My Entrepreneurial History
Entrepreneurship has been a consistent pursuit throughout my life. Here's the whole journey.
Family Entrepreneurial History
I am fortunate to have grown up in an entrepreneurial family.
My grandfather on my dad’s side and his brothers ran multiple enterprises in Framingham, MA — a fruit importing business, a liquor store, and cigarette vending machines. They ran the gamut from health and wellness to vice businesses. I believe the vices profited more.
My grandfather on my mother’s side was an engineer at Kodak where he ended up working for the CIA. He developed components of the satellite technology that kept us out of World War III during the Cold War. While he didn’t start his own company, after he retired he volunteered his time helping small businesses with their finances. He thought there was no better cause in America than starting a business. (You can read more about him and the rest of my family on my Family History page.)
My father has started and exited multiple businesses. I had the privilege of growing up watching him absolutely grind — building companies after putting himself through college and getting my mother to put him through business school. He’s run a furniture company and multiple healthcare services businesses. I couldn’t ask for a better person to have learned from.
My Entrepreneurial Career
I’ve been a part of multiple entrepreneurial endeavors.
Pogs (c. 1996)
For those of you who don’t know what pogs are, here is a history. When I was in 5th grade, I sold pogs to kids on the playground during the height of the pog craze. This was my first entrepreneurial endeavor.
Student Extra-Curricular Attendance Insurance (2000–2003)
Back when I was in high school, Duxbury High had a policy that if a student was late, they weren’t allowed to participate in extra-curricular activities. This dramatically impacted the performance of our sports teams when students couldn’t play due to tardiness. I didn’t believe that preventing tardy students from participating in valuable non-academic activities would achieve the desired outcome of creating responsible and well-rounded Americans that U.S. public education claims to desire.
As a high schooler taking computer science classes, I got time during class to mess around on the internet and was able to figure out how to get into some file servers of local doctors’ offices and grab templates for the notes they used for kids who needed proof of an appointment when missing school. I printed a bunch of the notes and sold them to students — $20 for seniors, $30 for juniors, $40 for sophomores, and $100 for freshmen. I was a sophomore. Students would forge signatures and get out of missing practices and games. My ideal customer was a student athlete, usually male, but I sold to everyone — thespians, band members, and others — though demand was lower.
Ultimately, the market got too hot. Administrators started asking questions about why kids were at the doctor multiple times per week. While the model was excellent (100% margin since I printed them at the school library), I eventually sold the templates to another student and exited the business.
Moral gray area? No, not really. I probably shouldn’t have done it. But if I’m being honest, the learning experience was great and it was relatively harmless.
Ping Pong Ball Importer (2003–2004)
After high school I attended Hamilton College in Clinton, NY. Hamilton is a small school of about 2,000 students and there isn’t a whole lot happening in the town of Clinton. There was one main general store at a gas station about a mile from campus. The gas station sold ping pong balls for about $4–$5 per pack of 4–6 balls. I found the price point ridiculous for a product that barely lasted more than a weekend. (Obviously the balls were used for traditional ping pong and absolutely not for drinking games like beirut.) The store also closed around 10pm, which was relatively early for a college student’s schedule.
So I decided to find out where most ping pong balls were manufactured. Not surprisingly, you could buy bulk orders directly from manufacturers in China for anywhere from $0.05–$0.25 per ball depending on volume. I saved up some money and ordered 10,000 balls, which brought the unit cost to about $0.12 per ball.
One day on my way home from class — must have been the one time I went — I got a call from the student mail center telling me to get down there and “get this thing the hell out of here.” It turns out 10,000 ping pong balls come in two boxes that are roughly 8 feet tall, 4 feet wide, and 4 feet deep. I was living in a single dorm room about the size of a shoe box, and the boxes ended up taking most of the space. So like any good friend, I moved my bed and belongings into my buddy Lenny’s room down the hall without asking him while he was at class.
Lenny was a diligent student who is now a doctor. He is also a tolerant and good guy and ended up letting me bunk up with him. Did girls find it a little weird? Sure. But did Lenny have access to free ping pong balls? Well, no. I wasn’t running a charity. But he didn’t really need them anyway because he was working hard at becoming a doctor. (What up Lenny!)
At first I just sold balls to Hamilton students. I would undercut the local store during their hours of operation — $0.25–$0.50 per ball — and then when they closed, I rolled out surge pricing. Depending on what I was doing, price per ball could be $1 or $20. There wasn’t a lot of method to the madness, admittedly.
As the enterprise grew, so did the vision. I found a printing company in Ohio that would put logos on the balls without much concern for copyright laws. I started putting logos of other colleges and fraternities/sororities on them — Syracuse, Ithaca, Cornell, Colgate, Boston College, UConn, etc. I would drive with friends to different schools, show up at frat houses and sororities, sell them balls in bulk, and party with them after. Business was booming.
A few months into the operation, I got a notice from the Hamilton administration that they had received cease and desist letters from lawyers at the NCAA and multiple universities regarding the illegal use of their IP. Somehow they figured out it was someone from Hamilton, but because the enterprise wasn’t exactly a legal corporate entity, they couldn’t identify me personally. I had tried a few times to get the Hamilton College store to carry the balls, so the administration didn’t have a hard time figuring out who the letters were for.
As a 19-year-old kid, I stupidly ceased business operations instead of figuring out how to license the logos and run a legitimate operation. It had grown into a six-figure revenue business, so this was a dumb move.
Hamilton Entrepreneurship Club
After my foray into the world of IP piracy, I decided to go legit and work with the establishment. Some people in the Hamilton administration admired the entrepreneurial energy and suggested I start an entrepreneurship club. So I teamed up with my buddy Guillermo “Willy” Artiles and created one.
The first thing we did was notify some prominent Hamilton alumni that the school had a policy preventing students from running businesses out of their dorm rooms. We thought this was pretty stupid (and it felt personal), so we emailed the biggest alumni names who were entrepreneurs and asked them to withhold donations to the school until the rule was changed. Shockingly, one prominent alum did just that, and the rule was changed.
Our second initiative was to finance the club. We made t-shirts that said “Hamilton Entrepreneurs: Let’s Start Some Shit.” The shirts sold well but were ultimately shut down on campus. A few administrators then approached me and asked if we could focus our efforts on bringing alumni to speak on campus. We hosted a few and ultimately handed the club off to other students who were more interested in being in a club than actually starting businesses.
CampusWord
During the time of the E-ship Club, my mother had given me a startup magazine with stories about how people were making money on the internet. As someone who had taken AP Computer Science in high school, I was interested in technology and also making money. I spent all of winter break my junior year diving into different online business models and somehow landed on ecommerce affiliate marketing. I created a website called CampusWord that was originally an affiliate site where I tried to drive traffic to products for college students. It wasn’t great.
After New Year’s, my buddy Greg Rogan was staying at my house. Greg is an Irish citizen whose family lived in Saudi Arabia. I convinced him to join me starting an online business and we began researching different models. We were really intrigued by CollegeHumor, which was an incredibly successful content site focused on — you guessed it — funny shit. Greg and I thought there was space for college students to publish content in a more open-source manner about issues that mattered to them.
We emailed every college newspaper in the country and told them that CampusWord was “the New York Times of college publications,” and invited their staff to apply for unpaid internships to build their portfolios and get national exposure. The response was surprisingly strong and we got a bunch of writers right out of the gate.
We spun up a website using an open source CMS called Joomla. The technology wasn’t great, and we hired a dev firm to build our first custom theme — which had sound effects. Every time you sat on a page for too long, a loud “bing” would pierce your ears. It was brutal.
The summer after junior year, Greg moved into my house back in Massachusetts and we worked all summer on the site and growing our content base. We also convinced our pal Kevin McCarthy to join the squad. Kevin was a chem major, but he was one of the smartest guys we knew and quickly taught himself server-side programming to help us with the site.
We ran CampusWord through senior year and continued to grow in contributors and audience. After graduating, we all moved into a shithole of an apartment in Brighton (the western part of Boston). We worked around the clock on the site, making money from ad networks like Adbrite — the same network CollegeHumor used.
At our peak, some of our content contributors got picked up by CNN and Fox News. Because we had students from hundreds of universities writing content pretty freely, we ended up on the radar of major news outlets for some of the edgier content — pieces on topics ranging from concealed carry laws on campus to assault issues at different universities. We were not ready or qualified to handle the inquiries from major media outlets.