Ep. 445 — Mark Cleveland: You Don't Have to Sell or Scale. There's a Third Option.

4 min read

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Episode Summary

You’re sitting on a $10M business kicking off 25% EBITDA and you keep getting told you have two choices: scale it harder or sell it. Mark Cleveland has been pushing back on that frame for a decade. He’s started and sold six companies across six different industries, and the media labeled him a serial entrepreneur. The label never fit. He’s run as many as four companies at once, and he calls the actual pattern parallel entrepreneurship: owning and operating two or more companies at the same time because the second venture isn’t a distraction, it’s where your decisions get sharper and your failures stay isolated. We got into why investors push back on it, why most serial entrepreneurs are actually parallel entrepreneurs and won’t admit it, and what happens to the owner whose identity is welded so tight to the company that selling it produces depression instead of celebration (the owner-operator trap in its purest form). Real examples from Hobby Lobby (the radio-control one, before the craft chain), Swiftwick compression socks, short sea shipping across the Gulf, plus a long stretch on order and chaos, lanterns instead of goals, and expectations as premeditated resentment.

Top 10 Takeaways

  1. There’s a third option between sell and scale: a small giant that throws off cash while you start the next one.
  2. Your second company isn’t a distraction. It’s where your decisions get sharper and your failures stay isolated.
  3. Investors will tell you to focus. Focus is a story told by people who want you predictable.
  4. Most serial entrepreneurs are actually parallel entrepreneurs. They just won’t say it out loud.
  5. If your identity is welded to the company, selling it produces a depression, not a celebration.
  6. Growth isn’t an absolute. A $10M business at 25% EBITDA that rolls into the sunset is a complete win.
  7. Goals are rigid. A lantern lights the next six feet of trail, not the whole mountain.
  8. Expectations are premeditated resentment. The gap between what you wanted and what showed up is where unhappiness lives.
  9. Teach your team to read the financials and the customer. They will leave. That is the point.
  10. Companies are biological organisms. Your job is to keep the system alive, not to be the system.

Sound Bites

“Owning, operating, managing, leading two or more companies at the same time. And often probably you’re thinking about the one that you need to start because you need to solve a problem in one of your businesses that’s just not been addressed correctly.” (@00:14:59) — Mark Cleveland

“Being an owner as an individual where your goal is to have meaningful relationships, lasting impact, and personal growth, using companies as the platform: that’s big enough of an idea that I can bounce all around within it without getting bored.” (@00:52:59) — Ryan Tansom

“I’d rather carry a lantern instead of a goal. And I’d rather let people follow me through in the day or the night.” (@00:57:45) — Mark Cleveland

“At Burning Man, I learned that expectations are nothing more than premeditated resentment.” (@01:02:49) — Mark Cleveland

About This Episode

Mark Cleveland is the founder of The Parallel Entrepreneur Network and host of The Parallel Entrepreneur podcast. He’s started and sold six companies across six different industries (radio-controlled hobby retail at Hobby Lobby, compression socks at Swiftwick in Tennessee, bicycle manufacturing for Ellsworth Handcrafted Bicycles, short sea shipping across the Gulf, and others). In 2014 he was named Entrepreneur of the Year in Nashville. He’s run as many as four companies simultaneously for most of his career and has spent the last decade putting language around what he calls parallel entrepreneurship: the third path between serial entrepreneurship and single-venture focus. Dan Golden made the introduction.

Resources Mentioned

  • The Parallel Entrepreneur — Mark’s podcast and network. — theparallelentrepreneur.com
  • Small Giants by Bo Burlingham — Mark credits this book with breaking the “growth is absolute” assumption.
  • Letting Go (David Hawkins) — On Mark’s nightstand. The frame for what owners do once the systems are built.
  • 10x Is Easier Than 2x (Dan Sullivan / Benjamin Hardy) — Referenced for the “do only what you want” outcome.
  • Who Not How (Dan Sullivan / Benjamin Hardy) — Referenced for hiring the who instead of learning every how.
  • Good to Great (Jim Collins) — Referenced critically — many of those companies are gone, corrupt, or broken up.

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