How to Make the Move from Big Law to a Startup

From left: Leigh Gross, Yamile Nesrala, Ngoc Nguyen, Courtney Browne and Molly Siems at CommonBond’s “Break (from) the Law — From Big Law to Startups” on March 8th.

When I graduated from Harvard in 2005, banking and lawyering were still perceived as the golden tickets to a lucrative career. There were, of course, already signs of the startup boom — Mark Zuckerberg had just dropped out of Harvard to launch Facebook, two of my classmates would soon turn their passion for cosmetics into a business called Birchbox, and another would revolutionize personal financial planning with LearnVest. I caught the startup bug too and joined Endeavor, a nonprofit that supports entrepreneurs all over the world.

But as Wall Street imploded and my friends left their banking gigs for business school, I decided it was time to go back for a professional degree. I had already taken the LSAT and the idea of spending my days poring over an Excel model gave me chills, so law school — with its academic bent and seeming indifference to numbers — seemed like a better fit. By the fall of 2010, I was back in Cambridge with a casebook in hand. And, like so many of my fellow Harvard Law School grads, I joined Gibson Dunn, a top law firm in New York, after graduation.

At Gibson Dunn, I worked on cases ranging from oil spills in the Amazon to white-collar matters. In some ways, litigation is well-suited to my personality and strengths. When I wasn’t buried in doc review, I found the law to be a highly intellectual profession that values research and writing skills — a good match for a slightly nerdy liberal arts major like me. But I missed the creativity, ownership, and dynamic environment I experienced at Endeavor. So after nearly 2 years in Big Law, I joined the marketing team at CommonBond. Based on that experience, here’s what I recommend when evaluating the decision to transition from Big Law to a startup:

Decide whether you want to practice law. Your legal background really gives you two options: you could practice law at a startup or you could take on a business role that, at first glance, doesn’t appear to use your legal training.

  • Practicing law at a startup: Like most other companies, startups need in-house counsel. But early stage companies usually don’t have big legal teams that can train junior lawyers. So if you’re smitten by the startup world and still want to practice law, stay at a firm long enough to be comfortable managing cases or negotiating contracts on your own, which tends to happen between your third and fifth year.
  • Taking on a business role: If the law isn’t for you, the earlier you make the switch, the sooner you can start applying the skills you learned from your legal background, and start building additional skills that will help you succeed in your new career.

Understand the trade-offs. It’s no secret that Big Law pays well. Given that the average student debt for law school graduates is around $112,000, staying at a firm long enough to pay off your loans can be tempting. But if the law isn’t for you, delaying your switch comes at a hefty price: you’ll be sacrificing the opportunity to figure out where you want to work and what role you want to play. While the early days of startup life generally aren’t as lucrative as Big Law, many startups incentivize their employees with stock options that could become highly valuable as the company grows. Also, you can find other ways to save money to make the decision more feasible. For example, refinancing your law school student loans with CommonBond can significantly lower your monthly payments and save you over $14,000 in interest payments, on average.

Use your network to find your ideal startup. Once you’re ready to make the jump, come up with a list of 10 companies you’d like to work for. This exercise can be surprisingly hard for lawyers. Unlike MBAs, law students don’t spend two years reading case studies or hearing from CEOs and founders about their experience starting and managing a business. I approached it by tapping into my personal network and attending as many startup events as I could (check out CommonBond’s upcoming Break from the Law panels). Talking to people who actually work at startups helped me figure out what was out there and what working at one was actually like day to day.

Don’t forget second-degree connections. Friends are important, but when it comes to job searching, it’s friends of friends who matter most. The power of second-degree connections is particularly key when you’re switching industries and need to branch out beyond your close professional connections, who are probably mostly lawyers. LinkedIn is a great tool for finding these connections. When I was interviewing for CommonBond, I looked up one of my interviewers and saw she was connected to a friend of mine from college. I reached out to my friend, who went out of her way to put in a good word. Don’t be shy about leveraging connections — a warm introduction can be incredibly helpful both to you and a company looking for the right hire.

Avoid legalese. Lawyers can be great writers, public speakers, researchers, negotiators, and project managers — but sometimes we speak legalese, which business people don’t understand. Instead of using words like “deposition” and “discovery” in your CV, say “interview,” “due diligence,” or “strategy.” And remember, numbers are your friend — whether it’s the number of people (junior lawyers, paralegals, local counsel) who reported to you or the size of the deal you worked on, numbers will help your future employer better understand the magnitude of your accomplishments.

My final piece of advice is to remain confident in your abilities. You jumped through a lot of hoops to get to where you are: the LSAT, the Blue Book, the bar exam, that memo on the intricacies of ERISA that you had to write at a moment’s notice. The skills you honed in the legal profession will help you in your next role. Breaking into the startup world is just one more challenge. Except this time, you get to decide what’s on the other side.

Yamile is the Campus Relations Manager at CommonBond, where she focuses on sponsorship and outreach opportunities at business and law schools. Before joining CommonBond, she was a litigation associate at Gibson Dunn and spent two years at Endeavor, a global organization that supports high-impact entrepreneurs in emerging markets. Yamile earned her BA and JD from Harvard, and has a Master of Philosophy from Cambridge University.