The Flynn Skidmore Podcast
How to Think Usefully with Derek Sivers
Jun 05, 2024
Episode 45
Flynn Skidmore / Derek Sivers
Today, I'm thrilled to share a conversation with Derek Sivers, a former musician, programmer, TED speaker, circus clown, and author. From selling his first company for $22 million and donating all the proceeds to charity to moving from Singapore to New Zealand, his vibrant presence shines through every story he shares.
In this episode, Derek and I explore his unique life experiences, from his early days in Fort Greene, navigating the gritty reality of New York City in the late '80s and '90s, to his dynamic career transitions that have led him to writing and podcasting. We discuss the impacts of gentrification, the pivotal decisions that shaped his path, and the vibrant energy of cities that shaped the creative landscape of his time.
Derek's reflections on personal growth, transformation, and the pursuit of authenticity through all phases of life are as enlightening as they are inspiring. His move toward a more balanced approach in his career, reducing sponsored content to maintain authenticity, signals his ongoing evolution as a creator and thinker.
Join us as we dive deep into the mechanics of creativity, the essence of personal change, and the enduring pursuit of living a life true to one's values. Derek's story is a testament to the power of resilience and the beauty of reinventing oneself amidst life's unpredictable waves. So tune in, get inspired, and discover how you can harness your experiences to craft a life filled with purpose and passion.
Connect with Derek:
Connect with Flynn:
Submit your written reviews to
THIS form to be entered into a giveaway to win a 30 min session with me! We'll pull 1 winner at the end of the month.
- Online Community
- Small Group Coaching
- 1:1 Mentorship
Here are 3 ways I can help you:
- Online Community
- Small Group Coaching
- 1:1 Mentorship