‘Crazy competition’ for SF’s most competitive real estate

After Khalil Lalji closed the first round of funding for his new AI company, Natural, earlier this month, one of the first things he wanted to do with the money was buy billboards around San Francisco, a rite of passage for new tech founders. He soon realized that he had to be patient.

“If you want to buy billboard space, you have to wait six to nine months,” Lalji said, adding that it was even worse when he tried to secure prime real estate around Y Combinator’s outposts in Dogpatch and Jackson Square, home to many startup companies. “The whole of 2026 is already sold out and there is no firm date on when you will be able to get your hands on the sign.”

Low-tech billboards for high-tech companies along Interstates 280 and 101 have long been part of the Bay Area landscape, but their popularity has soared this year as the AI boom has increased the number of well-funded companies that need to stand out. Marketing is also changing as corporate startups adapt their consumer marketing strategies. And San Francisco is coming back to life with an increased demand for apartments, office space, and yes, billboards.

Keith Messick, Vercel’s chief marketing officer, joked that the only good business right now is selling billboards rather than selling advanced chips to AI companies.

“The sign market in San Francisco is very competitive right now,” Messick said. “It’s really amazing.”

AI, the World Cup and the Super Bowl promote the signature ‘crazy competition’

Just two years ago, sign companies were frequently calling Messick and offering deep discounts, known as unsold inventory, on unsold inventory. Now the leverage has changed. In the rare instances when a space becomes available, Messick says he is asked to pay top dollar and must make a decision within 24 hours or a competitor will take the contract. That led to hoarding.

“Most people are trying to lock themselves in for as long as possible,” Messick said. “It’s an interesting dynamic because if you let go of a sign, you’re worried you won’t get another one.”

Demand is so strong that Clear Channel Outdoor cited San Francisco as a key driver of U.S. revenue growth earlier this year.

Heather McKinnon, head of brand at Mercury, which provides banking services to start-ups, said interest rates vary widely but could rise by up to 40% next year in some regions.

“There’s obviously crazy competition right now with all the AI companies, and that’s definitely driving demand for these units,” McKinnon said. “But next year, San Francisco will host the Super Bowl and the World Cup, and those events will make people plan longer because big brands are coming in for that space.”

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Clear Channel and Outfront Media, another major San Francisco billboard owner, declined to share prices. Michael Marvin, director of sales at Outfront Media, would only say, “We’re a supply and demand business.”

He added that “prime inventory” (basically everything from San Francisco Airport to downtown) will be sold out next year.

Marketing has gone back in time

Most people would have a hard time explaining the difference between Vanta (security and compliance) and Vercel (developer tools and web infrastructure), even if they live in San Francisco. Even though both companies are worth billions of dollars.

Vanta posted playful signs in San Francisco that read, “Compliance Not So True to SOC 2.” This is probably a reference to the arcane security certifications that will probably fly over the heads of most people driving by.

But that’s what got them talking about the company, according to Vanta’s early investor Terrence Rohan.

“It works best if it’s clever and memorable,” Lohan says. “The value is in brand building.”

Investors poured $35.7 billion into AI startups last quarter, according to Crunchbase data, and venture capitalists say this makes it even more important to stand out.

“There are so many startups out there, and branding is a great way to differentiate,” said Anthony Heckman of Abstract VC. “These details are more important than ever, and having a memorable sign is definitely one way founders can build their brand.”

Vercel’s billboard is trying to grab your attention with just one line of code: “~/ npm i ai.”

“There’s a shift where everything feels like consumer marketing, even if you’re selling boring enterprise technology,” explains Vercel’s Messick. “People are looking to get attention.”

Messick said signage also acts as a “reinforcement” mechanism to communicate a company’s success.

“There’s an unspoken idea that if you have a lot of billboards, you’re doing really well,” he says.

According to Ray Wu, managing partner at Alumni Ventures, a physical presence can be powerful when hiring competition is high.

“There’s a lot more VC money coming into the AI space, everyone is looking to hire the best talent, and the Bay Area is becoming a talent pool,” Wu said. “It brings legitimacy to the company.”

Far from Vanta or Vercel, Natural, which is building a payments infrastructure for AI agents, is less than three months old. Getting just 100 customers is worth spending $250,000 on a sign, Lalji says.

“In payments, the lifetime value of a customer is very high. It’s not impossible to reverse that calculation and make it seem reasonable,” Lalji said.

Purchasing prime billboard space is difficult, Mercury’s McKinnon said, but the more difficult task is designing something that actually gets people talking as part of a complete marketing strategy.

“Right now, when you drive down the Skyway, you see a bunch of black and white signs that say something about AI, and they all blend together,” she said of the elevated section of Highway 80 that runs through downtown San Francisco. “I don’t think a stand-alone sign like that would do anything other than make the founders and team happy when they drive by.”

Some see the flood of billboards as just another sign of the AI bubble, an expensive vanity project.

“It would be great if the right conversations started,” said Ash Garg, general partner at Foundation Capital. “If not, the founders just paid for a giant selfie.”