Brian Chesky

Brian Chesky (CEO) sold 30,743 shares for $4,254,778.94 on 2026-06-15 via pre-arranged 10b5-1 plan

CEO Brian Chesky executed 5 separate sales totaling 30,743 shares for $4,254,778.94 at blended average price of $138.40 on 2026-06-15. This transaction is part of a pre-arranged 10b5-1 trading plan adopted on 2026-02-26, meaning the sale was scheduled rather than discretionary. Post-transaction holdings stand at 10,701,685 shares, representing a -0.3% net change from pre-transaction holdings of 10,732,428 shares. Chesky has executed 5 prior sells at ABNB within the recent trading window (2026-06-05 through 2026-06-09), though outcome measurement on those trades is not yet available. The current stock price of $140.54 is -4.6% from the 52-week high of $147.25, while the 30-day change shows +4.6%.

CEO Brian Chesky sells 41,899 shares for $5.7M under pre-arranged 10b5-1 plan; holds 10.73M shares post-sale

Brian Chesky executed 4 separate sales totaling 41,899 shares for $5,672,126.65 on 2026-06-08 and 2026-06-09 at an average price of $135.38 per share. The sales were conducted under a pre-arranged 10b5-1 trading plan adopted on 2026-02-26, meaning the transactions were scheduled and non-discretionary. Chesky retained 10,732,428 shares post-transaction, representing a 0.4% reduction in holdings. The current stock price of $129.10 is 12.3% below the 52-week high of $147.25 and 5.8% lower than 30 days ago, providing context on recent price momentum at the time of these scheduled sales.

CEO Brian Chesky sold 80,848 shares for $10,990,333.91 via scheduled 10b5-1 plan on 2026-06-04 and 2026-06-05

Brian Chesky executed 4 separate sales totaling 80,848 shares for $10,990,333.91 at blended average price of $135.94. This transaction is part of a pre-arranged 10b5-1 trading plan adopted on 2026-02-26, meaning it was scheduled and not discretionary. The CEO retained 10,774,327 shares post-transaction, representing a -0.7% reduction from prior holdings of 10,855,175 shares. Current price of $134.43 is -8.7% from the 52-week high of $147.25, and his trading prices ($135.72–$137.07 across the sales) were near the current level. His prior 5 trades at ABNB show mixed near-term returns (ranging -1.6% to +0.7% at 30 and 90 days), while his cross-ticker track record across 20 prior sells averaged -1.2% at both 30 and 90 days.

CEO Brian Chesky sells 62,764 shares for $8.4M via scheduled 10b5-1 plan on 2026-06-02

Brian Chesky (CEO and Chairman) executed four separate sales on 2026-06-02 totaling 62,764 shares for $8,410,584.04 under a pre-arranged 10b5-1 trading plan adopted on 2026-02-26, reducing his holdings from 10.92M shares to 10.86M shares (-0.6%). The transaction is scheduled rather than discretionary, so it does not reflect real-time conviction signals. Across his same-ticker history at ABNB, prior sales show mixed post-transaction performance: 30-day returns ranging from -3.4% to +7.0%, and 90-day returns from -11.3% to -1.9%, offering no clear pattern of outsized timing skill. The stock is currently trading at $133.72, approximately 9.2% below its 52-week high of $147.25, and has declined 4.3% over the prior 30 days.

CEO Brian Chesky sold 308,450 shares for $41,751,141.10 under pre-arranged 10b5-1 plan on 2026-05-29 and 2026-06-01.

Brian Chesky executed 16 separate sales totaling 308,450 shares for $41,751,141.10 at a blended average price of $135.36 over two trading days, reducing his post-transaction holdings to 5,854 shares (-98.1% vs pre-transaction). This transaction is part of a pre-arranged 10b5-1 trading plan adopted on 2026-02-26, meaning it was scheduled rather than discretionary. Against Airbnb's current price of $134.35 and strong fundamentals (revenue $2,678,000,000.00, net income $160,000,000.00, +10.3% annual revenue growth), the near-complete liquidation of the CEO's position warrants investor attention despite its scheduled nature. The prior five trades at ABNB show mixed near-term outcomes (30-day range of -3.4% to +7.0%), providing limited directional precedent for this substantially larger transaction.

CEO Brian Chesky sold 515,296 shares for $68,365,968.73 via 10b5-1 plan on 2026-05-27 to 2026-05-28

CEO Brian Chesky executed 13 separate sales totaling 515,296 shares for $68,365,968.73 (blended average $132.67) across two trading days under a pre-arranged 10b5-1 trading plan adopted 2026-02-26, representing a 4.4% reduction in his holdings to 11,206,389 shares. Because this transaction is scheduled under a 10b5-1 plan rather than discretionary, it reflects automatic execution aligned with a predetermined timeline established months prior, not a signal timed to current market conditions. His prior Airbnb sales (5 trades in 2025) showed mixed near-term results: three posted 30-day gains while one declined, and 90-day returns ranged from -1.9% to -11.3%, providing limited directional clarity. The current stock price of $133.31 sits 9.5% below the 52-week high and has declined 5.0% over 30 days, while the company posted 10.3% annual revenue growth and net income of $160,000,000 on $2,678,000,000 quarterly revenue, establishing baseline operational stability.

CEO Brian Chesky sells 60,000 ABNB shares for $7.9M across 4 trades; prior ABNB sales consistently underperformed 90-day forward returns.

Brian Chesky, Airbnb's CEO and Chairman, executed 4 separate sales totaling 60,000 shares for $7,861,124.47 at blended average price $131.02 between December 12–15, 2025, reducing his holdings by -56.7% to 45,854 shares post-transaction. His prior trades at Airbnb show a consistent pattern: 5 of 5 earlier sales were well-timed at the 90-day mark, with returns ranging from -12.5% to -11.3% over that interval. The current stock price of $132.01 is -18.2% from the 52-week high of $161.42, and the 30-day and 90-day price moves have been positive (+8.2% and +7.2% respectively), suggesting recent momentum. Chesky's timing history at this ticker—100% successful under the 90-day lens in 5 prior instances—may be worth monitoring if post-transaction returns diverge from that pattern.

CEO Chesky sells 16,500 ABNB shares for $2.3M across 8 transactions on 2025-06-06, reducing stake by 33.5% to 32.8K shares

Brian Chesky (CEO and Chairman) executed 8 separate sales on June 6, 2025, totaling 16,500 shares for $2,329,644.42 at a blended average price of $141.19, reducing his holdings from 49,300 to 32.8K shares—a 33.5% reduction. The sales occurred across a narrow price range ($140.45–$143.35), suggesting a single-day liquidation event. Across his open-market history on all tickers, his prior 20 sells had an average 90-day return of -12.5% with a 100.00% well-timed rate, indicating his past sales have historically preceded stock declines. At ABNB specifically, his 5 prior trades show recent sells on 2025-05-29 (outcome not yet measurable) and on 2025-04-01 with modest positive 30-day returns (+3.0% and +2.4%), though no 90-day outcomes are measurable yet at this ticker. The current price is $138.56, down 14.2% from the 52-week high of $161.42 but still within recent context of a 30-day +9.1% and 90-day +9.5% return. The scale of this sale—one-third of holdings disposed in a single day—warrants attention as a significant transaction from the company's leader.

CEO Chesky sells 8,000 ABNB shares in 3 transactions for $1,026,676.24; post-sale stake remains 40,800 shares

Brian Chesky executed 3 separate sales totaling 8,000 shares for $1,026,676.24 on 2025-05-29 at prices ranging from $127.84 to $129.38, reducing his holdings by 16.4% to 40,800 shares. His cross-ticker track record shows 20 prior sells with a 100.00% well-timed rate at the 90-day mark (average 90d return -13.1%), but his same-ticker history at ABNB shows 0 of 0 prior sells well-timed at 90 days. The stock has declined 8.3% over the past 90 days and is currently 19.7% below its 52-week high, though the stock posted +3.5% in the last 30 days. This filing reflects a material reduction in CEO stake but does not constitute a directional signal absent disclosure of motive or scheduling details.

Airbnb CEO Brian Chesky sells 38,459 shares for $4.6M on April 1, holding 11.73M shares post-sale

Brian Chesky, CEO and Chairman, executed 2 separate sales totaling 38,459 shares for $4,631,912.83 at prices of $120.34 and $121.12 on 2025-04-01, reducing his holdings by 0.3% to 11.73M shares. The blended average sale price of $120.44 is currently 5.7% above the market price of $113.97, which is down 31.1% from the 52-week high of $165.42. His cross-ticker track record shows 20 prior sells with an average 30-day return of -18.6%, though his prior ABNB-specific trades (5 recent transactions, 4 from March 17 with outcomes not yet measurable, 1 from March 3 with a -14.0% 30-day return) do not provide sufficient data for a timing pattern assessment. Airbnb's fundamentals remain solid with $3.7B quarterly revenue, $1.4B net income, and 12.0% annual revenue growth, providing context for the relatively small scale of this disposition.