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The Briefing
Carrie Wheeler isn’t one of tech’s big names, but she may go down in history as the latest victim of an online mob. ͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­
Aug 15, 2025

The Briefing

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Carrie Wheeler isn’t one of tech’s big names, but she may go down in history as the latest victim of an online mob. The CEO of home-buying firm Opendoor stepped down Friday after weeks of relentless attacks on her on X, including from investor Eric Jackson and venture capitalist Keith Rabois, a co-founder and onetime executive chair of Opendoor. Whoever succeeds Wheeler had better wear a bulletproof vest.

Opendoor occupied a tough business—buying up houses and trying to flip them at a profit—one that real estate ad firm Zillow dabbled in and then exited a few years ago after suffering heavy losses. Wheeler didn’t invent the business. A longtime private equity executive at TPG, she took over as CEO in late 2022 after a stint as chief financial officer, succeeding co-founder Eric Wu, who was demoted as rising interest rates were battering the housing market as well as Opendoor’s business, putting it deeply into the red. As Wheeler said in a post today, she was asked to take over when “the company was in crisis” and “the business needed a reset.” 

Over the past two and a half years, she cut costs, and by the second quarter of this year—which Opendoor reported figures for just a week ago—revenue was growing (barely) and the company was in the black. Whether Opendoor will ever be a great business—exposed as it is to the housing market’s ups and downs—is doubtful. Between 2019 and 2024, it burned through $3 billion in cash, as years of profits alternated with years of red ink. That reality may be why Opendoor has been on the outs for much of the year, falling to a low of 50 cents in mid-July from as high as $2.50 last summer. 

That slump appears to have sparked Jackson’s online campaign to convince the meme-stock community that Opendoor was massively undervalued and that Wheeler’s management was to blame. Rabois was even more brutal about Wheeler’s competence, as this tweet demonstrates. The campaign worked. Opendoor’s stock jumped sharply. And now Wheeler is out, giving her critics a chance to prove their arguments. We wouldn’t bet they’ll be victorious, given the questions about the strength of Opendoor’s business that have circulated for years (see here and here). 

Wheeler’s experience is in some ways reminiscent of the ousting of Sarah Friar as Nextdoor CEO early last year, as the business struggled and its stock price tanked. Like Opendoor, Nextdoor had gone public via a merger with a special purpose acquisition company. The public companies that emerge from SPAC deals have frequently struggled to gain investor confidence, perhaps because they tend to be more marginal businesses that go public via a less demanding process than an IPO. It’s notable that 18 months after Friar was replaced (by her predecessor), Nextdoor stock is trading roughly where it was before Friar quit. Fixing a troubled business isn’t always as easy as replacing the CEO.

What makes the artificial intelligence revolution so fascinating to write about is not just the cool new things AI chatbots can do for you. The AI story also brings together geopolitics, the power industry, the future of the economy, immigration and pretty much everything else. Take our Big Read report today that pulls back the curtain on the vital role immigrants play in AI research. It’s a reminder that immigration restrictions could hurt America’s leading role in AI development. The story is worth reading in full.

One of the other big AI-related geopolitical stories this week concerned the push and pull between the U.S. and Chinese governments over whether Nvidia should be allowed to sell AI chips to China. We broke the news that China’s internet regulators have ordered big Chinese tech firms to suspend orders of Nvidia chips pending an investigation of data security—even as President Donald Trump reversed a ban on sale of those chips to China, in exchange for the U.S. government getting a cut of the resulting revenue.

Meanwhile, the AI deal rush continues to be as crazy as ever. This week we wrote about venture capitalists who are increasingly offering money to startups before the firms have even started to raise money—in some cases they have to tell the wannabe investors to back off. You know you’re in a bubble when this kind of stuff happens.

Among the firms raising money, or trying to, are Rivos, a would-be Nvidia rival...Protege, a startup that links AI model developers with organizations that generate data for use in training large language models…Base Power, founded by Michael Dell’s son Zach, which manages a fleet of home backup batteries…Vercel, a cloud startup that hosts AI apps. Then there is AI search firm Perplexity, which made a PR splash this week by offering to buy Chrome from Google for $34.5 billion. More realistically, Perplexity has also talked to a bunch of much smaller browsers about a possible purchase, we revealed.

Also on the AI front, we took a look at how Elon Musk’s xAI has recruited its team of AI researchers—from Google and other big tech firms, naturally. And in our Dealmaker column, we dug into SoftBank’s OpenAI investment, showing how important the success of OpenAI is to SoftBank and its CEO, Masayoshi Son.

Meanwhile, outside AI, the crypto world is going from strength to strength, as demonstrated by Bullish’s very bullish IPO. President Trump has his own crypto interests, of course. On that front, we dug into the ties between Trump’s son Donald Jr. and crypto payments firm Fintiv. This piece is well worth a read.

• Lyft, the No. 2 ride-hailing firm, on Friday dissolved its dual-class shareholding structure, eliminating a class of stock that had 20 votes each, so that all shareholders will now have one vote per share. The move came the day after Lyft’s two co-founders, who hold supervoting shares, left the board. Before the conversion, the two men, Logan Green and John Zimmer, had a voting stake of 30% despite owning just 2.3% of the stock between them.

• The Federal Reserve said Friday it will end its program scrutinizing the fintech and crypto activities of banks, months after it stopped requiring banks to obtain advanced permission before engaging in crypto businesses.

• Japanese mobile payment app PayPay has confidentially filed for a U.S. listing, the company announced Friday. The move could help fund owner SoftBank’s AI ambitions.

Check out today's episode of TITV in which we dive deep into the business model of Gecko Robotics with CEO Jake Loosararian.

AI Agenda by Stephanie Palazzolo separates hype from reality and explains how AI is transforming industries. The 4x/week newsletter details the innovation and disruption happening in AI, from the AI startup funding frenzy to the major technological breakthroughs that will set the agenda for decades to come. Sign up today.

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