Here is a wildly embarrassing video about how I hustled my way into Red Hat. I recommend starting at the 3min 15seconds mark to watch the blooper reel. It has the best bits. Enjoy!

They say great entrepreneurs have grit and hustle. I’m not sure if I am a great entrepreneur but I have been known to have moments of hustle.

One such moment was in 1999. Back then, I was a second year MBA student at the University of North Carolina, focused on technology / marketing / entrepreneurship. I have always been entrepreneurially minded but I figured that I should go work for a software company for a little bit before starting out on my own.

It was frothy back in the Dot Com Boom days. There were lots of startups to go work for. But, I found few that were truly interesting and innovative. In my search, I stumbled upon a little company called Red Hat and was intrigued. It was based in Durham and still very small, less than a 100 people. More importantly, I found its open source model and community fascinating. I believed that it was truly going to change how software was developed and deployed. Back then, Red Hat was rough around the edges but I could see that there was a diamond in there. I had seen this diamond in the rough before so I knew what to look for.

I graduated from college in 1993. As a computer science major, I had been fairly tied into the pre-Web Internet and even ran a Bulletin Board System (BBS) as a kid. But, I took a detour after graduation and joined the Peace Corps. By the time the “World Wide Web” burst on the scene in late 1993 and 1994, I was living on a remote island with no connectivity. My days were filled with teaching and coconuts instead of coding and startups. (Which was awesome btw!) I missed the Web’s grand entrance but deeply understood what it looked like before becoming mainstream. I saw the same thing with Open Source in 1998 and 1999. Fortunately for me, I was near its epicenter and determined not to miss out on it again.

I wanted into Red Hat but I needed to get their attention. So, I recruited my business school friends to help me make a video, stating my case. I pressed the video onto a CD-ROM and FedEx-ed to the CEO. Easy to do now but no so easy in 1999.

It worked! (in addition to a few other tactics like organizing a school-wide presentation for the CEO and telephoning the head of marketing every week.) I joined as an intern and then converted to a full-time employee around graduation. Meanwhile, I let my more lucrative offers at places like Dell Computer expire. Red Hat IPO-ed on scant revenue later than summer and managed to survive the Dot Com Bust to become the $15 billion 10,000-employee gorilla that it is today.

Some of that $15 billion is likely because of the awesomeness of this video.