Here at MyHealthMath, we love our team. Each month, we select a team member to share with our network, so that you can get to know us from the inside out. This month’s team member is our leader, Bob Watterson.


What inspired you to build MyHealthMath?

I always wanted to be an entrepreneurFrom the time that I was young, I was always attracted to building my own business, it’s just the cloth that I am cut fromI liked to create ideas that were interesting from both a psychological and capitalistic perspective. 

During the late 80s, I was working in an area that was peripheral to the mortgage business and I was hearing about a lot of new ways to structure a mortgage, given that interest rates were so high. At the same time, my peer group was buying homes and trying to navigate mortgages themselvesAdditionally, personal computers were new. I was fascinated by the idea of using a spreadsheet to better understand mortgages and help people make more cost-effective decisions. I created FirstFacts, my original decision support tool, and was able to build a business around itI sold this business to a bank in 2001. 

A few years later joined another startup involving price transparency using a reverse auction model. Our platform allowed sellers to compete in real-time auctions for consumer financial productsWe worked hard to build this business for 7 years, but it didn’t quite make it. 

So, I had to buy a new health insurance policy – for the first time, on the individual market, without the plans being curated by an HR department and without any employer financial assistanceThe experience reminded me of my earlier work with mortgage selectionso I was intellectually interested in this choice from the startA broker guided me to a plan choice, but I wasn’t satisfied with the granularity of his approachI had a couple of months to make the selection and built a rudimentary version of the decision support calculations that go into MyHealthMath nowsaved $1,800+ by picking a different plan than the one the broker thought would be best for me

Seeing this result was a real lightbulb moment, and I knew that this could be a good place to build a businessI spent a year learning as much as I could about health insurance and plan choiceI was camped out in our kitchen for months with two monitors and a million numbers on multiple spreadsheets while I figured out the initial concept. 

I was really motivated by an intellectual desire to help solve this problem for more people than just myself. I wasn’t sure that others could save as much as I did, but I had a hunch that there was strong potentialFurthermore, I realized that employers could also use a lot of help in deciding which plans they should offer their employees. Both problems seemed to fit well together, and I believed that I could build a business that would create solutions for them

What’s your day-to-day like at MyHealthMath? How has the company furthered your goals?

Bob Watterson (he/him/his), CEO

Day to day I do general management duties – all departments report up to me and I then take part in or make decisions that move the business forwardam responsible for making sure that we have sufficient financial resources to build the business. Lastly, but not at all least, I am a salesperson and I work to develop large partnerships for our business.

MHM has furthered my ongoing goal of building things. I really enjoy connecting the dots and making things happen. I like to do the discovery work, of talking to people about my ideas and meeting with new people who have ideas that are different from my own. There is a lot of wonder and excitement in building a business, and it also takes a lot of perseverance. 

Describe a rewarding project that you have worked on during your time at MyHealthMath.

Actually, one of the most rewarding thingrecently has been a project that I was not a part of. Caitlin, our VP of Marketing, and others on our team created a new MHM consumer experience called “Decision Doc.” Everyone involved with this project gave it a lot of energy, and it really took off. We are getting all sorts of positive market feedback. To watch our highly effective team create this product – without my direct involvement –  was really rewarding. 

What goals do you have for the future of MyHealthMath?

Simply put, I hope that every employer in the United States sees the value in and uses MHM.  

What is your favorite thing about working with the MyHealthMath Team?

My favorite thing is interacting with kindfun, diverse and passionate people, many of whom are a lot younger than me. I feel really lucky to work with a young and vibrant team that teaches me new ways to look at things with kindness and a smile on their face.  

What are some of your favorite hobbies outside of work?

Exercise related outdoor activities are my favorite, with road cycling being at the top of the listI love boating as well and hope to sail more in the futureMy daughter Sage and I love to pull lobster traps together. I also like to do woodworking and build boat models. I would like to read more