In this episode, Austin sits down with Patrick Shelley—entrepreneur, global traveler, investor, and pilot—to explore the intricacies of risk, growth, and grit. From starting multiple ventures like Aruna, Tributan, and Dapper Sites to managing burnout, failures, and constant reinvention, Patrick shares how building a life of freedom comes with both weight and reward. They dive into how reading hundreds of books, visiting over 85 countries, and flying Gulfstreams has refined Patrick’s perspective on time, trust, and choosing purpose over prestige. Whether you’re chasing your next milestone or questioning if it's all worth it, this episode offers clarity on the power of autonomy, the art of balance, and the value of asking better questions.