When should I start exit planning?
Commonly three to five years before an intended transition, because the levers that improve an outcome need time: cleaning up financials, reducing owner dependence, resolving customer concentration. Buy-sell and valuation review, though, should not wait for a planned exit at all. Death, disability, and partner disputes do not schedule themselves.
Our buy-sell has a fixed price set years ago. Is that a problem?
Usually, and it is a common finding. A price that was reasonable when signed can drift badly from current value, and it typically binds anyway. Depending on the direction of the gap, either a departing owner or estate receives far less than the interest is worth, or the surviving business owes far more than it can fund. Most modern agreements use a defined formula or periodic appraisal instead.
Does company-owned life insurance affect the value of my estate?
It can. In Connelly v. United States (2024), a unanimous Supreme Court held that life insurance proceeds a corporation receives to buy back a deceased shareholder's stock count toward the company's value for federal estate tax purposes, and that the buyback obligation does not offset them. Some company-owned arrangements can therefore produce a larger taxable estate than the owners expected. How it affects your agreement is a question for your attorney and CPA.
Should the owners buy the shares, or the company?
In a cross-purchase, the individual owners buy the departing interest directly; in a redemption, the company buys it back. The choice affects who holds and pays for the funding, the surviving owners' cost basis, and, after Connelly, how insurance proceeds interact with estate valuation. Hybrid structures defer the decision to the triggering event. The right answer depends on the number of owners, entity type, and any funding already in place.
What triggering events should a buy-sell cover?
Death is nearly always addressed. Frequently missing: disability, divorce, personal bankruptcy, loss of a required license, voluntary departure, and termination for cause. The divorce provision matters more than owners expect, because without one a former spouse can end up holding an ownership interest. Deadlock provisions matter in fifty-fifty arrangements.
What is my business actually worth?
For most closely held operating companies, value is commonly expressed as a multiple of normalized earnings, adjusted for owner compensation, non-recurring items, customer concentration, working capital, and how dependent the business is on you personally. Multiples vary substantially by industry, size, and buyer type. A number produced for internal planning is not a formal appraisal supportable for estate or ESOP purposes, so we coordinate the appropriate engagement rather than estimate.
Is selling to an ESOP a realistic option?
For some companies, yes. An ESOP can provide liquidity where no attractive third-party buyer exists, keep the business locally owned, and, for certain corporations, allow a selling shareholder to defer the gain by reinvesting the proceeds. It also carries ongoing cost, fiduciary obligations, an annual independent appraisal, and a repurchase obligation that grows over time. It suits companies with steady cash flow and a management team able to run the business without the seller. See our
ESOP participant planning page for the participant side.
When should charitable planning happen relative to a sale?
Well before a letter of intent. Strategies that involve contributing an interest in the business ahead of a sale depend on the gift being complete and unconditional before the sale is effectively negotiated. Waiting until a deal is nearly done can cost the intended benefit, because the income is treated as already earned.