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Join the Gildre Community: https://www.gildre.com/membership The Essential Founder Newsletter: https://gildre-for-founders.beehiiv.com/ Most entrepreneurs are forced to choose between their passion and their stability—Fritz Lanman reveals how he built a multi-billion dollar career by daring to switch from Silicon Valley’s corporate world to founding innovative startups that redefine wellness. What if your next move could unlock not just success, but personal freedom? In this episode, Fritz shares the surprising story behind his transition from a Microsoft executive to a founder leading companies like ClassPass and Mindbody, revealing the secret strategies that helped him leverage early investments into industry giants. You’ll discover how he identified emerging health and wellness trends years ahead, the real role luck plays in entrepreneurship, and how to build a resilient mindset when faced with inevitable setbacks. We break down Fritz’s journey from playing college sports to investing billions, including the behind-the-scenes details of his investment in Facebook when it was still an up-and-coming platform, and how he strategically pivoted his career to build companies that prioritize lifestyle and impact. He explains why acknowledging luck is crucial, and how embracing uncertainty can turn risks into opportunities. This episode is perfect for aspiring founders, ambitious investors, and anyone curious about building a meaningful, scalable business in a rapidly changing world. Whether you're dreaming of launching your first startup or looking for the confidence to make bold career changes, Fritz’s insights will inspire you to act with clarity and courage. Don’t miss the lessons from a seasoned entrepreneur who’s mastered the art of working hard, working smart, and knowing when to pivot. Get ready to challenge everything you thought you knew about success—because the best opportunities often come disguised as risks. Timestamps: 00:00 - Introduction and Fritz’s unique career journey 02:00 - Mentors from childhood and athletic inspirations 04:30 - Growing up as the oldest sibling and family dynamics 08:15 - Moving from sports to academics at Yale and studying abroad in Italy 11:00 - How studying history and Italian shaped Fritz’s perspective 14:49 - Early interest in technology and the Silicon Valley environment 19:19 - Climbing the ranks at Microsoft and leading the Facebook investment 22:30 - The logic and intuition behind investing in Facebook 25:33 - Transition from Microsoft to London, and living abroad experiences 27:46 - The decision to move ClassPass operations to Missoula and benefits of remote work 36:29 - Building a career in investing and moving into entrepreneurship 44:46 - Key advice for future entrepreneurs and managing risk 47:22 - The reality of work-life balance for entrepreneurs 49:47 - Closing thoughts and appreciation #classpass #Mindbody #DopplerLabs Hank V Hill Ray Ozzie Steve Ballmer Bill Gates Mark Zuckerberg