“I’ve been quietly keeping an eye on real-world asset tokenization for a while now,” the account wrote in the now-deleted series of tweets. “Most of it is noise. But underneath the noise, something real is happening.”

Chesky is an active user of X, where he routinely shares product updates, earnings commentary, and lessons from building Airbnb with his more than 1.2 million followers. He’s even used the platform to crowdsource suggestions for business improvements, such as lowering cleaning fees and, ironically, crypto payments, which earned praise from X owner Elon Musk. “This kind of interaction with users is awesome,” Musk wrote in response to the 2023 call for ideas, urging other companies to take note. Commentary from Chesky on crypto is out of character for his accounts. 

This week, though, Chesky’s replies were filled with accusations of “AI slop,” a term that describes low-quality content produced by artificial intelligence.  

Users pointed out aspects of the Chesky “tokenization” post that suggested it had been cooked up by AI. “One thing that really makes AI writing distinct is the lack [of] commas,” Bloomberg’s Joseph Weisenthal wrote. 

Communications strategist and Rostra founder Lulu Cheng Meservey, meanwhile, warned that “CEOs damage trust when they post unfiltered claudeslop.” 

When Fortune analyzed Chesky’s thread through AI-detection tool Pangram, the system flagged it as 100% AI-generated. The posts have since been deleted. Airbnb declined to provide a public comment. 

The thread appeared as a reply to a user referencing Robinhood CEO Vlad Tenev’s recent interview with CNBC, in which he discussed the growing market for tokenized real-world assets.

The hacked posts were flagged to X and escalated to platform security teams as a “high-profile compromise,” according to correspondence between Airbnb and X employees reviewed by Fortune. X secured the account on Tuesday evening, and Chesky was then able to regain access to his account. 

The rise of AI slop

Chesky has previously praised the use of artificial intelligence, telling CNBC in February that the tech “is the best thing that ever happened to Airbnb.” The serial founder is also preparing to launch a new AI lab focused on building new models, according to Bloomberg. 

But the surge of low-quality AI-generated content is becoming a bigger headache for both business leaders and creatives, and the volume of mediocre images, videos, and text has grown so overwhelming that Merriam-Webster named “slop” its 2025 word of the year. A new analysis by AI detection platform Pangram found that roughly one in four long-form social media posts are now AI-generated. Nearly half of X’s longer “Articles” contain AI-written material.

Leaders across industries are concerned. Substack CEO Chris Best warned in September that AI could clog already crowded feeds with low-quality content and strain an attention economy he referred to as a “scarce resource.” YouTube CEO Neal Mohan dedicated a section of his annual letter to “managing AI slop,” declaring it a top priority for 2026. Oscar-winning director Christoper Nolan told The Telegraph this week that Gen Zers are “utterly rejecting” AI slop with reactions that are “immediate and harsh.”

“They see it for what it is very quickly,” The Odyssey director said. “It’s much easier for them to identify it, because it grew out of an online world they know really well.”

A recent report from social media management platform Sprout Social found that 56% of respondents say they encounter “AI slop” on social media often or very often, and 83% say they see it at least sometimes. Gen Z is more likely to rebuff the content, too. Half of respondents said they have unfollowed, muted, or blocked accounts if the content felt like AI slop.

Fortune 500 CEO security 

Chesky is not the first Fortune 500 CEO to have a social media account compromised. 

In 2016, Meta founder Mark Zuckerberg’s Twitter, LinkedIn, and Pinterest accounts were briefly compromised by a group called OurMine Team.

“Hey @finkd (Mark Zuckerberg’s Twitter handle) we got access to your Twitter & Instagram & Pinterest, we are just testing your security, please dm (direct message) us,” the now-deleted post read. 

In 2019, Twitter founder Jack Dorsey’s account was briefly taken over for 20 minutes, an action that led to the platform to permanently disable its “text-to-tweet” (SMS) feature.

Boeing (BA 1.02%) delivered 64 jets in June, four more jets than it delivered in May and the same month last year. The number is part of the company’s 314 jet deliveries in the first half of 2026. Its commercial delivery performance is a good sign of its financial recovery. Pushing out this volume of airline jets has a massive, direct impact on the company’s free cash flow (FCF) trajectory.

While Boeing’s overall operating margin remains lean (only 18.1% in the first quarter) as it navigates program overruns and defense drags, deliveries are the raw fuel for its balance sheet. A strong June demonstrates the manufacturing discipline required to chip away at its post-pandemic debt and secure sustainable, positive FCF.

Here is a breakdown of what these delivery numbers mean for Boeing’s cash position moving forward.

Boeing is unlocking sunk inventory

The cash flow cycle is highly back-end loaded in aerospace manufacturing. Predelivery payments are generally around 30% of the purchase price, so manufacturers pay for much of the parts, labor, and supply chain overhead long before the plane leaves the tarmac. When the keys are actually handed over to the customer, the remaining 70% of the plane’s total purchase price is collected.

Pushing 64 jets out the door in a single month means Boeing is successfully liquidating parked, fully built inventory and turning it into immediate cash. In the first quarter, it reported an earnings per share (EPS) loss of $0.11, and even that was a 31% improvement year over year.

Validating its free cash flow target

In the company’s first-quarter earnings call, Boeing chief financial officer Jay Malave projected full-year 2026 FCF to finish between $1 billion and $3 billion. That’s a big change from the $1.5 billion FCF loss in the first quarter, as the first half of the year saw heavy operational expenditures and narrower operating margins.

Strong June momentum serves as proof of concept for the Street, validating that the era of aggressive cash burn is fading and that the $1 billion to $3 billion FCF target is highly achievable if execution remains steady. The company had consecutive positive FCF quarters in the second half of 2025.

Malave said that because of cash outflows in the first half of the year, achieving the full-year FCF target depends on a back-end-loaded second half, driven heavily by increased delivery volumes. As it is, Boeing booked a net total of ⁠113 new orders in June and a total of 408 new orders this year.

Today’s Change

(-1.02%) $-2.22

Current Price

$215.90

Key Data Points

Market Cap

$172BMarket cap calculated using publicly traded shares outstanding only. Does not include unlisted, private, or dual-class non-traded shares. Implied market cap may vary.

Day’s Range

$214.39 – $217.74

52wk Range

$176.77 – $254.35

Volume

74.9K

Avg Vol

6.5M

Gross Margin

4.83%

Supply chain and delivery health are improving

Investors are still playing a wait-and-see game with Boeing, as its shares are flat so far this year.

To generate robust, multibillion-dollar FCF plateaus in the coming years, Boeing needs volume stability. June’s delivery numbers (which included 42 of the workhorse 737 MAX models) provide a critical insight into its operations. Delivering at this rate demonstrates that major supply chain and parts delays are no longer the absolute ceiling they were in previous quarters.

This operational rhythm sets the stage for Boeing’s upcoming push to lift 737 production from 42 to 47 aircraft per month, now that the Federal Aviation Administration (FAA) has approved that change. A synchronized supply chain executing higher monthly production rates is the primary structural driver that will expand program-level cash margins moving forward.