#49: Andy Roddick, Former #1 World Tennis Player & Andy Roddick Foundation CEO—Don’t Be Afraid to Ask Questions

Today’s guest is hall of fame and former world #1 tennis player, Andy Roddick. You may remember him destroying opponents with his serve, or winning the 2003 US Open, or even hosting Saturday Night Live! But these days, he’s doing all kinds of other fun stuff. He’s the CEO of the Andy Roddick Foundation, which supports kids in low-income communities. He’s co-founded two companies, one in healthcare and another in commercial real estate. And if all that weren’t enough, he has also launched Sweetens Cove Spirits and is out there making Tennessee bourbon! Can you imagine pivoting from what you’ve known your whole life and jumping headfirst into one new situation after the other? Andy knows what it’s like to feel out of place and uncomfortable doing something new. But he also knows what it takes to get comfortable. He asks lots of questions. He prepares diligently. And he knows how to develop the right relationships. Every leader finds themselves in new situations, where we don’t know the lay of the land. This conversation will show you exactly how to navigate those situations. You’ll also learn: How to overcome the resistance of getting into a new venture you don’t understand A mindset shift that will change the way you think about preparation The power of a simple ritual to stay mentally resilient The surprising benefits of productive conflict and how to lean into it Take your learning further. Get proven leadership advice from these (free!) resources: The How Leaders Lead App: A vast library of 90-second leadership lessons to stay sharp on the go Daily Insight Emails: One small (but powerful!) leadership principle to focus on each day Whichever you choose, you can be sure you’ll get the trusted leadership advice you need to advance your career, develop your team, and grow your business.