Cohen and Khosrowshahi Put Fresh Cash Behind Their Stocks

Ryan Cohen committed roughly $20.4 million to GameStop on September 10, buying 1 million shares at a weighted average price of $20.3759. The same day, Uber CEO Dara Khosrowshahi spent about $10 million on 141,000 shares at $70.9642.

These were not compensation awards or option exercises. Both filings used transaction code P, which denotes an open-market purchase, and neither filing marked the box for a Rule 10b5-1 trading plan. In other words, the disclosures point to deliberate buying rather than a previously scheduled transaction.

Cohen’s purchase reinforces his already large economic stake in GameStop. After the transaction, his direct ownership rose to 39.35 million shares, according to the SEC filing. The timing also followed a quarter in which GameStop’s collectibles business became the clearest engine of the company’s operating improvement.

Collectibles revenue jumped 57% year over year to $356.3 million in the fiscal second quarter, while adjusted EBITDA more than doubled to $174 million. GameStop raised its full-year adjusted EBITDA outlook to more than $650 million, up from a previous target above $600 million. The catch is that the broader retail operation remains under pressure, leaving investors to decide how much value belongs to the newer collectibles strategy.

Khosrowshahi’s purchase sends a different signal. Uber shares had been weakened by concerns that autonomous vehicles and robotaxis could eventually erode the company’s advantage in mobility. Yet the underlying platform continues to expand. Second-quarter gross bookings rose 24% to $58 billion, trips climbed 18% to 3.9 billion, and adjusted EBITDA increased 33% to $2.8 billion. Uber guided to third-quarter non-GAAP EPS of 84 to 88 cents.

That makes the insider buying notable, but not conclusive. Cohen is backing a sharp strategic pivot at a company where sentiment remains unusually volatile. Khosrowshahi is buying into a profitable platform whose growth story is being discounted against a longer-term technological threat.

Insider purchases can reveal conviction. They do not eliminate execution risk, valuation risk or competition. For shareholders, the more useful question is whether GameStop can turn collectibles momentum into a durable business and whether Uber can keep compounding before autonomous transport changes the economics of its core market.