Top Billionaire Tech Insiders Shed Billions in 2025 Sell-Off

July 1 - Oracle ORCL Chief Executive Safra Catz led U.S. insider selling in the second quarter, disposing of $1.83 billion of stock.

Her sales, executed under a predetermined trading plan. In the first half of 2025, Catz offloaded roughly $2.5 billion in company stock, surpassing other top sellers.

Dell Technologies DELL CEO Michael Dell (Trades, Portfolio) followed, selling $1.22 billion of shares, while Amazon AMZN founder Jeff Bezos cashed out $737 million, his first disposals of the year under a new trading arrangement.

Other notable transactions included Roblox RBLX CEO David Baszucki's $631 million sale, Nutanix's Max de Groen offloading $421 million, and Blue Owl Capital OWL co-president Michael Rees' $396 million in share disposals.

AppLovin APP director Herald Chen sold $341 million, and NVIDIA NVDA board member Mark Stevens added $288 million to insider sales. CVS Health CVS board member Larry Robbins (Trades, Portfolio) rounded out the top ten, selling $254 million.

Overall, insider sales in Q2 totaled $36 billion across 6,000 filings, down from $62 billion in the year-ago quarter. Insider trends suggest executives are capitalizing on high valuations amid mixed market signals.