Winning Twice With Austin Cheviron

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.