GameStop CEO Buys US$22.8m in Stock He Calls a Mistake

GameStop's chairman, president and chief executive Ryan Cohen has a peculiar way of treating his self-proclaimed failures – he keeps investing tens of millions of dollars in them.

A regulatory filing published on Tuesday revealed Ryan purchased 844,130 shares of the struggling videogame retailer for approximately US$22.8m.

The transaction is his second of the month. A US$17.1m acquisition disclosed on 2 October brings his total October spending to nearly US$40m, with both trades executed at prices near the stock's 52-week high of US$27.53.

Two purchases, one month, one contradiction

What makes the timing striking is what came next. Shortly after the filing was made public, Ryan appeared on stage at the Silvia Investor Summit in New York, where investor Anthony Pompliano asked him to reflect on a mistake that shaped him – and he nominated GameStop.

Ryan acknowledged that the outcome of his GameStop involvement had never matched his original vision when he first put money into the then-struggling retailer.

"I've made a lot of mistakes, but when I end up in a situation like taking over GameStop, failure wasn't an option," he said.

When burning the boats becomes the strategy

Ryan's reasoning is that eliminating the possibility of retreat is itself the engine of performance, because people with nowhere to go solve problems with an urgency that those operating with safety nets rarely match.

He admitted that he would subconsciously put himself in difficult situations, but added "that's when you get the best results in life".

It is a philosophy with a credible track record. Ryan's Forbes-estimated fortune of US$5.2bn traces back to Chewy, the online pet retailer he co-founded in 2011 and scaled to US$3.5bn in annual revenue before PetSmart acquired it for US$3.4bn in 2017.

He entered GameStop in late 2020, putting in roughly US$76m for a 13% stake, joined the board in January 2021 as Reddit traders drove the stock to extraordinary heights, and eventually accepted the CEO role he had never sought.

GTA VI, eBay and what comes next

Regardless of how the eBay situation resolves, a more immediate catalyst sits firmly on the calendar. Grand Theft Auto VI is due on 19 November following its second delay, a launch widely anticipated to be the largest in the history of the medium and precisely the kind of store-traffic event GameStop was built for.

The complication is that the game ships without a disc, redirecting any commercial upside toward consoles, accessories and trade-ins rather than physical copies at the register.

On the eBay front, GameStop made a bid of roughly US$56bn earlier this year – approximately four times its own market value – only to be rejected in notably blunt terms, with eBay characterising the offer as not credible and unattractive.

Bloomberg reported in August that Ryan was considering stepping back from the acquisition in favour of a partnership or joint venture with the ecommerce company, and he has offered no public statement on the matter since.

For now, the clearest signal remains the regulatory filing itself, where a billionaire who openly labels GameStop a mistake has spent nearly US$40m in two weeks making it a considerably larger one.

GameStop's key partners:

Nintendo: GameStop relies heavily on vendor partnerships for hardware and software inventory, with Nintendo serving as one of its top commercial partners.
CEO: Shuntaro Furukawa | Headquarters: Kyoto, Japan

Sony Interactive Entertainment: Sony remains a vital key vendor for GameStop, supplying PlayStation consoles, games, and accessories that drive the retailer's core revenue.
CEO: Hideaki Nishino and Hermen Hulst | Headquarters: San Mateo, California, US

Microsoft: GameStop established a multiyear strategic deal with Microsoft to power its cloud infrastructure, back-office operations, and in-store enterprise tools.
CEO: Satya Nadella | Headquarters: Redmond, Washington, US