227: Dan Brisse: From Pro Snowboarder to $500M in Real Estate

231: The New Rules of Building a $100M Company with Roger Neel

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 (he calls it the 3 Ds), why most SaaS companies don't need a moat until they're past $10M, what really happens when you sell to a PE firm, and how a regulatory curveball nearly killed his new company Signos right before launch. Key Takeaways with Roger Neel (01:48) Building A $100M Company In The AI Era (04:03) The Origin Story Of Mavenlink (07:01) The Future Of SaaS And Custom Software (09:25) The Three Ds: Demand, Differentiation, Defensibility (17:18) Why He Jumped Into Health Tech (19:26) Finding Your Actual Passion In Business (21:51) How Signos Revolutionized Continuous Glucose Monitoring (27:27) When A Regulatory Shift Breaks Your Model (33:16) Bootstrapping Vs. Raising Capital (38:09) The 13-Year Growth Arc To Exit (41:54) Going Up Market Faster With AI (46:43) Selling To PE: How The Deal Actually Works (48:48) Why Keep Raising Instead Of Selling Earlier (50:24) PE vs. IPO (51:02) Picking The Right PE Firm (58:03) Advice For Raising Capital Today (59:30) AI Tools Entrepreneurs Should Be Using Watch on YouTube: https://youtu.be/ktl53U-LLL0 [https://youtu.be/ktl53U-LLL0] Let's Connect: Website [https://beyondamillion.com/] | Instagram [https://www.instagram.com/beyondamil] | YouTube [https://www.youtube.com/@Beyondamillion] | TikTok [https://www.tiktok.com/@beyondamil] | Twitter [https://twitter.com/BradWeimert] | Facebook [https://www.facebook.com/profile.php?id=100089061999787]

230: The Brutal Truth About Starting a Podcast in 2026 with John Lee Dumas

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 entire empire on one. So what would he do instead? He already tested it. John launched a second show built around a completely different model, and within months it was generating 5-figures a month while dominating a highly specific niche audience. In this episode, he breaks down exactly how he built it, and why he thinks it's the only kind of show worth starting in 2026. Key Takeaways with John Lee Dumas (00:47) Daily Podcasting for 14 Years (02:22) Creating a Great Interview Using AI (04:31) Publishing His Monthly Revenue for Years (07:20) The One Word Most Entrepreneurs Never Learn (10:11) Compare And Despair (12:01) Why Most Podcasts Are Garbage (13:31) Advice for Starting a Podcast 2026 (21:27) How Have His Monetization Channels Changed? (22:39) A $39 Journal Did $453K In 33 Days (24:45) F.O.C.U.S. — His Framework For Everything (27:25) Advantages of Living in Puerto Rico (30:43) What He Learned from the Military (32:50) His #1 Advice For New Entrepreneurs Watch on YouTube: https://youtu.be/6Mqu2jtox9c Let's Connect: Website [https://beyondamillion.com/] | Instagram [https://www.instagram.com/beyondamil] | YouTube [https://www.youtube.com/@Beyondamillion] | TikTok [https://www.tiktok.com/@beyondamil] | Twitter [https://twitter.com/BradWeimert] | Facebook [https://www.facebook.com/profile.php?id=100089061999787]

229: Biking 2,000 Miles in 13 Days to Raise $1 Million with Matt King

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 into a 900-member community without destroying the culture, the investing mistakes he sees over and over again, and why the best operators are usually the people willing to admit they don't have all the answers. Key Takeaways with Matt King (02:11) The Highest-ROI Skill (03:14) Why Balance Is Overrated (06:31) Prioritizing What Matters (08:52) Scaling Without Killing Culture (13:58) Genuine Contribution (19:20) What Great Investors Do Differently (23:48) Managing High-Ego Entrepreneurs (25:48) How Family Offices View Risk (31:23) The Red Flags That Kill Deals (35:33) Riding 2,000 Miles & Raising $1M (49:46) Play Calling for Your Life (52:03) Non-Negotiable Recovery Habits (53:46) Empowering Kids with Core Values (55:37) The Amputee Who Wouldn't Quit (57:18) Advice for New Entrepreneurs Watch on YouTube: https://youtu.be/4T-DXZ-HnSg [https://youtu.be/4T-DXZ-HnSg] Let's Connect: Website [https://beyondamillion.com/] | Instagram [https://www.instagram.com/beyondamil] | YouTube [https://www.youtube.com/@Beyondamillion] | TikTok [https://www.tiktok.com/@beyondamil] | Twitter [https://twitter.com/BradWeimert] | Facebook [https://www.facebook.com/profile.php?id=100089061999787]

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

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 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 [https://youtu.be/879q12wejtw] Let's Connect: Website [https://beyondamillion.com/] | Instagram [https://www.instagram.com/beyondamil] | YouTube [https://www.youtube.com/@Beyondamillion] | TikTok [https://www.tiktok.com/@beyondamil] | Twitter [https://twitter.com/BradWeimert] | Facebook [https://www.facebook.com/profile.php?id=100089061999787]

227: Dan Brisse: From Pro Snowboarder to $500M in Real Estate

Dan Brisse won back-to-back X Games gold medals as one of the most dangerous urban snowboarders on the planet—jumping off parking garages, rooftops, and rails for a living. But while he was at the peak of his career, he was watching his heroes lose their homes, their wives, and their minds. So he did something different. He started investing. In this episode, Dan breaks down how he went from living on peanut butter and jelly sandwiches to co-founding Granite Towers—a real estate company that manages nearly $500M across 3,300+ apartment units. We get into how he protects downside in every deal, why multifamily real estate quietly compounds wealth, and what his exact investing criteria looks like today. We also get into hiring on core values, why urgency is a red flag in any investment, and the one piece of advice he's giving his 13-year-old son about building wealth. Key Takeaways with Dan Brisse (00:00) Intro (02:25) From Gold Medals to $500M AUM (02:41) The Snowboard Lesson That Saves Him Millions (03:40) His Mental Checklist Before a Crazy Jump (06:10) How Risk in Sports Translates to Real Estate (9:15) Why Most Pro Athletes Go Broke (14:19) Why Losing Is the Best Motivator (16:51) The Passive Income Mindset Shift (20:10) From Duplex to Real Estate Empire (24:39) Lessons in Real Estate Investing (35:56) Understanding Cap Rates & NOI (41:43) Criteria for Evaluating Real Estate Deals (49:40) Analyzing Real Estate Submarkets (53:45) What to Look for in a General Partner (58:43) How to Attract A-Players (01:04:47) Business With a Purpose (01:07:12) The #1 Habit Every Pro Athlete Needs (1:08:26) Advice to New Entrepreneurs (1:09:32) Would He Do It All Over Again? Watch on YouTube: https://youtu.be/5E1FQNZDPWM [https://youtu.be/5E1FQNZDPWM] Let's Connect: Website [https://beyondamillion.com/] | Instagram [https://www.instagram.com/beyondamil] | YouTube [https://www.youtube.com/@Beyondamillion] | TikTok [https://www.tiktok.com/@beyondamil] | Twitter [https://twitter.com/BradWeimert] | Facebook [https://www.facebook.com/profile.php?id=100089061999787]