Brothers & Business

Previous Article Next Article

For many start ups, founders who are siblings can make things tricky to say the least. When the Diedrich brothers became business partners, there was no family feud, just family fuel.

Frank and Jesse James.

John, Robert, and Ted Kennedy.

Walt and Roy Disney.

Joel and Ethan Coen.

The Avett Brothers.

Sansa and Arya Stark (ok, they were sisters, but still…)

Three out of Four Baldwins.

These are just a few examples of awesome sibling entrepreneurs and powerful sibling teams throughout history. Is it in their genes? Is it something about having a unique shared history and upbringing? Is there something in these sibling connections that created the (almost) perfect partnerships that fueled awesome innovations and collaboration in entertainment, politics, and business? Quite possibly.

For many of us, getting involved professionally with our siblings sounds like something we could only be talked into if there were few other options. As in, zero other options. Perhaps that’s because we know we wouldn’t work well together based on several years of sibling rivalry and family politics, or differing personalities and work styles. Maybe it’s because although we wouldn’t mind seeing each other more often, or doing something that brought us closer, we are worried that working together could put unnecessary strain on a very important family relationship. Whatever the reason may be, most of us choose not to start a business with our siblings and leave it at that.

Even fewer of us would choose to be sibling co-founders of a tech start up in the insurance industry that would eventually require quitting stable well paying jobs, and risking it all to create a shared vision, and build something awesome (but also initially dependent on family, friends, and angel investors) together and help it grow. Would it help if I added that you don’t know much about tech or insurance when you begin this journey? Let’s add that to the mix as well.

Nevertheless, that is exactly who our co-founders are, and that is exactly what they did.

Chris Diedrich (COO) and Ross Diedrich (CEO) grew up in Rapid City, South Dakota and both eventually landed in Denver , where they decided to take on the rewards and challenges of building Covered, Inc. together. To read more on the business side of how Covered was born, I would encourage you to read this article in Wired, that was published about a year into our journey, or this follow up blog post written by Ross.

However, in honor of #NationalSiblingsDay we reached out to none other than Connie Diedrich, Chris and Ross’ mother, to get the soft side-scoop on how these brothers became business partners…

“Chris and Ross were industrious and entrepreneurial individually and as partners throughout their lives. When we lived in a historical district on a beautiful boulevard with mighty walnut trees, the boys built and operated Kool-aid stands, raked leaves and mowed lawns to earn some cash. Using construction materials found in the garage and neighborhood, the boys and a best friend established a Kool-aid stand brand based on colorful creativity.

About the time they grew out of the Kool-aid stand age we moved from the historical district to a neighborhood with golf courses that straddle the river flowing through our city. To make some cash, the boys collected golf balls out of the river, cleaned them up, and sold them to golfers on the course and in the neighborhood.

As Boy Scouts, they helped each other with earning badges, such as their mountain biking badge, and their Eagle Scout projects. They learned about more structured project planning, organizing donors and volunteers, and networking with entities and persons with authority or jurisdiction over the projects. They supported each other while inspiring others to commit as helpers or donate funds. They both accomplished their goal of attaining the rank of Eagle Scout.

The boys were constantly tossing around start-up ideas during the college, post-college years. The Covered concept was born during a road trip home from Denver one Thanksgiving. The boys conceived the idea on the road and started white boarding the concept and workflow on paper while in Rapid City. The evolution of the concept to reality continues to be a collaborative, mutually supportive, brother venture whereby their respective skills and knowledge allow them to support and sometimes challenge each other. Brothers!”

Here at Covered, we couldn’t be happier that these two decided to go on this adventure together. Being able to work on a small start-up team where you get to share in the vision, direction, and excitement of the company as a whole, alongside the two people who founded it in the first place is inspiring and motivating in ways that some might struggle to find in their daily professional lives. There is no “that’s not my job”, or “that’s good enough for now”. Our work is filled with hustle, teamwork, support, creativity, and more high fives than you can shake a stick at.

There is an anonymous quote that reads “Brothers share childhood memories and grown up dreams”. Working as a team to help Ross and Chris bring their road trip dream to life has presented us with countless twists, turns and triumphs, and we wouldn’t have it any other way. We’re with you for as many miles as it takes, let’s hear it for the boys!

Sign up for our newsletter