How to Sell Your Businessand Keep $2.6 MillionMore of It

The Charitable Remainder Trust strategy that high-net-worth business owners and investors use to legally slash capital gains taxes — and still fund their retirement.

By Yesit J. Campo, CPA  ·  BIZ CPAs Miami  ·  April 2026

$2.6M+ Tax savings on a $20M business sale

60% Reduction in immediate capital gains tax

3 Benefits: tax savings + income + legacy

You spent decades building your business.

You sacrificed weekends, reinvested profits, navigated downturns, and finally arrived at the moment you've been working toward: a sale.

Then your accountant shows you the tax bill.

On a $20 million sale with a $4 million cost basis, the federal and state government takes $4.6 million — before you've spent a single dollar of your proceeds. Nearly a quarter of your life's work, gone in one transaction.

What if there was a legal strategy that could cut that number by more than half — and simultaneously generate lifetime income and support causes you care about?

There is. It's called a Charitable Remainder Trust. And most business owners have never heard of it until they're sitting across from the wrong accountant — or the right one.

What Is a Charitable Remainder Trust?

A Charitable Remainder Trust (CRT) is an IRS-recognized tax planning structure that allows you to transfer appreciated assets — a business, real estate, stocks — into a trust before a sale. The trust then sells the assets tax-free, reinvests the full proceeds, and pays you a regular income stream for life or a defined term. When the trust terminates, the remaining assets go to your designated charitable beneficiaries.

It accomplishes three things simultaneously:

WITHOUT a CRT You pay capital gains tax on the full gain at the time of sale. At a combined federal + state rate of 28.8%+ on a $16M gain, you lose $4.6M immediately — before investing a dollar. ❌  $4,608,000 total tax liability ❌  No lifetime income strategy ❌  No charitable legacy ❌  No estate tax reduction

WITH a CRT You contribute appreciated assets to the trust before the sale. The trust sells tax-free, reinvests the full $11M, and pays you lifetime income while generating a substantial charitable deduction. ✅  $1,844,500 total tax on the sale ✅  Lifetime income stream ✅  $2–3M charitable deduction ✅  Estate tax reduction

The Three Core Benefits of a CRT

1. Capital Gains Deferral — and Avoidance

When you contribute appreciated assets to a CRT before a sale, the trust — not you — owns the asset at the time of the transaction. Because the trust is a tax-exempt entity, it can sell the asset and reinvest the full proceeds without triggering immediate capital gains tax. You defer — and in many cases effectively avoid — a large portion of the tax that would otherwise be due.

2. Immediate Charitable Income Tax Deduction

At the time of the contribution, you receive an income tax deduction based on the present value of the remainder interest that will eventually pass to charity. On a large contribution, this can represent a $2–3 million deduction that offsets income in the year of the sale and can be carried forward for up to five additional years.

3. A Reliable Lifetime Income Stream

The CRT pays you — or your designated beneficiaries — a fixed percentage of the trust's assets each year, for life or a defined term. This creates a predictable, tax-advantaged income stream funded by the full reinvested proceeds — not the after-tax amount.

Real Case Study: $20 Million Business Sale

Meet John. He founded a C corporation 25 years ago. The anticipated sale price is $20 million. His original cost basis is $4 million. Without any planning, here's what happens:

Without CRT — The Full Tax Hit

Capital gain: $20M − $4M = $16,000,000

Federal capital gains tax (20%): $3,200,000

Net Investment Income Tax (3.8%): $608,000

State tax (~5%): $800,000

TOTAL TAX DUE:  $4,608,000

Now here's what happens when John works with a CPA who knows about Charitable Remainder Trusts — before the sale closes.

The CRT Implementation — Step by Step

01 Contribute Transfer $11M of appreciated stock to the CRT BEFORE the sale closes. This removes $11M from your taxable estate immediately.	02 CRT Sells Tax-Free The trust sells the $11M in stock with NO immediate capital gains tax. The full $11M is reinvested to generate lifetime income for you.
03 Direct Sale Sell the remaining $9M directly. With a $1.25M cost basis, you report a $7.75M capital gain — at 23.8%, that's $1.84M in tax on this portion only.	04 Collect the Benefits Total tax: $1.84M vs. $4.6M without CRT. Save $2.6M+ — plus receive lifetime income AND a charitable deduction of $2–3M.

The Result With CRT

Tax on direct sale portion ($9M): $1,844,500

Tax on CRT portion ($11M): $0 at time of sale

Charitable income tax deduction: ~$2,000,000–$3,000,000

Lifetime income stream: Funded by full $11M — tax-free reinvestment

TOTAL TAX SAVINGS:  $2,600,000+

Important Considerations

A CRT is a powerful strategy — but it's not for everyone, and it must be structured correctly to be effective and withstand IRS scrutiny. Here's what to keep in mind:

• The contribution to the CRT is irrevocable. Once assets are transferred, you cannot reclaim the principal — only the income stream and the tax benefits.

• The strategy works best for assets with a very low cost basis relative to fair market value — businesses, real estate, and highly appreciated stock are ideal candidates.

• The charitable beneficiaries must be IRS-qualified 501(c)(3) organizations. You can designate a private family foundation if structured properly.

• Timing is critical. The contribution must occur before the sale agreement is finalized. A CRT established after a sale is signed may be disallowed.

• The IRS requires that at least 10% of the initial fair market value of the trust must be projected to pass to charity. This affects the payout rate and term.

💡  This strategy is most impactful for business owners, real estate investors, and high-net-worth individuals with appreciated assets valued at $1M+ who are planning a liquidity event in the next 1–5 years.

Why This Conversation Starts With Your CPA

Charitable Remainder Trusts require coordination between your CPA, your estate planning attorney, and a trustee. The tax savings are real — but so is the complexity. Done incorrectly, a CRT can be disallowed, triggering the very tax liability you sought to avoid.

At BIZ CPAs Miami, we specialize in proactive tax planning for business owners facing significant liquidity events — sales, mergers, real estate transactions, and inheritance situations. We identify strategies like CRTs, cost segregation, captive insurance, and entity restructuring well before the transaction closes — because that's the only time these strategies can work.

By the time you're sitting at the closing table, your options are limited. The work happens before that moment.

"The business owners who consistently pay less in taxes aren't doing anything illegal or complicated. They just have someone in their corner who's thinking ahead."

— Yesit J. Campo, CPA  ·  Founder & CEO, BIZ CPAs Miami

Selling a Business or Appreciated Asset?

A Charitable Remainder Trust could save you over $2.6 million in capital gains taxes — while creating lifetime income and a lasting legacy. Book a confidential 30-minute strategy call with Yesit J. Campo, CPA.

📅  calendly.com/bizcpas/demo-appointment

(305) 593-2003  ·  bizcpas@bizcpas.biz  ·  bizcpasmiami.com

About BIZ CPAs Miami

BIZ CPAs Miami is a bilingual accounting and advisory firm serving high-net-worth individuals, business owners, real estate investors, and family businesses across Florida, Latin America, and Europe. With 30+ years of experience, 200+ IRS cases resolved, and a team specializing in proactive tax planning, CFO advisory, and wealth strategy, we bring Fortune 500-level tax intelligence to the clients who deserve it.

bizcpasmiami.com  ·  (305) 593-2003  ·  bizcpas@bizcpas.biz