Ryan Deiss is the Founder and CEO of The Scalable Company (Scalable.co), DigitalMarketer.com, and a Founding Partner at Scalable Equity, LLC, a venture equity accelerator that builds and acquires B2B media, service, and software brands.
In his 20+ year career as a serial entrepreneur, investor, and advisor, Ryan has started 17 companies, exited 4, and his portfolio of companies generated in excess of $200M in revenue last year, alone. As one of the most respected minds in digital marketing, Ryan continues to shape the way entrepreneurs grow smarter, scale sustainably, and lead better.
In this episode, Chris and Ryan discuss the napkin moment that completely transformed Ryan’s approach to business, and ultimately became the foundation for one of the most widely adopted marketing frameworks in the world.
He also opens up about redefining success after multiple exits, and the lessons that helped him prioritize purpose and family without losing his entrepreneurial edge.
This episode is a deep dive into what it really takes to build lasting success, without losing sight of what matters most.
In this Episode You'll Learn
- The story behind Ryan’s “million-dollar napkin” and how simplicity became his superpower
- Why most entrepreneurs overcomplicate their businesses and how to fix it
- The two turning points that shaped Ryan’s journey through burnout and back
- How to set calendar-based boundaries that protect your time and family
- The “Big 3” habit that keeps Ryan consistent and focused every week
Episode Timestamps
- 02:38 – Ryan’s Early Business Journey
- 05:45 – The Million Dollar Napkin
- 10:55 – Balancing Business and Family Life
- 15:50 – Setting Boundaries for Personal and Professional Success
- 21:11 – Flexible Time Blocking Strategies
- 22:13 – Personal Habits and Routines
- 23:49 – Weekly and Quarterly Reviews
- 30:34 – Avoiding Burnout
- 34:24 – Celebrating Wins and Learning from Mistakes
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Thanks for listening to The Long-Haul Leader podcast. See you next week with more insights to help you lead with purpose, resilience, and impact.
