Insights from a commercial real estate veteran who's now funding underrepresented founders while challenging traditional angel investing assumptions

Today's episode explores three ideas that caught my attention:

1. Financial models are founder due diligence too - Katie evaluates financial projections not for accuracy but to understand how founders think.
2. If it’s not a heck yes it’s a heck no - When Katie can't quickly decide, she defaults to "no." This candid approach respects founder time more than stringing them along.
3. Angels tend to overvalue their money, undervalue their networks - The real value angels bring isn't capital but connections and expertise. Katie's viral LinkedIn post for a founder where she invested just $2,500 exemplifies this misunderstood dynamic.

I explore these ideas and more with Katie Dunn.

Katie Dunn brings over 25 years of commercial real estate finance experience to angel investing, having underwritten more than $10 billion in deals throughout her career. Now focused exclusively on funding underrepresented founders in CPG and technology, she's helped startups raise over $27 million by teaching entrepreneurs how to articulate their vision with clarity and confidence. Her board positions with Outcast Brands, Fierce Foundry, and the Enthuse Foundation further demonstrate her commitment to transforming how capital flows to previously overlooked founders.

During our conversation, Katie shares:

• A framework for identifying the "fast no" in angel investing that respects founder time while maintaining clarity about investment criteria – something angels often struggle to articulate.
• The troubling reality of gender bias in startup funding including shocking examples of inappropriate investor demands that highlight why underrepresented founders face structural disadvantages.
• How founders can structure investor updates to maximize engagement and support, with specific communication best practices to look for.

Connect with Katie

LinkedIn | Website

Stuff We Reference

• Outcast Brands
• LOOP
• Caroline Dell
• LOLA
• CHIEF
• Citrine Angels
• Gaingels

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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.