How to start a business and get health insurance

When I first started Dinsmore Steele, I knew two things:

1. I was very good at PEO.

2. People needed my expertise.

I don’t say this to brag—I say it because it’s the key reason I started my business, and it’s true. When you have a skill that people need, you have the foundation of a business.

The more people who need your services, the more opportunities you create to grow revenue. It’s that simple.

But everyone has something they’re great at—yes, everyone.

If your skills solve someone else’s problem, they’ll pay you for that. It’s basic supply and demand. The challenge isn’t having the skill but understanding how to turn that skill into a business.

So, where do you start?

It’s simpler than you might think.

If your idea requires large sums of cash or inventing something entirely new (think launching an energy drink or tech product), you might want to reconsider. Instead, focus on your skill set and who needs it.

For example, if you’re great at building websites, thousands of small businesses need a robust online presence.

It might sound easy, but the business world is built on this principle: identify and fill a need.

Here’s what worked for me

When I launched Dinsmore Steele, I quickly realized the problem wasn’t that people didn’t need PEOs—they did.

But I was offering just one solution.

That’s when I created a brokerage business with every PEO option, simplifying everything from the forms, quoting, and data collection to even onboarding. By diversifying my offerings, I gave businesses more flexibility and catered to a broader range of needs.

I also solved the issues I knew people experienced with each stage of a PEO.

And that’s when the real growth started happening.

Here’s a simple framework that helped me—and can help you, too:

1. What are you great at?

2. Do people need your help?

3. Will those people pay you?

4. Ask them to use your services.

If they say yes, congratulations—you’ve got a business. If they don’t, no problem. Move on to the next idea.

But don’t get stuck thinking you need large sums of cash or flashy ideas to start.

Any business's goal should be to help people and make money. After all, you can’t help anyone if you’re not generating income.

The Big Question: Affordable Health Insurance and Growth

For many self-employed people, one of the biggest hurdles isn’t finding clients—it’s the cost of health insurance.

With the support of a traditional employer, entrepreneurs can avoid high premiums or limited coverage options.

That’s where Association Health Plans come into play. These plans offer affordable health insurance from national carriers, making them an excellent option for when you are just starting. They allow you to tap into group benefits at lower rates, which would otherwise be difficult for an individual or small business owner.

This makes it easier to protect your health, stay covered, and focus on building your business.

But as your business grows and your needs become more complex, you may outgrow these plans. This is where transitioning to a Professional Employer Organization (PEO) makes sense.

Transitioning from Association Health Plans to PEO

Once you start taking on employees or scaling up your operations, managing everything from payroll to compliance to benefits administration can become a significant burden.

That’s where a Professional Employer Organization (PEO) can help streamline these tasks, giving you access to the benefits typically reserved for much larger companies—like comprehensive health insurance, retirement savings plans, and HR support.

With a PEO, you can scale more efficiently while maintaining control over your core business. You can focus on what you’re great at—building websites, consulting, or running a boutique firm—without getting bogged down in the day-to-day administrative tasks that can overwhelm growing companies.

What About Scaling?

Let’s say you’ve followed the framework and built a solid foundation for your business.

Now what?

This is where scaling comes in. As you grow, your responsibilities multiply. Managing payroll, keeping up with tax compliance, and providing competitive benefits packages to employees can quickly become overwhelming. A PEO provides the infrastructure you need to manage these growing pains without drowning in the details.

By partnering with a PEO, you gain access to an HR platform that allows your business to operate as efficiently as possible while giving your employees the benefits and protections they need to thrive. Knowing you have the right support will enable you to keep scaling.

Final Thoughts

Everyone’s entrepreneurial journey is different, but you must do it intelligently if you want to build a business around your skill set. Whether you’re just starting out and looking for affordable health insurance through Association Health Plans or ready to scale up and need the infrastructure a PEO provides, the key is understanding the resources available at each stage of your growth.

Business is about helping people and making money. And if you’re not making money, you can’t keep helping people. So start simple, scale smart, and ensure you have the right support systems to grow your business sustainably.

If you’re stuck or need guidance, then let's chat—I’m happy to help. I've been helping people in every stage of their business find the perfect solution for their team and themselves.

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Rodney Steele is the CEO of Dinsmore Steele , a leading PEO brokerage that helps businesses simplify their HR, payroll, and employee benefits. With years of experience in the PEO space, Rodney is passionate about assisting companies to navigate complex decisions, from PEO renewals to benefit plan negotiations.

Known for his humor, wit, and straightforward advice, Rodney provides valuable insights that make HR outsourcing easy to understand and execute. When he's not closing deals or advising clients, you can find him playing pickleball or enjoying time with his family on Long Island.