Tag: jesse davis

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.

Entrustet Acquired by SecureSafe

I’m excited to announce that Entrustet has been acquired by SecureSafe, the market leader in secure storage of digital information and digital inheritance.  Since Jesse and I started Entrustet in a spare classroom at the University of Wisconsin, we’ve had one vision: to build a system to help you to create a plan for your digital assets that you can be assured will be carried out when you pass away.

We’ve done everything in our power to make our vision reality.  We’ve created a product that works and helped people in over 20 countries protect their digital assets.  We’ve helped families of the recently deceased find, access, transfer and delete online accounts and computer files. We’ve shed light on the entire topic of digital estate planning to the general population. We’ve worked with attorneys and legislators to help carve out some legal clarity in an evolving area of estate law.

Over the past three years, we’ve gotten to know the SecureSafe team very well.  They are based in Zurich, Switzerland and their service is used by various Swiss Banks.  We’ve gotten to know a great team with massive experience, and a very similar vision. As we worked together, we realized that SecureSafe had everything that we wanted in a partner.  Their service is top notch and has more features, all backed by the Swiss banking privacy and security they are known for.

It’s a clear win-win: they share our vision of helping you securely store your online accounts and computer files, making them securely accessible anywhere in the world and enabling you to transfer or delete them when you pass away.  Jesse and I will be continuing to work with the SecureSafe team to make sure everything goes smoothly.  We’re both excited to see what our next steps are in our professional lives.

Looking back, Entrustet has been an incredible experience.  I owe so much to Jesse for being an amazing partner.  We have very complimentary skill sets and see the world through a different lens, but at the end of the day we share the most important things in common.  His relentless optimism and ability to take a step back from situations and analyize them have taught me so much.

I still remember the day he pitched me Entrustet in the Wisconsin Business School library with a very rough powerpoint.  I jumped in and we spent the next three years becoming amazing friends.  I really couldn’t ask for anything more in a cofounder, and as Jesse put it, I’ll remember our times outside of the office even more than inside.  What an incredible three years.

Helping start an industry and becoming thought leaders in the space. Seeing users actually benefit from our service, including helping families access and transfer online accounts after someone passed away.  Getting more press than we could ever imagine and meeting tons of incredible people.

Entrustet changed my life.  I learned so much from every part of running the business, but especially from Jesse.  Entrustet took me to New York, San Francsico, Chicago, LA and Austin.  It led me to Chile as part of the beta round of Startup Chile where I met amazing people and discovered a beautiful country.  I got to speak at South By Southwest and even gave a speech in Spanish to Chile’s president at their equivilent of the White House.  Entrustet led me to start Capital Entrepreneurs, Forward Technology Conference and to making tons of new friends.

But we didn’t do it alone.  There are so many people and organizations who helped us get to this point.  We owe so much to our investors, our advisers, Joseph Boucher, Tom Juszczyk, Allan Stern & Adaptive Engineering, Merlin Mentors, our 2010 intern class,  Nathan Dosch and so many more.  I couldn’t do this without the support of my parents who’ve always told me “do what you think is interesting and makes you happy, just as long as you don’t ask us to pay your bills!”  Thanks to my friends who have put up with digital death talk for the past three years and those who were there with me through the ups and downs of startup life.  It’s easy to take risks with family and friends who supports you.  It’s been a great ride and I can’t wait to see what happens next!