If you want to get a sense of Jesse Willms at his absolute peak—the wealth, the lifestyle, the aura of swaggering invincibility—then the weekend of November 12, 2010, is where we want to begin. That Friday afternoon, resplendent in a lustrous violet button-down, Willms packed half a dozen friends into a private plane on a frosty Edmonton, Alberta, tarmac and jetted off to Las Vegas. En route, Willms uncorked a bottle of Dom Pérignon and passed it around so everyone could take a swig. Then came the shooters: for the men, Jack Daniel’s; for the women—three leggy brunettes and a statuesque blonde—Smirnoff with Red Bull. Soon enough, off came Willms’s shirt, as often happened on festive occasions. After landing in Las Vegas, the group piled into a titanic silver limo and made for the Encore, where they checked into an $8,000-a-night, 5,829-square-foot duplex suite—a favorite haunt of Prince Harry. For the next two days, Willms and his entourage danced atop nightclub tables, shopped at Tiffany, went for thrill rides, and caught an Usher concert, all before flying back to Alberta in time for work on Monday morning.
Of course, for an ascendant young tycoon like Willms, a flashy weekend in Vegas hardly registered as a noteworthy event. In those days, Willms spent quite a few of his off hours celebrating in grand style—carousing at the Playboy Mansion, racing Formula One cars—and with good reason. At only 22, without even a high-school diploma to his name, Willms had forged himself into a veritable e-commerce titan, with footholds in online auctions, health products, data services, and more. His company Just Think Media may have been the most successful Internet venture no one had ever heard of: in 2009, with just 20 employees, it earned more than $100 million in revenue. Few entrepreneurs, past or present, have ever built such a lucrative company so young. Not even Mark Zuckerberg could match the achievement; in 2006, the year he turned 22, Facebook reportedly grossed just $48 million. Basking in the neon radiance of Vegas, his eyes steely and sure, Willms looked like a triumphant mogul poised for greater triumphs yet.