San Diego Tries to Redeem Its Worst Real Estate Deal With Affordable Housing

• Sordid path to affordability: San Diego’s most notorious office building is making up for its dirty past with a new life as 100% affordable housing.

• Open to hiring: Opendoor has hired a high profile CEO that looks to turn its meme stock rally into an AI advantage.

• Face your title: National Finanial has partnered with CLEAR to support biometrics for closings, possibly opening the door for more use cases.

Urban Development

San Diego Tries to Redeem Its Worst Real Estate Deal With Affordable Housing

For years, 101 Ash Street has been the most notorious address in San Diego. Once envisioned as a centerpiece for city workers, the downtown tower became a symbol of civic dysfunction after a disastrous lease-to-own deal unraveled. Asbestos contamination, mounting lawsuits, and millions in upkeep costs left the 21-story building empty and draining taxpayer dollars. What was supposed to be a practical solution turned into a cautionary tale of mismanagement.

Now, the city is trying to flip the narrative. A unanimous council vote approved a redevelopment plan that would transform the problem-plagued office tower into nearly 250 affordable apartments, plus ground-floor retail and a childcare center. The project represents a chance at redemption—turning a costly liability into a civic asset at a moment when San Diego desperately needs more housing. But with asbestos still looming and financing hurdles ahead, the risks are as significant as the promise.

The redevelopment is being closely watched not only in San Diego but across the country, where cities are wrestling with empty office towers and housing shortages. If successful, 101 Ash could become a model for adaptive reuse, showing how even the most troubled assets can be reimagined. If it fails, the tower may once again stand as a reminder of lost opportunities and public distrust. Either way, its outcome will echo far beyond downtown San Diego.

Overheard

Opendoor Bets on New CEO and AI to Revive iBuying Model

Opendoor has spent the last few years trying to climb out of a hole. Revenue fell from $6.9 billion in 2023 to $5.2 billion in 2024, and while recent quarters have shown narrowing losses—$29 million in Q2 compared to $109 million a year earlier—the company’s guidance suggests profitability is still out of reach. The firm has managed to generate positive returns for short stretches, but the volatility of its results underscores how difficult it has been to make the iBuyer model work at scale.

Despite these fundamentals, Opendoor’s stock has become a favorite of retail traders. Shares are up more than 900 percent over the past three months, fueled by a surge of meme-stock speculation. Trading volume spiked after calls from prominent investors on social media, with the stock jumping nearly 95 percent in a single day. But with short interest sitting above 24 percent, many analysts see the recent rally as more about momentum than market confidence.

Into this mix comes a leadership change and a strategic pivot. Shopify’s former COO is now at the helm, and Opendoor is emphasizing artificial intelligence as a way to sharpen pricing, improve turnover, and finally bring stability to its margins. If the technology delivers, AI could give Opendoor the competitive advantage it has always lacked. If not, it risks becoming just another narrative to keep speculative investors from moving onto the next meme stock.

Title Insurance Could Finally Make Real Estate Adopt Biometrics

Fidelity National Financial, the country’s largest title insurer, is bringing biometrics into real estate transactions through a new partnership with CLEAR. The integration will allow buyers and sellers using FNF’s inHere closing platform to verify their identities with fingerprint and facial recognition, a move aimed at curbing wire transfer scams and impersonation schemes that have surged in recent years.

Biometric technology has tried to break into property before, mostly through building access and tenant systems, but pushback around privacy and legal liability stalled adoption. What makes this effort different is the scale of the players involved. FNF underwrites nearly a third of U.S. title insurance policies, and CLEAR already has more than 30 million enrolled users with technology vetted for compliance at airports and other federal checkpoints.

For an industry that has struggled to modernize its security protocols, this could mark a turning point. By embedding biometric checks at the closing table rather than the lobby, FNF and CLEAR may have found the use case that finally gets real estate comfortable with biometric verification. If successful, it could push identity authentication from an optional add-on to a standard part of the transaction process.

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