In 2007, I founded my first company, a bus transportation company called Weekend Gator. At the time my girlfriend was still in school and I had just moved back home to Miami, about 5 hours away. We tried to see each other on weekends, but there weren’t very good options and it was destroying our relationship. So I built a company to help make it easier for us, assuming there must be a bunch of people in similar situations.

Weekend Gator ran weekend bus transports across 6 cities in Florida including Miami, Fort Lauderdale, Orlando, and Gainesville.  Essentially, I’d operate like a high end greyhound, renting luxury coaches on the weekend, selling tickets on my website, and making a healthy profit if I filled up the bus. Luckily, a lot of people had loved ones far away and students quickly started using my service.

I thought of a lot of crazy marketing ideas back then. Originally I just flyered up the school, but then I started getting creative and flyering people when they’d get off from other bus services. My competition hated me! At some point I figured out a way to buy a database of the incoming freshman class and through another hack working with the Gainesville tourism board I mailed 20,000 incoming students and their families flyers of our service, for free. Word spread fast, and business was booming!

We were profitable in under 2 months and had 1,000’s of students traveling with us. I should have been stoked. But running a transportation company wasn’t all that it’s cracked up to be. There were a lot of factors that I couldn’t control like bad weather, buses breaking down, problems with the drivers, and rising gas prices (this is when they peaked at $150/barrel in 2007). I also had massive technical problem with our website, which was over-selling tickets, but not logging in the ticket sales. Then there were situations where someone was late for the bus, but needed to get on it to get to their test. So we’d wait 20-30 minutes for them to come, while everyone else on the bus complained. Customers complaints rose and I realized, I had built something that made money, but I really didn’t love it.

I wanted to provide a service that made everyone happy, but transportation isn’t really a good business for that. In less than a year, I decided to sell the business and move on to a career in advertising, which I was still very passionate about back then. I’d end up leaving that career track also to start a new business, but that’s a different story for a different day. Weekend Gator was a great first company, it taught me to believe in my ability to run a business and that doing what you love is more important than doing what makes you money.