The ‘Insane Competition’ for SF’s Most Competitive Real Estate

After Kahlil Lalji closed the first funding round earlier this month for his new AI company, Natural, one of the first things he wanted to do with the money was embark on a rite of passage for new tech founders: Buying a billboard around San Francisco. He quickly found out he would have to be patient.

“If you want to buy billboard space, you have to wait six to nine months,” Lalji said, adding it was even worse when he tried to secure prime space around Y Combinator’s outpost in the Dogpatch or Jackson Square, the home of many startups. “It’s already been completely sold for all of 2026, and there’s no clear date as to when I could ever have those billboards.”

Low-tech billboards for high-tech companies along Interstate 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 needing to stand out. There is also a shift in marketing, as enterprise startups adapt a consumer marketing playbook. And, San Francisco has roared back to life with apartments, office space, and yes, billboards, in high demand.

The only better business to be in right now than selling advanced chips to AI companies is selling them billboards, joked Keith Messick, Vercel’s chief marketing officer.

“The San Francisco billboard market is so hyper competitive right now,” said Messick. “It’s really amazing.”

AI, the World Cup, and the Super Bowl drive ‘insane competition’ for billboards

As little as two years ago, billboard companies frequently called Messick, offering steep discounts for unsold inventory, known as remnant rates. Now the leverage has shifted. In the rare case space opens, Messick says he gets a call to pay top dollar and has to make a decision in less than 24 hours, or a competitor will snap up the deal. That has led to hoarding.

“Most people are trying to lock them down for as long as possible,” Messick said. “It’s an interesting dynamic because there is this phenomenon of worrying if you let a billboard go, you won’t be able to get another one.”

Demand is so strong that Clear Channel Outdoor cited San Francisco as a key driver for its US revenue growth earlier this year.

Rates vary greatly, though they are increasing by as much as 40% next year in some locations, according to Heather MacKinnon, head of brand at Mercury, which provides banking services to startups.

“There’s obviously insane competition with all of the AI companies right now, which are definitely driving up demand for these units,” MacKinnon said. “But also next year, San Francisco is hosting the Super Bowl and the World Cup, and those events have driven people to plan out a lot longer because bigger brands are coming in wanting that space.”

Clear Channel and Outfront Media, the other major billboard owner in San Francisco, declined to share pricing. Michael Marvin, Outfront Media’s sales director, would only say, “We are a supply and demand business.”

He added that “prime inventory”— essentially anything from the San Francisco airport to downtown — is sold out for the next year.

Marketing has ‘gone back in time’

Most people, even in San Francisco, would be hard-pressed to tell you the difference between Vanta (security and compliance) and Vercel (developer tools and web infrastructure) — despite both companies being worth billions.

Vanta plastered San Francisco with playful billboards that read “Compliance that doesn’t SOC 2 much,” a reference to an arcane security certification that would likely soar over the heads of most people driving by.

But it got them talking about the company, according to Terrence Rohan, an early investor in Vanta.

“It’s effective when you’re clever and memorable,” said Rohan. “The value is in brand building.”

Investors poured $35.7 billion into AI startups last quarter, according to Crunchbase data, which VCs say makes standing out all the more important.

“There are so many startups and branding is an incredible way to differentiate yourself,” said Abstract VC’s Anthony Heckman. “These details matter now more than ever. And having a memorable billboard is absolutely one of the ways founders can build their brands.”

Vercel’s billboards have tried to grab eyeballs with simply a line of code: “~/ npm i ai.”

“There’s a shift where everything feels like consumer marketing, even if you’re selling boring enterprise tech,” explained Vercel’s Messick. “People are thinking about getting attention.”

Billboards also serve as a “reinforcement” mechanism to convey a company’s success, according to Messick.

“There’s an implied idea that if someone has a lot of billboards, they’re doing really well,” he said.

A strong physical presence can also be helpful when hiring is so competitive, according to Ray Wu, managing partner at Alumni Ventures.

“A lot more VC dollars are coming into the AI space, so everybody is trying to hire the best people and the Bay Area is the talent pool,” Wu said. “It brings legitimacy to a company.”

Far from being a Vanta or Vercel, Natural, which is building payments infrastructure for AI agents, is not even three months old. Spending $250,000 on billboards will be worth it if the company acquires just 100 customers, says Lalji.

“In the payments, the lifetime value of a customer is quite high, said Lalji. “Backing out that math is not impossible to make it seem rational.”

As hard as it is to buy prime billboard space, the tougher task comes from designing something that will actually get people talking as part of a complete marketing strategy, according to Mercury’s MacKinnon.

“Right now, if you drive the Skyway, it’s a bunch of black and white billboards all saying something about AI that all blend together,” she said, referring to an elevated section of Highway 80 that runs through downtown San Francisco. “I don’t think that a standalone billboard like that is going to do anything for you other than make the founder and the team happy when they drive by it.”

Some see the flood of billboards as yet another sign of an AI bubble, amounting to little more than an expensive vanity project.

“If it starts the right conversations, great,” said Ashu Garg, general partner at Foundation Capital. “If not, the founders just paid for a giant selfie.”