228: How Tommy John Became a 9-Figure Underwear Brand with Tom Patterson
Release Date: 05/14/2026
238: He Built an 8-Figure Software Company AI Still Can’t Replace with Dean Guida
Beyond A Million
Dean Guida started Infragistics at 23 to build UX/UI tools for professional software developers. Thirty-seven years later, the company operates across six countries, its software is used by more than two million developers, and its customers span the entire S&P 500—including Fidelity, Morgan Stanley, Exxon, Intuit, and Bank of America. But AI can now generate functional software in minutes. So what prevents a company like Infragistics from becoming obsolete? I wanted to understand which parts of software AI will commoditize, where lasting competitive moats will still exist, and why Dean...
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237: How to Build Category-Defining Brands in Any Industry with Jim Donnelly
Beyond A Million
Today I’m talking to Jim Donnelly, a founder who has built and scaled businesses across travel, real estate, wellness, and longevity medicine. He built an online travel community with 300,000+ members that later rolled into Travelocity. He developed luxury real estate that still holds Charlotte’s record for price per square foot. He co-founded Restore Hyper Wellness and helped scale it to 225+ locations. Now, he’s building Humanaut Health, a longevity medicine company with $10M-per-clinic potential. But the interesting part isn’t just what Jim has built. It’s how he keeps moving into...
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236: Geoff Woods on Why Most Founders Are Using AI All Wrong
Beyond A Million
Today I’m talking with Geoff Woods, author of The AI-Driven Leader and founder of AI Leadership, about why so many founders are using AI on the wrong problems. Geoff helped drive Jindal Steel & Power’s market cap from $750M to $12B in four years, and one of his points really stuck with me: you don’t get beyond a million because you write great emails. But that’s exactly how a lot of entrepreneurs are using AI right now. Writing emails, cleaning up inboxes, building random agents, and mistaking activity for leverage. That’s the trap. AI can make you feel productive while you point...
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235: Bootstrapping a $100M Supplement Brand with Matt Gallant
Beyond A Million
Today I’m talking to Matt Gallant, co-founder of BioOptimizers, a supplement company generating $10M a month with a larger mission to help people live healthier for longer. Matt started with a simple realization: if he could get great at marketing, he could build a business in almost any category. That belief eventually led him into health, supplements, and BioOptimizers—but not without some hard-earned lessons along the way. We talk about the moment the business nearly fell apart, how Matt thinks about creating maximum customer value, timeless marketing principles, and the question he...
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234: Cameron Herold Shares the Hiring Mistakes Costing Founders Millions
Beyond A Million
Today, Cameron Herold (Founder of COO Alliance) is back on the podcast to talk about one of the biggest reasons companies stop scaling: bad hiring. We get into why impressive resumes can be misleading, how to tell if someone has actually done the work, and the hiring mistakes that quietly cost companies years of progress. Cameron also breaks down why most entrepreneurs are never properly trained to interview, how he thinks about screening for culture, and what founders miss when they rely too heavily on resumes, references, and gut feel. We also talk about the side of entrepreneurship people...
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233: From a 9-Figure Exit to a $10 Billion Data Center with Jason Van Gaal
Beyond A Million
AI isn’t just creating a software boom, it’s creating an infrastructure crisis. As demand for AI explodes, the real bottleneck isn’t chips or models anymore. It’s power, cooling, permitting, and the ability to build data centers fast enough to keep up. Jason Van Gaal has spent more than a decade solving exactly that problem. After building and exiting multiple data center companies — including one of the largest Canadian tech exits of 2019 — Jason is now taking on his biggest project yet: building a $10 billion AI data center campus in Alberta powered by its own energy...
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232: AI, Acquisitions, and the Cost of Scaling a $1B Company with Bill Tyndall
Beyond A Million
Today I’m talking to Bill Tyndall, who helped build Electric AI from an idea into a company approaching a billion-dollar valuation, raised $211M across eight funding rounds, and now serves as CEO of Techvera. Bill has spent his career building companies around automation, IT, cybersecurity, and digital transformation. But his biggest lesson isn’t just about AI. It’s about capacity. We get into why AI is a capacity multiplier—not a magic fix—how companies create artificial bottlenecks inside their own operations, and why clean data, better routing, strong documentation, and faster...
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231: The New Rules of Building a $100M Company with Roger Neel
Beyond A Million
Roger Neel sold his SaaS company at $100M+ ARR, took three hours off, and dove straight into a health tech startup backed by Google Ventures and Dexcom. In this conversation, Roger breaks down the full arc — from founding Mavenlink in the teeth of the 2008 financial crash, to grinding through 13 years of customer base churn, fundraising rounds, and eventually selling to PE. He also shares what he'd do completely differently if he were starting today with AI tools at his disposal to build a 9-figure business. We get into his framework for evaluating whether a business is actually defensible...
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230: The Brutal Truth About Starting a Podcast in 2026 with John Lee Dumas
Beyond A Million
John Lee Dumas has published a podcast episode every single day for 14 years, leading to more than 5,000 episodes of Entrepreneurs on Fire. He records seven interviews in a single day each week, built a multimillion-dollar media business around the show, and put together 12 straight years of $100K+ months in net profit. But when I asked him what he’d do if he were starting a podcast today, he didn’t hesitate. He said he would never launch an interview show. In fact, he called interview podcasts a waste of time for 99% of people making them today. Bold statement from someone who built his...
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229: Biking 2,000 Miles in 13 Days to Raise $1 Million with Matt King
Beyond A Million
Today I’m talking to Matt King, CEO of GoBundance, host of The Matt King Show, and Chief of Staff for a family office managing high-level investments and operators. Matt is about to ride a bike 2,000 miles from Mexico to Canada while giving away $1 million to people in overlooked communities across America. We get into how he thinks about balance, why he believes entrepreneurs should stop chasing net worth and focus more on cash flow, and what he’s learned reviewing financial statements from ultra-high-net-worth investors. We also talk about how GoBundance scaled from a small mastermind...
info_outlineToday, 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 Margins Explained
(21:33) Why Women Became 30% of Sales
(26:26) How Tommy John Financed Growth
(30:47) Kevin Hart’s Unexpected Partnership
(33:08) The Kobe Bryant Deal That Fell Apart
(36:05) Selling A Minority Stake
(38:20) Running A Business With Your Spouse
(42:36) Experience Can Be Your Worst Enemy
(44:38) Handing Off The CEO Role
(46:53) Avoiding The Post-Exit Crisis
(48:24) Lifestyle Businesses Are Changing
(50:23) The Truth About Raising Venture Capital
(52:06) Advice For New Entrepreneurs
Watch on YouTube: https://youtu.be/879q12wejtw
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