The Entrepreneur DNA

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. --- In this episode, I sat down with my GOAT, Gary Vaynerchuk, and he did not hold back. Gary broke down his entire empire, from VaynerX and VeeFriends to Vayner Sports and his new TV production company, and explained why he refuses to follow the "just focus on one business" advice so many of us preach. He opened up about building Wine Library into a $50 million business for his dad, walking away at 34 with nothing, and growing VaynerX to roughly $400 million in revenue without a single outside dollar to start. We got tactical on where attention is right now, including TikTok Live, Substack, Facebook, YouTube Shorts, and Snapchat Spotlight, and why he calls this the era of "interest media." Then we went deep: why being a great operator is his biggest vulnerability, why he has no one he goes to for advice, how he runs his companies like a family business, and whether Gary Vee is actually happy. This one is packed with real advice you can use today. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 California. We got into why she thinks too many people are outsourcing their thinking, the gap she saw between hustle culture and the "make a million from the beach" crowd, and what actually separates the women who win from the ones who stall out. We also had a real conversation about sacrifice, about what it costs a mother to go after something bigger, and about how she is adapting a physical business in a challenging 2026 economy. Heather uses AI for systems, never for her voice, and honestly I think that is where the smart operators are landing. If you are a builder who feels wired for more, this one is for you. About Heather: Heather Simpson is a business strategist, community builder, and the founder of Her Connection Hub, a female-focused coworking community in Bellingham, Washington. Simpson began offering monthly Connection Breakfasts in 2018, and they proved to be the catalyst for something much bigger. The events resonated deeply with attendees, who then voiced their desire for a physical coworking space, and so Simpson turned that dream into a reality with Her Connection Hub, which opened to the public in 2021. Before building for entrepreneurs, Heather spent years in real estate helping agents develop their brands and helping launch brokerages. She is also the founder of She Leads Me, a company devoted to supporting women on their individual journeys in their lives, careers, and businesses. She hosts the podcast Shatter This, a show for leaders, founders, and builders who are done outsourcing their thinking and ready to create what actually lasts. Her first book, Shattering Glass, is coming soon. Connect with Heather Simpson: Instagram: https://www.instagram.com/weshatterglass/ Website: https://shatteringglass.com Her Connection Hub: http://herconnectionhub.com Her Connection Hub Instagram: https://www.instagram.com/herconnectionhub/ Shatter This Podcast: https://podcasts.apple.com/us/podcast/shatter-this-with-heather-simpson/id1866931224 Heather's book, Shattering Glass, is coming soon. Stay updated at https://shatteringglass.com About Justin: Justin Colby is the host of The Entrepreneur DNA and The M.O.R.E Show podcasts and a best-selling author. He is a serial entrepreneur and a seasoned real estate investor with over 20 years of experience. Driven by a passion to help entrepreneurs thrive, Justin created the Entrepreneur DNA community to support business owners in building wealth, systems, and long-term freedom. Through his podcasts, books, education platforms, and hands-on mentorship, he continues to help entrepreneurs scale with clarity and confidence. Connect with Justin: Instagram: @thejustincolby YouTube: Justin Colby TikTok: @justincolbytsof LinkedIn: Justin Colby Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 went to Google as a founding engineer on Cloud Spanner, the global database that powers companies like Deutsche Bank and Nintendo, before building Vertex AI and scaling it into Gemini Enterprise. We broke down how AI actually gets built (yes, it is real people writing real code), why Amazon delivery has always been a losing model, why AWS is where the money is, and the difference between knowledge and wisdom in an LLM. Then we got into Hazel AI, the engine she is building underneath the biggest tech consulting firms on the planet, and the honest conversation everyone is avoiding: which jobs AI is going to take, which ones it is going to create, and why the opportunity has never been bigger for the people willing to get uncomfortable and level up. If you want to hear where AI is going from someone who has actually been in the trenches instead of another influencer guessing, this one is for you. About Guest: Sneha Shah is the CEO and co-founder of Hazel AI, an Autonomous AI Modernization OS that powers global system integrators as they take Global 2000 enterprises from cloud native to AI native. Before founding Hazel, Sneha spent nearly two decades building at the largest scale on the planet. She started her career at Amazon straight out of Carnegie Mellon University, where she was part of the team that built same-day delivery and scaled it across ten countries. She then spent almost a decade at Google Cloud as a founding engineer on Cloud Spanner, the globally distributed database used by companies like Deutsche Bank and Nintendo, growing the team from four to hundreds and the product to over 100 million in scale. She went on to build Vertex AI, Google's flagship AI platform, and scale it into Gemini Enterprise. Hazel AI now works with five of the top ten global system integrators and serves over $10 billion in business across retail, manufacturing, and agriculture. Sneha is based in the San Francisco Bay Area. Guest Links and Socials: Website: https://www.gethazel.dev Platform sign-up: https://gethazel.ai LinkedIn: https://www.linkedin.com/in/snehashah/ Contact: [email protected] About Justin: Justin Colby is the host of The Entrepreneur DNA and The M.O.R.E Show podcasts and a best-selling author. He is a serial entrepreneur and a seasoned real estate investor with over 20 years of experience. Driven by a passion to help entrepreneurs thrive, Justin created the Entrepreneur DNA community to support business owners in building wealth, systems, and long-term freedom. Through his podcasts, books, education platforms, and hands-on mentorship, he continues to help entrepreneurs scale with clarity and confidence. Connect with Justin: Instagram: @thejustincolby YouTube: Justin Colby TikTok: @justincolbytsof LinkedIn: Justin Colby Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 business partner that nearly sank everything, to surviving a lawsuit from a sales partner who tried to put him out of business entirely. We get real about why most business partnerships fail and what he'd do differently. Then we dig into the meat of what his agency does today: how AI engines like ChatGPT, Gemini, and Claude decide who to cite, why building your author authority and connecting it to your content is now more important than keyword stuffing, and the exact three-block content format businesses need to use to get found by AI instead of just Google. If you run a business and you're not thinking about how customers are finding you through AI search right now, this conversation is your wake-up call. Guest Bio & Social Links Kevin C. Roy is the Founder and CEO of GreenBanana SEO, an Inc. 5000 (3x) digital marketing and Answer Engine Optimization (AEO) agency based in Beverly, Massachusetts, that he's built over more than 15 years into a pay-for-performance SEO and AI search visibility firm. He's a frequent podcast guest, author, and media commentator on SEO, AI search, and AEO/GEO, with commentary and work featured in Adweek, SiliconANGLE, Inc., Boston 25 News, and Techstrong TV. Website: greenbananaseo.com LinkedIn (personal): linkedin.com/in/kevincharlesroy LinkedIn (company): linkedin.com/company/greenbanana-seo Instagram: instagram.com/greenbananaseo X/Twitter: twitter.com/greenbananaseo Facebook: facebook.com/GreenBananaSEO YouTube: youtube.com/@GreenBananaSEO About Justin: Justin Colby is the host of The Entrepreneur DNA and The M.O.R.E Show podcasts and a best-selling author. He is a serial entrepreneur and a seasoned real estate investor with over 20 years of experience. Driven by a passion to help entrepreneurs thrive, Justin created the Entrepreneur DNA community to support business owners in building wealth, systems, and long-term freedom. Through his podcasts, books, education platforms, and hands-on mentorship, he continues to help entrepreneurs scale with clarity and confidence. Connect with Justin: Instagram: @thejustincolby YouTube: Justin Colby TikTok: @justincolbytsof LinkedIn: Justin Colby Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 they don't even want and end up wanting to burn it down, and how to use your body to tell whether you're in the right lane. She opens up about going through four back-to-back miscarriages while simultaneously doubling her business, and how healing that grief actually expanded her capacity to hold a bigger vision for her life and work. We get into practical tools like the "alter ego" exercise, "trusting the crickets" through the messy middle, and her five-minute energy reset for staying grounded when everything outside of you feels out of control. If you've ever felt like you're doing everything right but still stuck, or like your business is exploding while your personal life is falling apart, this conversation gives you real, practical ways to work through it. About Christina: Christina Deering is a Shaman, Business Intuitive, Keynote Speaker and creator of the Calibration Keys Methodology. She helps visionary entrepreneurs become the known expert in their industry, expand their income and impact and have the time of their lives doing it. Her insights have been featured in Forbes, Entrepreneur, Psychology Today, ABC and FOX, and she’s the host of the top 5% podcast You Unlimited. Join Calibration Keys: http://christinadeering.com/keys 5 Minute Energy Reset: https://christinadeering.com/reset Instagram: https://www.instagram.com/iamchristinadeering/ Podcast (You Unlimited): available on Spotify and Apple Podcasts Website: https://christinadeering.com/ About Justin: Justin Colby is the host of The Entrepreneur DNA and The M.O.R.E Show podcasts and a best-selling author. He is a serial entrepreneur and a seasoned real estate investor with over 20 years of experience. Driven by a passion to help entrepreneurs thrive, Justin created the Entrepreneur DNA community to support business owners in building wealth, systems, and long-term freedom. Through his podcasts, books, education platforms, and hands-on mentorship, he continues to help entrepreneurs scale with clarity and confidence. Connect with Justin: Instagram: @thejustincolby YouTube: Justin Colby TikTok: @justincolbytsof LinkedIn: Justin Colby Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.