Category: What I Learned

What I Learned from Joe Boucher

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 second in a series that highlight some of the awesome people I’ve had the privilege to learn from.

Joe Boucher taught me that sometimes swollowing my pride can be the best decision.

I met Joe when I was a 19 year old sophomore at the University of Wisconsin. He was a judge in the practice version of the Burrill Business Plan Competition. I pitched ExchangeHut to a panel of judges that included Joe and he liked what he heard. He told me to contact him if I needed any help. A few weeks later, we got our first potential buyout offer from a competitior. We were really excited.

My business partner and I went to meet Joe out at his law office in Madison. He walked us through our options and helped us decide that we didn’t want to sell the business just yet. As we grew our company, we hired Joe to do our legal work. But we didn’t just gain an attorney, we gained a mentor. I went to Joe whenever I had business questions and he always had great advice. He pushed us to think through each action we could potentially take and what the consequences of each action would be.

One time, a competitor hacked our site. We were incensed and wanted to strike back via police action and publicly expose the individual immediately. We wanted revenge. Joe calmed us down, helped us work through our options and made us think about what was best for our business, not what would make us feel good in the short term. We devised a plan and executed it calmly. We filed a police report, sent a cease and desist letter and I gave an interview to the press. We got what we wanted and looked good doing it.

Another time, we charged a customer about $160 in fees, which caused her to overdraw her checking account. She was furious, threatening legal action and demanding a full refund plus all of her overdraft fees. We were in the right. She was in the wrong. I wanted to offer her half of her fees back, but after speaking with Joe, he convinced me that giving back the full $160 would not only make the problem go away, but we would likely gain a customer. I met with the customer, returned the $160 and he was right. She was a user for three more years until she graduated.

Joe really drove the lesson home when we were selling our business. We had a signed deal and all sides were happy. After closing, but before we recieved our money, one of the parties in the deal wanted to make changes that would cost us a significant amount of money. They threatened to blow up the deal if we did not comply. What they were doing was blatantly illegal and we had them dead to rights with email and phone messages.

My business partners and I wanted to sue. I met with Joe and shared all of my evidence. He told me that I was right, we did have a great case. If we decided to sue, we would likely be awarded a judgement of 2-4x the initial value of the deal, a significant amount of money. He told me he would be happy to try the case for me.

But he told me that a lawsuit would blow up our deal. And we would incur lots of legal costs. And we likely would be in court for at least 2 years. And then if we won, we would have to collect from the offending party and that it would be difficult because they were in a different state. He asked me if I could still be happy with the final amount of the deal at the reduced rate if I didn’t have the original offer on the table. I said yes.

He convinced me that it would be better to swallow my pride, sell the business, collect the money and be happy about having an exit at age 22. After letting my anger subside, I knew he was right and we accepted the lower amount. From then on, I took steps in all future negotiations to never be in that position again.

For the past 8 years Joe has been my attorney, but moreso my mentor. He’s taught me many, many things and helped me through all manner of business and personal challenges. He even put his law firm at our disposition to create the first version of Entrustet. But the most important thing I learned from Joe Boucher was to take a step back, calmly evaluate my options and sometimes swallow my pride. His important lessons have helped me in every aspect of my life and are a major part of my success and happiness today. Thank you Joe.

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.