Notes

Keeping your company independent when you retire, without selling to a competitor

Old Harbor Advisors — Wed, 07 Oct 2026 20:41:15 GMT

Owners often put it this way: “I’m ready to step back, but I don’t want to sell to a competitor. I want the company to keep its name, its people and the way it does business.” It is a reasonable goal. It helps to be specific, because independence can mean different things:

The MassCEO stipend: what it pays for, who qualifies and how to apply

Old Harbor Advisors — Wed, 07 Oct 2026 20:41:13 GMT

Since October 6, 2026, Massachusetts has offered to share the cost of taking a serious look at employee ownership. The Massachusetts Center for Employee Ownership, known as MassCEO, runs a Technical Assistance Stipend Program that can pay half of certain advisory costs for a company exploring a sale to an ESOP or a conversion to a worker cooperative. Its limits matter as much as the money.

Management buyout or ESOP? How two inside sales compare

Old Harbor Advisors — Wed, 07 Oct 2026 20:41:13 GMT

Many owners who want the company to stay in familiar hands narrow the choice to two inside buyers: the management team, or an employee stock ownership plan (ESOP) that holds shares for employees. Both can keep the company independent and reward the people who built it. They differ in who ends up owning the shares, how the price is set, how the purchase is paid for and what the company carries afterward.

The Section 1042 rollover: who qualifies, and what it defers

Old Harbor Advisors — Wed, 07 Oct 2026 20:41:12 GMT

Owners who look into selling to an ESOP soon hear about Section 1042. It can let a seller postpone capital gains tax on a sale to an ESOP, if a long list of conditions is met. It postpones the tax. It does not forgive it.

What an ESOP feasibility study covers, and what it does not

Old Harbor Advisors — Wed, 07 Oct 2026 20:41:10 GMT

Before an owner decides to sell to an ESOP, someone has to answer a practical question: could this work for this company, at a price and on terms the owner would accept? That is the job of a feasibility study. It is a test, not a decision.