COBRA isn’t real, like Santa Claus and the Tooth Fairy. I’m not saying that companies don’t have to follow the law. I’m just saying that there isn’t a basket of COBRA snakes in Washington, DC administering your health insurance like the IRS administers taxes.

The metal tiers are more about risk tolerance than coverage: Lower tier = pay less monthly, but pay more when you go to the doctor Higher tier = pay more monthly, but pay less when you go to the doctor

Many midwestern states have reciprocity agreements where each state agrees to let the other handle payroll taxes. Without keeping score. It’s the state tax equivalent of saying, “It’s cool, bro. I know you’ll get me next time.” 

Life and AD&D is one of the last benefits that small businesses and startups add to their offerings. It’s a real bummer to talk about. And unlike short-term disability, the people who need it don’t complain if you don’t have it. But here are some reasons you should care about life and AD&D insurance.

A health savings account (HSA) is an interest-bearing bank account where you can put pre-tax dollars in and use them for healthcare costs. But to be eligible to contribute to an HSA, you need a special high-deductible, high-premium health (HDHP) health plan.

I’m talking about the small business where an employee is on their spouse’s insurance or a Marketplace plan and the company just reimburses them for all or part of the premium like a regular business expense. You're not supposed to do that.

A non-birth parent who was born in Argentina, had French citizenship, but was on a work visa in the UK sponsored by a US-based company.

The One Big Beautiful Bill Act (OBBBA) increased your health insurance premiums in two meaningful ways: It cut pandemic-era premium tax credits (which help the working poor get healthcare) and it cut funding for Medicaid (which pays for healthcare for the very poor).

But if you have a product or agency that was created to manage private and sensitive data, it is incumbent on YOU to create processes and tools to help users handle that information properly.