We’ve all heard it: “Pick one thing. Focus. Go all in.” But what if that advice doesn’t apply once you’ve built real optionality?
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In this episode, I’m joined by Mark Cleveland—an experienced entrepreneur, investor, and self-described parallel entrepreneur—to rethink how owners can design the next chapter of life. Instead of scaling endlessly or exiting just to feel free, Mark shows how business can be a platform to fund the life you actually want. Not someday—now.
We unpack how to reclaim your time, align your ventures with your values, and stop optimizing for someone else’s scoreboard. If you’ve built a successful company but feel boxed in by what comes next, this episode is a wake-up call. You don’t need to sell to find meaning. You need clarity, ownership, and the courage to design your future on purpose.
Mark Cleveland is a lifelong entrepreneur, investor, and business builder who’s launched and led multiple companies across industries—from logistics to retail to software. Rather than optimizing for scale or exits, Mark intentionally structures his ventures around what gives him energy, purpose, and time with his family. His philosophy flips the default growth narrative and shows that the real prize of entrepreneurship isn’t scale—it’s alignment.
Chapters:
- (00:00) Introduction and guest welcome through Dan Golden connection
- (02:58) The parallel entrepreneur mindset rejecting the one business rule
- (14:42) What fulfillment looks like after buying back your time
- (26:49) Using business structure to fund curiosity and personal growth
- (37:41) Constraining growth by choice and turning down capital
- (46:23) Designing around your values, not the market's expectations
- (55:26) Framework versus goals for flexible decision-making structures
- (01:03:00) Optionality without exit and designing the next chapter purposefully
- Rate, comment, and share with the owner/operators you know!
Resources:
Mark Cleveland on LinkedIn https://www.linkedin.com/in/markhcleveland/
37signals – calm company inspiration https://37signals.com/
Ryan Tansom Website https://ryantansom.com/
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