17 - Kevin Diemar on Angel Investing
5 to 50: Financial Strategies for Growing Companies · 2025-10-07 · 48 min
Episode notes
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.