I grew up in New York, about 30 minutes north of Manhattan, and went to school in a tiny square-mile town. As a kid I played a lot of sports, and was captain on a lot of teams, both organized and unorganized. I really thrived on the team aspects, like getting everybody close to reaching their full potential. I had a sense that I’d like doing something that involves building and strengthening teams. By no means did I ever think that was going to be software. Software was just kind of a lucky stop for me that turned into a career.
I played anything with a ball. Baseball, soccer, football, basketball, tennis. I was year-round dribbling or shooting or throwing something. I played sports straight through high school, then had the abrupt reality of understanding that I wasn’t quite good enough to play in college, even at a Division III school. A rude awakening.
Full disclosure: I was an underachiever academically in high school, and I was late with the college application process, starting with studying well. My sister, Jennifer, was at Keene State. She was four years ahead of me, and she was really enjoying it. So I visited and applied. One thing led to another, and all of a sudden I was attending Keene State College.
I was pretty clear after my freshman year I wanted to be in business, so I pursued the degree in management. I think the most notable moment for me at Keene State was through Dr. Neal Pruchansky, who kind of whipped me into shape. I was taking one of his very intense classes my junior or senior year, and there was a moment when I realized: I’m a little bit smarter than I think I am, and if I work very hard and get stimulated by the right environment, I can get near my own full potential. I’ve said this to him – I’ve written him twice since I’ve graduated, even recently, to thank him for being that source of stimulation for me.
While I was at Keene State, I applied to go to school in England, at Oxford, for a semester. I was inspired to go because of a combination of starting to do well at Keene with some good professors that I admired and getting intellectually engaged with the work. I’ve put it this way to a number of people: Before I got to college, I thought it was cool to be cool, but when I went to Oxford, and then studying with Dr. Pruchansky, I realized it was cool to be smart.
Studying at Oxford taught me two things: One was that it really is more interesting to be intellectually engaged than socially engaged. But the second was a stepping stone for me – living abroad exposed me to what’s now a full passion of my life, which is travel. The real dynamic behind travel is just anticipating and collecting as many experiences as I possibly can. After my time at Oxford, I cruised around Europe as a 19-year-old with a close friend, and that gave me a big itch to start traveling. And here’s what it led to. I’ve told this story so many times to the young folks in our company who ask me how I got started. Neal Pruchansky, Oxford, Oxford led to me wanting to travel. The day after I graduated from Keene, I got in my car and I drove to the West Coast. I did not want to go to Wall Street, which was what many of my New York friends were doing. Thanks to my experience in Europe, I just wanted to keep seeing and exploring. And that changed my life, because I fell in love with San Francisco, I met my wife there, we had our three kids there, I found my career there at Oracle. I had no interest in software whatsoever. I just needed a job. It was the most entry-level job you can have. You put a headset on and you make a bunch of phone calls and try to sell their software over the phone.
I stayed at Oracle for 16 years. The first six months, I had to bluff my way through knowing what software was. I hadn’t taken any computer courses at Keene State, so I had to learn on the fly, studying on weekends. I was super hungry, and I remain that way today. I found myself there 16 years later running a meaningful part of Oracle’s business.
I left Oracle to be the CEO of a Chicago company called Big Machines, which makes software to help sales reps configure price quotes. I knew in my early 20s that I wanted to be a CEO in software. I absolutely knew it. I was working for Larry Ellison, the CEO of Oracle. I found him to be one of the most dynamic people on the planet, and he just happened to be the CEO of Oracle. He’s an amazing leader. Then the opportunity came, I went to Big Machines and, coincidentally, two-and-a-half years later, Oracle bought Big Machines. So I was back at Oracle.
Why software? I had a sense back in the late ’90s that software was going to eat the world. In a good way. A software company would lead every industry. I really believed that then, and it’s now. Let me give a few examples. The biggest retailer in the world doesn’t own a store. It’s Amazon.com, a software company. The biggest hotel company in the world doesn’t own a room or a bar of soap. That’s Air B&B. The most valuable transportation company in the world does not own a car. That’s Uber. And you know the most valuable music distributor in the world doesn’t own a record or a store. That’s Apple. So you pick your really asset-intensive industries, and they’re today being led by software companies.
So, one, I wanted to be part of that. Two, the problems that software solves, they’re really intellectually fascinating. They solve all sorts of human problems, and I wanted to participate in that. And third, to be frank, there’s a ton of money to be made in software. It’s wildly profitable. And I wanted to participate in that. Look at the most valuable companies in the world today; they’re all software companies: Apple, Google, Amazon, Microsoft, Oracle, IBM, Salesforce.
I left Big Machines to come to Lanyon, which is in the event registration business. When there are huge business conferences, with thousands and thousands of attendees, Lanyon powers all of the registrations. And when attendees are at the conferences, they register on our software, we push the agendas out to their phones through our mobile apps, and we scan where they go during the day and get that info back to the conference hosts, so they can see what the folks were interested in. We are essentially the business registration event software platform for Fortune 2000.
The work is really satisfying, and it comes back to team building. As a CEO I’ve got a few jobs. One is to build healthy, strong teams, and that is first and foremost. The second thing I spend a lot of time doing is looking for problems. And then I’ve got really smart people who convert those into opportunities, which is what we pay them to do.
My family is in Dallas now, but we will probably go back to San Francisco one day. I’ve been married to my wife, Zoe, for 16 years. She cares for the kids and the home, and also does a lot of nonprofit work. She was an art history major at Lafayette College in Pennsylvania, so art’s a big part of her life. My eldest child, Hugh, is in sixth grade. I’ve got a nine-year-old named Willa and a five-year-old named Daisy. Hugh is all sports, pretty much all the time. And an avid reader and a lover of music. Willa is all horseback; she competes in Texas and California. Daisy, she’s drinking a bottle of happy every morning, has a fantastic imagination, and just does what five-year-olds do. . .
We travel quite a bit. I cook a lot – a great way to seduce these kids to stick at the table with us for dinner each night is to cook them great food. My wife and I see a lot of live music, so we’re still pretending that we’re in our late 20s. Our weekends are spent on ballfields and in stables and barns. As a family, that’s the kind of stuff we like to do. Spending time with my family is important, and I leave my office every day between 5 and 5:15 so I can get home and spend the next three or four hours with my kids. Despite my career in high tech, we’re a very low-tech family. There’s one iPad; it stays in the kitchen. The kids don’t have phones. When their friends come over, they put their phones in a little phone bowl.
I’m super grateful for my time at Keene State. I went in as a young guy who was a little imbalanced with priorities, and I left there ready to take on the West Coast. They were very transformative years for me. And so my story really comes back to this: I met a professor at Keene State who intellectually provoked me, I took that to Oxford, Oxford took me to San Francisco, and San Francisco took me to my family and my career. It really is sequential like that.