Why going from College->Career = Risky

Have you considered starting your own company?

by Matthieu McClintock, Serial Entrepreneur & Product Manager at Solodev

I did not go from College to Career. That being said, everyone else I know and have known, for the most part, did exactly that — they mostly ended up working at insurance companies or retail banks. I’ve always been like an exhibit at a museum of weirdos to ‘normal’ people who followed the beaten path. Everyone is always so surprised like it’s unthinkable that a young kid would roll the dice over and over again, dropping in and out of college accordingly and spinning up companies like pizzas. However, when I finally decided upon a career, I had one thing none of my competing candidates had, a ridiculous amount of all kinds of real-world experience and both the formal and informal education to boot.

I started college right after high school and did a year before dropping out and forming my first company at 19 years old in 2007, raising $30,000 from a wealthy friend, and moving from South Florida to Hollywood where I worked in music, TV, and film production. At 21 years old, in 2010, I moved to Orlando and re-enrolled in college, where I stayed for a year and got a job as a leasing agent and immersed myself in learning everything about marketing. I read the works of David Ogilvy and other advertising pioneers and went from a leasing agent to a Senior Marketing Director of 55 apartment complexes across the country at the age of 21. Not bragging, I didn’t go out at night and party, I was a full time student, I worked full time, and every second I wasn’t working, studying, or in class I was learning the art of advertising.

While serving as Chief Marketing Director politics turned my interest away and my focus shifted to finance, particularly securities. I then delved into the world of Finance and changed my major, completing all courses required for a Finance degree and spending most of my free time studying the books of Peter Lynch, Benjamin Graham, and running a ‘hypothetical’ portfolio on Investopedia.com (great way to learn the market FYI). Over a weekend at the office I printed and read 30 years worth of letters from Warren Buffet to his shareholders at Berkshire Hathaway where I gained an immense amount of knowledge of value investing.

My desire was to complete a degree in Finance, continue my informal financial education, and work as a securities analyst at Morgan Stanley (where I knew some family friends) before starting my own fund. During my time in finance, I managed the portfolios of several friends and family, all of which I made a fortune for by buying heavy into blue chip stocks during the collapse of 2008 and selling off in 2010–2011 when the market bounced back, hence my confidence to start my own fund. One day my stepfather sent me an article from Rolling Stone Magazine about Goldman Sachs and within an hour I changed majors and left finance behind.

I then refocused on finishing college and moving up at the REIT I had been working at before internal politics removed me from the top of the list to the bottom (lesson learned: Don’t outshine your master). I knew my career in real estate was over and after being informed I was not getting a well-deserved raise based on company KPIs and records I had set, I made an impulsive decision to start a company based on a marketing technology I introduced and managed for the REIT: SMS Marketing. I went to lunch with a friend from college who was working at Lockheed Martin with the mindset I would not leave lunch without a check and by the end of the meal, I raised $15,000. I quit my job, sold my car, raising an additional $10,000, dropped out of college and formed a software company at 22 years old in 2010.

This was my first company to net a profit and I learned a tremendous amount about digital marketing, B2B sales, software (particularly SaaS), web development, and just running a business in general. After a year, and some creative differences with my 50% partner who ran our sales apparatus, I sold my share of the company and returned to a Senior Marketing Position with my knew “skills and experience” and enrolled in a ‘real college’, not a community college, the prestigious University of Central Florida, also known as ‘U Can’t Finish.’ I stayed at this company and college until one Sunday, while sitting at my office, I decided to start another tech company. The year was 2012. This was the big one, the mother load, this wasn’t about money or independence, it was a game changer, a product I was obsessed and passionate about building. Nothing would stop me.

I rented a bunch of books from the UCF Library and began learning about Data Mining, Machine Learning, Recommender Systems, PageRank, and various Web Development Technologies. I spent an entire summer learning everything I could on those respective subjects. I sought out a “technical co-founder” but found most developers were like the screenwriters I met in Hollywood, no one wanted to co-anything, what they had was the “next best thing.” They never did. Not once. I decided to learn coding myself and after a morning class at UCF I went to the library and took a PHP Tutorial for ten hours straight and by the end of the day I knew how to do quite a bit with PHP. I then rented some books on Object Oriented PHP, MVC Frameworks, and what was known as Twitter Bootstrap at the time.

I began with developing the product completely on the server side with recommendations being printed out in plain boring HTML onto a white page using self-referencing ‘if else’ conditional statements wrapped inside child and master functions in PHP and data pulled from forms and the Facebook API. Once I was able to learn the Facebook API and integrate it with my application I had brought the product to its MVP state and turned to front-end development. How could I make my awesome product not just be a robust recommender system printing out <p> tags on a white HTML page?

The answer to that was Twitter Bootstrap, a responsive front-end framework I learned the ins and outs of and turned what was the ugliest web app ever into a better looking web application. I then wrote a patent application that detailed every algorithm and technology used in the project and submitted it for patent approval and went on a marketing rampage calling and emailing every person in Silicon Valley.

I went through times of doubt, times of insanity, I was constantly exhausted working from 8am to 6pm, college classes from 7pm to 10pm and then coding and getting my demo out to the world from 10pm to 1am when the UCF Library closed. On the drive to and from UCF, I listened to lectures from Stanford’s eCorner lecture series and went to bed with a book about tech or listening to another lecture from a startup founder or VC partner. No one knew what I was doing, I was completely alone. Then one day, while sitting on a beach in Margate, New Jersey reading a book about recommender systems, I got a phone call from a VC Firm that wanted me to demo the product. Three days later I was in San Francisco and after several offers, I sold my company and began my career as a serial entrepreneur in 2012.

I founded lurnn.com the same year at 23 years old out of my frustration with UCF’s WebCourses Portal and completed the project and began licensing it in late 2014 to public universities, ironically UCF was not one of them. I then founded BiggerTexting.com in early 2014, a SaaS solution for SMS marketing which almost immediately began generating revenue and paid my bills for the next couple of years. I then began working on smartkrawl, a digital advertising aggregator, before I was offered several jobs and was doing half a dozen interviews over the phone every week with Sony, Warner Brothers, Lifetime, Oracle and Equity Residential. I didn’t want to go back to a corporate job and then one day I got an email from a local software company called Solodev.

After extensive research, I figured I’d drop by and hear what they had to say and I was instantly sold on the product I was to manage, OCOA, don’t google it, I probably shouldn’t even mention it, it’s a secret project and I will comment no further. I looked at it as an entrepreneur-in-residence type of thing so it wasn’t a job, it felt like one of my own endeavors it just had more funding, an office, and superiors to answer to. I’ve been there nearly a year and a half and I don’t regret it at all although I’m constantly asked why I didn’t take job X, Y or Z. Money isn’t what it’s all about for me although I understand what it’s like to only care about money.

Now comes the part where I tell you why you should spend your twenties in a perpetual state of risk taking instead of taking the ‘safe route.’ Because I didn’t take the ‘safe route’ I have 100% job security, if I want it, for the rest of my life. I have a ridiculous amount of experience (not to mention a college education) in dozens of fields and am constantly being recruited on LinkedIn even though they are well aware I have a job.

Others, however, who went the ‘safe route’ from college to career are actually taking a bigger risk than I ever did. If they’re fired, they have no experience, and that’s if they’re lucky enough to get a job in the first place. Also, being fired isn’t really great job experience and in my observations in corporate America, kids who went straight from college to a job tend to have entitlement and attitude issues. College has programmed them to think they deserve things that they do not. Luckily, I work with people who have overcome or surpassed that mentality, namely due to being raised well (I suspect).

So the moral of the story is this — there is one time to take risks and that’s when you’re young and have no real responsibilities. No family. No mortgage. Not too many bills or anyone to support. FYI — I’m still only 27 so I still have no real responsibilities other then my job, house, and car. I’m not saying everyone should start their own company, 99% of you reading this aren’t cut out for it. It comes down to three main questions you need to ask yourself that create the entrepreneurial equation.

  1. Is there something you care about that you can learn how to build?
  2. Can you work long hours without being supervised?
  3. Do you require formal education to learn new skills?

If you have something you care about, are truly passionate about, that you want to build, you’ve reached step one. Money can’t be your only motivator. Then comes the ability to work long hours without anyone telling you what to do or how much potential what you’re working on has, this is where roughly 70% of people fall off. And last but not least, are you capable of teaching yourself new skills or must you have a formal education environment? This is important as you’ll always need to be able to learn new skills and not requiring a teacher makes it 1,000 times easier. For example, I’m spending my Saturday learning Symfony and taking a refreshing course on Backbone.js — my point — learning never ends. If your answer to all three questions meet these requirements, then maybe you’re cut out to be an entrepreneur.

Feel free to check out a very old portfolio website of what I did from 19 years old to graduating college in 2013 at mattmcclintock.com or comment on the thread below, I’d love to answer any questions you may have about the frightening leap of becoming an entrepreneur.

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