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Lifestyles of the Young, Rich, and Homeless

Experience Over Stuff, World Travel.

I’ve lived in the ultra luxurious San Francisco Mint building next to a founder of Twitter. Sarah Jessica Parker was my next-door neighbor in the West Village. We smiled at each other on occasion. My studio-gallery-restaurant-office-loft on Abbot Kinney was the place to be last spring. Summers at the Montauk house were the best. I loved living in an airstream amongst the cliffs above Malibu. But tonight, I am homeless. I am not worried — I’ve got something to share...

In the Spring of 2008, I was finishing my last semester at Stanford. I was printing cash with my first startup, The Comotion Group. I was totally resigned from school. I had been admitted to a secret society at Stanford run by the most elite international students on campus. With a group of my new powerful friends, I traveled to Hong Kong before a quick visit to Singapore for Chili Crab on the way to an Aman Puri holiday in Phuket during midterms. And that was when I met him.

Moments after I met The Pirate.

It was 6am in Hong Kong. I was hanging over, and my jet was seriously lagging. We had arrived the night before, went for bottle service at Dragon-i during model night, and then crashed on a friend’s boat. I was sitting on the deck of this mega yacht drinking a double espresso with a Columbian, then the music started play. It was far too early for music.

A tall blond German guy wheeling speakers pumping electronica made his way down the dock at the marina club trailed by a dozen or so super models. After all, you need company like that when you are going for an overnight jaunt around the South China Sea on a floating monster.

On shore in Hong Kong.

The tall blonde guy, whom I now lovingly refer to as “The Pirate”, and I became quick friends. Over the next few years we’d spend months at a time exploring the world, shopping for sailboats, riding motorcycles through Beijing, talking about the type of life we wanted to live. We were always talking about doing business together. It was a perfect fit. I was a “successful Stanford entrepreneur” and he was an aspiring entrepreneur with big ideas and unlimited family resources.

Flash forward to August 2008. It was 3am on a Saturday in San Francisco. I was asleep. I got a call from a number starting with +852—the Hong Kong country code. It was my old sailing pal from the South China Sea, The Pirate. He told me he was coming to town and needed a place to stay. He told he had a surprise for me. His friend had a friend who knew a guy.

You know how the old saying goes about friends staying with you being like fish: they go bad after 3 days. I figured it was going to be a short-term stay. And I was looking forward to hearing The Pirate’s most recent stories.

He showed up at my door, smelling like mosquito spray (that was the deodorant he elected to use), carrying this very classy, distressed leather bag and one small metal trunk. When he opened the metal trunk, I noticed an odd collection of things—like a fruit dehydrator and a motorcycle helmet—along with three pairs of trousers with built-in suspenders, 4 comfortable looking T-shirts, one pair of worn in boots, a pair of sandals, and a toothbrush. It was all neatly packed. Giving in to my curiosity, I asked him about his recently acquired trunk.

The Pirate and his trunk.

“It carries everything I own,” he said.

I found that very interesting: here’s someone who could afford anything—a home, fancy furniture, all kinds of stuff—and he travels around with a metal trunk and a few personal items. I remember catching, for the first time in my life, the intoxicating whiff of a life not tied down by stuff, of not owning anything, and of how incredibly liberating that could be. I thought about how, much like Mary Meeker’s observation that we are becoming a collaborative consumption environment, the future might not be about owning more things, but owning fewer things. Think about how we live today:

It’s no longer about owning books or songs; it’s about having digital archives.

It’s not about owning a house; it’s about renting one through AirBnB

It’s not about having a driver, it’s about having an uber account.

My friend was living and breathing this credo before it became mainstream. Rather than spending his money on things that held him down; he spent it on experiences. He had incredible stories from our time apart that quickly brought us right back to the days of roaming through the temples in the Hutong just months prior..

The surprise The Pirate had for me required 1 fast car, 3 days of time, and a type of fearlessness known by few. The guy that the guy who knew the guy knew was a friend of Maximillion Cooper, the founder of the Gumball 3000, a 3,000 mile high speed race around the globe. We called up a friend from the Stanford secret society to get ahold of a S550 Mercedes Brabus. We showed up to the Fairmont Hotel as the procession was getting started. We were told the route of the parade, and told to park our car along the route. We were secretly passed a sticker pack which we applied to the Mercedes. And we waited. . .

As the parade started, a Ferrari passed us, then a series of Lamborghinis, and then a gaudy Rolls Royce. It seemed like that was a good time to slide into line. Camouflaged with the official stickers we joined the parade. Success. I got spotted by a friend as we paraded down Lombard street windows down, music blasting. He sent me a text asking if I was racing the Gumball 3000! He couldn’t believe it. I responded with smily face emojicon :)

A guady Rolls Royce on the route from SF to LA

We raced from San Francisco to LA, from LA to San Diego. It was a truly exhilarating experience. And we got the experience for $150,000 less than the sticker price — because my friend knew a guy who knew the guy. And then The Pirate flew to London to stay on someone else’s couch. After another 3 days in of my life, he greatly increased his social capital. Nowadays, I would do just about anything for The Pirate.

A few years later, in February of 2010, I got another call from The Pirate. He was coming back to SF to stay with me. I knew something else life changing was bound to happen. Before leaving for his Asian adventures, The Pirate had lived in New York for 8 years. Up until that point, I had not spent much time in New York. One afternoon just before Valentine’s Day, while he was relaxing on his bed (my couch), sipping a beer, he reminded me about these Italians we’d met in Shanghai. Ah, yes, James and Giancarlo. Those crazy guys.

“They throw these amazing parties, man. They rent out libraries. They have these popup parties.They are throwing one in NYC this weekend. This one is for singles in New York during Valentines. It’s called Drop the Date. The best DJ’s will be there. And the women. Wow. We have to go.”

I had no idea what to expect. We booked Virgin America tickets with no return — just so we had the flexibility we “needed”. I should have known when I asked my friend if we should book a hotel. He just smiled at me and said, “We’ll be fine. There are more couches in New York than in San Francisco.”

Flying into an evening that would change my life.

We arrived in New York City with no real plans. It wasn’t until then that I thought about all the favors my friend must have done for others; all the experiences he must have shared that had allowed him to build up social capital—so much so that he always had a couch to crash on, anywhere he went.

Not long after we touched down in New York, we were invited to stay with this diamond trader who owned a penthouse in SoHo. It seemed that The Pirate was really good friends with this guy. But, really, they’d only known each other for 3 months, after they shared only one weekend together in Paris.

I had never experienced this artist-bohemian-homeless lifestyle before. I was always the guy with the apartment just a little above my means, hosting people when they visited me — building social capital in a different way. I liked the comfort of my own space.

I was babysitting my friend in America, but, really, he was showing me how to live in the world. And this is not stuff you learn operating a start-up. This is not stuff you learn in school. This is stuff you learn through experience, through living without a home. My interactions with The Pirate were pivotal moments in time for me although it wasn’t until many years later that I actually embraced the lifestyle. More on that in future stories…

That night, we went to the party, and it was everything my friend had promised it would be. Something I’ve never experienced. A room filled with interesting artists and musicians and successful entrepreneurs. People who had traveled the world. People with stories. Strange stories. Crazy stories. People who had really lived life. People who, despite their nice clothes, were probably sleeping on somebody’s couch later that night.

I locked eyes with her at some point in the night. She was absolutely gorgeous. I became completely infatuated with her. The next morning I woke up in a TriBeCa high-rise with beautiful views of the city. But, even better, I was next to her.

Later that day, we flew back to San Francisco. The Pirate had an “appointment”. And when I got home, I decided that I was in love with that girl and that I was moving to NYC. I dropped everything. I left The Pirate in San Francisco (I’m sure he had another couch to crash on) and moved out to NYC without a job or plan. A few months later, the “love of my life” moved to London. And, we broke up. But it all worked out. It was all part of the process of me becoming who I am today.

The Pirate subsequently came to live with me in NYC, in Los Angeles, and has yet to really have an apartment. He even started a company that supplies high quality trunks to the worlds top explorers. He is in London right now and invited me out for a visit. He continues to act and live very nomadically. It’s still very inspiring to me. And his being homeless taught me a lot about life.

If he doesn’t update his social media, you have no idea where he is. And for an over-sharer like me, I often wonder what it would be like to fully disappear like that. Because I know he’s happy. And I know the type of life he leads.

For the past few years, my places in NYC, SF, and LA had an open door policy. There is always a key at the front desk. People always stayed over. I’ve hosted tech entrepreneurs, people who have ended up investing in my companies, my future employees, up and coming artists, people I look up to. And because of all that, I can be anywhere in the world, not knowing where I’m going to stay, but still trust that I can find a home.

After my life imploded earlier this year, I shed all of my baggage. I got rid of my places, sold most of my shit, and haven’t spent more than a few days in any location. I’ve been living out of my Jeep. I’ve been apprenticing for people that are illogically passionate about their uniquely unique work. I volunteer my time, get experiences, and share those experiences with the next friend that hosts me.

Living out of my Jeep has been life changing.

It’s freeing not to have stuff weighing you down. It’s also freeing to know that you have a network of people that you have social capital with, who you can rely on, who you can create memories with. Every dollar spent on a fun meal or a vacation with friends or a new cultural experience is another story you get to use as social collateral to strengthen the relationships with people around you. Entertaining people is indispensable. Stories are the new currency.

Other than narcissistic reasons, that why most people share on social media. If you create entertainment value your friends want to keep you around. The world is so damn bleak without entertainment. Most people who are stuck in routines sit down in front of the TV every single night looking to be entertained. If you can bring entertainment to people’s lives, you become special. And no matter how much money you have, you can always rest easy knowing friends will have you over, serve you dinner, and sit down on a couch to listen to your stories.