
Hosted by Brad Weimert · EN

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 | Instagram | YouTube | TikTok | Twitter | Facebook

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 Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

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 Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

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 Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

I'm sitting down with Jonathan Ronzio, who scaled Trainual from an idea to $30M ARR—while building a company known for its culture and still finding time to climb mountains, run marathons, and live a full life outside of work. What stood out to me in this conversation is how intentional he's been about building systems—not just in the business, but in his life. We talk about why most founders document the wrong things early, how structure actually creates freedom, and how AI is completely reshaping how companies build, sell, and operate. We also get into how he thinks about balance versus alignment, what changes (and what doesn't) after raising capital, and why the most defining moments in business are usually the ones you never planned for. If you're trying to scale without becoming consumed by your business, there's a lot here worth paying attention to. Key Takeaways (00:00) Introduction (01:28) Summiting Aconcagua vs Closing a Series B (03:01) What Is Trainual and Why It Exists (03:52) The #1 Thing SaaS Founders Document Too Late (04:59) When to Create Company Core Values? (06:48) Why Structure Actually Creates Freedom (09:57) Which Processes Deserve SOPs? (11:43) How AI Transformed Trainual's Product Roadmap (15:16) Will AI Kill SaaS? His Honest Take (18:49) Figure Out How to Disrupt Your Business (20:38) Agentic AI and the New Outbound Playbook (22:34) The Exact AI Tech Stack His Team Uses (26:05) Data Security in the Age of AI (30:11) $400K in Credit Card Debt for FB Ads (32:27) Balance vs. Alignment (34:31) Why Daymond John Joined the Cap Table (38:05) Cultural Practices That Actually Work (39:48) Project Management & Communication Tools (43:36) How to Define Culture at Scale (46:30) Mountaineering Lessons That Made Him a Better Leader (53:08) Living an Adventurous Life (58:50) Obsessive Compulsive Creative Disorder (59:43) Advice for Founders Torn Between Focus and Exploration Watch on YouTube: https://youtu.be/q17qPXHSEC0 Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

You don't need to create demand if demand is mandated. That's the insight Will Caldwell used to build and sell his company. Will discovered that inside the mortgage industry, banks are legally required to buy flood certificates on every loan. So, he started Snap — a platform that makes it faster and cheaper for banks to do exactly that. Then he partnered with Intercontinental Exchange, the $95 billion company that owns the New York Stock Exchange, plugged into their existing infrastructure, scaled quickly, and eventually sold 51% of the company for 10x. In this episode, we break down how to build within regulated industries, tap into existing demand, and scale without chasing customers. Key Takeaways (00:00) Small Teams Beat Large Companies (01:52) Why "Fat Cats Don't Hunt" (03:13) Starting His First Tech Company (06:09) Knowing When to Shut Down a Business (06:51) Turning a $100 Compliance Headache Into a Startup (09:03) Finding Opportunity in Regulated Industries (16:58) AI Underwriting (21:09) Scaling via Strategic Partnerships (24:00) Selling 45 Banks in One Month (30:56) Selling to Intercontinental Exchange for 10x (32:31) Why He Sold Only 51% of the Company (36:10) Don't Build the Tech Until You Have THIS (37:44) What Post-Exit Life is Like (38:41) What Will is Investing In Right Now (40:00) Advice for Entrepreneurs Starting Today (40:27) Books That Have Shaped His Thinking Watch on YouTube: https://youtu.be/UmihuBdZByU Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

Today I'm talking with Chris Taylor, an entrepreneur who turned a consulting engagement with Nissan into a software company serving half the automotive industry—then sold the business for multiple eight figures without ever raising outside capital. In this conversation, Chris shares how a consulting project with Nissan became the foundation of his company, how that journey ultimately led to an acquisition, and the earn-out lessons every founder should understand before selling their business. We also talk about building culture, why founder communities like YPO and EO can accelerate growth, and how AI is changing the economics of software and services. Key Takeaways with Chris Taylor (00:00) Intro (01:23) Bootstrapping vs Venture Capital (02:17) Is Every Growth Stage Equally Hard? (04:26) Why Founder Communities Change Everything (09:41) Is SaaS Dead in the Age of AI? (12:30) Why Outcome-Based Billing Could Kill SaaS Seats (15:28) How Chris Got Nissan to Fund His Next Startup (23:09) Turning Consulting Into a Scalable Product (33:11) Why Everything in Business Is Negotiable (40:43) The Real Path to Getting Acquired (48:30) Building Culture in an Unconventional Office (59:20) Earn-Out Lessons Every Founder Should Know Watch on YouTube: https://youtu.be/Vca63g-kq7k Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

Today I'm talking to Dan Demsky, who turned the frustration of trying to pack light while traveling into an 8-figure e-commerce business. He discovered that merino wool clothing lets you pack far fewer items for a trip. The problem was, most of the brands were focused on outdoor gear—not something everyday travelers would actually wear. So Dan and his buddies built Unbound Merino, a fully remote apparel brand doing $32M a year. In this episode, you'll hear how they used crowdfunding to validate product-market fit and scale without investors, how tariffs nearly wiped out their business overnight, and what it actually takes to run a fully remote team. Key Takeaways with Dan Demsky (00:00) Starting an Apparel Brand (04:23) Crowdfunding as Product-Market Validation (05:27) Ecommerce's Hardest Problem (06:52) When Tariffs Nearly Killed their Business (13:09) 30% Repeat Buyers in 30 Days (15:29) Using Crowdfunding as a Growth Engine (28:20) Running a Fully Remote Team (39:41) Should You Do Business with Best Friends? (51:17) Advice to New Entrepreneurs Watch on YouTube: Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

Suneet Agarwal got raided by federal marshals in his underwear, lost everything from his cannabis business, sat on the couch breeding bulldogs for two years, and then built the #1 real estate team in California, selling more than $1B in a single year. In this episode we unpack that journey. We dig into the realities of building culture in a commission-based business, why personal brand is the biggest opportunity right now, and how AI-driven content helped Suneet build and sell a high-ticket coaching business. Key Takeaways with Suneet Agarwal (00:00) Intro (01:41) From Hippie Dispensary to Real Business (05:50) The Federal Raid That Took Everything (08:06) Home Invaded With a Gun to His Head (12:12) From Breeding Bulldogs to $1B in a Single Year (17:47) Are Real Estate Agents Overpaid? (22:44) Building Culture With 1099 Contractors (25:01) Leading from the Front (28:12) Are Real Estate Brokerages Dying? (30:22) Will AI Replace Real Estate Agents? (30:28) Launching One Of The First ChatGPT Courses (34:27) Using AI To Scale Content Creation (37:53) Will AI Kill the Coaching Industry? (38:43) Selling a Coaching Company Built on Organic (42:25) Straight To High-Ticket Offers (47:00) The Personal Brand Gold Rush (48:41) 95% AI Content That Doesn't Feel Like Slop (51:22) Advice for New Entrepreneurs Watch on YouTube: https://youtu.be/FfcKI7VQgJQ Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

Opening a night club or restaurant looks fun from the outside, but behind the scenes it's one of the most operationally complex businesses you can start. That's why I was interested in speaking with Jack Zimmermann. After managing a team of over 200 people at XS in Las Vegas during its $100M peak, he returned to Austin to build Nova Hospitality, a portfolio of hospitality concepts including TenTen, Devil May Care, The Well, Mayfair, Neptune Sushi, LZR, and Coffee & Chill Austin. Most founders in this space struggle to make even a single concept work, and somehow Jack's been able to start and scale 7. I wanted to find out how he decides which concepts to launch, how he funds them, and how he manages the risk and pressure that comes with leading hundreds of people. You don't have to be a restaurateur to get value from this one. Let's get into it! Key Takeaways with Jack Zimmermann (00:00) Running A $100M Vegas Nightclub (06:16) Why Clubs Must Constantly Find New Customers (07:00) Running Multiple Hospitality Concepts Successfully (11:02) The Shift In Alcohol Consumption (13:11) Taking Big Swings in Austin (15:07) New Locations vs Brand New Concepts (19:58) Using Partnerships To Expand Faster (22:27) Why Hospitality is So Hard (25:04) Staying Healthy in the Hospitality Industry (26:20) Letting Your Team Put Out the Fires (28:06) Funding Through Strategic Partnerships (31:42) How To Build A Hospitality Concept (36:47) What He Personally Refuses To Delegate (40:50) Leadership Advice That Stuck (41:45) Non-Negotiable Operating Principle (42:55) Where Austin Hospitality Is Headed (47:05) Advice For New Entrepreneurs Watch on YouTube: https://youtu.be/qAsdI6N1vrE Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook