When Health Insurance Becomes Unaffordable
Business owners have much at stake—maybe more than they realize—in the battle over expiring health insurance subsidies. Are you confronting rate increases? Do you know what you’re going to do?
Here are today’s highlights:
Ami Kassar says AI has already transformed his business—but now comes the hard part.
The Supreme Court justices seemed skeptical of President Trump’s tariff arguments.
Gene Marks reminds that severance payments are far less expensive than legal fees.
There were more private company job cuts in October than we’ve seen in more than two decades.
HEALTH INSURANCE
Surging health insurance bills are a tough pill to swallow for business owners: “John Cleveland is ready to pay a lot more for his health insurance next year. He hasn’t forgotten the pile of hospital bills that awaited him after he had a seizure while tending to customers in his Austin, Texas, barbershop four years ago. Once doctors hurriedly removed the dangerous tumor growing on his brain, a weeklong hospital stay, months of therapy, and nearly $250,000 worth of medical expenses followed. The coverage he has purchased for years through the Affordable Care Act marketplace covered most of those bills. ‘That saved my ass,’ said Cleveland, who owns three barbershops across the city.”
“Even with Cleveland’s monthly premiums expected to soar next year — from $560 to about $682 — he will still sign up for a plan that requires him to shell out $70 if he sees a doctor and 50 percent of the cost for any emergency room visits. Still, Cleveland is most worried about some of his employees, who might risk going without insurance once they see the high prices.”
“Small-business owners are among those who stand to lose the most should Congress let the additional, generous federal subsidies put in place during the covid-19 pandemic lapse. The looming change threatens not only their own coverage but also that of their employees, who often depend on marketplace coverage.”
“Most of the roughly 20 employees who work on Justin Miller’s 113-year-old family fruit farm in rural Northern California purchase coverage through the Obamacare marketplace. He’s agonizing over what it could mean if health insurance through the marketplace becomes unaffordable for his employees. He fears they might consider leaving his farm for a job that comes with health coverage.”
“‘Being a small-business owner, especially in a field like ours, where it is tough work and we really understand how hard everybody works, we have to look everybody in the eyes every day,’ Miller said. ‘Knowing that they’re going to have to pay $4,000 or $5,000 more a year to stay on their insurance is a tough pill to swallow.’ Miller says he already pays a minimum wage of $22.50 and provides sick leave, vacation, retirement, and employee housing benefits. Adding health insurance for his employees, he said, would be too costly to keep his farm in business.” READ MORE
THE 21 HATS SOUNDING BOARD
How is your business handling the rise in health insurance rates? Have you received your quotes for 2026? What are your plans? JOIN THE CONVERSATION


