Are you asking “Why?”

This last week, I had the pleasure of visiting a close friend, Jess, in Gainesville, FL. Jess is a student at the University of Florida (UF), and she has a healthy curiosity about many things. She’s creative, writes prolifically, and she asks questions as fast as a 5-year old who has just discovered the word “why.” Her inquisitive nature about everything was a refreshing change of pace from my day-to-day progress focused on research, and I eventually realized that inquisition would be the overarching theme of my adventure:

Prior to my trip, I had tried connecting with some of our entrepreneurship contacts at UF, but I soon found that there aren’t many students around Gainesville during the summer. A bit disappointed, I set out to explore the UF campus anyway. The campus is a sprawling, spacious grounds protected by numerous large oak trees adorned with soft, Spanish moss. It was finals week of the summer semester, and very few students were around. I stopped into a few buildings with cool study spaces and empty classrooms, and even scoped out “The Swamp,” home of Gator football. I enjoyed wandering through the calming, thick humidity, comforted both by the ceiling of leaves and the quiet streets and walkways.

Such an inviting campus, I wondered why more students weren’t around, so I investigated some more: Gainesville has about 114,000 residents in city limits, and the metro area has a population of about 258,000. The population growth is slow compared to other cities in Florida. Considering UF has over 50,000 students, Gainesville is tiny – a true college city. It’s probably hard to keep students and alumni around, due to internship and job opportunities elsewhere.

On my last day in Gainesville, I went to a great coffee spot, Maude’s Classic Cafe, for a telecon with the 3DS team. Maude’s is couched in a small shopping center near the Hippodrome Theater, a very walkable neighborhood that is perfect for cranking out some work during the day and grabbing dinner or drinks in the evening. Throughout the call, I kept seeing student-aged people walking in and out of the shopping center from across the street. Why did I take notice? Most of them were wearing Grooveshark (GS) t-shirts.

Our 3DS crew loves music, and we all agree that Grooveshark is one of the best music listening products on the web and one of the coolest startups in the public eye right now. A quick crunchbase search revealed some vitals about GS: Over 100 employees, they’ve only had to raise $1M in funding, and they have one of the largest publicly available libraries of music. Seeing all these t-shirts, my curiosity was piqued… “Is Grooveshark located near here?” I asked the barista. “Yes, they’re on the second floor across the street. They’re pretty chill.” I got goosebumps…

Jess rejoined me at the cafe after the telecon. “We need to make a stop across the street,” I said. “Why?” Jess asked. I replied, “Have you ever heard of Grooveshark?”

Don’t get me wrong; I was nervous. I’ve never crashed a startup’s offices uninvited, but how could I pass up this opportunity? I had to at least check it out.

We wandered up the stairs toward the GS offices and I introduced myself to a random employee. Despite stopping in uninvited, he took us straight to the CTO, Josh Greenberg. We enjoyed the opportunity to chat with Josh about GS, 3DS, and student entrepreneurship. Josh and GS have experienced the same campus challenges that our 3DS team sees at many campuses: students don’t have much experience working in teams after completing their degree, they have little or no experience working with startups and dealing with uncertainty/ambiguity in projects, and similar to the hypothesis I was forming, many technical students find jobs in cities other than Gainesville. It’s hard to keep talent in the area. In response to these challenges, GS has started a program called Grooveshark University, which aims to promote the startup experience among students, giving them tools and training to start their own companies. This is a very cool program, and we’re looking forward to talking with the GS team to learn more about it soon.

A serendipitous startup meeting indeed… it served to remind me about how immensely valuable it is for entrepreneurs to keep their eyes open, ask questions and step outside their comfort zone to seize opportunity. I was hoping to meet some entrepreneurs in Gainesville, and luck was with me. While trying to learn about Gainesville and Grooveshark, I asked questions of my host, Jess, Google Maps, Wikipedia, Walkscore, Yelp, Crunchbase, UF librarians, Gainesville residents, baristas, and (almost) random Grooveshark employees.

Our 3DS crew encourages all young entrepreneurs to strive to develop a healthy curiosity as they pursue their startup ideas. Seek out resources like the ones I’ve listed above, and investigate what type of questions these resources can answer for you. The more resources you are aware of, the more you’ll learn and the quicker you’ll be able to recognize opportunity. When you approach an opportunity with enough knowledge, the last questions you’ll ask yourself should sound like, “Why not give it a shot? Why not check it out?” Go for it.

* Special thanks to the Grooveshark crew. We love what you’re doing, and wish you good luck. Keep asking questions and crushing it!