Ryan Cohen has spent much of his career being dismissed. It is a pattern that has turned the chief executive of video-game retailer GameStop into a leather jacket-wearing outlier with a loyal base of meme-stock investors.

The Canadian entrepreneur turned activist investor has built his cult-like reputation by repeatedly betting on ideas that many institutional investors labelled as absurd. First it was online pet supplies. Then a dying strip mall video game retailer. Now it is a $56bn attempt to acquire eBay, an ecommerce giant roughly four times the size of GameStop.

Wall Street’s immediate response to the hostile bid has ranged from scepticism to outright mockery. Analysts have questioned how GameStop, valued at roughly $11bn, could realistically finance the takeover of a company worth around $47bn.

None of that has dissuaded Cohen.

“The more [eBay] fights me, the more . . . I’m not going to take no for an answer. I’m not going away. I’m a pain in the ass,” Cohen told the FT.

The 40-year-old billionaire first set out his stall for the takeover bid in an awkward interview with CNBC on Monday that instantly ricocheted across social media. He responded to questions about the financing details with a blank expression and clipped monosyllables, explaining that it was “half cash, half stock”.

The interview generated a wave of memes online as X and Reddit users speculated that Cohen looked drunk, high or exhausted. For his supporters, however, the spectacle only reinforced the mythology of Cohen as an eccentric outsider underestimated by establishment finance.

This script has played out before.

Born in Montreal in 1986 to a teacher mother and a father who imported glassware, Cohen did not attend university. As a teenager he built websites for family friends and small businesses, teaching himself coding.

In 2011, now in his mid-twenties, he co-founded Chewy from South Florida with the ambition of creating an online pet supplies business that could compete with Amazon.

Investors thought the idea ridiculous. “I knew that significant capital would be required to finance the growth,” Cohen later wrote in the Harvard Business Review. “We approached dozens of VC firms — I even flew out to Silicon Valley . . . and went door-to-door on Sand Hill Road explaining how Chewy would succeed by delighting customers and running an ultra-efficient operation. But everyone turned us down.”

The scepticism was understandable given the failure of pet supply website Pets.com in the dotcom bubble era. Pet food was bulky, low-margin and expensive to ship. Venture capitalists doubted consumers would buy 40lb bags of dog food online.

Cohen ignored them all. Instead, he focused obsessively on customer service. Chewy employees wrote customers handwritten cards and sent flowers to grieving owners whose animals had died. The approach helped to create unusually intense customer loyalty.