Many new angels think their first check has to be big to matter.

In reality, the opposite is often true. Oversized early bets can limit diversification and reduce the odds of success. The real advantage in angel investing comes from building a portfolio over time.

In Ep#5 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack the psychology and strategy behind check size, portfolio construction, and why writing smaller checks can actually create more impact for both founders and investors.

The data is simple: returns improve once investors reach around 30 investments. That means angel investing isn’t about one big bet. It’s about thoughtful diversification, learning over time, and backing founders in a way that fits your financial reality.

This conversation also explores how SPVs make small checks practical, why angels should check their ego at the door, and how even a $1,500 investment can create meaningful influence when paired with experience and support.

Listen & Watch:

Apple || Spotify || YouTube

The Realities We Break Down

1) The Check Size Myth
Many new angels assume bigger checks equal more value. In reality, writing smaller checks allows investors to build diversified portfolios and learn the ecosystem without overextending early.

2) The 30-Investment Rule
Data from AngelList shows the strongest returns typically appear after 30 investments. Diversification, not conviction, is the statistical edge in early-stage investing.

3) Why SPVs Make Small Checks Work
Small checks don’t need to burden founders. When angels invest through SPVs, founders receive one clean entry on the cap table while investors participate collectively.

4) Impact Beyond Capital
Sometimes the most valuable angels aren’t the ones writing the biggest checks. Experience, introductions, and operational insight can matter far more than the dollar amount invested.

The Big Idea

Angel investing isn’t about writing the biggest check.

It’s about building a portfolio, supporting founders, and deploying capital thoughtfully over time. Small checks, when combined with experience and network, can drive meaningful impact for both startups and the broader innovation ecosystem.

Chapters

00:00 Introduction
00:44 Why investors obsess over check size
04:35 The impact of small checks on founders
07:45 Angel investing and impact
12:04 Diversification and the 30-investment rule
14:57 Starting small and learning the ecosystem
17:30 Why small checks still matter

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: Substack

Web: angelsdecoded.com

Resources

Startups Decoded Podcast: https://startupsdecoded.com

AngelList: https://angel.co