Health Insurance while operating?

October 18, 2025

by a searcher from Carnegie Mellon University - Tepper School of Business in Washington, DC, USA

I’m curious to know what people, particularly those with a family are doing for health insurance after acquiring a business; especially those who are self funded and operate smaller businesses or multiple smaller businesses. Happy to connect with a broker in Northern VA (NoVa) or Pittsburgh metro. How can you get a high quality, potentially multiple state coverage? Some thoughts: 1) Marketplace seems very restrictive, which is limiting in a multi state metro like DC; except maybe BCBS if available. 2) Small business insurance plans seem like they might be an option, but I’m not super familiar yet, and then you have potential participation rates to abide by - which I’m assuming is difficult to achieve on the lower SDE side (or impractical). Perhaps there are some creative ways in structuring an LLC to qualify? Thanks for any suggestions and helpful info. Hopefully this will be helpful to others as well.

Reply by a searcher
from Carnegie Mellon University in Chapel Hill, NC, USA

Greetings from a fellow Tartan and prior 15 year resident of NoVA. A similar question was raised recently along this line and I listed several options. Groups like Gusto provide multi-state coverage but you are correct in that you have to have participation rates (or at least offered to FT employees). Arguments can be made for employees to use their state’s healthcare exchange and you can adjust compensation accordingly.

Reply by a professional
from Wesleyan University in Philadelphia, PA, USA

I can give you a quick rundown of your options. Often, if there’s not a health insurance plan in place, and you have less than 50 employees, you may not want the expense/admin associated with implementing a plan. It is always far more expensive than anticipated and is only going up

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