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Bluntly, yes, and he would also say this is fixable starting today. Being self-employed does not mean being uninsured. It means the responsibility for finding coverage falls entirely on you instead of a payroll department, and that is a responsibility too many freelancers, contractors, and small business owners quietly ignore until a hospital bill arrives and resets their entire financial life. A $14,000 ER visit is not bad luck. It is what happens when you self-insure without the balance sheet to back it up.
Why Ramsey Takes Health Insurance Seriously
Dave Ramsey is not someone who loves paying for insurance. He has spent decades teaching people to self-insure over time as wealth grows. But health insurance is one area where he draws a hard line. The potential downside of being uninsured, a serious illness, a surgery, a multi-day hospital stay, is so financially catastrophic that no emergency fund provides adequate protection. The average cost of a three-day hospital stay runs around $30,000, and a major diagnosis like cancer or a cardiac event can generate hundreds of thousands in bills.
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The Baby Steps framework assumes you have basic insurance in place before you start building wealth. That includes health coverage. Without it, every dollar you save and every debt you pay off is exposed to a single bad medical event that can wipe it all out.
The Self-Employed Coverage Problem
The challenge for self-employed people is real. When you leave a W-2 job, you lose access to group rates, and individual plans purchased on your own can feel eye-wateringly expensive. But expensive compared to what? Compared to a $14,000 ER visit, a $400-a-month premium looks like a bargain. Compared to a $200,000 cancer treatment, it looks like one of the best financial decisions you ever made.
The Health Insurance Marketplace at healthcare.gov is the starting point for most self-employed individuals. Depending on your net income, you may qualify for premium tax credits that significantly reduce your monthly cost. The IRS outlines the self-employed health insurance deduction at Publication 535, which allows you to deduct 100% of your premiums from your gross income, making the after-tax cost considerably lower than the sticker price suggests.
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The HSA Combination Strategy
If you are reasonably healthy and want to keep premiums lower, Ramsey is a strong advocate for pairing a high-deductible health plan with a Health Savings Account. The HSA is one of the only triple-tax-advantaged accounts available: contributions go in pre-tax, growth is tax-free, and withdrawals for qualified medical expenses are tax-free. For 2025, the IRS allows individuals to contribute up to $4,300 to an HSA, and families up to $8,550.
The strategy works like this: you carry a lower-premium plan with a higher deductible, fund your HSA aggressively to cover the deductible and routine costs, and let whatever you do not spend in a given year roll over and compound. Over time, that HSA becomes a powerful healthcare reserve that also functions as a secondary retirement account after age 65.
What to Look For in a Plan
Not all health plans are created equal, and the cheapest premium is rarely the right answer. You want to look at the full picture: premium, deductible, out-of-pocket maximum, network coverage, and prescription drug tiers. A plan with a $200 monthly premium and a $12,000 out-of-pocket maximum is not necessarily better than one at $350 a month with a $5,000 cap, depending on how much care you actually use.
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For self-employed people, finding the right plan means comparing options across carriers, metal tiers, and deductible structures in one place. Pivot Health makes it straightforward to shop and compare individual and family health plans without having to navigate multiple carrier websites, so you can see what is actually available in your area and make a real comparison before you enroll.
The $14,000 bill is already done. The next step is making sure it is also the last time an unplanned medical event derails a financial plan you worked hard to build.
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Building Wealth Across More Than Just the Market
Building a resilient portfolio means thinking beyond a single asset or market trend. Economic cycles shift, sectors rise and fall, and no one investment performs well in every environment. That's why many investors look to diversify with platforms that provide access to real estate, fixed-income opportunities, precious metals, and even self-directed retirement accounts. By spreading exposure across multiple asset classes, it becomes easier to manage risk, capture steady returns, and create long-term wealth that isn't tied to the fortunes of just one company or industry.
Arrived
Backed by Jeff Bezos, Arrived Homes makes real estate investing accessible with a low barrier to entry. Investors can buy fractional shares of single-family rentals and vacation homes starting with as little as $100. This allows everyday investors to diversify into real estate, collect rental income, and build long-term wealth without needing to manage properties directly.
BluSky AI
The rapid adoption of artificial intelligence is creating significant demand for data centers, power, and compute infrastructure. BluSky AI is building modular AI data centers designed to support next-generation AI workloads while aiming to reduce deployment timelines compared to traditional facilities. For investors looking beyond AI software and applications, the company offers exposure to the infrastructure layer that makes artificial intelligence possible.
ARK7
Residential real estate has historically provided investors with income potential and long-term appreciation, but direct ownership can be expensive and time-consuming. ARK7 enables investors to buy fractional shares of rental properties, offering access to potential rental income and real estate exposure without property management responsibilities. By lowering the barrier to entry, the platform gives investors another way to diversify beyond traditional stocks and bonds.
Immersed
Immersed is building technology for the future of work through spatial computing. Known for its AR/VR productivity platform that enables users to work across multiple virtual screens, the company has grown to more than 1.5 million users worldwide. Immersed is also developing Visor, a lightweight headset designed specifically for professional productivity, positioning the company at the intersection of remote work, extended reality (XR), and next-generation computing.
Miso Robotics
Robotics and automation are becoming increasingly important tools for businesses facing labor shortages and rising operating costs. Miso Robotics develops AI-powered kitchen technology that is already being deployed in restaurant environments, with products designed to help operators improve efficiency and streamline operations. As artificial intelligence expands beyond software and into real-world applications, the company is positioning itself at the intersection of robotics, automation and the future of food service.
Vinovest
Fine wine and rare whiskey have historically moved independently of the stock market, making them a compelling alternative asset. Vinovest manages authenticated, insured portfolios of investment-grade wine and whiskey starting at $5,000 — sourcing, storage, and insurance all handled for you.
FarmTogether
Farmland has historically held its value through market volatility and delivered returns uncorrelated to stocks and bonds. For accredited investors, FarmTogether offers direct access to high-quality U.S. farmland starting at $15,000 — fully managed, with no landlord headaches.
EquityMultiple
For accredited investors looking beyond stocks and bonds, EquityMultiple provides access to vetted commercial real estate deals starting at $5,000, with only ~5% of opportunities passing their due diligence process.
Fundrise
Private real estate and private credit can add income and stability to a stock-heavy portfolio. Fundrise offers access to diversified private real estate and credit strategies through an easy-to-use platform, with professionally managed portfolios designed to generate passive income and long-term growth.
American Hartford Gold
American Hartford Gold is a precious metals dealer that helps clients buy physical gold and silver coins and bars, either for direct delivery or within self-directed precious metals IRAs. The company's services include gold and silver IRAs, IRA rollovers, and home delivery of bullion, giving investors a way to use tangible metals to diversify portfolios and seek protection against inflation and market volatility.
Mode Mobile
Mode Mobile is changing the way people interact with their phones by letting users earn money from the same apps and activities they already use every day. Instead of platforms keeping all the advertising revenue, Mode Mobile shares a portion back with users who engage with content, play games, and scroll on their devices. Named one of Deloitte's fastest-growing software companies in North America, the company has built a large beta user base and is scaling a model that turns everyday smartphone usage into a potential income stream.
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This article I'm Self-Employed With No Health Insurance and One ER Visit Just Cost Me $14,000. Would Dave Ramsey Say I Have No One to Blame But Myself? originally appeared on Benzinga.com
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