Winning Twice With Austin Cheviron

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.