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 paths crossed, how the Winning Twice podcast came to life, and the shared ideas that have kept them working together.
Randy takes Austin back to their first meeting at an eXp event, where Austin's relentless curiosity immediately stood out, before sharing his own unlikely journey from solving problems and building a training video library to producing major virtual events, livestreams, and conversations with some of the biggest names in the industry. Along the way, they unpack what years of producing and speaking have taught them about communication, authenticity, listening, taking risks, recognizing a need and being willing to fill it—and why the quality of a conversation matters far more than making everything look perfect. The conversation eventually gets to the heart of Winning Twice: real success isn't winning in one category while everything else falls apart. It's the ongoing work of balancing business, finances, family, relationships, personal life, and faith while staying true to the values that made the success worth pursuing in the first place.
Randy also introduces his own podcast, Sweeter After Difficulty, and the philosophy behind “Honest Conversations. Better Lives.”—using honest conversations and better questions to create awareness, discover new options, and learn from the difficulties that shape us. Austin closes by pointing listeners to his own deeply personal appearance on Sweeter After Difficulty, where he and Randy go beyond business and unpack some of the adversity that helped shape the man, coach, father, and entrepreneur Austin is today.
Continue the conversation:
Listen to Sweeter After Difficulty
Check out Austin's Sweeter After Difficulty episode, Built, Not Born: Redefining Success with Austin Cheviron.
Connect With Randy at RandyHighsmith.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.
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