Five wealth planning strategies for navigating a successful business sale

For many business owners, the business isn’t just an asset — it’s a reflection of your identity, your life’s work and often your largest source of wealth. So, when it comes time to sell or transition a closely held company, it’s rarely just about the numbers. It's about control, legacy, family, timing and taxes — and it’s deeply personal.

If you're already reviewing a letter of intent (LOI), it may be too late to start planning. Ideally, conversations around liquidity, estate planning and aligning business and personal goals should happen well before an offer is on the table.

Here are five key strategies to help you prepare and maximize the outcome of a sale:

1. Align your business and personal goals

Many owners make the mistake of separating business planning from personal financial planning. In reality, they can be inseparable.

Ask yourself:

• What does my ideal life look like after the sale?
• How much do I need — after taxes — to maintain that lifestyle?
• Do I want to launch something new, invest in others or give back?

Example: A manufacturing company founder received a $60 million LOI only to realize the net proceeds wouldn’t support his retirement vision. That gap forced him to delay the sale and restructure the business to better align financial outcomes with personal goals.

2. Start estate planning before the LOI

This point cannot be stressed enough: Estate and tax strategies should be implemented before an LOI is signed.

Once an offer exists, the IRS considers the business’s value “known,” which dramatically limits your ability to shift wealth out of your estate at a favorable valuation.

Example: A tech entrepreneur gifted minority shares to a dynasty trust before any formal offer. When her company later sold for $180 million, nearly $40 million in value remained outside her taxable estate — avoiding future estate taxes altogether.

3. Retain control while transferring wealth

Transferring ownership doesn't mean giving up control. Strategies like grantor retained annuity trusts (GRATs), spousal lifetime access trusts (SLATs) and nonvoting share structures allow owners to shift value out of their estate while retaining decision-making authority.

Example: A beverage company owner transferred non-voting shares to a family trust but retained all voting rights. He preserved control of the business while removing tens of millions in future appreciation from his estate.

4. Look beyond the sale price

Selling a business is a pivotal moment, but maximizing value involves more than just negotiating a number.

Key considerations:

• Tax strategy: Are you selling stock or assets? Each has very different tax implications.
• Income timing: Can you spread gains over time or qualify for the qualified small business stock (QSBS) exclusion?
• Diversification: How will you invest proceeds to match your risk profile, lifestyle and philanthropic goals?

5. Avoid the post-sale diversification trap

Many owners are unprepared for what comes next. You’ve spent decades building a single illiquid asset. Post-sale, you may find yourself sitting on tens of millions in cash — without a plan.

One big mistake may be rushing into new private investments, real estate or “friends’ deals.” While those can play a role, you’ve just exited one high-concentration bet — don’t leap into another without a strategy.

Why marketable securities matter:

• Liquidity for lifestyle, philanthropy and flexibility
• Diversification across industries, asset classes and geographies
• Tax efficiency via tools like tax-loss harvesting, municipal bonds and structured notes
• Transparency so you can see and manage what you own

Example: A healthcare entrepreneur sold her company for $100 million. Until then, she had no brokerage account — just her business and real estate. By allocating 80% of her post-tax proceeds into a portfolio focusing on income generating and tax advantaged investments, she gained a steady income, reduced taxes and liquidity to fund her next venture — without the pressure to chase the next “big” deal.

The bottom line: timing is everything

Investment bankers focus on the transaction. Attorneys focus on risk. CPAs focus on compliance.

A seasoned wealth advisor ties it all together, helping you pause the deal frenzy long enough to ask:

• Is this the right time?
• What does this mean for my family?
• Can I live with this decision for the next 30 years?

A wealth advisor can also coordinate your broader team — estate attorneys, tax specialists, M&A advisors—so your strategy is cohesive and aligned with your long-term goals.

A liquidity event can be an empowering moment of your life — or an overwhelming one. Better outcomes can come from early planning, clear priorities and expert coordination.

Owners who waited too long or tried to do it alone may regret it.

If you're considering a business sale or transition in the next five years, now is the time to engage a wealth advisor. The right planning today will help determine how fully you enjoy the life you’ve spent decades building.

Questions? Connect with our team to learn more.

This information does not constitute investment advice and is not an offer to buy or sell a security. The material is provided for general information and educational purposes and is based on information provided to us by sources deemed to be reliable. All expressions of opinion are subject to change without notice in reaction to shifting market conditions. Examples provided are for illustrative purposes only and not intended to be reflective of results you can expect to achieve. Past performance is no guarantee of future results and asset values will fluctuate with changing market conditions. There is no guarantee that the views and opinions expressed in this document will come to pass. Investing in the market involves gains and losses and may not be suitable for all investors. All investments are uninsured and can lose value. AI (artificial intelligence) was utilized to assist in the creation of this marketing piece.

Baker Tilly Wealth Management, LLC (BTWM) is a registered investment advisor. Reference to registration does not imply any particular level of skill. BTWM does not provide tax or legal advice. BTWM is not an attorney. Estate planning can involve a complex web of tax rules and regulations. Consider consulting a tax or legal professional about your particular circumstances before implementing any tax or legal strategy. The information provided here is of a general nature and is not intended to address the specific circumstances of any individual or entity. In specific circumstances, the services of a professional should be sought.

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