Winning Twice With Austin Cheviron

S1 EP21 Russ Laggan - You Don’t Stop Making Mistakes—They Just Get More Expensive

Austin Cheviron — Sun, 09 Aug 2026 11:24:43 -0700

What if the mistakes you’re making aren’t really mistakes—but unintended results that are teaching you how to win?

In this episode of Winning Twice, Austin Cheviron sits down with Russ Laggan for a fast-moving conversation about failure, fear, money, freedom, legacy, and learning to enjoy the journey along the way. Russ shares stories from a life that has taken him from working on the railroad and hanging onto moving trains to climbing Mount Rainier, racing motorcycles, building businesses, and helping others grow.

Russ talks about his philosophy of “failing forward faster” and why the people who reach the top aren’t the ones who never fall—they’re the ones who learn how to get back up. He explains why successful people don’t stop making mistakes; they simply start making mistakes with more zeros.

The conversation then turns toward money and the difference between income and wealth. Russ explains why making more money doesn’t necessarily solve the fear of not having enough, why net worth matters more to him than a paycheck, and why true financial freedom is ultimately about having the ability to live the life you actually want.

Russ also breaks down the five stages of a career: making money, taking control of your time, creating freedom, building a legacy, and ultimately helping others build theirs. But perhaps the biggest lesson comes at the end of the conversation: sometimes the goal isn't to keep changing the recipe. Sometimes, you need to stop fiddling with everything and simply enjoy the life you’ve worked so hard to create.

Because winning twice isn't just about getting where you wanted to go.

It’s about becoming the kind of person who can appreciate being there.

And as Russ puts it: enjoy today. Enjoy the process. Enjoy the thing you're working on. That’s how you live a beautiful life.

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.

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S1 EP20 Why Taking Time Off Makes You More Money

Austin Cheviron — Sun, 02 Aug 2026 10:33:33 -0700

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.

Subscribe for more conversations on leadership, business, performance, and winning twice in life and work.

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S1 EP19 Jason “Iron Panda” Bussey - Winning Starts Within: Why Money Can't Fix You

Austin Cheviron — Mon, 27 Jul 2026 18:02:43 -0700

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

Subscribe for more conversations on leadership, business, performance, and winning twice in life and work.

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S1 EP 18 - The Financial Systems That Build Wealth

Austin Cheviron — Mon, 20 Jul 2026 08:16:08 -0700

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.

Subscribe for more conversations on leadership, business, performance, and winning twice in life and work.

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S1 EP17 Cory Williams - Alignment Over Achievement

Austin Cheviron — Sun, 05 Jul 2026 12:34:48 -0700

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

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

Austin Cheviron — Sun, 28 Jun 2026 11:58:27 -0700

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.

Subscribe for more conversations on leadership, business, performance, and winning twice in life and work.

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

Austin Cheviron — Sun, 21 Jun 2026 15:57:55 -0700

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 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.

Subscribe for more conversations on leadership, business, performance, and winning twice in life and work.

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S1 EP14 Don Hobbs - The Best Marketer Wins!

Austin Cheviron — Sun, 14 Jun 2026 21:37:52 -0700

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.

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

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S1 EP13 Dave McGhee - Why Most Entrepreneurs Fail Before They Ever Start

Austin Cheviron — Mon, 08 Jun 2026 13:04:21 -0700

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

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

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S1 EP12 Rest Week - The Monthly Reset That Changed My Business

Austin Cheviron — Sun, 31 May 2026 14:33:07 -0700

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

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

S1 EP11 Nick Krem - AI Is Changing Everything — Here’s What Still Matters

Austin Cheviron — Sun, 24 May 2026 10:07:10 -0700

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.

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

https://krem.ai/

Austincheviron.com

S1 EP10 Melissa Johnson - Why Working Harder Was Making Life Worse

Austin Cheviron — Sun, 17 May 2026 15:42:53 -0700

What happens when success stops being about grinding harder and starts becoming about building better systems? In this episode, Austin sits down with Melissa Johnson for a candid conversation about growth, mentorship, and what happens when you stop trying to do everything your own way.

Melissa shares her journey from first hearing Austin speak years ago to eventually committing to coaching and rebuilding her life and business from the ground up. Together they unpack lessons on finances, relationships, authentic leadership, creating sustainable systems, and why the things that feel too simple are often the things that create the biggest breakthroughs.

They also dive into the hidden cost of hustle culture, why working 24/7 isn’t a badge of honor, and how finding balance creates more impact at home and in business.

If you've ever felt overwhelmed, stuck trying to force growth, or wondered whether success can actually feel peaceful, this conversation will challenge the way you think.

Austincheviron.com

S1 EP9 Ken Hirschman - The Seasons of Success: Sacrifice, Growth, and Best Life

Austin Cheviron — Sun, 10 May 2026 12:31:15 -0700

In this episode of Winning Twice, Austin sits down with real estate entrepreneur Ken Hirschman for an honest conversation about growth, leadership, sacrifice, and what it really takes to build something meaningful over time. From working 55-hour weeks as an Aldi district manager to building Best Life & Company into an 1,100-deal real estate organization, Ken shares the mindset shifts, risks, and hard seasons that shaped his journey. Together, they unpack the hidden cost of complacency, why sustainable success requires intentional rest, and how culture, relationships, and self-awareness ultimately become the foundation for long-term growth. This episode feels less like an interview and more like two entrepreneurs talking life on the golf course—covering business, family, vision, burnout, and the pursuit of building a life you actually enjoy living.

Austincheviron.com

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.

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.