The Lesson Money Couldn’t Buy

It was a warm spring morning in 1992. At the time, I was a pudgy and hyperactive seventh grader at Swampscott Middle School. The bell had just sounded and I was slowly meandering to my next class when my best friend, Josh Grab, intercepted me in front of the principal’s office. For some reason I can’t recall, he got in my face and began to push my buttons. I tried to continue on my way but Josh wouldn’t let up. He was relentless. He went on and on and on. After about three minutes, I had finally reached my tipping point and lost control.

In a flash, everything went white. Before I even knew what was happening, I turned around, made a fist and swung my arm with every ounce of energy I had in me. Instead of taking my frustration out on Josh, which I totally should have, I struck a plexiglass art display containing a chaos pendulum built by students at M.I.T. It was a perfect strike. As soon as my tightly clenched fist hit the display, I heard a crack and felt the large object buckle under the force of my haymaker. Within a second, I knew that I had broken something. Thankfully, it wasn’t my hand but then I realized it was an even worse outcome. The large plexiglass case splintered and one of the large panes split in half. The damage had been done. The severity of my stupid behavior hit home when I came to my senses and realized a group of my classmates were suddenly gathering in front of the principal’s office to witness my carnage.

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What I Read In 2015

Last holiday season, I shared my first annual reading list which was an overview of all the books I devoured in 2014. I’ve always been a big advocate for lifelong learning so I’m constantly trying to practice what I preach by reading one or two books at any given time. There’s no question it’s a big commitment but the investment pays off in so many ways. I find reading helps me go deeper in my work as a VC, develop greater self awareness, build historical perspective, and most importantly escape from the world. I’ve always believed that buying (and reading!) books is by far the best and most rewarding investment that anyone can make in themselves.

Many of the titles on the 2015 list were recommended by close friends, colleagues, Twitter followers and my wife. The topics ranged from innovation to healthcare, history, science fiction and urban planning. As you’ll see, I devoted a considerable amount of time learning about addiction since I decided to get sober in 2015 and led an extensive research project on the topic. Not only was I interested in the science of addiction but also the war on drugs, the rehab industry and new approaches to treatment.

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Transitions

Over the weekend I was fortunate to participate in my first “Medi Club,” a monthly gathering of urban-dwelling meditators. Medi Club is the brainchild of Jesse Israel who wanted to create a safe place for modern meditators that achieved three core goals 1) meditate with like-minded meditators; 2) discuss how meditation relates to issues like relationships, creativity, sex and work/life balance; and 3) deepen practice with new knowledge and interaction with the community. Here’s a little more context on what Medi Club is all about: ‘A Place for Modern Meditators.’ Last night’s theme was centered around transitions in life and work. This particular topic has been top of mind for Jesse because he’s in the process of finding a new path.

For many people, going through a career transition can be both exciting and scary. There’s so much unknown. What are people going to think of me? Can I survive without an income? What do I want to do with my life? Who should I talk with? What would make me happy? Who do I aspire to work with? How long will this take? So much is on the line. For many New Yorkers, a big part of our identity is tied to what we do for a living because it provides meaning and context in a dense city with eight million people. When our immediate existence is challenged, it’s only natural to feel anxiety and uncomfortable because there’s so much uncertainty. In my own career, I’ve found change is never easy but it’s a natural step in the process and it’s required to evolve into a better human.  

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Tinybop: Educating Kids In Every Country

Several years ago when I was at Lerer Ventures, Sam Gerstenzang, our summer intern, recommended  that I meet with Raul Gutierrez, Founder CEO of a Brooklyn-based creative studio called Tinybop.  When Sam explained that Tinybop was building educational apps for kids, I was immediately skeptical because I’ve seen hundreds of companies in the space and my identical twin brother founded a children’s media studio, CloudKid.  After some back and forth with Sam, I begrudgingly agreed to meet with Raul but promised that I would keep an open mind. Over the course of the next two years, Raul and I spent countless hours talking about the future of children’s media and his vision for building the next great education brand.  To Raul’s credit, he was able to transform me from a skeptic to a believer.  Despite the space being hyper competitive with thousands of app publishers, I truly believe that Tinybop is the one percent of the one percent.  That’s why I’m incredibly excited and proud to announce that RRE has led Tinybop’s Series A Financing with participation from TwoSigma, KEC, Brooklyn Bridge Ventures and Kapor Capital.  

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