What I Learned from Jesse Davis

Ralph Waldo Emerson once wrote,”every man I meet is my superior in some way, and in that I learn from him.” It’s one of my favorite quotes. This post is the first in a series that highlight some of the awesome people I’ve had the privilege to learn from.

Jesse Davis taught me the happiness litmus test.

We met in November 2008 during my second senior year at the University of Wisconsin. I was looking for a new business to start after selling ExchangeHut. Two professors and two friends told me I had to talk to him. We met up in the library and he pitched me the initial idea for Entrustet. I was hooked. Over the next month, we worked together, doing market research, deciding if we wanted to start a company together. We had to make sure we liked each other enough to actually commit start a company together. After about a month, we cofounded Entrustet.

Jesse sees the world very simply and we made great business partners. We became good friends and even ended up living together for a year, including six months in Santiago, Chile as part of Startup Chile. All told, we spent the better part of three years together and took his idea from a powerpoint presentation to reality.

From the beginning, I quickly realized Jesse was guided by an important idea. He wrote it on his whiteboard in his bedroom, had it on his computer and talked about it whenever we faced any adversity. After awhile, I began to think of it as the Jesse test. It’s three simple questions to help you decide if you are on the right path:

• Am I acting easily and without struggle?
• Do I enjoy what I’m doing?
• Are results coming on their own accord?

When things were going well for us both personally and professionally, we were working increidbly hard, but we were acting easily. We enjoyed what we were doing. We might work 16 hour days, but it didn’t feel like work. And our results came on their own. Sometimes seemingly out of the blue.

Jesse taught me that when you meet all three criteria, you’re much happier and good things keep happening, almost serendipitously. But if you’re struggling and not enjoying what you are doing, something could be wrong. He taught me to take a step back, to think about why I was struggling, why I wasn’t having success, why it felt like work, and why I was motivated to put in the incredible effort to get a result I wanted.

Now, whenever I am presented by a difficult decision, I use this framework to evaluate my options. I use it in business, in friendships, in relationships, in life. I take a step back, evaluate and then look for the causes of why I’m struggling. I ask myself why I want to accomplish what I’m trying to do. Then I reevaluate whether it’s worth it and whether my strategy is going to get me to the right place and for the right reasons.

Sometimes I find that the struggle is worth it and continue on my previous path, but at least my descision is reaffirmed by careful thought. Other times, I realize that I still want to pursue my goal, but I need to change my strategy. Other times, I realize that it’s just not worth it and its time to move on. Many times when things or people don’t fit these three criteria, I drop them from my life.

I use the framework nearly every day and it helps me think, work and live more clearly. I have it in a post it note on my computers dashboard. It helps me make better decisions. And live a happier, lower stress life. I learned the happiness litmus test from Jesse Davis. And for that I am grateful.