S1 EP15 - Build a Real Estate Team That Runs Without You

S1 EP 18 - The Financial Systems That Build Wealth

Austin delivers a practical framework for building long-term financial freedom by focusing on systems instead of income alone. The core message is that wealth isn't created by making more money—it's created by having a clear vision, intentional habits, and a process that directs every dollar before it's ever spent. He walks listeners through the importance of defining a financial vision, tracking personal spending, creating a "wealth machine" that automatically allocates income toward taxes, investments, and giving, and building a "money wheel" to fund future opportunities. Throughout the episode, Austin emphasizes that generosity isn't something you do once you've become wealthy—it's one of the habits that helps shape the person capable of creating lasting wealth. Whether you're an entrepreneur, business owner, or simply trying to gain control of your finances, this episode offers actionable strategies to help you stop reacting to money and start leading it with purpose. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com [http://Austincheviron.com]

S1 EP17 Cory Williams - Alignment Over Achievement

This episode centers on a powerful shift that many entrepreneurs eventually face: moving from chasing success to building a life worth succeeding for. Austin Cheviron sits down with Colorado real estate leader Cory Williams to unpack the lessons that transformed Cory's business, health, faith, marriage, and mindset after years of outward success masked an unsustainable foundation. Together they explore the power of planned rest, simplifying your business, aligning your life with your values, accepting feedback, and making decisions based on long-term vision instead of short-term ego. Rather than offering shortcuts, this conversation presents a practical framework for building a business that serves your life—not one that consumes it. Whether you're an entrepreneur, business owner, or simply feeling burned out despite external success, this episode is a reminder that true victory comes from winning in both business and life. Connect with Cory Williams * Facebook: Cory Williams * Instagram: @coryandcompany * Website: CoryAndCompany.com 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com [http://Austincheviron.com]

S1 EP16 Ryan Woodruff - Why High Achievers Burn Out—and What Comes Next

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. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com [http://Austincheviron.com]

S1 EP15 - Build a Real Estate Team That Runs Without You

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. In this episode, you'll learn: * Why culture is the foundation of every successful team. * How higher standards attract higher-performing agents. * The difference between an agent, team leader, and CEO mindset. * Why database, sphere of influence, and referral business outperform purchased leads. * The financial systems every business owner should build before scaling. * Austin's framework for gradually transitioning out of production. * How coaching life, business, and finances creates stronger agents and better businesses. * The hidden financial mistakes that keep team leaders stuck. Resources & Contact Interested in Austin's live Team Leader Training or CEO Transition Program? 📧 Email: austin@cheviron.net [austin@cheviron.net] Austin discusses: * The Money Puzzle framework and Wealth Machine financial system. * His live Team Leader Training (July & August). * CEO Transition Training (September). * Coaching for agents, team leaders, and business owners ready to scale without sacrificing their lives. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Austincheviron.com [http://Austincheviron.com]

S1 EP14 Don Hobbs - The Best Marketer Wins!

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. 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. Subscribe for more conversations on leadership, business, performance, and winning twice in life and work. Contact & Resources * Connect with Don Hobbs on social media:   * Instagram/Facebook: @TheRealDonHobbs and Don Hobbs (as mentioned in the episode) *   * Phone: 949-929-5185 (Text Don and let him know you're a friend of Austin's.) #WinningTwice #AustinCheviron #Productivity #Leadership #HighPerformance #RestWeek #BusinessGrowth #TimeManagement #Entrepreneurship #SuccessMindset Austincheviron.com [http://Austincheviron.com]