Serial Entrepreneur Bootstraps First, Raises Funds Later

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Ben Hodson, Co-founder and CEO of JobNimbus, is a serial entrepreneur with a long experience in bootstrapping and fundraising. Read on to see how he has navigated his journey.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

Ben Hodson:?I say that I am from the Seattle area. I was born in Washington State on the east side of the state, but I moved to the west side when I was very young. I went to the University of Washington. I got a degree in business. Then I was interested in computers, so I did a second degree in computer science as well.

I am a guy that likes a lot of different things. I played in a band in high school and college. I played a lot of instruments. I started on piano. I got really good at guitar. Now, I play a bunch of other instruments. I ended up starting a bluegrass band. I learned the mandolin, dobro, and banjo. It is a lot of fun. I have a lot of interests like that. I love the outdoors. I do a lot of surfing and rock climbing and that sort of thing as well.?

Sramana Mitra: Tell me a bit about your educational background. What did you do besides all these interests? What time frame are we talking about?

Ben Hodson:?My first company called Venafi was hashed out of an idea. This was in 2000. I was in school finishing up my last college degree.I was recommended to go and be in an entrepreneur class. I did not think of myself as an entrepreneur at the time. I was working at the power company up in Seattle – Puget Sound Energy. I was a programmer there as I was finishing up my degree. I took this entrepreneur class from my professor, Allen Leong. He was my first mentor. He encouraged me to look at entrepreneurship because he saw my broad range of interests and my self-driven nature.

He thought that entrepreneurship might be something I would be interested in. I took up the class and one of the requirements of the class was to come up with a business idea and build a business plan from it. At the time, I’d finished my business degree and I was doing this class at the end of that degree. I realized that they haven’t taught me how to make a business plan, which is insane in hindsight. It was a great class. I learned how to do a business plan, financial modeling, marketing plan, and a lot of things that I took for granted.

We entered a business plan competition in 2000 that was held by the University of Washington. There were about 500 businesses that entered in their plans. Our plan got into the top 50 teams. This was stunning because this was our first effort at this type of thing.

I met a guy who worked at Verizon Wireless in their IT department that just said, “We just had another SSL certificate expire. That brought down several servers and cost us millions of dollars during that time.” I didn’t know a lot about SSL, so I started digging into it. I got a bunch of resources on encryption and got interested in that.

I realized that the whole system for issuing SSL certificates, keys, and certificate authorities was a brittle system with a lot of points of failure. I wrote some code that would go on a network that would basically crawl every apache and I would be able to see when their certificates were expiring.

Our conversation continues here.

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