How an Investment Banker Is Trading Bay Area Property for a Piece of an AI Company

Storm Duncan, an investment banker, is marketing his 13-acre Mill Valley property in an unusual deal: he wants to swap it for equity stakes in Anthropic, the AI company. He created a LinkedIn company page to find buyers, marking a rare moment where real estate and private tech company ownership collide.

Duncan bought the Mill Valley property at 114 Inez Place in 2019 for $4.75 million. Now he frames the deal as a way to rebalance his wealth. He has too much money tied up in real estate and not enough in AI companies—so he is trying to swap one for the other.

How the Deal Would Work

The idea is straightforward in concept but complex in practice. Instead of Duncan selling the house for cash and then buying Anthropic shares separately, the buyer would take the property and hand over their Anthropic stock directly. For stockholders locked into their shares by company restrictions, this arrangement could let them move money out of Anthropic without technically selling it.

There is a twist: the buyer gets to keep 20 percent of any gains the Anthropic shares make during any lockup period—the time when shares cannot be sold. This cushion tries to address a real problem. People who work at or invested early in private companies like Anthropic often hold shares worth huge amounts on paper, but they cannot actually cash out anytime soon.

Why This Matters Right Now

Anthropic has raised billions of dollars and sits at the center of the generative AI boom. Employees and early investors own equity that looks valuable on spreadsheets, but the company is still private, so there is no public market to sell into. This creates a gap: wealth that exists but cannot easily be spent.

Duncan moved from California to Miami during the pandemic, leaving the Mill Valley house rented to someone he describes as a prominent venture capitalist. This pattern—keeping California real estate while living elsewhere—became common when tech workers realized they could work from anywhere.

We have seen this liquidity puzzle before. When Facebook was still private, employees found creative ways to turn stock options into cash before the company went public. Real estate trades are a novel solution to an old problem.

The Real Estate Angle

Mill Valley property has appreciated significantly since Duncan's 2019 purchase, driven by its proximity to San Francisco and its appeal to technology executives. That appreciation makes the land valuable collateral for an unconventional deal.

Marketing the property on LinkedIn rather than through conventional real estate listing services (like the Multiple Listing Service) targets a specific group: technology professionals with private company equity. The approach abandons the traditional homebuyer playbook in favor of reaching people with a specific financial profile.

The Legal and Tax Complications

Here is where the deal gets tricky. Private company stock transfers usually require approval from the company itself. Anthropic, like most venture-backed firms, has built-in restrictions on who can buy and sell shares, and the company has a right to match or block any deal.

Tax treatment adds another layer. Trading real estate for stock can trigger tax events for both sides. The Internal Revenue Service might consider it a sale that generates capital gains, depending on how the lawyers structure the transaction. That bill could be substantial for a property that has appreciated millions of dollars.

Due diligence on private company equity is also much harder than checking out a public stock. A prospective buyer would need to review Anthropic's financial statements, cap table (the list of who owns what), and governance structure. That information is normally kept confidential and shared only with existing investors.

The arrangement also assumes both Anthropic's value and Bay Area real estate prices keep rising. That assumption is reasonable over the long term, but it is worth noting that tying two illiquid assets together—assets that are hard to sell quickly—could amplify losses if either one declines sharply.

What This Reveals

This deal attempt exposes a real tension in how wealth works in the AI era. Anthropic and similar companies have reached multi-billion-dollar valuations, concentrating enormous paper wealth in employee and early investor hands. But that wealth sits trapped until the company reaches a major exit event, like going public or being acquired.

The arrangement also reflects the challenges of Bay Area real estate financing in an age when technology professionals often have most of their net worth in equity, not salary. A conventional mortgage assumes regular income—not a pile of restricted stock.

The 20 percent upside share tries to split the difference: the real estate buyer gets diversification now, but they keep a piece of Anthropic's future gains. It is a compromise that might appeal to both sides if the legal obstacles can be solved.

Whether this particular deal closes is less important than what it signals about how technology wealth is evolving. As private companies reach ever-higher valuations and more tech workers live in multiple places, we may see more deals that mix illiquid assets in creative ways. The real challenge will not be finding a willing buyer—plenty of people want Bay Area real estate and AI equity—but navigating the legal, tax, and regulatory hurdles that stand in the way.