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Re:America’s Health-Care Crisis Is a Gold Mine for Crowdfunding by fpgaminer on Thursday June 15, 2017 @07:04PM (#14565209)
As far as I know * , you can write off your personal health insurance premiums as expenses on your taxes when you're filing as a sole proprietor or an SMLLC (and I assume something similar under S and C corps). So ... at least that's a ~30% discount.

* Based on a little research I did; I'll find out for sure next April :P

P.S. Another nice thing about going solo is your 401k. You can set up a Solo 401k, which has a MUCH higher contribution limit. 401k through employer is limited to ~14k, while a solo 401k is up to something like 50k. Plus, you get to pick your 401k provider, and as far as I could tell Solo 401k through Vanguard was _significantly_ better than the criminal fees I was subjected to under my previous company's 401k.

This is all assuming your side business is successful enough to fill that extra 50k bucket :P

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