Ask Questions First. Get a job at a Startup Second.

A few days ago, I hosted an event at Penn on “how to get a job at a startup.” Eric Friedman and Charles Birnbaum of foursquare, (both of whom I worked with last summer), and Christina Cacioppo of Union Square Ventures offered advice on how to reach out to startups and enter an entrepreneurial world.

Without a doubt, interest in startups is growing. Even at Penn, where people are often funneled down a linear path lined with investment banks and large corporations, startups are now cool. Thanks to the success of companies like Twitter and Pinterest which have gone mainstream, and the rise of “celebrity techies,” startups are perceived to be sexy. (This is gross misconception though because, startups aren’t that sexy. Eric Ries claims they are actually “not cool, not sexy, and totally uncomfortable.” Seems a little harsh to me, but there is some truth to that statement. Startups are hard and messy).

In any case, what became clear during the event is that the majority of the people there, both MBA’s and undergrads, didn’t really know what being in a startup means. Sure it seems exciting and the thought of working on a team with the next Mark Zuckerberg is exhilarating, but most were naive about the actual roles and responsibilities involved and had no clue what kind of startup they want to be a part of.

Eric and Charles emphasized that you need to really buckle down and choose a category or type of startup you are interested in. For example, I’ve become fascinated by disruptive mobile payments systems and truly believe that current credit card and POS systems will be superseded by incumbents that provide more simple, flexible, and efficient systems. I focused my time reading about companies like Dwolla, Square, and Stripe and learned a ton about this landscape, its challenges, and the key players. When I then decided to reach out to get involved with BankSimple, I was able to speak fluently about the company and it competitors I was able to show them exactly why I believe in their product. So as the panelists at the event said, “you can’t just say ‘I want to work at startup’ because that’s the equivalent of generally saying, ‘I want a job.’” Instead, you need to focus your energy, discover your passions, and then go after a few companies in that space.

That is all great advice and certainly true, BUT, one of the things I also realized from talking to my friends is that they simply have no clue what category or type of startup they are interested in. They listened to what Eric, Charles, and Christina said, but were insistent that they can’t choose and came out of the presentation overwhelmed by where to focus.  My response to them was to spend time asking questions and talking to people who actually work in that space. Don’t just read on TechCrunch about the companies that are getting the most press. Instead, get onto the career services website and search for alum that work in an industry you want to be in, reach out to professors, track down friends that are involved in that industry or know someone that has worked in that industry and get an intro to them.

In my experience, people are very willing to talk to students who express genuine curiosity and interest. It’s like dating: take a few startups out for a first date, get to know them, and then decide if it is worth going on a second, third, or 100th. Most universities and college offer tons of resources and outlets for learning and networking, that it’s a shame not take advantage of them. A college student who reaches out to a company or individual for advice out of pure curiosity will 90% of the time be received with warmth and kindness.  Do some homework, reach out, and ask good questions, and people will respond. Bonus points for asking challenging questions that impress these people and give you greater insight into the nuances of the industries. Then, in the event that you decide you really are passionate about that vertical, you have an understanding of the problems and concerns that they face and can more effectively position yourself to be a desirable candidate in their eyes.

Bottom line: be curious, ask questions, and leverage the resources at your disposal.

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