Navigating Health Insurance for Small Businesses

I’ve recently undertaken the arduous task of finding health insurance as an entrepreneur. I’ve been in charge of managing health insurance for employees a few times in my career, and even selected a policy and onboarded the staff at a nonprofit. I can’t say the process has gotten any less confusing no matter how many times I’ve delved into it, so I'm here to give you some tips and resources to help. I hope I can save you some time and stress with this overview of what I found while searching for health insurance for myself.

I’ll preface this with the fact that I am in no way an expert in this, but will direct you to helpful resources for insurance options specifically for contractors, individuals, and small businesses. It helps to have a reliable agent that will stick with you and answer questions, as well as help you onboard and removed staff members as things change. It's important to do your best to choose an option that works best for your entire staff since premiums can be high for smaller groups, and some vary depending on the age, health and number of applicants.

Where to Start

Like most problems, finding health insurance started with a Google search. What you will get is a bunch of websites that are more than happy to collect your contact information in exchange for a list of “the best insurance options” for you. Unfortunately this isn’t as straightforward as finding the perfect hotel room using Trivago. I’ve gone this route at least twice in my life, and be prepared to have your phone ringing off the hook with insurance agents for at least a month. Don’t say I didn’t warn you. To avoid this simply put in a fake phone number and shop around without being bothered, then call the site or insurance company directly when you find a plan you like. If you already know which network you want to purchase a plan with, you can also just go to their site directly and contact an agent to find out about plans and pricing.

I used which initially listed only short term options, but we’ll get to that later. The options in the image below came from and are based on the age, income, and location information I provided.

Eventually I chose to respond to one of the agents that contacted me, and we scheduled a phone call to discuss the plans he recommended. The types of insurance agents that contact you can vary, but the one I spoke with was from US Health Advisors, which is a United Health Care company. For me this was the most efficient method since I hadn’t shopped around for insurance in a while, and felt comfortable speaking with an agent to walk me through plan options. Feel free to talk to as many agents as you want to weigh all of your options. The type of plan you choose should be specific to your health needs and budget. I’ll review the options I came across below.

Short Term

As I mentioned above, my initial search on returned mostly short term insurance options. They’re tempting since the premiums are inexpensive, but there are many drawbacks to these types of plans, and some can just be an outright scam.

I researched short term insurance to find out that these plans can be an acceptable option for healthy people in between jobs, especially with all the uncertainty right now. Coverage has been extended to a year instead of the past restriction of three months. Short term plans were extended under the Trump administration to give people more health insurance options, but they are not ACA compliant. That's not such a big deal since you aren't required to carry ACA complaint health insurance anymore, but it does mean these policies aren't regulated or underwritten, so you'll have to take your chances.

The drawbacks to short term health insurance plans are outlined in an article from consumer reports, and include "not covering preexisting conditions—defined as anything for which you had symptoms or sought treatment for up to five years before enrolling—it also typically doesn’t cover maternity care, mental health issues, or prescription drugs." It's worth mentioning that some states don't even allow the sale of these types of plans, and in the worst case, they can drop you at anytime if you become ill.

Bottom line for me: I'd rather pay a higher monthly premium for a plan that covers me if something serious does happen, even though I'm healthy. If you're interested in a short-term plan there are articles to guide you in choosing a safe option. Do your research about what isn't covered before signing up - including COVID.

Longterm Buildable Plans - non ACA

This is the type of plan I ended up choosing, but may not be for everyone. This insurance plan falls somewhere in the middle of slightly risky, non ACA compliant with some standard items not being covered, and a typical HMO/PPO insurance plan from the marketplace.

Perks of this plan:

  • Lower premium because it is based on my health information, and not part of a marketplace plan

  • I can choose a basic health plan to cover sickness and preventative care - or choose to add on more "riders" for serious illness, death, or maternity coverage

  • The one I chose is a national plan with United and it's entire network of doctors and specialists

  • My unused funds or doctors visits roll over to the next year

  • Includes Telemedicine option

  • It is underwritten by Freedom Life Insurance Company of America


  • Since it isn't an ACA plan, you must apply, and can be denied

  • Basic plans don't cover maternity costs or mental health, specific plans will vary

  • Higher premium than short-term insurance

Ultimately I chose this plan because I had previously been on a Blue Cross Obamacare plan in a small business of four people and my monthly premium was over $400. My current plan covers anything I will need to use, with a $3,000 deductible for a little over $300 a month with access to a national health network.

Marketplace Health Insurance Plans