I had a lot of odd jobs growing up. I was a bus boy at a pizza place in college; I worked at a bookstore; I was a clerk at a bankruptcy law firm; and I did cold calls for Smith Barney (now Morgan Stanley) trying to get people to buy bonds. I even worked as an English tutor in Barcelona for a little while after I graduated from college. And then, I did what a lot of people who have no idea what they want to do with their lives do: I went to law school, at Emory.
Luckily, I met my wife there, but otherwise it was not for me. I switched over to the MBA program. At the time, Jeff Sonnenfeld, who is now a well-known professor at Yale, sent a note out to all the students saying, “I need a superstar who wants to intern at an internet company.” This was the summer of 1997 and I was a very early and massive user of the internet, and thought, “Well, maybe I qualify.”
I interviewed at Information America, which was an Atlanta-based company that sold public records over dial-up and had been bought by Thomson Reuters. They wanted to build a web presence: a public record search engine. I got to do everything. I did product design, e-commerce, advertising, PR, and growth marketing. Time magazine even did a story on us because they couldn’t believe we were doing hundreds of thousands of dollars in credit card transactions online.
I didn’t have an engineering background, the furthest thing from it, but it didn’t get in the way of anything. I was the original vibe coder. Instead of vibe coding myself, I was explaining the vision to the head of design and head of engineering.
I ended up staying on for nine months, because this was my baby, this new fledgling website. It also turned out to be my first entrepreneurial experience, my first product experience, my first internet experience, and my first search engine experience, which became the thing I did for the next fourteen years.
Courage and experience
That first job set me up to have all the courage and experience to join this other entrepreneurial venture, called eTour, which lets you discover new websites based on your interests. I started it with some classmates during our last year of school. By the time we graduated in May, we already had 10 or 15 employees and were a top 50 site. We were one of the top websites before the market crashed in 2000 and then we sold to Ask Jeeves.
Just seeing that was an important lesson because I have had to lead companies and teams through multiple crashes. There was the one in 2000 there was another in 2008 there was another during COVID. The first one taught me how to persevere through all of that: from knowing how to survive as a corporate entity to leading teams to knowing what’s on the other side.
Then, if you fast forward to 2008, I had just raised money for my new startup. I actually turned down a public company CEO job to do it with three kids and a mortgage, and it was probably not the smartest idea. But, I had an idea that I really believed in, which was a video search engine.
In October of 2008, I offered to give the money back because the recession was so grim. My investors, who included people who’d been with me at Ask Jeeves, just wanted us to stay with it. And so we spent 2009 stealth building, and didn’t launch until the end of 2009. When it launched, it was really well received and some of the people had worked with me at Ask Jeeves and eTour. So we had faith in ourselves, and we had faith that things would come back, which they did. It started with that first job. That first job also taught me how to do hard things and not to be afraid of them.
Driving through the fog
My dad was a lawyer. My mom was a teacher. My paternal grandparents had a fish and chip store in Harlem. There was no basis in our family to understand business. I didn’t read the business section of the newspaper until business school when someone told me it was like the sports section, but for business.
I get asked a lot of questions now by my own interns or by people just starting out. Everybody wants a template for how to grow their career, or to become a CEO. I’m a bad example. I feel like I drove through the fog figuring out my own pathway.
As told to Shalene Gupta. This interview has been edited for length and clarity.
My First Job is a recurring series in which prominent business leaders share what their first job was and what they learned from it.