Sell Stock or Borrow Against It? How AI Employees Are Financing Peninsula Homes

Casey Sternsmith

Sell Stock or Borrow Against It? How AI Employees Are Financing Peninsula Homes

Here's a pattern we've noticed with buyers coming out of Anthropic and OpenAI: the ones who just went through a tender offer are often the most reluctant to sell more shares to buy a house. It sounds counterintuitive — they have more liquidity than ever, and yet they want to touch as little of it as possible. But it tracks. Anthropic's April tender undersold its own $5–6 billion target because employees chose to hold rather than sell, betting the IPO will price higher. If you believe your equity is worth more next year than it is today, selling a large block of it for a down payment is exactly the move you don't want to make.

That's where securities-backed financing comes in, and it's become a real part of how we structure purchases for equity-rich buyers on the Peninsula.

What a securities-backed line of credit actually does

A securities-backed line of credit lets you borrow against the value of a stock portfolio — public shares, and in some structures, private company shares subject to lender-specific eligibility — without selling the underlying position. You keep the equity, you keep the upside, and you access cash for a down payment or full purchase. The tradeoff is that it's a loan, not free money: it carries interest, and if the value of the pledged shares drops significantly, you may face a call to post additional collateral.

For someone holding Anthropic or OpenAI equity that's appreciated fast and is expected to keep appreciating into an IPO, this structure lets you participate in a home purchase now without locking in a sale price on shares you think are still climbing.

Why this matters more for private, pre-IPO equity

Public stock-backed lending is common and well understood. Private, pre-IPO shares are a different animal — not every lender will extend credit against them, and the ones who do typically require the shares to have a demonstrated recent valuation event, like a tender offer or funding round, to establish a lendable value. The good news for AI-sector employees right now: both Anthropic's $350 billion tender and OpenAI's recent secondary in the $400–500 billion range created exactly that kind of recent, documented valuation. That's useful collateral evidence in a way it wasn't a year ago for employees at either company.

How this plays out on a Peninsula purchase

Jumbo and super-jumbo financing is already the norm for most home purchases in Burlingame, Hillsborough, and San Mateo, where price points routinely exceed conforming loan limits. Layering a securities-backed line of credit into that picture typically shows up one of two ways:

Using the line of credit to fund the full down payment while taking out a traditional jumbo mortgage for the balance — this keeps your equity position completely intact and spreads the home's cost across two financing sources instead of one large stock sale.

Using the line of credit as a bridge to move fast on an all-cash offer, then refinancing into a traditional mortgage after close — this is the structure we've used most often for buyers competing in situations where a clean, fast close matters more than the lowest possible interest rate. It's worth noting the leverage has shifted back toward buyers this year: Belmont's active inventory nearly tripled this spring, and homes closing over asking dropped from about 79% to roughly 50%, so the urgency to compete with an all-cash structure isn't what it was twelve months ago.

What to weigh before you go this route

This only makes sense if you're genuinely confident in your equity's trajectory and comfortable with the fact that a lender can require additional collateral if the value drops. It's not a fit for every buyer, and it's not something we advise on directly — that's a conversation for your wealth advisor and a lender who specializes in this kind of lending. What we can tell you is how it fits into a real estate transaction, what timelines it allows for, and which properties on the Peninsula are realistic given the amount you're able to access this way.

If you're weighing whether to sell shares or finance around them for a Peninsula purchase, we're happy to talk through what we've seen work. Reach Casey Sternsmith at [email protected] or 650-678-5455.

Casey Sternsmith

Casey Sternsmith

Founder

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Meet Casey Sternsmith, founding partner of the Sternsmith Group. In business, exceptional service is what matters most to Casey Sternsmith.

With Casey at the helm of the Sternsmith Group, this level of commitment is shared by all members of the group who pride themselves on being excellent listeners with unwavering integrity, and for providing the best advocacy and negotiation skills for their buyers and sellers.

Casey’s philosophy of “love what you do, or do something else” is at the forefront of the entire team, which is evident by their true passion for helping clients achieve their real estate goals.
 
As a leader in real estate marketing, Casey employs tried and true traditional marketing as well as cutting-edge strategies such as social media marketing and professional videos for every home – from small condos to luxury estate properties. Casey’s clients also benefit from her vast personal network as a lifelong resident of the area.
 
As a result, she often achieves unprecedented outcomes for her sellers with quick sales and prices exceeding the list prices. To her buyers, Casey is known for excelling in competitive multiple-offer situations.
 
With more than 10 years of results that speak for themselves, Casey never looks at the process as a transaction, but rather as a personal decision and life choice that impact each and every day of their life. Because of this, a great deal of Casey’s personal business, and the Sternsmith Group’s as a whole, comes from repeat businesses and referrals.
 
Prior to her career in real estate, Casey owned and operated a personal training/Pilates studio in San Mateo where she honed her customer service, management, organization, and marketing skills. Combined with a bachelor’s degree from UC Santa Barbara, all of this proved to be the ideal foundation for her future success in real estate. Casey and her husband have two small children and reside in Hillsborough.
 
Tess Salter

Tess Salter

REALTOR®

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Tess Salter is a top-ranked real estate agent in San Mateo County and a key leader of the Sternsmith Group, known for her exceptional negotiation skills, client-first approach, and record of delivering outstanding results. Tess has helped clients buy and sell homes across San Mateo, Burlingame, Hillsborough, Belmont, San Carlos, Redwood Shores, Redwood City, San Bruno, Millbrae, South San Francisco, Bay Meadows, Menlo Park, and Foster City. She specializes in single-family homes, condominiums, townhomes, luxury estates, and investment properties.

With over 10 years of experience, Tess has sold 71 homes in San Mateo County in 2025 and helped 61 buyers and sellers achieve over $125M in sales in 2024, according to RealTrends. Since 2015, Tess and her partner Casey Sternsmith have closed $1.3B+ in total sales, ranking them among the top 5 agents in San Mateo County and the #1 agents in San Mateo for seven consecutive years.

Tess was recognized by Gentry Magazine as one of the Top 10 Agents Under 40 in 2020, and the Sternsmith Group has been nationally recognized on The Leading 100 for the past seven years, celebrating the top-performing real estate teams in the San Francisco Peninsula.

Tess is known for her expertise in off-market listings, pre-market preparation, luxury marketing strategies, and customized property-specific marketing. She leverages Compass’ advanced technology, social media, and Facebook/Instagram Live tours to maximize exposure and deliver top results. With a strong foundation in finance, accounting, and economics, Tess provides data-driven insights that help clients make strategic real estate decisions.

Outside of real estate, Tess is deeply committed to her community. She served as PARCA Auxiliary President (2024–2025), continues on the PARCA Board (2019–2025), volunteers in Hillsborough schools, served on the West Elementary School Site Council, and chairs the Relay for Life for the American Cancer Society.

With 150+ five-star reviews and a reputation for integrity, responsiveness, and personalized service, Tess Salter and the Sternsmith Group provide exceptional guidance, strategic marketing, and unparalleled support for anyone buying or selling in San Mateo County, Burlingame, Hillsborough, and surrounding Peninsula neighborhoods.

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