Matty Mo
Matty Mo
Sep 10 · 62 min read

The story of Matty Mo before The Most Famous Artist.

Written 2013–2014; Published 2019

Based on a (kind of) True Story

Before you start reading this — smash the clap button and share this on your social media or bad sex for 7 years ;P

1. Blame Social Media

April 2013

I’m just another failed tech entrepreneur sitting at a bar writing these words. I’m thinking about how our lives are becoming public record forever. We are all fucked if you ask me.

About a month ago, I was a Gawker headline. A video leaked from my “private life.” I got a call at 4 am in India a few days after the video went live, “Dude, you made the front page of Gawker.” And then hundreds of Facebook messages and emails and texts flooded in. All I could do was curl up in a ball in a shitty hotel room in India.

Blame social media? I can’t. I’ve built my career helping advertisers feed messages to consumers on sites like Facebook. And I got damn good at it. But right now I have other things on my mind. I don’t know what is going to happen to me. It’s been about two months.

Tonight, I’m at Gjelina down the street, drinking beer in a dimly lit corner, writing these words. I’m trying to decide how to decide what to do. Anyway, good decisions are made from the heart. And maybe my heart isn’t in it anymore.

My social media accounts will, in a beautifully packaged timeline of events, show you that, yes, I have toured the Mediterranean on yachts, I have flown in jets packed with A-listers, and that I have raced fancy cars across the globe in the Gumball 3000. You may even be led to believe I am a well-connected entrepreneur. I’ve intentionally shared moments I wanted you to see. That is how the world works now. But what those accounts won’t show you is the rest of it — the 99% of life that isn’t so perfect. And it is for a good reason.

Everyone wants to do a tech start-up for the fame and glamour, but contrary to popular belief, you can’t just “get some coders,” “launch an app,” and “exit” for a billion dollars 18 months later. You have a better chance getting an exit camping out in Mark Zuckerberg’s front yard hoping he pays you to leave him alone.

For those of us willing to do the work, we get our shit kicked in every day by all the unknowns of entrepreneurial life. Product, market, team. We are experimenting with other people’s money. It’s just not that easy. The one day we do something cool, something worth sharing, we post about it, and that post represents us — in the timeline of our lives. We are living in a world of snapshots. I will rewrite that last sentence so that it sinks in. We are living in a world of snapshots.

Is it sustainable? I don’t know. Probably not. But I’ll keep doing it. Why? Because my audience, whether out of spite or love, keeps growing. And that’s power. When you wipe away all the bullshit and hype and skewed reality the internet has become, all you have left is people.

One fellow at the bar is shooting glances my way. Maybe he remembers me from one of the shindigs, my Instagram photos, or some conference I headlined? I’m not sure. I’m in no mood to be social tonight. Here’s the fascinating part: I would have a hard time convincing my fans and followers that I am currently depressed. Why? Because last night, I posted a series of photos on Instagram of a few supermodels cooking dinner and painting at my loft. Yes, I posted it for the enjoyment of my audience. But, knowing that the first thing I do right when I open my eyes in the morning is check my iPhone, I may have also posted it last night so that I could wake up to a sweet little bundle of likes and comments and the attention that fuels my addiction these days.

The world we live in today is fueled largely, almost entirely, by bullshit. We propel ourselves from tiny, little kernels of truth to a world of pure embellishment. Why? Because it works.

As I said, the tech world isn’t much different: think about all the fake press reports, vanity metrics, and the rosy quarterly updates created for the people who need to be convinced. Most tech startups out there are teetering on the brink of destruction, but they are always, according to their founders, either “crushing it” or “killing it.” The only thing they have is the perception of success. Some tech entrepreneurs I know are better at acting than they are at running a business.

The world is full of people waiting to be told what to think. And, to survive, the best of us have become masters of persuasion. There’s the guy who’s sold a tech company for a hundred of millions of dollars, and there is everyone else. That’s it. Bullshit and hype are necessary to stay relevant now. And some people have made a ton of money staying relevant. But another result has been arguably the most demonstrative misrepresentation of reality in any era. The lines are so blurred that perception if crafted masterfully, becomes a reality.

2. War & Porn

February 2014

War and Porn is about the Internet. Not the evolution of the Internet in a historical sense. Yes, the Internet got started in the United States as a government weapon during the Cold War. And yes, the Internet saw massive consumer adoption through the sharing of porn files. This text is neither of those stories.

This also isn’t a how-to book or a how-not-to book. This isn’t even a book. You are reading these words on the Internet. This is something else entirely — a new kind perennial parable perhaps. One that I can morph, skew, and augment into a history I deem fit to publish.

I decided to start writing this thing a few months after my worst hangover ever. It is about how the Internet changed everything forever around 2006 and how those changes created an online character called “Matty Mo.”

This is a tale about a place where the truth will always play second fiddle to a good story. It is about how Facebook and its social networking sisters have enabled me to persuade you to get what I want out of life. Well, kind of.

War and Porn is a series of anecdotes, for better or worse, exposing how I strategically shared a few of my best moments, how it led to riches, and how it resulted in my single most excellent fuck up to date. #DrunkNakedFounder

It is mostly about my experiences as an avatar called Matty Mo — an account of the highs and lows of social media, entrepreneurship, and life. Some of you will be able to relate to the stories. Some of you will find them entertaining. Maybe you’ll get tingles when I describe the months I spent in Europe blowing a quarter-million dollars on one of my many mini-retirements.

Some of you will hate me; I am sure of it.

I am not the first to write about the Internet. I guess this is my version of the story of the Internet. This collection of words might save you a few mistakes and save you a few years stumbling around trying to figure out who you want to be, what you want to do, and how you ought to be living.

I want you to realize the power you have because of social media. I am not suggesting over-sharing or under-sharing. I am calling for an elevated consciousness around sharing. I am just telling a story about what happened to me because of social media — how I ended up drunk and naked on the front page of Gawker, how my avatar took over my real life, and what I am up to nearly a few years after I thought my world had ended.

3. Choosing Forgiveness

February 16th, 2013

I was hanging over and completely naked. I got up, stumbled a bit as I caught my balance, and walked to the silver metal Rimowa suitcase opened widely across the villa floor. The few garments I brought were nowhere to be found. Linen pants, a red shirt, khaki cut off shorts, a pair of sandals, a purple and yellow headband; everything was lost. The cash I brought and converted to Indian notes at the airport last night to was all over the floor like some bad Vegas movie. I found my iPhone under some cash. Still naked, I looked at my phone. What! The! Fuck! How could I possibly have 22 messages and 119 notifications?

Outside my front door in Kerala was a system of carefully placed villas draping down a hillside pressed against the Indian Ocean. It was heavenly. Palm trees, hammocks, staff dressed in elegant white sarongs scurrying around. I wanted to take a picture to share on Instagram to make sure all my followers knew how awesome my vacation was going to be. Shit, I left my phone. Fuck it. As I walked over to the pool restaurant area, I got smiles from the staff. I smiled back. They whispered amongst themselves. They laughed and turned away, embarrassed, or something. Strange.

And then I saw him. My old pal Jesse Thomas. My traveling buddy; a guy I met on Facebook two years earlier. The fat gap-toothed fuck was floating in the pool. With a huge smile, he shouted, “Matty! Duuuude . . .” I sat next to him on the ledge of a pool that looked West at a beach that sent nostalgic tingles through my body. Maybe it was just the shakes. I started to feel sick to my stomach. He started laughing. Uncontrollably laughing. “Last night was craaazy,” he said with a shit spitting grin on his face, “you were . . .”

As he started in, I phased him out and tried to retrace my steps. I couldn’t remember the end. Did I blackout? I landed in India at sunrise. I was drunk from all the champagne and whiskey in first class on my flight. I met Jesse on the beach.

Jesse reminded me of how drunk I got. He motioned for me to grab his phone on the chair next to the pool. I opened his photo app, and I took a look. Photos of us drinking whiskey. That’s right; I bought some Blue Label at duty-free on the way out of the airport. I was celebrating! Sunrise. The beach. Palm Trees. Pretty. Photos of me. I look drunk — more pictures of me. Wait, why does he have pictures of me naked. And videos? Why am I holding fists full of cash in my hotel room with hotel staff by my side? Why is there a screenshot of my business partner telling him to take down the video? What the fuck is going on. My eyes lifted from the screen. I wanted to kill Jesse.

He finished, “but don’t worry; I erased them all. I don’t think anyone saw it. You will be fine.” Without words, I got up and walked back to my villa. I quickly realized what had happened. My pal Jesse Thomas had posted a series of images and videos of my vacation behavior to his hundreds of thousand followers on Twitter, Instagram, and Facebook. Why would he do that? I was ruined. I was in the process of selling my tech company. I was a few days away from finalizing the paperwork. That is why I was celebrating. I was about to sell my company! Maybe no one saw it. It is Saturday now. I hope no one saw it. I opened up my phone.

Everyone had seen it. It was bad. My friends, family, employees, and advisors had all seen it. My investors had seen it. Texts, Emails, and Facebook messages.

“Are you okay?”

“What is going on?”

I started erasing comments and removing photo tags. I responded to messages. One message was from Sam Biddle, a gossiper at Gawker. He wanted to know what was going on. I replied to him as if it was no big deal. And I waited.

We had an itinerary for the rest of the weekend. Over the next few days, Jesse tried to convince me that what had happened was no big deal. But it was, and I knew it. I was ruined. I distinctly remember him preaching over and over, “I am a PR expert.” Yeah, fucking right. He even offered advice, “When stuff like this happens, you need to hold your ground and stay still. It’s like an avalanche. We are climbing a mountain, and an avalanche happened. We have to stay still and keep our ground.” Our ground? “ We will keep climbing, and we just need to wait for the avalanche to pass.”

I didn’t know what to do. I felt betrayed. It was like my thousands of friends on Facebook had instantly become my enemies. I became paranoid. I was embarrassed. I contemplated disappearing. I considered even worse.

4. Rolodex

1985–2004

I guess it all started with my grandfather and his losing of more than 100 million dollars. That amount of money is also known as “Fuck You” money — which essentially means that you no longer have to play by anyone else’s rules.

So, he wrote his own rules, made the world his playground, and lived the dream. He built a beautiful home on the face of a cliff in Newport Beach, owned a ranch in Idaho, spent the winters skiing at his chalet in Switzerland, bought a monster yacht (which he named The Resolute), and picked up a handful of Porsche dealerships, just for fun.

He philandered around the Mediterranean, frequenting the most beautiful ports in the world, flamboyantly entertaining CEOs and foreign diplomats. The handwritten letters from royalty personally thanking him for his hospitality often came attached to pictures of The Resolute moored in each author’s respective port. And, along the way, he had a knack for scooping up the most beautiful women in the world to join him. I know this because I had heard the “stories” and seen the photos.

He told amazing stories. And it was because of him that I began to consider the difference between who people are and who they project themselves to be.

When I was a young boy, I saw a famous picture of Steve McQueen on a motorcycle and mistook him for my grandfather. That’s the level of cool he’d managed to sell people on. However, the story goes he spent more time selling that image to the world than actually maintaining his professional and family life. The question remains, how can you really lose $100 million?

On a whim, he invested all of his money on planes, using the family bank as collateral. He got the deal of a lifetime on a fleet of airplanes meant to service the Bermuda Triangle. I can’t make this shit up, and I don’t need to. He was able to make the deal because no one else would buy the planes. No one else would buy the airplanes because they were faulty. He spent my inheritance on some giant, winged tin foil that couldn’t fly.

With no more cash and an extensive collection of extravagant stuff, the family began to fall apart. Unable to sacrifice his public image, he kept his lifestyle going, entertaining guests on his yacht until the bank took it all away.

Several interesting things began to unfold. My grandmother, a talented artist, exiled herself to Tahiti to fulfill her passion of painting. She made a living off her art until her hands turned orange from papaya poisoning. She could have become a famous artist. But, instead, she died alone on one of the islands in a studio full of watercolor paintings of Tahitian landscapes and portraits of people she’d met along the way.

As for my grandfather: the story goes his house in Newport Beach fell into disrepair in 1984. The land was bought by tech executives, who would later rebuild on top of the ruble. Everything else was liquidated. The party ended. Memories faded. I had hoped he hidden away some of his cash in offshore accounts, but after his death in 2011, no such funds surfaced. So much for winning the sperm lottery, I guess.

He hardly spoke to me as a child, unless it was about business. As a young boy peering up admirably, I learned about managing employees, fundraising, and inter-company politics — the works.

Years later, after getting accepted into Stanford, I felt like my life was on the right path. As we pulled up to the magnificent palm tree-lined entrance of one of the most prestigious universities in the world, my grandfather began to share this, “Matty, the most important thing I can ever tell you about being successful in this world is this: you must surround yourself with people much smarter than you. You must persuade these people to love you, to trust in you, to invest in you. The smartest thing you can ever do is keep a Rolodex filled with all the contact information of the right people. Guard it with your life. Rely on it. Reach out to these people as strategically and often as possible. The right Rolodex is going to make you successful.” He helped me move in, and then he left.

On the first day of class, I heard about The Facebook. It was just picking up momentum as I started college in 2004. I became obsessed. It would eventually become my great and trusted digital Rolodex. Ironically, the advice, meant to make my life better, became an unhealthy addiction I am still battling today.

5. Stanford

Fall 2004

Freshman year, I got placed in a dorm called Burnbank, one of a series of buildings that make up Stern Hall. In the common area in the basement, we had a pool table, some couches, and someone always had a little bit of weed — the necessities a group of youngsters needs to get stoned, tell stories, and discuss changing the world.

Each of the people I met that year, I would describe as “uniquely unique.” But they had a different description for me. They called me a “fuzzy.” The term was playful but was meant to describe a student who was taking less worthy course work than engineering, math, or computer science. And since I was taking mostly art and communication classes, I was an obvious “fuzzy.”

I got a wrestling scholarship after a few strategic finishes at high school tournaments. I sold myself to the Stanford wrestling coach on what a great addition I’d be to the team. My SAT scores were only 1180, and I don’t remember ever actually reading a book in high school. I didn’t give a fuck about school. I had been granted early admission to Stanford before my senior year of high school had started.

In the beginning, I was just happy to be there. I thought I knew it all before I met my friends at Stanford. I quickly learned from them that there is always more to learn. And I learned that real knowledge is understanding that you know nothing.

I’ve always been a bit of a dreamer. About halfway through my freshman year, I had a vision of who I wanted to be. I wanted to make movies! Although I wasn’t the smartest or richest or most accomplished kid in the room, I was determined to hack the system.

My freshman year was the most transformative year of my life. I had sex. I did drugs. I learned about stuff that excited me. I read books! I was talking big picture. I was talking about making money. I was thinking about starting something. Admittedly, I was full of shit. But I was also full of life.

6. The $1,000 Bet

Summer 2007

Most people complain about nepotism — that is, until the moment they benefit from it. I was a junior in college. I’d figured out how to beat the system, YouTube’s system that is. A classmate helped me figure out a way to “hack” the front page of YouTube. Back then, if your video is on the front page of YouTube, you’re an instant star. But, once my videos were on the most view list, I was heartbroken by the negative feedback from anonymous assholes on the actual content of my videos.

My favorite criticism: “At 0:37 I feel like I’m going to have an aneurysm. Keep your day job.” Well shit.

My movie-making dreams were crushed, but I knew there was something there. If I couldn’t make good videos, the next best thing would be to get involved in the industry.

Our first meeting took place in the kitchen of his home in Calabasas. I met “him” through a bit of nepotism. He asked simple and direct questions — like, “What are your goals?” — And I gave long-winded, rambling, shaky responses about my desire to make films and create content. I drove home from his mansion that night thinking that I would never have an opportunity to meet with him again.

I was wrong. The next morning, I got a call from his assistant. She said that he would like to have lunch with me. We set a time and date. The plan was to have lunch at The Commissary, a renowned restaurant on 20th Century Fox’s Lot, the place where the executives wine and dine the stars.

I showed up at the restaurant, said my name to the host, and was quickly ushered to “his” table. While I waited for him to arrive, I looked around the room — my eyes darting from table to table until they froze on one. Johnny Fucking Depp.

After a few minutes, my future employer (not Johnny Depp) joined me at “his” table. He got right to it.

“So what have you been working on?” he asked.

I pulled out my computer and started to show him a reel of all the short films I’d made in school.

“Matty,” he said, “put that away. What you need to do is work in my market research department. You’ll gain insight into how the entire industry works. You’ll learn how we test movies, how we tell the right stories through movie trailers; the stories people want to hear. We are all about selling tickets to the biggest party every weekend. And for that to happen, we need to sell the party that everyone wants to be at.”

The meeting was over before lunch had even started. You can imagine my frustration when, after three weeks, I was buried in a closet doing excel data entry, not learning a damn thing. I considered walking away from the job, but then, one day, I heard this woman from marketing in the hallway talking about how they were going to spend $250,000 to get the trailer for a movie on the front page of YouTube. Boom!

I charged past his frightened executive assistant and into his office.

“Here,” I said, taking my first payment check out of my pocket and slamming it down on his table. “Here’s my thousand-dollar check. I’ll bet you that I can get your trailer on the front page of YouTube without you having to pay $250,000. Give me a shot.”

More of an old-fashioned businessman, without much web prowess, he seemed skeptical that I could do for free what was going to cost him $250,000.

“You might be surprised,” I said. “If not, you win $1,000.”

“Okay get out of here. I need to take this call. Hello . . .”

Walking out of his office, I heard him scream “MORE FUCKING BLOOD!” at the trailer editor on the other end of the phone. His executive assistant led me to the creative department to get the proper video assets. That evening, I uploaded the trailer to YouTube and started the magic.

The next morning, at 7 a.m., far earlier than I usually woke up at that point in my life, I got a call from the executive assistant: “Matty, he’s on the line for you.”

“WHAT THE FUCK DID YOU DO?” he barked.

“What do you mean?” I said, bewildered in the early morning hour and slightly frightened.

“I got legal all up my ass. They think the movie got pirated. How the hell did you get 7 million views on the trailer overnight? It’s on the front page of YouTube. People don’t believe it’s real. Get in the office right now.”

I hung up — dressed quickly and drove to the office, expecting to get fired, imagining the worst. When I walked into his office, his feet on his desk, and he was clapping and laughing.

“You’re a goddamn genius,” he said, instantly calming my fears of getting fired or sued or murdered. And then, handing me a document, he winked and said, “Here’s a list of all the movie trailers we’d like to run through your company. Let’s get started. I want to introduce you to my friend, Ashton.”

That thousand-dollar bet turned into a seven-figure business we ran out of our dorm room. We called it The CoMotion Group. The rest of the summer was like something out of a movie. It was the first time I’d made real cash on my own. It was the first time I could buy a bottle of champagne at a night club. For my birthday, I rented a hummer limo and threw a party at one of my client’s houses in the Hollywood Hills. I got introduced to the heads at all the major movie studios. And then, when summer was over, I entered my senior year of college with a pocket full of cash and a head full of confidence.

7. The Facebook Class

Fall 2007

I was named Chief Creative Officer of Sharethrough, mostly because my more experienced business partners took all the real titles. This is the story of how I became a co-founder of my first venture capital-backed business.

It was an exciting time for Facebook. They had just launched an app platform, which allowed third-party developers to build applications, using Facebook’s data, to create a more “social” experience for users. This technological development at Facebook gave way to the creation of the extraordinary, once in a lifetime class at Stanford — CS377W: Creating Engaging Facebook Apps.

There were only 75 spots available for the infamous Facebook Class taught in the Persuasive Technology Lab, run by the renowned B.J. Fogg at Stanford. Professor Fogg was described in Fortune magazine as one of the “10 new gurus you should know.” The Persuasive Technology Lab creates insight into how computing products — from websites to mobile phone software — can be designed to change what people believe and what they do.

I knew that I needed to get into that class. The class would teach us how to “create, launch, and optimize web applications. Guided by the instructors and outside experts, students would work in small, interdisciplinary teams to conceptualize, develop, and distribute new functionality to Facebook users.”

But 200 people showed up on the first day. I had never taken a class in the Persuasive Technology Lab. I wasn’t qualified to be given one of the 75 seats. I didn’t know computer science. I wasn’t an MBA student. I had never managed product development. So, I started selling: persuading everyone that I would be a great partner; that, sure, I may seem unqualified, but that I was unique; that I could offer a different and original perspective; that I would work harder than everyone else; that I would make them all proud. I now know, had I not hustled to get into the Facebook Class, my life would have been very, very different. I’m sure of it.

The first day of class was overwhelming. I was in over my head, but I could feel the potential — the intelligence. And then, when we were asked to pick our partners for class projects, I could feel the opportunity. I didn’t know much about application development — an apparent weakness from the start. But I did know how to use Photoshop, which gave me a skill set that was valuable to design-challenged computer programmers. I also had relationships with brands and movie studios through the company I started during my summer internship.

So when we broke into groups to pitch ourselves to each other, I focused on confidently selling myself around my strengths.

Eventually, I found a connection with two brilliant Indian dudes, who “needed” me to help them design a popular application. I knew our trio would work well together, and when they agreed to work with me, I considered it my first experience — of many to come down the road — building a team of technical talent.

Our first app — a complicated, turn-based card game that many of you have probably played in real-life — War — failed miserably.

We took a step back, refreshed our minds, and observed that complex was not the answer. Everything simple was winning. Lightweight, fluffy, fun Gifting Apps — Send a Kiss, Give a Hug, Send a Flower, etc. — made up the first application category on Facebook that was wildly successful. In a nutshell, any time one user engaged a “friend” with a Gifting App, that friend would be invited to try out the app and invite more friends.

This is an excellent time to introduce K Factor: the equation used to measure virality, originally used to track the spread of disease borrowed from the medical field of epidemiology. This is some of the growth hacker shit I learned during the Facebook Class.

The general idea is that there are a certain number of people exposed to the app, who then share the app with some additional people. Some of the newly exposed people convert to being a user of the app, and the cycle continues. If you get K Factor over 1, your app will continue to grow organically.

So after our failure with complex, we decided to build simple. We started an app called Share the Love, which ended up being one of the top apps in the class, growing to over 1 million users in less than four weeks. It seemed that overnight we were generating ad revenue, which was damn exciting to experience. All just by keeping it simple and allowing people to “share the love.”

The Facebook Class was a huge success. As a whole, our applications amassed 10 million users in ten weeks. You can read about the success stories from the class in The New York Times. But, as I remember it, ten companies were started from this class, and five sold for life-changing amounts of “Fuck You” money for my young entrepreneurial peers.

The class was an introduction to entrepreneurs at Stanford, and it was also an introduction to the venture capital and the advisor community in Silicon Valley. Every week, there would be guest lecturers and guest speakers who were some of the most prestigious pioneers in the industry, giving us a perspective that we could NOT get in undergraduate, or business school — because we heard case studies directly from people who were in the weeds, not just memorizing case studies from a book. We were living in case studies. We could ask the masters of our universe all the questions we wanted to. It was the coolest experience of my formal education.

Around this same time, my business partner in The CoMotion Group published a TechCrunch article, “The Secret Strategies Behind Many ‘Viral’ Videos,” which exposed some of the grey-hat strategies people might use to “growth hack” YouTube. The content of the article was not well received, but through the fallout, I learned that “no press is bad press.” That article generated a tremendous amount of new business for our company, and I became obsessed with getting more press.

Shortly after that, because the industry had become interested in all the Facebook hoopla, a local news crew scheduled a day to come into the Facebook Class. When I heard about it, I immediately persuaded the TV crew to allow me to be on camera, to be one of the interviewees.

One of the quotes from my interview aired on local Bay Area television: “This is the class that’s going to bring my business into fruition.” And, as a result of this little digital artifact, and the bit of cash I had made from The CoMotion Group — I was able to advise and invest in companies, instantly giving me credibility in the industry. I was granted access to some of the best entrepreneurs in the sphere and eventually rewarded with substantial financial gains. One company that I advised and invested in sold to Google for a reported 350 million dollars in the summer of 2012. That acquisition is when I got my first bit of “Fuck You” money.

I find it interesting that I was quoted as saying that The Facebook Class would “bring my business into fruition,” when it could have very well been the video of my quote that ultimately brought my career into fruition and opened so many doors for me in the future. But, either way, it doesn’t matter. The result is always what matters. And a little storytelling got me to where I wanted to be.

A couple of other things happened. One of the businesses that sprouted up as a result of the Facebook Class was, basically, an app factory (called 750 Industries, named after the pub at Stanford) where the founders churned out large quantities of apps in hopes that one or two would strike gold. And, it worked. They had hundreds of apps generating significant revenue each month.

The CoMotion Group had reached a bottleneck. We needed more eyeballs to scale our revenue. All we had was a video distribution consultancy. 750 Industries had a shit-load of traffic and founders with excellent engineering skills and enough business knowledge to model out the financials and pitch VC’s. It was a perfect collaboration in the making, so we merged our two companies. That was my first “exit.” I was 22, and it felt terrific.

Because of our traction, the merged company became an ideal target for top-tier investors. The company took on funding totaling something like 38 million dollars to date through multiple rounds of financing. But don’t quote me on the exact number.

Through this process, I got hands-on experience. I learned about raising a round, selling a company, getting office space, building products, and hiring a team — a crash course in building a successful startup: the real operational shit. And it all just evolved out of the Facebook Class.

This is where things start to get out of control.

8. Billionaire Boys Club

Spring 2008

When I go out to eat, I prefer to eat alone. Especially at expensive sushi restaurants. One of my most memorable meals at a restaurant was a solo experience. Nibbling on some fresh sushi at Kaygetsu on Sand Hill Road (back when it was still open), while tapping around on my iPhone (a new offering then), I glanced up and noticed that the only other person sitting at the sushi bar next to me was Steve Jobs. He was a few seats away. Not only was he alone, but he was reading a book, like a physical, tangible, hardcover book. The creator of the iPhone reading an analog book!

While pretending to be unaware of him and preoccupied with my iPhone, I snapped a quick shot of him and posted it to Facebook. Then I just observed him (I think he observed me, too), sneaking glances whenever I could, soaking him all in.

Something was very different about this man. He sat like any other ordinary human would sit. He sipped his water normally. He brought a piece of sushi to his mouth in the same way I would. But, still, he seemed very different, as if everything in the room — the chopsticks, the ceramics, the chefs, the art on the wall, the fixtures, even the shirt he was wearing — was created to compliment him, to be his support system, to be his loyal audience. I thought about it for a little bit longer, until, finally, I figured out what it was.

Steve Jobs was a fucking billionaire.

I was first exposed to a large group of billionaires at Stanford. One guy I learned the most from, became my dear friend and introduced me to that scene.

I call him “007” because he is the type of guy who is full of surprises.

And after a few classroom sessions with 007, and getting to know him, I had this feeling he was someone special. I didn’t know of his wealth at this point in our relationship. He was super humble about it all.

And then the day came when 007 moved our relationship from the classroom into the world of exclusive dinner parties, cocktail events, and retreats with a whole new group of people — all of whom reminded me very much of 007.

I started witnessing, for the first time, this other side of university life that was reserved for the privileged. And because I had some money, I was able to participate in the finer things. I could say yes to invitations to the Playboy Mansion and take trips to join my new friends racing Lamborghinis. I could buy a bottle of champagne and not worry that my parents would see my credit card bill and freak out. I was spending all of my money, but I was spending money to eventually make more money down the road, to build relationships, and to gain experience.

One evening, 007 invited me to apply for a secret society. The gossip surrounding the mysteries of the organization never seemed to tire.

“It’s like the Skull and Bones of Yale.”

“This society has been around for 182 years.”

“Once you are a member, you can fly to any place in the world and there will always be someone waiting to pick you up in a Rolls Royce and take care of you for the duration of your stay.”

“Members have to know how to say cheers in every language.”

The first meeting for those invited to apply that year started at the Tree House (a local bar on campus). The plan was to meet for a drink then get on a chartered bus to an unknown destination. We were told that the older guys in the society had paid for the whole thing.

Knowing what was at stake (ski trips, parties at mansions, and trips out to private vineyards with all the right people), I decided I should try to make a great first impression by differentiating myself from the very beginning. So I pulled a move that I thought would impress the members of the secret society. That was my first experience with social capital playing a role in developing relationships that were many tiers above my current status.

And as my confidence grew within my new community, I started to think bigger. At the time, I was working with this professor from USC focused on building mobile app startups. Together, we won a contract to make an app that managed bookings for the small private airline. I saw another opportunity. Instead of taking payment, I asked to fly around on private jets. Not because I could afford it, but because I hustled for what I wanted. My billionaire friends flew around in private jets with their parents. But now they saw me flying around on jets without my parents. They were very impressed. It’s obvious, but Vegas is a lot more fun when you arrive on a private plane without your parents.

007 exposed me to parts of the world I would have never seen. He made me realize that anything was possible. I learned a lot about big business, macroeconomics, horizontal integrations, hostile takeovers, billionaire stuff (not start-up problems), all of which allowed me to have more intelligent conversations with folks I looked up to across the board: be it the investor community in Silicon Valley or the father of a prospective bride.

My interactions with 007 elevated my consciousness to a point where I could talk to anyone about anything. The ability to speak to anyone about anything — whether it be about fine dining or riding dirt bikes or private aviation or shooting skeet — does make a difference.

When we graduated, 007 sent out an email to us all. “As close friends I think it’s important we all keep in touch, remembering to keep a check on each other, making sure we’re all walking the right path, and doing the right thing.”

Though the crew is sprawled out around the globe these days doing MBAs and running empires, we manage to stay in touch via Whatsapp. After my Drunk Naked Founder incident, 007 pinged me. I was too embarrassed to respond.

9. Mini-Retirement

Summer 2011

I was living in New York. I had stopped working, traveled the world, done some consulting, and changed my name on Facebook to Matty Mo.

I’d just moved to the city because I thought I was in love with a woman. But shortly after I arrived, she moved to London. So I decided to focus my energy on business. I found a job as the Director of Social (what a stupid title) at a large media conglomerate that was moving into the social advertising space. When I walked into the office on my first day, my employer handed me a stack of Excel spreadsheets and a boring list of administrative tasks.

Shortly before accepting the position, I consulted a guy with we will call “Boss” — a three comma club entrepreneur and a person I deeply admire — for some advice. The most important thing he said to me was, “It’s impossible to get what you don’t ask for.”

Boss also reminded me that “if you know what your customers want, they will pull the products off the shelves, instead of you having to push them.”

Soon I was hosting up to five meetings a day with different CMOs and heads of agencies — asking them questions, listening, discussing the competitive landscape, learning about their objectives — and, without them knowing it, I was soft-selling them into buying more of my employer’s services.

I flew all over the United States and Europe for meetings, quickly building up my unit’s revenue line. I was making more money in one month’s check than I’d seen in an entire year. It was my first experience having lots of cash continuously fill my bank account. I didn’t know what to do with it all. So I started buying expensive shit. Then I began buying multiples of the same expensive shit — like 15 pairs of the same John Varvatos shoes and a new suit for every meeting. I became obsessed with luxury travel gear like Tumi, spending thousands of dollars on suitcases, satchels, and totes. I was obsessed with how many frequent flyer miles I was accruing; it was a game, and I wanted more points.

I started eating at high-end restaurants, where the presentation was paramount. My steak was served in even slices, blushing pink, resting across each other on the plate. My sushi served in a dazzling display of rainbow colors. The staff said things like “garnished with . . . [something unnecessary]” and “resting on a bed of . . . [something wonderful]” and “infused with . . . [probably truffle butter].”

I documented everything. I took photos of my shoes and suits, my luggage, my watches, my food. And then I shared it to the world on Facebook and Instagram. I also began to post photos and the locations of all the agencies I visited for meetings. All of it defined my online persona. I didn’t realize how much of a monster I was creating. The Tumi baggage I was collecting was becoming my psychological baggage. And now I’m sure that my new fascination with stuff, my new social media presence, and the new money in my bank account combined with my complete lack of self-awareness, contributed entirely to the most significant downward spiral of my young career.

The problem with stuff is that there’s always more of it. When I got bored with my stuff, I began to seek more stuff. I craved continuous adventure. I got tired of talking to the same customers. I wanted to go out in the world and meet new customers — my future customers. I wanted to eat at more fancy restaurants and post the photos online. Everyone in my online world knew me as this guy who knew everyone in the ad-tech world and dined at fancy restaurants every night. I wanted to keep perpetuating that image of myself.

Why? Because it was thrilling and fun and ego-stroking. I started getting off to the photos I posted of myself standing in front of a world-renowned agency or an exclusive guest-list-only restaurant — feeling a little zap of pleasure with each additional ‘like’ that would accrue. But I was feeding the beast. Nothing was ever satisfying enough. I could never satiate myself.

And although I was spending like crazy, I’d saved enough money to be independent for a while. So after about a year of hard work selling how cool I was, I walked away from my job and substantial salary to do absolutely nothing but go out for fancy meals. Where to start?

I decided to book a trip to Europe. Paris, I thought. Yes, Paris, will be a good starting point. I had a friend in my digital Rolodex, living in Paris, who I could call on for some help when I arrived.

My friend — a fascinating yet unsavory Frenchman (he wasn’t allowed in casinos because of his gambling problem, and he ran one of the biggest pornography websites) — had a beautiful apartment in the heart of the 16th. I reached out to him, and, although he was going to be frequently traveling, he invited me to stay at his place as long as I wanted.

Now that I no longer had to worry about work, I could focus on cultivating my online persona. My first night in Paris, I couldn’t get into this exclusive club. Two giant bouncers, standing in front of a sturdy oak door, were faithfully opposed to my entry — no matter what I offered or promised with my limited high-school level French. But throughout my 15-minute loitering period, I observed that the bouncers were indeed quite excited to see other guests — most of whom rolled up to the curb in luxury vehicles, wore bright colors, and, as the doors opened for them, they high-fived the bouncers on the way inside. I had no car. I wasn’t dressed well. I took note.

The next morning, I laid out a new Gucci flower suit. Next, I took a cab to a luxury car rental company and rented a brand-new midnight blue 911 turbo Porsche convertible.

That night, I went back to the club, this time wearing my flower suit (with a copy of the Harvard Business Review rolled up in my back pocket) and driving my Porsche. I pulled right up to the curb in front, got out of my running car, nodded to the valet, walked towards the same two bouncers like I owned Paris, and then high-fived them as the fancy oak door opened for me. Wow, it worked.

Inside the club, I immediately bought a table and ordered a couple of bottles of the most excellent champagne in the house. Once the bottles arrived, I made friends very quickly, and the waitress was one of them. A group of French people, maybe one of the same groups who I’d seen enter seamlessly into the club the night before, came over to meet me. We shared some laughs and some champagne. We got drunk. We told stories. I practiced my French. They told me to give it up for good. We ordered more champagne. An American couple approached me. The guy, who’d noticed the Harvard Business Review in my back pocket, said that he’d graduated from Harvard. I poured him and girlfriend some champagne. I introduced them to my new French friends. I come to find out, as we get to talking, that the American guy somehow got rich off of Crocs, the rubber shoe company that IPO’d for 2 billion dollars.

I invited the whole crew back to “my place” for an after-party. Everyone agreed. We partied on. Late the next morning, I got a call from one of my new French friends, inviting me to join his group for brunch. Boom. One flower suit. One Porsche. One Harvard Business Review. A couple of bottles of expensive champagne. Just like that, I was integrated into the Parisian lifestyle with a group of new friends.

The next six months carried on to the same tune, and I had my camera handy to record all of it. I dated models, attended lavish weddings, got massages, ate fine food, drank fantastic French wine, and drove the Porsche out to Normandy for some lobster and high-stakes gambling. But then I fell in love and spent the rest of my money chasing a girl around the Mediterranean.

Almost broke, depressed and lonely in Istanbul, I lay in bed one night watching Mark Zuckerberg announce, on live chat, this new feature on Facebook called Timeline. I remember being struck with the realization that we’d reached the point where history would be forever preserved through social media. My social media, at that moment, was a goddamn collage of egotistical, lavish adventures, and I had nothing to show for it. I didn’t even know where all those pairs of shoes and suits had disappeared to. I figured I’d lost them somewhere along the way. Suddenly, I became more conscious of the mark I wanted to leave. I had newfound ambitions to create a legacy — and not just one which involved never-ending photos of fancy meals.

Mini-retirement was over. Time to go back to work.

10. Back in the Game

Fall 2011 — Winter 2012

At my burn rate, I was running out of money very quickly. While I was semi-retired in Europe, I’d decided to keep my apartment back in New York vacant so that my friends, traveling through town, had a place to stay if they were in need. Throughout my mini-retirement, several of my friends ended up using my loft. Word got around that I was back in town.

My well-connected friend in the investor scene urged me to start a new company in the same industry I’d just exited. “It’s so hot right now,” he reminded me. “Investors are nuts over the space.” He was heavily pursuing me because he had the perception, owed to my social media presence, that I knew all the right people and was wildly successful.

Before I knew what was happening, I was very much involved in the same scene again. I took on some old clients to generate money and did very well very quickly. In a matter of months, I’d started another company. I called it Alphaboost.

I effortlessly raised a million dollars because I had a legacy — the money guys associated me with success. Confident in my abilities, I started getting customers and building a business. I knew how to do it.

After I locked funding, I rushed into hiring a bunch of people — jumping back into an industry that I’d left for a reason because everything just seemed so easy. Everything seemed easy, but disaster was just around the corner.

11. Dick Move

Written March 2013

The problem with a culture hungry for, and fueled by snapshots, is that we apply meaning to things and people based on one tiny component of a much more complex system. Essentially, we are trading the holistic experience for chewable bite-sized pieces. When those bite-sized pieces make a hero out of you, life has never been better. But when those bite-sized pieces make a villain out of you, life has never been worse. Trust me. I’ve lived it. And, given the attention span of our generation, you can be a hero one hour and a villain the next.

During my downfall, Gawker had a considerable influence and a massive readership despite being a bunch of shitty life-ruining gossip most of the time. I was in the process of selling my company when the Drunk Naked Founder story broke. And that was because I made the deliberate decision to get out. I wasn’t happy, and I could see the market opportunity closing.

So a year and a half after rushing back into the game, my dick is all over the goddamn Internet, I’ve been forced to fire my people, shut down my company, and email pissed-off investors. The last few employees got one-way flights elsewhere, leaving me alone in a vacant, unforgiving, depressing building that was once flourishing with ideas and opportunity.

I continue to be haunted by the possibility that this India bullshit may leave a permanent scar on my record. I can only take the lessons I’ve learned, the knowledge I’ve acquired, and keep moving forward, keep trying to make myself better, keep trying to innovate, keep trying to make a difference.

I know now that I would’ve never allowed myself to get to that level of stupidity in India if I was happy with myself, and if I was passionate about my future. After my mini-retirement, I didn’t take the time to think about what I wanted to do and who I wanted to be.

12. Love, Death, and Instagram

Originally Published Summer 2013

On August 10th, I was involved in a high-speed rollover accident on the famed Autobahn outside of Berlin, Germany on the way to my “new” friend’s party at his country house. Our back tire popped at 100mph + speeds which sent us into a 360° slide across the freeway towards the earth wall on the right side of the highway. We hit the wall, rolled over twice, and landed right side up against the embankment. While watching the wall approach, I knew I was going to die. I braced for it. As we rolled, I saw glass, luggage, tires, and metal flying everywhere. I heard painful screams and alarming sounds. When we landed, I looked around and asked if everyone was okay. The driver and passengers’ heads were still in airbags. The passengers in the back seat with me looked banged up, but I could see no serious physical injuries. I got out of the car by kicking my door open. I looked at my limbs, felt my head and face. I searched for blood. None. Thank God. I immediately looked for my passport, wallet, and phone which lay scattered amongst the wreckage on the road. My laptop (with two months of edits to this book) torn to shreds, and my luggage looked like it fell from space into complete obliteration. Shortly after recovering, I shared a 15-second video of the carnage on my Instagram profile. I got lots of heartwarming comments and messages because of the post about my accident.

I was invited to this new German friend’s country house because my Instagram game is strong. So strong that this new friend thought I would be a great addition to an elbow-rubbing party with some of the most elite folks in Germany and the surrounding areas. How did this new friend become so sure that I was the perfect person to have at his exclusive party? Instagram. Over the years, my Instagram profile has developed into many thousands of snapshots of the life I want people to see. The pictures of me hobnobbing with the rich and famous probably helped. Do I always eat at the best restaurants in the world? No! Do I always hang out with supermodels? No way! Am I always so inspired? Sometimes. In reality, I lead a pretty dull life. The trick is, the photos I elected to share and the perception I was able to craft opened up doors I would have never found before Instagram. My Instagram has become the social proof my new friends need to induce radical inclusion.

On August 11th, I posted a picture alongside a brand new yellow 456 Ferrari wearing my iconic flower suit in front of my friend’s fancy Germany country house. Later that week, I would be featured on the site Rich Kids Of Instagram. Bring on the followers.

I met her on Instagram about three months ago. She would have been way out of my league if I met her in real life and started to chat her up. She even told me so. She is a supermodel from Eastern Europe. Now she lives in LA. She is 4 inches taller than me and five years older. She likes food and adventure — at least that is what I learned from her Instagram profile. I started following her because of her clever photo of her feet, I think. Or maybe I found her profile browsing a hashtag like #artbasel2012 or #burningman2012 or something like that. Anyway, I found her and followed her. Then, I liked and commented on a few of her photos that aligned with my general photographic themes — food, travel, and art. Those are the best kinds of pictures to like and comment on without coming across as creepy. The last thing you want to do is like a bunch of #selfies of a stranger. #creeper.

A few likes and comments, a couple hundred visual, timely, and consistent photos later and, Boom! I was on her radar. She followed me back. She started liking my photos. Instagram convinced her my life was remarkable. And then it happened. She wrote her phone number on one of my pictures from over a year ago asking me to text her. I did and the next thing you know we ran around for 11 days together driving from Los Angeles to San Francisco and back, staying in the abandoned warehouse of a friend, working on a vineyard during crush, and spending a romantic weekend at the Post Ranch Inn. You can see this all for yourself on my Instagram profile. And I guess that is how my dating life will work from now on.

13. Lifestyles of the Young, Rich, and Homeless

Originally Published Fall 2013

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, and we smiled at each other on occasion. My studio-gallery-restaurant-office-loft on Abbot Kinney was the place to be last spring. My summers at the Montauk house were the best. I loved living in an airstream on top of the cliffs above Malibu. But tonight, I am homeless. I am not worried because 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 and resigned from my studies. I joined a secret society at Stanford run by the most elite international students. With a group of my new powerful friends, I traveled to Asia during midterms. And that was when I met him.

It was 6 am 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, and then the music started to play. It was far too early for music.

A tall blond German guy wheeling speakers pumping deep house made his way down the dock at the marina club trailed by a dozen or so very tall beautiful ladies. After all, you need companionship like that when you are going for an overnight adventure around the South China Sea on a floating monster.

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 life.

Flash forward to August 2008. It was 3 am 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 said he had a surprise for me. His friend had a friend who knew a guy.

My grandfather said it best: “Friends are like fish; they go bad after three 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 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, four comfortable-looking blue 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.

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 objects. Think about how we live today:

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

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

It’s not about owning a car; 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 one fast car, three days, 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 an S550 Mercedes Brabus. We showed up at 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 way. We secretly obtained a sticker kit 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 flashy gold 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 smiley face emoji :)

We raced from San Francisco to Los Angeles, from Los Angeles to San Diego. It was truly exhilarating to move our molecules at such a rapid rate down the coast of California. And we got the experience for 99% 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 three days in my life, he significantly 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 eight 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, Gio and Charlie. Those crazy guys.

“They throw these amazing parties, man. They rent out abandon libraries. They have these one-night popups. They are throwing one in New York City this weekend. This one is for singles 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 so that 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.”

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 so much 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 excellent friends with this guy. But they’d only known each other for three months and only shared one weekend 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 differently. 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 the stuff you learn operating a start-up. This also is not the stuff you learn in school. This is the 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 embraced the lifestyle.

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 eclectic artists and musicians and fashionistas. People who had traveled the world. People with stories. Strange stories. Crazy stories. People who had lived life. People who, despite their sartorial elegance, were probably sleeping on somebody’s couch later that night.

I locked eyes with a gorgeous half-African half-Asian goddess at some point after my third drink. I became utterly infatuated with her. The next morning I woke up on the upper eastside in a high-rise with beautiful views of the park. But, even better, I was next to her.

Later that day, The Pirate and I flew back to San Francisco. The Pirate had an “appointment.” When I got home, I decided that I was in love 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 to study at Oxford. And we broke up.

The Pirate subsequently came to live with me in New York, in Los Angeles and has yet to have an apartment. He even started a company that supplies high-quality goods to the world’s 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 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 New York, San Francisco, and Los Angeles 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, lovers, and people I admire. And because of all that, I can be anywhere in the world, not knowing where I’m going to stay, but trust that I can find a home.

After my life imploded earlier this year, I shed a lot of my baggage. I got rid of my places, and I gave away most of my shit. I’ve been living out of my Jeep. I haven’t spent more than a few days in any one location. I’ve been apprenticing for people that are irrationally passionate about their uniquely unique work. Winemakers. Butchers. DJs. Muralists. I volunteer my time, gain experience, and share those experiences with the next friend who hosts me.

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

I think that is 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 for entertainment. If you can bring adventure to people’s lives, you become unique. 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.

14. Faking Banksy

Winter 2013

During the last week of October in 2013, I was lost at sea, floating off the coast of Los Angeles on a new friend’s 46' Beneteau. I was following in The Pirate’s footsteps. My new friend offered me the boat because he read my story “Lifestyles of the Young Rich and Homeless” and wanted to be part of my next adventure.

Traveling and trying to write a book became incredibly frustrating when I realized it was just my way of procrastinating post-Drunk Naked Founder. I know, I sound like an asshole but I was in a dark place.

When I published Lifestyles of the Young Rich and Homeless, it went viral. I found some joy in storytelling at scale. I wanted to see how far I could push it; to see if I could “hack” the system. So I wrote a letter to myself from the anonymous artist Banksy and published it.

The story goes like this: Banksy was doing a residency in NYC that nearly every press outlet in the western world covered for the hype and page views. I was thumbing through Instagram after Instagram post about the residency when I saw an opportunity — so I acted on it.

I wrote a letter on the boat and mailed it to myself when we arrived at the port in Santa Barbara. I made it seem like Banksy wanted me to host a dinner party in Los Angeles. The essay about the letter went insanely viral, and I started to gain a serious following because of my story.

The seemingly harmless experiment angered some people, but my intentions were not malicious. Do you notice that I did not claim the veracity of the letter? I bent my reader’s perception of reality. Gave them what they wanted to believe. I can’t help but think the bending of reality is standard amongst “professional” journalists and all too commonly believed by the uninformed public. We will come to know this tactic as “Fake News” in the coming years.

I guess, thought this experiment, I learned that I could manifest reality on the Internet. The lesson here is you can get people on the Internet to believe anything. And that can be good or very bad.

15. Famous Artists

Early 2014

There I was, dropping the kids off to swim in a Chateau Marmont throne after a pot of coffee and a hearty bacon breakfast burrito. And, guess whose unmistakeable laugh I heard as the door from the lobby swung open? James Fucking Franco! I could imagine his squinty face walking in as I pinched my ass cheeks together, trying not to make too much noise. Sweat on my brow, I focused on the black and white checkered tile trying to wrap up my business prematurely. And then, almost magically, the stall next to me swings open. The door slammed shut, he let out a moan, and plop. You get the picture. Even famous people take shits in public places.

It got me thinking. James Franco isn’t much different than me. We both have an audience of fans. We both manage to stay busy with all sorts of interesting hobbies. And we both poop. As it turns out, we both got “persuaded” into buying some costly art from an up and coming painter in Los Angeles.

On a chilly Friday night in Los Angeles, when it was just cold enough to wear a scarf over a V-neck T-shirt, I walked into a gallery opening in Hollywood. To my surprise, Paris Hilton was sauntering cheerily around the room. Paris smiled in my direction, walked over to me, and together we browsed the art while casually bantering about how much we enjoyed it.

Then Paris paused in front of one particular piece, admiring it deeply. It was called “Bob Dylan.” The artist walked over and stood next to us. Paris smiled and said, “I just loves it.”

And at that moment I decided to buy that particular piece. Right then, on the spot, without inquiring about the list price.

I handed the gallerist, who was casually waiting for this moment, my Black American Express, winked, and said, “Let’s do it.” Later, I found out the piece I’d bought was the most expensive artwork in the room. I also realized that there was something compelling happening before I decided to purchase the art.

The lesson I learned was about how the value of art directly correlates to the stories we tell, and the things we do to influence the buyer. This episode was proof enough to me that one can construct and socially engineer situations, and in some cases do so for a profit. Cue the light bulb above my head. I can do this too.

While shopping for vintage furniture at a flea market in Brooklyn a few weeks later, I noticed an artist who was painting these fantastic, vivid, modern-looking monsters over flea market pieces of art. I liked her aesthetic. She had about 20 pieces available for $100 each. I walked up to her, and said, as if channeling the Boss from my pre-mini retirement days, “If I can buy all of your art for only $2,000, that means you only have $2,000 worth of art.”

“Huh?” she said, confused.

“If you price your art at $1 million, then you might make $1 million.”

So, I became involved in “art.” I put art in quotes because my efforts were only half-serious. I started to invite influential friends over for dinner and give them “art” from my collection of flea market paintings. The art wasn’t great. But, my friends would go out and tell a great story for me. “I had dinner with Matty Mo the other night. He gave me a thousand dollar piece of art. Have you heard what he’s up to these days? Well, it’s an incredible story. Apparently . . .”

Once an influential friend of mine had been given a “thousand dollar” artwork and started spreading the story, the rest became history. Soon enough, the value of the artworks in my collection quickly exceeded $1,000. By way of this tactic, I was creating the value of my art collection and cultivating an art market. Success!

After one of my dinner parties a few weeks ago, I gave away one of my flea market paintings to a famous actress. She walked out of my loft with a big smile on her face. I told her that the value of that particular painting was in the thousands. The following week, I sold a few of the paintings to people who saw the same artwork on the famous actress’s Instagram feed. I guess you could say I’ve become interested in the business of art.

16. Lucky Day

Spring 2014

The luckiest day of my life was when I realized that I had an opportunity to do it right this time — a second chance. I’d come to the appropriate realization that — after traversing the earth on jets and yachts and filling my house with expensive furniture and my closet with pretty suits, shoes, and linens — I was drowning in a sea of meaningless shit. I think, for the first time in my adult life, I acquainted myself with a bit self-awareness. And it was a beautiful moment. I’m surely not all the way woke just yet, but I am happy to be making enthusiastic progress.

I started to think about what was important to me rather than what I wanted to buy or experience. And this is what I discovered: I valued continued education; I wanted to learn from people; and that perhaps the path to being a better human is to cut out all the fancy shit and go back to the basics — just being human with other humans, understanding where we come from, and connecting the dots between ideas and people.

Instead of seeking out short-lived experiences to pimp out my social media presence, I started viewing my newfound perspective as an opportunity to build relationships; to start something meaningful with a community.

Connecting with people provides real happiness, not just an endorphin kick when I get a like or comment on social media. The people in your life are all that matter in this world. To quote Rod Stewart,

“I wish that I knew what I know now when I was younger.”

17. A More Thoughtful Approach

Spring 2014

My only hope is that you’ve been entertained by reading this short story; and maybe that my huge wins and my disastrous fuck-ups will have a positive impact on the decisions you make in your real and digital lives.

Unless you’ve reached a Johhny Depp–level of notoriety, social media will always be an integral part of your life and your success. It would be hypocritical of me to call for THE END of social media. So I’m not doing that. But I am calling for a more thoughtful approach. Because, in reality, your life is being recorded and interpreted more and more each day. Think Big Brother. Think War. Think Porn.

I knew, secretly at least, that I had a problem when I started to guide my life in the direction of more luxuriant content. Mostly, I began creating content that was specifically tailored to arouse attention from a particular type of friend I aspired to be. Chasing “likes”? Yes, I was chasing “likes.”

The people I’d choose to hang out with or the restaurants I’d prefer to dine at or the after-hour activities I’d want to engage in were merely opportunities for more social media content — which meant reinforcing my identity with more likes, hearts, notes, retweets, etc.

Instead of I want to eat dinner at this restaurant tonight because I enjoy the food, it was I want to eat dinner at this restaurant because posting a photo of my presence there will be good for my online image.

Instead of I want to hang out with this person today because he or she enriches my life or teaches me something or is pleasant to be around, it was I want to hang out with this person today because my association with him or her (with photographic evidence) will add weight to my worth in the online world.

Along with my greed for more online attention and my insatiable cravings for that wonderful release of endorphins I got from each additional notification of activity on one of my social networks, I developed a very skewed mentality. I became aware of my narcissistic, selfish, self-important tendencies.

The social white lies I begin to tell — at first, semi-harmlessly, for entertainment — seeped into my real life. I became Matty Mo. I couldn’t separate truth from reality. I didn’t know who I was anymore. And then, without any real identity, I started to make content that would enrich the online version of myself — perpetuating my self-destruction.

I’m not sure where I’ll be tomorrow. I got in my Jeep and headed north — cutting across California and Nevada, then shooting up through Utah and Idaho, until I reached a cabin nestled against the mountains in Jackson, Wyoming. I’ve been here for a couple of weeks now, working on the conclusion of this book. I still don’t have it, maybe because my story is not complete.

I believe that social media can beautifully connect the world. Think about all the charities spreading their message and changing the lives of millions. Think about how civilians who mobilized themselves via Twitter can overthrow corrupt regimes. Modern-day war tactics? Yep. Think about the millions of people who feel empowered by their voice. Even former-amateur-porn-stars-turned-celebrities like Paris Hilton and Kim Kardashian might argue that social media gave them the life they’d always wanted.

Social media participation is going to define your life. And it should enable you to get more things accomplished. It’s not black and white, right or wrong. It is just a tool. Use it. Don’t overuse it, and don’t underuse it. Share smart. And sometimes it’s okay to do the wrong thing for the right reasons.

And above all else — remember, your world is only as big as you imagine it to be. Do a little investigating, and peel back the layers of the world that is currently your life.

Think about my situation. Sure, I lost my way. And I am not entirely sure what is next for me. But I will keep moving forward knowing what I know about the way I think this world works. And I will be sure never again to pursue a venture unless it makes me happy and connected to my community.

It’s my dream to become The Most Famous Artist, whatever that means. Time will tell. What the fuck am I doing in Wyoming? I can’t help staring at my phone across the room. I haven’t posted a photo to Instagram in a few weeks.

But now I’m tempted to share. Fuck it. This sunset is just too damn beautiful not to share it with the world. I’ll take one photo and post it. No filter, though. Well, maybe a subtle filter. People are probably worried about me, anyway.

If I post a photo, people will know I’m OK.

***********************THE END (for now)*************************

Authors note: these essays were written sporadically between 2013–14. This text is meant to set the stage for a forthcoming book about “Becoming The Most Famous Artist.”

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If you see a typo or have a question, please comment, and I’ll be in touch.

Thank you,

Matty Mo aka The Most Famous Artist

Matty Mo

Written by

Matty Mo

Action with Intention // www.themostfamousartist.com

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