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Hair-Raising Fun: Why Join a Startup

Career Column
W hy should lawyers consider joining startups? “Because it’s hair-raising fun! You feel like you’re on the precipice of a cliff and guzzling from the fire hose most of the time,” Suzy Fulton, vice president of operations and general counsel at Appspace, colorfully answers. “Working alongside and supporting the most innovative, passionate, and creative business people and investors” is another fun perk of working at a startup, according to Dana DuFrane, vice president of legal affairs at The RealReal. According to DuFrane, “There is such an awesome alchemy that is created when all this comes together to build a company out of and around innovation.” Aside from fun, however, startups offer great opportunities to all lawyers, whether they are currently in-house, at a law firm, or in the government.

Become an all-purpose, Swiss army knife lawyer

Lawyers at a startup give broad advice on everything legal-related and much more. “A lawyer will get a variety of experiences in all sorts of areas of law. It's a really exciting opportunity,” says Sarah Feingold, general counsel at Vroom.com. “If you're interested in exploring being a generalist, startups require that you be the Swiss Army knife of lawyering,” says Alexandra Sepulveda, deputy general counsel at Udemy.

As a startup lawyer, “You’ll stretch yourself and your areas of practice and expertise in ways you’ve never imagined and crack out of the risk-averse cocoon that most lawyers live in,” Fulton says. She explains, “IP law? Sure. Commercial real estate law? Sure. General corporate law? Sure. HR and employment law? Sure. Privacy and security compliance? Sure. Corporate M&A? Sure. Tattoo artist in your lobby? Um, don’t ask, but okay.”

“Depending on the stage and culture of the startup, joining one is like joining a family with one very ambitious goal,” Mia Butera, former legal counsel at Instacart, explains. “For me, it was easy to get swept up and work harder and with a more single-minded focus than I've ever worked before. Working in a startup made me a better, more well-rounded lawyer and advisor because for everything I did, I had to think about how it would affect the company as a whole.”

Evaluating risks proactively and effectively is yet another skill startup lawyers perfect to an art form. After all, startups are all about taking calculated risks to yield great rewards. As a first year associate at a big Silicon Valley law firm, Su-Jin Lee, vice president of legal and associate general counsel of PopSugar, once sat in on an initial meeting with some partners and a few young founders of a new startup. “These founders were bold with big ideas and also pretty candid. One of the founders, with a sardonic smile, said something to the effect of ‘Here are the lawyers, where our dreams go to die,’” she says. This bold assertion still resonates with Lee. “I decided at that moment that I would not be that kind of lawyer. Working in a startup means that even after nearly seventeen years of practice I am still constantly learning new things, championing exciting ideas and a part of making dreams happen,” she explains.

Partner with business for real impact

Joining a startup is an ideal move for lawyers seeking to truly make a significant, visible impact. Every action in a startup will have an impact, often immediately, because a lawyer’s duties are significantly broadened at a startup. According to Sarah Feingold, who recently left Etsy to take the general counsel position at Vroom.com, “A lawyer should consider joining a startup to be more creative and to empower business growth while appropriately protecting the company from liability.”

Startup lawyers are truly in the middle of the action and receive all perspectives. “Being at a startup I am in ’The Arena,’ as Teddy Roosevelt put it,” says Stephanie King, general counsel at AdRoll. “I have a direct influence on decisions — many which can make or break the company. I get to be a real team player with the business. I share the ups and downs, emotionally and financially,” she explains. King adds, “Honestly, I am a bit of a control freak — being in-house gives me much better access to information, which was always a bit of a challenge as outside counsel. Yes, it's messy sausage making and there are lots of mistakes, but you get to learn about law and business, push yourself, think creatively and quickly, and that gets me up in the morning every day.”

As DuFrane explains, “As in-house counsel working to advise and support in that setting, we really are helping to lay the railroad tracks while the train is moving. It’s an incredibly exciting, creative, and energizing dynamic in which to layer the necessary structure, clarity, legal guidance, and common sense good in-house counsel brings to the startup team.” Perhaps most satisfying is that fact that legal advice in a startup has a real time impact. “Our advice really matters — it has such immediate impact [in startups] where there are few, if any, layers and little to no established policy and process, which we get to build as we support, nurture, and help these amazing companies grow and extraordinarily smart business people and partners succeed. It can be exceedingly scary — you cannot hide from the tough decisions — but oh so much fun and satisfying,” DuFrane explains.  

In fact, according to Michelle Leetham, vice president, general counsel, and secretary at Rodan & Fields, “If you don’t join [a startup], you may pass up the best job of your career where you will learn and grow more than you could have imagined.” She explains, “Startups offer the chance to partner closely with the business as it develops, allowing lawyers to make a profound impact, particularly when developing the right policies and processes to avoid risk while supporting growth. Every day is fresh, challenging, and an opportunity to apply what you know to new areas of the law.”

Transform your career

A broad range of skills, significant business impact, and great opportunities are the recipe for a successful legal career. According to Michelle Fang, vice president and general counsel at Turo, “Transitioning from a large established in-house legal department to a startup provides an exceptional opportunity to get closer to the business you support. You are expected to not only provide strong legal counsel, but also help steer the direction of the company whether it’s business strategy or company culture. As the only attorney at a startup, you don’t have the benefits of a large team of legal experts to rely upon when questions outside your area of expertise arise. These challenges force you to learn new things, develop new skills, and help build the confidence in yourself that you can in fact handle any problems that come your way.”

Similarly, “Working at a startup teaches you how to provide real time business-minded advice, rather than delivering perfect legal advice in a vacuum,” says Stephanie Carpenter, chief legal officer at VoloAgri Group. Carpenter explains, “Larger companies often have the luxury of considering perfect legal advice and implementing some form of the best case scenario. Working at a startup often doesn't provide this luxury. You have to make quick decisions with a less than full set of resources and make the best case decision for the company. It truly teaches lawyers how to balance business and law.”  

For many attorneys, startups also offer opportunities to transition into a different career. As Leetham explains, “There can be significant personal rewards. In four years, my group has grown from two to eleven legal and compliance professionals, and the company’s annual revenue run rate has increased approximately ten fold.” She continues, “I am having a lot of fun trying to hang onto the rocket ship!”

For lawyers seeking “hair-raising fun” and a unique, creative experience, joining a startup might be the best decision they’ll make. Ultimately, however, although startups offer great opportunities, they are not for everyone — just like any other job. As Lauren Dubick, chief privacy officer and general counsel at Magnetic, a marketing technology company, explains, “I was advising a friend recently regarding whether she should join a startup. I told her that if she enjoyed getting deeply involved in a few legal issues and looking at each legal issue from every conceivable angle, then a startup culture was not for her. On the flip side, if she enjoyed being practical and coming up with creative solutions to a wide range of issues, she would likely find it to be quite satisfying.” 

About the Authors

Olga-MackOlga Mack, career columnist for ACCDocket.com, is a startup lawyer who enjoys advising her clients to success and growth. Currently General Counsel at ClearSlide, she previously worked at Zoosk, Visa Inc., Pacific Art League of Palo Alto, and Wilson Sonsini Goodrich & Rosati. She is a passionate advocate for women and has founded the WomenServeOnBoards.com movement. @OlgaVMack

Katia BloomKatia Bloom is a fast-paced and strategic commercial lawyer. Currently, she is heading up legal for the US subsidiary of Germany-based internet security company Avira. Previously, she was a founding partner at E Squared Law Group and in-house counsel at Anesiva.



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