UBER is a much discussed stock in this forum. I recently noticed that UBER CEO bought $10 million $ worth of stock and the COO bought $5 million of stock near 52-week low. While insiders spent much of late 2025 and earlier this year trimming positions, the tone completely flipped in September 2026. CEO Dara Khosrowshahi put his own money where his mouth is, buying 141,000 shares on the open market at roughly $71 a share, a cool $10 million bet. Senior leadership also joined in, with another 70,000 shares picked up just days earlier. Heavy open-market CEO buying near 52-week lows is one of the clearest votes of confidence an investor can get.
Uber spent years as the poster child for burning venture capital cash, but the business today looks completely different. Trading right around $71 a share, down roughly 9% over the past month and flirting with its one-year lows, Uber is quietly printing real cash. Looking through the latest financial report, the company churned out over $10 billion in free cash flow over the trailing twelve months on more than $55 billion in revenue. That means you are looking at a business trading around 15 times earnings and free cash flow, which is surprisingly cheap for a tech platform with high-single to double-digit top-line growth and dominating market share across ride-hailing and food delivery.
What has been dragging the stock down lately comes down to the big existential question: autonomous vehicles. Retail investors and Wall Street alike have been worried that robotaxis will displace traditional rideshare networks or that companies with proprietary fleets will bypass Uber entirely. On top of that, top-line growth has naturally slowed from hyper-growth to the low teens, with Q2 2026 revenue up about 12% year-over-year. Margins have also faced pressure as Uber pours heavy capital into autonomy partnerships, international delivery deals, and restructuring.
Yet the street may be missing how well-positioned Uber's network actually is. Instead of building expensive robotaxis from scratch, Uber is turning into the aggregator of choice. Just recently, they rolled out commercial autonomous ride-hailing pilots in London with Wayve, locked down permits in Spain with WeRide, and went live with Baidu’s Apollo Go in Dubai. Whether a car is driven by a gig worker or a computer, riders already have the Uber app on their home screen, giving Uber massive distribution power that fleet builders will struggle to replicate without huge customer acquisition costs.
Uber has transformed from a cash furnace into a mature, disciplined platform with solid financial strength and a growing buyback program. If the market continues to treat the autonomous shift as an Uber-killer rather than an eventual margin tailwind, the disconnect between Uber's valuation and its underlying cash machine looks like an intriguing window for patient retail investors.