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Brendan Kennedy knew early on that his bet on marijuana would take years to pay off—if at all.

It’s “either career suicide or it’s the smartest decision we’ve ever made in our lives—and we won’t know for three to five years,” Kennedy told Bloomberg in 2012.

The windfall didn’t arrive for six years, but close enough. In July, Tilray Inc. became the first cannabis company to list its shares on a US exchange and rode a wave of investor hype to end 2018 with a 315% gain. That made Kennedy, its 47-year-old CEO, the second-highest-paid executive in 2018 among companies traded on US exchanges, according to the Bloomberg Pay Index.

Kennedy hasn’t previously been among the world’s top-paid managers. With Tilray, he joins an exclusive club of entrepreneurs whose gambles yielded compensation packages of a magnitude rarely seen at blue-chip companies. Examples include Snap Inc.’s Evan Spiegel, who was crowned the king of pay for 2017 with a half-billion-dollar package, and GoPro Inc.’s Nick Woodman, who led the list in 2014 with $284.5 million.

Like Kennedy, Spiegel and Woodman received big packages tied to their companies successfully launching initial public offerings. “IPO grants serve two purposes—alignment with shareholders and retention, because an executive disruption at that stage can be very problematic,” said Aalap Shah, managing director at Pearl Meyer, a consulting firm that specializes in executive compensation. “The thing for shareholders to question is diminishing returns. Is there a point where the IPO grant isn’t really worthwhile?”

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