When you were 17, what did you want to be?
I thought I wanted to do something in engineering, probably mechanical engineering. Growing up, I was always building things, like train sets and that sort of thing. The train sets turned into going to Radio Shack all the time. That was like the toy store for me growing up. I would soup up my remote control cars, and one time I built a little robot out of a box with lights and little motors that I pulled out of my remote control cars.
When the Apple II computer came out, my dad rushed out and bought one. My parents were going out of town that weekend, and he said I had to read the whole [manual] before I could use it. The manual was about 1500 pages long. I got through five pages and started messing with it. That's how I started off. My parents also sent me to computer camp when I was growing up. Space camp, computer camp, Saturday school at Northwestern, that sort of thing. They were really pushing me to be a real first-class nerd throughout my childhood.
How did you decide to attend College of Wooster?
My parents both went to the small liberal arts schools and they said, “We'll pay for college, but it has to be a small liberal arts school.” My dad really wanted me to go to Earlham. My mom went to Wittenberg, so she wanted me to go there. I looked at Ohio Wesleyan, Augustana, Miami of Ohio. But Wooster just ended up being the one that I liked best.
It was a great experience because obviously the liberal arts expose you to a lot of different things. I met a lot of people from overseas. You meet some of your best friends in college, and there were a lot of people from India and Pakistan at Wooster. And those are the people I still stay in touch with today. It was an eclectic group that I was in.
How did you choose your major?
I majored in everything at some point. I was interested in being a doctor, so I started a chemistry major. I did physics too. I think I was probably influenced a lot by others at that time, especially with the doctor thing. I don't think I should be a doctor.
I ultimately did an economics major. That, I would say, was probably one of the bigger mistakes in my life, choosing economics. I did it because I thought it would pay, that I could get a job out of school. Not based on any kind of interest whatsoever. What I should have done was physics or computer science.
My senior thesis was on measuring the profitability of corporations in relation to CEO pay. So as the CEO gets paid more, does that actually translate to a more profitable corporation. My results were inconclusive. But I remember pinning it as no. Once you get to that level, you can get a job anywhere, whether you helped or hurt the company.
How did you get from college to where you are now?
After college, I waited tables like everybody else. I worked at Gordon Biersch in downtown San Jose. It was cool. One time the mayor came in and she had a table of 12 people and they gave me the table and said, "Ryan, don't screw this up." And I forgot to put the order in. So I kept bringing them bread, and I thought, I have two choices at this point. I can either go and tell the manager, "Hey, this is what I did - to the most important table.” Or I can go and tell Sandro the cook, "Hey man, I need your help here." So I told Sandro the cook, "Bro, help me out. I need to get 12 meals out there quick."
While I was working at Gordon Biersch, I was also going to San Jose State; I was thinking of going into electrical engineering, so I was taking electrical engineering, courses, which actually translated into my eventually going to George Washington University for a masters in computer science.
I also worked for a small company in Southern California, doing firewall installations; that's how I got involved in computers. And then I moved back to the East Coast, went to GW, and started working for Booz Allen Hamilton, a large consulting company and government contractor.
I was involved in some top-secret projects for the Department of Defense and then some stuff that's less secretive, like doing firewall testing. When I was working at Booz Allen, I was also doing a testing lab for the company where we would test new, emerging technologies. I thought it was really groundbreaking, very interesting stuff, so I took a job with one of those companies and that's where I started getting involved in sales.
I actually didn't fully get my master’s. I got a certificate and then I had two classes left to get my master’s and that's when I got the job that moved me to New York. I took one of the classes at Columbia, but I could never find the other class anywhere in New York. So I’ll always be one class shy. I don't know that the master’s in computer science really helped me. I think an MBA would help me more.
I started working for a company called Cybertrust in New York, doing security consulting basically. In some cases I was selling a piece of hardware but more often, it was services. We’d come in and test the networks, doing what's called “white hat hacking.” It’s called penetration testing, and it’s a good hacker that tries to come in and do exactly what a black hat hacker would do, and see if they can get into the system. I call it a recession-proof industry. The hackers never quit, and they're always coming up with new tools and techniques to break into networks, so we're constantly trying to thwart those efforts.
My job was to explain the service and then offer ways to help secure their system, so stuff like spam filters or firewalls. So you know when you go into work one day, and you can no longer get to a website because IT has done something? That's usually because I sold them something that does that. I never felt good about that, but I like the work. I enjoy talking with people, getting out of the office, meeting with people. But part of sales is you can’t always be yourself.
I worked there for about four years. Since then I’ve worked for a number of smaller companies. I went to a company called Qualys, and they do more vulnerability program testing. I actually worked for that company before the IPO, so that was an interesting experience, working for a company before and after an IPO and stuff.
If you're privately owned, you can invest more in R&D, but once you IPO, Wall Street wants to see those profits going up every quarter.
While I was there, I met the president that Qualys brought in, and I really enjoyed working for her so I followed her over to Microsoft. Microsoft started an enterprise cybersecurity team group to help their customers become more secure. When you hear about Windows getting hacked, it's usually not Microsoft's fault; it's usually because your settings are incorrect. So what we wanted to do was go out and tell large enterprise customers, "This is what you need to be doing."
I worked there for about a year. It’s an absolutely great company. The new CEO, Satya Nadella is a great individual. It's a very open company. There's this mantra within the organization that, I’m not exactly quoting it, but it basically says that during meetings, you should be listening more than you should be talking. They make sure that everyone has expressed their opinions on things and I think that's important, especially within sales organizations. All too often, it's a good old boy saying, "I'm the man, these are my numbers from last quarter, so everyone should listen to me and nobody else." But Microsoft is very different.
What I've actually always wanted to do is know more about coding. I've worked in IT and information security all my career, but while I've been able to get around, I’ve never been really good at developing, good at coding. So that's what I've been working on this year. And I had some ideas on automating things; I think there are a lot of things that graphic designers are doing that could be easily automated, especially when it comes to busywork within Illustrator. So I'm 90% done with this project where you can actually create artwork through Illustrator based on certain criteria. Like if you have an interface with Facebook that knows where you’ve traveled to or where you're from, they can incorporate that into the art.
Now I'm actually in the process of moving back to New York. When I first came on this trip, I was living in San Diego, and people say this all the time, but the energy of New York just draws you back to it. I remember flying back to New York and seeing that skyline and you get pumped up.
Looking back, what seems clear to you now?
I think I wasn't true enough to myself when I was choosing a major. I went in the opposite direction that the majority of people go, who choose what they want to do even though it won't pay. I did the opposite. I loved Wooster and I loved the people there, but it didn't necessarily fit into what I was looking for as far as a major goes. I probably would have chosen a school more closely aligned to what my interests were, which was closer to mechanical or electrical engineering. And I would go overseas, I'd do a semester abroad, expand my horizons.
I don't know what the latest stat is on it, but most people don't go into something that they actually majored in. I think a lot of companies just look for people who show the competence to get a four-year degree. Once you get in the door at one place, you can change your career and take a different path if you want to.