228: How Tommy John Became a 9-Figure Underwear Brand with Tom Patterson

228: How Tommy John Became a 9-Figure Underwear Brand with Tom Patterson

May 14, 2026 · 54 min · Episode 228

About this episode

Tom Patterson discusses the journey of building Tommy John into a successful underwear brand and shares insights on marketing, capital raising, and entrepreneurship.

Today, I'm talking with Tom Patterson , founder of Tommy John, the underwear brand that turned a frustrating problem into a 9-figure business. Tom started the company after getting tired of undershirts constantly coming untucked while working in medical sales. What began as a simple fix turned into one of the biggest direct-to-consumer apparel success stories of the last 15 years. In this conversation, we break down how Tommy John bootstrapped its way to over $100M in revenue before taking meaningful outside capital, why Howard Stern and Kevin Hart became game-changing growth channels, and what founders misunderstand about building premium consumer brands today. Tom also shares lessons on raising capital, balancing wholesale with direct-to-consumer, building a company with your spouse, and why experience can actually become a disadvantage in fast-changing markets. Key Takeaways (01:27) Leveraging Howard Stern's Audience (03:08) Pioneering Podcast/Radio Marketing (04:25) Starting Tommy John with $100 and a Sketch (07:27) How Useful is a Patent? (11:12) Evolve and Innovate (13:49) AI's Future In Product Development (15:04) How to Defend Against Knockoffs (18:01) Wholesale Vs DTC…

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