Meet the AirBnb hunter exposing vultures using California city’s brutal loophole to push out tenants

A tech worker has turned his coding skills on San Diego’s red-hot vacation rental market, hunting for what he says are “apartment hotels” gobbling up homes once occupied by long-term tenants.

By day, 42-year-old Jay Goldberg works as an engineer for Google. In his spare time, the Hillcrest homeowner pores over property records, short-term rental licenses and Airbnb listings looking for buildings that appear to have undergone a lucrative transformation — moving tenants out and tourists in, according to inewsource.

Goldberg and a small army of citizen watchdogs say they have filed more than 2,000 reports with San Diego officials over suspected short-term rental violations.

Their bigger concern is a loophole they say allows owners to clear tenants from multifamily buildings and then obtain licenses to operate the units as vacation rentals.

San Diego’s rules do not automatically prevent an owner from receiving a short-term rental license if tenants were previously removed through buyouts or no-fault evictions.

That means a building can potentially change hands, lose its long-term residents and reemerge as a collection of vacation rentals — a practice Goldberg believes is worsening the squeeze in an already punishing housing market.

“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 told inewsource. “But they’re flags in the sand that say something happened.”

Goldberg founded Nice Neighbors, a watchdog group advocating for tougher short-term rental enforcement. Its website tracks licenses and Airbnb listings and maps properties the group believes warrant scrutiny.

His obsession began after a neighboring townhouse began operating as a full-time vacation rental. Soon Goldberg was using his engineering background to hunt for similar properties across the city.

One case led him to former Pacific Beach tenant Michael Flore.

Flore had lived in a two-bedroom apartment for more than a decade after initially signing a lease for just $625 a month in 2009. But after new owners purchased the complex in 2023, tenants were offered money to move.

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Goldberg’s system later flagged the building after multiple short-term rental licenses appeared following the property’s sale.

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

But by then, Flore had already left.

The controversy comes as San Diego struggles with a massive shortage of affordable housing. The San Diego Housing Federation estimates the region is short more than 134,500 affordable homes for low-income renters, while major rental trackers like Zillow put typical monthly costs well into the thousands.

Goldberg and fellow activists argue that turning existing apartments into tourist accommodations only worsens the problem.

The issue has been brewing since San Diego’s short-term rental ordinance took effect in May 2023.

The system generally allows one short-term rental license per “host,” but the host does not necessarily have to be the property owner.

NBC 7 previously uncovered an example involving property owner Michael Mills, who was connected to 114 short-term rental licenses in Ocean Beach.

Three tenants at one Mills-owned property told the outlet they received 60-day notices that their month-to-month leases would not be renewed.

At the time, Councilmember Jennifer Campbell’s office acknowledged Mills had not violated the law, while saying the ordinance was not intended to be used that way and changes could be necessary.

Airbnb also told inewsource it supports changes aimed at stopping “bad actors” from circumventing the intent of San Diego’s regulations.

Goldberg, meanwhile, keeps hunting.

He has even developed an app to identify properties he considers high priority and conducts in-person audits looking for violations ranging from missing signs to questionable conversions.

He says his efforts have helped expose at least a dozen hosts who ultimately lost the ability to operate short-term rentals.

But Goldberg insists this isn’t a crusade against capitalism or even Airbnb itself.

“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,” Goldberg told the outlet. “How are you, as a tenant, equipped to deal with that kind of power?”