What if your most important conversations about your finance, family, and legacy are waiting for you? One conversation can change everything. Join Austin Cheviron in Winning Twice.
Winning Twice With Austin Cheviron
Claim This Podcastby Austin Cheviron
16 episodes
Updated Daily
Accepts GuestsHas Sponsors
Podcast Overview
What if your most important conversations about your finance, family, and legacy are waiting for you? One conversation can change everything. Join Austin Cheviron in Winning Twice.
Language
🇺🇲
Publishing Since
3/19/2026
1 verified contact email on file for Winning Twice With Austin Cheviron
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Recent Episodes
June 28, 2026
S1 EP16 Ryan Woodruff - Why High Achievers Burn Out—and What Comes Next
<p>What happens when success no longer feels like enough? In this episode of Winning Twice, Austin Cheviron sits down with leadership and performance coach Ryan Woodruff to explore the transition from chasing achievement to building a life of purpose, impact, and legacy. Ryan shares his journey from a 30-year corporate leadership career and executive role to walking away from a high-paying job in search of something more meaningful. Together, they unpack the realities of burnout, entrepreneurship, coaching, and the difficult process of discovering what you're uniquely equipped to offer the world. Along the way, they discuss why video games taught them lessons about strategy, leadership, optimization, and decision-making, how coaches should identify the one thing they do exceptionally well, and why simplifying your message often leads to greater impact. Whether you're building a business, considering a career pivot, or trying to create a life aligned with your values, this conversation offers practical wisdom on finding conviction, serving others, and ultimately winning twice—both professionally and personally.</p><p><br></p><p><br></p><p><br></p><p>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.</p><p><strong>Subscribe for more conversations on leadership, business, performance, and winning twice in life and work.</strong></p><p><br></p><p><br></p><p><a href="http://Austincheviron.com">Austincheviron.com</a></p>
June 21, 2026
S1 EP15 - Build a Real Estate Team That Runs Without You
<p>Building a successful real estate team isn't about adding more agents—it's about building the right culture, setting uncompromising standards, and creating a business that can thrive without depending on you. In this solo episode of Winning Twice, Austin Cheviron shares the leadership principles that helped him grow one of the nation's top-performing real estate teams while preparing himself to transition from top-producing agent to true CEO. He breaks down the critical differences between production and leadership, why most teams struggle with culture and accountability, how to build a referral-driven business instead of relying on purchased leads, and why financial systems—not higher income—create lasting freedom. Austin also introduces his framework for transitioning out of production, explains the importance of coaching agents beyond sales skills, and offers practical strategies for recruiting, retaining, and developing elite talent. Whether you're an aspiring team leader, an established broker, or preparing for your next stage of business, this episode provides a blueprint for building a company that supports both your vision and your life.</p><p><strong>In this episode, you'll learn:</strong></p><ul><li>Why culture is the foundation of every successful team.</li><li>How higher standards attract higher-performing agents.</li><li>The difference between an agent, team leader, and CEO mindset.</li><li>Why database, sphere of influence, and referral business outperform purchased leads.</li><li>The financial systems every business owner should build before scaling.</li><li>Austin's framework for gradually transitioning out of production.</li><li>How coaching life, business, and finances creates stronger agents and better businesses.</li><li>The hidden financial mistakes that keep team leaders stuck.</li></ul><p><strong>Resources & Contact</strong></p><p>Interested in Austin's live Team Leader Training or CEO Transition Program?</p><p>📧 Email: <a href="mailto:austin@cheviron.net"><strong>austin@cheviron.net</strong></a></p><p><br></p><p>Austin discusses:</p><ul><li>The <strong>Money Puzzle</strong> framework and Wealth Machine financial system.</li><li>His live Team Leader Training (July & August).</li><li>CEO Transition Training (September).</li><li>Coaching for agents, team leaders, and business owners ready to scale without sacrificing their lives.</li></ul><p><br></p><p><br></p><p><br></p><p>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.</p><p><strong>Subscribe for more conversations on leadership, business, performance, and winning twice in life and work.</strong></p><p><br></p><p><br></p><p><a href="http://Austincheviron.com">Austincheviron.com</a></p>
June 15, 2026
S1 EP14 Don Hobbs - The Best Marketer Wins!
<p>In this episode of Winning Twice, Austin Cheviron sits down with legendary marketer, speaker, and coach Don Hobbs for a conversation that spans four decades of business, personal growth, and reinvention. Don shares what it was like learning directly under Jim Rohn at just 18 years old, working alongside a young Tony Robbins, building Hobbs Herder into one of the most influential marketing companies in real estate, partnering with Gary Keller, and eventually leading Success Magazine. Together, Austin and Don explore the decisions that shape a life: why proximity matters, how the people around you influence your future, the reality of failure behind every success story, and the courage it takes to leave comfort behind in pursuit of growth. They unpack lessons on self-worth, money, marketing, storytelling, and what it truly means to "win twice" by becoming the person capable of creating lasting success. If you've ever wondered how to navigate setbacks, elevate your thinking, and build a life aligned with your values, this conversation is packed with timeless wisdom from two men committed to helping others play a bigger game.</p><p><br></p><p>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.</p><p><strong>Subscribe for more conversations on leadership, business, performance, and winning twice in life and work.</strong></p><p><br></p><p><strong>Contact & Resources</strong></p><ul><li>Connect with Don Hobbs on social media:<br> <ul><li>Instagram/Facebook: <strong>@TheRealDonHobbs</strong> and <strong>Don Hobbs</strong> (as mentioned in the episode)</li></ul></li><li> </li><li>Phone: <strong>949-929-5185</strong> (Text Don and let him know you're a friend of Austin's.)</li></ul><p><br></p><p><br></p><p>#WinningTwice #AustinCheviron #Productivity #Leadership #HighPerformance #RestWeek #BusinessGrowth #TimeManagement #Entrepreneurship #SuccessMindset</p><p><br></p><p><br></p><p><a href="http://Austincheviron.com">Austincheviron.com</a></p>
16 total episodes available
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