True Root Financial Advisor

06/16/2026

Your concentrated stock is down 25%.

Sell, and you trigger a massive tax bill. Hold, and you're exposed to another drop.

Most advisors tell you those are your only two options.

There's a third. You can protect your downside, keep most of your upside, and pay nothing out of pocket. No shares sold. No tax event today.

It's called a cashless collar. Large family offices use it. Most individual advisors never bring it up.

I break down exactly how it works in this 3-minute video.

If you're holding a concentrated position and you're not sure what to do next, watch this. Then let's talk. Book a call at www.truerootfinancial.com

06/11/2026

Most advisors hand you a risk questionnaire, drop you in a model portfolio, and check in once a year.

At $8 million, that isn't advice. It's administration.

Here's what I think makes True Root Financial different.

I don't wait for you to bring me ideas. I bring them to you. Before your RSUs vest. Before the next earnings call. Before the tax window closes.

I spent my career advising families whose wealth had lasted 7-8 generations. I saw how that money was actually managed. No single position over 10%. Taxes were treated as part of the strategy, not a surprise in April. Every piece working together instead of fighting each other.

That level of thinking used to be reserved for people who inherited their wealth.

I built True Root Financial to bring it to people earning it for the first time.

So when you sit across from me, you won't hear "just hold it and hope." You'll hear about the tools that actually fit a concentrated position. Not because they sound sophisticated. Because they're built for your situation.

If you've outgrown an advisor who only does what you ask, let's talk.

Book a call. Link in the comments below.

06/09/2026

If every good idea in your financial life came from you, you don't have an advisor. You have an order taker.

I built True Root Financial around three principles which flip that.

These principles are the same ones I used advising families with generations of wealth.

Here they are, start to finish.

Curious how they'd apply to your equity and your taxes? Let's talk.

Book a call at truerootfinancial.com

06/04/2026

Meta withholds 22% on your RSU vesting.

Your actual combined rate in California is closer to 50%.

On $300K in RSU income, that gap is nearly $100K owed at tax time.

Most employees don't know you can change your withholding election. A simple adjustment before the vest eliminates the surprise. After the vest, it's too late.

This is what I mean when I say the structure of your decisions matters more than the decisions themselves.

Two Meta employees can sell the same amount of stock in the same year and walk away with very different tax bills.

The one who sold in a lower-income year, harvested losses against the gains, and used the right account structure comes out meaningfully ahead.

Not because the choice was different. Because it was structured better.

These strategies aren't complicated. They just aren't well known outside of advisors who specialize in concentrated equity.

I wrote a full breakdown for Meta employees. The withholding fix, the mega backdoor Roth, cashless collars, direct indexing, and how to plan around a career transition.

If you've spent years building this wealth, it's worth five minutes to see how to protect it. Full blog link in the comments.

06/02/2026

Meta employees: you've done the hard part.

You showed up, vested your RSUs, and built real wealth.

Now comes the part nobody prepares you for.

Most Meta employees know they should diversify. Very few realize how much money is lost in how they do it.

Selling gradually sounds reasonable. Staying mindful of taxes sounds reasonable. But a series of reasonable decisions doesn't automatically lead to the best outcome. The structure behind those decisions is what matters.

A few things I see go wrong most often:

1. Concentration keeps growing even while you're selling, because new vests arrive faster than shares go out.

2. Taxes get managed year by year instead of optimized across years. That difference can be six figures over a career.

3. After selling Meta, many employees buy the S&P 500 without realizing it's 30% tech. The concentration just moved.

4. Career transitions change everything. A spouse stepping back, a sabbatical, starting something new. These create tax windows most advisors never flag.

The hidden risk isn't the stock. It's how you exit it.

If you want a second set of eyes on how your equity decisions are structured, book a call. Link in the comments below.

05/28/2026

I've been talking to a lot of Apple, Meta, and NVIDIA employees lately.

Different companies. Same situation.

Millions in a single stock. A tax bill that feels like a wall. And an advisor who's never once walked them through what's actually available.

Not because the options don't exist.

Because most advisors aren't built for this problem.

Here's what I keep seeing: the conversation stays stuck at "sell or hold." Sell means a 37%+ tax hit. Hold means the risk stays. So nothing happens. And every quarter that passes, the concentration gets harder to unwind.

But there's a whole range of strategies between sell and hold that most people have never been shown.

A cashless collar can protect your downside without selling a share.

A structured selling plan moves you out gradually, across tax years, with discipline instead of emotion.

Securities-based lending can give you liquidity without triggering a single dollar in taxes.

Tax-loss harvesting on a portion of the position can offset gains elsewhere.

If you're holding a concentrated position and the conversation with your current advisor never goes beyond "just hold it," that's worth paying attention to.

I put together a free guide that walks through the specific strategies available for concentrated stock. It's written for tech executives, not financial theory majors.

Download it in the comments below.

05/26/2026

Most advisors never bring up the options.

Not because the options don't exist.

Because they don't specialize in this.

I filmed this video a few months ago for tech executives sitting on millions in a single stock. The math I walk through is the same math that keeps coming up in my conversations today.

The tax bill feels enormous. So you hold.

Then the stock drops 30%, 40%. Now you've lost more than the taxes would have cost.

But selling still isn't your only move. There are strategies built specifically for this situation. Most executives I talk to have never heard of them from their current advisor.

This video walks through what those strategies are and how they work.

If it resonates, book a 30 minute free discovery call. We'll look at your actual situation together.

No pitch. Just a conversation. Link in the comments.

05/22/2026

If you are at a private company doing secondaries or heading toward an IPO, read this.

Or if you just left one and still hold equity, this applies to you too.

This is where the biggest financial decisions show up. And where the most
expensive mistakes get made.

I keep seeing the same pattern.

People exercise and sell without a plan. Or they wait and hope for a better price.

Then the taxes hit.

Ordinary income. AMT. State tax.
Six figures gone in one year.

Not because selling was wrong but because no one planned it.

The real decisions happen before the event.

When to exercise.
How much to sell.
How it fits into your income that year.

If you miss that window, most of the outcome is already set.

And these events do not happen once.
Secondaries. Tender offers. IPOs.

Each one is a chance to get it right.
Or keep overpaying.

If you are in this position, now is the time to plan. Not after. If you are selling your shares in a secondary, let’s chat. Book a call at truerootfinancial.com. Link in comments.

True Root Financial is a woman-owned & minority-owned, fiduciary financial advisor & planner in San Francisco bay area. We offer investing & wealth planning

05/20/2026

If you are selling pre-IPO shares in a secondary, read this.

A tech executive I know did exactly that.
Taking money off the table made sense.

But a big chunk went straight to taxes.

Not because selling was wrong.
Because no one planned it.

He had a CPA. An advisor. A plan.
They just were not talking to each other.

So he exercised and sold in the same year.
That pushed his income up, triggered AMT, and drove his taxes way higher.

This is what most people miss.

The mistake is not the sale.
It is everything that happens before it.

When to exercise.
How long to hold.
How it fits into your income that year.

That is where the money quietly slips away.

And these events do not happen once.
Secondaries. Tender offers. IPOs.

If each one is handled on its own, you keep paying for it.

By the time the liquidity event hits, most of the outcome is already set.

The time to plan is before it happens. Not after.

If you have pre-IPO stock, book a call at truerootfinancial.com. Link in the comments.

True Root Financial is a woman-owned & minority-owned, fiduciary financial advisor & planner in San Francisco bay area. We offer investing & wealth planning

05/19/2026

He had a CPA. An advisor. A plan.

And still lost a huge chunk of his liquidity to taxes.

The problem wasn't the decision to sell. Watch to find out where it actually went wrong.

Book your strategy call at truerootfinancial.com