Law at a Cross-Roads

Are lawyers and entrepreneurs polar opposites?


♫ I feel a little strange inside

 A little Dr. Jekyll, a little Mr. Hyde...♫

– Music, Lyrics and recorded by: Rory Gallagher

I have been reading about entrepreneurs lately, particularly those interested in start-ups. I have been left with the impression that not only do lawyers and entrepreneurs speak different languages, they seem to approach problems differently.

Adriana Gardella, in Forbes magazine (, wrote an article entitled: “The Secret of Lawyers-Turned-Entrepreneurs?” In that article she interviewed Leslie Firtell who, after law school, founded Tower Legal Solutions, a company that offers legal staffing, consulting and compliance services for law firms and corporations. Regarding Ms. Firtell, Gardella wrote:

“I don’t think like a lawyer, I think like an entrepreneur,” Ms. Firtell said. She explained that entrepreneurs must be willing to take risks that would make many lawyers uncomfortable. “Lawyers are tied to rules and deadlines, but as an entrepreneur, you never know what your day will look like,” she added.

Scott Edward Walker, in VentureHacks ( in an article “Top 10 reasons why entrepreneurs hate lawyers” wrote as his #1 reason: Lawyers are often viewed as deal-killers because of their failure to set a positive tone and their annoying habit of raising all sorts of reasons why a particular deal won’t close or why a particular idea won’t work. One of the better lawyers I worked with at a firm often said: “Good lawyers are able to identify significant potential legal problems; great lawyers provide solutions to those problems.”

OK so does that mean that lawyers can’t be entrepreneurs? The Law Insider ( ran an article entitled: “Lawyers Moonlighting as Entrepreneurs” and stated that in the past, lawyers have been “mischaracterized as risk averse, unimaginative and perfectionists to a fault.” It then goes on to list five lawyers who have started innovative businesses.

So perhaps to turn a lawyer into an entrepreneur requires them drinking an elixir that, like Dr. Jekyll and Mr. Hyde, transforms a risk-adverse lawyer into an innovative, creative and risk-taking business person. ( in “If I want to become an entrepreneur, where do I start?” stated:

“What you want, therefore, is an astute awareness of a need that is currently underrepresented in the market. You want to spot a product or service that can go places – original or not.”

Well, we have no shortage of legal needs that are going underrepresented in the current market. What we need are lawyers who are willing to think outside the box and start legal start-ups that can meet some of these needs. Perhaps we need to create an incubator environment that will mix lawyers with entrepreneurs in the same physical space that will allow each to cross-pollinate each other’s thinking.

We may end up creating a new group of lawyers who feel a little strange inside: a little entrepreneurial, a little lawyerish.

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