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 nowIn 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.Chapters00:00 Introduction to Angel Investing04:18 Katie’s Journey in Finance06:55 The Importance of Diversity in Funding10:04 The Role of Immigrants in Startups12:43 Building Community and Networks15:30 The Value of Collaboration18:23 The Role of Angels vs. VCs21:07 The Importance of Communication23:45 Finding the Right Investors26:45 Using Technology to Connect29:32 Assessing Founders and Their Pitches32:20 The Art of the Pitch Deck35:01 Final Thoughts and ResourcesKatie DunnAn 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.Who Should ListenFounders preparing to raise pre-seed or seed capitalUnderrepresented founders seeking tactical fundraising adviceAngels or new investors looking to sharpen their evaluation processAnyone who wants to understand how trust, clarity, and communication drive funding decisionsMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.comStartups Decoded is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
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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 nowIn 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.Chapters00:00 Introduction to Angel Investing04:18 Katie’s Journey in Finance06:55 The Importance of Diversity in Funding10:04 The Role of Immigrants in Startups12:43 Building Community and Networks15:30 The Value of Collaboration18:23 The Role of Angels vs. VCs21:07 The Importance of Communication23:45 Finding the Right Investors26:45 Using Technology to Connect29:32 Assessing Founders and Their Pitches32:20 The Art of the Pitch Deck35:01 Final Thoughts and ResourcesKatie DunnAn 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.Who Should ListenFounders preparing to raise pre-seed or seed capitalUnderrepresented founders seeking tactical fundraising adviceAngels or new investors looking to sharpen their evaluation processAnyone who wants to understand how trust, clarity, and communication drive funding decisionsMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.comStartups Decoded is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
S2E7: Boards That Raise, How to Turn Advisors into Capital (with Breen Sullivan)
Startups Decoded
44 minutes
2 months ago
S2E7: Boards That Raise, How to Turn Advisors into Capital (with Breen Sullivan)
What if founders could get the right advisor, investor, or board talent exactly when they need it, before they even ask?In this episode, Breen Sullivan (Founder & CEO, The Fourth Effect; longtime startup GC and board leader) lays out how AI is changing founder access: surfacing who you need and when, structuring “fit-for-purpose” advisory and board relationships, and turning connections into outcomes.We unpack why traditional networks leave too many founders behind, how to make boards growth drivers (not just governance), and how smarter, dynamic advisory models can lift retention, capital access, and founder resilience.Chapters00:00 Introduction to Boards and Advisories02:49 The Role of Community in Startups05:33 Understanding Advisory Boards08:12 The Impact of AI on Advisory Boards11:05 Fit for Purpose: Dynamic Advisory Relationships14:03 Navigating Advisor Roles and Responsibilities16:27 The Importance of Early Advisory Engagement19:32 Leveraging Advisors for Fundraising22:15 The Fourth Effect Platform Overview24:58 Connecting Founders with Advisors27:42 The Future of Advisory Boards and Capital RaisingBreen SullivanBreen Sullivan is Founder & CEO of The Fourth Effect and a seasoned startup executive, board member, and former General Counsel across high-growth companies. She focuses on building inclusive, ROI-driven boards and advisory networks that strengthen execution, fundraising, and leadership. She’s a leading voice on board diversity, founder access, and equitable innovation.The Fourth EffectWho Should ListenFounders building advisory benches and early boardsOperators/execs considering advisor or independent director rolesAngels and VCs exploring advisor-investor modelsBuilders designing AI-assisted founder support workflowsMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All AreasListen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.com
Startups Decoded
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 nowIn 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.Chapters00:00 Introduction to Angel Investing04:18 Katie’s Journey in Finance06:55 The Importance of Diversity in Funding10:04 The Role of Immigrants in Startups12:43 Building Community and Networks15:30 The Value of Collaboration18:23 The Role of Angels vs. VCs21:07 The Importance of Communication23:45 Finding the Right Investors26:45 Using Technology to Connect29:32 Assessing Founders and Their Pitches32:20 The Art of the Pitch Deck35:01 Final Thoughts and ResourcesKatie DunnAn 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.Who Should ListenFounders preparing to raise pre-seed or seed capitalUnderrepresented founders seeking tactical fundraising adviceAngels or new investors looking to sharpen their evaluation processAnyone who wants to understand how trust, clarity, and communication drive funding decisionsMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.comStartups Decoded is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
