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Questions from owners near retirement

Retiring Business Owner FAQ

Straight answers for owners deciding what to do with their business as they approach retirement.

These are the questions I hear most from owners thinking about retirement. When you’d like to talk about your own business, start a confidential conversation, or read baby boomer business owners.

Straight answers

How do I retire from my business?

Decide your path — sell, pass down, sell to employees, keep with a manager, or close — then prepare the business to run without you. See retiring and selling my business.

How early should I start planning?

Several years before you want to retire. See business exit planning.

Should I close or sell?

Test the market before closing; many businesses are more sellable than owners think. See close or sell my business.

What happens to my employees?

It depends on the buyer and the terms. See protect your legacy when selling a business.

Will I have to stay after the sale?

Often for a transition period. See seller transition period.

How do taxes affect my retirement sale?

Significantly. Structure and timing matter; involve a CPA early.

What if my children don't want the business?

That’s common. An outside buyer or a management buyout may be the better succession. See business succession planning.

What will I do after I sell?

Plan it before closing. See life after selling your business.

Written by Ben Lovro

South Carolina operator based in Lexington. I've spent years buying real estate directly from owners through Cash Property Offers, I run my companies on the BOSS framework with an AI chief of staff, and I look at South Carolina businesses to acquire — as a buyer, not a broker. I built REI Boss, founded ClientPro.ai and wrote Skill Up. Read my story.

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