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Here are some strategies: Get some employees working 30+ hrs week and use a service like Gusto to sign up for their healthcare. Enroll in a college program and enroll in the University Health coverage (this is a stealth move and typically have great coverage at low cost) Healthcare Exchange has been mentioned. Shared cost models are getting popular but have various limitations. Sign up for catastrophic coverage and cover other expenses on your own (may also want to have a health and exercise program to support that ;) Take an evening job at a retailer that offers healthcare. Might have to be a manager or above level. On the line of the above university approach, several institutions offer faculty healthcare so you could teach and pick up some coverage there. When I used to be a financial counselor for low-income folks, there was a rhythm that most suffered a medial crisis that brought about significant financial strain where coverage would have made it a non-event otherwise. To this end, do not take it lightly and make sure you have strong coverage, especially in this day and age.