The Real Payoff May Be in Owning, Not Selling

The Real Payoff May Be in Owning, Not Selling

From 21 Hats Podcast by 21 Hats

May 12, 2026 · 49 min · Episode 293

About this episode

Kate Morgan discusses the potential benefits of owning a business longer rather than selling it immediately.

When Kate Morgan started thinking seriously about selling her business, she assumed the big payoff would come at closing. But as she tells David C. Barnett and Paul Downs this week, she’s come to understand that the smarter move might be not selling—at least not yet. Why? Because if the business keeps performing and she can gradually remove herself from the day-to-day operations, she may ultimately make more money by continuing to own it. That’s partly because, as David explains, small businesses often sell for lower multiples than owners expect. Which means the real value may not be in a clean exit, but in continuing to collect profits while slowly transitioning ownership to key employees. “So you'll be selling the business,” says David, “and you'll be collecting dividends or distributions on top of that. This is one of the most lucrative exits there can be.” Of course, delaying a sale comes with its own risks. Markets change. Businesses cool off. Buyers get nervous. “You have to make the decision and make the sale happen while you've got a full head of steam,” David warns. Wait too long, and the numbers can start sliding in ways that dramatically reduce what buyers are willing…

People in this episode

Hosts: David C. Barnett, Paul Downs

Guest: Kate Morgan

Topics covered

  • business ownership
  • selling a business
  • entrepreneurship
  • management challenges
  • financial strategy

Keywords

  • business sale
  • ownership
  • profits
  • dividends
  • management
  • layoffs
  • entrepreneur

Mentioned in this episode

Organizations: Reddit

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