The Situation

Linh is 33, a staff engineer at OpenAI, and on paper she is worth about $3.6 million. Nearly $3.2 million of that sits in company equity she cannot sell on the open market. Her cash compensation is strong, and she was doing plenty right: maxing her 401(k), keeping six months of expenses in savings, and working with a CPA every spring. By any spreadsheet, she was wealthy.

Then she and her partner started house-hunting in San Francisco. One listing agent even suggested the seller might accept company stock as part of the offer, something that is actually happening in this market. That conversation rattled her. Almost 90% of her net worth was locked in one private company, she had no idea when the next tender offer would come, and no one had ever walked her through what selling would actually cost her in taxes.

The Gap We Found

Nobody was doing a bad job. Her CPA prepared an accurate return every April, looking backward. Her brokerage advisor managed her index funds well, but could not even see the private stock, so it never entered the plan. The result: no target for how much to sell when a tender window opened, no model of the tax bill a sale would trigger, and no awareness that the flat supplemental withholding on equity income falls far short of a 37% marginal bracket. Her single largest asset was invisible to every professional in her life.

What We Did

First, we built a tender-readiness plan before any window opened. Together we set a target: sell roughly 25% of her vested units at the next company-run tender, with the decision made in advance so it would not be emotional when the deadline hit. Concentration above 20 to 25% in a single stock is worth addressing; hers was near 90%, and a private stock she cannot exit freely carries even more risk than a public one.

Second, we ran the tax scenario before the money moved. Alphanso's AI agents parsed her payroll, calculated what had already been withheld, and flagged a $95,000 gap between that and what a tender sale would actually generate in tax. Her advisor turned that into a quarterly estimated payment schedule, which meant no underpayment penalty and no April surprise.

Third, we gave the house fund its own home. Tender proceeds and savings went into a California municipal and Treasury bond ladder earning roughly a 5.5% effective after-tax yield, so the down payment grew safely instead of riding on company stock. Around it, we handled the foundation: a revocable living trust set up before closing, updated beneficiaries, and a backdoor Roth IRA for long-term tax-free growth.

The Result

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• $640,000 of paper equity turned into liquid, spendable money at the tender, the first dollars she could actually use from four years of vesting
• A $95,000 tax gap identified and paid on schedule, avoiding an estimated $13,000 underpayment penalty
• Concentration reduced from nearly 90% of net worth to about 70%, with a standing plan to step it down at every future window
• A conventional cash down payment on their home, no company stock in the deal, and a decision she describes as the first financial choice in years that felt calm

Why This Worked

Linh's CPA, her brokerage advisor, and her employer's equity portal each saw one piece of her finances. Alphanso saw all of it at once, which is the only way an illiquid stock position, a tender calendar, a tax bill, and a home purchase can be planned as one decision instead of four. Because Alphanso is flat-fee, there was no incentive to gather her assets or push a product; the advice was the product. If most of your net worth is on paper and nobody has shown you the path to using it, we would love to walk you through it: request a callback.

This case study is a composite illustration based on real Alphanso client scenarios. Names and identifying details have been changed for privacy. Results are not guaranteed and will vary based on individual circumstances. All investing involves risk, including the possible loss of principal. Alphanso LLC is a registered investment adviser.