The Situation

Mateo is a 39-year-old staff software engineer at Google in Austin, nine years into his tenure. Between a $340K salary and roughly $280K a year in GSU vests, he and his wife — a school administrator — were in a strong position: 401(k)s maxed, a backdoor Roth he'd set up himself after some forum research, and about $450K in a taxable brokerage account spread across two broad index funds.

This year was his biggest vest yet, and he had plans for it. The couple wanted to fund a home remodel and finally trim the Google stock that had quietly grown to 38% of their portfolio. That meant selling appreciated GOOGL — and Mateo knew from experience that selling meant a painful capital gains bill in April.

The Gap We Found

Nobody was doing anything wrong. His CPA prepared an accurate return every spring, and his index funds were exactly what most advisors would recommend. But the CPA only saw the gains after the year was over, and the brokerage account just sat there. In a choppy market year, dozens of individual stocks inside those index funds swung down double digits — losses that could have offset his GOOGL gains. Inside a fund wrapper, though, those losses are invisible and unharvestable. Mateo was about to realize large gains in the same year his portfolio was full of losses no one could touch.

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What We Did

First, we converted his $450K of index funds into a direct-indexed portfolio — instead of owning two funds, he now owns roughly 350 of the underlying stocks directly, with the same overall market exposure. The difference is that when any individual position dips, our system can sell it, capture the loss for tax purposes, and immediately buy a similar stock so he never steps out of the market. Over the year's swings, that harvested about $52,000 in losses.

Those losses became the budget for his diversification. Using specific lot identification — choosing exactly which GOOGL shares to sell, starting with the highest-cost lots — we trimmed his Google position methodically, letting the harvested losses absorb the gains. The remodel got funded and the concentration came down, with almost no net capital gains tax.

Finally, we moved him to a sell-at-vest approach for new GSUs, so future vests stop rebuilding the concentration. Alphanso's AI agents parsed his payroll after the big vest, flagged that his withholding would fall short, and calculated the quarterly estimated payments — with a reminder before each deadline — so the vest year ended without an underpayment penalty.

The Result

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• $52,000 in losses harvested in year one — offsetting nearly all the capital gains from his GOOGL sales
• Roughly $17,000 in tax savings compared with selling the same shares without harvesting
• Google stock reduced from 38% to 16% of the portfolio, without a tax shock
• Quarterly estimates handled proactively — no April surprise, no penalty, and a remodel that started on schedule

Why This Worked

Mateo's CPA and his index funds were each doing their job — in isolation. The tax win came from one team seeing the whole picture at once: the vest calendar, the concentrated stock, and the losses sitting inside his portfolio, all coordinated in the same plan. Because Alphanso charges a flat fee and acts as a fiduciary, every move was made because it helped Mateo, not because it generated a commission. If a big vest year is coming and you're dreading the tax bill, we should talk: 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.