True Root Financial Advisor

Call Directions Website Contact the business

True Root Financial Advisor We are a fiduciary financial advisor providing investing, tax planning and wealth planning advice for tech entrepreneurs & tech professionals.

If Alphabet stock fell 40% next year, would your plans still hold up?For many Google employees, the honest answer is "I'...
10/16/2026

If Alphabet stock fell 40% next year, would your plans still hold up?

For many Google employees, the honest answer is "I'm not sure." That's usually a sign that too much of their future depends on one stock.

One week from today, I'm hosting a free masterclass to help you answer that question with a real plan instead of a guess.

We'll walk through how much Alphabet you actually need to keep, why the tax withheld on your GSUs often falls short, and how to diversify without paying more tax than necessary.

Date: Thursday, October 22
Time: 11:30 AM PT

Register here:
https://www.linkedin.com/events/theequityplaybookforgoogleemplo7508650171866566656/theater/

10/15/2026

Selling Stripe stock at every tender offer won't fix your concentration.

Not when new RSU grants keep arriving every year.

A longtime Stripe employee I spoke with had over $4 million in Stripe equity. She was bullish on the company. She still felt like her family was winging it.

Her real questions had nothing to do with Stripe's valuation:
1. Can my spouse cut back to part time?
2. Can we pay for college for both kids without touching our Stripe shares?
3. How much Stripe stock should we keep, and how much should we diversify?

You can't answer those by guessing where the stock goes next. You need a plan.

That plan tells you how much to sell, what taxes to expect, and what the proceeds are for, all before the tender window opens. It also accounts for the refresh grants you'll receive over the next few years.

When the window opens, you just follow the plan.

If you work at Stripe and your equity has become a big part of your net worth, book a no obligation call. We'll build your plan before the next tender offer.

Stripe’s valuation dropped from $95 billion to $50 billion. Then it climbed to $159 billion.If most of your net worth is...
10/13/2026

Stripe’s valuation dropped from $95 billion to $50 billion. Then it climbed to $159 billion.

If most of your net worth is in stripe stock, you've felt every one of those swings.

Many Stripe employees make each tender offer decision on instinct. Sell some, maybe. Hold, maybe. It depends on the week.

A better approach is to decide before the window opens. Know how many shares you'll sell, what the tax bill will be, and what the money is for. Then plan for the RSU grants still coming, not just the ones you already have.

I wrote about a Stripe employee with over $4 million in equity who still didn't feel financially secure. Full article in the comments.

10/08/2026

Holding your vested Google stock doesn't save you a dollar in tax.

GSU tax is locked in the day they vest. After that, holding is really a new decision to buy Alphabet stock with money that's already been taxed.

One Google employee I worked with had been vesting GSUs for five years without selling. Her vested Alphabet shares alone were worth over $600,000, and more grants were still coming.

She wasn't making a bet on Alphabet. She just never had a plan.

So we built one:
1. Sell a consistent portion of every future vest.
2. Put the proceeds into a diversified portfolio built around her retirement timeline.

One decision, made once. Not four times a year.

Your plan should also cover the withholding gap. A flat 22% federal rate often falls short of what high earners actually owe.

If you've never added up your vested and unvested GSUs in one place, start there.

Book a no obligation call, and we'll map your full Alphabet exposure together.

Google employees: how much of your future should depend on Alphabet stock?For many long tenured Googlers, Alphabet has q...
10/02/2026

Google employees: how much of your future should depend on Alphabet stock?

For many long tenured Googlers, Alphabet has quietly become their largest asset. Each GSU vest adds a little more, and few people ever stop to decide how much is enough.

On Thursday, October 22, I'm hosting a free masterclass on that question. You'll leave with a clear framework for your equity decisions.

Date: Thursday, October 22
Time: 11:30 AM PT

Register through the link here:
https://www.linkedin.com/events/theequityplaybookforgoogleemplo7508650171866566656/theater/

10/01/2026

How much NVIDIA stock should you sell?

I usually answer with a different question. How much could you keep and still live the life you want if NVDA fell by half again tomorrow?

That number is your starting point. It doesn't require predicting the stock.

A longtime NVIDIA employee recently told me he didn't want to spend the next twenty years doing the same thing. He had done everything right. But most of his wealth answered to one stock price, and the tax bill on his oldest shares kept him stuck.

This is how I'd approach a position like his:

1. Sell the higher basis shares first. The tax cost is small.
2. Save the larger sales for a year when income drops, like after leaving the company or once a big grant finishes vesting.
3. Use direct indexing, which means owning the individual stocks in an index. Selling the ones that dip creates tax losses that can offset gains on your NVDA sales.
4. Give the lowest basis shares a slower, multi year plan.

The goal isn't to own zero NVIDIA stock. It's to reach the point where your freedom no longer depends on it.

If you're holding a concentrated NVDA position, book a no obligation call. We'll map
out what a phased plan could look like for your tax situation.

NVIDIA fell about 50% in 2022. Would your plans have survived it?If you've spent years at NVIDIA, a big share of your ne...
09/29/2026

NVIDIA fell about 50% in 2022. Would your plans have survived it?

If you've spent years at NVIDIA, a big share of your net worth may be sitting in NVDA stock. Selling feels expensive. Holding feels risky. So most people do nothing.

There's a better way. Diversify over several years instead of in one painful sale. Time the biggest sales for a lower income year. Use direct indexing to harvest losses that offset your gains. Give your oldest, lowest basis shares their own exit plan.

I wrote about a longtime NVIDIA employee who didn't want a bigger portfolio. He wanted his time back.

The full story and strategy are in the article. Link in the comments.

09/24/2026

“Just sell some of the stock.”

I hear this surprisingly often from executives who have accumulated millions of dollars in company equity.

The advice itself may not be wrong. If one stock represents a significant portion of your wealth, reducing that concentration can make a lot of sense.

But “sell” is a recommendation. It’s not a strategy.

For a highly appreciated position, the way you diversify matters.

A thoughtful strategy might include:
1. Timed selling: Spreading gains across multiple tax years rather than creating one enormous taxable event.
2. Lower-income years: Taking advantage of a sabbatical, retirement, job transition, or other period when income may be temporarily lower.
3. Tax-lot selection: Deciding which shares to sell first based on cost basis, holding period, and the broader plan.
4. Direct indexing: Building a diversified portfolio that can harvest losses over time to help offset gains as concentrated shares are sold.
5. Protective strategies: For someone who is no longer subject to their employer’s trading restrictions, options strategies such as collars may help manage downside risk while the position is being unwound.

There isn’t one technique that works for everyone.

The point is that diversification should be coordinated with your taxes, cash-flow needs, future equity compensation, and long-term financial plan.

For someone with millions of dollars tied up in one stock, “just sell it” leaves a lot of planning on the table.

09/17/2026

A client took money off the table in a secondary offering last year.

Good decision. He was overconcentrated and wanted liquidity.

Then he saw the tax bill.

Here's what happened. He had a CPA. He had an advisor. Nobody was coordinating the timing.

He exercised and sold in the same year. That stacked his income and pushed him into a much higher tax bracket than he needed to be in.

The mistake wasn't the sale. It was everything that wasn't planned before it.

1. When to exercise
2. How long to hold before selling
3. How the sale would interact with his other income that year

None of that was mapped out in advance. So when the liquidity event happened, the outcome was already locked in.

This is not a one time problem either. Secondaries, tender offers, IPOs, they all create the same decision point. If each one gets handled on its own without a plan, you pay the price every time.

If you're holding private stock or a concentrated position and something looks like it might create liquidity soon, the time to plan is before it happens, not after.

Book a complimentary call with me if you want to talk through your situation.

09/15/2026

A tech executive sold stock in a secondary offering. Smart move on paper.

Then taxes took a bigger bite than they should have.

Not because he sold. Because of what happened before he sold. Watch the video to see the actual mistake.

Book your strategy call to ensure you don’t make the same mistake. Link in the comments.

Address

San Francisco, CA
94109

Telephone

+14153236602

Website

Alerts

Be the first to know and let us send you an email when True Root Financial Advisor posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to True Root Financial Advisor:

Shortcuts

Share

Category