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 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.
