Latest episodes
S1 EP30 Making $200K a Year and Still Broke?
Oct 11, 2026 · 21:42What 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
S1 EP29 Chanel Hart D'Aprix - What Are You Still Saying Yes To?
Oct 4, 2026 · 47:52What 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 con
S1 EP28 REST WEEK: What If You Have Too Much Time?
Sep 27, 2026 · 20:58Can 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.
S1 EP27 Julie Chapman - What’s It Really Like Working With Austin?
Sep 20, 2026 · 50:53What 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. F
S1 EP26 Brian Fryer - Are You Building a Business—or Building a Life?
Sep 15, 2026 · 50:31What 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 abou