Winning Twice With Austin Cheviron

What if taking time off could actually help you make more money, perform at a higher level, and enjoy your life more? In this episode of the Winning Twice Podcast, Austin Cheviron breaks down the concept of the Rest Week—a dedicated week each month designed to recover, reset, handle the things that get neglected, and come back to work with more energy and focus. Austin explains why knowing a break is coming allows your brain to run harder during the weeks that matter, why entrepreneurs often confuse exhaustion with productivity, and how protecting time away from work can actually increase your capacity to produce. He also talks about the role of ego, the fear of missing opportunities, and the importance of surrendering the idea that everything has to be perfect before you can take a break. From family time and travel to finances, health, and the simple things that never seem to get done, Rest Week is about creating space for the important things—not just the urgent ones. If you're a high performer who feels like you're constantly running but isn't enjoying the journey anymore, this episode offers a different way to think about winning twice: building a successful business without sacrificing the life you're building it for.

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

Most people think success starts with better strategies, more money, or harder work. Jason Bussey believes it starts with becoming a healthier human being.

In this episode of Winning Twice, Austin Cheviron sits down with psychotherapist, business consultant, and entrepreneur Jason "Iron Panda" Bussey to unpack the unexpected friendship that began in a mastermind group—and why authentic relationships often become the greatest return on any investment.

Together they explore why human behavior drives business performance, why money only magnifies who you already are, and why leadership begins with fixing the person in the mirror. Jason shares lessons from coaching high-performing entrepreneurs, working with couples rebuilding trust after infidelity, and helping business owners design lives instead of living by default.

If you've ever believed that more money, more success, or more achievement would finally make you happy, this conversation may completely change the way you think about winning.

Connect with Jason Bussey

• Therapy Practice: https://capstoneatlanta.com
• Coaching & Business Development: https://iamironpanda.com
• Text Jason directly: 404-594-0625

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

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

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

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

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: [email protected]

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

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

What does it really mean to win in both life and business?

In this episode of Winning Twice, Austin Cheviron sits down with business coach and leadership expert Dave McGhee for a conversation packed with hard-earned wisdom from decades of coaching entrepreneurs, team leaders, and service-based business owners.

After helping coach more than 4,500 business owners and leading a coaching organization with over 80 coaches, Dave recently stepped out on his own to build his private coaching practice. The conversation explores the lessons learned from that transition, the mistakes entrepreneurs make when starting something new, and why most people dramatically underestimate the time required to build meaningful success.

Austin and Dave dive into:

• Why there are no unrealistic goals—only unrealistic timelines
 • How to identify what you're naturally gifted at and build your business around it
 • The hidden difference between marketing and genuine relationship-building
 • Why most entrepreneurs struggle with sales conversations and how to reframe them
 • The power of setting boundaries before your business takes over your life
 • Why successful leaders focus on direction, not control
 • The difference between coaching, consulting, mentoring, and training
 • How to create a business that supports your life instead of consuming it

Whether you're building a team, growing a company, launching a new venture, or simply trying to find better balance, this episode offers practical insights you can apply immediately.

Because success isn't about choosing between life and business.

It's about winning twice.

Connect with Dave McGhee:

Website: https://coachdavemcghee.com

Social Media: @CoachDaveMcGhee

Subscribe for more conversations on leadership, business growth, mindset, and building a life worth living.

#WinningTwice #BusinessCoaching #Entrepreneurship #Leadership #SmallBusiness #BusinessGrowth #Mindset #Success #PersonalDevelopment #AustinCheviron #DaveMcGhee

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.

#WinningTwice #AustinCheviron #Productivity #Leadership #HighPerformance #RestWeek #BusinessGrowth #TimeManagement #Entrepreneurship #SuccessMindset

Austincheviron.com

What if the secret to achieving more… is actually doing less?

In this special Rest Week episode of Winning Twice, Austin Cheviron breaks down one of the most powerful systems behind his ability to lead multiple companies, stay organized, and avoid burnout: Gather & Focus.

Most people aren't overwhelmed because they have too much to do. They're overwhelmed because they're carrying around hundreds of unfinished thoughts, forgotten commitments, buried text messages, and loose ends that quietly drain their energy.

Austin shares the exact monthly process he uses to clear mental clutter, recover lost opportunities, and create the calm needed to perform at a high level. From reviewing text messages and photos to cleaning up calendars, emails, and notebooks, this simple two-hour exercise can help you regain control and enter your next season with clarity.

If you've ever felt like you're constantly running but never fully caught up, this episode is for you.

In This Episode:

• Why high achievers need structured recovery
• The hidden cost of mental clutter
• How to uncover forgotten opportunities and commitments
• Austin's Gather & Focus framework
• Turning chaos into clarity in just two hours
• Why calm is a competitive advantage

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.

#WinningTwice #AustinCheviron #Productivity #Leadership #HighPerformance #RestWeek #BusinessGrowth #TimeManagement #Entrepreneurship #SuccessMindset

Austincheviron.com

In this episode of Winning Twice, Austin Cheviron sits down with AI entrepreneur and speaker Nick Krem for a real conversation about business, health, discipline, relationships, and the future of AI. Nick shares his journey from working 15-hour days in a real estate call center to becoming a leader in the AI space, while also opening up about the hidden costs of speaking on stages, burnout, rebuilding his health, losing 75 pounds, and learning how to stay grounded while business grows. Together, they dive into why emotional intelligence, human connection, and real-world experience are becoming more valuable than ever in an AI-driven world, and why the people who win in the future won’t just be the most technical — they’ll be the most human.

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.

#WinningTwice #NickKrem #AustinCheviron #ArtificialIntelligence #Entrepreneurship #RealEstate #BusinessPodcast #SelfDevelopment #Leadership #AI

https://krem.ai/

Austincheviron.com