File sharing in the business world has become as common as sending email with attachments. In 2005, when Jesse Lipson launched ShareFile, that was not the case. Lipson founded ShareFile in the days before cloud computing was all the rage. By the time Citrix acquired ShareFile in October 2011, the 100% bootstrapped company had grown from one employee to 165.
Sramana Mitra: Hi, Jesse. Let’s start with some context about you, ShareFile, and your acquisition by Citrix.
Jesse Lipson: I’m the founder of ShareFile, and I am a software developer. I built and launched the product in November 2005. We were a bootstrapped company. We grew without any funding and grew organically over time. We were acquired by Citrix in October 2011. At that time, we’d scaled up to about 80 employees. We operate in the business file sharing space.
SM: When you started ShareFile in 2005, what was the landscape like? Would you talk about what you saw when you started this company?
JL: Prior to this company, I had a website design and development company. We did services work. The idea for ShareFile came out of the fact that we had multiple clients who were asking us to build pretty much the same thing, which was a password-protected area where they could set up folders and exchange business files with their clients. At the time, there were a couple solutions out there. There was a company called Xdrive. There was another one called Streamload. But this was still before the big trend of cloud computing. If you look at Google trends for the term “cloud computing,” it wasn’t until late 2007 that the term was really being searched for and used. We were about 18 to 24 months ahead of when cloud computing became a popular buzzword that was used in commercials and all that kind of stuff.
Also at the time, some of our current competitors were launching. I think YouSendIt launched in maybe late 2004, and Box.net launched in early to mid-2005. There were a few of us who were getting into the space, but it was not seen as a hot space by venture capitalists. Most of them saw it as an idea that had already been done by some of these early players. I think we sensed that traditional file transfer protocol (FTP) type methods were becoming a little outdated as web applications started to proliferate on the Internet. We saw an opportunity there. I don’t think we understood it would get as big as it actually has become, especially with the launch of the iPad over the past couple of years, but we definitely saw that there was room in the market for additional players.
SM: You said you bootstrapped the company. Would you tell us a bit about your bootstrapping story? Our audience loves bootstrapping stories.
JL: I didn’t come from a computer background. I graduated with a degree in philosophy, but I had a lot of ideas for technology entrepreneurship, and I realized I couldn’t do much with them without funding unless I learned software development. So, I taught myself software development just by doing Google searches and things like that. I started to learn how to code, and then started a Web development company. That brought in some revenue, just doing services projects for clients. It also helped me hone my skills as a software developer. Because I could do my own software development, I was able to get the ShareFile product launched without any funding. From a customer acquisition standpoint, we’ve always been focused on business customers. We don’t have a free product or a consumer-focused product. We started with a simple offering. We had certain plans that cost a certain amount a month on a subscription basis. We started off advertising on Google AdWords. The first month, I put up some pay-per-click ads, which are pretty cost effective. They were especially cost effective at the end of 2005 and early 2006 when we were doing them. We started off getting a small number of free trials. Some of those converted to paid accounts, and we just built up our base of paid accounts over time. I started off by not taking a salary for the first couple of years when I launched the company, so I was able to reinvest the revenues from our subscription customers into acquiring more customers. Eventually, we hit a critical mass where we had enough revenue to hire our first employee, and then our second employee, and so on. We have now 165 employees.