All Episodes
Displaying 1 - 20 of 28 in total
S1 EP28 REST WEEK: What If You Have Too Much Time?
Can you really get four weeks of work done in three—and actually create more room for your life? In this Rest Week episode of Winning Twice, Austin Cheviron brings pro...
S1 EP27 Julie Chapman - What’s It Really Like Working With Austin?
What does it really look like behind the scenes of Winning Twice? In this episode, Austin Cheviron turns the questions over to someone who has had a front-row seat to ...
S1 EP26 Brian Fryer - Are You Building a Business—or Building a Life?
What happens when two people who have built successful businesses realize they’ve been designing their lives around many of the same principles? In this episode of Win...
S1 EP25 Rest Week
If you want to run hard, you have to learn how to rest. In this episode of Winning Twice, Austin Cheviron breaks down a practice he's been refining for nearly a decade...
S1 EP24 Lee Woodward - Talking Teams, Business & What Comes Next
This week on Winning Twice, Austin Cheviron shares a conversation from his appearance on Lee Woodward’s podcast after the two first met while speaking at an event in B...
S1 EP23 Randy Highsmith - The Conversation Behind Winning Twice
In this episode of Winning Twice, Austin Cheviron brings longtime friend and producer Randy Highsmith out from behind the camera for a conversation about how their pat...
S1 EP22 Austin Freiburger - The Three Things Every Real Estate Agent Must Learn
What does it actually take to build a successful real estate career from scratch? In this episode of Winning Twice, Austin Cheviron sits down with Austin Freiburger to...
S1 EP21 Russ Laggan - You Don’t Stop Making Mistakes—They Just Get More Expensive
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 s...
S1 EP20 Why Taking Time Off Makes You More Money
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, Aus...
S1 EP19 Jason “Iron Panda” Bussey - Winning Starts Within: Why Money Can't Fix You
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 epi...
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 cr...
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 ...
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 ...
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 ...
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 busines...
S1 EP13 Dave McGhee - Why Most Entrepreneurs Fail Before They Ever Start
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 ...
S1 EP12 Rest Week - The Monthly Reset That Changed My Business
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 ...
S1 EP11 Nick Krem - AI Is Changing Everything — Here’s What Still Matters
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, rela...
S1 EP10 Melissa Johnson - Why Working Harder Was Making Life Worse
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 f...
S1 EP9 Ken Hirschman - The Seasons of Success: Sacrifice, Growth, and Best Life
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...
