My Entrepreneurial History
Entrepreneurship has been a consistent pursuit throughout my life. Here's the whole journey.
Family History
I am fortunate to have grown up in an entrepreneurial family. My family tree includes:
My grandfather (Dad’s dad) and his brothers ran multiple enterprises including a fruit business, a liquor store and cigarette vending machines. They ran the gamut of health and wellness to vice businesses. I believe the vices profited more…
My other grandfather (Mother’s dad) was an engineer at Kodak where he ended up working for the CIA. He developed components of the sattelite technology that kept us out of WW3 during the Cold War. While he didn’t start his own company, after he retired he volunteered his time to help small businesses with their finances as he thought there was no better cause in America than starting a business.
My father has started and exited multiple businesses. I had the privilege of growing up watching him absolutely grind building businesses 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 growing up.
My Entrepreneurial Career
I’ve been a part of multiple entrepreneurial endeavors.
Pogs - for those of you who don’t know what pogs are, here is a history. When I was in 5th grade back around 1996 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 - back when I was in high school (2000-2003) Duxbury High had a policy that is a student was late they weren’t allowed to participate in extra curricular activities. This dramatically impacted the performance of our sports teams if students weren’t able to play due to tardiness. I didn’t believe that preventing students that had issues with tardiness from participating in valuable non-academic activities would achieve the desired outcome of creating responsible and well rounded Americans that US public education is said to desire.
As a high schooler that was 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 then printed a bunch of the doctor’s notes and sold them to students - $20 / senior, $30 / junior, $40 / sophomore and $100 / freshman (I was a sophomore). Student’s would then forge signatures and get out of missing practices and games. My ideal customer was a student athlete, usually male, but I would sell to everyone: thespians, band members, and others of course, though demand was lower.
Ultimately, the market got too hot. Administrators started asking questions about why kids were at the doctor multiples times per week. So while the model was excellent (100% margin since I printed them at the school library), ultimately I sold the templates to another student and bailed from 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 - after high school I attended Hamilton College which is located in Clinton NY. Hamilton is a small school of about 2k students and there isn’t a whole lot happening in the town of Clinton. There was one main general store which was at a gas station about a mile from campus. Back in 2003-2004 the gas station sold ping pong balls for about $4-$5 per ball in packs of 4-6. I found the price point ridiculous for a product that barely lasted more than a weekend (obviously balls were used for traditional ping pong and, of course, not for drinking games like beirut/beer pong). The store also closed around 10pm which was relatively early for a college student’s party schedule.
So I decided to find out where most ping pong balls were manufactured. Not surprisingly I found that you could buy bulk orders of ping pong balls directly from manufacturers in China for anywhere from $.05-$.25 per ball depending on the volume of the order. So I saved up a bit of dough and ordered 10k balls which brought the unit cost to about $.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 the packaging of 10k ping pong balls is about comes in two boxes that are ~8 feet tall, 4 feet wide and 4 feet deep. I was living in a single dorm room at the time about the size of shoe box and the balls ended up taking up most of the space in my room. So like any good friend, I decided to turn my room into a storage space for my new enterprise and I moved my bed and things 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 an overall 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 operations - $.25-$.50 per ball - and then when they would close, I rolled out surge pricing. Depending on what I was doing, price of balls could be $1 or $20. There wasn’t a lot of method to the madness admittedly. As my enterprise grew, so did the vision for the business. 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 frats/sorority logos on the balls. Syracuse, Ithaca, Cornell, Colgate, Boston College, Uconn, etc. I would then drive with friends to different schools, show up at different frats/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 someone in the Hamilton administration that they had received a cease and desist notice from lawyers at the NCAA and different universities regarding the illegal use of different universities’ 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 they didn’t have a hard time figuring out who the letters were for. As a 19 year-old kid, I stupidly ended up ceasing business operations versus simply figuring out licensing of the logos and running a legitimate operation. It had grow in to a 6-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 admin admired my entrepreneurial zeal ad suggested I start an entrepreneurship club. So I teamed up with my buddy Guillermo “Willy” Artiles and created the club. The first thing we did was notify some famous Hamilton alumni that the school had a policy that prevented students from running businesses out of their dorm rooms. We thought this was pretty stupid (and 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. So to do this we made t-shirts to sell 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 alums to speak on campus. We hosted a few and ultimately handed the club off to other students that were more interested in being in a club versus actually starting businesses…CampusWord - During the time of the Hamilton E-ship Club, my mother had gotten me a startup magazine that had several stories about how people were making money on the internet. As someone who had taken AP CS in high school, I was very interested in technology and also making money. I spent all of winter break my junior year diving into different online business models and somehow I landed on ecommerce affiliate marketing schemes. I created a website called CampusWord that was originally an ecom affiliate site where I tried to drive traffic to products fro college students. It wasn’t great.
After New Years, I had my buddy Greg Rogan staying at my host as he is an Irish citizen whose family lived in Saudi Arabia. I convinced Rogan to join me starting an online business and we began researching a bunch of different online business models. We were really intrigues by CollegeHumor which was an incredibly successful content site focused on, you guessed it, funny shit. Greg and I thought there was a space for college students to publish content in a more open sourced matter about issues that matter to them. We emailed every college newspaper in the country and told them that the CampusWord was “the New York Times of college publications” and invited their staff to apply for unpaid internships in order to build their portfolios and get national exposure. The response was surprisingly strong and we got a bunch of writers out of the gate. Next, we spun up a website using an open source CMS called Joomla. The technology wasn’t great and we had a dev firm develop our first custom theme that 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 our junior year, Greg moved into my house back in MA and we worked all summer on the site and growing our content base. We also convinced our other pal Kevin McCarthy to join the squad. While Kevin was a chem major, he was one of the smartest dudes we knew and he quickly learned server side programming and helped us with the site. We ended up running the site all through our senior year and continued to grow in content contributors and audience. After graduating, we all moved into a shit hole of an apartment in the west part of Boston called Brighton. We worked around the clock on the site, making money from ad networks like Adbrite which was what CollegeHumor used. At our height, we had some of our content contributors get picked up on CNN and Fox News. Due the fact we had students from hundreds of universities writing content pretty freely, we ended up getting on the radar of these major news outlets for some of the more edgy content on topics ranging from concealed gun carry laws on campus to rape issues on some campuses. We were not ready or qualified to handle the inquiries from major media outlets
