Dorm Room Fund’s First Investment, Firefly, Makes Instant Screen Sharing Easy Breezy


Penn Philosophy undergrad major and serial entrepreneur Dan Shipper (UPenn ’14) is a hot commodity these days. When not fielding funding offers from top-tier VCs and angel investors, rejecting a much-talked-about viral online job offer by Jason Freedman of 42Floors, or rubbing elbows with the likes of Jason Fried of 37Signals, Dan is hard at work building his second startup, Firefly. Born out of a recent Penn Apps Hackathon, Firefly is a screen-sharing service that allows customer support reps to better serve customers with website-related issues. We sat down with Dan shortly after Firefly bagged its first seed funding from First Round Capital’s Dorm Room Fund to get an inside scoop on his hot new startup.


Wharton Journal: Tell us about Firefly. How did you get started, and where did the idea come from?


Dan Shipper: My dad called me one day and started complaining about not being able to point things out from one computer to another. He spends a lot of time on the phone with other people looking through documents and websites, and he wanted a really easy way to tell someone “Look at this part of the site”, because right now the process for doing that is really broken. You say things like, “Look at the top right of the page, there’s a link that says ‘Contact Us’ click that. Do you see it?” And that sucks because it’s difficult to describe what you’re talking about and it’s difficult for the person on the other end to figure out where to go.


I thought about that and talked about it with my co-founders Patrick and Justin and they built the first version of Firefly at the PennApps hackathon last January. While they were there, a company came up to them and asked to buy it for their support process. And that’s when we first started to think that we might have something cool.


WJ: I hear you’ve turned down quite a fair bit of funding offers – and even a widely public job offer from Jason Freedman of 42Floors. What made you say yes to the Dorm Room Fund?


DS: It was money at the right time and money on our terms. Dorm Room Fund is really the first VC we talked to that understood that it’s possible to build a company without dropping out of college and moving to San Francisco. That philosophy resonated with us, and the terms that they give the money on made it almost impossible to say no. Couple that with the beautiful office space they’ve built for us and other companies to work out of and it was really just the perfect situation for us. We’ve gotten a lot of other offers for funding, but this one was the first one that really made sense for the stage we’re at.


WJ: You don’t find a lot of philosophy majors hacking away to build the next big thing on the Internet. What’s your story?


DS: I’ve always been interested in business, and programming. I started coding in 5th grade after I read a Bill Gates biography and decided I wanted to build a Microsoft competitor. The thing about programming that always appealed to me is that it’s the only way to build a business where the only cost is your time. So as a 10 year old the only way that you’re going to be able to build a scalable business is if you know how to code.


That kept me interested in programming and kept me building things. As for philosophy, that’s also a part of me that I’ve always been interested in. I’m a big humanities guy (I was also Editor-in-Chief of my high school newspaper) and philosophy is important to me because I think it helps frame the way I look at the world, and analyze and interpret the things going on around me. It’s also a great way to learn how to construct an argument.


And all of those things happen to come in handy in the business world.


WJ: So this is actually your second startup. Can you tell us about your first startup, Airtime? What happened there?


DS: Basically what Airtime did is allow any company to have a consistent, centrally-controlled marketing message at the bottom of every email they sent out. We did this by allowing companies to put a banner at the bottom of their employees’ emails that rotated between different products, tracked clicks and tracked impressions. We’re actually still working on it on the side, but it’s basically in maintenance mode at this point.


We developed technology for Airtime that I think you’ll see more and more in emails over the next 5-10 years, like the ability to change the signature content based on the device that the email is opened on and the location that it is opened in.


I think there’s also a real problem with organizational email signatures right now, in that they’re always out of date. There’s always some person in a company that sends out an email every month or two saying, “Update your email signature to this. We’re pushing product X this month.” And Airtime solves that problem by allowing the signatures to be centrally controlled.


However, I don’t think that solution we built initially was quite perfect – the variety of email technologies old and new and the restrictions placed on email content makes that really difficult, and so the product didn’t get as much traction as we had initially hoped.


I think it’s something we might come back to in the future though.


WJ: What’s next for Firefly post-seed funding?


DS: Right now we’re working on getting as much distribution as possible with small-to-medium sized businesses with our SaaS platform, trying to find the best way to start getting traction with the enterprise market and doing partnerships to help speed things up. We’re excited about where this thing is going.


WJ: Any advice for other student entrepreneurs at Penn / Wharton?


DS: Chase revenue/traction first and venture money later. Use everything as a learning experience. School is an incredible time to learn as much as you can about entrepreneurship when the cost of failure is very low. When you’re in the real world and your business fails, it’s a big deal with real consequences. If you’re running a bootstrapped student startup and you don’t get as much traction as you hoped the worst thing that happens is you wake up on Monday morning and go to class with everyone else. And hopefully by Tuesday you have another idea to work on.


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