How to be a legal entrepreneur

Lawyers have many helpful attributes, but their aversion to ambiguity needs to be overcome.

How to be a legal entrepreneur
Kate Simpson

Lawyers have many helpful attributes, but their aversion to ambiguity needs to be overcome.

In my last column, I discussed the disruptive mindset needed to face the oncoming challenges to our profession. In preparing for that article, I spoke with a number of entrepreneurs. All of them were founders of exciting Canadian-based legal tech disruptors that firms and in-house legal departments are beginning to licence and use.

I wanted to get a sense from those entrepreneurs of what it takes to pivot away from a stable(-ish) career in law to one without guardrails, a reliable income and needing a completely different skillset. It is one thing to have the “there has to be a better way to do this” thought that most of us have when we are doing some tedious repetitive task at work. It’s quite another to pursue that thought day in and day out to figure out how to build an entire business model around it, let alone then persuade enough people to pay for it!

In talking to these entrepreneurs and others that I follow (like some kind of groupie), I realized that the journey is not only highly unique for each person but at the same time follows a familiar pattern of highs and lows, stops and starts, tears and laughter. I’ve picked just three that stood out for me during these conversations.

An idea with wings!

As Sahil Zaman of Closing Folders says: “It’s not just about having the ‘A-ha’ moment.” The idea is most certainly not fully formed in that eureka shriek. It is fleshing that idea out into something that people will buy that’s the hard part.

But the idea is where the journey begins. The shape that the idea stage takes is different for many. And, indeed, how long that shaping stage takes and how many pivots one might make during it is wildly different for those that have taken this path.

This thinking stage, pondering different ideas, concepts and business models, was more than six months for Noah Waisberg of Kira Systems — part of that while still at Weil Gotshal & Manges LLP. Others, such as Aaron Wenner of CiteRight, had a shorter ideation stage and got to a prototype that he could show lawyer friends earlier than that. But it will be two years in development by the time Wenner launches his winning product this year.

Giving an idea wings requires both time and creativity. Entrepreneurs need to “Think Different” about the problems in front of them and that requires focused time. This isn’t completely alien to lawyers, but both creativity and finding the time to draft something non-conforming and innovative seems such a luxury at the early stages of a lawyer’s career.

Patience and perseverance

The second common thread with all of those I spoke to was the need for both patience and perseverance. That journey of one step forward and two steps back requires tenacity in what you’re trying to achieve.

The entrepreneurs I spoke with admitted to a number of pivots during these early idea stages (even changing the complete solution idea!) in response to initial feedback and after further thought. That requires a commitment to the process and a belief that it will all work out in the end. Pivoting from an original idea is sometimes referred to as “failing often and failing fast.” This kind of pivot is much more familiar to lawyers. We all have examples of trying one approach in a deal or case and needing to try something completely different before it concludes. It’s what we learn from that experience that differentiates the good from the great.

For Zaman, Wenner and Waisberg, that persistence to turn an idea into a team and funding and bring it to life is a full-time unpaid job and one that happens post-law. Adrian Camara of Paper Interactive realized the first thing he would need for his idea to become a reality was “18 hours a day and a committed team.” This team often includes spouses and children.

The mountainous journey that entrepreneurs take is certainly not one for us all. And perhaps it is why we hold those who forge that path in such high esteem — or why we should.

Embrace ambiguity

Embracing ambiguity is not familiar territory for most lawyers. Messy ambiguity is precisely the situation that people instruct lawyers to help them solve. We help create clarity,  whether that’s understanding the regulations that businesses are subject to in any acquisition deal or understanding the rights that a party is entitled to in a legal dispute.

Entrepreneurs need to embrace this messy period rather than race to leave it behind. There is energy in ambiguity. And it’s OK not to have all the answers. Entrepreneurship is about carving your own path rather than taking the well-trodden path of others.

“Legal entrepreneurs need to make decisions quickly and on imperfect information,” as Zaman puts it. This, I think, is why some lawyers find the entrepreneurship journey a risky one on which to embark. The deep analysis and research that lawyers use when advising clients ensures that any decision that is made is done with absolutely all of the best information considered and checked.

All of the legal entrepreneurs I spoke with are former lawyers. Some left practice soon after articling; others had more than a few years under their belt before doing so. I believe lawyers have what it takes to join the ranks of disruptors in legal technology and other spaces. But to make the leap it is really this third attribute that lawyers need to learn to feel some comfort with first. Entrepreneurs need to develop acceptance with not knowing all the answers. Instead, they need to persevere with their idea until they suddenly have to pivot. And they have to be ready to take that completely different untrodden path, even if there’s only a nugget of belief in their belly that it will lead to success.

Yes, entrepreneurship is risky, but understanding the type of risk involved will surely help make such a decision less momentous.

Kate Simpson is national director of knowledge management at Bennett Jones LLP and is responsible for developing the firm’s KM strategy and initiatives. Opinions expressed are her own.

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