MARK KOHLERMain Street Professionals, Main Street Professionals, Main Street Professionals, Main Street Professionals, Main Street Professionals, LLC · Owner at Main Street Professionals, LLC

Sole Proprietor Health Insurance Strategy That Saves Thousands

11 Feb 2026 · 1 min

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In this video, Mark Kohler explains that many gig‑economy workers who receive a 1099 (e.g., Uber, DoorDash, Turo) are actually operating as sole proprietorships and file a Schedule C. He outlines how these self‑employed individuals can purchase individual health coverage through the federal marketplace (healthcare.gov) or state exchanges, and then deduct 100% of the premiums on their Form 1040. Kohler emphasizes the tax advantage of selecting a high‑deductible health plan, which qualifies the taxpayer for a Health Savings Account (HSA). By contributing to an HSA, the sole proprietor gains triple‑tax benefits—tax‑free contributions, growth, and withdrawals for qualified medical expenses—maximizing overall savings.

Chapters

Can you talk about health insurance for sole proprietorships? So if you're a small business owner, let's say you've got a side hustle. 50 million plus Americans now get a 1099 for Uber DoorDash. Turo, if you have a 1099, you're a small business owner. You just didn't know it. So that's going to go on a schedule. C, as in Charlie, you're a sole proprietorship if you buy your own health insurance and you go out on the exchange. Some states have their own exchange. You can go to healthcare.gov in most states and get your health insurance. Your health insurance is 100% deductible. So so it's going to be on your 1040 tax return. You get to write off your health insurance. Where the HSA comes in is you choose a high deductible plan. Now you have the HSA and you can contribute to the HSA and unlock all those benefits.