4 Health Insurance Options for Entrepreneurs


“But what about the benefits I’ll be giving up?” a soon-to-be entrepreneur asked.

“I’ve always gotten health insurance through my employer – what do I do as an entrepreneur?”

Entrepreneurs have to get creative when it comes to benefits traditionally provided by employers.

The self-employed population doesn’t have to go without, they just have to provide benefits traditionally offered in employment situations for themselves. 

Yeah, it’s a real bummer.

If you’re like me in start-up mode, shopping for health insurance is on the very bottom of my “entrepreneurial excitement list”; however, it’s super important.

Don’t go uninsured.

I repeat: DO NOT GO UNINSURED (this stems from not-so awesome personal experience).

There are a ton of health insurance options out there for the self-employed. It may take some digging to find an option that meets your current healthcare needs, however, it’s well worth the effort.

While I’m no insurance broker, I’ve spent the past few months filtering through hundreds of insurance options for entrepreneurs and hoped my own research may be of assist to other self-starters in the market for some medical coverage.   

Here are four options I found helpful during my own insurance search. Check them out and see if any fit your current situation:

Healthcare Marketplace

The Healthcare Marketplace, a.k.a. Obamacare, provides an assortment of health insurance options for the self-employed (click here to learn more about self-employed options). Fill out an online application at www.healthcare.gov to see if you qualify for premium tax credits and other savings on a health plan based on your income and household size. Be sure to note the enrollment period is only open from October to December – should you find yourself applying outside this window, there’s special enrollment options available.

Stride Health

Stride Health, Inc. is a California startup focused on connecting entrepreneurs and freelancers with health plans under the Affordable Care Act. Its tech platform is a LOT easier to use than www.healthcare.gov ‘s, plus its super tailored to the needs of today’s busy entrepreneur. It’s quickly becoming known as the health insurance go-to for members of our gig economy, recently receiving headlines as Uber’s health insurance broker.

COBRA Insurance

If you’re transitioning from a position with benefits to self-employment, consider purchasing COBRA coverage. This allows you to possibly hang on to your job-based health plan through COBRA, a federal law that allows you to continue paying for your employee health insurance for a limited time after your job ends. Depending on your current health insurance plan and your eligibility, this may provide you with quality coverage during this transition period.

Association Benefits

Some industry and entrepreneurial organizations offer health insurance options for members. It’s a great idea to check with your associations for coverage options. Many local Chambers of Commerce offer group health coverage, and the National Association for the Self-Employed offer health plan options. Be sure to shop around and consider the total cost (membership fees + insurance costs).


Starting your own business doesn’t have to mean giving up important benefits such as health insurance. There are a LOT of options available for today’s self-employed – the options listed above are just a few of the resources I found helpful on my own health insurance quest.

If you have any additional resource recommendations, feel free to include in the comments below.

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