“When I look back on my life, I overpaid for my big successes every time. And when I tried to get a bargain, get it a little cheaper or get a better deal on it, I ended up usually either getting it and not happy I got it. Or missing it.”
Most business owners struggle with valuation.
They make it too dependent on today’s cash flow.
They use historical earnings to decide what’s worth buying.
They mistake cheap for smart.
They make it too cautious.
They use bargains, spreads, and “safe” allocations that guarantee mediocrity.
They never bet hard enough on anything they can actually control.
Not Jerry Jones. He made his money in oil and gas and then went all-in on the Cowboys.
He recognized that attention compounds faster than profits.
Overpaying for a rare asset had a huge upside.
The paradox of Jerry Jones is that he behaved less like an oilman and more like a collector.
Jerral Wayne Jones Sr., better known as Jerry Jones: owner of the Dallas Cowboys
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Jerral Wayne Jones Sr. is better known as Jerry Jones. He was born on October 13, 1942. He made his fortune in oil and gas. Oil exploration and gas drilling is not a passive-investor game. It is a high-conviction, high-variance operator’s game. He founded an oil exploration company in 1971. He later branched into gas drilling, and those ventures made him a multimillionaire.
Jones is the owner, president, and general manager of the Dallas Cowboys. He acquired the team in 1989. He put in $90 million in cash, almost every dime he had, borrowed the rest, and put up everything he owned as collateral. Financing carried an 11.5% interest rate. That cost him about $40,000 a day, while the franchise was losing almost $1 million a month. Does that sound like conventional investing to you?
Jones bought the Cowboys in 1989 for about $140 million; some sources describe the broader transaction as roughly $150 million when summarizing the deal.
His own advisers thought the deal was insane. The purchase was “ridiculously overpriced” and “financial suicide,” according to Jack Dixon. Dixon was his adviser who warned that Jones could have gone “dead-dog broke.”
Everyone else viewed the NFL as a sports league, not a global media business.
Jones saw something different.
Most investors valued the team’s current earnings.
Jones valued its future control.
He immediately challenged every accepted rule:
He negotiated his own sponsorship deals instead of relying on league arrangements.
He transformed the stadium into advertising real estate.
He treated the Cowboys as an entertainment brand rather than only a football team.
He monetized intellectual property, licensing, premium seating, media, merchandising, and corporate partnerships.
Under his leadership, the Cowboys have won three Super Bowl titles. The Cowboys became one of the most valuable sports franchises in the world.
Let me give you the deeper principle: control beats cheapness. Most investors obsess over entry price because they have no ability to improve the asset. Jones knew he was buying control of a brand, a platform, and a cash machine he believed he could expand.
Average investors hunt bargains. Jones hunted monopolies. Pay attention to that single shift in thinking. This mindset works best for investors with long time horizons. And yes, you can build financial freedom. You can own scarce assets the market undervalues.
Jerry Jones owns the Bravo Eugenia. It’s a superyacht that is 358 feet (109 meters) long and reportedly cost around $225 million. She features luxurious amenities including a gym, spa, and two helipads. Oh, and the annual operating cost is only about $22 million.
I like you,
– Sean Allen Fenn
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