Meet the Airbnb activist hunting for San Diego’s ‘apartment hotels’

Jay Goldberg swears he’s a capitalist. 

It’s a Thursday afternoon and the 42-year-old Hillcrest homeowner is seated at his kitchen counter, scrolling through lines of code he wrote to analyze multiple datasets on his laptop. He’s a Google engineer by trade, but his workday is over, and now he’s hunting through the local real estate market. 

His target? Properties that he calls “apartment hotels” — or entire complexes that have been converted from long-term housing to short-term rentals.

He’s a capitalist, he says, but he’s a capitalist with guardrails, driven by one guiding principle: What’s good for one person shouldn’t come at everyone else’s expense. And he’s become convinced that’s exactly what’s happening in San Diego.

Earlier this year, inewsource revealed a glaring loophole in a San Diego law that allows property owners to obtain a short-term rental license even after carrying out an illegal eviction. It works like this: Investors buy up multi-family properties, clear out the long-term tenants with buyouts or no-fault evictions, and post the units on short-term platforms, such as Airbnb. 

Goldberg has spent years working to identify these properties. 

He gathers data from short-term rental platforms. He combs through active licenses and property records. And when he thinks he’s identified an apartment hotel, or really any short-term rental violation, he turns over what he finds to San Diego officials. 

Then he waits.

Goldberg has developed a system — so much so that, by his count, he and a small group of others have filed more than 2,000 reports with the city of San Diego, flagging everything from improper signage and illegal garage conversions to hot plates spotted in listing photos. 

Their campaign has turned Goldberg and his allies into citizen activists, pushing the city to enforce its own laws and creating a paper trail that, if nothing else, makes it hard to ignore properties they believe are skirting the rules.

“The reason I’ve filed 2,500 reports is not because I expect them all to be solved in a reasonable amount of time or that I even personally think they should all be prioritized,” Goldberg said. “But they’re flags in the sand that say something happened. There’s something that happened here at this time and you can’t sweep it under the rug.”

Goldberg’s interest in short-term rentals started close to home — as a neighbor. A dispute over the townhouse next door, which was operating as a full-time vacation rental, led him to start looking beyond his own shared wall. 

Goldberg later founded Nice Neighbors, a data-driven citizen watchdog group that advocates for “common-sense Airbnb regulation” and enforcement. 

The website includes an interactive map of short-term rentals and a repository of active licenses, Airbnb listings, as well as conversions of apartments to short-term rentals, among others. There are multiple ways for people to report a concern about a short-term rental through the website, either with Nice Neighbors or directly with the city.

“I want people to seek justice,” he said. “I actually want them to be angry, because anger is what motivates people. Personal discomfort is where change is born. And I think there’s a lot of personal discomfort that everyone is suffering in their own silos.”

San Diego leaders have for years grappled with two competing realities: a worsening housing and affordability crisis coupled with the business interests of property owners in a world-class destination city. 

Experts largely point to a fundamental shortage of housing, built up over decades of failing to produce enough homes for residents of all income levels. Half of the city’s current housing supply consists of rental units that are nearly full, which keeps rents high. 

Goldberg and his allies see another force driving the affordability crisis, though. Without stronger regulation and enforcement, they say, property owners are incentivized to turn long-term housing into more profitable short-term rentals.

Every other major California city has rules in place to prevent investors from flipping housing stock to full-time vacation rentals, said Cynara Velazquez, one of several Ocean Beach residents who teamed up with Goldberg. Velazquez is a consultant who co-founded a political action committee called Housing for San Diegans. The PAC promotes candidates who have pledged to limit Airbnb and, conversely, alerts voters to candidates backed by the platform.

Velazquez said Goldberg has organically attracted a following of several concerned residents in Ocean Beach, where folks are apparently dealing with a high concentration of these apartment hotels selling beach access and sunset views to tourists from units that were once naturally affordable.

And it’s disrupting the housing market, Velazquez said.

“We’re fighting an uphill battle against a multinational corporation with unlimited money to spend in San Diego, securing the vote of San Diego politicians,” she said. “Thank goodness there are people like Jay who have so much talent and have made this their hobby.”

Goldberg says he has had success, crediting himself for helping to identify and ultimately shut down at least a dozen “bad actor hosts” who are no longer allowed to run short-term rentals in San Diego.

“I think I’m a little obsessed with power imbalances, I’ll admit that, and there’s a lot of power imbalances,” he said. “Someone who has enough money to buy a multi-family building, do all the renovation and eviction to turn it into an Airbnb, has several other Airbnbs … how are you, as a tenant, equipped to deal with that kind of power?”

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Michael Flore said the phone call came out of nowhere.

He had just moved out of a two-bedroom Pacific Beach apartment that he had rented for more than a decade. One block from work and from the Catamaran Resort, his rent was just $625 when he signed the lease in 2009 — and it hadn’t changed much over the years.

So when new owners bought the apartment complex and offered each tenant money to leave in 2023, Flore wasn’t sure what to do. But they were “very persistent,” he said. When he didn’t accept the offer right away, a real estate agent hired by the new owners knocked on his door.

They will find a reason to kick you out, Flore remembers the agent telling him. You might as well take the money.

“I thought I had no other option,” Flore said. “As soon as we came to some kind of agreement, I found out that I did have options.”

Flore scrambled to learn more about those options, researching tenant protections and housing law and reaching out to anyone he thought might be able to help. But the clock was ticking. Eventually, it was time to leave.

“Since I had been in my place for 15 years, I couldn’t find anything even close to what I had, so I had to move back to New York,” he said. “I had two bedrooms’ worth of stuff I had to get rid of in three weeks. I had to throw out basically most of my life. I ended up just taking a bag back to New York.”

Not long after he left, his phone rang. 

Goldberg was on the other end.

His data analysis had flagged Flore’s building as a possible “apartment hotel” conversion. Goldberg looks for a number of indicators, including how many short-term licenses are obtained after a property changes hands. When more than half of the units in a multi-family development have licenses soon after the sale, he starts making phone calls. 

Goldberg found Flore’s number through a public records search. He wanted to hear what happened, he told Flore, and see whether he could help shine a light on his experience.

“Jay came out of nowhere,” Flore said. “I was just finally like, ‘Oh, somebody does care about what’s going on.’”

For Flore, though, the call came too late. He had already moved out.

“How everything happened, it was so quick,” Flore said. “I felt a little bummed at first for myself, wishing I knew of Jay right when this was happening to me, but obviously the situation is a lot larger than just myself.”

“I think what Jay is doing is amazing for sure,” he added.

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By his own admission, Goldberg thinks about thermodynamics — the study of heat and energy — more than any normal person should. That means thinking about where energy comes from, where it goes and what impact his choices have along the way. 

He’s the kind of guy who grows his own greens in a hydroponic garden and cares for two egg-laying hens — one named Fancy who likes to cuddle and another named Fluffy who likes to bite. He also has two Mexican hairless dogs, Nacho and Paco, who love to frolic at the Ocean Beach Dog Beach.

Even the temperature in his home involves a calculation. Goldberg said he prefers to keep the thermostat high to conserve energy. When he has company, however, he lowers it for their comfort. 

These are the kinds of calculations Goldberg makes, he said, weighing his choices against the Golden Rule: do unto others as you would have them do unto you.

And on this particular morning, he has another calculation to make. 

Goldberg has found another violation. He’s just not sure it’s worth reporting.

He’s standing in the driveway of a three-bed, two-bath Pacific Beach home, looking at the sign posted out front. San Diego law requires licensed short-term rentals to post a notice that’s 8.5 inches by 11 inches, with text in all capital letters, black, bold and at least 20-point font. But here, the sign isn’t big enough and the font is all wrong.

“If the rules are the rules, then it should be the right point font,” he said, thumbing through an app on his cellphone. “Someone coming at night might not be able to read that.”

Goldberg built an app to help him identify what he has determined to be high-priority rentals — these are properties with an active license to rent the entire home on a short-term basis with recent reviews on Airbnb. It shows points on a map, capturing everything from small mom-and-pop owners to large multi-unit operators running these apartment hotels.

“Whenever I’m in an area, I generally go around and audit,” he said, checking for obvious violations, including signage.

The signs aren’t really what Goldberg is after, though. He’s more concerned about the apartment hotels or illegal conversions, such as accessory dwelling units. 

The problem, activists say, is that residents have to select from a list of seven possible violations when reporting a short-term rental. Those include improper signage, excessive trash or illegal conversions, among others. There is no option for what Goldberg calls an apartment hotel — or even an illegal eviction. 

So when his audits turn up something else — a sign that’s too small or a prohibited hotplate in one of the photos posted to Airbnb, for example — a report creates a paper trail tied to that property. It raises a flag and alerts city officials to a potential problem.

This particular home in Pacific Beach is the eighth one he’s checked before noon, and he’s deciding whether to flag it in his system. He had already flagged three other homes for not having any signage. From there, the properties are added to a list where either he or one of his allies can follow up and file a report to the city later.

One of these allies is Kevin Hastings, a business owner and member of the Ocean Beach Planning Board. A mechanical engineer by trade, Hastings said he has personally filed about 500 reports on properties Goldberg flagged, including improper signage or operating without a license.

“I just don’t like seeing out-of-town landlords who are turning a profit at the expense of residents,” he said, “or now former residents who are getting displaced.”

Hastings said he started his activism about a decade ago, back in the “black market days.”

“Airbnb was booming, everything was mysterious, there was no licensing, there was no (short-term tax), there was nothing at that point in time,” Hastings said. “In order to track down these listings, you had to use Google satellite view with photos to try to piece it together and narrow down where these were.”

Fast forward several years, the problem has only gotten worse but there’s more information available, he added. And that’s when he met Goldberg, who clearly had a similar interest in tracking this issue. 

“Except he had a lot more brain power behind it,” Hastings said with a laugh, “in terms of automating it and expanding on it really to a citywide level.”

Hastings said he and others help Goldberg add to his data or file reports, and in turn, they “try to use that data to sway our lawmakers, usually with little or no success,” he said.

Goldberg has developed a list of properties that qualify as apartment hotels by his definition and shared it with a number of city officials.

Seven months have passed since inewsource revealed the loophole that allows these apartment hotels to operate, even after an illegal eviction. City officials still haven’t said how they plan to fix it.

Justin Wesson, senior public policy manager for Airbnb, said the city’s current law aims to strike a balance between the needs of San Diego and residents’ ability to earn supplemental income through short-term rentals.

“While the vast majority of hosts are responsible residents who care about their guests and communities,” Wesson said in an email, “Airbnb is supportive of changes to the ordinance that prevent bad actors from circumventing the intent of the current rules.”

Councilmember Jennifer Campbell, who represents Ocean Beach, Point Loma and Mission Beach, continues to tout the regulation of short-term vacation rentals as a signature achievement, leading the charge to pass the ordinance that took effect in 2023. Campbell and her staff did not respond to questions.

As for the three-bedroom home in Pacific Beach, Goldberg decided hours later not to file a report about the signage. His reason? It’s the owner’s only short-term rental with no other issues. 

At least they have a sign, he said.