3 Startup Lessons From Married Co-Founders

David and Josie picToday’s blog is written by David Lipkin, who co-founded SchoolHack Solutions, with his wife Josie Jordan. Lipkin is a musician, composer, and a former teacher and mental health clinician who served youth and families. Jordan is a former English teacher who helped design and implement  personalized, competency-based programs.  

In 2014, my wife Josie and I co-founded SchoolHack Solutions and created LiFT, a personalized learning software platform. For us, entrepreneurship was a completely new direction. We were living in a picturesque Vermont town with rewarding careers in our chosen professions. Josie was a high school English teacher and I was a clinician providing mental health services to youth and families. We had been happily married for 10 years and were the proud, tired parents of three young children just out of diapers.

With our lives and sleep schedules finally returning to normal we chose to leap from the frying pan into the fire. Instead of the predictable domestic bliss within our grasp, we opted for the grinding intensity of an ed-tech startup. Why? The answer is simple–we were inspired by a vision of a healthy educational system that honors the uniqueness of every child. This vision was so compelling that we couldn’t stop thinking about it.

Startups, Like Children, Need Constant Care

Typical for startups and marriages, our experience has been marked by both adventure and adversity, sometimes in rapid succession. On the downside, we deal with the stress from unbelievably long hours, a steep learning curve and financial pressure. We call SchoolHack our fourth baby because it is constantly hungry, keeps us up at night, and relies on us entirely for survival. Besides cutting into our sleep and our savings, we’re constantly thinking about the business, even in our dreams. From a productivity standpoint, being a husband and wife team is a real win because we have 24/7 access to each other.

Also on the upside, we get to soar with the joy of creating something completely original, inspired by our values and informed by a lifetime of experience. Every day is different, and there is something wonderfully clarifying when you know you are 100% responsible for the success – or the failure – of the venture.

The last three years have taught us a lot about ourselves, what we’re capable of, and what it takes to make a family business work. Here are three takeaways from our experience as married ed-tech co-founders.

1. Inspiration from Personalization

Our inspiration comes from the young people we’ve worked with in the local community. Personalized learning has made a huge difference in their lives. Seeing their transformation and growth, we naturally want to disseminate the practices that led to their success so more children can benefit. Their true stories sustain and inspire us when the going gets tough.

If you’re contemplating a demanding new direction make sure the work is personally inspiring so you can renew your energy when you lose momentum, which will surely happen. Any new endeavor will face obstacles that can rob you of confidence. The money will be tight, the website will crash, promising hires don’t work out as hoped, seemingly solid deals fall through, and the competition gets tougher every day. Sometimes it even seems that the more innovative and altruistic you try to be, the steeper the path becomes.

In times like that it’s important to remember your original spark of inspiration.

2. Know Your Startup Limits

From the very beginning of our relationship Josie and I liked to take on ambitious projects together. We knew SchoolHack would succeed because as a founding team we’re battle tested. We took students to the Amazon rainforest twice. We built a house in the middle of a frigid Vermont winter. We had three children in two years while attending graduate school and developing new school programs. We’re completely confident we can withstand the pressure of another big project and keep our relationship healthy.

But it takes honesty, self-awareness and good communication to keep our balance amidst the endless discussions, decisions, adjustments, negotiations, and time demands of our intertwined personal and professional lives.

3. Celebrate Wins With Abandon

Is it worth it?

It is when we remember to celebrate each small success and appreciate the opportunity to help thousands of young people. Celebration is an essential discipline that can all too easily be overshadowed by the daily grind. We try to stay joyful and help each other focus on the progress we’ve made rather than how far we have to go. It’s not easy but the lessons are deep and rewarding.


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