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March 25, 2026

Business January 10, 2025 8 mins read

Now’s the Best Time to Sell a Business and Retire, but Many Baby Boomers Are Waiting

Business ı By Jeff Watterson

3,599 0 Comments

Demographic researchers have warned for decades about baby boomers leaving the job market, leaving an extreme amount of job vacancies for the GenX and millennials to try and replace.  As the tidal wave of retiring baby boomers approaches, there will not be enough job seekers to fill their predecessor’s shoes. The same will be true for retiring business owners.

Economists were first predicting the tidal wave of baby boomer retirees to begin around 2007; right when the sub-prime lending bubble began its collapse; putting hundreds of thousands of Americans out of their homes. To add insult to injury, Bernie Madoff was exposed for his nearly 50-year Ponzi scheme in 2008. Americans who had saved up a nest egg in preparation for retirement suddenly had the rug pulled out from them, with no choice but to start over in a failing economy mere years before their traditional retirement date. Many couldn’t leave the job market if they wanted to. Now, economic reports reflect a recovering economy yielding positive returns, and baby boomers have not left the workforce in the droves once speculated; but the tipping point is inevitable. For the baby boomer business owners, the current economic uptick provides many compelling reasons to push off retirement, but some believe they are missing out on a historic opportunity to sell at premium rates.

Just as those who survived the Great Depression, small-to-moderate business owners today are particularly hesitant when it comes to selling their businesses. It’s understandable. In recent years, they’ve seen the biggest Ponzi scheme in history, a sub-prime lending crisis that caused an epidemic of housing foreclosures, giant banks and insurance companies collapse, and scandals in the financial sector such as Martha Stewart’s insider trading and the fall of Enron. Additionally, medical advances have allowed people to stay active and productive longer in life. It makes sense to hang onto a thriving business and collect a few more years of steady income. But successfully selling a business is as much about market timing as selling any other asset like stocks or real estate. If baby boomers should know one thing, what goes up, must come down. All business is cyclical.  While the economy is experiencing a quick recovery, many experts are encouraging business owners to consider their exit strategy seriously.

As of the summer of 2017, several categories of business acquisition buyers are actively looking for opportunities.  From private equity groups, to companies looking to grow and expand, and even the individual entrepreneur who is looking to acquire their first operation; there is clearly more buyers than sellers.  This leaves mergers and acquisition advisors hunting for quality businesses to feed the frenzy of the market.  Business owners have the opportunity to take advantage of a wide-open sellers’ market where recently completed private equity deals included companies with as low as $500k of EBITDA. Other operating companies are searching for competition and synergistic companies who have even less cash flow.  Those business owners who are experiencing the good times now can leverage their value and capitalize on high profits that aren’t guaranteed later. The fear many have in the M&A market is that too many business owners will get caught investing in their company for another decade while they ride out the next economic disruption wave, and they will be forced to sell their brainchild for pennies on the dollar.

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Jeff Watterson
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Jeff Watterson

Jeff Watterson is a journalist that focuses on politics, investigative journalism, and technology news. When Jeff is not writing, which is his hobby, he enjoys fishing and hunting.

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