Winning Twice With Austin Cheviron

What if the secret to building a successful real estate business isn't getting better at closing deals, but getting better at building relationships? In this episode of Winning Twice , Austin Cheviron sits down with real estate coach, entrepreneur, and investor Ricky Carruth for a conversation about building a business that creates financial success without sacrificing the rest of your life. Ricky...

What happens when you finally reach the income you thought would change your life, but you're still broke? In this episode of Winning Twice , Austin Cheviron takes on a financial problem he sees regularly among entrepreneurs and real estate professionals: making more money without actually building wealth. Inspired by an email that generated a 63% open rate, Austin breaks down five reasons someone...

What becomes possible when you get clear enough about the life you want to start saying no to the things that don't belong in it? In this episode of Winning Twice , Austin Cheviron sits down with longtime friend Chanel Hart D'Aprix for a wide-ranging conversation about curiosity, success, family, money, purpose, and learning to trust yourself. Chanel shares a journey that has taken her from Oklaho...

Can you really get four weeks of work done in three—and actually create more room for your life? In this Rest Week episode of Winning Twice , Austin Cheviron brings producer Randy Highsmith into the conversation to unpack how Rest Week actually works. Rather than simply taking a week off, Austin explains how he deliberately moves the “big rocks” into three focused run weeks, protects space for the...

What does it really look like behind the scenes of Winning Twice ? In this episode, Austin Cheviron turns the questions over to someone who has had a front-row seat to his life and businesses for the last decade: his executive assistant, Julie Chapman. From Austin's real estate career and building a team to coaching, training, and multiple businesses, Julie has seen the decisions, pivots, successe...

What happens when two people who have built successful businesses realize they’ve been designing their lives around many of the same principles? In this episode of Winning Twice , Austin Cheviron sits down with new friend Coach Brian Fryer to talk about the unlikely connections that brought them together and why relationships, curiosity, and simply getting in the room can create opportunities you...

If you want to run hard, you have to learn how to rest. In this episode of Winning Twice , Austin Cheviron breaks down a practice he's been refining for nearly a decade: Rest Week. But this isn't a week of doing nothing. It's intentionally creating space for the important things that get crowded out by the urgent ones. Austin walks through his last Rest Week—including an unexpected week without in...

This week on Winning Twice , Austin Cheviron shares a conversation from his appearance on Lee Woodward’s podcast after the two first met while speaking at an event in Birmingham, UK. Lee, an Australian sales trainer and creator of the Complete Salesperson Course, was the day-one keynote while Austin took the stage on day two, and a conversation between the two eventually turned into an opportunity...

In this episode of Winning Twice , Austin Cheviron brings longtime friend and producer Randy Highsmith out from behind the camera for a conversation about how their paths crossed, how the Winning Twice podcast came to life, and the shared ideas that have kept them working together.  Randy takes Austin back to their first meeting at an eXp event, where Austin's relentless curiosity immediately stoo...

What does it actually take to build a successful real estate career from scratch? In this episode of Winning Twice , Austin Cheviron sits down with Austin Freiburger to unpack his six-year journey in real estate—from working two jobs and searching for his next opportunity to building a business through consistency, education, communication, and disciplined financial systems. Freiburger shares how...

What if the mistakes you’re making aren’t really mistakes—but unintended results that are teaching you how to win? In this episode of Winning Twice , Austin Cheviron sits down with Russ Laggan for a fast-moving conversation about failure, fear, money, freedom, legacy, and learning to enjoy the journey along the way. Russ shares stories from a life that has taken him from working on the railroad an...

What if taking time off could actually help you make more money, perform at a higher level, and enjoy your life more? In this episode of the Winning Twice Podcast, Austin Cheviron breaks down the concept of the Rest Week —a dedicated week each month designed to recover, reset, handle the things that get neglected, and come back to work with more energy and focus. Austin explains why knowing a brea...

Most people think success starts with better strategies, more money, or harder work. Jason Bussey believes it starts with becoming a healthier human being. In this episode of Winning Twice , Austin Cheviron sits down with psychotherapist, business consultant, and entrepreneur Jason "Iron Panda" Bussey to unpack the unexpected friendship that began in a mastermind group—and why authentic relationsh...

Austin delivers a practical framework for building long-term financial freedom by focusing on systems instead of income alone. The core message is that wealth isn't created by making more money—it's created by having a clear vision, intentional habits, and a process that directs every dollar before it's ever spent. He walks listeners through the importance of defining a financial vision, tracking...

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...