Growing up, Cunningham ’04 was always fascinated by his father’s Apple II Plus - one of the company’s older models released in 1979.
He would sit around the house pulling apart the large beige computer and then, piece by piece, he’d reassemble it. But as he grew older, it wasn’t just technology that interested him. In college, Cunningham became more and more interested in understanding and arguing the law. After getting his Masters in Computer Science, Cunningham attended UC Hastings and found that he could combine his two interests in one dream career. Now, a Senior Litigation Counsel at Apple Inc., Cunningham spoke with us about his experience working at one of technology’s leading companies and the advice he gives to people looking to pursue a similar path.
1. How did UC Hastings prepare you to work in Silicon Valley?
I had a fantastic experience at UC Hastings. I loved law school tremendously and being in this location; being in San Francisco was a big part of that. UC Hastings is right next to the California Supreme Court, it is right next to the 9th Circuit Court of Appeals, the federal court houses are right here as well. It really feels like you are at the center of law. You can do whatever area of law you want to do here and there is a tremendous amount of opportunity to do that in a big urban center. I didn’t really want to get into patent litigation when I was at UC Hastings. But because of my background in computer science and because of the schools prime location, I had the opportunity, when I graduated, to go work at a law firm that did a lot of patent litigation. So really it was the location, excellent professors and excellent programs. And particularly the moot court program here was incredibly valuable for me to learn the basic skills of standing up, arguing, and just being a lawyer.
2. What initially interested you in a legal career?
I always thought that I was going to grow up and be an engineer or a doctor or something like that. And when I was in college I remember having to make a decision whether I wanted to take organic chemistry or philosophy. And I really wanted to take philosophy. And I think at that point I realized maybe I shouldn’t be a doctor. I really enjoyed getting up and speaking. I went to grad school in computer science because a family friend told me “You don’t want to be a lawyer, all lawyers hate themselves.” And I actually took that advice for a while. But when I was in graduate school and I decided that I didn’t want to ultimately become a professor in computer science. I was trying to figure out what I wanted to do and I thought, I’ve always had this interest in going to law school, I should just do it and see what happens.
I always knew that I wanted to stand up and argue in front of judges and juries.
I like the experience where you are going to go to court and someone is going to tell you whether you are right or you are wrong. That doesn’t happen in transactional law as much because you get to do deals and everyone feels good about the deal. But at the end of the day nobody says you were right and you were wrong.
Another reason I was always interested in law, was my desire to understand how society worked, how the rules worked. That’s one reason I loved law school because when you leave law school you don’t really have to be a lawyer to use the legal education. Just understanding what you can get sued for, what the rules are, how laws are made is tremendously powerful no matter what you do. I love just understanding that aspect of society.
3. What is the best piece of advice anyone has given you professionally?
I think the best piece of advice I have ever been given professionally, is not to treat your career as a linear progression. Which is to say, you don’t start at a company and then work your way up. The people that I have seen that have had really interesting careers, and have really advanced, have tended to switch jobs when things got stale. They don’t just stick it out in a particular position. It is important to accept that at some point in time you need to pick up and move on when you’re not growing any more. It feels really risky and sometimes it doesn’t work out as well as it could work out. But it also enables you to have tremendous growth potential because it allows you to switch context, learn new skills, and not get pigeonholed. I think that advice has been incredibly helpful for me.