Bill Promes

What would you do if you woke up tomorrow with $500,000 worth of a single stock — and selling it meant writing a check to the IRS for $150,000? For a lot of Bay Area tech employees, that's not a hypothetical. It's Tuesday. Concentrated stock positions are one of the defining financial challenges for people who have spent years accumulating equity in a single company. The position is real wealth. The tax bill is real too. And the gap between "I should diversify" and actually doing it is often...

What if the investments that are down in your portfolio are actually one of your most valuable tax planning tools? Most people look at a position that's lost value and see a problem. A mistake. Something to hold until it "comes back." The idea of selling at a loss feels like admitting defeat. But for a Bay Area tech employee with RSUs vesting at a high marginal rate, a portfolio position sitting at a loss isn't just a disappointment. It's an asset, one that can be used deliberately to reduce...

If you work in tech and you've started thinking seriously about your financial life — the RSUs, the equity comp, the California tax bill, the question of whether you'll ever actually feel financially secure — you've probably also started wondering whether you need a financial advisor. And then you searched for one. And immediately got confused. There are thousands of financial advisors in the Bay Area. Some charge commissions. Some manage assets for a percentage. Some call themselves fee-only...