Not tax or legal advice. This article is general information based on my own experience selling a business. Every business and deal is different. Talk with your own CPA, attorney and financial advisor before acting on anything here.
The short answer
Besides selling to an outside buyer, you can sell to your management team (a management buyout), sell to your employees through an ESOP, hand the business to family through a sale, gifts or both, sell part and keep part, or wind the business down. Each has different tax, financing and people consequences, and each works better when the business doesn't depend on you every day.
1. Management buyout
Your leadership team buys the business, usually with a bank loan plus a note you carry, which means you're paid part of the price over time. It keeps the culture and the people. The risk is that being paid in full depends on their success.
2. Employee stock ownership plan (ESOP)
The company sets up a trust that buys your shares on the employees' behalf, usually with borrowed money and often with a note from you. The company generally has to be a corporation, not an LLC taxed as a partnership. There can be significant tax advantages for you and the company, depending on how it's structured. For example, owners of C corporation stock who have held it for at least three years and sell to an ESOP that owns at least 30% of the company afterward may be able to defer capital gains tax by reinvesting in qualifying securities within a set window. The rules are strict, so get specialized advice. ESOPs are also complex, cost real money to set up and run, require an independent valuation every year, and tend to fit larger, stable companies with enough employees and profit to support them.
3. Family succession
A transfer to family can be a sale, a gift or a mix, often using the trusts and gifting strategies described in taxes when selling a business. It works best when the next generation actually wants the business and when the plan starts years ahead, before the value rises.
4. Sell part, keep part
Some owners sell a majority stake to private equity and keep a minority stake. You get cash now and a possible second payday later if the business keeps growing.
5. Winding down
Closing the doors is sometimes the only option left, and it's usually the most expensive one for you and for the people who work for you. See when your kids don't want the business for a story about why.
The common foundation
Every one of these needs a business that doesn't depend on you every day, with clean numbers and a team that can carry it, whether the next owner is a stranger, your managers, your employees or your kids.
One thing to try this week
Pick the two options that feel most like you, then ask your CPA and attorney what each would take.
Related questions
Who would buy my business? Strategic, financial and individual buyers
What will the tax bill be when you sell, and when is it too late to change it?
This article is for general information only and is not tax, legal, investment or financial advice. RealDeal360 is not your attorney, accountant, tax advisor or investment advisor.