An interview with Co-Founder and CEO Aaron Freeman

We periodically interview team members of the SendThisFile file transfer website to discuss their role in providing great managed file transfer service for its customers.

Today, we sat down with the CEO and Cofounder of SendThisFile, Aaron Freeman, to learn more about how SendThisFile came to be, what we’re up to and where we are headed.

Q: Aaron, thanks for your time. How did you come up with the idea?

Aaron: In 2002, I was consulting and earning my PhD in electrical engineering which put me into contact with another web entrepreneur. We had a lot of conversations around holes in the market and I realized there was an opportunity to provide an easy way around email server restrictions.

Q: What are email server restrictions?

Aaron: Well, if you want to send a file from person A to person B, then you must be sure your file size does not exceed the limits of each person’s email server. Since companies try to keep infrastructure and administration costs down, they limit the storage size given to each employee, and then they restrict the email attachment size.

Q: How big of an email do companies typically limit their employees to sending?

Aaron: In the beginning, companies tended to limit their email attachment sizes at around 20 to 50 Megabytes. Their systems wouldn’t allow email out if the attachments were any larger than that.  Even worse, you didn’t know if your recipient had the same or worse restrictions. So even if your email could escape your corporate server, it still might not have reached your recipient. It’s easy to understand how employees got frustrated. I’m not sure where current restrictions are, but I’m guessing they haven’t changed much based on our average file size.

Q: So how does SendThisFile fix this problem?

Aaron: SendThisFile solves the problem by allowing you to easily send large files through our secure servers with no file size limits. We offer simplicity, flexibility and security.

Q: How does SendThisFile work?

Aaron: It’s simple. You create an account, then upload a file to one of our 128-bit encrypted secure servers. Our system sends your recipient an email with a download link. Your recipient clicks on the link to download the file. Files are later automatically deleted from our servers.

Q: How long does a SendThisFile transfer take?

Aaron: That depends on three things: the file size, your upload speed (which is almost always way slower than your download speed), and the SendThisFile plan you have chosen. If you are on our free plan, we throttle your connection based on our server load. It still gets there pretty quickly though. It’s much faster and cheaper than sending a USB thumb drive or hard drive through the mail.

Q: How much does SendThisFile cost?

Aaron: We have different plans depending on how much you use the service. A lot of people try out the SendThisFile Free file transfer plan to test the waters, then upgrade later to a higher class of service. Even with paid plans, we easily beat the competition on price.

Q: Okay, fun questions now. What has been the biggest challenge managing the business?

Aaron: Keeping up with our growth has been the biggest challenge. Early on, we solved a lot of the technical problems that can go wrong with reliably sending files. You’d be surprised at how many fly-by-night operators who couldn’t do this have come and gone since 2003. Maybe 200 or so.

Q:What development, event, or new understanding since you started has had the most impact on your original plan? How has your plan changed in response?

Aaron: We have learned that speed and reliability are paramount. We had a large company response early on so we have created additional service plans for the professional and enterprise customers.

Q: What’s next for you?  What’s next for SendThisFile?

Aaron: I love what we have accomplished at SendThisFile and if anything, our growth is only accelerating. The Internet user base is still growing so we will be laser focused on providing reliability, speed, security and simplicity while maintaining our growth. That excites us and we’re really looking forward to see how our service evolves over the next few years.

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