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The Entrepreneur's Guide to Health Insurance

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By Jake Nordquist   |    October 8, 2018   |    2:59 PM

A Guide to Health Insurance for Small Business Owners

Whether you're a small business owner with employees, or a self-employed entrepreneur, handling your own health insurance can be complicated. While there’s no one-size-fits-all health insurance solution that will work for every business, reading this quick guide will ensure you’re aware of the available options.

The best health insurance options for entrepreneurs

There are six main options for anyone seeking their own health insurance, with varying levels of affordability, coverage, and ease of use:

1. Health Insurance Marketplace (

This is the most popular option for the self-employed, though you need to select a plan during the open enrollment period. The 2019 Open Enrollment Period runs from Thursday, November 1, 2018, to Saturday, December 15, 2018.

You may also be eligible for tax credits and other savings options — create an account and complete an application to learn more.

2. Health Insurance Companies

You can also purchase health insurance directly from insurance companies like UnitedHealthcare and Cigna. There are a variety of plans and options, so you’ll have to spend some time researching and comparing.

3. Health Insurance Brokers

Health insurance brokers save you time and money by doing the heavy lifting on your behalf. First, they’ll learn about your needs, budget, income, and more. Then they’ll get to work aggregating plans so that you can make quick comparisons. A health insurance broker should never charge you a fee, because they’re paid by the insurance companies they represent.

A search for “health insurance brokers near me” is a great start, or you can visit a website like HealthMarkets to find an agent.

4. Freelancer and Industry-Specific Groups

Certain industry-specific organizations, like the Freelancers Union, connect members with more affordable health insurance plans. This option isn’t available for every industry, but a quick online search for options in your field makes it easy to see what’s out there.

5. Association Health Plans

Thanks to a recent Executive Order, small businesses (and the self-employed) can combine forces to obtain healthcare coverage for members, just like a large employer who gets better rates with a group plan. Learn more here.

6. Healthcare Sharing

Healthcare costs are shared amongst members in these organizations, which are often faith-based. Liberty HealthShare is one option, and members are required to uphold specific biblical values.

KNEW Health is another cost sharing organization slated to become effective on January 1, 2019. As with any health insurance plan, reading the fine print is key. With KNEW, there’s an emphasis on healthy lifestyles, and people with pre-existing medical conditions that require ongoing care aren’t ideal candidates for the plans that will be offered.

Am I required to purchase health insurance?

As of 2019, forgoing health insurance doesn’t equate to breaking the law (the rules are different for business owners who have employees, however). By lowering the tax penalty to $0, the Tax Cuts and Jobs Act of 2017 effectively repealed the individual mandate as of 2019.

Still, not having health insurance is a big financial risk. One illness or injury could easily lead to astronomical bills, so weigh your options carefully before deciding not to buy health insurance.

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