Well apparently, February was spring cleaning at Airbnb HQ, and it has to make you wonder—do the insiders know something we don’t? In short, CEO Brian Chesky is leading what can only be described as a February fire sale, as he kicked things off by unloading $26.4 million in shares. Two days later—on Valentine's Day no less—he dumped another $14.2 million in fun coupons. 

(Source: Giphy) 

But, but, but… here's the thing, it wasn’t just the commander and chief flooding his bank account. CFO Elinor Mertz joined the party with a $4 million sale, CTO Aristotle Balogh got in on the action with a relatively modest $112,735 sale, and co-founder Joseph Gebbia decided $3 million worth of shares needed a new home too. Fast forward, and Chesky was back for more selling another half a milly in stock. 

Now of course, while this definitely raises some eyebrows—this is the same old Rule 10b5-1 story. Which is basically an insider's way of saying “I planned this mass exodus months ago, so legally, you can't accuse me of anything." However, even after this selling spree, Chesky still has 12.2 million shares plus more tucked away in trusts (a.k.a. just enough to maintain the appearance that he's still invested in the company's future.).

(Source: Giphy) 

Meanwhile, Wall Street analysts are hiking their price targets like Airbnb hikes its prices during Coachella. Benchmark raised its target to $178, mainly due to their recent Q4 earnings, while DA Davidson went to $170 but kept a "Neutral" rating. In other words, “I’m not saying you should buy it, but I”m definitely not saying you shouldn’t either.” 

In addition, Bernstein SocGen Group jumped to $185, calling Airbnb the "Amazon of travel"—presumably to keep Chesky on his good side. But even with that analyst optimism, you have to ask yourself—was this sale really planned, or is it the fact that Airbnb is absolutely bloated in valuation compared to its peers. For example, the “Amazon of Travel” is 40% more expensive than its competitors, while trading at 32.4x its 2026 earnings. Hilton, with its pristine lobbies and chocolates on pillows, trades at 32.05x. Expedia, meanwhile, is at 13.19x, looking like it's being sold at the discount bin at TJ Maxx.

(Source: Giphy) 

So yeah, when I say bloated—Airbnb is absolutely packing on the waistline. Which is why when a CEO and his ragtag team of executives sell $41 million worth of stock in a single month, what message does that send? Of course, the 10b5-1 says it’s planned, which is true, but with the stock down 12% over the past year, you have to wonder whether or not this is getting out before reality kicks the market in the teeth.

And when you look at what the market gave us on a silver platter yesterday, you can’t dismiss the fact that February was the perfect time to cash out with $40 million. Of course, only time will tell what will come of Airbnb going forward, but just remember the key of deciphering the business world is understanding: "Do as I do, not as I say in carefully crafted PR statements approved by legal." And right now, the only thing Airbnb executives are doing is selling. 

For now, keep your eyes on Airbnb and place your bets accordingly, friends. As always, stay safe and stay frosty! Until next time… 

Stocks.News does not hold positions in companies mentioned in the article.