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The Tax Trap Most Business Owners Miss Before a Sale

Selling your business triggers one of the largest tax events of your life, and the right pre-sale plan can determine how much of the proceeds you actually keep.

3 MIN READ
November 13, 2025

Selling a business can create life-changing wealth, or a life-changing tax bill.

When owners fail to plan early, they often face:
• Large one-time capital gains taxes
• Higher NIIT (Net Investment Income Tax) brackets
• Missed opportunities for deferring or spreading gains
• Poor reinvestment decisions after the sale

A liquidity event is not just a transaction; it’s a tax event. With the right structure, you can keep significantly more of what you built.

The basics: What creates a tax bill when selling a business

There are two major tax drivers:
1. Capital gains tax - based on the difference between sale price and your basis.
2. Deal structure - asset sale vs. stock sale produces very different outcomes.

Most business owners underestimate how dramatically structure affects their tax burden.

The timing mistake

Tax planning done after signing a LOI is often too late.

By that point, owners usually lose access to:
• QSBS optimization
• Entity restructuring
• Gifting strategies
• Installment sale benefits
• Multi-year tax spreading opportunities

The best tax outcome often requires steps taken 12–36 months before the sale.

How to minimize taxes before a business sale

1. Model multi-year tax scenarios

Understand how different sale structures affect after-tax proceeds.

2. Explore entity changes early

Switching from C-corp to S-corp or vice versa may unlock major savings - but requires lead time.

3. Use income-smoothing strategies

Installment sales, earn-outs, or partial liquidity can reduce bracket spikes.

4. Leverage family transfer or gifting

For owners planning generational wealth, pre-sale gifts can reduce estate tax impact.

Common mistakes

• Waiting until due diligence to think about taxes
• Assuming your CPA alone handles deal strategy
• Not modeling how proceeds affect future retirement or investment decisions
• Ignoring state tax exposure
• Selling equity without reinvestment planning

Quick Answers: Business Sale Tax Questions

“Can I avoid capital gains tax completely?”
Rarely, but you can significantly reduce it with early planning.

“What’s the difference between asset sale and stock sale?”
Asset sales are typically more taxable for sellers; stock sales often reduce tax friction.

“How early should I start planning?”
Ideally 1–3 years before a sale.

Can Titan help with pre-sale tax strategy?

Yes. Titan advisors can help you:
• Model tax outcomes of different deal structures
• Coordinate planning with your CPA and attorney
• Build a reinvestment plan for post-sale wealth
• Avoid missed opportunities that cost owners thousands

Thinking about selling your business?
Talk to a Titan advisor before you sign anything.

About Titan

Titan is a modern Registered Investment Advisor helping business owners navigate complex pre-sale planning, tax strategy, and post-liquidity reinvestment decisions. Our advisors coordinate with your CPA and deal team to model tax outcomes, preserve more of your proceeds, and ensure your wealth is positioned for long-term growth after the sale.

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