In The Beautiful and Damned, F. Scott Fitzgerald’s second novel, young Anthony and Gloria Patch find their “opalescent dreams of future pleasure” dissolving as their fortune shrinks.

The situation is partly circumstantial, but predominantly self-inflicted. In a period of post–World War I inflation, the Patches are living above their means on income from Anthony’s bonds and other investments. Anthony wishes to be “gracefully idle” as he and Gloria wait for his wealthy grandfather to die. He is therefore unwilling to take employment.

He believes, you see, that “traits which we call fine—courage and honor and beauty and all of that sort of thing—can best be developed in a favorable environment.” He fancies that he might become a great writer, and at times he writes. More often, he stumbles from one drunken fiasco to another, “and every other month they sold a bond, yet when the bills were paid it left only enough to be gulped down hungrily by their current expenses.”

At one point, the Patches allow their inability to afford a gray squirrel coat for Gloria to stand as a totem of their financial anxieties. To cheer themselves up, they hold a “prolonged, hysterical party.” Gloria’s “heart was very bitter” after realizing that the price of the party was “twice what the gray squirrel coat would have cost.”

It’s a cliché that no one feels quite as poor as a multimillionaire down to his last million, but anyone whose personal worth has risen and then plummeted knows something of Gloria’s dismay. So do countless people who’ve felt the wind hit the sails—the exhilaration of possibility—just before the hull hit the rocks. Certainly Stu Utgaard, the subject of this month’s feature story by Jack Gordon, knows this feeling.

Utgaard is no Anthony Patch. No one could fault his work ethic or claim that he lacked ambition. He grew up in a farmhouse, earned two degrees, learned the mergers-and-acquisitions business, started his own M&A brokerage, and became one of the nation’s top dealmakers—at the same time that he grew his family’s poultry hatchery twentyfold and personally spent every Sunday washing hatchery equipment, boxing chicks, and sending out invoices.

Then, in 1996, he bought a 36-employee retail business that he renamed Sportsman’s Warehouse. In the next three years, he doubled the company’s sales. By 2004, the company had 30 stores and revenues of $293 million; by 2009, 67 stores and revenues of $718 million. There was also a company Learjet 60 and some $464 million in debt owed to a variety of creditors, in large part because of Utgaard’s talent for securing financing. Meanwhile, sales had dived in the recessionary second half of 2008.