Milwaukee September 2018 Featured Entrepreneur: Melinda Caughill // Featured Member // Sep 12 2018

September 2018

Melinda Caughill of 65 Incorporated and i65

Doyenne Group (DG): What business do you own?

Melinda Caughill (MC): 65 Incorporated and i65

DG: What is your role/title within your business?

MC: Technically – Sales and Marketing, In reality – Anything that needs to get done

DG: What is the goal/mission of your business?

MC: i65 is the first of its kind. Today, seniors turning 65 and becoming eligible for Medicare have very few – if any – places to turn to get unbiased, expert Medicare enrollment guidance specific to their unique needs. But, today, seniors are increasingly turning to professionals they already trust who do not sell insurance — like financial advisors, HR, medical professionals, etc. — in hopes that they can provide some sort of Medicare guidance before they engage in a Medicare sales conversation. With i65, any professional can provide her clients with expert Medicare enrollment guidance — without having to become a Medicare expert. Plus, since i65 is NOT affiliated with the sale of insurance, our tool is perfect for a fiduciary environment.

DG: What is your background? What got you to where you are now?

MC: Entrepreneurship is literally in my DNA. I grew up watching my mother start what would become a multi-million dollar company from the basement of our home.
I started my first company, a small graphic design firm, when I was 23. I successfully rolled that company into a larger advertising agency about five years later, where I became a partner leading the company’s push to specialize in franchising.
However, my DNA could not be denied. When my mother, who is a nationally-recognized Medicare expert, decided to start a new company helping the nation’s seniors to get the information they need to avoid costly Medicare mistakes and make the best decisions for their unique needs — I was all in.

DG: What made you decide to start your business?

MC: As I mentioned, Medicare is in my family.
My Mom’s first company (that she built along with my Dad, a brilliant marketer) helped the nation’s hone health care agencies comply with changing Medicare regulations. In my early years, I worked with her and my Dad to grow the company.
When my Mom decided it was time to transition to helping the consumer, it just seemed natural that I would “go home” to help.
We started our business to simply provide Medicare education to seniors, but it quickly became apparent that there was more than enough extraneous Medicare information out there. People needed help – not more education. So, we started by providing one-on-one Medicare enrollment consultations and eventually i65 Medicare software.

DG: What is your biggest accomplishment in your business to date, and why?

MC: Helping i65 transition from a consumer-facing software product to a business-to-business model is probably the single “most-pivotal pivot” we’ve made. I make it my personal mission to always be talking to the client. This was a crucial insight I learned after piecing together many conversations. This single insight has dramatically changed our company for the better.

DG: If you could give one quote to live by, what would it be?

MN: “When the world laughs at you, laugh right back. After all, it’s as funny as you are.”

DG: What are three things that people may not know about you?


  • I teach drawing & painting to kids in my spare time.
  • I LOVE dogs.
  • I didn’t know if I wanted kids, but being a mom is the best thing I do each day.

DG: What words of advice do you have for aspiring entrepreneurs?

MC: Listen!
Ask questions and listen to the answers. Not everything you hear will be useful. But, if you start hearing common themes emerge through your conversations, pay attention!

DG: What does Madison need to encourage entrepreneurs to stay and grow their businesses?

MC: Milwaukee –
If the community is serious about growing successful companies and ideas, the community needs to embrace entrepreneurs who don’t fit the stereotypical mold. (Minorities, females, older people, etc.)


Join us at our monthly Milwaukee Connect Event on Wednesday, September 12 from 6pm to 8pm for an evening of networking with other women professionals and a presentation from this inspirational entrepreneur.


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