Winning Twice With Austin Cheviron

In this episode of Winning Twice, Austin Cheviron sits down with Chandler Bolt for a direct, high-energy conversation about entrepreneurship, risk, and what it really takes to build something meaningful. From the outside, success can look fast—but Chandler pulls back the curtain on years of reinvesting everything, running lean, and making bold decisions without guarantees. The two dive into the realities of scaling a business, the difference between being risky and taking calculated risks, and why most entrepreneurs misunderstand money, profit, and growth. They also explore the power of writing a book—not as a vanity project, but as a strategic tool to create authority, generate leads, and open doors that traditional marketing never could. Along the way, they touch on identity, discipline, and the mindset required to keep taking big swings, even when you’re already “winning.”

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.