Healthcare Plans for Freelancers & Entrepreneurs

Phase 1: Freelancer & Small Biz Owner Healthcare Census Schedule a Tour

We’re currently at ~25% of our goal!
Freelancers & Entrepreneurs, you can help by completing this census and sharing this page with fellow freelancers & entrepreneurs.

Without a doubt, the #1 barrier to entrepreneurship in the United States is affordable, quality healthcare options.

Even with the advent of the ACA and healthcare.gov that make healthcare available to more people, the prices are sky-high across the board. And worse, what you get for your hard-earned money tends to be pretty limited coverage with high deductibles. If you have a family, premiums can easily cost more than a mortgage even with high deductible plans.

Freelancers and entrepreneurs are stuck with plans we can barely afford, for coverage that sucks. Which sucks.

As a result, countless people are stuck working for companies instead of starting job-creating businesses.

This reality not only stifles the economy and innovation, it limits entrepreneurship to the privileged who can afford health insurance or the risks of going without it.

For over a decade, I’ve been trying to answer the question “how can we form a group to get better healthcare for people in our community?” Indy Hall alone includes a pool that is as large or larger than many employers.

But the rules say no. Pooled buying power for health insurance in the US is structured around the employment relationship. Alternatives like association plans have not been available since the ’90s.

I’ve explored a lot of options. Done a lot of research. Talked to a lot of experts. I’ve learned a lot of things along the way. Every option I’ve explored has turned out to be a dead end. Until now.

For the last 2 months I’ve been vetting a new model with a new partner, and for the first time I feel like I have found a viable option.

If this option works, independent and small business owners in our group will be able to access the kinds of healthcare plans through a major health insurance provider that are typically only available for very large companies.

This can look like lower deductibles, better quality care/access, and overall savings on monthly premiums.

Best of all, this is not an Indy Hall exclusive. We’re taking the lead to organize the data collection, but the goal is to make this as inclusive and accessible as possible by partnering with business communities across Philadelphia and the United States.

Note: this is NOT the same model that you may have seen through a few outsourced HR companies (aka PEOs) who are aggressively recruiting through coworking spaces and organizations nationwide.

It’s true that some of these HR companies can help you get set up with a plan that saves you money, but that savings you see in their marketing material is only possible if you are providing healthcare for multiple W-2 employees.

If you’re a solo biz owner, like most people in coworking spaces, these PEOs can’t help you get better rates or coverage (and watch out for those year two costs, ouch).


Frustratingly, I’m under an NDA for a lot of the details. Transparency is my default so I don’t enjoy not being able to say more about exactly how this works just yet.

What I can say is that this option does exist in the market, is legal and compliant, and as far as I can tell is actually working for the organizations using it.

The biggest ‘catch’ is that this solution doesn’t work at Indy Hall scale. Realistically we’d need 500-1000+ people enrolled at a minimum to start, and a way to continue growing past that.

The good news is that if this works I don’t want this to be something that only Indy Hall members can access. This is should be something that every self-employed person (and their family) can benefit from.

The other big catch is some expensive upfront costs to setting this up. I already have some ideas for how this could be accomplished in an inclusive, accessible way.

More on that soon.

If this is going to work at all, the very first step before a penny is spent or a contract is signed is collecting data about the potential pool.

The first and next step is to conduct a census of our community of freelancers and solo/small business owners.

This census will help ensure that there is enough interest and reach (which I feel confident about), and that the insurance company has the necessary data used to build initial models for the plans that we’d be able to offer.

So today, I’m excited to kick off a census that collects the information they need to build those models, and we need to be sure that the upfront investments would make sense.

In this survey, we collect as little information as possible based on provider requirements. You’ll be asked for:

  1. Your first & last name
  2. Your gender
  3. Your birthdate
  4. Your residential zip code
  5. Optionally, the same details for a spouse + up to 3 children you wish to cover
  6. Also optionally, the price range of your monthly health insurance costs (total) and your satisfaction with your plan.

Note: the information collected will never be sold, and will only be used for purposes of calculating healthcare rate plans and aggregate statistics.

100% of your personal contact info (most specifically, your email address) will never be shared with our census partners without your direct consent.

You may be contacted by Indy Hall and Indy Hall alone for further information, consent, and updates about progress on these new healthcare plans.

That’s it, and that is my personal promise.


Frankly, I’ve never attempted something quite this large and I don’t know how it’s going to go. But until we have a single-payer system in the US, this is the best option I have found and believe is worth pursuing.

My initial goal is 1000 survey responses. More is even better.

We’re currently at ~25% of our goal!

If you are a freelancer or small/solo business owner, help hit our goal of 1000 census participants by filling out the census below and sharing this page with all of the freelancers and small/solo business owners you know.

Frequently Asked Questions

Do I need to be a member of Indy Hall?
Nope! In fact, we need many people freelancers and entrepreneurs to participate beyond the 400+ members of the Indy Hall community.

We’re actively looking for membership organizations who serve freelancers and solo businesses to collaborate with on this program. Reach out if you’re interested and tell us more about your org!

Do I need to be in Philadelphia or Pennsylvania?
Nope! We’re likely going to focus on our home turf first but that’s more because we have the best reach and access to communities here in Philly.

Ultimately, we’d like to roll out this program as a nationwide benefits package available through membership organizations that support solo/small biz owners.

What if I already have insurance?
Great – filling out this census won’t change your current insurance situation now but it will help us find ways to make it better! The census data will help us work with our partner to develop insurance plan options that we hope are better than your current options as a solo business owner.

Can my spouse/children/significant other get coverage, too?
Just like with an employer-bound plan, you can also buy coverage for your entire family.

Domestic partners can also included, as long as they/you meet this criteria:


If you have questions, please contact healthcare@indyhall.org.

Yours truly,

Alex Hillman
Indy Hall Co-founder

Click here if you have trouble filling out the census below.

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