Jonathan Lowenhar
Co-founder and Managing Partner at Enjoy The Work
Co-founder of Enjoy The Work, a firm that helps founders become CEOs, known for his distinction that founder is a state of being while CEO is a craft that must be learned, his criticism of founder mode as an excuse not to learn the job, and the Magic Box paradigm for thinking about exits.
Dimension Profile
Key Themes
Episode Summary
Jonathan Lowenhar explains his firm Enjoy The Work's approach to helping founders become CEOs, built on the core insight that founder is a state of being while CEO is a craft that must be deliberately learned. He critiques founder mode as often being an excuse not to learn the CEO job, and introduces frameworks like Phase 1 versus Phase 2 thinking and the Magic Box paradigm for evaluating exits.
Leadership Principles
- → Founder is a state of being, CEO is a craft — being a great founder doesn't automatically make you a great CEO, and the CEO skills must be deliberately learned
- → Founder mode can become an excuse not to learn the job — staying in the weeds forever is a coping mechanism, not a leadership strategy
- → Phase 1 is about building product-market fit, Phase 2 is about building the company — the skills and behaviors that make you great at Phase 1 can actively hurt you in Phase 2
Notable Quotes
"Founder is a state of being. CEO is a craft. Being a great founder doesn't automatically make you a great CEO."
— On the core distinction driving his coaching practice
"Founder mode can become an excuse not to learn the job. Staying in the weeds forever is a coping mechanism, not a leadership strategy."
— On his criticism of the founder mode concept
"The skills that make you great at Phase 1 — finding product-market fit — can actively hurt you in Phase 2, which is building the company."
— On why founders struggle as their companies scale
Want to know how you compare?
Take the Assessment