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Sponsored by: Clearstead Trust
Updated: June 2, 2025

When Should a Business Owner Hire a Wealth Advisor?

The short answer: earlier than most do. Ideally, two to five years before a liquidity event or major inflection point. Hiring a wealth advisor early creates space to address long-term planning— tax, estate, investment, and personal—before urgency sets in. Below are five key questions that unpack why early engagement is so critical.

1. What’s the biggest downside to waiting until a sale is imminent?

Kenneth Morgan, President & CEO, Clearstead Trust

Waiting compresses your planning window and limits your options. Once a letter of intent (LOI) is signed, the opportunity to restructure ownership, transfer shares to trusts, or implement tax-saving strategies often disappears. This results in higher tax bills, less flexibility, and missed opportunities to shape your legacy. A wealth advisor, when brought in early, can recommend strategies and model various scenarios and ensures you’re optimizing outcomes—not reacting to them.

2. How can early planning improve after-tax outcomes?

With enough lead time, a wealth advisor can help you implement strategies that optimize wealth transfer, significantly reduce taxes and reflect your charitable intent. This might include setting up trusts as well as utilizing valuation discounts on transferred equity and lifetime gifting exemptions. If charitable giving is a priority, tools like donor-advised funds or charitable trusts are most effective before the sale. Proactive planning ensures more of your sale proceeds go to where you want—not the IRS.

3. What role does estate planning play before a business sale?

Your business is likely your largest asset—and selling it may be the event that creates true generational wealth. Even if your estate is below the federal tax threshold, thoughtful planning remains essential. Structuring ownership, titling assets, and clearly communicating your intentions protect both your plan and your people. But estate planning isn’t just technical—it’s emotional. You may have prepared wealth for your family—but have you prepared your family for the wealth? A good advisor helps guide those conversations and align your plan with your values.

4. What kind of planning is possible years before a sale?

Well before a buyer appears, you can begin shaping the impact of the eventual deal. This includes clarifying personal goals, forecasting future cash flow, building a diversified post-sale investment strategy, and assembling your advisory team. A wealth advisor helps coordinate your legal and tax professionals to ensure everything aligns. It’s not about timing the market—it’s about being structurally and emotionally ready when opportunity knocks. And in the case of an unplanned exit—due to illness, death, or partnership shifts—this planning becomes even more essential.

5. What qualities should an advisor have for this kind of planning?

Look for an advisor who understands the unique pressures of business ownership. You want someone who’s strategic, technically skilled, and relational—able to guide everything from deal timing and equity structure to liquidity planning and life after the business. Ideally, they bring both local presence and national resources, integrating tax, financial, and estate planning into a single cohesive framework.

Ready to Start the Conversation?

That’s exactly what we do at Clearstead Trust. Based in Portland, Maine, and supported by the extensive resources of Clearstead Advisors, we specialize in helping business owners navigate every phase of a liquidity event—before, during, and after the sale. From deal structuring and tax minimization to family preparation and philanthropic strategy, our team brings the foresight, tools, and experience to make your next chapter a success. If you’re beginning to think about a future sale, there’s no better time—or team—to start the conversation.

The information provided is general in nature, is provided for informational purposes only, and should not be construed as financial or legal advice. The views expressed by the author are based upon the data available at the time the article was written. Any such views are subject to change at any time. Clearstead disclaims any liability for any direct or incidental loss incurred by applying any of the information in this article. All financial decisions must be evaluated as to whether it is consistent with your objectives and financial situation. You should consult with a financial, tax or legal professional before making any decisions.