Mother/Daughter Team: On Working Together & Making Medicare Easy

Mother/Daughter Team: On Working Together & Making Medicare Easy

Melinda Caughill and Diane J. Omdahl, RN, MS, are co-founders of 65 Incorporated, a company dedicated to making Medicare easy. They recently sat down with me via phone to talk about their company's mission and what it is like to be in an entrepreneurial venture working with family. The perspective of working in a family business that isn't a traditional "Mom and Pop" shop, but rather an internet-based information based service company is an interesting one.

First a bit of background on these women and the company...

Previously, Diane (mother) and her husband owned a company that serviced home health agencies for over 23 years. Having navigated the changes in Medicare in 1998-1999 that eliminated over 30% of their customer base overnight, she was well aware of how complex and changeable the Medicare space is. Frustrated by the lack of unbiased education for consumers (much of the education out there is provided or sponsored by insurers), Diane and her daughter Melinda started 65 Incorporated, officially launching it in October 2012 following a non-compete period from previous company relationships. Melinda's unbridled enthusiasm for capitalizing on the huge opportunity was very evident in our conversation. After all, she shared that 10,000 Baby Boomers a day will turn 65 through 2030. That's a lot of consumers trying to navigate the complex, confusing maze of Medicare.

As a completely unbiased entity, not a supplemental guide from an insurer or Medicare management company, 65 Incorporated differentiates itself from other Medicare help with what it calls the “4 Cs of Medicare.” The company’s content is:

  • Clear — All the Medicare information is provided in an easy-to-understand format (plain English - Yay!).
  • Correct ­— Expert-based information on the website is up-to-date, and accurate (vetted by industry experts such as Diane).
  • Complete — 65 Incorporated takes customers from start to finish through the Medicare process (helps consumers avoid paying too much or ending up with potentially catastrophic gaps in coverage).
  • Credible — Unlike other sources of Medicare that try to sell you specific types of insurance plans, 65 Incorporated’s success depends solely upon the quality of the content (their content is their core business, not just a marketing strategy).

You can learn more about the company itself on their website.

Now, let's dive into the juicer part of the conversation which revolved around what it's like to work with family and how that affects work-life balance.

Diane Omdahl and Melinda Caughill, 65 Incorporated

Diane Omdahl and Melinda Caughill, co-founders of 65 Incorporated

I asked Diane and Melinda what is the most rewarding part of working with family?

Diane shared that working with family is the most rewarding kind of work. Partners have a common interest and there aren't any politics. You know the motives of the family and can trust that ideas that get shared will be worked on with a common goal and not "stolen". Honesty and criticism is more easily shared.

Melinda had a different perspective, one of someone "getting closer to 40 than further away" as she puts it. Unlike working for a regular company where you might be lucky to see family only sporadically, working with her mother and father means she gets to see her loved ones every day. She also shared that "As a mother of a young son, when I get a call from his school or need to take care of him, grandma (aka Diane, my boss) has a vested interest in my personal life." She said this common interest makes work/life balance a possibility all the time. In addition, Melinda shares that they work well together because "We've already developed long-term coping strategies of dealing with each other."

These women seem to truly love working together in the greater family dynamic that flows seamlessly between the personal and professional. So I asked them, what do you like least about working together?

Melinda said, "It can sometimes be hard to not feel like the 5 year old girl working for Mom." It's important to find your own feet and relate as two adult, professional, and accomplished women. She went on to say, "I don't have to prove myself to her, but I want to prove myself to myself. I don't want others' perception to be that you're taking up space because you're the daughter."

"When things get rough, it can be hard to separate the mother/daughter connection from the employer/employee one," Diane shared. When criticism has to be relayed, it can feel more sensitive but we both have to learn not to take it personally.

After running family based businesses for the last 20+ years, Diane said she learned something very important when she sold the first company and then bought it back. That is, when hiring non family members as employees, it is extremely important to be fully transparent from the initial interview. It takes a unique employee to be successful at working within and dealing with the family dynamic that permeates the company. If they aren't comfortable with it, then it's not a fit. Diane said it is of critical importance to outline the roles, expectations, and code of conduct within the company for family and non-family members alike. Melinda shared that one of her copying strategies to keep the personal and professional distinctions clear is that while at work she refers to her mother and father as Diane and Rich in all conversations. Once personal time and life comes, however, it's back to Mom and Dad.

Learn more about Diane, Melinda, and 65 Incorporated at http://www.65incorporated.com/.


Paula Gregorowicz plucks women business owners off the hamster wheel of overwhelm, struggle, and self-doubt and guides them to a purposeful path of building authentic and successful businesses.

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