Last September, Dara Khosrowshahi sold 450,000 Uber shares for $43.7 million. This September he bought 141,000 back, at 27% below what he sold at.
You read this morning that Uber’s chief executive put $10 million of his own money into the stock on September 10. Tonight, let’s set that one filing against his five-year record.
Three questions I’ll answer
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How many times has Khosrowshahi bought Uber stock — and how many times has he sold? |
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What did he take for the shares he sold last September, and what did he pay this week? |
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Why does a record across time read differently from a single Form 4? |
I have watched executives buy their own stock for 25 years. The meaning is never in the one trade — it is in what came before it. ↓
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Three Buys, Nine Sells, and One Reversal
A Form 4 is the filing an executive must send the SEC within two business days of trading their own company’s stock. Khosrowshahi’s Uber record over the past five years holds twelve of them: three purchases, nine sales. That split is ordinary — executives are paid in stock and sell it to fund a life. What changed is the direction of the newest entry.
The Record
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Nov 7, 2024
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Adopts a Rule 10b5-1 selling plan — a schedule set in advance that takes the timing out of his hands. Modified June 13, 2025 to cover up to 650,000 shares through September 30, 2026.
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Sep 12, 2025
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Sells 300,000 shares at $94.34 to $95.92 — $28.6 million, under the plan.
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Sep 22, 2025
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Sells 150,000 shares near $100.48 — $15.1 million, under the plan. Direct holdings fall to 982,544.
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Sep 2, 2026
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Uber cuts about 3,300 jobs, 10% of staff.
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Sep 4, 2026
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President and COO Andrew Macdonald buys 70,000 shares at $75.23 to $76.85 — $5.3 million.
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Sep 10, 2026
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Khosrowshahi buys 141,000 shares at a weighted-average $70.96 — $10,005,952, transaction code P. Direct holdings: 1,367,100.
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The 2025 sales carry no read on his view of the price. A pre-arranged plan sets the dates ahead of time, so the seller does not pick the day. The September 10 purchase is the opposite kind of trade: open market, his own money, no plan behind it. He sold 450,000 shares last September at an average near $97 and bought this week at $70.96 — 27% lower — with the selling plan still open through the end of this month.
Where It Stands
The buy lifted his direct holdings 11.5%, to 1,367,100 shares — about $97 million at the price he paid, and still a fraction of one percent of a company valued near $148 billion. He is not the only one. Macdonald holds 426,320 shares after paying an average $75.83, above where his chief executive bought six days later. Earlier this year CFO Balaji Krishnamurthy purchased about 22,450 shares near $71.25. All three bought while Uber was cutting staff and pursuing a $14.8 billion takeover of Delivery Hero, the German food-delivery group, in an offer that runs to November 5.
One purchase is a headline. The record tells you whether it breaks form — and this one does. It is Khosrowshahi’s first open-market purchase of Uber stock in at least two years, set against nine sales, at a quarter below the prices he was taking as a seller.
NATE’S TAKE
I have learned to read the change in behavior rather than the size of the check. For a year Khosrowshahi was a scheduled seller of Uber near $100, and the plan that made him one is still running. Then he stepped to the other side and paid $70.96 in the open market, six days after cutting a tenth of the staff. That does not tell me the stock is cheap — executives are early as often as anyone else. It tells me the man who sees the numbers first has stopped being a seller, and that is a different sentence from the one his filings have been writing since 2024.
— Nate Fowler
After the Bell · Evening Special Edition
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