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Interfacing with an information technology entrepreneur

E. Kelly Fitzsimmons started with coconuts and then sold four companies. A serial entrepreneur discusses security and technology startups and why embracing failure works.

Some people have good ideas, and they remain just that, ideas. E. Kelly Fitzsimmons is an information technology entrepreneur whose leadership skills have helped turn ideas into successful security and technology companies. She built and sold several security startups. How did she do it? Fitzsimmons plans to reveal some of her tips on how to survive the ups and downs of life as a serial information technology entrepreneur in her upcoming book, slated for publication later this year. Like most well-known entrepreneurs, she persisted despite a few hard-hitting failures.

Fitzsimmons started her information technology entrepreneurship as founder and CEO of Sun Tzu Security, a consulting company, which merged with Chicago-based security lab and advisory firm Neohapsis -- now owned by Cisco -- in 2003. She served as CEO of Neohapsis from 2003 to 2006. A year later, she co-founded HarQen, the web telephony company behind and Voice Advantage communications software. In 2011, she received the Silvertip PwC Entrepreneurship Award from the Angel Capital Association. In 2012, she and Martin Geddes co-founded the Hypervoice Consortium to focus on the future of voice communications. Currently, she is the founder of virtual reality production company Custom Reality Services. The company's film, Across the Line, premiered at the Sundance Film Festival in 2016.

Marcus Ranum caught up with Fitzsimmons as she was -- where else? -- running from one gate to another at the Hartsfield-Jackson Atlanta International Airport.

Kelly, let's jump right into it -- how did you start off as an entrepreneur?

E. Kelly Fitzsimmons: I started around age 7. I lived in the Florida Everglades -- my mom is an artist, and she decided to leave my father and live down there. So I moved from Milwaukee to Florida when I was 6 years old, and it became very clear to me, early on, that my mother's plans to make it as an artist were not going to work out and some money was desperately needed. I started selling coconuts and driftwood to tourists.

(Laughing) How did you get into higher technology after coconuts and driftwood? Your work has always been focused on tech to some degree, so I assume it's your background.

Fitzsimmons: Always, always. I started programming in pascal when I was 11 years old. I was a weird kid: I had dyslexia and pretty severe ADHD. I remember, as a kid, getting a present of a 2-XL Robot that would quiz you on trivia, and it ran off an 8-track tape. And I thought it was fascinating and took up programming -- it was so exciting to be able to create something from scratch. That was how I got started. When I moved back to Milwaukee, my career really didn't take off until I was in my twenties. 

The dyslexia aspect fascinates me. I was very dyslexic as a kid and had to train myself out of it, which is where I believe I got my ability to focus on stuff.

Fitzsimmons: Starting around age 20, I realized I was having trouble reading, and I started paying attention to reading for clarity, reading code, reading for speed -- different ways of [doing it].

My skill was seeing things at a higher level and being able to see things really early. And, of course, to communicate; I was always willing to listen and talk and be the 'nice' interface.
E. Kelly Fitzsimmonsinformation technology entrepreneur

You have a string of successful information security startups behind you -- how did your career evolve?

Fitzsimmons: Really naively! I started out in information security in 1995. I was working for a bulletin board system after I finished grad school -- I was fascinated with the BBS scene, and then the World Wide Web happened and changed everything. I looked at that and said, 'What could possibly go wrong?' And it occurred to me that it could go really, really, horribly wrong. So I started a company in 1996, an early pure-play security firm [Sun Tzu Security]. That was about a year before Neohapsis. We ended up merging into that company with Greg Shipley [former CTO] as part of a roll-up that was happening in the industry. These were all difficult decisions.

Aside from technology, I've noticed that all of your work seems to be about communication -- extremely social. Is that a fair assessment?

Fitzsimmons: That's so funny, but it's true! I think it's all about interface. I always noticed how broken things were and how much simpler interfaces could be. That was how I wound up doing the startup on voice control and processing. I want to have technology work for me -- I want to be able to be able to talk to the computer and have it just work. Also, I wanted it to be fun! As you remember, was jokes as a killer app -- to get people to talk to their computers. It's the communication that I'm fascinated by.

I've always seen consulting as a social activity; you're communicating with your customer and it's all about clarity. Even back to when you were selling the coconuts, you've been in the consulting business.

E. Kelly Fitzsimmons, information technology entrepreneurE. Kelly Fitzsimmons

Fitzsimmons: I was selling a vision. Here I was, 7 years old, and the tourists would be saying, 'Twenty dollars for a coconut?!' I would look at them, point at the tree as if I had climbed it, and they'd give me the twenty dollars -- this poor kid is obviously working very hard for these coconuts. I was a little P.T. Barnum.

Computer security has consistently been accused of being a boys club, and I agree with that assessment. Has being a woman ever affected your experience as an information technology entrepreneur? My impression of you is that you just steamroll anyone that gets in your way.

Fitzsimmons: I do, but in the nicest way possible. The important thing is to not make enemies and to work with people that I love. I've noticed that some people don't know what to do with me, or what to make of me, and that's been true at all of my startups. It's not like I have any great technical skills; many of my people were far more competent than I was. My skill was seeing things at a higher level and being able to see things really early. And, of course, to communicate; I was always willing to listen and talk and be the nice interface.

I'm going to make that the title for this interview. Are you in a position where you can talk about that book you've been working on? It sounds great.

Fitzsimmons: It's coming out in December. What I'm doing is writing a book for people when they hit their first 'wall of failure.' In my opinion, that's when you really start to become an entrepreneur. All of us live with a sort of misguided sense of our technical powers and our native genius, and when we hit that wall it can be really devastating. Basically, we think we're invulnerable and everyone else is an idiot. That's one way to interface with the world, but nobody likes those people.

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