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.
S2E15: We Need To Scale Angel Investing — with Cheryl Kellond, Play Money.
Startups Decoded
48 minutes
1 week ago
S2E15: We Need To Scale Angel Investing — with Cheryl Kellond, Play Money.
Startup investing used to be gated, exclusive networks, complex diligence, and full-time fund managers. But what if anyone could build a startup portfolio the same way they’d shop online?In this episode, Cheryl Kellond, serial founder and CEO of Play Money, shares how her platform is democratizing early-stage investing by pairing curated deals from new fund managers with an experience that feels more like shopping than finance. We dive into her journey from launching Bia Sport and Apostrophe (acquired by Centivo) to building Play Money, the new “fantasy league” for startup investing.Expect a candid lesson on why making startup capital more inclusive can reshape who gets funded and who gets to build wealth.Subscribe nowChapters00:00 Introduction to Play Money and Its Mission04:37 The Challenges of Accessing Capital11:21 The Evolution of Early Stage Investing16:59 Understanding the Angel Investment Landscape22:30 The Role of Education in Angel Investing28:20 The Founder Experience on Play Money33:49 Building Trust and Validation in Startups39:27 The Future Vision for Play MoneyCheryl KellondFounder & CEO of Play Money, is a concept-to-launch expert who has driven $750M+ in revenue from healthtech, SaaS, hardware, and media products. She previously founded Apostrophe (Techstars ’17, acquired by Centivo) and Bia Sport (Lemnos ’12), and has launched major products at Adobe, Yahoo, and E*TRADE. Voted Denver’s Most Admired CEO and a 40 Over 40 honoree, she’s passionate about disrupting legacy industries and building founder-friendly ecosystems.Who Should ListenAspiring angel investors who want a smarter, accessible entry pointFounders curious about new funding pathwaysEmerging fund managers building their first LP baseAnyone interested in wealth-building through startups without “full-time VC” complexityMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: 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.
