In the spring of 2016 I left my job as EVP, Executive Creative Director of a large advertising agency. It was owned by a publicly held advertising agency holding company that employed 80,000 people in over 100 countries. One of the great benefits of working for a company that size was the benefits themselves. Because when you have that many people in your organization, you have Bezos-level buying clout.

On My Own.
I love a good adventure. So I left the cushy benefits behind and started my own advertising and idea agency called The Weaponry. I love what we have built. The Weaponry is quick and nimble. Strategic and creative. It is a really fun place to work and offers a great culture of collaboration. We have a lot going for us. But one thing we do not have is benefit-buying clout.
The Hard Part
When I launched The Weaponry I asked a lot of questions of my entrepreneurial network about a broad range of subjects. In return I got a lot of great advice. But when it came to insurance I got absolutely nothing. Unless those crickets I heard were trying to tell me something (chirp chirp… run while you can… chirp chirp).
I could tell by the lack of insights that insurance was the toughest nut for entrepreneurs to crack. Those who did comment said things like, ‘Yeah, that’s hard. I don’t know what to tell you.’ And, ‘It Sucks.’ And, ‘I would love to help you, but I would rather set the world record for most paper cuts received over a 24-hour period than talk about health insurance.’

Me vs Goliath
However, I am very proud to say that as of January 1st, 2018, The Weaponry offers insurance benefits. I wanted to share my experience with anyone thinking of starting their own business, or wondering how Obamacare impacts a small business and its ability to grow and compete.
Starting The Search
Over the second half of last year I began planning our employee benefits for 2018. I wanted to offer health and dental insurance. But I also considered a couple of other benefits, including life insurance for full-time employees. But as with so many other aspects of this startup adventure, I decided to simplify to make sure we completed the critical mission.

Research
I began with research. I learned right away that you need at least two non-related employees in your business to be able to offer insurance as an employer. We qualified. I found my way to the health insurance marketplace and started poking around and modeling various products and prices. But in a vacuum it was pretty hard to evaluate what was good, what was necessary, and what was not. From this initial poking I learned my first lesson:
Key Insight: You will not feel empowered to make a good health insurance purchasing decision if you try to do it on your own.
Broker
My business finance advisor encouraged me to talk to an insurance broker, and preferably more than one. He encouraged me to have them model a variety of options so that I could get a feel for the landscape available to me. By talking to more than one broker, he said, you can compare and contrast styles to know that you are getting the right option for you. This was all good advice. But I still didn’t know how to find a reputable broker, let alone multiple brokers.

My Wife To The Rescue
My wife Dawn is a smart woman, and an important part of The Weaponry brain trust. She was the one that finally got us moving in a positive direction on health insurance. How? She talked to our neighbor Sally.
Sally’s husband, Bruce is the President at EBSO, a third party administrator (TPA) benefits solutions company. However, because of our size and our specific needs EBSO couldn’t help us, yet. But Sally said that Bruce frequently partners with Jon Rauser at The Rauser Agency for clients of our size. Dawn got Jon’s contact info. And within a few days Dawn and I were sitting in Jon’s office.
Key Insight: A good wife is the best business asset in the world. This may also be true of good husbands, but I’ve never had one of those.

Dawn and I met with Jon, and it couldn’t have gone much smoother. He started by offering us a range of three or four different insurance providers. Based on our preference, and the providers prevalence in our healthcare market, we quickly narrowed in on one health insurance provider. Then it was a matter of comparing deductibles to get to the final premium options. We simply had to share the ages and family status of our employees. With that we were able to see projected costs, broken down by employee.
Once we provided the names and ages of our employees who would be opting in for our insurance we had to sign a couple of forms to initiate coverage. We also needed forms signed by the full-time employees who were opting out, acknowledging that they had been offered coverage. Next, we had to decide how much of the premium we would pay for our employees. Then we had to send in a check for the first month’s premium.
Then we were done. Seriously.

We Did It!
We had an employer health insurance plan! We have dental insurance too, which was easy to get. We were all grown up! And we were becoming an even more attractive place for smart creative people to work! We had climbed the most daunting mountain on the Entrepreneurial Range. And we planted The Weaponry’s flag at its peak.

Obamacare
Why was the process so easy? Obamacare. I should insert here that I am a staunchly independent voter. I grew up in Vermont where independent thinking flows like maple syrup. I think the two parties are antiquated and don’t allow for my complex vision of the world. But Obamacare made it really easy for this startup to insure our employees. There are no pre-existing conditions. We didn’t need medical exams. We didn’t need to take a lie detector test. I didn’t have to tell anyone that my Great-Great Uncle Nels choked on a peach pit when he was eight years old. (RIP Little Uncle Nellie…)
Is Obamacare perfect? No. It has driven insurance costs up by 30%. But you know what? My baseline is today. So I simply look at the price today and ask, ‘Can we afford to pay this?’ And the answer is yes.
I can’t change the costs. But what should it really cost? I have no idea. All I know is that we were able to get it fairly easily, and all we had to do was pay for it. Our premiums are not much more expensive than the COBRA prices I had been paying since I started The Weaponry.
Conclusion.
I may hate Obamacare in the future. And I certainly don’t want to ever pay more than I have to. But today I am happy to have easy access to health insurance for my team. I want to make sure they are protected. So as you follow the political fight over Obamacare, know that this independent voter, who owns a small business said it was easy to protect his team because of Obamacare. And the small price to pay is simply a larger price to pay. And today, we’ll take it.
*If you know someone thinking of starting their own business that could benefit from this story, please share it with them. If you would like to learn more from my entrepreneurial journey consider subscribing to this blog. If you have more specific questions about my health insurance experience please contact me directly. I am happy to share what I know.