Hug O' War

Last weekend, I was hanging out at my twin brother's house. It was early in the morning and wanted to kill some time so I decided to browse his vast book collection. I came across one of our most cherished books from childhood, Where The Sidewalk Ends by the legendary artist and writer Shel Silverstein.

As I was flipping through the book, I arrived at one of my favorite poems, Hug O' War: I immediately Google'd Hug O' War to learn more about what inspired Shel to write the poem. I discovered that he wrote it to widely express nonviolence and goodness to the world.  That expression really resonated with me.

As I reflected on the poem, the words non-violence, cooperation, winning, surrender, love, happiness and goodness kept coming up for me. I felt those words accurately represent what I value as a human being.

Yesterday, I walked into a tattoo parlor near Chinatown in San Francisco and had Shel's Hug O' War illustration etched on the back my arm. My hope is that it'll serve as a reminder to always love, support, serve and cooperate rather than to fight, harm or hurt. Here's to filling the world with more kindness. I can't think of a better purpose than that.

hugs.jpg

My Favorite Products Of 2016

As a professional investor and lover of things, I’m constantly testing new products and sharing my thoughts with coworkers, colleagues, family and friends. This is a daily ritual and one that I’m passionate about. On occasion, I’ll fall in love with a product because it fills a void and finds a way into my routine.Thankfully, 2016 was packed with super useful and enjoyable products that were made with an insane amount of time, love and care. These products connected me, challenged me, educated me, inspired me, and even fed me. Below is a fairly comprehensive list of the digital and physical products that I enjoyed and couldn’t have lived without in 2016.

Read More

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.

Read More

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.

Read More

The Advice a Cabbie Gave Me The Day I Moved to NYC

On this day nine years ago, I stuffed two huge duffel bags with all my clothes, left my apartment in Seattle for the final time and boarded a red eye in route to NYC. At the time, many emotions and questions were racing through my mind. Do I have what it takes to succeed in the big city? Will I be able to survive in the concrete jungle away from the mountains and lakes of the Pacific Northwest? How the hell am I going to navigate the subway? Will I make enough money to live comfortably? I was nervous about so many unknowns but amped about the endless potential and opportunities of NYC.

When I finally landed at JFK and deplaned, I was still half asleep and took a minute to get my bearings. I then stumbled to the baggage carousel, located my overstuffed bags and hoisted them on to a SmarteCarte so I could make my way to the taxi stand. Since I landed early on a Sunday morning and the airport was virtually empty, I was able to stroll right to the front of the line. As soon as I got to the curb, I was greeted by a middle aged cabbie from the Bronx with a thick New York accent. He got out of the taxi, helped me load my bags into his trunk and slammed the door behind me as I got into the back seat.

We made eye contact through the rearview mirror and he asked, “Where would you like to go, chief?” I fumbled with my tattered itinerary, glanced back at him and relayed, “I’m heading to 48th Street between 7th and 8th Avenue. Do you know how to get there?” The cabbie laughed for a second and glanced back at me. “With all that stuff, you must moving to the city, huh? What brings you here?” I explained that I had just moved to the big city for a new job and was starting a new life. Our eyes met in the rearview mirror once again. He then he became serious and delivered words I’ll never forget:

Read More

My 2014 Reading List

At the beginning of the year, I set a goal to read one book a month in an effort to break free from my routine of reading only tech and startup blogs. My wife, Eliza, had also been trying to get me to read more fiction in the seven years we’ve been together. This seemed like a goal worth pursing and easy to accomplish with very little effort. 

Read More

Products I Couldn't Live Without in 2014

Every year around the holidays, my buddy and fellow Patriots fan, Ryan Spoon, compiles a list of his favorite products. I’ve always enjoyed reading his annual post so I’ve decided to follow his lead and curate my own list. Given I review and test hundreds if not thousands of new products each year, I’m fascinated by the ones that create enough value that I come back to over and over again.  These are the apps, tools and gadgets that cut through the clutter and ultimately made my life more productive, happier and healthier in 2014. 

Read More

What I've read so far in 2014

One of my 2014 goals is to read at least one book per month. To help me achieve this goal, I decided to buy a Kindle Paperwhite so I could read on the subway and have an uninterrupted reading experience while at home.  Like many people, I’ve struggled reading books on Apple devices because the screen isn’t optimal and I’m constantly being distracted by notifications. The Kindle, which I think is the ultimate single purpose device, has changed my life because I’ve honestly never enjoyed reading so much. While I still have ten months until I achieve my goal, I’ve already read more books in 2014 than I did in all of 2013. Here are the books I’ve read so far this year: 

Read More