If you’re self-employed — whether you’re a real estate investor, a landlord living off rental income, or running your own business — you already know the headache that comes right after tax season: health insurance.
Most coverage options are built around a W-2 paycheck. Employer plans assume a steady salary and a company HR department handling enrollment. But when your income comes from rents, distributions, or a business you own, that model doesn’t fit. Income that fluctuates month to month makes it hard to estimate subsidies accurately. Self-employed status alone can knock you out of some group options entirely. And if you’re financing property or running a growing business, the last thing you want is a coverage gap or a denied claim at the wrong moment.
It’s a problem I’ve dealt with directly. For years I patched together coverage the way a lot of business owners do — overpaying for a plan that didn’t really fit how my income actually works.
What finally worked for me was working directly with my son, JP SaintAmour, who runs SaintAmourHealth and specializes in health coverage for self-employed people, business owners, and investors. He used his proprietary comparison tool called SmartHealthMatch to shop the market and find a plan that actually made sense for my situation, rather than a generic off-the-shelf option.
If you’re a landlord, investor, or entrepreneur and you’ve been putting off dealing with your own health coverage — or you’re overpaying for a plan that doesn’t fit your income — it’s worth a conversation. You can reach JP and book time directly at SaintAmourHealth.com/book.
Fred SaintAmour is the founder of Boathouse Commercial Funding Group, providing commercial real estate financing for investors and business owners nationwide.