taking her money, and how that experience shaped an angel investing platform for beginners instead of scaring her off the space entirely.

Cheryl breaks down why startup investing for women has long relied on fragmented deal flow, individual outreach, and warm introductions, and why she built Play Money to make angel investing work more like scrolling than fundraising. She also runs the math on an idea that became a major aha moment for her. If just 20 percent of accredited investors invested $10,000 a year, she says they could move $30 billion in capital and replicate the entire early-stage startup funding ecosystem.

Cheryl also shares how to start angel investing with a check the size of a weekend trip, and why communication between founders and their investors matters long after the check is written. Find a salon near you or grab a seat at the Wealth Catalyst Summit in San Francisco on October 16 at wealthcatalyst.com 

 

Episode Breakdown:

00:00 Meet Cheryl Kellond

02:13 Shy Childhood, Fairfield County, and Early Rebellion

07:39 Single Motherhood, Night Shifts, and University of Chicago

11:14 The MIT Sloan Admissions Story

12:03 Blogging, Building HTML Sites, and the AOL Sale

19:22 California, Marriage, and the Move to Colorado

22:01 Chaos, Growth, and a Career at Yahoo

27:17 The Boardroom Moment That Changed Everything

28:32 Launching a Startup and Learning It the Hard Way

45:50 Her First Angel Investment and What Went Wrong

49:05 How to Start Angel Investing Through Play Money

56:35 The Math Behind Moving Billions in Capital

1:00:46 Fun Money, Costa Rica, and a Final Ask

 

Find more from Syama Bunten:

Your money story may be shaping your financial life more than you realize. After hundreds of conversations with women at all stages of their financial lives, Syama distilled the questions that helped her understand her own patterns into The Money Story Reset, a free guide featuring five guided reflections and personal stories from her journey.

Download The Money Story Reset and begin uncovering the beliefs behind your financial decisions.

 

Attend a Salon near you: wealthcatalyst.com/salons

Instagram: https://www.instagram.com/syama.co/

Join Syama's Substack: https://thewealthcatalystwithsyama.substack.com/

Website: https://wealthcatalyst.com

Download Syama's Free Resources: https://wealthcatalyst.com/resources

Wealth Catalyst Summit: https://wealthcatalyst.com/summits

Speaking: https://syamabunten.com

Big Delta Capital: www.bigdeltacapital.com

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