European Union flags flutter outside the EU Commission headquarters, in Brussels, Belgium, February 1, 2023
Yves Herman | Reuters
When Gerard de Graaf moved from Europe to San Francisco almost a year ago, his job had a very different feel to it.
De Graaf, a 30-year veteran of the European Commission, was tasked with resurrecting the EU office in the Bay Area. His title is senior envoy for digital to the U.S., and since September his main job has been to help the tech industry prepare for new legislation called The Digital Services Act (DSA), which goes into effect Friday.
At the time of his arrival, the metaverse trumped artificial intelligence as the talk of the town, tech giants and emerging startups were cutting thousands of jobs, and the Nasdaq was headed for its worst year since the financial crisis in 2008.
Within de Graaf’s purview, companies including Meta, Google, Apple and Amazon have had since April to get ready for the DSA, which takes inspiration from banking regulations. They face fines of as much as 6% of annual revenue if they fail to comply with the act, which was introduced in 2020 by the EC (the executive arm of the EU) to reduce the spread of illegal content online and provide more accountability.
Coming in as an envoy, de Graaf has seen more action than he expected. In March, there was the sudden implosion of the iconic Silicon Valley Bank, the second-largest bank failure in U.S. history. At the same time, OpenAI’s ChatGPT service, launched late last year, was setting off an arms race in generative AI, with tech money pouring into new chatbots and the large language models (LLMs) powering them.
It was a “strange year in many, many ways,” de Graaf said, from his office, which is co-located with the Irish Consulate on the 23rd floor of a building in downtown San Francisco. The European Union hasn’t had a formal presence in Silicon Valley since the 1990s.
De Graaf spent much of his time meeting with top executives, policy teams and technologists at the major tech companies to discuss regulations, the impact of generative AI and competition. Although regulations are enforced by the EC in Brussels, the new outpost has been a useful way to foster a better relationship between the U.S. tech sector and the EU, de Graaf said.
“I think there’s been a conversation that we needed to have that did not really take place,” said de Graaf. With a hint of sarcasm, de Graaf said that somebody with “infinite wisdom” decided the EU should step back from the region during the internet boom, right “when Silicon Valley was taking off and going from strength to strength.”
The thinking at the time within the tech industry, he said, was that the internet is a “different technology that moves very fast” and that “policymakers don’t understand it and can’t regulate it.”
Facebook Chairman and CEO Mark Zuckerberg arrives to testify before the House Financial Services Committee on “An Examination of Facebook and Its Impact on the Financial Services and Housing Sectors” in the Rayburn House Office Building in Washington, DC on October 23, 2019.
Mandel Ngan | AFP | Getty Images
However, some major leaders in tech have shown signs that they’re taking the DSA seriously, de Graaf said. He noted that Meta CEO Mark Zuckerberg met with Thierry Breton, the EU commissioner for internal market, to go over some of the specifics of the rules, and that X owner Elon Musk has publicly supported the DSA after meeting with Breton.
De Graaf said he’s seeing “a bit more respect and understanding for the European Union’s position, and I think that has accelerated after generative AI.”
‘Serious commitment’
X, formerly known as Twitter, had withdrawn from the EU’s voluntary guidelines for countering disinformation. There was no penalty for not participating, but X must now comply with the DSA, and Breton said after his meeting with Musk that “fighting disinformation will be a legal obligation.”
“I think, in general, we’ve seen a serious commitment of big companies also in Europe and around the world to be prepared and to prepare themselves,” de Graaf said.
The new rules require platforms with at least 45 million monthly active users in the EU to provide risk assessment and mitigation plans. They also must allow for certain researchers to have inspection access to their services for harms and provide more transparency to users about their recommendation systems, even allowing people to tweak their settings.
Timing could be a challenge. As part of their cost-cutting measures implemented early this year, many companies laid off members of their trust and safety teams.
“You ask yourself the question, will these companies still have the capacity to implement these new regulations?” de Graaf said. “We’ve been assured by many of them that in the process of layoffs, they have a renewed sense of trust and safety.”
The DSA doesn’t require that tech companies maintain a certain number of trust and safety workers, de Graaf said, just that they comply with the law. Still, he said one social media platform that he declined to name gave an answer “that was not entirely reassuring” when asked how it plans to monitor for disinformation in Poland during the upcoming October elections, as the company has only one person in the region.
That’s why the rules include transparency about what exactly the platforms are doing.
“There’s a lot we don’t know, like how these companies moderate content,” de Graaf said. “And not just their resources, but also how their decisions are made with which content will stay and which content is taken down.”
De Graaf, a Dutchman who’s married with two kids, has spent the past three decades going deep on regulatory issues for the EC. He previously worked on the Digital Services Act and Digital Markets Act, European legislation targeted at consumer protection and rights and enhancing competition.
This isn’t his first stint in the U.S. From 1997 to 2001, he worked in Washington, D.C., as “trade counsellor at the European Commission’s Delegation to the United States,” according to his bio.
For all the talk about San Francisco’s “doom loop,” de Graaf said he sees a different level of energy in the city as well as further south in Silicon Valley.
There’s still “so much dynamism” in San Francisco, he said, adding that it’s filled with “such interesting people and objective people that I find incredibly refreshing.”
“I meet very, very interesting people here in Silicon Valley and in San Francisco,” he said. “And it’s not just the companies that are kind of avant-garde as the people behind them, so the conversations you have here with people are really rewarding.”
The generative AI boom
Generative AI was a virtually foreign concept when de Graaf arrived in San Francisco last September. Now, it’s about the only topic of conversation at tech conferences and cocktail parties.
The rise and rapid spread of generative AI has led to a number of big tech companies and high-profile executives calling for regulations, citing the technology’s potential influence on society and the economy. In June, the European Parliament cleared a major step in passing the EU AI Act, which would represent the EU’s package of AI regulations. It’s still a long way from becoming law.
De Graaf noted the irony in the industry’s attitude. Tech companies that have for years criticized the EU for overly aggressive regulations are now asking, “Why is it taking you so long?” de Graaf said.
“We will hopefully have an agreement on the text by the end of this year,” he said. “And then we always have these transitional periods where the industry needs to prepare, and we need to prepare. That might be two years or a year and a half.”
The rapidly changing landscape of generative AI makes it tricky for the EU to quickly formulate regulations.
“Six months ago, I think our big concern was to legislate the handful of companies — the extremely powerful, resource rich companies — that are going to dominate,” de Graaf said.
But as more powerful LLMs become available for people to use for free, the technology is spreading, making regulation more challenging as it’s not just about dealing with a few big companies. De Graaf has been meeting with local universities like Stanford to learn about transparency into the LLMs, how researchers can access the technology and what kind of data companies could provide to lawmakers about their software.
One proposal being floated in Europe is the idea of publicly funded AI models, so control isn’t all in the hands of big U.S. companies.
“These are questions that policymakers in the U.S. and all around the world are asking themselves,” de Graaf said. “We don’t have a crystal ball where we can just predict everything that’s happening.”
Even if there are ways to expand how AI models are developed, there’s little doubt about where the money is flowing for processing power. Nvidia, which just reported blowout earnings for the latest quarter and has seen its stock price triple in value this year, is by far the leader in providing the kind of chips needed to power generative AI systems.
“That company, they have a unique value proposition,” de Graaf said. “It’s unique not because of scale or a network effect, but because their technology is so advanced that it has no competition.”
He said that his team meets “quite regularly” with Nvidia and its policy team and they’ve been learning “how the semiconductor market is evolving.”
“That’s a useful source information for us, and of course, where the technology is going,” de Graaf said. “They know where a lot of the industries are stepping up and are on the ball or are going to move more quickly than other industries.”
Navan, the business travel, payments, and expense management startup, filed on Friday afternoon to go public.
Its S-1 filing with the Securities and Exchange Commission indicates that the company plans to list on the Nasdaq Global Select Market under the symbol “NAVN.”
Navan reported trailing 12-month revenue of $613 million (up 32%) across over 10,000 customers, and gross bookings of $7.6 billion (up 34%), according to the S-1 filing.
Goldman Sachs and Citigroup will act as lead book-running managers for the proposed offering.
Navan ranked No. 39 on this year’s CNBC Disruptor 50 list, and also made the 2024 list.
The IPO market has bounced back this year, with deal activity up 56% across 156 deals (roughly 200 IPO filings in all) and $30 billion in proceeds, up over 23% year over year, according to IPO tracker Renaissance Capital. It has been the best year for IPOs since 2021, though still far below the Covid offering boom years, when over $142 billion (2021) and $78 billion (2020) was raised by IPOs.
This year’s deal flow has been highlighted by hot AI names like Coreweave, as well as some of the startup world’s most highly valued firms from the past decade, such as fintech Klarna and design firm Figma, crypto companies Circle, Bullish and Gemini, and some long-awaited IPO candidates finally hitting the market, such as Stubhub this week, though its shares have slumped since the first day of trading. Top Amazon reseller Pattern went public on Friday.
Launched by CEO Ariel Cohen and co-founder Ilan Twig in 2015, Navan set out to disrupt a business travel sector where incumbents relied on clunky legacy tools and fragmented workflows.
The Palo Alto-based company, formerly called TripActions, refers to itself as an “all-in-one super app” for corporate travel and expenses.
Customers include Unilever, Adobe, Christie’s, Blue Origin and Geico.
It has also been pushing further into AI, with a virtual assistant named Ava handling approximately 50% of user interactions during the six months ended July 31, according to the filing, and a proprietary AI framework called Navan Cognition supporting its platform, as well as proprietary cloud infrastructure.
“We built Navan for the road warriors, for CEOs and CFOs who understand travel’s critical importance to their strategy, the finance teams who demand precision and control, the executive assistants juggling itineraries, and the program admins ensuring seamless events,” the co-founders wrote in an IPO filing letter.
“We saw firsthand the frustration of clunky, outdated systems. Travelers were forced to cobble together solutions, wait for hours on hold to book or change travel, and negotiate with travel agents. They struggled to adhere to company policies, with little visibility into those policies, and after all that, they spent even more time on tedious expense reports after a trip. We felt the pain of finance teams struggling to gain visibility into fragmented travel spending and to enforce policies, and the frustration of suppliers unable to connect directly with the high-value business travelers they sought to serve,” they wrote in the filing.
Revenue grew 33% year-over-year from $402 million in fiscal 2024 to $537 million in fiscal 2025, according to the S-1 filing. The company reported a net loss that decreased 45% year-over-year from $332 million in fiscal 2024 to $181 million in fiscal 2025. Gross margin improved from 60% in fiscal 2024 to 68% in fiscal 2025.
The business travel and expense space is crowded, with fellow Disruptors Ramp and Brex, and TravelPerk, as well as incumbents like SAP Concur and American Express Global Business Travel.
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A gamer plays soccer title Pro Evolution Soccer 2019 on an Xbox console.
Sezgin Pancar | Anadolu Agency via Getty Images
Microsoft said on Friday that it will increase the recommended retail price of several Xbox consoles in the U.S. starting in October because of “changes in the macroeconomic environment.”
The company said it would not increase prices for accessories such as controllers and headsets, and that prices in other countries would stay the same.
While Microsoft didn’t explicitly attribute the increase to the Trump administration’s tariffs, many consumer companies have been warning for months that higher prices are on the way. President Donald Trump has issued tariffs this year on multiple countries with a stated goal to bring more manufacturing to the U.S.
“We understand that these changes are challenging, and they were made with careful consideration,” Microsoft said on its website.
It’s the second time Microsoft has raised prices on its consoles in the U.S. this year. Rivals Sony and Nintendo have also raisedconsole prices in the U.S. as Trump’s tariffs went into effect.
Ticket reseller StubHub signage on display at the New York Stock Exchange for the company’s IPO on Sept. 17, 2025.
NYSE
After a long wait to get public, StubHub has had a rough start to life on the New York Stock Exchange.
Shares of the online ticket vendor dropped 10% on Friday, falling for a third straight day since debuting on Wednesday. At $18.46, the stock is now down 21% from its IPO price of $23.50.
StubHub, trading under ticker symbol “STUB,” has lagged behind fellow market newcomers like online lender Klarna, design software company Figma and stablecoin issuer Circle, which delivered early returns for investors following their recent IPOs. Shares of cybersecurity firm Netskope also rose 10% on Friday in their second trading day, after an initial pop on Thursday.
StubHub had been trying to go public for the past several years, but delayed its debut twice. The most recent stall came in April after President Donald Trump’s announcement of sweeping tariffs roiled markets. The company filed an updated prospectus in August, effectively restarting the process to go public, and has since seen its market cap slip to about $6.8 billion from $8.6 billion at its IPO.
Founded in 2000, StubHub primarily generates revenue from connecting buyers with ticket resellers. In the first quarter, revenue rose 10% from a year earlier to $397.6 million. The company’s net loss widened to $35.9 million from $29.7 million a year ago.
StubHub CEO Eric Baker told CNBC on Wednesday that the company expects recently introduced federal regulations around transparent ticket pricing to cause a “one-time” hit to its financial results.
Regulators are zeroing in on online ticket sellers over their pricing mechanisms and whether the companies are doing enough to keep automated purchasing bots in check. The Federal Trade Commission on Thursday sued StubHub rival Live Nation Entertainment, the parent company of Ticketmaster, accusing it of illegal resale tactics.
While StubHub has failed to excite Wall Street, its struggles haven’t seeped into other deals as the tech IPO market continues to show signs of a resurgence after an extended dry spell. Amazon reseller Pattern Group saw its stock rise 12% on Friday, though shares initially slipped 6%.