Winning Twice With Austin Cheviron

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 Birmingham, UK. Lee, an Australian sales trainer and creator of the Complete Salesperson Course, was the day-one keynote while Austin took the stage on day two, and a conversation between the two eventually turned into an opportunity to reconnect from opposite sides of the world. In this episode, Austin and Lee talk about teams, systems, sales, leadership, and building relationships—but there’s another conversation happening underneath it all. Listen to the questions Austin asks, the similarities the two discover, and the way a relatively new relationship begins creating possibilities for the future. Austin has always believed in planting seeds before you know exactly where they’ll lead, and this conversation is a real-time example of what that looks like. Maybe it’s simply two people getting to know each other. Maybe it leads to Austin speaking in Sydney someday. Either way, it starts the same way most worthwhile opportunities do: with a conversation, genuine curiosity, and the willingness to follow up.

Lee Woodward is an Australian real estate trainer, presenter, producer, and creator of The Complete Salesperson Course, a training system designed to help real estate professionals build more structured, consistent, and repeatable sales businesses.

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.