Winning Twice With Austin Cheviron

In the debut episode, Austin Cheviron sits down with his cousin and longtime partner Nate Cheviron for an unfiltered, zero-prep conversation that sets the tone for the entire show. What unfolds is a raw exploration of their shared story: growing up next door in a large Midwest family, learning consistency from a grandmother who fed 30–50 people every Saturday for decades, and carrying those values into careers that took very different paths before ultimately converging.

The conversation moves from real estate success and corporate engineering, to hard lessons around money, welfare, entrepreneurship, and lifestyle creep. Austin and Nate unpack what it really looks like to scale businesses, pivot when necessary, and build systems that allow for performance and presence—whether that’s selling 88 homes a year by referral while working 38 hours a week, or leading teams without being the one doing the transactions.

At the center of the episode is a defining experience: climbing Mount Hood together in a blizzard. That climb becomes a metaphor for entrepreneurship—fear, focus, risk, trust, and the discipline required to move forward when visibility is almost zero. It’s also the moment the two decide to formally partner, launching what would become multiple companies, coaching programs, and national real estate impact.

The episode also introduces the philosophy behind the podcast’s name: Winning Twice—a concept learned from legendary leadership psychologist Dr. Joe Currier—meaning success that shows up not just on paper, but at home, in health, relationships, time, and legacy.

Listeners will hear candid discussions around:

This first episode is not an interview—it’s a real conversation. And it sets the standard for what Winning Twice is all about: honest dialogue, tough love, practical wisdom, and stories from people who are chasing success without sacrificing what matters most.

If you want to win in business and in life, this podcast is for you.