Boomers Can Sell Their Businesses More Lucratively Thanks To Trump's New Tax Law

Small business owners preparing to exit their companies in the coming years could save millions in taxes under provisions of President Donald Trump‘s One Big Beautiful Bill Act, which was enacted in July. 

While the law particularly benefits AI startups positioning for lucrative exits, business owners across multiple economic sectors stand to realize substantial tax savings when selling their companies. Eligibility requirements exist, but many small businesses considering exit strategies should investigate the opportunity, says CNBC. 

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Baby Boomers Lead Exit Planning Push

Older business owners most frequently contemplate selling, data from the Exit Planning Institute showed. The 2023 report shows 58% of baby boomers plan to sell their businesses within five years, compared to 39% of Generation X owners and 48% of millennials. Exit planning ranks as a top priority across all entrepreneurial generations.

Enhanced QSBS Benefits Lower Barriers to Qualification

The new law increases the tax-free gain cap to $15 million for qualifying C corporations issuing stock after July 4, up from the previous $10 million threshold. The legislation also reduces the required holding period to three years from five years, according to CNBC, while adding partial tax benefits for owners selling after three or four years.

This shortened timeline creates opportunities for businesses interested in selling sooner than five years that previously considered qualified small business stock inapplicable. Additional businesses now qualify after the asset cap rose to $75 million from $50 million, says CNBC.

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“Before the Tax Cuts and Jobs Act and the One Big Beautiful Bill Act, it wasn’t attractive for small businesses to be C corps, and many still aren’t organized this way,” Crew Advisors Wealth Strategist Corey Pederson told CNBC.

Older business owners need careful consideration, especially since 27% of boomer entrepreneurs report being unprepared with formal valuation plans and 9% lack adequate estate plans, according to the Exit Planning Institute. 

Even owners who previously considered and dismissed C corporation conversion should reconsider, HB Wealth Senior Wealth Advisor Natalie Whelton told CNBC.

Iowa Business Leaders Praise Economic Impact

Republican leaders traveled across Iowa in August to promote the economic benefits the One Big Beautiful Bill is delivering to small business owners throughout the state. Sen. Joni Ernst (R-IA), Rep. Ashley Hinson (R-IA), and Small Business Administrator Kelly Loeffler gathered with local business leaders in Iowa for a roundtable discussion focused on the new legislation’s impact, KCRG-TV reported. Small business owners who participated in the morning event expressed strong support for the law, citing multiple ways it will benefit their operations and communities.

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“What we are hearing from small businesses is that this is so much better for their financial planning, for their future and reinvestment in their own businesses,” Ernst told KCRG-TV. 

J.P. Gasway Company finance chief Brent Gasway explained the direct impact on his company’s bottom line. “The biggest impact to us will be increased sales to our manufacturing customers,” he said.

Allegra Marketing Print Mail owner Eric Van Kerckhove discussed how the legislation affects businesses like his. “It’s not just so we can take that money home and buy a bigger home or go on a fancy vacation, but a lot of us are philanthropic at heart so it allows us to give back to our community,” he told KCRG-TV. 

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