Why did I go from BigLaw to litigation finance? Good question.

Since joining the Lake Whillans team this summer, I’ve been asking a lot of questions.  To effectively finance litigation our team must completely understand the factual and legal basis for the claim.  So we ask questions. But they have to be the right ones — informed by diligent research on the particular case and our legal knowledge and experience.

Fortunately, I’ve had a lot of experience asking questions.  In a former life, I worked as a newspaper reporter.  I’d get a news tip or hear something on the police scanner, and would have to figure it out.  Go to the scene. Interview the people involved.  Put the events in context. And, of course, ask the right questions — often of people who had little time or patience for dealing with a reporter.

I was lucky enough to attend a phenomenal law school that had questioning at its very core.  The University of Chicago Law School is famed for its commitment to the Socratic Method.  This ethos carried over to my work on The University of Chicago Law Review.  As editor-in-chief, I participated in innumerable meetings and discussions with fellow staff members and authors where we questioned and tested everything.

Post-law school, my reporting experience melded with my academic experience.  I was fortunate enough to clerk for two brilliant, humble, and fair-minded judges, from whom I learned how to look at a set of real facts and apply the law.  And then to explain the decision in a clear and uncluttered manner.

When I moved on to practice law at Wachtell, Lipton, Rosen & Katz,  as in my reporting days, I had to start with the facts.  But this time, I was looking through the lens of the law: What facts matter in the particular legal context?  What did they mean as applied to the law?  And how do we present these facts and law most favorably to our client?  (Of course, while working at Wachtell, partners, other associates, and clients also asked me a lot of questions about law, facts, strategy and everything in between.)

I began thinking about litigation finance as a career over the past few years while talking with Lake Whillans co-founder Lee Drucker, who happens to be an old college friend.  The more I thought about it the more sense it made.  Litigation finance combines all of those skills that I’ve learned through the years:  the analysis of facts, the application of law, and, of course, the continual questioning of arguments, positions, and assumptions.

The past few months have borne this out.  We are an inquisitive group.  We seek to really learn the story, and then once we’ve digested it, to ask a lot of questions.  We will question your facts and test your arguments.  We will engage in a candid dialogue about a case’s strengths and weaknesses.  Doing so allows us to have confidence in our decisions and offer competitive terms.  And those that explore funding with us will have the benefit of knowing they’ve received a full, fair and honest evaluation.

While the complex cases we explore differ from the stories I picked up by listening to a police scanner, the same essential questions guide our evaluation:  who, what, where, when, why and how.  I’ve been asking them for a long time, and am excited to keep doing so on the Lake Whillans team.