Shawn Jenkins Blog

Why I Started a New Software Company

This summer a few friends and I started a new software company: 3Together

After retiring early and spending the first two years on deep rest, I came into this year with no plan to start another company. At the end of the reset period I was enjoying the simple life made up of simple days with my family. 

When the pandemic hit I didn’t change my schedule since I wasn’t going to an office anyway. However, there was something about the intensity of the moment that got me focused on ways I could help. 

I reached out to a few friends around town in the software community and offered to help any young tech companies who might be impacted by the economic shifts. Pretty quickly I had the opportunity to do video meetings with about twenty different companies in the startup and early stages. Those conversations stoked a bit of a fire in me to be on a software team again.

At the same time I also started The Shawn Jenkins Podcast. I always love hearing stories about software companies and how they grow. So I figured I’d have some conversations with software founders and leaders and share those in hopes that the content would also help young companies navigate the unique times we are all going through.

Hearing the stories on my new podcast further added to the growing desire in me to be back on a team, creating great products, and building something meaningful in a company. 

Here are some of the reasons why I started a new company…

Being a Part of a Team

I love being part of a software team. Working with talented people to design elegant products and engineer them to be scalable so that millions of people can use them is thrilling to me. 

When I have a morning in which I get to spend a few hours with a team of people and we work on a new user interface or some deep technical challenge, my mind gets a tremendous workout and it improves my wellbeing. I enjoy doing hard things and solving really gnarly problems with software. 

What I don’t love is having a calendar full of meetings as far as the eye can see. I crave freedom in my schedule. So as I thought about if and how I might be back on a team, I also thought a lot about how I could best participate, yet not be fixed to a rigid schedule.

Fortunately, my friend and former colleague, Jessica Brewer, was also interested in forming a new team. Jessica is an engineer by training and one of the best leaders I have ever worked with. She led our engineering teams at Benefitfocus and we worked together for twelve years. I always knew she would be a fantastic CEO some day. Jessica is the CEO of our new venture, which both allows me to work with someone I know and respect while also freeing me from the ongoing day-to-day demands a CEO must manage.

Also very fortunately, my friend and the second hire at Benefitfocus, Greg Monn, was interested in forming a new team and leading the engineering efforts as Chief Technology Officer. I’ve worked with Greg for almost twenty years, and together we built applications that are now used by over twenty million people. Our families have grown up together, and I have a ton of respect for Greg. Plus, he and Jessica are just a blast to work with.

As I saw the opportunity forming that would allow me to be on a great team, work to create some really special products, and maintain my freedom and flexibility of schedule, I got super excited. Having co-founders who also love being a part of a team made it extremely compelling.

Meaningful Work

One thing I noticed about people who have retired early is that they seem to find a new set of projects that others have called meaningful work. It seems that when you have saved enough money to be financially independent and no longer have to work, you then find what truly brings meaning to your life and you spend time working on that.

In my case, rather than discovering a new area of work, I discovered that my meaningful work is, and has been, creating software and building an organization that allows people to flourish. This was not a big surprise because I’ve always felt that the company I founded and the work I was doing to help it grow was essentially my calling, my meaningful work. I felt that in building the company it would create a lot of jobs, be supportive to our community, and serve many people with useful products.

As I considered this new software venture, I had to re-answer all of that for this particular time in my life. Was my previous software work an early phase of my life and was it completed? Was there another type of work in a different field that was ideal for the next phase of my life? Since I was able to retire early, should I even “work” at all in any formal sense? 

As I worked through those and many other questions, I came solidly back to the fact that I’m still very young by traditional career standards. After resting for two full years, I felt even closer to my desire to build software and a software company. And I knew that it would be good for my physical and mental health to have a productive outlet for my creative energy. 

While I’m able to be creative in our many community projects and with some of our real estate investments, my most creative energy seems to vibrate best when working with a group of talented folks to design and engineer software applications. 

I have seen firsthand how you can turn your career success into meaningful contributions to your community. So the link between “work” and community support is established in my mind. Said another way, when your plan is to use whatever success you have to support not just your family but also those in need around you, building a company and community service are two sides of the same coin. 

My role with the 3Together is investor and chairperson, and my work focuses on product design and strategy as well as company culture.

Beneficial to Our Community

As I think about investing financial resources and investing time, I have a filter that includes a general requirement that the investment has the potential to result in economic gain that can be reinvested into our community in the future.

Because I’m so involved with the new children’s hospital here in Charleston, this is my primary area of thinking when it comes to future community impact. So when I was considering this new software company, I doodled a series of scenarios I thought could come of the work and then how that potential financial increase could be used to support the work of the children’s hospital. 

Now that the hospital has been completed, I think about things such as medical research, children’s programs to support the kids in the hospital, and ways to support the nurses, doctors and staff. For the new software company, I created a long-term objective for myself that would result in a new medical research foundation. My hope is to create a foundation that will fund ongoing annual research that might lead to big medical breakthroughs and also incremental improvements to ongoing care.

There you have it. I joined my friends so that 1) I can be on a software team again, 2) I have a meaningful outlet for my creative energy, and 3) we can create significant economic value that can be used to fund ongoing medical research for kids. 

And of course all of that had to be accomplished while allowing my schedule to be essentially wide open and flexible. As I continue to both explore the world with my family and help build products people love to use, I’ll be sharing more of my journey here, with you.

3Together, we are just getting started!

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