From The Firm to The Motley Fool

Charlene Oldham Issue 15 - Jan/Feb 2015, Legal Leave a Comment

Senior Vice President and Chief Legal Officer Lawrence Greenberg’s transition from a Grishamesque career in counterterrorism, securities, and intellectual property law to a financial services start-up and what he’s learned along the way.


“Lawrence has been at the forefront of the ongoing battle of patenting The Motley Fool’s financial software-related inventions in the United States and internationally. He is a positive, engaging and supportive GC with an instinctive feel for inventions that are patentable and aligned with company business objectives.”
-Michael Lee, Sterne, Kessler, Goldstein & Fox P.L.L.C.

With a resume fit for the protagonist of a spy novel, Lawrence Greenberg seemed to be on the fast track in international intelligence after serving as Attorney for the National Security Agency and Graduate Fellow Analyst – Counterterrorism at the CIA [Central Intelligence Agency].

Greenberg spent the mid-1990s practicing securities and intellectual property law at Wilson, Sonsini, Goodrich & Rosati in Palo Alto, California, and helping found the Project on Information Technology and National Security at the Stanford Center for International Security and Cooperation (CISAC). Then he decided to take a job with a financial services company testing a brand-new business model on the Internet. Nearly 18 years later, Greenberg is still there and serves as Senior Vice President and Chief Legal Officer at The Motley Fool, which now serves millions of investors each month through websites, traditional media and subscription services.

Greenberg recently shared with Forefront his thoughts on taking risks, valuing mentors, firing clients and facing his toughest audience: senior-level law students.


Forefront: Moving from working at an established law firm and a major university to becoming the first General Counsel at The Motley Fool seems like a big shift. What prompted you to make the transition?

Lawrence Greenberg: A friend and former colleague called to ask me to recommend someone who had experience with intellectual property, the Internet and securities regulation, but the first person I recommended wasn’t available, so I strangled my modesty and recommended myself. I had a wonderful job at CISAC, but the chance to work with such a great team, with new technologies, democratizing access to financial information, was incredibly attractive. At the time, it wasn’t entirely clear how The Fool would make money, or even if it ever would, but that was part of the excitement of the opportunity, too.


Forefront: This was one of a series of calculated risks you’ve taken in your career. What made it a risk worth taking? When else along your professional path have you opted to take a similar approach?

Greenberg: I think what makes something a calculated risk, as opposed to a mere gamble, is considering the situation you are getting into and especially understanding what can go wrong, what would happen if it did, and what you can do about it. That way, you can work to mitigate risks. In the case of The Fool, I knew that even if things didn’t work out, I would not be bored and I would learn what it was like to be a General Counsel.

All jobs, even the most established, come with the possibility of failure. All actions come with risks. Sometimes you can get so caught up in the story of what you are doing that you can disregard reality, though. I was once saved from a situation by lack of experience and qualifications, I think, when I interviewed to become General Counsel for a sports franchise. The management team wasn’t right for me, and I lacked virtually all of the skills they needed, but I probably would have allowed my love of sports to blind me to those facts, all the way up until the time of my ignominious failure.


Forefront: How are you able to balance that dual approach of being cautious with taking leaps of faith, both personally and professionally?

Greenberg: I like information. I love information, actually. I love learning as much as I can about a new matter, whether it’s the European “Right to be Forgotten,” how a software tool works or new crowdfunding rules. But time is a finite resource. Money is a finite resource. Certainty is even rarer. Even when you’re just walking, taking a step is a leap of faith—faith in gravity, faith in what is under foot.

So you just have to know what you’re putting your faith in, especially when you are doing something that is different than you’ve done before. And then you have to say, ‘This is a leap I’m going to take.’ One tool I like to use to prepare for decisions is the pre-mortem. We ask, ‘Imagine that it is two years from now, and our new initiative has failed. Why?’ The answers are often terrible, demoralizing stories of our own ineptitude, but they can focus your mind on what’s important.


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Forefront: Being thorough and approaching things from less-than-obvious angles is something you learned from Stewart Baker, a mentor and former General Counsel of the National Security Agency and Assistant Secretary for Policy at the Department of Homeland Security. How did he instill that in his team, and how have you used the approach in your own career?

Greenberg: Stewart instilled his approach by living it, by never accepting pat answers. For him, the first answer to a problem may not be good enough. The second answer may not be good enough. The third answer may not be good enough. So you have to keep looking at problems from different perspectives, challenging assumptions, thinking and asking questions that start with ‘why’ and ‘what if.’ My team and my non-lawyer colleagues may get tired of them, but I think those questions are some of the most powerful tools we have for thinking through problems and coming up with effective solutions.

Forefront: Your father, also a lawyer, has also been a professional mentor for you. What are some important lessons he’s taught you over the years?

Greenberg: My father, Ron Greenberg, is a corporate lawyer at Dentons in New York. The thing that makes him so good is that he actually listens to what people say, which not all lawyers do. He’s not just a lawyer who executes deals—he’s partly lawyer as counselor, partially lawyer as therapist and even lawyer as soothsayer.

So the first step is listening to what clients say they want, because nobody knows what they want more than the clients themselves. The second step is to figure out whether the client is talking about objectives or tactics. When the client says, for example, ‘I want to buy Amalgamated Widgets,’ you need to consider whether the desire is to own that company or just to use some of its assets, which could mean a faster, cheaper, commercial transaction. Listening for what clients mean, rather than just jumping on the words they use, is key. In any case—and this is one of my pet peeves in dealing with outside counsel—you don’t decide what the clients should want and then lecture them about it. When I was an overbearing youth, my mother would gently ask, ‘Who died and made you king?’ I ask that question, about myself and others, a lot.


Forefront: In asking that question, you’ve said it’s sometimes necessary for lawyers to fire their clients. How is that possible as a General Counsel?

Greenberg: As an in-house counsel, I can fire my client right now if it doesn’t meet my standards by leaving. That can be a drastic step, and the economic reality is that it’s easier for me to talk about it than it might be to do it. But, as I tell my students, if you are in an organization that’s doing the wrong thing, if the leaders aren’t worthy to lead you or for you to lead alongside, then you should exit. I’ve been very lucky that throughout my career I’ve worked with people I’ve respected, who were pursuing ends that I’ve shared. Here, our mission is to help others improve their financial lives throughout the world. It’s a worthy objective, and worthy objectives can help justify the time you spend away from home and your family.

GreenburgLawrence_smallForefront: You’ve also taught courses at law schools over the years, and currently teach a class on business associations at American University’s Washington College of Law. What have you learned from teaching?

Greenberg: Teaching makes me a smarter lawyer. In in-house practice, you’re often addressing issues as they arise, and you don’t always get a chance to talk about legal doctrine and the philosophy behind the law, while the academic approach helps me look at issues in context. I also really like engaging with the students, working with them to find out why things are the way they are.

Also, my students are part of the future of the legal profession, and they’ll participate in the development of the law, so I like to pretend that my influence will echo into the future. Finally, if you want to get comfortable with public speaking, there is nothing like standing in front of a bunch of upper-level law school students who may be surfing the Web on their laptops or messaging each other about how boring you are. So, if you can do that, other audiences, except perhaps Cub Scouts, are a piece of cake.

Charlene Oldham is a freelance writer based in Saint Louis. Missouri.

Lawrence's Key Partners:
Sterne Kessler Goldstein Fox (IP Legal matters)Proskauer Rose (Corporate Governance Matters) | Bingham McCutchen LLP (Legal Services) | Taylor Wessing (Corporate Financial Matters)

Charlene Oldham

Contributing Writer at Forefront Magazine
Charlene Oldham is a St. Louis-based teacher and freelancer.

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