
Hosted by Brad Weimert · EN

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 all that horsepower at work that doesn't actually move the business forward. Geoff walks through what it looks like to flip that: using AI as a strategic thought partner instead of an errand boy, why most leaders are skipping steps they haven't earned yet, and how to think about AI in a way that improves decision-making, focus, and team performance. Geoff also shares what he learned helping scale a multi-billion-dollar company, why letting the right fires burn is part of leadership, and the move his assistant made to rewrite her own job description and 100x her role. If you've been treating AI like a faster Google, this conversation will reframe what it can actually do for you as a founder. Watch on YouTube: https://youtu.be/beMjviX1_B8 Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

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 believes every entrepreneur needs to ask as markets get more crowded and customers become harder to win. Watch on YouTube: Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

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 rarely admit in real time: burnout, loneliness, identity, alcohol, retirement, and what happens when the business stops giving you the same hit it used to. Watch on YouTube: https://youtu.be/SCNzMOVeO48 Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

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 infrastructure. In this episode, we break down the future of AI infrastructure, why data centers are becoming power companies, the realities of scaling massive industrial projects, and what Jason learned from building, exiting, and starting over again. Key Takeaways with Jason Van Gaal From Two Exits to a $10B Swing Hire People Better Than Yourself Cutting Build Time to 120 Days Financing 400% Growth Without Imploding How He Invests After the Exit Why He Came Out of Retirement Why Alberta Won the Build Busting the Data Center Water Myth Noise, Infrasound, and Tinfoil Hats What Happens If Approvals Fail Why He Stays in His Lane Why Scaling Fast Is a Trap Learning Just in Time vs Just in Case Watch on YouTube: https://youtu.be/eRR-PLNkVtQ Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

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 adoption may matter more than simply throwing new tools at the problem. Bill also opens up about the founder side of the journey: what it felt like to take money off the table, why a big exit didn't create the happiness he expected, and how he now thinks about purpose, delegation, acquisitions, identity, and building a healthier company. Key Takeaways with Bill Tyndall (01:55) Business vs. Purpose (03:07) Will AI Kill Managed Service Providers? (04:40) Running a Business Like a Football Team (06:44) The Injury That Ended the NFL Dream (09:21) Why a "Boring" Industry Attracted $211M (14:50) What an MSP Actually Does (Plain English) (19:32) Artificial Capacity Constraints - $17M to $38M in 1 Year (23:22) Building Faster With AI Tools (26:38) Why He Walked Away From a $1 Billion Company (31:09) When Money Doesn't Fix Happiness (37:25) How to Avoid Regret After An Exit (39:17) Effective Delegation (41:55) The Problem with Roll-Ups (46:12) Acquisition Integration Challenges (49:28) The First 120 Days After an Acquisition (51:22) Returning To The CEO Seat (54:38) AI As A Capacity Multiplier (58:11) AI Governance & Control (01:00:10) Advice For Young Entrepreneurs Watch on YouTube: https://youtu.be/oB-X1bAyF80 Let's Connect: Website | Instagram | YouTube | TikTok | Twitter | Facebook

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

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