Michael Kosloske

Insurance Industry Executive

Originally from Rockford, Illinois, Michael Kosloske developed an acumen for insurance at an early age, having been born into a family who had been leaders in the industry for years. Before entering into the insurance profession himself, Michael had already devised plans to create a scalable online platform to bring health insurance consumers, agents, and carriers together in order to transact business.

Michael attended Florida State University, earning a degree in Risk Management and Insurance in 1986. In 1987, he joined a third-generation family business called Health Plan Administrators, accepting the role of President. Eleven years later, he purchased 100% of the company. From that point onward, under his leadership, the company began to focus on fully-insured niche individual health insurance sold online, eventually developing and owning more than 20 health insurance blocks insured by many carriers and ranked in the top ten worldwide.

In 2003, Michael Kosloske founded Health Plan Intermediaries, an insurance company that has marketed and administered more than one million short-term medical policies worldwide. Two years later, he sold that company to Independence Holding Co (IHC). At that point, Michael Kosloske became the IHC Divisional President, a job he held from 2005-2007.

In June 2008, he founded Health Plan Intermediaries, LLC, which conducted business under the name Health Insurance Innovations, LLC (HII). That firm merged with Naylor Group Partners in August 2008. Only three years later, Michael purchased the Naylor Group Partner Ownership portion of HII and emerged as the sole share owner. Through entrepreneurial spirit, hard work, and determination, he was able to navigate launching this enterprise under tremendous adversity and stress during the depths of the financial crisis of the late aughts. He would continue working for Health Plan Intermediaries, LLC until his retirement. Since then, Michael has become a member of the company’s board of directors.

Michael Kosloske is also currently on the Board of Directors for St. Joseph’s Hospitals Foundation and Seminole Boosters. In his spare time, he enjoys playing tennis and golf.

Where did the idea for your company come from?

It’s a third generation family business that got started in the late 1930s.

What does your typical day look like and how do you make it productive?

There are two kinds of days. The first kind is when I’m in the office and I work as hard as I can, then get home at a reasonable time. On those days, I have to make sure that one aspect of my life does not intrude on the other so I can spend quality time with my family. The second kind of workday I have involves traveling for work. While I’m gone, I try to get as much done as humanly possible, that way when I get home I can spend time with my loved ones and not have to worry about work.

How do you bring ideas to life?

I write my ideas down. And once I get them cleaned up and presentable, I bounce those ideas off of others to get all the details squared away and the kinks ironed out. And, more importantly, once the plan is executed and the inevitable hiccups arise, my team and I have to know when to either fix the plan or move on from it, since we could very easily waste time on something that really does not work or deserve wasting energy trying to fix.

What’s one trend that excites you?

Having virtually all the industry information online enables customers to be more informed about what they want to do insurance-wise, therefore there’s a much larger capacity for people to look things up and educate themselves than there was in the past. This helps ordinary people to make the best decisions for themselves and makes it easier on us as insurance professionals to provide what they actually need in the first place. That’s an exciting trend.

What is one habit of yours that makes you more productive as an entrepreneur?

Balance. You have to work hard, but then you have to be able to balance that with your family and health. Spending all of your time in the office is not good for your physical or mental health. You need time away from there and quality interaction with your family.

What advice would you give your younger self?

I would tell my younger self to focus a bit more on health and diet. That’s the one thing that can really slip when you’re focused on work. And it’s more diet than anything else, to be honest, so I would just tell the younger version of me to eat better.

Tell us something that’s true that almost nobody agrees with you on.

You appreciate working hard for success and actually earning it far more than if it was simply given to you.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Try to enjoy the here and now. Have fun and enjoy life everyday as much as you can. That way, you can look back at what you did with a sense of pride; with a sense that you did what you could and regret nothing.

What is one strategy that has helped you grow your business?

My strategy is to put together a plan, a plan which can be broken up into large and small pieces. I take care of the smaller pieces first, since they’re usually easier tasks to accomplish, then I take care of the bigger things. Personally, I arrange all of these tasks in a to-do list. And, most importantly, I’m always impatient to finish that list. That way, once I get it done, it’s done, and I can focus on whatever’s next.

What is one failure you had as an entrepreneur, and how did you overcome it?

Failure would be having business deals that didn’t work out for one party or the other. When that happens, as a professional, you try to find the common ground in order to make the best out of a bad situation. We’re an established firm, and because of that a lot of people give us the benefit of the doubt that we conduct our business fairly—as they should. But in return, we have to treat them the way they want to be treated, too. I find that simply treating people with fairness mitigates many failures and solves a lot of problems generally.

What is one business idea that you’re willing to give away to our readers?

Coming soon, there will likely be a big opportunity in the field of human transportation. I mean, there is a real chance that drone travel may be a thing in the near future. Instead of cars or airplanes, the idea is to use drones instead. If implemented, it will allow passengers more time to do the stuff they want to do in transit, and less time navigating highways or trudging through congested airports.

What is the best $100 you recently spent? What and why?

Recently, I spent a bit more than $100 on a plane ticket to see my wife, who was in another city at the time. I love my wife dearly, and I can think of no better way to spend money than to visit her, no matter where she may be.

What is one piece of software or a web service that helps you be productive?

Microsoft Excel has been extremely useful for me. For forecasting numbers and figuring out the best business opportunities, that software has been very helpful. I would recommend more people use it for any number of everyday applications.

What is the one book that you recommend our community should read and why?

While I don’t have a single book of his in particular to recommend, I am an avid reader of Tom Clancy’s novels. He always did his homework on whatever subject he wrote about. It brought a sense of realism to the story and helped elevate the tension in every one of his works.

What is your favorite quote?

“Don’t cry over spilled milk.”

Key Learnings:

  • Don’t worry about the small things. Instead, concentrate on the overall picture.
  • Treat people the way you want to be treated.
  • Always make sure you have a plan.