Selling your business is one of the biggest financial turning points in your life—but without planning, you could lose 30–40% of its value to taxes. In this episode, Carol Dewey breaks down how to turn tax traps into tax savings so you can exit with confidence and without regret.

Carol shares real-life case studies of business owners who reduced their tax bills by millions using strategies like installment sales, charitable remainder trusts, deferred sales trusts, opportunity zone funds, and wealth replacement trusts. You’ll learn why the time to plan is before you sell—not after the ink is dry.

Whether you’re five years away from selling or already considering an exit, this episode will help you protect your wealth, provide for your family, and build a lasting legacy.

What You’ll Learn in This Episode:

• Why selling your business without tax planning could cost you up to 40% of its value
• How capital gains taxes and depreciation recapture impact your proceeds
• Deferral strategies that give you more time, flexibility, and income control
• The role of wealth replacement trusts in protecting your heirs
• The 3 essential steps to take if you’re within five years of an exit

Resources and Links:

📘 Free Download: 8 Key Drivers of Company Value

📅 Book your Complimentary Lifestyle & Legacy Assessment: Schedule with Carol

💬 Website: www.perpetualwealthfinancial.com

💬 LinkedIn: Carol Dewey

🎧 Listen & Subscribe: Available on Apple Podcasts, Spotify, and YouTube

Are you ready to head down the

path to an abundant retirement?

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We're tackling the topics of the

mind of the modern retiree here.

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I'm navigating an abundant retirement

radio, and now your host, Carol Dewey.

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Welcome back to Navigating

Abundant Retirement Radio.

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I am your host, Carol Dewey, and today

we're tackling one of the biggest

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financial turning points in a business

owner's life, the sale of your business.

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Here's the question you

need to ask yourself.

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Would you rather leave 30 to 40% of

your business value on the table or

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redirect that wealth towards your

retirement, your family, and your legacy?

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In this episode, we'll dive into

capital gains mitigation, deferral

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strategies, and wealth replacement trust.

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Plus I'll share real life case

studies of business owners who

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turn tax traps into tax savings.

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If you're even thinking about an exit

in the next five years, this is one

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episode you can't afford to miss.

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First, let's be honest

about what's at stake.

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When you sell your business,

the IRS and state governments

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line up to take their share.

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You may face capital gains tax on

the appreciation of your company.

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Depreciation, recapture if

you've written off assets.

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State taxes, depending on

where you operate or reside,

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and net investment income tax.

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If your adjusted gross income

crosses certain thresholds, when

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you add it all up, it's not unusual

for a business owner to lose up to

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40% of the sale proceeds to taxes.

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So here's a case study.

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A dentist in the Midwest sold her practice

for $5 million without tax planning.

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She owed 1.7

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million in taxes.

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Money that could have provided

lifetime income for her and her spouse.

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Fortunately, with a team approach, she

was able to use deferral strategies

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to cut her tax bill nearly in half.

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The key lesson, once the ink is dry on

the sales contract, your options narrow.

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The time to plan is before you sell.

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So how do you keep more

of what you've built?

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The first step is under

understanding capital gains.

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This is the tax you pay on the

profit from selling your business.

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The rate can range from 15% to 23.8%

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federally plus state taxes.

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But here's the good news.

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With intentional planning,

you can mitigate or even

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eliminate a significant portion.

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Some of the strategies include installment

sales, that spreading payments over time

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allows you to spread out tax liability

and potentially stay in a lower bracket.

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Charitable remainder trusts by

placing part of your business

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in A CRT before the sale.

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You can defer capital gains, take a

tax deduction, and still receive income

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for life and opportunity zone funds.

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Ruling part of your gain into

designated zones can defer

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and potentially reduce taxes.

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Here's another case study with

the Kentucky manufacturer.

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A Kentucky business owner sold his family

manufacturing business for $12 million.

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His accountant had him set up for a

straight sale, which would've triggered

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nearly a $5 million in in taxes.

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After a consultation, he chose a

combination of an installment sale

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and a charitable remainder trust.

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His, um.

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Upfront tax bill dropped to under $2

million, freeing an additional $3 million

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for reinvestment and income planning.

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Now that's the power of planning.

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Not every business owner wants to give

up control of their money, and that's

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where deferral strategies can come in.

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Some examples might be structured sales.

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Think of this as a

prearranged installment sale.

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With an insurance company, you

can customize income streams

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while spreading taxes over years.

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Deferred sales trusts these allow

you to sell your business, transfer

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proceeds to a trust and defer taxes

while reinvesting in other assets.

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And of course, 10 31 exchanges.

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For real estate heavy businesses,

you can roll gains into new property

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investments and defer taxes indefinitely.

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Deferral is powerful because it gives you

time, and time, gives you options, whether

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it's reinvesting, smoothing out income

for Medicare thresholds, or creating

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generational wealth, one of the most

overlooked tools in advanced planning.

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Is the wealth replacement trust.

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Now here's how it works.

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Let's say you choose a

charitable trust to defer taxes.

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That means part of your estate

eventually goes to charity,

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but what about your heirs?

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A wealth replacement trust funded

with life insurance ensures

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your children or grandchildren

replace that wealth tax free.

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I've got another case study to share here.

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The franchisee.

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A couple who own several franchise

restaurants decided to exit.

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They set up a charitable remainder

trust, which gave them lifetime income

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and deferred their capital gains to

ensure their heirs didn't feel left out.

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They used a wealth replacement

trust to leave a tax-free $5

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million legacy to their children.

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The result they lived generously

reduced taxes, supported a

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charity they cared about and still

passed wealth to their family.

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That's a win on every front.

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Now let's pause here and

speak directly to you.

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My ideal client.

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You're not just trying to sell a business,

you're trying to protect a legacy.

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You spent decades building something

valuable, and now you wanna make sure

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the rewards serve your family, your

retirement, and your greater purpose.

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But your pain points are clear.

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You don't wanna lose control

of your exit to taxes.

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You're unsure if your CPA is

equipped for advanced strategy.

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You're worried about timing sell

too soon or too late, and you could

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leave millions on the table and

your aspirations are equally clear.

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You wanna keep more of what you've earned.

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You wanna ensure your family and causes

you care about benefit, not just the IRS.

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You want to exit with peace of mind.

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Without regret.

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This is where a coordinated team,

financial planner, tax strategist,

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and estate attorney comes into play.

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And this is exactly the role we

play at Clarus Advisory Partners

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and Perpetual Wealth Financial.

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So what's next?

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If you're within five years of a

potential exit, the time to plan is now.

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Here are three action steps.

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First, get a business valuation.

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Know your baseline.

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You can't plan effectively without

knowing what your company is worth today.

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Second, assess your tax exposure.

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Work with a strategist who can

model your potential tax bill

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under different scenarios.

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And third, design a custom exit plan.

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Don't settle for cookie cutter solutions.

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Your plan should fit your goals

for income, legacy, and lifestyle.

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Selling your business is one of the most

important financial events of your life.

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Done right, it can fuel your

retirement, empower your family,

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and build a lasting legacy Done

wrong, it can leave you with regret.

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And the IRS With a windfall,

the choice is yours.

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Plan early and you can

exit without regret.

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Thanks for tuning in to Navigating

Abundant Retirement Radio.

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Remember, selling your business

doesn't have to mean giving away a

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third of your life's work to taxes.

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With proactive planning, you can exit

with confidence and without regret.

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If today's discussions sparked

questions for you, visit

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www.perpetualwealthfinancial.com.

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To schedule your lifestyle and legacy

assessment, or call us directly at

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(877) 434-6243, and don't forget to

subscribe so you never miss an episode.

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Designed to help you protect your wealth,

your business, and your family's future.

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Until next time, I'm Carol Dewey,

helping you navigate with intention,

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and I will see you again next week.

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You should consult a financial advisor

familiar with the specific circumstances

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of your unique financial situation

before making any financial decisions.

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Nothing in this broadcast constitutes

a solicitation for the sale or purchase

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of any securities, any mentioned

rates of returns for our historical

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or hypothetical in nature, and are

not a guarantee of future returns.

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Carol Dewey is an investment

advisor, representative of Perpetual

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Wealth Financial, a Florida

registered investment advisor firm.