Starting a company with a 20 year old “Kid”

A story about a beautiful tech relationship

At the age of 27 years old, my entire world completely changed: my software company Lettuce got acquired by the tech giant Intuit for $30 million. It was a surreal moment and I was beyond thrilled because our team achieved a very rare feat. It was my greatest accomplishment to date.

Fast forward a year and half later, I was looking for a new problem that I could help solve. One of my very first angel investors in Lettuce caught wind of this and asked me to meet with a “young buck” by the name of Spencer Shulem. This investor claimed that Spencer had a lot of potential as an entrepreneur and could potentially do great things. I happily agreed and a few days later, I was on the road driving north of Los Angeles to meet with this so called “kid that is beyond his years.”

Within minutes of meeting Spencer, I knew he was different and a true entrepreneur. He was philosophical, hungry, and even a little angry that he had not impacted the world yet. A frustration I had early on in my life.

As we continued to chat, he shared that he had this idea for a todo list app that targeted small businesses owners who wanted to track their employees more efficiently. In my mind, this confused me because why would a young 20 year old “kid” care about productivity for businesses? I presented Spencer with this question and he quickly let me know that part of his idea was authentic: he struggled with ADHD and todo lists helped him concentrate on the things that needed to get done. Authentic indeed.

After I started to mentor Spencer more and more, we decided to scratch his initial idea or at least greatly improve it. We realized that a ubiquitous todo list app was much more authentic for the both of us to work on and a product that would impact the world in a much more meaningful way. We also agreed that communication within the app was very important and that it would be one of our key differentiators. These collective insights were exciting because it was a sign that Spencer and I could become great cofounders.

But it wasn’t perfect by any means…

As we worked together for a few weeks, I noticed Spencer start to show his age. He impulsively kept spewing out ideas left and right, most of them being pretty bad (with some of them being good 😀 ). To make it worse, he would present himself overly passionate and philosophical to make up for the lack of data he had to defend his views. It was very frustrating, but instead of getting fed up, I stepped back to analyze the “why” of Spencer’s approach. I looked back to when I was his age and realized that he didn’t have a template on how to approach the problem. I then shared this piece of wisdom with Spencer that I learned a few years back:

“As you grow in life, you’re presented with templates that help you think in a different way; a way that is less impulsive and more thoughtful. The best template I’ve used is to think through an idea all the way down to its foundation and then to rebuild from there.”

Spencer absorbed the feedback and overnight he became a completely different person! We resumed the next day by doing the following:

• mapped out how people tackled todos in their everyday lives
• defined all the problems related to getting tasks completed
• listed out the key customer benefits a solution would provide
• mapped out potential features that would tie into the customer benefit and solve their problems

As we went through this exercise, we both pitched ideas that were much more on point. We also transformed into a team thats collective thought was greater than the parts of its sum.