What Sports Legends Teach Us About Business Value

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Ever wonder why some of the greatest athletes struggle as coaches? It’s not just a sports story—it’s a business lesson. Because just like on the field, being the star player in your business doesn’t guarantee you’ll succeed as its leader. And if your endgame is to one day sell that business for a premium, that transition is critical.

Look at Wayne Gretzky. He’s arguably the greatest hockey player of all time—but as head coach of the Phoenix Coyotes, he missed the playoffs four straight seasons. Same with baseball legend Ted Williams. As a player, unmatched. As a manager? No postseason success.

Now contrast that with coaching legends who never played professionally. Andy Reid never played in the NFL, yet has won three Super Bowls. Greg Popovich, one of the most successful NBA coaches ever, never played pro ball. Why? Because coaching is a different skillset—and the same holds true for business.

From Founder to Coach: Why It Matters for Company Value

Data from over 80,000 companies in the Value Builder System™ shows that businesses able to operate without their owner for three months are three times more likely to receive a premium acquisition offer (defined as 6x or more of pre-tax profit).

In plain terms? If your business needs you to run, sell, or deliver, it’s not worth as much. But if you can step back—and your team still performs—you’ve built something truly valuable.

Jason Bagley’s Shift from Star to System

Jason Bagley, founder of Firing Squad, started out doing everything himself—especially copywriting, which he called his “ninja skill.” But he wanted more than just a high-paying job. He wanted a business that could run (and one day sell) without him.

Here’s how he made the shift from player to coach:

  1. Build a Playbook: He created a shared library of strong and weak copywriting examples for his team to learn from.
  2. Train with Video: He recorded screen-share feedback, explaining his process so others could replicate it.
  3. Let Go of Perfection: Bagley accepted work at 80% of his personal standard. Not because he didn’t care—but because progress matters more than polish.

That mindset shift allowed Bagley to build a team that could carry the work forward—and ultimately helped him sell Firing Squad to Southern Web in 2020.

Letting Go Is How You Level Up

Yes, it’s hard to hand off what you’re great at. But building a business that depends on your individual brilliance is like building a team that can’t win without its star player on the field. If you want a business that’s scalable, sellable, and significantly more valuable—you’ve got to become the coach.

Ready to step out of the day-to-day and build something that runs without you?
Let’s talk about your next move—and how to build a business buyers want to own.

📩 Email: paulwildrick@provengain.com
📞 Call: 925.963.9665
🌐 Visit: www.provengain.com