Getting to Know You: Michael Kosloske, Founder of Health Insurance Innovations, LLC

Hailing from Rockford, Illinois, Michael Kosloske is a retired insurance executive and the Founder of Health Insurance Innovations, LLC. He would continue working for Health Plan Intermediaries, LLC until his retirement and was formerly a member of the company’s board of directors.

Michael attended Florida State University from 1982 to 1986, majoring in Risk Management and Insurance. After graduation, he accepted a position at Dun and Bradstreet Planning Services, becoming the youngest manager at the company. A year later, he would return home and join the family insurance business, Health Plan Administrators, taking on the role of President and becoming the third generation of his family to oversee operations at the company. Under his stewardship, Health Plan Administrators began concentrating on selling fully-insured niche individual health insurance online. Michael would eventually purchase 100% of the company in 1998.

Five years later, Michael Kosloske created a new company called Health Plan Intermediaries, LLC, a firm that would go on to market and administer more than one million short-term medical insurance policies to people across the globe. In 2005, he sold that firm to Independence Holding Co., a company which retained his expert services as Division President. He worked in the public management arm of Independence Holding Co. until 2007.

At that point, Michael Kosloske’s entrepreneurial instincts re-emerged, and he created another company called Health Plan Intermediaries, LLC that conducted business under the name Health Insurance Innovations, LLC. After guiding the company through the financial crisis and ensuing Great Recession of 2007-2009, he brought the firm to the NASDAQ stock exchange in 2013 with a very successful initial public offering. Since then, the company has traded under the symbol HIIQ. From 2017 to 2019, it would outperform every other publicly traded insurance company in asset growth.

Michael Kosloske retired from the insurance industry not long thereafter. He remains active in the Florida  business community through sitting on the board of Directors for St. Joseph’s Hospitals Foundation and Florida State Seminole Boosters.

What do you currently do at your company?

While I’m officially retired, I do still perform some board and consulting work. I think it’s important to be a source of advice and a voice of reason for those that are currently running the company, so it keeps heading in the right direction.

What initially inspired you to get into the industry?

My grandparents started an insurance business in 1939. Growing up immersed in the insurance industry made me want to provide the best possible service to consumers and provide them with better options than they had in the past. At the company, we also try to make all aspects of holding an insurance policy as easy as possible for our customers. The fewer things our customers have to worry about, the better.

What defines your way of doing business?

It’s important to work hard, treat people the way they want to be treated, and hold a positive and optimistic point of view. It’s also important to be humble and willing to listen to all points of view. When it comes to managing such a large enterprise, being open to suggestions from others is a competitive advantage. I’ve found that a well-informed group often makes better decisions than a single individual, even if the individual in question is the CEO. That way, perspectives that otherwise might never have been considered are discussed, and potential blind spots are covered.

How do you measure success?

Ultimately, I measure success by making sure that our customers, our employees, and our stockholders are content. And that is best accomplished by treating people the way you yourself would want to be treated. To put it in rather stark terms, you don’t want to be the only person attending your own funeral. You want to be the kind of person others want to do business with, socialize with, and work for, and you want people to remember you fondly, no matter how far apart you may have become. From my point of view, that is the way to gauge a successful life and career.

What would you consider the most valuable lesson you have learned?

When you get knocked down—and it will happen several times over the course of even the smoothest, most successful business career—you get right back up, and you find a way to remain optimistic. Doing this won’t automatically lead to success, but it’s a much better course of action than constantly ruminating over a failure and feeling sorry for yourself. You can learn from failures and avoid repeating those mistakes next time. Just don’t give up, whatever you do.

What advice would you give others wanting to get into the insurance and risk management business?

It’s a great business that has a lot of great people working in it. It requires hard work, common sense, networking, and perseverance. Success is not guaranteed, but if you treat people the way you yourself would want to be treated, you can achieve great things in this industry.

How did you maintain a work life balance?

You have to plan family activities like you would plan out projects at work. You have to plan for that kind of balance in the first place—it doesn’t happen naturally.  So, you have to make sure that you put the same sort of hard work and effort into your family life that you put into your work.

What is a piece of technology that helps you with your routine?

For my entire career, I’ve tried to leverage technology to make the company really easy to work with for our customers. So, using the iPhone has been a godsend for us, because it is, for all intents and purposes, a little computer that virtually everyone carries around their pocket. Customers can use their iPhones to purchase our products, make claims, or speak to representatives from the company. This way of operating is vastly superior to the old, analogue system.

Who has been a role model to you and why?

I would say my parents, and specifically, my mom. She taught me how to prioritize the needs and happiness of others above my own so that important relationships are maintained and become reciprocal. And she ended up having a great life because of her generous and giving spirit.

What is a piece of advice you’ve never forgotten?

I received a great piece of advice during my freshman year at my orientation at Florida State University: “Don’t cry over spilled milk.” It’s a bit of a cliché, I know, but it’s also a truism. It means that there’s no point dwelling on bad things that have happened to you, so focus on how to make the best of your situation going forward.