A 26-year-old business owner called recently into Dave Ramsey‘s “EntreLeadership” podcast with a tough decision: sell the family business for millions or keep building what his father started.

Sell Now Or Build Further?

Dan co-owns a New York-based restaurant cleaning company with his 65-year-old father, who founded the business and is now ready to retire. The company brings in $4.75 million annually and employs 80 cleaners.

After years of working together, a big competitor has offered to buy them out for $6 million. The offer includes $4.5 million in cash and $1.5 million in rollover equity, along with a leadership role for Dan to run the acquiring company's New York City operations.

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Dan said he and his dad would split the proceeds evenly. “It’s more money than either of us have ever seen,” he admitted.

Ramsey told Dan to think beyond the immediate windfall. “One of the decision-making formulas I use is I get out of the moment and I extrapolate out decades,” he said. “When you’re 56, and you look back on your life, how are you going to feel about the 26-year-old version of you?”

Dan said he hadn’t considered that. “I never really thought that far out into the future.” He knows that, invested properly, that chunk of change could be worth several million more down the road.

Ramsey agreed the math made sense: “If you put $2 million in your pocket at 26, it’s not a bad day.”

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Still, he cautioned against chasing a payout just because it looks good on paper. “I’ve known people who got hundreds of millions of dollars for selling their business, and the only thing they got other than that was wishing they didn’t sell it,” he said.

He told the story of a man who sold his company for $400 million but later called it “the dumbest thing I ever did,” crying because the company lost its soul under new ownership. “Selling something for a big chunk of change is not always something that is without regret,” Ramsey added.

But he didn’t think Dan would fall into that trap. “This is an excellent exit for [your dad] and an excellent on-ramp for something else for you,” he said. “I think you do this.”

Still, he left listeners with a straightforward reminder: “Just because you get a pile of money doesn’t mean automatically we need to do it.”

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