The Hidden Ways to Save on Small Business Health Insurance

Taming the Chaos with Kim Kramer

by Penny Dawn

As an entrepreneur, you wear a lot of hats—visionary, leader, problem solver. But let’s be real: when it comes to health insurance, many small business owners avoid it like the plague. Why? Because it seems expensive, complicated, or just plain overwhelming. I get it. But here’s the truth: not having a plan could be costing you more than you think.

I sat down with Kim Kramer, a licensed health insurance agent and owner of Ideal Health Advisors, to break down common myths and actionable steps for entrepreneurs who want to protect themselves, their families, and their employees—without breaking the bank.

Myth - Health Insurance Is Too Expensive

One of the biggest myths I hear from business owners is: “I can’t afford health insurance.” The reality? You can’t afford not to have it.

Many entrepreneurs assume their only options are expensive employer group plans or the marketplace (Obamacare). But as Kim shared, private health insurance plans often provide lower-cost, flexible coverage that fits small businesses and solopreneurs better than traditional group plans.

Action Steps:

  • Talk to an independent health insurance broker (like Kim) to explore private insurance plans.

  • Don’t assume you need a large business to access affordable health coverage—many policies exist for solopreneurs and small teams.

If you don’t know what options are out there, health insurance is too expensive.
— Kim Kramer

When Should You Offer Health Insurance to Employees?

At some point, if you want to attract and retain top talent, you need to think about benefits. The mistake many business owners make? They don’t plan for it.

Too often, I hear: “I wish I could offer health insurance, but I just can’t afford it.” The truth is, if you don’t plan for it, it will never happen.

Action Steps:

  • Set a target date (maybe 6 months or a year from now) to start offering health benefits.

  • Work with both your accountant (that’s me!) and an insurance advisor to structure it in a tax-deductible way.

  • Consider a Health Reimbursement Arrangement (HRA) or cafeteria plan—affordable options that don’t require a full-blown group policy.

You don’t legally have to offer health insurance until you have 50 employees, but that doesn’t mean you shouldn’t start earlier.
— Kim Kramer

How Avoiding Health Insurance Could Hurt Your Business

Imagine this: You have a great employee who gets injured. They don’t have insurance, so they put off medical care. Eventually, their health declines to the point where they can’t work. Suddenly, you’re scrambling to replace them.

The real cost of not offering benefits isn’t just about insurance—it’s about turnover, missed workdays, and stress on your business.

Action Steps:

  • Review your financials to see where you can reallocate spending (are you overspending on meals, subscriptions, or office perks?).

  • Instead of saying, “I can’t afford it,” ask, “How can I plan for this?”

If your employees can’t afford health care, they might not get the treatment they need—and that will affect your business.
— Penny Dawn

Final Thought: Take Control of Your Health Insurance Strategy

You don’t have to be a big corporation to get great health insurance coverage. You just need the right strategy and expert guidance.

Kim and I both believe in proactive financial planning, whether it’s for taxes, cash flow, or health coverage. If you’re ready to explore better insurance options, let’s connect.

👉 Need help budgeting for employee benefits? Download my free 3 Step Guide to Cash Flow Mastery!


👉 Need help finding affordable health coverage? Contact Kim at Ideal Health Advisors.

Join me every Tuesday for Taming the Chaos of Entrepreneurship, a live LinkedIn/Facebook series where I sit down with entrepreneurs and business owners who have faced the same hurdles—and come out stronger on the other side.

Penny Dawn

Coach - Speaker - Bookkeeper - Report Ninja

I'm dedicated to empowering small and medium-sized business owners by helping them manage their finances effectively.

With over 20 years of experience, I specialize in streamlining every part of a businesses financial systems and translating complex financial reports into understandable language, empowering you to make sound decisions and thrive.

I believe in building strong relationships with my clients. I pride myself on clear communication, efficiency, and maintaining the highest level of confidentiality.

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