#49: Angel Money Isn’t ‘Play Money’. It’s a Major Advantage - with Katie Dunn.

Women, BIPOC, and LGBTQIA+ founders still get boxed out of capital, but Katie Dunn has built her angel investing thesis to do the opposite, and she’s doing it with actual reps (29 investments) and serious financial scar tissue (25+ years in banking with $10B financed). Subscribe now In this episode, Katie breaks down what early-stage angels really look for when they say they’re “betting on the founder”, why most cold outreach fails (hint: nobody reads the investor’s thesis), and how underrepresented founders can cut through the noise with clarity, credibility, and a simple story that lands. We also get into the underrated part: investor relationships. Katie explains why your first investors should be your easiest next-round capital, why founders go dark when things get hard (and how that backfires), and how angels often deliver more value than VCs because they actually have time, context, and intent to help. If you’re raising pre-seed/seed, building community, or trying to stop fundraising from eating your soul, this one’s a practical reset. Chapters 00:00 Introduction to Angel Investing 04:18 Katie’s Journey in Finance 06:55 The Importance of Diversity in Funding 10:04 The Role of Immigrants in Startups 12:43 Building Community and Networks 15:30 The Value of Collaboration 18:23 The Role of Angels vs. VCs 21:07 The Importance of Communication 23:45 Finding the Right Investors 26:45 Using Technology to Connect 29:32 Assessing Founders and Their Pitches 32:20 The Art of the Pitch Deck 35:01 Final Thoughts and Resources Katie Dunn An experienced angel investor, board director, and startup advisor investing in underrepresented U.S. founders at the pre-seed and seed stages, primarily in CPG and technology. Through Masthead Strategies, she’s helped founders raise over $30M by combining investor psychology, storytelling, and AI-powered tools. Her portfolio includes Outcast Brands (Blood Monkey Gin, Two Shores Rum), Another Tomorrow, Juliet Wine, WTHN, Forecastr, and Goodword. Katie also serves on the boards of Outcast Brands and the Enthuse Foundation, and advises Fierce Foundry, a femtech venture studio. To receive new posts and support my work, consider becoming a free or paid subscriber.