Winning Twice With Austin Cheviron

S1 EP8 The Run-Rest Calendar: Work Less, Win More

Austin Cheviron — Sat, 02 May 2026 15:54:52 -0700

In this solo episode of Winning Twice, Austin breaks down the simple but powerful system that transformed his life and business: the Run-Rest Calendar. After decades surrounded by high-performing but burned-out entrepreneurs, he challenges the belief that more work equals more success—and instead shows how intentional recovery is the real competitive advantage. Using the story of the Iditarod race, Austin explains why most people are operating at half capacity without realizing it, and how building structured rest into your schedule can actually double your production while improving your relationships, health, and clarity. This episode is a practical and mindset-shifting guide to winning at a level your competition doesn’t even know exists—by learning when to push and when to pause.

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.

Austincheviron.com

S1 EP7 Jairek Robbins - Winning Without Burning Out: Rethinking Work, Life, and Success

Austin Cheviron — Sat, 02 May 2026 15:41:07 -0700

In this powerful episode of Winning Twice, Austin sits down with Jairek Robbins for a wide-ranging conversation on what it really takes to build a life that works—internally and externally. From scrappy early entrepreneurship and learning to “figure it out” under pressure, to scaling businesses, navigating failure, and developing the parts of yourself you’ve been avoiding, Jairek breaks down the mindset and mechanics behind sustainable success. The conversation expands into bigger territory—rethinking how we work, how relationships thrive, and how emerging tools like AI and deeper self-awareness can help us operate in alignment instead of constant friction. This is about more than winning in business—it’s about winning in how you think, live, and show up, so success doesn’t cost you everything else.

Austincheviron.com

Executive Office AI — https://www.executiveoffice.ai

PeakHer — https://www.peakher.ai

S1 EP6 Bob Fisher - Stop Playing Small: How to Build a Life That Wins Twice

Austin Cheviron — Sun, 12 Apr 2026 13:10:37 -0700

In this episode of the Winning Twice Podcast, Austin Cheviron sits down with Bob Fisher to unpack a decade-long journey of growth, discipline, and transformation—from inconsistent habits and reactive living to building a high-performing custom home business and a purpose-driven life. They dive deep into the realities of entrepreneurship, including sacrifice, delayed gratification, and the power of environment, mentorship, and vision. Through honest conversation, they explore what it really takes to go “all in,” the mindset shifts required to trade good for great, and how personal development ultimately fuels business success. This episode is a blueprint for entrepreneurs ready to take ownership of their path, embrace discomfort, and build a life that wins both financially and personally.

Austincheviron.com

S1 EP5 Bernard Shamow - Build It Right or Don’t Build It

Austin Cheviron — Thu, 02 Apr 2026 00:00:00 -0700

In this episode of the Winning Twice Podcast, Austin Cheviron sits down with Bernard Shamow to unpack what it really takes to build something meaningful from the ground up. From a chance connection at a real estate event to launching a high-performing team in just seven months, this conversation dives deep into vision, execution, and the discipline required to scale the right way. Bernard shares how he transitioned from high-level solo production into leadership—focusing not just on numbers, but on building systems, culture, and people.

Together, they break down the realities most entrepreneurs don’t talk about: sacrificing short-term income for long-term growth, making intentional decisions, and surrounding yourself with people who raise your standards. This episode is about more than business—it’s about becoming the kind of person who can sustain success. Because winning isn’t just about deals closed or revenue earned… it’s about winning in life and in business. That’s what it means to win twice.

S1 EP4 PJ Crescenzo - Win at Home. Win in Business. Repeat.

Austin Cheviron — Thu, 26 Mar 2026 19:21:37 -0700

In this powerful episode of the Winning Twice Podcast, Austin Cheviron sits down with client-turned-friend PJ Crescenzo for a real, unfiltered conversation about what it truly means to win in both life and business. From PJ’s rock-bottom past—facing addiction, debt, and near-death experiences—to building a thriving nationwide lending platform, this episode dives deep into the mindset, structure, and faith required to sustain long-term success. Together, they unpack the true meaning of “winning twice,” emphasizing success at home and in business, and introduce PJ’s transformative “Three V’s” framework—Vision, Values, and Vehicle—for building high-level relationships and scaling with intention. This episode is a masterclass in focus, personal responsibility, and growth, reminding listeners that success isn’t about a single victory—it’s about alignment, consistency, and becoming the person who can win again and again.

Austincheviron.com

S1 EP3 Chandler Bolt - Books Build Business

Austin Cheviron — Wed, 18 Mar 2026 20:48:24 -0700

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.”

S1 EP2 Curt Shewell - Risk And Reward

Austin Cheviron — Wed, 18 Mar 2026 20:48:15 -0700

In this episode of Winning Twice, Austin Cheviron sits down with Curt Shewell for a candid and perspective-shifting conversation about money, wealth, and what it really takes to achieve financial freedom. Curt shares his journey from starting with limited resources to building success through disciplined decision-making and strategic growth, breaking down how the right environment, mentorship, and belief system can completely change your trajectory. Together, they unpack the difference between earning money and building wealth, why most people stay stuck trading time for income, and how intentional business and investment strategies can create long-term freedom. The conversation goes beyond tactics, diving into mindset, identity, and the importance of surrounding yourself with people who expand your thinking. Curt also challenges common misconceptions about investing, risk, and success, emphasizing that wealth is less about luck and more about consistent action and aligned decisions over time.

S1 EP1 Nate Cheviron - No Prep. Real Talk.

Austin Cheviron — Wed, 18 Mar 2026 20:45:42 -0700

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:

Authentic decision-making and real conversations
Money, time, and boundary-setting as an entrepreneur
Building businesses that serve life—not consume it
The cost of growth, pivots, and exits
Why clarity beats perfection, and action beats overthinking

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.