Winning Twice With Austin Cheviron

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.