How to provide health insurance to co-owner?

[Brian Barfoot]

My business partner and I have gotten the ball rolling on our REI business and since I still have a W-2 job with good insurance I feel very happy with the long-term plan. His trouble is that he is a contractor by trade and is stuck in the "too rich to get government insurance, too poor to buy it independently" hole. So here's my questions:

Do any of you provide insurance as an REI company and if so do you buy in/pool with other companies to get a better rate?

What level of scale did you reach before it became a good idea to offer insurance?

Is there some program for small business owners that I might not be aware of that would make it easier for us to get him insurance?

We live in NY which makes things more expensive for nearly everything and I'd imagine the pattern holds for health ins.

[Dacia Ray]

In a previous small nonprofit I ran in NY, we were able to offer health insurance for our three employees via New York State of Health, which is accessible not just to individuals but also small businesses. The company can opt to cover the full cost of insurance or a percentage of the insurance - it sounds like maybe covering a percentage might work in this situation. My recommendation would be to find an insurance navigator to work through the options with you - they are trained by the state and free for you to access, usually work for community organizations. They can help weed through the paperwork and options. There's more info and a directory here: http://info.nystateofhealth.ny.gov/IPANavigatorSiteLocations