In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Kevin Diemar, a powerhouse in private aviation and seasoned angel investor, for his second appearance on the show. Kevin shares his fascinating journey into angel investing, starting with an impromptu investment in a men's yoga shorts company that became his greatest success. He reveals how he sources deals, evaluates opportunities, and builds relationships with founders across various industries—from apparel and mobility scooters to water brands and nutritional supplements. Kevin unpacks the importance of founder authenticity, the power of distribution channels, and why he invests in products he'd personally use. This episode is packed with actionable insights for founders seeking investment and entrepreneurs looking to diversify into angel investing.

Episode Chapters:

00:00 Intro: Kevin Diemar Returns to Discuss Angel Investing01:30 How Kevin Got Started: From Shorts Purchase to Series A Investment07:44 Building Deal Flow and Learning from Winners vs. Losers15:26 The Importance of Communication and Financial Discipline22:17 The Liquid Death Investment: Distribution as a Key Factor29:21 Investment Process: From Product Testing to Founder Due Diligence34:16 Return Expectations and Secondary Market Strategy42:19 Sourcing Deals: Being a Hunter in Angel Investing43:13 Lightning Round: Pitch Deck Essentials, Metrics, and Founder Advice

Episode Resources:
Kevin Diemar on LinkedIn: https://www.linkedin.com/in/kevindiemar
Unity Jets: https://unityjets.com/
Vuori Clothing: https://vuoriclothing.com/
Liquid Death Water: https://liquiddeath.com/
Vuori at REI: https://www.rei.com/b/vuori

Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH

Proseer Website: https://proseer.co/
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Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

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