Winning Twice With Austin Cheviron

Austin Cheviron

What if your most important conversations about your finance, family, and legacy are waiting for you? One conversation can change everything. Join Austin Cheviron in Winning Twice.

  1. 16m ago

    S1 EP26 Brian Fryer - Are You Building a Business—or Building a Life?

    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 never could have planned. Brian shares his journey from being drafted by the San Diego Padres and playing eight years of professional baseball to struggling for years in network marketing, eventually discovering social media and building a business teaching entrepreneurs and network marketers how to grow online. But this conversation goes well beyond business. Austin and Brian talk candidly about intentionally building a business around the life you want, knowing when family comes first and when an opportunity deserves an exception, staying calm when life doesn’t go according to plan, becoming more aware of the decisions you make, and surrounding yourself with people who help you think through difficult moments. They also discuss money, mentorship, masterminds, writing books, continuing to be a student even when you’re the one on stage, and why success eventually gives you the freedom to stop doing things simply for the money. At its core, this is a conversation about defining what winning actually looks like for you—and then building your business, relationships, priorities, and decisions around that life. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com

    S1 EP26 Brian Fryer - Are You Building a Business—or Building a Life?

  2. Sep 6

    S1 EP25 Rest Week

    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 internet on his annual fishing trip to Canada—and shares how he used the time to disconnect, clean up years of digital clutter, and think about what actually deserves space in his life. Then he opens up his calendar for his current Rest Week, from proactive health appointments and family time to golf, organizing 16 terabytes of business files, improving his systems, and preparing for what's next. The goal isn't to create the perfect week or completely stop working. It's to become more empty, more intentional, and more recovered so that when it's time to run again, you're ready. If your life constantly feels urgent, this conversation might change the way you think about slowing down. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com

    S1 EP25 Rest Week

  3. Aug 30

    S1 EP24 Lee Woodward - Talking Teams, Business & What Comes Next

    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 to reconnect from opposite sides of the world. In this episode, Austin and Lee talk about teams, systems, sales, leadership, and building relationships—but there’s another conversation happening underneath it all. Listen to the questions Austin asks, the similarities the two discover, and the way a relatively new relationship begins creating possibilities for the future. Austin has always believed in planting seeds before you know exactly where they’ll lead, and this conversation is a real-time example of what that looks like. Maybe it’s simply two people getting to know each other. Maybe it leads to Austin speaking in Sydney someday. Either way, it starts the same way most worthwhile opportunities do: with a conversation, genuine curiosity, and the willingness to follow up. Connect With Lee Woodward Lee Woodward is an Australian real estate trainer, presenter, producer, and creator of The Complete Salesperson Course, a training system designed to help real estate professionals build more structured, consistent, and repeatable sales businesses. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com

    S1 EP24 Lee Woodward - Talking Teams, Business & What Comes Next

  4. Aug 23

    S1 EP23 Randy Highsmith - The Conversation Behind Winning Twice

    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 stood out, before sharing his own unlikely journey from solving problems and building a training video library to producing major virtual events, livestreams, and conversations with some of the biggest names in the industry. Along the way, they unpack what years of producing and speaking have taught them about communication, authenticity, listening, taking risks, recognizing a need and being willing to fill it—and why the quality of a conversation matters far more than making everything look perfect. The conversation eventually gets to the heart of Winning Twice: real success isn't winning in one category while everything else falls apart. It's the ongoing work of balancing business, finances, family, relationships, personal life, and faith while staying true to the values that made the success worth pursuing in the first place.  Randy also introduces his own podcast, Sweeter After Difficulty, and the philosophy behind “Honest Conversations. Better Lives.”—using honest conversations and better questions to create awareness, discover new options, and learn from the difficulties that shape us. Austin closes by pointing listeners to his own deeply personal appearance on Sweeter After Difficulty, where he and Randy go beyond business and unpack some of the adversity that helped shape the man, coach, father, and entrepreneur Austin is today. Continue the conversation:  Listen to Sweeter After Difficulty  Check out Austin's Sweeter After Difficulty episode, Built, Not Born: Redefining Success with Austin Cheviron. Connect With Randy at RandyHighsmith.com 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com

    S1 EP23 Randy Highsmith - The Conversation Behind Winning Twice

  5. Aug 16

    S1 EP22 Austin Freiburger - The Three Things Every Real Estate Agent Must Learn

    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 a chance conversation led him toward real estate and how getting plugged into Austin's team gave him something many new agents never have: a proven track to follow. They break down the habits that helped him get his business off the ground, including building a database, consistent lead generation, handwritten notes, client follow-up, learning from mistakes, and showing up every day. The conversation also dives into communication and why understanding yourself, understanding others, and knowing when and how to communicate can dramatically change your results. They explore the three roles every real estate agent eventually has to learn to play—CEO, COO, and CFO—and Freiburger explains the financial system he uses to manage commissions across giving, taxes, family, investments, personal expenses, and business expenses. But perhaps the most important conversation comes when they discuss what happens when success becomes comfortable. Freiburger openly admits that his business has plateaued, not because he's failed, but because his priorities have changed. Austin challenges him to think about what the next five years could look like and whether it's possible to grow without sacrificing more time, family, or quality of life. Ultimately, this is a conversation about building a business that serves the life you actually want, and recognizing that the next level may not require working harder—it may require thinking differently, innovating your systems, and being intentional about where you're going. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com

    S1 EP22 Austin Freiburger - The Three Things Every Real Estate Agent Must Learn

  6. Aug 9

    S1 EP21 Russ Laggan - You Don’t Stop Making Mistakes—They Just Get More Expensive

    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 and hanging onto moving trains to climbing Mount Rainier, racing motorcycles, building businesses, and helping others grow. Russ talks about his philosophy of “failing forward faster” and why the people who reach the top aren’t the ones who never fall—they’re the ones who learn how to get back up. He explains why successful people don’t stop making mistakes; they simply start making mistakes with more zeros. The conversation then turns toward money and the difference between income and wealth. Russ explains why making more money doesn’t necessarily solve the fear of not having enough, why net worth matters more to him than a paycheck, and why true financial freedom is ultimately about having the ability to live the life you actually want. Russ also breaks down the five stages of a career: making money, taking control of your time, creating freedom, building a legacy, and ultimately helping others build theirs. But perhaps the biggest lesson comes at the end of the conversation: sometimes the goal isn't to keep changing the recipe. Sometimes, you need to stop fiddling with everything and simply enjoy the life you’ve worked so hard to create. Because winning twice isn't just about getting where you wanted to go. It’s about becoming the kind of person who can appreciate being there. And as Russ puts it: enjoy today. Enjoy the process. Enjoy the thing you're working on. That’s how you live a beautiful life. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com

    S1 EP21 Russ Laggan - You Don’t Stop Making Mistakes—They Just Get More Expensive

  7. Aug 2

    S1 EP20 Why Taking Time Off Makes You More Money

    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 break is coming allows your brain to run harder during the weeks that matter, why entrepreneurs often confuse exhaustion with productivity, and how protecting time away from work can actually increase your capacity to produce. He also talks about the role of ego, the fear of missing opportunities, and the importance of surrendering the idea that everything has to be perfect before you can take a break. From family time and travel to finances, health, and the simple things that never seem to get done, Rest Week is about creating space for the important things—not just the urgent ones. If you're a high performer who feels like you're constantly running but isn't enjoying the journey anymore, this episode offers a different way to think about winning twice: building a successful business without sacrificing the life you're building it for. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com

    S1 EP20 Why Taking Time Off Makes You More Money

  8. Jul 28

    S1 EP19 Jason “Iron Panda” Bussey - Winning Starts Within: Why Money Can't Fix You

    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 relationships often become the greatest return on any investment. Together they explore why human behavior drives business performance, why money only magnifies who you already are, and why leadership begins with fixing the person in the mirror. Jason shares lessons from coaching high-performing entrepreneurs, working with couples rebuilding trust after infidelity, and helping business owners design lives instead of living by default. If you've ever believed that more money, more success, or more achievement would finally make you happy, this conversation may completely change the way you think about winning. Connect with Jason Bussey • Therapy Practice: https://capstoneatlanta.com • Coaching & Business Development: https://iamironpanda.com • Text Jason directly: 404-594-0625 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com

    S1 EP19 Jason “Iron Panda” Bussey - Winning Starts Within: Why Money Can't Fix You
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What if your most important conversations about your finance, family, and legacy are waiting for you? One conversation can change everything. Join Austin Cheviron in Winning Twice.

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