People often ask me why Michia and I chose the name “Prodigy” for our company.

The truth is, we picked the name over a 30 minute conversation while Michia was walking over to my house. We knew that we wanted to start a B2B company and that we could always change the name later. So we started throwing names out there to see if anything stuck. I remembered that Dropbox used to be called “Get Dropbox” in the early days so I checked getprodigy.com. It was available. We bought it.

Recently, I started thinking what our story would be if we had thoughtfully and deliberately picked the name “Prodigy”. I think that it might have come from my longstanding belief never to underestimate young people.

I learned to never underestimate young people when I was in high school. A lot of this came through my experience playing Chess.

As a high school freshman, I would regularly attend the after...

I just finished Ron Chernow’s biography on Grant and I thought it was excellent. Chernow does a stupendous job recasting the often mischaracterized U.S. Grant as a brilliant strategist and a great war hero.

What I found most intriguing about the book was the accidental nature of Grant’s life.

• His father forces him into a Military career and he enters West Point reluctantly, showing little interest in military matters.
• Grant shows promise in the Mexican American War, becoming an officer. But he is castigated for drunkenness and forced to resign.
• Post-war, he tries his hand at several business ventures and they all fail. Due to his guileless nature, he is repeatedly cheated by others.

At the outset of the Civil War in 1841, Grant is 40 years old and working an entry level role for his two younger brothers at his father’s store. He is impoverished, melancholy, and an alcoholic.

...

I spent the last week in Singapore. A few observations from my trip there:

1. Singapore has a pervasive STEM culture

• From a young age, students are pushed to study STEM.
  Historically Singapore was a very poor country without any natural resources and so heavily encouraged its people Science / Engineering / Business as opposed to the liberal arts. As a result, most Singaporeans have no interest in or understanding of creative arts. For example, there are hardly any pieces of art in the city and I did not see a single festival while I was there. I spoke with an artist while I was there and learned that most Singaporeans did not know who Leonardo Da Vinci was. 


• The government is run primarily by technocrats as opposed to traditional “politicians”. 

  I met a few people from the government and was impressed by their total lack of charisma. Rather than being masters of rhetoric, these...

A few months ago, I spoke at Google HQ for Passion Talks as part of a dialogue about the intersection of faith and work. The videos have finally been released - here is a video of my talk as well as talks from the other speakers.

When I was an undergraduate at Stanford, we used to have a term of endearment for other students: “duck syndrome”. A stereotypical “duck” is someone who appears calm and composed on the outside (above water), but behind the scenes (underwater) is frantically paddling to stay afloat.

Often on campus, you’d see students playing frisbee on the lawn, blasting music, or playing a daytime game of beer pong in front of their row houses. Only later in the evening would you see these same students huddled up in the library, falling asleep on top of their problem sets and chugging multiple red bulls to complete their term papers. The contrast was shocking.

I remember one of my classmates who came across to me as lacking direction. He didn’t seem particularly interested in anything in his classes academic and switched his major in his junior year. I would see him show up parties completely...

Three Lies:

1. I am what others think of me.
2. When I avoid pain, I feel better.
3. What happened is not my fault.

Three Truths:

1. All leaders face criticism and grow from it.
2. When I honor pain, I heal faster.
3. What happened is my responsibility.

When I moved up to San Francisco, the city started opening up my eyes in ways that it had never done before. There is just such a shocking disparity of fortune here that you cannot help but come to terms with. I was uncomfortable with it when I moved up here and I still am.

Well, a few months after moving to San Francisco I was walking home and on the way ran into a homeless guy who asked me for a dollar.
After forking over the money, I asked him - what are you going to spend it on?
“Cigarettes”.

He then asked me, if I wouldn’t mind - could I give him some more money so that he could buy himself some food?

“Actually I’d love to buy you some food. Mind if I join you? Maybe we can go and eat it together?

I hadn’t eaten dinner yet at this point, so I ended up sharing my meal with this homeless guy and his friend.

Here I was, sitting down at a dinner with two humans and thinking...

I recently got dinner with one of my good friends from college. He’s a very sharp guy and successful business owner. Right now he’s travelling the world and running his business remotely. In the past three years, he’s been to something like 50 countries. It turns out that travelling everywhere in the world can be much cheaper than paying rent in San Francisco.

We chatted about life goals and he mentioned that he would probably stop travelling within the next five years of his life and settle down to start his next business at that point. By then, he will have experienced the best parts of the world in his youth and will start his next company as a more cultured, open minded human. I admire that. We read everywhere about and fundamentally recognize the importance of travelling while young, and he is actually doing it. Most of us dream about seeing the world but never do it.

What hit me...