Episode 32: "The Founder Is Everything" | Super Angel Katie Dunn On Effective Due Diligence, How Relationship-Building Drives Returns, And Why Clarity Is Kindness The Diligent Observer podcast

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Episode 32: "The Founder is Everything" | Super Angel Katie Dunn on Effective Due Diligence, How Relationship-Building Drives Returns, and Why Clarity is Kindness

5M ago 44:02

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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:

Financial models are founder due diligence too - Katie evaluates financial projections not for accuracy but to understand how founders think.
If it’s not a heck yes it’s a heck no - When she can't quickly decide, she defaults to "no." This candid approach respects founder time more than stringing them along.
Angels tend to overvalue their money, undervalue their networks - The real value angels bring isn't capital but connections and expertise. Her 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. She 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 $27M 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

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

Chapters

1. Introduction (00:00:00)

2. The Importance of Small Angel Checks (00:03:19)

3. Developing a Personal Investment Thesis (00:06:41)

4. The Role of Relationships in Angel Investing (00:10:51)

5. Analyzing Financials in Angel Investing (00:23:45)

6. Understanding Founders' Assumptions (00:24:31)

7. Decision-Making Process for Investments (00:27:36)

8. The Importance of Saying No with Grace (00:28:29)

9. Challenges Faced by Underrepresented Founders (00:32:43)

10. Building a Network for Angel Investing (00:40:29)

55 episodes