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 s...
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 Investing
01:30 How Kevin Got Started: From Shorts Purchase to Series A Investment
07:44 Building Deal Flow and Learning from Winners vs. Losers
15:26 The Importance of Communication and Financial Discipline
22:17 The Liquid Death Investment: Distribution as a Key Factor
29:21 Investment Process: From Product Testing to Founder Due Diligence
34:16 Return Expectations and Secondary Market Strategy
42:19 Sourcing Deals: Being a Hunter in Angel Investing
43:13 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/
Book a Consultation Contact Us: https://proseer.co/contact/
Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/
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.
Check out our three most downloaded episodes:
- Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
- The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling
- Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon
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