Your operator strengths might be the very thing holding you back. Gary Vaynerchuk shares a hard financial realization. Gary Vaynerchuk is known for spotting internet trends years before they happen. But even with that foresight, he faced a brutal reality in 2026. Sometimes, the skills that get you to a certain level of business growth are the exact same habits that prevent you from scaling further

Everyone wants to talk about AI, but my guest this week would rather talk about people. Heather Simpson spent years in real estate building brokerages and personal brands for agents before making a hard pivot to build something for women entrepreneurs specifically. Today she runs Her Connection Hub, a coworking and community space in the Pacific Northwest, and she is expanding into Northern Califo

AI is all anyone can talk about right now, but most of us are just getting started with it while the giants have been building it for two decades. In this episode I sat down with Sneha Shah, CEO and co-founder of Hazel AI, who spent nearly 20 years at Amazon and Google as the engineer behind the scenes. She was on the team that built Amazon same-day delivery and scaled it to ten countries, then we

In this episode I sit down with Kevin C. Roy, CEO of GreenBanana SEO, who's spent the last 15 years mastering search engine optimization and is now at the forefront of how AI is completely rewriting the rules of how businesses get found online. Kevin walks me through his wild entrepreneurial journey, from getting laid off and going door to door offering free websites, to bringing on a 50/50 busine

In this episode, I sit down with Christina Deering, energy and intuition coach and host of the You Unlimited podcast, to talk about something I think about constantly: how the energy you bring to your business matters just as much as the strategy. Christina walks us through the difference between wishing for something and actually being aligned with it, why so many business owners build something

In this episode, I sit down with Austin Armstrong, bestselling author of Virality! and founder of Syllaby, to nerd out on everything happening in AI and content right now. We get into how fast AI video and image generation is moving, why it's getting harder to know what's even real online anymore, and what that means for creators and business owners. Austin breaks down his thesis of being a busine

In this episode, I sit down with Ilhiana Rojas, who climbed the corporate ladder to become a senior Fortune 500 executive in just 12 years — often the only woman, and the youngest, in the boardroom. But somewhere along the way, chasing the version of success she thought she was supposed to have, she lost herself so completely that she burned out and fell into deep depression. We talk about what it

Want help turning your story into a book? Book a free call with Chandler's team to map out your book: selfpublishing.com/justin I sat down with my friend Chandler Bolt, who built self-publishing.com into an 8-figure company (north of $80 million in sales) by his early thirties, and we got into exactly how he did it. We talked about the mindset that separated him from guys like me in our twenties,

In this episode, I sit down with Tiffany Ward, founder and CEO of Human Creative, the company behind Certified Human Content, a service that live-monitors the entire writing and creative process to prove a piece of work was made without generative AI. We get into just how much of what we read today (emails, resumes, social captions, even "motivational" posts) is quietly AI-generated, and why that'

Book a free 15-minute consultation at manifesttherapy.com . Nathaniel Cilley is a licensed mental health counselor, psychedelic therapist, and manifestation coach based in New York City, and he's joining our School.kol.com community to help entrepreneurs work through fear and mental roadblocks. In this episode we cover: What Rational Emotive Behavior Therapy (REBT) is and how it differs from CBT W

FREE RESOURCE FROM BRAD SUGARS DM Brad on Instagram @BradleySugars the word "PLAYBOOK" and he'll send you his free business playbook on how to succeed in business. --- In this episode, I sit down with Brad Sugars — the Founder and Chairman of ActionCOACH, the world's #1 business coaching firm with over 1,000 offices in 85 countries — to break down exactly what separates the entrepreneurs who scale

Get your free copy of Allison's book 'Scale or Fail' - https://pinnacleglobalnetwork.com/dna In this episode I sit down with Allison Maslan, founder and CEO of Pinnacle Global Network and Wall Street Journal bestselling author of Scale or Fail, who has personally built ten companies and helped her team mentor over 150,000 founders. We talk about why the business owner is so often the thing standin

Are you ready to stop treating your startup like a side project and start building a scalable business? In this episode, Dr. Michael Burcham shares the hard-earned wisdom of a veteran who has transitioned from a physical therapist to a multi-million dollar private equity investor. We dive deep into the mindset shifts required to go from a day job to a full-time founder, the critical importance of

Get Mauricio's book 'Tackling Toxicity' on Amazon here: https://a.co/d/08uHkZag In this episode I sit down with Mauricio Velasquez, a worldwide conflict resolution and emotional intelligence consultant who has trained in over seventy five countries, from Guantanamo Bay to the White House to professional sports organizations like the MLS. We get into why most people are conflict averse and what hap

In this episode I sit down with Brett Gilliland, founder and CEO of Elite Entrepreneurs, who has spent the last fourteen years helping business owners make the leap from hustler to real CEO. We dig into why so many founders get stuck right before the ten million dollar mark, and why it almost always comes down to control. Brett walks me through the four systems his company teaches to build a busin

What does it really take to walk away from a seventeen-year corporate career and build an $18 million marketing agency in just three years? In this episode, Eric Winegard shares the mindset, discipline, and relentless commitment that helped him go from a troubled childhood and military structure to becoming the CEO of Rare Blue Moon Marketing. We dive into the realities of entrepreneurship, the di

Free consultation / website: www.assetprotectionattorneys.com — Hillel offers to send complimentary copies of his latest books to anyone who mentions The Entrepreneur DNA. In this episode, I sit down with Hillel Presser, a nationally recognized asset protection attorney who's helped protect over $11 billion in client assets and written six books on the subject. We get into why "it's not what you m

I sat down with Ian Watts, a workforce transformation specialist who's spent two decades helping companies fix what most of them get wrong about their people. Ian's story starts on the east side of Detroit, growing up on welfare, and it's what drove him to chase becoming a millionaire by 30 — which he hit almost four years early, right before his first business completely collapsed in 2006. That s

I sat down with Jon Ostenson, a two-time Inc. 5000 founder and the top 1% franchise consultant behind FranBridge Consulting, to break down everything most people get wrong about franchising. We talked about why "non-food franchising" is such an underrated path to business ownership, how to actually evaluate a franchise opportunity instead of just chasing passion, what it really costs and how long

Are you ready to stop treating your startup like a side project and start building a scalable business? In this episode, Dr. Michael Burcham shares the hard-earned wisdom of a veteran who has transitioned from a physical therapist to a multi-million dollar private equity investor. We dive deep into the mindset shifts required to go from a day job to a full-time founder, the critical importance of