Meet the OG of the Group Medical Captive



  • Medical captive insurance company founder Mike Schroeder worked in various insurance industry leadership roles before developing medical captive insurance.
  • Schroeder began applying property and casualty (P&C) group captive methods to health insurance to create a new way for smaller businesses to obtain affordable, quality healthcare coverage.
  • Roundstone, Schroeder’s group medical captive insurance company, focuses on transparency, freedom of choice, and cost savings  to provide small and mid-size businesses with affordable, quality health insurance for all.



If you’ve heard of group medical captive insurance for employer-sponsored healthcare plans and you haven’t heard the names Roundstone or Mike Schroeder, it’s time we brought you up to speed.


Did you know that Roundstone created the first self-funded group medical captive? In doing so, the Cleveland-based company disrupted the health insurance industry to advocate for its employer clients and set the mega carriers back on their heels with our innovative funding strategy. So how did it all begin?


Medical captive insurance company founder Mike Schroeder started Roundstone after working in various leadership roles in the property and casualty insurance arena. Inspired by his 15 years of insurance industry expertise, Schroeder began applying group captive methods to health insurance to create affordable plans for small to midsize businesses.


Schroeder knew that most large organizations self-funded their employer-sponsored health plans because it’s more flexible and cost-effective, and it provides greater control and visibility into cost-drivers compared to traditional insurance.


For small and midsize companies, however, self-funded insurance wasn’t as practical. That’s where the group medical captive comes in. By pooling many employers in a captive, employers can achieve the efficiency and scale of larger organizations and enjoy the benefits of self-funded health insurance.


​Roundstone has successfully led the charge in group medical captive health insurance for over 17 years. Schroeder is the originator (OG) of the original medical captive (OC), providing its clients with business health insurance plans that save them money.




From P&C to OC: The Journey of OG Mike Schroeder


Roundstone CEO Mike Schroeder’s path to group captive medical insurance began in law school and ended with a radical approach to health insurance. His goal was to make it possible for small to midsize businesses to afford quality coverage for their employees.


Schroeder could not have anticipated the impact he would have on the insurance world. But it was a long time in the making.



Mike Schroeder began his career in insurance with a background in business and law. He earned his Bachelor of Science degree in business management from Tulane University, followed by a Juris Doctorate from Ohio State University College of Law.


Gaining Experience

Over his early career, Schroeder gained experience in various roles within the insurance industry. He practiced law as an associate at a Cleveland-area law firm. He founded a medical malpractice underwriter, which was subsequently acquired by a specialty insurance company.


Schroeder also took on senior executive positions with a workers’ compensation insurer and a non-standard auto insurer. Equipped with his legal and business background, he eventually became the vice president and general counsel for a top-rated insurance company.


This large national insurance company began offering group captive insurance to its customers, an insurance model historically seen in the P&C industry. These captive participants obtained liability coverage that protected them from catastrophic losses while also allowing them to reap the financial benefits of paying claims when and only if they occurred (instead of paying a high fixed monthly premium).


Rather than obtaining costly insurance from a traditional insurer, the group captive model enabled companies to join together and pool their premium funds to protect against high claims — the same way Roundstone forms group captives for health insurance today.


Becoming the OG of Medical Captive Insurance

After 15 years in the insurance industry with experience in captive and self funded insurance, Mike decided it was time to make a move on a revolutionary idea that he’d been considering for some time. Schroeder wondered why nobody was using self-funding insurance concepts like group captives to address growing health insurance costs for small to midsize businesses.


In 2005, Schroeder believed he could offer a better alternative to traditional health insurance and started the Roundstone group medical captive. Roundstone was the first company that offered medical insurance through a group captive to companies with between 25 and 1000 employees.


Since then, Roundstone has grown in size and reputation, now covering 500+ employers and 100,000 lives. Now with more than 100+ employees of its own, Roundstone self-funds its own healthcare benefits. Schroeder knows exactly what employers like Roundstone need when it comes to employee benefits health plans that offer accessible, high-quality care at an affordable cost.


Mike Schroeder


Q&A with Roundstone Founder Mike Schroeder


Q: Mike, what about your background in both the legal and insurance worlds prepared you to take on the mega carriers once Roundstone was founded?

A: After working my way up through the insurance industry, it was clear to me that P&C practices could be applied elsewhere. Spending time in the medical insurance field convinced me that the system was inherently broken and that smaller employers were getting a raw deal. There just wasn’t a way to justify the rate increases year after year, and there was no data readily available to employers trying to make good choices about their employee health plans.


Q: It sounds like learning about P&C captives opened up a world of possibilities for you.

A: It seemed too simple. I kept wondering, “Why has no one done this yet?” So, I decided to do it. Captives operate as such a logical failsafe as an insurance tool, especially when there are concerns about going over budget. I learned everything I could about the math behind captives, and it seemed that every way I ran the numbers, the employer won. How do you not move forward with an idea like that?


Q: How did you develop Roundstone’s mission statement?

A: Quality, affordable healthcare should be accessible to everyone. Our clients see their employees as assets and want the best for them while also needing to balance their business’s books and plan for growth. It can seem like an impossible ask for a health insurance plan that is worth the cost and provides quality care employees will use. It shouldn’t be impossible, and it’s not impossible. We can help make that happen.


Q: After starting Roundstone, what changes in the industry were you hoping to see?

A: I think it’s really important that insurance is transparent and gives control of the plan to the employer paying for the plan. That control is no good without data, and there is so much healthcare data. Other insurers have so much data on employers and their employees, and instead of using that data intelligently to help reduce costs, they turn around and use that data to inflate market prices. 

I wanted to put employers in the driver’s seat with their data and teach them how to find those actionable insights that turn into savings. Because reinsurance, a captive pool, and a self-funded claims account aren’t too complicated or out of reach. Those tools are really a whole solution for those smaller employers.


Q: What are you most proud of as Roundstone’s founder?

A: We currently have over 120 employees, which is just incredible. At the beginning of the pandemic, we had 60. The sheer amount of growth we’ve seen over the past couple years really makes me proud that I’ve been able to return to my hometown and bring over a hundred well-paying jobs to the city of Cleveland. 

We do everything possible with bonuses, educational credits, 401(k) matching programs, healthcare benefits, child care, and well-being programs, and more to ensure that our compensation package stands out in the marketplace and adds substantially to employees’ total compensation. I’m very proud of that.




A Revolutionary Approach to Health Insurance: The Founding Principles of Roundstone


Mike Schroeder founded Roundstone, the first medical captive insurance company, on three basic principles that guide every decision that Roundstone makes.


Roundstone’s mission and guiding values focus on providing quality, affordable healthcare for all. They do this by offering freedom of choice when it comes to plan coverage and focusing on data transparency for better insights on cost savings. They also give distributions at the end of each year for unspent premiums and personalize insurance plans as part of a customized plan design process.


More about Roundstone’s mission and guiding principles:


Quality Health Healthcare for All

It’s no secret that healthcare costs have been rising for years. Roundstone works hard to ensure that high-quality healthcare is affordable and accessible for every employer client and their employees. Roundstone clients are innovators themselves, who value their employees as assets to their core business performance and growth.


Considering that family premiums reached an all-time high of $22,221 in 2021, Roundstone’s mission is more important than ever.


Freedom of Choice

With Roundstone, you have the freedom to choose your plan coverage options. Instead of a fully insured plan, you can select your own third-party administrator (TPA), pharmacy benefits manager, and cost-effective vendors. You can also choose your own healthcare providers and facilities with group captive insurance. This allows you to reduce costs without giving up quality of care for your employees.


Focus on Transparency

Access to transparent claims data is another cornerstone of the Roundstone group captive model. Members have access to the Cost Savings Investigator (CSI) Dashboard, which provides continual, transparent claims data, benchmarks, and insights.


You are able to see where you are under- or over-spending according to industry benchmarks and implement cost-containment strategies where needed.


Cash Savings

By self-funding your claims, you only pay for what you use, which allows you to keep unspent funds. Additionally, the Roundstone group captive pool typically has left-over premiums at the end of the coverage period, which are returned to the employers on a pro rata basis. Last year Roundstone returned $20+ million in unspent premium to its group captive members.


Roundstone doesn’t keep your savings, unlike a traditional insurance company. Instead, they give any leftover funds back to you. Two-thirds of Roundstone’s customers save enough money over the first four years to pay for their fifth year’s claims, and 100% of them save money.


Find Freedom With Roundstone


When Mike Schroeder started the Roundstone medical captive in 2005, his vision was to provide every company with affordable, quality employee health insurance.


So far, Roundstone is succeeding in that mission by finding cost-containment solutions for group captive members and returning the savings to fight the rising costs of healthcare. On average, Roundstone saves companies 20% on health insurance costs when compared to fully insured costs.


Ready to see the results in action? Roundstone just finalized a $5.9 MILLION return of savings to employer clients from the past year. Read more about the latest pro rata distribution.




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