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The Tech Executive's Guide to Concentrated Stock

Five strategies between "sell everything" and "hold and hope"

Most advisors offer two options for concentrated stock: sell and pay the tax, or hold and accept the risk. This guide covers five strategies most advisors never mention. Names only below. Details are inside.

What's inside
1
The Cashless Collar
2
The Structured Sale
3
Securities-Based Lending
4
Exchange Funds
5
Tax-Aware Investing

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100% Fiduciary
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Fee-Only, No Commissions
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Ex-Goldman Sachs & BlackRock
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Equity Compensation Specialist
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San Francisco Bay Area
The problem
Holding and hoping is not a plan.

When 60, 70, or 80% of your net worth is tied to one company's stock, a bad quarter is not just a brokerage statement line item. It is your retirement, your children's college, and your financial independence.

The tax bill is real. But so is the risk. And the tools that exist between "sell everything" and "hold and hope" are the ones most advisors never bring up.

1
The Cashless Collar Downside protection. No selling required.
2
The Structured Sale A plan that removes emotion from the exit.
3
Securities-Based Lending Liquidity without triggering a tax event.
4
Exchange Funds Diversify without selling a single share.
5
Tax-Aware Investing Build a reservoir of losses before you sell.

The guide explains how each strategy works, when it applies, and what to ask your advisor.

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Who this guide is for
📈
You have $3M or more in a single stock

Concentration risk is real, but selling feels expensive. This guide is the starting point.

💵
You need liquidity without a tax event

College tuition, a home purchase, or a business investment. Selling is not always the answer.

🕑
You said "I should have sold" in the last year

Regret is a process problem, not an intelligence problem. A disciplined system fixes it.

Roshani Pandey, Founder of True Root Financial
Roshani Pandey
Founder & Wealth Advisor — True Root Financial

Roshani spent 16+ years advising ultra-high-net-worth families at Goldman Sachs, BlackRock, Cambridge Associates, and Bessemer Trust before founding True Root Financial. Her goal: bring institutional-level strategy to first-generation wealth builders in technology. True Root is a fee-only, 100% fiduciary firm. No commissions.

The guide is free. The strategies are real.

Download it, read it, and if you want to talk through what it means for your specific situation, we are here.

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