Winning Twice With Austin Cheviron

This episode centers on a powerful shift that many entrepreneurs eventually face: moving from chasing success to building a life worth succeeding for. Austin Cheviron sits down with Colorado real estate leader Cory Williams to unpack the lessons that transformed Cory's business, health, faith, marriage, and mindset after years of outward success masked an unsustainable foundation. Together they ex...

What happens when success no longer feels like enough? In this episode of Winning Twice , Austin Cheviron sits down with leadership and performance coach Ryan Woodruff to explore the transition from chasing achievement to building a life of purpose, impact, and legacy. Ryan shares his journey from a 30-year corporate leadership career and executive role to walking away from a high-paying job in se...

Building a successful real estate team isn't about adding more agents—it's about building the right culture, setting uncompromising standards, and creating a business that can thrive without depending on you. In this solo episode of Winning Twice , Austin Cheviron shares the leadership principles that helped him grow one of the nation's top-performing real estate teams while preparing himself to t...

In this episode of Winning Twice , Austin Cheviron sits down with legendary marketer, speaker, and coach Don Hobbs for a conversation that spans four decades of business, personal growth, and reinvention. Don shares what it was like learning directly under Jim Rohn at just 18 years old, working alongside a young Tony Robbins, building Hobbs Herder into one of the most influential marketing compani...

What does it really mean to win in both life and business? In this episode of Winning Twice, Austin Cheviron sits down with business coach and leadership expert Dave McGhee for a conversation packed with hard-earned wisdom from decades of coaching entrepreneurs, team leaders, and service-based business owners. After helping coach more than 4,500 business owners and leading a coaching organization...

What if the secret to achieving more… is actually doing less? In this special Rest Week episode of Winning Twice , Austin Cheviron breaks down one of the most powerful systems behind his ability to lead multiple companies, stay organized, and avoid burnout: Gather & Focus . Most people aren't overwhelmed because they have too much to do. They're overwhelmed because they're carrying around hund...

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, rebuil...

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 reb...

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,...

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 rac...

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...

In this episode of the Winning Twice Podcast , Austin Cheviron sits down with Bob Fisher to unpack a decade-long journey of growth, discipline, and transformation—from inconsistent habits and reactive living to building a high-performing custom home business and a purpose-driven life. They dive deep into the realities of entrepreneurship, including sacrifice, delayed gratification, and the power o...

In this episode of the Winning Twice Podcast , Austin Cheviron sits down with Bernard Shamow to unpack what it really takes to build something meaningful from the ground up. From a chance connection at a real estate event to launching a high-performing team in just seven months, this conversation dives deep into vision, execution, and the discipline required to scale the right way. Bernard shares...

In this powerful episode of the Winning Twice Podcast, Austin Cheviron sits down with client-turned-friend PJ Crescenzo for a real, unfiltered conversation about what it truly means to win in both life and business. From PJ’s rock-bottom past—facing addiction, debt, and near-death experiences—to building a thriving nationwide lending platform, this episode dives deep into the mindset, structure, a...

In this episode of Winning Twice , Austin Cheviron sits down with Chandler Bolt for a direct, high-energy conversation about entrepreneurship, risk, and what it really takes to build something meaningful. From the outside, success can look fast—but Chandler pulls back the curtain on years of reinvesting everything, running lean, and making bold decisions without guarantees. The two dive into the r...

In this episode of Winning Twice , Austin Cheviron sits down with Curt Shewell for a candid and perspective-shifting conversation about money, wealth, and what it really takes to achieve financial freedom. Curt shares his journey from starting with limited resources to building success through disciplined decision-making and strategic growth, breaking down how the right environment, mentorship, an...

In the debut episode, Austin Cheviron sits down with his cousin and longtime partner Nate Cheviron for an unfiltered, zero-prep conversation that sets the tone for the entire show. What unfolds is a raw exploration of their shared story: growing up next door in a large Midwest family, learning consistency from a grandmother who fed 30–50 people every Saturday for decades, and carrying those values...