#LegalTechLives with Jameson Dempsey of Kelley Drye & Warren LLP and Legal Hackers

Ava Chisling
March 2, 2018

Jameson Dempsey is an associate in the Communications and Privacy & Information Security groups of Kelley Drye & Warren LLP and serves on the board of directors of Legal Hackers. Jameson’s work has earned him a recommendation in Legal500 (Data Protection and Privacy) and a 2016 “Fastcase 50” award, as well as speaking engagements at SXSW, Mobile World Congress (4YFN), CTIA Super Mobility Week, and the Computers, Freedom & Privacy Conference. Jameson earned a B.A. from Boston College and a J.D. from Brooklyn Law School, where he served as Editor-in-Chief of the Brooklyn Law Review and was a participant in the Brooklyn Law Incubator & Policy (BLIP) Clinic.

I see that Legal Hackers is interested in finding solutions. Tell me about your involvement, what it does and why it’s important.

I currently serve as one of the board members of Legal Hackers, although I also co-founded the DC chapter and have been active in the community since it began in Brooklyn in 2012. Legal Hackers is a global grassroots movement of designers, entrepreneurs, lawyers, policy advocates, researchers, students, teachers, and technologists who explore and develop creative solutions to issues at the intersection of law and technology. Since 2012, Legal Hackers has grown to over 80 chapters on six continents. Legal hacking is important to me because it teaches lawyers to think differently about how to address law and policy issues.

I may be the last person to know this, but what is a hackathon in a legal context?

Legal Hackers is all about “legal hacking,” which is the process of developing creative solutions to issues at the intersection of law and technology. The output of legal hacking could be a tech-based solution (e.g., legal tech, reg tech, or civic tech), an improvement in legal services delivery, or a new way of addressing a public policy issue such as data protection, intellectual property, or the sharing economy. We’re inspired by the ethos of the original MIT hackers of the 1960s and subsequent movements.

A “legal hackathon,” on the other hand, is a one or two-day event focused on legal hacking, where attendees self-organize into teams and build prototypes over the course of a day or two, sometimes for a prize but often just to have fun and be creative. New York Legal Hackers hosted the first legal hackathon in 2012, and the first international legal hackathon in 2014.

What has been Legal Hackers greatest achievement thus far, do you think?

I think its greatest achievement has been bringing together a global community of volunteer chapter organizers to meet, share, and collaborate. Legal Hackers’ chapter organizers, who are inspiring legal innovators in their own right, are the heart and soul of our global community.

Legal Hackers is worldwide. Is there a difference in how people approach hacking from country to country?

Great question! I don’t think there’s much of a difference in how people approach legal hacking from country to country because issues like access to justice, the integration of technology into law practice, and the relationship between existing laws and emerging technologies are all global issues. To the extent there are differences, they reflect the size and maturity of the legal innovation community in the particular country/city. In some places, the first order of business for a Legal Hackers chapter is to educate lawyers and policymakers about the concept of “legal hacking” and the ways in which technology and design can improve law, legal practice, and policymaking. In other places where there are already robust law and technology communities by the time a Legal Hackers chapter forms (as was the case in DC), it’s really about creating a forum for those existing communities to convene and solve problems together.

Tell me a few things that lawyers generally don’t know… but REALLY should, given that it’s 2018.

I’m reluctant to generalize, but I think many lawyers could benefit from more project management training. Fortunately, it appears that both law schools and firms are getting much better at providing this training early in lawyers’ careers.

You are also a lawyer, one who specializes in the wireless/cable industry, especially privacy, security, etc. What is a hot issue for you these days?

The biggest issue for me right now is the FCC’s proposal to reform the Lifeline program, which provides a discount on voice and broadband service for eligible low-income households. I’ve spent a lot of my career representing companies that provide service to low-income and rural Americans.

So much of your work is about technology. I wonder how tech has helped you in your practice. Is there one particular technology that you rely on that would surprise us?

I am a big fan of free legal resources, so Cornell LII, Google Scholar, and the FCC’s various public databases are all very helpful in my practice. The more free resources out there for legal research, the better. As far as something surprising, maybe it’s that I still rely heavily on pen and paper for a lot of my legal writing.

And speaking of tech… of course, the folks at ROSS believe very strongly that AI will continue to play a significant role in law. Where do you see AI and legaltech moving forward?

Through my (admittedly brief) 15 years in and around the US legal industry — as a paralegal, litigation technologist, law student, judicial clerk, and now attorney — the general trend that I’ve seen is one away from expensive, proprietary solutions and toward free, open solutions. I think that trend will continue and will be powered in part by AI and ML working in the background to help people (lawyers and others interacting with the legal system) accomplish legal tasks, whether that’s searching for case law, drafting a brief, completing a government form, or negotiating a contract. By lowering costs and other barriers to engaging with the legal system, these free, open tools will advance access to justice.

Does being a member of the Moot Court Honor Society mean you mooted a lot in university?

I was a member of an appellate moot court team at Brooklyn Law School, which was a lot of fun. My teammate and I were runners-up in the Evan A. Evans Constitutional Law Moot Court Competition, which meant we had the opportunity to argue before a panel of judges in the Wisconsin Supreme Court. We didn’t win, but we had a great time.

How often do people misspell your name?

I’ve learned to caveat my name with “like the whiskey,” which tends to reduce spelling mishaps.

And finally, the question we ask everyone — What is one non-work related thing not yet invented you’d like right now?

A Fugazi reunion.

I must admit, I had to Google Fugazi. Now if you’d said the Sugarcubes, we’d be in business! Thank you for your time, Jameson.

Ava Chisling

Ava is an award-winning lawyer and editor who counsels creative types, writes about pop culture/tech+law and sometimes creates ad campaigns. She is Quebec counsel for Momentum Law.