UniCourt Influencer Q&A with Charles von Simson of University of Wisconsin Law School

An expert in fields ranging from entrepreneurship, intellectual property, and the use of open source software (OSS) in the legal industry, Charles “Charlie” von Simson is an advisor to founders and early-stage companies as Of Counsel at Barclay Damon LLP and a Clinical Associate Professor for University of Wisconsin Law School’s Law & Entrepreneurship Clinic.

With his broad array of experience in the legal field, including clerking for a United States District Court Judge, working as a Big Law associate for internationally recognized AmLaw firms, and, most recently, training and testing algorithms for an AI-driven legal tech platform, Charlie offers a unique perspective on how the practice of law is evolving and growing beyond traditional boundaries.

We were thrilled to sit down with Charlie to learn more about his role at the University of Wisconsin Law School and in the legal tech industry at large.

UniCourt: Tell us your story. What is your background, and what led you to what you are doing now?

Charlie von Simson: I spent the first 20 years of my career as an intellectual property lawyer in New York, with an emphasis on technology transactions and litigation. A few years ago, I decided I wanted to teach, so I pursued a professional LLM in law and technology at the University of Toronto and ended up working as an adjunct professor in that program. Along the way, I had the opportunity to work at a legal tech startup in Toronto. From there, I got back on the teaching track and accepted a position in the Law & Entrepreneurship Clinic at the University of Wisconsin Law School.  

UC: What is the mission of the Law & Entrepreneurship Clinic? How did you get involved?

CVS: The mission of the Clinic is to train law students to provide professional legal advice to founders and startups. We work to give students a strong background in business law and help them advise clients who are forming new businesses. We’re also focused on helping grow the Wisconsin economy. Being of practical service to the citizens of Wisconsin is at the heart of the Wisconsin Idea, which is an important founding principal of UW. 

UC: How has the rise of OSS impacted how we practice law? How do you see it affecting the profession in the long term?

CVS: OSS development is fundamentally about collaboration and drawing on talent and experience from inside and outside an individual organization and among different professional disciplines. Lawyers tend to be proprietary thinkers because their job is to single-mindedly protect their clients’ interests. But the proprietary mindset is changing as lawyers see the value in working in multi-disciplinary teams to develop litigation metrics, new billing models, legal research algorithms, automated document analysis, and an almost limitless range of other tools. The OSS mindset will migrate to the way lawyers work with clients. I think the spirit of collaboration fostered by OSS platforms will continue to change the legal profession for the better.    

UC: What is the connection between technological literacy and OSS in the legal profession? How can OSS help lawyers gain the skills they need to become proficient in adopting and incorporating legal tech into their practices?

CVS: OSS platforms are a bridge between software developers and lawyers. A quick scan of GitHub reveals a lot of OSS projects in the legal tech space. Lawyers are working on open source license projects, building legal decision data sets, and developing statistical models of court performance. Most of the projects are relatively new. Lawyers now have a chance to apply their legal knowledge to open source projects and learn a lot about technology in the process. They can deepen their understanding of their clients’ products and seed their own firms with ideas about using technology to support their practices.   

UC: What is needed for the advancement of AI in legal technology? Are there any particular barriers impeding the expansion of legal AI?

CVS: Despite the hype, I think AI development in legal technology has been slower than anticipated. The main reason in my view is that there aren’t enough experienced lawyers involved in training and testing algorithms. It would really help if lawyers could get CLE credit for working on open source algorithms. That would speed progress in development of real AI legal tech applications.  

CVS: What are some of your favorite resources for learning about AI and its intersection with the law?

CVS: MIT Technology Review is the single best source of information on AI development. There are also a few good TED Talks, particularly by Clay Shirky. He has spent a lot of time thinking about opening the legislative process to citizens through open source platforms. I don’t read too much about AI in legal tech specifically. Too many of the articles are written by people who are trying to sell you something.

UC: What are some of your favorite sayings?

CVS: “I’m Cuckoo for Cocoa Puffs.” Do Cocoa Puffs still exist?

UC: What are your goals for 2021? What projects are you working on? Are there any upcoming events in the legal tech space of which we should be aware?

CVS: I’m working with UW law students on two legal tech projects that have been accepted for development by a venture studio. I’m really looking forward to seeing how those projects evolve in 2021. I’m also new to teaching and I have a lot to learn about being a teacher. I want to improve there as well.   

UC: Where can we learn more about you and your work?

CVS: Check out my LinkedIn profile. Send an invitation to connect. It’s a great way to see what people are working on.

Slow, Yet Inevitable, Progress

As Charlie points out, AI development in the legal field has moved slowly, but it is progressing nonetheless. 2021 will likely bring new and exciting developments, particularly as the pandemic continues to force innovation. We look forward to watching these new developments unfold, both within the legal industry and in Charlie’s fascinating career that we’ll continue to watch.

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