Craigslist founder Craig Newmark is pouring millions of dollars into combating AI’s dark side
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2 years agoon
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Craig Newmark, founder of Craigslist
Source: Bleacher + Everard
Craig Newmark made his fortune off a website, founded in 1995, that served as an early online bulletin board and looks like it hasn’t been updated in two decades.
That website, Craigslist, is still cranking along, featuring apartment listings, an active jobs board and items for sale. But the privately held company has long been surpassed in value by the likes of Airbnb, LinkedIn and Facebook Marketplace, which all face Wall Street’s demands for growth and profit.
Though Newmark’s internet company may be outdated, his concerns about where the industry is headed are most certainly not. Since the 2015 debut of Craig Newmark Philanthropies, the entrepreneur has donated many millions of dollars to various causes involving media and technology.
Most recently, his organization contributed $3 million to help fund a new artificial intelligence and education initiative from Common Sense Media, the nonprofit told CNBC this week.
“While I tried to pay some attention to what was going on, just everything caught me by surprise,” Newmark said, referring to the current boom of generative AI and all the new and intelligent chatbots.
Newmark, 70, spoke to CNBC as he was recovering from a minor heart procedure he went through in late August. The heart ablation required Newmark to lay on his back “the whole time in the wrong position” and he “woke up with a lot of back pain,” he said.
More than the surgery, Newmark wanted to talk about the hospital food.
“Hospital pudding is really good,” he said. “And since they served my lunch cold, I asked them and got more containers of pudding.”
Newmark, who ran his business out of San Francisco but now lives with his wife in New York, said the hospital stay didn’t cause him to reflect much on mortality, as he’d already addressed such existential issues when he decided to simplify his life by giving away much of his Craigslist riches.

Newmark’s foundation has principally focused on donating to organizations and causes pertaining to journalism, combating misinformation, countering online harassment, cybersecurity issues, and supporting veterans and military families.
The rapid evolution of AI and its potential hazards have recently caught Newmark’s attention, and his money.
The goal of Common Sense’s AI project is to provide an AI ratings system for parents, educators, policymakers and regulators so they can evaluate what makes certain tools like OpenAI’s ChatGPT safe or unsafe for children. Additionally, the nonprofit is offering online AI literacy courses intended to help parents and educators teach basic AI fundamentals to children.
The full scope of AI’s capabilities and potential for societal harm became more clear to Newmark by the time companies began “modifying search engines to use generative AI.”
“I realized that if a search engine was using sources that weren’t reliable, if the sources were about lying to people, that would create a big, ethical problem, and you really don’t want a news source of any sort to knowingly lie,” Newmark said.
Newmark is concerned that bad actors will use generative AI to more easily amplify and spread disinformation. At the same time, he’s worried that tech companies, particularly in social media, “aren’t even trying anymore to get rid of stuff they know is dishonest,” he said.
Tech companies like Meta, Amazon and X (formerly known as Twitter) recently laid off numerous trust and safety workers as part of major cost-cutting initiatives, but have said that the downsizing won’t affect the safety of their platforms.
‘Bad uses’ of the internet
Meanwhile, AI has the potential to profoundly affect society, like the internet and the printing press before it, Newmark said. That’s an area where he has notable expertise. Craigslist was both hugely disruptive to newspapers and their classified ads sections, and has been a site that’s attracted criminals and scammers.
Few people predicted the “bad uses” of the internet, which has allowed nefarious actors to “mostly lie to people in large numbers,” Newmark said.
“I guess the profits to be made in being a really good professional liar, those profits have greatly increased because the internet is a big amplifier,” Newmark said. “It’s everyone’s printing press, and you get to use it as a printing press, whether your intentions are good or bad.”
Newmark said he became interested in language-generating software like ChatGPT in the early 1970s, “when people were beginning to talk about language understanding and neural networks.” However, he says, “I didn’t really understand it.”
Now the technology is here and spreading rapidly.

Newmark said he doesn’t want to name names when it comes to the organizations he fears are creating the most societal discontent through AI, because he’s previously been scarred for getting that specific.
“In the past when I’ve pointed out major problems, I’ve learned the hard way that I’m no match for someone who lies for a living,” Newmark said. “So, I’m allowing myself to be chickens—.”
Rather, he said he relies on “people who are both braver and smarter” to call public attention to those matters.
“Protecting kids when it comes to AI is a big issue,” Newmark said, regarding his donation to Common Sense Media. “I have no idea how I would go about getting started, but I know where to put my money where my mouth is.”
Why Common Sense?
“A lot of groups and politicians talk about protecting kids,” Newmark said. “But these guys are the real deal, and so I’m helping them.”
Misinformation and journalism
Newmark acknowledged that the topics of misinformation, journalism and content moderation have become more polarized and politicized of late. House Judiciary Chair Jim Jordan, R-Ohio, alleged that tech companies unfairly censor conservative speech, and he’s undertaken a “censorship investigation” to probe suspected ties between the executive branch and certain technologists and researchers.
Several academics previously told CNBC that the politicized landscape has led to some organizations cutting back on funding research into combating misinformation for fear of being publicly criticized.
“Some people are backing off, some people are getting braver. Again, I’m not very brave,” Newmark said. He highlighted the Knight Foundation and Ford Foundation as organizations that are “doing brave things.”
Within journalism, Newmark’s most high-profile endeavor is the City University of New York’s Craig Newmark Graduate School in Journalism. The program was renamed in 2018 after Newmark endowed the school with a $20 million gift, though he made prior contributions in 2016 and 2017.
He also donated $20 million in 2018 to help fund The Markup, which describes itself as a “nonprofit newsroom that investigates how powerful institutions are using technology to change our society.” That project quickly became controversial after founding Editor-in-Chief Julia Angwin said she’d been fired over email by co-founder and Executive Director Sue Gardner.
Still, Newmark says both the CUNY journalism school and The Markup have been successful, while other efforts “have not been successful, and I’m being discreet about them because I’m still trying to help before I have much sterner talks.”
He pegs his philanthropy success rate at “70% or 80%, which is good, but it’s not 100.”
In terms of where he spends his time online, Newmark said he still posts on X, primarily to promote and highlight the work of teachers. However, he said the site is losing its effectiveness as it leans toward showing people algorithmically recommended posts.
Thilina Kaluthotage | Nurphoto | Getty Images
“As a social network, Twitter does seem to be gone,” Newmark said, adding that he’s trying out rivals like Bluesky, Mastodon and Meta’s Threads.
In particular, Newmark said he likes “like the spirit of Mastodon and Bluesky,” which he likened to the early days of the internet when it took a long time for websites to build devoted audiences.
“The audience development is very slow,” Newmark said. “Twitter and everything else grew slowly and the other sites are growing slowly, and yet we are impatient and we want to see network effects now.”
Cybersecurity is another area of focus for Newmark. He pointed to a recent $100 million commitment announced in March to a collection of organizations working on cyber-related issues, like combating the spread of ransomware and creating methods for tech and security companies to share threat information.
He said the total number will probably exceed $100 million, because he’s already “broken through $80 million.”
In June, Newmark’s philanthropy arm also pledged to donate $100 million to multiple organizations supporting veterans and military members, who “sometimes have to choose between decent housing or feeding their families,” Newmark said. He called the treatment of that community “a national security matter.”
“There’s nothing virtuous in that,” Newmark said about his donations, noting that he doesn’t spend his money on “yachts or fast cars.”
“It’s more satisfying to give it away,” Newmark said. “Again, that’s not pious or altruistic. It’s just what I was taught in Sunday school.”
WATCH: How Amazon is racing to catch up in generative AI with custom AWS chips

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Technology
Waymo resumes robotaxi service in San Francisco after blackout chaos — Musk says Tesla car service unaffected
Published
3 hours agoon
December 22, 2025By
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Alphabet-owned Waymo has resumed its driverless ride-hail service in the San Francisco Bay Area after a temporary pause during blackouts that plagued the city beginning on Saturday afternoon.
“Yesterday’s power outage was a widespread event that caused gridlock across San Francisco, with non-functioning traffic signals and transit disruptions,” a Waymo spokesperson, Suzanne Philion, told CNBC in an e-mailed statement Sunday afternoon.
“While the failure of the utility infrastructure was significant, we are committed to ensuring our technology adjusts to traffic flow during such events,” she added.
Waymo notice of service outage in San Francisco.
Source: Waymo
As power outages spread yesterday, videos shared on social media appeared to show multiple Waymo vehicles stalled in traffic in different parts of the city.
San Francisco resident Matt Schoolfield said he saw at least three Waymo autonomous vehicles stopped in traffic Saturday around 9:45 p.m. local time, including one he photographed on Turk Boulevard near Parker Avenue.
“They were just stopping in the middle of the street,” Schoolfield said.
A Waymo vehicle stuck between Parker and Beaumont, on the north side of Turk Boulevard in San Francisco.
Credit: Matt Schoolfield
The power outages began around 1:09 p.m. Saturday and peaked roughly two hours later, affecting about 130,000 customers, according to Pacific Gas and Electric. As of Sunday morning, about 21,000 customers remained without power, mainly in the Presidio, the Richmond District, Golden Gate Park and parts of downtown San Francisco.
PG&E said the outage was caused by a fire at a substation that resulted in “significant and extensive” damage, and said it could not yet provide a precise timeline for full restoration.
San Francisco Mayor Daniel Lurie said in a 9 p.m. update on X that police officers, fire crews, parking control officers and city ambassadors were deployed across affected neighborhoods.
Waymo’s Philion also told CNBC that “While the Waymo Driver is designed to treat non-functional signals as four-way stops, the sheer scale of the outage led to instances where vehicles remained stationary longer than usual to confirm the state of the affected intersections. This contributed to traffic friction during the height of the congestion.”
Waymo “closely coordinated with San Francisco city officials,” she said, and proactively paused its service as of Saturday evening and in the first half of the day on Sunday.
“The majority of active trips were successfully completed before vehicles were safely returned to depots or pulled over,” she noted.
Amid the disruption, Tesla CEO Elon Musk posted on X: “Tesla Robotaxis were unaffected by the SF power outage.”
Unlike Waymo, Tesla does not operate a driverless robotaxi service in San Francisco.
Tesla’s local ride-hailing service uses vehicles equipped with “FSD (Supervised),” a premium driver assistance system. The service requires a human driver behind the wheel at all times.
According to state regulators — including the California Department of Motor Vehicles and California Public Utilities Commission — Tesla has not obtained permits to conduct driverless testing or services in the state without human safety supervisors behind the wheel, ready to steer or brake at any time.
Tesla is vying to become a robotaxi titan, but does not yet operate commercial, driverless services. Tesla’s Robotaxi app allows users to hail a ride; however, its vehicles currently have human safety supervisors or drivers on board, even in states where the company has obtained permits for driverless operations.
Waymo, which leads the nascent industry in the West, is Tesla’s chief competitor in AVs, along with Chinese players like Baidu-owned Apollo Go.
The outage-related disruptions in San Francisco come as robotaxi services are becoming more common in other major U.S. cities. Waymo is among a small number of companies operating fully driverless ride-hailing services for the public, even as unease about autonomous vehicles remains high.
A survey by the American Automobile Association earlier this year found that about two-thirds of U.S. drivers said they were fearful of autonomous vehicles.
The Waymo pause in San Francisco indicates cities are not yet ready for highly automated vehicles to inundate their streets, said Bryan Reimer, a research scientist at the MIT Center for Transportation and co-author of “How to Make AI Useful.”
“Something in the design and development of this technology was missed that clearly illustrates it was not the robust solution many would like to believe it is,” he said.
Reimer noted that power outages are entirely predictable. “Not for eternity, but in the foreseeable future, we will need to mix human and machine intelligence, and have human backup systems in place around highly automated systems, including robotaxis,” he said.
State and city regulators will need to consider what the maximum penetration of highly automated vehicles should be in their region, Reimer added, and AV developers should be held responsible for “chaos gridlock,” just as human drivers would be held responsible for how they drive during a blackout.
— CNBC’s Riya Bhattacharjee contributed reporting.
Technology
Xbox is losing the console race by miles. It’s part of Microsoft’s big gaming pivot
Published
16 hours agoon
December 21, 2025By
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The Xbox booth during the Gamescom video games trade fair at the Trade Fair Center in Cologne, Germany, Aug. 20, 2025.
Ina Fassbender | Afp | Getty Images
Microsoft’s Xbox has had a tumultuous year.
A slew of layoffs, price hikes and studio closures have led many to declare — not for the first time — that the Xbox is dead.
Laura Fryer, former executive producer at Microsoft Game Studios, said in June that the company seems to have “no desire or literally can’t ship hardware anymore.”
Former Microsoft executive and ex-Blizzard Entertainment president Mike Ybarra slammed Xbox’s “confusing” strategy in a now-deleted X post in October, saying the company is potentially heading for a “death by a thousand needles.”
The company’s overall gaming revenue decreased 2% year-over-year, with a 29% dip in Xbox hardware sales, according to Microsoft’s first-quarter earnings for fiscal 2026.
The broader console industry has been in a major slump, with hardware spending down 27% year-over-year in November, which is typically a busy shopping month, according to a recent report from research firm Circana.
It was the worst November in two decades, IGN reported, citing Circana data.
Combined Switch and Switch 2 unit sales were down more than 10% during the month and PS5 sales were down more than 40%, IGN said. But the Xbox Series hardware took the biggest beating, with a dramatic 70% drop in sales.
In console sales, Xbox can barely see the leaders this year.
Nintendo‘s Switch 2 has sold 10.36 million units since its debut in June, the company said in its latest earnings report. Sony‘s PlayStation 5 had 9.2 million units sold in 2025, according to its most recent financial results.
Microsoft’s Xbox Series S and Series X, at 1.7 million units, couldn’t outsell the original Nintendo Switch, which launched in 2017 and has sold 3.4 million units so far this year, data from game sales tracking site VGChartz estimated.
Microsoft declined to comment on Xbox sales or numbers.
The company stopped reporting console unit shipments in 2015 as the gap between Xbox and PlayStation widened.
The Series S, Series X and PS5 all originally released in 2020, with some updates being released since then.
In November, Valve made a splash with its next-generation Steam Machine, which is set to launch next year.
The reveal of its console-PC hybrid generated buzz across the gaming landscape, with The Verge declaring that “Valve just built the Xbox that Microsoft is dreaming of.”
The mini cube will be able to run Windows PC games through Valve’s own Linux-based SteamOS as a television console or as a gaming computer. Gamers will have access to Steam’s extensive library of thousands of games.

But Microsoft doesn’t seem too worried about falling behind.
“We’re not in the business of out-consoling Sony or out-consoling Nintendo. There isn’t really a great solution or win for us,” Microsoft Gaming CEO Phil Spencer said in a 2023 podcast.
In congratulating Valve on the release, the Xbox boss gave a nod to the movement to expand gaming access “across PC, console and handheld devices.”
As Sony and Nintendo have firmly established themselves as hardware companies, Microsoft is pushing toward Bill Gates’ original vision of an all-encompassing entertainment hub in the living room.
“Ultimately, the addressable market is anybody who wants to play games, and Microsoft wants to serve that market,” Wedbush analyst Michael Pachter told CNBC.
Microsoft CEO Satya Nadella said in a recent interview with the TBPN podcast that the company’s gaming business model will look to be “everywhere in every platform,” from consoles to TV to mobile.
His comments also hinted that the next Xbox may function more like a PC.
“It’s kind of funny people think about the console and PC as two different things,” Nadella said. “We built a console because we wanted to build a better PC, which could then perform for gaming. So I kind of want to revisit some of that conventional wisdom.”
Xbox President Sarah Bond echoed the idea, saying in a recent interview with Mashable that the company’s next-generation console will have “some of the thinking” seen in the Xbox’s new handhelds, which were built by hardware manufacturer Asus in partnership with Microsoft.
Launched in October, those devices support cross-platform gaming and can run PC games bought from Epic Games, CD Projekt and Valve stores.
Xbox has already incorporated that approach into the latest Backbone Pro, which rolled out in November.
Designed in partnership with Backbone Labs, the portable gaming controller offers access to cloud gaming on mobile, PC, smart TV and other streaming devices.
So what will Microsoft’s new-gen console look like?
Little is known about where the company is at in its development.
A source familiar with Xbox strategy told CNBC that the company is looking at creating an open system that enables players to jump between console, PC and cloud gaming — and any form of entertainment beyond gaming.
Gaming in the cloud
Pachter said that while Microsoft is not completely abandoning hardware, the company is splitting its audience into existing buyers interested in specialized consoles and everyone else.
In a 2019 interview with The Verge, Spencer said that he was not concerned with focusing on console sales as much as making games accessible.
“I do think as we look at the next decade of gaming, as we think about reaching the over 2 billion people on the planet who play games, many of those people won’t be buying consoles and gaming PCs,” Spencer said.
Xbox Game Pass subscription service, which gives subscribers access to games from a variety of publishers, is a clear example of this strategy.
Microsoft has been steadily expanding its title offerings on the service.
The platform’s most basic tier, Game Pass Essential (previously Game Pass Core), which costs $9.99 and launched in 2023 with 36 games, now offers over 50 titles.
Ultimate tier members have access to over 500 titles.
Sarah Bond, head of Xbox partnerships, speaks about Xbox Game Pass during the Microsoft Corp. Xbox event ahead of the E3 Electronic Entertainment Expo in Los Angeles, June 9, 2019.
Patrick T. Fallon | Bloomberg | Getty Images
The growth in cloud gaming has been blistering.
Xbox reported a record 34 million Game Pass subscribers in 2024 and a total Game Pass revenue of almost $5 billion over the last fiscal year.
Xbox said in a November blog post that the number of cloud gaming hours from Game Pass subscribers was up 45% compared to the same time last year. The Microsoft subsidiary also said console players are “spending 45% more time cloud streaming on console and 24% more on other devices.”
In announcing the benchmark, the platform added that Xbox Cloud Gaming is now in 30 countries with the expansion into India, which it called “the fastest-growing gaming market in the world,” home to more than 500 million gamers this year.
Although Microsoft faced heavy criticism from subscribers after increasing the cost of its Ultimate tier by 50% from $19.99 to $29.99 in October, the company is reportedly testing an ad-supported version of Xbox Cloud Gaming.
Omdia senior principal analyst George Jijiashvili told CNBC that a free Game Pass tier would likely act as a user-acquisition tool, especially for gamers who have not invested in consoles yet.
However, due to the high costs associated with cloud gaming, an ad-supported tier would likely not be able to actually drive a meaningful amount of revenue, he said.
Cloud gaming is inherently difficult to scale since it needs to balance computing power and operating costs with user affordability.
“With console-grade cloud gaming, you need to essentially run every single instance of the game in a server,” Jijiashvili said. “You need a dedicated hardware for every single person that’s streaming the game, meaning it just doesn’t scale.”
Despite gaming’s scaling limitations, Microsoft seems committed to doing what it has done with the rest of its products — moving it to the cloud.
“They’ve evolved into a primarily cloud services company,” Pachter said. “So everything they’ve done since they started acquiring studios at Xbox has been toward the connected experience in the home to view entertainment.”
Game studio bonanza
Microsoft has spent the past few years building out its entertainment hub with a catalog of original games through an acquisition blitz.
In 2018, the software giant more than doubled its game studios with a string of acquisitions that included Ninja Theory, inXile Entertainment and Obsidian Entertainment.
Two years later, Microsoft bought ZeniMax Media, which owned Bethesda, for $8.1 billion. It was the company’s largest gaming acquisition until its 2023 purchase of Activision Blizzard for $75.4 billion.
Pachter said that the software giant’s gaming spree was also a move to collect “enough content” to bolster its cloud gaming services.
Yet Microsoft’s approach to using its roster of exclusive titles has seen a stark shift recently.
As Xbox exclusives still struggled to compete with wildly successful PlayStation games like “Marvel’s Spider-Man” and “God of War,” the company has made a definitive pivot away from its original-content strategy.
Bond recently said in an interview with Mashable that the idea of exclusive games is “antiquated” as the company has leaned into cross-platform gaming.
Microsoft announced in October that the upcoming “Halo” game will be available on Sony’s PlayStation 5, marking the first time the major franchise has become accessible on a competing console.
In 2024, Xbox opened four formerly exclusive games to other consoles.
Spencer said at the time that the move did not indicate a change in Xbox’s exclusive strategy, but the company has since continued to bring several former exclusives to rival platforms.
In a January interview, Spencer said that the company won’t “put walls up” where users can engage with Xbox games.
“What we’ve learned is put the games first, make sure the games can be as great as they can,” he said. “We love the experience on our own hardware, on our own platform, but our games will show up in more and more places.”
Cuts and price jumps
Microsoft laid off 1,900 workers, around 9% of its gaming division, in January and slashed another 650 jobs from Xbox in September.
In May, the company also shut down several studios under game publisher Bethesda, including “Redfall” maker Arkane Austin and “Mighty Doom” developer Alpha Dog Games.
The gaming unit was hit again when company-wide layoffs in July led to Microsoft shelving “Perfect Dark” and “Everwild,” games that have reportedly been in development for at least seven years, as well as multiple unannounced projects.
Some have attributed the cost-cutting measures to mounting pressure to hit lofty profit goals.
The company reportedly asked its gaming division in 2023 to target profit margins of 30%, according to Bloomberg, which cited people familiar with the matter.
The goal was a significant jump from the 12% profit margin Xbox reached in 2022, as revealed in court documents, and well above the average video-game industry standard of 17% to 22%, analysts told Bloomberg.
Microsoft told CNBC that while the company does set ambitious goals, the reported 30% profit margin target was incorrect.
Microsoft has raised prices on its aging lineup of flagship consoles twice over the past year. Nintendo and Sony also announced price hikes for their respective consoles in August.
The PS5 currently starts at $549.99, and the original Nintendo Switch and Nintendo Switch 2 cost $399.99 and $499.99, respectively.
Xbox’s new ROG Xbox Ally and ROG Xbox Ally X were priced at $599.99 and a staggering $999.99, respectively.
With a growing number of consoles and handhelds in the market, competition is fierce for a dedicated group of customers that will always be interested in owning hardware.
But Xbox is betting that cloud and cross-platform gaming are the future.
For a decade, claims have been made about the death of the Xbox, and what comes next could fully spell the end, or bring a metamorphosis.
Technology
Your CEO wants to be a social media influencer. Is it cool or cringy?
Published
16 hours agoon
December 21, 2025By
admin
Vladimir Godnik | Fstop | Getty Images
For years, Braden Wallake has posted everything from business lessons to animal pictures on his LinkedIn page. A fateful midweek post on a late-summer day stopped the marketing executive in his tracks.
Wallake shared a teary-eyed selfie with a message about his feelings after laying off staff. Just like that, he was the “Crying CEO.”
“I woke up the next day, texted my marketing person and said, ‘I think I went viral last night,'” said Wallake, whose post has raked in more than 57,000 reactions and 10,000 comments.
Users blasted the HyperSocial CEO as being “manipulative” and displaying “self indulgence.” The photo “would make a great dart board,” another wrote.
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Corporate executives and founders like Wallake were sold on the idea that a vibrant social media presence can boost their personal and firm-wide brand awareness. But the reality is less picture-perfect than it’s made out to be.
In many cases, these leaders come off not as relatable but as cringey. And they’re learning the hard way that their digital footprints can even have material business implications.
“There can be real benefits from CEOs being online, but there can also be great risks,” said Ann Mooney Murphy, a Stevens Institute of Technology professor who has studied how company leaders gain social media celebrity status. “One needs to tread carefully.”
The online executive
The pitfalls of social media usage for business leaders are becoming increasingly clear as more executives take to the platforms. Nearly three-fourths of Fortune 500 chief executives had at least one social media account last year, up from roughly half in 2019, data from Influential Executive showed.
More than seven out of 10 Fortune 100 CEOs with social platforms posted at least once a month in 2024, a 32% increase from the year prior, according to an analysis from communications firm H/Advisors Abernathy released this week. CEOs have flocked in particular to the work-focused social site LinkedIn, where they post three times a month on average.
An active social media presence can help build brand recognition and drive attention from mainstream news outlets, Murphy said. It can also allow executives to develop para-social relationships directly with consumers — something that was once reserved for more-traditional celebrities like actors or athletes, she said.
While company news was king in these posts, H/Advisors Abernathy found executives devoting more social real estate to sharing personal happenings. This softer style of content — examples of which include Meta CEO Mark Zuckerberg sharing pictures from Taylor Swift’s “Eras” tour and Goldman Sachs‘ David Solomon posting details for his DJ sets — can help keep followers engaged, Murphy said.
Goldman Sachs CEO David Solomon performs at Schimanski night club in Brooklyn, New York.
Trevor Hunnicutt | Reuters
A subsector has sprouted up around executives’ social media habits, with several businesses offering training programs or consulting services focused on best practices. PayPal made waves in marketing circles earlier this year when it posted a “Head of CEO Content” role, which paid upwards of $300,000 in part to lead social media communications strategy.
Promise and peril
But in recent years, a growing list of anecdotes like Wallake’s “Crying CEO” experience show how posting through life can go awry.
Jason Yanowitz boasted on X in October that Blockworks, the crypto company he co-founded, saw “massive growth” and hit “record revenues” in 2025. He also said the company was shuttering its news division and recommended staffers to anyone hiring journalists covering digital currencies.
One user suggested that Yanowitz forgo smiley faces and strike a tone with less “triumphancy” in a post announcing job cuts. Someone else replied that “before jumping into what’s next,” he should “address the real people who were impacted.”
Yanowitz, who declined CNBC’s interview request, later wrote on X that he “should not have mentioned revenue” in the original post.
Around the same time as Yanowitz’s tweet, a social media video featuring Snowflake revenue chief Mike Gannon offered a case study on how these incidents can evolve into real-world crises.
In an Instagram clip viewed millions of times, Gannon told a street interviewer that the data storage firm was slated to rake in $10 billion “in a couple of years.” Shortly after, Snowflake said in a regulatory filing that statements made in the interview were not authorized and that investors “should not rely upon” them. The company declined to make Gannon available for an interview.
Tesla CEO Elon Musk has shared visions for his business ventures on social media in between musings about politics and cultural issues. Two years ago, Musk found himself in court defending comments related to business plans made on X, his social media platform formerly known as Twitter.
Alex Spiro, attorney to Elon Musk, center, departs court in San Francisco, California, US, on Tuesday, Jan. 17, 2023.
Benjamin Fanjoy | Bloomberg | Getty Images
In several instances, readers have responded directly to executives whose content they find problematic or cringe-inducing. Some, like Ryan Benson, have also mocked the broader trend of business leaders’ attempting to connect directly via social media.
“It’s just disingenuous,” said Benson, 28. “They’re not trying to speak with people the way that maybe an influencer has success in. They’re trying to talk at people to make them think something about their position.”
Executives’ missteps on social media can catalyze discontent from investors, consumers or employees, according to Murphy of the Stevens Institute of Technology. In some situations, she said social media statements could lead to increased regulatory or legal risk for the companies they represent.
Is all attention good?
Despite the downfalls, corporate leaders who have seen the underbelly of social media don’t regret being online.
HyperSocial’s Wallake said he initially took time away from LinkedIn to let the dust settle and now thinks twice before making a post. But Wallake still recommends other business managers harness social media to grow their brands given the benefits. If someone does bring up his teary picture, Wallake brushes it off.
“If people want to call me the ‘Crying CEO,’ they’re more than welcome to,” Wallake said. “If they actually get to meet me, they’re going to see me smiling way more often than they’re going to see me ever crying.”
When Yehong Zhu, co-founder of media technology startup Zette AI, jumped on a day-in-my-life trend, responders roasted her over perceived laziness. People said she should be “embarrassed” and was “fundamentally useless to society.” One commenter said they were “printing this out and taping it to the wall to remind me every time I catch myself believing in meritocracy.”
Zhu received handwritten hate mail tied to the post sent to her office. But she also noticed a flood of press coverage that included the company’s name and signups to a product waitlist, underscoring the power of publicity — even if it’s negative.
“After there was this huge influx of attention, I realized, you know what, maybe all attention is good attention,” Zhu said. “As long as your name is in their mouth, you’re doing something right.”
Zhu later understood that her post was taken as “rage bait,” a genre of content so infamous that Oxford named it the 2025 word of the year. She’s currently undergoing a social media rebrand and is considering leaning toward controversial posts — with the hope of winning more attention online.
“I was not trying to rage bait,” she said of the original post. “The day that I actually try to rage bait, everybody will be actually enraged.”
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