Wealthyist E79 | Selling Your Business: Is Your Company Worth What You Think? Don't Be Surprised

Most owners know they should have an exit plan. Fewer than half do, usually because they do not know where to start. Brian Lambourne talks with Amy Kiiskila, Director of Wealth Strategies for Annex Private Client, about the do’s and don’ts of selling a business.

The starting point is a decision tree, not a signed deal. Internal sale to key employees or family, third-party buyer, or private equity. You do not need the answer today. You do need the universe of options, and a team in place early: attorney, CPA, and financial advisor. The advisor is the role owners most often skip. That is a mistake. The sale price is not the lifestyle. After taxes, debt, and what the family actually spends, the check may not be enough, and money parked in a money market because no one planned the next chapter is a common result.

Family businesses add another layer. Do not assume what active and inactive children want. Selling to one child so siblings are not disadvantaged can work, but only if you have already worked through how that child pays for it and how the family functions afterward.

The biggest advantage is time. A four- or five-year runway means more control over structure, asset sale versus stock sale, charitable planning, and gifts to children or trusts. For higher-net-worth owners, gifts made far enough before a sale can move future appreciation out of the estate. The 2026 estate-tax exemption is $15 million per person, but a valuable business can still make estate tax the issue, and that planning is timing-sensitive. Show up two months before closing asking to “save taxes now,” and the buyer has the leverage.

What not to do: rely on a verbal agreement, download a form and call it a sale, or treat TikTok, YouTube, or ChatGPT as the plan. AI can surface useful questions. It is a starting point, not a valuation or a legal opinion. Owners routinely misjudge what the company is worth. A valuation expert, investment banker, or accountant running real multiples takes the emotion out of the number.

Start earlier. Document the plan. Put the team in the room before you pick a buyer.