Winning Twice With Austin Cheviron

Austin Cheviron
  • 5.0 (1)
  • Business

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. 1d ago

    S1 EP29 Chanel Hart D'Aprix - What Are You Still Saying Yes To?

    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 Oklahoma to Chapel Hill, politics, traveling to more than 50 countries, acting and television, and eventually a successful career in real estate—and the lessons she's carried through all of it. Austin and Chanel talk about the power of listening and observing, finding something useful even in the difficult parts of your story, why preparation creates opportunities, and why success sometimes requires you to stop saying yes to everything. As the conversation turns toward this season of their lives, they explore the real cost of opportunity, the limited number of summers we get with our kids, making decisions without financial scarcity driving them, and recognizing when the juice simply isn't worth the squeeze. For both of them, the pursuit is becoming less about more and increasingly about clarity, calm, purpose, and using their time for the people and things that actually matter. Winning twice doesn't mean getting everything right. It means knowing where you're trying to go, forgiving yourself when you don't get it right, and continuing to move toward the life you actually want. 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 EP29 Chanel Hart D'Aprix - What Are You Still Saying Yes To?

  2. Sep 27

    S1 EP28 REST WEEK: What If You Have Too Much Time?

    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 smaller things that otherwise get neglected, and uses Rest Week both to recover from the previous run and prepare for the next one. Austin and Randy talk about why having less available time can actually create more focus, what working like it's the day before vacation can teach you about productivity, and why protecting the time on your calendar matters more than creating the perfect Rest Week. They also explore how the same principles can work for someone with a traditional nine-to-five, why Austin protects Fridays and weekends in addition to Rest Week, and how he's built a schedule where his hardest work happens four days a week, three weeks a month. The goal isn't to copy Austin's calendar. It's to ask a different question: What would happen if you stopped filling every available space with work and intentionally created something to work toward, recover into, and look forward to? Rest Week isn't about doing nothing. It's about focusing when it's time to run, pulling back when it's time to recover, and building a rhythm that lets you do both better. 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 EP28 REST WEEK: What If You Have Too Much Time?

  3. Sep 20

    S1 EP27 Julie Chapman - What’s It Really Like Working With Austin?

    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, successes, frustrations, and work that most people never see. Together, they pull back the curtain on what Austin is actually like to work with—his relentless drive, high standards, direct communication, impatience, constant desire to improve, and the quiet time and deep thinking that happen before many of the decisions everyone else sees. Julie shares what she's learned about handling problems, working through change, staying calm when things go wrong, knowing when to push back, and what kind of person thrives working alongside Austin. They also talk candidly about his weaknesses, why relationships and stewardship may be closer to what he's chasing than money or recognition, and why confidence doesn't mean believing you're always right—it means trusting yourself enough to recognize when you're wrong and change direction. Ultimately, this is a conversation about what success actually looks like underneath the hood: thinking before doing, communicating relentlessly, doing the hard work, staying willing to pivot, and surrounding yourself with people who will tell you the truth. 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 EP27 Julie Chapman - What’s It Really Like Working With Austin?

  4. Sep 15

    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?

  5. 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

  6. 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

  7. 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

  8. 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
See All (29)

About

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.

Information