#59 Will Fry: The Great Wealth Transfer And Saving Small Business Ownership in America

Going Direct Conversations · Apr 7, 2026 · 1h 3m

I sat down with Will Fry, founder and CEO of American Operator, to talk about one of the biggest questions in the U.S. economy: who will own the next generation of small businesses?

Among the topics we discuss are:

* Why allowing Private Equity to buy up Main Street is a disaster for local communities.

* The Great Ownership Transfer (6 million businesses for sale).

* The fatal flaw in most small business acquisitions.

* American Operator’s, “Operate-to-Own” Model: From 10% to 70% equity.

* Why Capital, not Operators, is the biggest bottleneck.

Enjoy.

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