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A Large Gain Shouldn’t Be an Expensive Problem

Options, RSUs, or an early bet that paid off are all nice problems to have. But tax considerations on a concentrated position can turn that gain into a bind. If you sell to diversify, you may trigger the gain. If you wait, you may stay exposed. That’s why, at Lido Advisors, we coordinate the sale, the tax considerations, and the timing, so keeping the gain doesn’t have to mean keeping the risk, and reducing the risk doesn’t mean losing the gain to taxes.  

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$ 46.4 B

RAUM

40 +

Offices Nationwide

25 +

Years in Business

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RAUM as of 6/30/2026. Lido Advisors was recognized in 2025 by Barron’s and Forbes across several industry rankings, including Barron’s Top 100 RIA Firms, Forbes America’s Top RIA Firms, and Forbes Best-In-State Wealth Advisors. These rankings evaluate registered investment advisors using criteria determined by each publisher and their research partners. Lido Advisors did not pay a fee to be considered for these rankings, though licensing fees may be paid after selection to use the award materials in marketing. View full disclosures.

What Sets Lido Apart

Solutions Beyond the Obvious Ones

Traditional exchange funds can defer the tax on a concentrated position, but they typically come with long lockups, ongoing management fees, and limited liquidity while you’re in them. When that structure doesn’t fit your needs, we build synthetic exchange strategies using derivative overlays to pursue similar diversification without multi-year illiquidity.

Built Around the Position You Have

Most of our strategies are managed in-house rather than handed to an outside manager. That keeps the approach shaped around your cost basis, your restrictions, and your timeline, and removes a layer of external management fees. Options-based strategies, staged selling, and charitable structures each solve a different problem, and which one fits depends on what you want the position to do.

One Team Closes the Gaps

Selling shares can trigger capital gains. Exercising options can trigger AMT before you’ve sold anything. Gifting appreciated stock can change both. When a financial advisor, a CPA, and an estate attorney make these calls separately, a decision that makes sense in one place can create a problem in another. LTax and Enterprise Trust, our affiliated tax and estate teams, sit on the same side of the table as the people managing the position.

Fiduciary. Always.

We’re legally obligated to act in your best interest. We don’t earn commissions on your transactions and we don’t sell products, so nothing about how we’re paid changes based on whether you sell, hold, or hedge.

Lido does not provide legal or tax advice or trustee services. Lido’s affiliates, including, but not limited to, Lido Tax, LLC (“L-Tax”), Enterprise Trust & Investment Company, Enterprise Trust Company (“Enterprise Trust”) and affiliated third-party legal professionals will, upon request, provide formal legal, tax, and/or trustee services for Lido’s client under separate agreement. Prospects and clients are urged to seek the advice of their own independent counsel or tax professional should such services be required. Bill pay and bookkeeping services offered upon request through L-Pay, a division of Enterprise Trust. Referrals to our affiliated providers available. Derivatives are for sophisticated investors who are able to bear the risk of capital loss.

Every Situation Is Different. So Is Our Approach.

A concentrated position has three considerations: How much risk sits in one holding, how much of the gain goes to taxes, and when the sale should happen. Keeping more of the gain requires a strategy that weighs all three at once. Here’s what that looks like for three different investors.

Financial Planning
Investment Management
Trust & Estate Planning
Tax Consulting & Preparation
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Kiran, 40

A decade of options and RSUs has left more than half his net worth in his employer’s stock. We map a multi-year exercise-and-diversification schedule that spreads the tax across brackets and lowers single-stock risk.

maxine
Maxine, 45

A stock she bought early is now her largest holding, with a very low cost basis. Selling outright would mean a large bill, so we weigh gifting, charitable, and hedging options against a staged sale. 

helen
Helen, 60

She wants to turn a concentrated position into retirement income without a tax spike that raises her Medicare premiums. We time the diversification around her income plan.

A concentrated position has three considerations: How much risk sits in one holding, how much of the gain goes to taxes, and when the sale should happen. Keeping more of the gain requires a strategy that weighs all three at once. Here’s what that looks like for three different investors.

Illustrative examples only; not actual clients. Individual circumstances and outcomes will vary.

Perspectives on Capital Gains and Equity

Cap and Cushion: A Compelling Way to Manage Market Risk

Investment Management

Cap and Cushion: A Compelling Way to Manage Market Risk

By Kayla Kaltenecker, CFP®, Director, Chief of Staff, Investment Management Department

Managing Concentrated Stock Positions: A Strategic Guide

Investment Management

Managing Concentrated Stock Positions: A Strategic Guide

By Kayla Kaltenecker, CFP®, Director, Chief of Staff, Investment Management Department

Selling Pre-IPO Shares: A Founder’s Guide to Tax, Timing, and Liquidity

Financial Planning

Selling Pre-IPO Shares: A Founder’s Guide to Tax, Timing, and Liquidity

By Jason Blumberg, Senior Managing Director, Senior Wealth Advisor, Market Lead

RSU Tax Guide: How Restricted Stock Units Are Taxed

Tax Consulting & Preparation

RSU Tax Guide: How Restricted Stock Units Are Taxed

A concentrated position can be hard to let go of, especially when it's the stock that built your wealth in the first place. The right approach may be a disciplined, tax-aware plan you commit to and follow.”

Sanjeev Sardana

Managing Director, Senior Wealth Advisor

Sanjeev Sardana

What We're Asked Most

How can I reduce the capital gains tax when I sell appreciated stock?

Several levers typically help: holding for the long-term rate instead of the short-term rate, using capital losses elsewhere to offset gains (tax-loss harvesting), spreading sales across tax years, gifting shares to family or charity, and, for larger positions, structures such as exchange funds or charitable trusts. The right mix depends on your basis, timeline, and goals, which is what a coordinated plan sorts out.

Can I avoid capital gains tax on my stock entirely?

In some circumstances, certain strategies may reduce or defer capital gains taxes. Donating appreciated shares to a donor-advised fund (DAF) or charitable trust, gifting to family in lower brackets, or, in specific cases, qualified small business stock (QSBS) treatment can reduce or remove the tax on part of a position. The goal is to keep more of the gain within the law. 

Should I sell my concentrated position all at once or gradually?

It depends. A staged approach may be appropriate depending on the investor’s circumstances as it can lower single-stock risk while spreading the tax across years and brackets. If a position is very concentrated or the outlook has changed, faster action sometimes can be worth the tax. It is a trade-off between market risk and tax cost, specific to you. 

How are stock options and RSUs taxed differently when I sell?

It matters for planning. RSUs are generally taxed as ordinary income when they vest, and capital gains then apply to any later growth. Incentive stock options (ISOs) follow their own rules and can create alternative minimum tax (AMT) exposure. Knowing which you hold, and your holding period, changes how much you owe and when. 

My CPA already handles my taxes. Why would I work with Lido?

Your CPA files what happened. We help decide what should happen before it does, coordinating the investment move, the tax timing, and the estate angle, then handing your CPA a clean result. Many clients keep their CPA, and we work alongside them. 

What is tax-loss harvesting, and does it help with a large gain?

Tax-loss harvesting means realizing losses to offset realized gains. It will not erase a very large gain on its own, but paired with staged selling and direct indexing it can lower the net tax in a given year. 

Do I have to move all my assets to Lido to get this kind of planning?

No. We can build and coordinate a strategy around a single position. Some clients start with one decision and grow the relationship over time. 

Request an Introduction

Start a conversation with our team about your goals and how Lido can help. Prefer to schedule by phone? Call us: (800) 301-5436

Brennan Fontana

Brennan Fontana

Senior Vice President, Advisor-Client Matchmaking

By submitting the form, you acknowledge that we collect your name, email address, and phone number to respond to your inquiries and provide you with information about our products and services in accordance with our Privacy Policy. If you are a California resident, please see our CCPA Notice to California Residents.

Brennan Fontana

Brennan Fontana

Senior Vice President, Advisor-Client Matchmaking

By submitting the form, you acknowledge that we collect your name, email address, and phone number to respond to your inquiries and provide you with information about our products and services in accordance with our Privacy Policy. If you are a California resident, please see our CCPA Notice to California Residents.