Most new angel investors think they need a polished investment thesis before writing their first check.

In Ep#15 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack why that thinking often keeps people stuck on the sidelines.

The conversation explores one of the biggest misconceptions in angel investing: the idea that you need to think like a venture capitalist before you start. Cheryl explains that most experienced angels didn’t begin with a thesis. Their thesis evolved through the process of investing itself.

From small early bets to discovering what genuinely resonates, the episode dives into how angel investing becomes as much about self-discovery as financial return.

Cheryl shares stories of investments that looked smart on paper but left her emotionally disconnected, alongside others driven by lived experience, personal values, and genuine conviction. The result is a broader conversation about purpose, identity, and the role money plays in shaping the kind of world investors want to help build.

The bigger takeaway: Your angel thesis isn’t something you invent upfront. It’s something you earn through experience.

Listen: Apple | Spotify | YouTube

Subscribe now

Topics covered:

Why new angels get stuck overthinking investment theses
The difference between VC investing and angel investing
How small bets help investors discover conviction
Why lived experience can become a powerful investment lens
The emotional side of startup investing
Building “emotional armor” around investment decisions
How values and identity shape investment choices
Why money should create more than just financial return

Sometimes the smartest way to start investing is simply to start.

Andy Walsh
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
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.

Access All Areas.

Subscribe: angelsdecoded.substack.com

Web: angelsdecoded.com

Startups Decoded Podcast startupsdecoded.com