6 Common Mistakes Families Make When Selling A Business

Selling a family business can be a monumental financial event and a major emotional transition. Such a sale often results in a significant liquidity event, presenting the family with new wealth management challenges. While the influx of capital can open up numerous opportunities, it also introduces potential pitfalls. Here are six common mistakes that families make when selling their business and here’s how you can avoid them:

1. Failing to Plan Ahead

In the swirl of getting a transaction done, it’s easy to be so laser-focused on getting the deal across the finish line that certain wealth planning steps are inadvertently missed or considered too late to be implemented. Before you sign a letter of intent to sell a business, there are a few key steps you should consider.

Solution: Transfer non-voting shares of a non-publicly traded company into an irrevocable trust. The irrevocable trust could be set up for the benefit of the wealth creator’s spouse, children, grandchildren, and future descendants. The shares would likely be transferred at a discounted value because the company is not marketable and not publicly traded. The value will likely be lower than it is when you actually have a concrete offer to sell the business. So then, at some future date, when you sell your business, the amount it sells for is now locked in because the trust owns the non-voting shares of the business. Additionally, that new value will be exempt from estate tax.

This leads to another point: If you live in a traditionally high-tax state like Connecticut, New York, New Jersey, or California, you should consider moving your tax domicile and residency to another state with no income tax such as Florida or Texas before selling your business. However, this process can take several months, so it’s important to map out a sufficient timeline to execute these steps successfully before the transaction closes.

2. Overlooking Tax Implications

The sale of a business can have significant tax implications, and without careful planning, families can find themselves facing substantial tax liabilities. For example, should you sell shares in the company or the business assets? Buyers and sellers can be at odds as sellers want to achieve capital gains, and buyers want to get a stepped-up basis for depreciation. They can be worked out by negotiating the sales price. Often, the excitement and relief of selling can overshadow the necessity of tax planning, which can lead to unfavorable financial outcomes.

Solution: Prior to the sale, collaborate with tax professionals to understand the potential tax impact and explore strategies for tax minimization. This might include timing the sale to coincide with specific tax advantages or utilizing trusts and other vehicles to manage the new influx of wealth. At my firm, planning in advance leads to advantageous timing that enables us to ensure that a client’s charitable intentions can achieve maximum tax benefits by offsetting ordinary taxable income.

3. Neglecting Estate Planning Updates

If estate plans were structured around the business as an asset, they need to be revisited once the company is no longer part of the family’s portfolio. Failing to update estate plans can lead to inefficiencies and conflicts within the family, especially regarding the distribution of the new assets.

Solution: Update estate planning documents to reflect the current state of family wealth. This may involve setting up trusts, revising wills, and ensuring that the distribution of assets aligns with the family’s current wishes. Most importantly, share details of the estate plan with your heirs while you’re still alive. That way, your heirs understand your thinking, can ask questions, and be prepared when the time comes.

The example of legendary investor Warren Buffet, 93, is instructive. He recently shared some details of his estate planning with the Wall Street Journal. He said he plans to leave nearly all his wealth to a charitable trust overseen by his three children (a daughter and two sons). “I feel very, very good about the values of my three children, and I have 100% trust in how they will carry things out,” Buffett told the Journal.

4. Not Reassessing Financial Goals

A family’s financial landscape changes dramatically after selling a business. What worked financially for the family when the business was operating might not be suitable for managing post-sale wealth. It's crucial for families to sit down with financial advisors to redefine their financial objectives, taking into account their current and future lifestyle, legacy considerations, and investment goals.

Solution: Engage with trusted advisors to establish new financial goals and create a strategic plan that aligns with the family’s values and new financial status. A family may want to consider establishing a family office structure to help its members navigate and manage their wealth or perhaps join an existing multifamily office that already has the staff, systems, and processes in place.

5. Making Hasty Investment Decisions

With a large amount of capital suddenly available, there might be a rush to reinvest this wealth. However, hasty investment decisions can lead to poor allocation of resources. The lack of a business, which previously might have been a major investment focus, can lead families to diversify their investments without adequate research or strategy.

Solution: Take a measured approach to investing the proceeds from the sale. Develop a comprehensive investment strategy with a wealth management advisor that considers risk tolerance, time horizon, and the family’s overall financial goals.

6. Underestimating Emotional and Psychological Impacts

Selling a family business is not just a financial transition but also an emotional one. The company often represents not just financial security but also a sense of identity and purpose for family members. Underestimating the emotional and psychological impact of this change can lead to challenges in adjusting to the post-sale reality.

Solution: Seek support from professionals specializing in family dynamics and wealth transition. Engaging in family governance structures can also help manage the emotional aspects and aid in the smooth transition of roles and responsibilities within the family.

Avoiding these common mistakes when selling a family business involves careful planning, professional guidance, and an understanding of the financial and emotional complexities involved. By addressing these areas proactively, families can secure their financial future and navigate the transition with confidence and clarity.