For many owners, the business is not just a company—it’s a lifetime of effort, risk, and sacrifice. At some point, though, the question becomes unavoidable:

“If I sell, how do I make sure I walk away on my terms—financially, personally, and for my family?”

Most owners focus on the headline sale price. But what really matters is:

• How much you keep after taxes and fees
• How and when you’re paid (cash vs. earnout vs. rollover equity)
• Whether your personal financial plan still works after you’re no longer in control of the business

This roadmap walks through the major phases of a typical sale process—from preparation through closing—and highlights where thoughtful planning (including tax mitigation strategies) can make a meaningful difference in your net outcome.

1. Start With the Big Picture: Your Goals, Timeline, and Net Proceeds

Before talking to buyers, it’s important to get clear on:

• Why you’re selling (retirement, burnout, diversification, health, succession, etc.)
• When you’d ideally like to exit (or step back from day-to-day)
• How much you actually need, after taxes, to support your lifestyle and goals

This is where personal planning and deal planning intersect. Key questions:

• What dollar amount do you need to be financially independent?
• How will a sale change your tax brackets, estate tax picture, and cash flow?
• Are there pre-sale strategies that could reduce the tax hit (for example, installment sale structures, Opportunity Zone funds, charitable remainder trusts (CRTs), bonus depreciation funds, or oil & gas programs)?

Getting clear on the after-tax number you need allows you to evaluate offers more objectively—especially when deals include earnouts, seller notes, or stock instead of pure cash.

2. Positioning the Business Before You Go to Market

Most of the value you capture in a sale is influenced long before buyers ever see your company.

A. Timing Your Exit

Timing is part market, part business, part personal.

• Market: Industry deal activity, interest rates, buyer appetite, and general economic conditions.
• Business: Growth trends, margins, concentration risks, key-person risk, and recent investments.
• Personal: Health, energy, family issues, and your openness to staying on for a transition period.

Often, owners benefit from a 1–3 year runway to clean up financials, strengthen value drivers, and address issues that would otherwise be used against them in negotiations.

B. Understanding Market-Based Valuation

A realistic valuation ranges from:

• Comparable company multiples
• Comparable transactions (M&A)
• Discounted cash flow (DCF) analysis
• Asset-based approaches in some industries

A valuation exercise can help you:

• See how buyers are likely to view your business
• Identify gaps that depress value (customer concentration, weak reporting, etc.)
• Decide whether to sell now, wait, or invest in improvements first

This is also a key moment to stress-test your financial plan:

“Given a likely valuation range, plus taxes, does this get me where I need to be personally?”

C. Preparing Financials That Buyers Can Trust

Buyers rely heavily on financial reports to assess risk, cash flow, and support their price. Owners commonly:

• Recast financials to show normalized EBITDA (removing one-time expenses and adjusting owner compensation)
• Clarify revenue quality (recurring vs. one-off, key contracts, churn)
• Tighten internal controls and reporting

Clean, well-presented financials:

• Build buyer confidence
• Reduce friction in diligence
• Support stronger valuations and better terms

D. Pre-Sale Due Diligence on Your Own Business

Many deals fall apart because surprises emerge during buyer due diligence. A pre-sale “internal” diligence review can uncover:

• Old or unfavorable contracts
• Unclear IP ownership
• Compliance gaps or licensing issues
• Litigation or contingent liabilities

Identifying these early allows you to:

• Fix what you can
• Disclose what you can’t fix in a controlled way
• Reduce the risk of last-minute price reductions

E. Legal and Tax Readiness

Two areas to review well before going to market:

• Entity structure: C corp vs. S corp vs. partnership and how each affects the tax treatment of the sale
• Deal form: Asset sale vs. stock sale and how that flows through to capital gains, ordinary income, and potential QSBS, Section 1202, or Section 1042 benefits where applicable

This is also where planning for tax mitigation strategies fits in:

• Installment sale arrangements to spread gains over time
• Opportunity Zone fund allocations to defer or reduce tax on certain gains
• CRTs to blend philanthropy with lifetime income and partial tax deduction
• Oil & gas / bonus depreciation programs where suitable, to generate large first-year deductions that may offset parts of the gain

The more work done here before a transaction, the more flexibility you’ll have when a real offer appears.

3. Going to Market: Positioning, Buyers, and Deal Structure

Once the business is prepared and timing feels right, the focus turns to how the sale is approached.

A. Bridging the Valuation Gap

It’s common for initial offers to come in lower than what an owner hoped for. Sometimes the gap is emotional; sometimes it’s rooted in real differences in assumptions (growth rates, capex needs, customer retention, etc.).

Tools that can help bridge the gap include:

• Earnouts tied to future performance
• Seller notes (you finance part of the purchase)
• Equity rollovers (keeping a minority stake in the new entity)

From a tax and planning standpoint, these structures can:

• Spread income over multiple years (similar to an installment sale)
• Allow you to participate in future upside
• Change when and how capital gains are recognized

Each structure has trade-offs in risk, control, and tax treatment.

B. Identifying and Highlighting Value Drivers

Buyers pay more for businesses that:

• Have recurring or contracted revenue
• Are not overly reliant on the owner
• Show consistent margins and growth
• Have systems and teams that scale
• Own key IP, data, or defensible advantages

Strengthening and documenting these value drivers:

• Reduces perceived risk
• Justifies higher multiples
• Often improves your negotiating leverage

C. Understanding Buyer Types

Different buyers see value in different ways:

• Strategic buyers may pay more for synergies (customers, product expansion, etc.)
• Financial buyers (PE, family offices) often focus on EBITDA growth and return on capital
• ESOP structures focus on financing capacity, stability, and long-term internal ownership

Each path may have different implications for:

• Your ongoing role
• Culture and employees
• Payment timing and structure
• Taxes and post-sale planning (e.g., Section 1042 opportunities in C corp ESOP sales)

Aligning the type of buyer with your goals matters just as much as the price.

4. Executing the Deal and Planning for Life After the Sale

A. Managing the Sale Process

A typical process includes:

• Preparing a confidential information package
• Responding to requests and questions
• Hosting management meetings
• Working through letters of intent (LOIs)
• Surviving confirmatory due diligence
• Finalizing purchase agreements

Throughout this, it’s important to:

• Keep running the business well (performance dips can impact value)
• Coordinate messaging with employees and key stakeholders
• Keep your personal planning and tax strategies aligned with shifting deal terms

B. Thinking Beyond Closing: Integration and Your Next Chapter

For the business, integration issues include:

• Leadership changes
• Communication with customers and employees
• Aligning systems and processes
• Preserving culture where it matters

For you personally, the questions shift:

• How will sale proceeds be allocated between liquid investments, real estate, alternative strategies, and tax-driven vehicles?
• What is your plan for replacing business income with portfolio and passive income?
• How will you manage concentration risk if part of the deal is equity in the buyer or rollover equity?
• How does this impact estate planning, gifting, and charitable objectives?

Post-sale planning can include:

• Diversified investment portfolios
• Tax-aware withdrawal strategies
• CRTs, donor-advised funds, and other charitable tools
• Additional tax mitigation programs in future years as laws and opportunities change

The more intentional you are before closing, the smoother your transition is likely to be.

Frequently Asked Questions - From a Wealth-Planning Perspective

How long does it usually take to sell a business?

A typical middle-market transaction often takes 7–12 months from formal preparation to closing, though complexity, readiness, and market conditions can shorten or extend that timeline.

What’s more important: the sale price or the tax structure?

Both matter, but owners frequently underestimate how much structure and tax impact their net proceeds. A slightly lower headline price with better tax treatment can sometimes leave you with more money than a higher price structured inefficiently.

Do I need audited financials to sell?

Audited financials aren’t always required, but higher-quality financials (reviews, strong internal controls, clean books) generally speed up diligence and improve buyer confidence.

What happens if I get an unsolicited offer?

You’ll still want to understand:

• How that price compares to likely market value

• How the deal is structured

• What it means for your tax picture and financial plan

  Even if you don’t run a full auction, a careful comparison of scenarios is essential.

When should I start exit planning?

Ideally 1–3 years before you expect to sell. Earlier planning increases your options for tax mitigation, estate planning, and value enhancement.

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General Disclosure

Please note that this information is for informational purposes only and does not constitute individual investment advice. It should not be relied upon as tax or legal advice. Consult the appropriate professional regarding your individual circumstances.

Diversification does not guarantee profit or protect against loss in a declining market. It is a method used to help manage investment risk.

Investing in DST properties and real estate securities involves material risks such as liquidity, tenant vacancies, market conditions, competition, interest rate risks, and the risk of losing the entire investment principal. DST 1031 properties are available only to accredited investors and accredited entities. Verify your accredited investor status with your CPA and attorney.

Not an offer to buy, nor a solicitation to sell securities. All investing involves risk of loss of some or all principal invested. Past performance is not indicative of future results. Speak to your finance and/or tax professional prior to investing. Any information provided is for informational purposes only. Securities offered through Arkadios Capital, member FINRA/SIPC. Advisory Services offered through Arkadios Wealth. Wealthstone Group and Arkadios are not affiliated through any ownership.