Breaking into Web 2.0.

The Perception of Insanity and Validation in Silicon Valley

by Matthieu McClintock

In Part V of my entrepreneurial endeavor series, I will discuss my true entry into Web 2.0. Part IV of the series discussed my time in the mobile advertising industry. This installment takes place six months after the end of the previous installment.

It wasn’t intentional. It wasn’t even planned. It was, however, one of those lightbulb moments you hear about so often. It had been six months since the fall of SMA and my rejoining the REIT and starting my final year of college at the University of Central Florida. My time in college had been extended due to a late transfer from being a Finance major to majoring in Business, Communications, and Film. This tacked on another year of college. There was always something about me where I felt it was never enough — something I still feel to this day.

One day I was sitting at the office, it was a very slow day. I had recently began reading TechCrunch and learning more and more about Web 2.0. but I hadn’t dipped my toes in the water yet. I was watching, observing, learning, but wasn’t sure where that would take me. I listened to lectures by tech superstars on Stanford’s eCorner and began reading books like “Crossing the Chasm” and biographies of the major innovators in technology, the most notable was Steve Jobs whom I knew very little about prior to reading the only approved novel about him by Walter Isaacson. Reading this novel was the impetus to my deciding that tech was my destiny, I shared so many weaknesses and psychological issues Mr. Jobs did, and a few strengths as well and I saw that my idea of who you had to be to make it in tech was way off.

That morning in the office I had two ideas on the table. First, I had an idea to start an online news publication as I was constantly reading about the death of old media and, having previously worked at a newspaper in Tallahassee and being a writer, I wanted to start a news publication online that wouldn’t be limited by the money and political influences that corrupted traditional news media. Secondly, I wanted to revisit an idea from my previous endeavor, a mobile advertising aggregator. Ironically, I didn’t pick either. I picked an idea I had at SMA that I pitched to a group of interns to see if they would use it. The idea was in its infancy but it had never left the forefront of my mind. So what was the big idea?

In my time at SMA I noticed that there was tons of data floating around the web about us. Our social networks, our finances, our job history, education, everything about us in one way or another had found its way online. And in my experience constantly trying to achieve the impossible, I thought “What if I could leverage all of this online data to help increase the masses statistical probability of achieving their major life goals?” It could be getting into a school, getting a job or promotion, starting a company, saving for a car or house — whatever you wanted — the aggregation of your online data was — in my mind — the best way to issue recommendations to give you the best chance of success.

I worked 50 hours a week and spent every night at UCF and got out of class at around 9:30pm. The library closed at 1am. I decided to pull the trigger on my idea and began by going to the UCF Library after class every night where I would work until the library closed at 1am at which point I’d drove home where I’d arrive around 1:30am, read or listen to an eCorner lecture until 2:00am and wake up at 8:00am for work. I began with a series of large sheets of engineering paper and began to work out the architecture of how a software application could achieve what I wanted to do. I quickly learned that recommender systems, data mining, and APIs were the ingredients to building my idea. All three required that I not only study each discipline rigorously, but also learn server-side programming. I picked PHP.

I learned that Australia and New Zealand were the leading countries on thought-leadership when it came to Data Mining and read over a dozen books on the subject. I learned that recommender systems could be studied by looking at publicly available patents as they were prevalent in many different popular websites and mobile applications like Amazon, Netflix, PageRank by Google, amongst others. I even found a handful of books that were dedicated to recommender systems and nearest neighbor algorithms. I studied the APIs of Facebook, Twitter, LinkedIn, and Yodlee and began studying the open-source Natural Language Processing framework GATE. By studying all of these different disciplines the pieces of the puzzle began to assemble and I started putting together a patent application which was an aggregation in and of itself, pulling methods from data mining, recommender systems, APIs, GATE, and other technologies. My nights at the UCF Library were exciting — I felt like I was alone in the garage building my own Apple Computer.

There was no one there telling me I had a genius idea, no one urging me to keep going, no one supervising me and making sure I was staying the course. There were times of extreme excitement and confidence and times of doubt but I stayed the course until the pieces of the puzzle all came together and my patent application was finally done after three months of intensive research and extremely long hours. It was time to start presenting my idea to the world and I started with the University. I contacted every professor at the Computer Science department and quickly learned that college professors were college professors for a reason — they were deathly afraid of risk and innovation and all I got from them was “Sounds like a great idea. You should go raise some money.” No shit.

I then began looking for a technical co-founder and was brought on board by the UCF Venture Lab and Incubator Program that paired me with a successful entrepreneur and former Googler who was the closest to a co-founder I would ever come to. I found that he was to self-centered and didn’t have the vision or business sense to be a good partner, he was too technical, he couldn’t understand normal people, the end users — and that was a deal breaker. I decided I wouldn’t make the mistake I made at SMA, this time I would go it alone. I started by outlining the MVP, or Minimum Viable Product. At the same time I began teaching myself PHP, Twitter Bootstrap, and the APIs of Facebook, Twitter, LinkedIn, and Yodlee. Six months after I began my work on this project I had a fully functioning MVP which I screen recorded into a demo and sent to Silicon Valley along with my pending patent application.

Interest didn’t come over night. I knew that to successfully find funding for my company, which wasn’t incorporated and was without a name, I would need to resign from my job which I did in April of 2011 at the age of 23. It wasn’t until July that I received a call from an angel investment firm in the valley that wanted to meet me and flew me out to San Francisco where I met with some VC partners and entrepreneurs-in-residence who were shocked I had done all of this without funding, without a partner, without supervision — all the while working and studying full time. They also loved that the product wasn’t about money, it was about helping people reach their full human potential. That said a lot about me. They also took note of my experience as an entrepreneur and very quickly I was offered seed funding that was 1,000 times any amount of money I had ever raised.

I didn’t say yes right away. I spoke with my mother, I spoke with my best friend, my step father, and to be honest — no one had really insightful advice. I had a lot of thinking to do and spent a few weeks on the Jersey Shore where my mother and step-father spent their summers and mulled things over. I flew back out to San Francisco, this time from another VC firm where I met a prominent tech entrepreneur who had heard my story and went behind his VC firms back to attempt to privately fund my project. I was hesitant, I had already started three businesses, I wasn’t new to business or negotiating or even raising money. I also wasn’t quick to trust people, no matter how rich or famous they were. And while on the precipice of jumping into Silicon Valley something happened that I could have never predicted. My best friend of 10 years killed himself. I stopped answering phone calls, returning emails, and locked myself in my apartment.

The project I had spent the past nine months working on day and night suddenly was the last thing on my mind and I completely lost it. I turned into Howard Hughes. I became a recluse, refused to leave my apartment and paid others to get my groceries and dropped out of college. I watched movies on repeat to keep my mind off of the perpetual pain of having lost what was essentially a brother to me, the closest person in my life since as far as I could remember. I wish I could end this post on a positive note but my period of seclusion went unnoticed by the world, I didn’t have a large family and my only friend just passed. The phone calls and emails from the Valley stopped coming in and I thought nothing of it. I had given up on life, on everything, and it would be a long time before someone woke me up and I got back to work. More on than in Part VI of my entrepreneurial endeavor series. Lesson to be learned, it’s not all about the fame and riches, sometimes life takes a turn you couldn’t anticipate and completely throws you off track. In the next installment, I’ll discuss how I got back on track and finished what I started.