#29. Angel investing has long felt like an exclusive club—reserved for venture capitalists, founders, or people writing six-figure checks. But what if backing the next generation of startups was far more accessible than most people realize?

This week, Kate sits down with Cheryl Kellond, founder and CEO of PlayMoney, the platform making startup investing more approachable through curated deal flow, education, and technology. Before launching PlayMoney, Cheryl built and exited companies of her own, worked at Kickstarter and AngelList, and spent years on both sides of the fundraising table. As an angel investor in PlayMoney, Kate was especially excited to explore Cheryl's perspective on the future of startup investing, venture capital, and entrepreneurship.

In this conversation, Cheryl shares why angel investing shouldn't be intimidating, how founders should think differently about fundraising, why not every company should raise venture capital, and how AI is changing both company building and investment decision-making. She also shares what she's learned from founding multiple companies, navigating failure, and helping thousands of first-time investors write their first startup checks.

In this episode, we discuss:

Cheryl's journey from founder to angel investor to CEO of PlayMoney
The biggest misconceptions about angel investing and accredited investors
Why writing your first startup check is more accessible than most people think
How PlayMoney is making startup investing easier through curated deal flow and education
Why founders should think beyond traditional venture capital
The concept of "founder-funding fit" and choosing the right capital for your business
Lessons from building and exiting multiple startups across hardware, healthcare, and fintech
What Cheryl looks for when evaluating early-stage founders and companies
How AI is reshaping entrepreneurship, investing, and startup diligence
Why building local startup ecosystems and local capital matters for innovation
Cheryl's perspective on wellness, balance, and designing a life alongside entrepreneurship
Cheryl's Green-ish Goal for anyone looking to begin investing earlier in life