All Things Endurance Episode 37: Employee to Entrepreneur - Transitioning to a Life of Self-Employment’ with Guest Jonathan Levitt
Aug 15, 2025
Jonathan Levitt, founder of Long Run Labs and host of 'For the Long Run,' shares his journey from a senior sales executive to full-time entrepreneur. He discusses the emotional hurdles of leaving a secure job, emphasizing the impact of community support and mentorship. Levitt provides invaluable advice for aspiring entrepreneurs about the importance of playing the long game and not waiting for the perfect moment to transition. He encourages overcoming fears of failure by betting on oneself and highlights the loneliness often faced in entrepreneurship.
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From Casual Runner To Podcaster
- Jonathan Levitt started running seriously after the 2013 Boston Marathon bombing and quickly immersed himself in the sport.
- He launched the For the Long Run podcast in January 2019 and has produced ~385 episodes to date.
Launching Long Run Labs And The Huddle
- Jonathan launched Long Run Labs in June to focus on endurance plus entrepreneurship conversations.
- He’s also building a community called The Huddle and running podcast collective sponsorship work.
Build Before You Quit
- Build your side project while employed until it shows traction before quitting your job.
- If 10% time success would scale significantly at 100% time, then consider betting on yourself.