Winning Twice With Austin Cheviron

S1 EP11 Nick Krem - AI Is Changing Everything — Here’s What Still Matters

In this episode of Winning Twice, Austin Cheviron sits down with AI entrepreneur and speaker Nick Krem for a real conversation about business, health, discipline, relationships, and the future of AI. Nick shares his journey from working 15-hour days in a real estate call center to becoming a leader in the AI space, while also opening up about the hidden costs of speaking on stages, burnout, rebuilding his health, losing 75 pounds, and learning how to stay grounded while business grows. Together, they dive into why emotional intelligence, human connection, and real-world experience are becoming more valuable than ever in an AI-driven world, and why the people who win in the future won’t just be the most technical — they’ll be the most human. Winning Twice is a podcast about building a life where success shows up in both business and at home. Hosted by Austin Cheviron, the show features real, unfiltered conversations with high performers about money, time, leadership, and legacy—designed to help you win professionally without losing what matters most personally. #WinningTwice #NickKrem #AustinCheviron #ArtificialIntelligence #Entrepreneurship #RealEstate #BusinessPodcast #SelfDevelopment #Leadership #AI https://krem.ai/ [https://krem.ai/] Austincheviron.com [http://Austincheviron.com]

S1 EP10 Melissa Johnson - Why Working Harder Was Making Life Worse

What happens when success stops being about grinding harder and starts becoming about building better systems? In this episode, Austin sits down with Melissa Johnson for a candid conversation about growth, mentorship, and what happens when you stop trying to do everything your own way. Melissa shares her journey from first hearing Austin speak years ago to eventually committing to coaching and rebuilding her life and business from the ground up. Together they unpack lessons on finances, relationships, authentic leadership, creating sustainable systems, and why the things that feel too simple are often the things that create the biggest breakthroughs. They also dive into the hidden cost of hustle culture, why working 24/7 isn’t a badge of honor, and how finding balance creates more impact at home and in business. If you've ever felt overwhelmed, stuck trying to force growth, or wondered whether success can actually feel peaceful, this conversation will challenge the way you think. Winning Twice is a podcast about building a life where success shows up in both business and at home. Hosted by Austin Cheviron, the show features real, unfiltered conversations with high performers about money, time, leadership, and legacy—designed to help you win professionally without losing what matters most personally. Austincheviron.com [http://Austincheviron.com]

S1 EP9 Ken Hirschman - The Seasons of Success: Sacrifice, Growth, and Best Life

In this episode of Winning Twice, Austin sits down with real estate entrepreneur Ken Hirschman for an honest conversation about growth, leadership, sacrifice, and what it really takes to build something meaningful over time. From working 55-hour weeks as an Aldi district manager to building Best Life & Company into an 1,100-deal real estate organization, Ken shares the mindset shifts, risks, and hard seasons that shaped his journey. Together, they unpack the hidden cost of complacency, why sustainable success requires intentional rest, and how culture, relationships, and self-awareness ultimately become the foundation for long-term growth. This episode feels less like an interview and more like two entrepreneurs talking life on the golf course—covering business, family, vision, burnout, and the pursuit of building a life you actually enjoy living. Winning Twice is a podcast about building a life where success shows up in both business and at home. Hosted by Austin Cheviron, the show features real, unfiltered conversations with high performers about money, time, leadership, and legacy—designed to help you win professionally without losing what matters most personally. Austincheviron.com [http://Austincheviron.com]

S1 EP8 The Run-Rest Calendar: Work Less, Win More

In this solo episode of Winning Twice, Austin breaks down the simple but powerful system that transformed his life and business: the Run-Rest Calendar. After decades surrounded by high-performing but burned-out entrepreneurs, he challenges the belief that more work equals more success—and instead shows how intentional recovery is the real competitive advantage. Using the story of the Iditarod race, Austin explains why most people are operating at half capacity without realizing it, and how building structured rest into your schedule can actually double your production while improving your relationships, health, and clarity. This episode is a practical and mindset-shifting guide to winning at a level your competition doesn’t even know exists—by learning when to push and when to pause. Winning Twice is a podcast about building a life where success shows up in both business and at home. Hosted by Austin Cheviron, the show features real, unfiltered conversations with high performers about money, time, leadership, and legacy—designed to help you win professionally without losing what matters most personally. Austincheviron.com [http://Austincheviron.com]

S1 EP7 Jairek Robbins - Winning Without Burning Out: Rethinking Work, Life, and Success

In this powerful episode of Winning Twice, Austin sits down with Jairek Robbins for a wide-ranging conversation on what it really takes to build a life that works—internally and externally. From scrappy early entrepreneurship and learning to “figure it out” under pressure, to scaling businesses, navigating failure, and developing the parts of yourself you’ve been avoiding, Jairek breaks down the mindset and mechanics behind sustainable success. The conversation expands into bigger territory—rethinking how we work, how relationships thrive, and how emerging tools like AI and deeper self-awareness can help us operate in alignment instead of constant friction. This is about more than winning in business—it’s about winning in how you think, live, and show up, so success doesn’t cost you everything else. Winning Twice is a podcast about building a life where success shows up in both business and at home. Hosted by Austin Cheviron, the show features real, unfiltered conversations with high performers about money, time, leadership, and legacy—designed to help you win professionally without losing what matters most personally. Austincheviron.com [http://Austincheviron.com] Executive Office AI — https://www.executiveoffice.ai [https://www.executiveoffice.ai/] PeakHer — https://www.peakher.ai [https://www.peakher.ai]