Hey there Legal Rebels! 👋 I'm excited to share with you the 15th episode of the 2025 season of the LawDroid Manifesto podcast, where I will be continuing to interview key legal innovators to learn how they do what they do. I think you're going to enjoy this one!
If you want to understand the extraordinary journey of a legal tech visionary who has consistently stayed ahead of the curve, from early web adoption to AI innovation, you need to listen to this episode. Dennis is a quintessential digital disruptor whose career trajectory offers invaluable lessons for lawyers navigating today's rapidly evolving technological landscape.
Pioneering Legal Innovation Through Technological Revolutions
Join me as I interview Dennis Kennedy, Director of the Center for Law, Technology and Innovation at Michigan State University College of Law, co-host of the Kennedy-Mighell Report podcast, and recipient of the American Legal Technology Award for lifetime achievement.
In this far-reaching conversation, Dennis takes us through his remarkable journey from small-town Indiana to becoming a legal tech pioneer. He shares how his early fascination with punk rock and literature shaped his approach to challenging the status quo in legal practice. Dennis reveals how he recognized the transformative potential of the internet in 1995, famously declaring it "the second coming of the printing press," and how that insight drove his career pivot toward legal innovation.
Dennis offers rich insights into his time as VP of Digital Payments at Mastercard, his thoughts on the current AI revolution, and his perspective on how lawyers must adapt to maintain relevance in a rapidly changing technological landscape. His observations on the similarities between today's AI revolution and the early internet era are particularly illuminating for legal professionals navigating this pivotal moment.
The Skinny
Dennis Kennedy's path from a small Indiana railroad town to becoming a legal tech luminary reveals how curiosity, adaptability, and a willingness to question established practices can lead to remarkable innovation. The conversation traces his journey through English literature, law school, pioneering legal tech roles, and his current work in legal education and AI. Dennis shares profound insights about the accelerating pace of AI development, comparing it to the early internet era, and challenges the legal profession to engage meaningfully with technological change rather than resist it. His story demonstrates how seemingly disparate experiences, from punk rock to farming to corporate law, can converge to create a unique perspective that anticipates change before others see it coming.
Key Takeaways:
Dennis recognized the internet's transformative potential in 1995, comparing it to "the second coming of the printing press" – this vision has guided his career ever since
The legal profession must actively engage with AI rather than resist it – those who can bridge legal expertise with technological understanding will be increasingly valuable
AI is pushing us to confront fundamental questions about our legal system, from judicial decision-making to access to justice
Today's AI revolution mirrors the early internet days in its energy and potential to fundamentally transform society and professional practice
Dennis recommends focusing on your strengths rather than trying to improve weaknesses – delegate or eliminate tasks you don't enjoy when possible
Complex systems theory offers valuable insights for understanding how law interacts with rapidly evolving technologies
The concept of "platform lawyers" or "ecosystem lawyers" is becoming increasingly relevant as products become more interconnected and difficult to define in traditional transactional terms
Law schools and legal professionals who avoid engaging with AI risk becoming irrelevant as clients and businesses move forward with adoption
Notable Quotes:
"I keep saying, what are the legal issues if we have a mirror in a pop-up clothes shop where people can try on clothes and order them and pick them up... It's really hard to determine what the product is and who's involved in it... How do we have to figure out how that all works together?" - Dennis Kennedy (37:45-38:29)
"I missed the whole damn Internet. I just missed it all like it's gone, and I can't be part of it. So I over the weekend, I put up a web page, and then that web page led to most of the rest of my career in a lot of ways." - Dennis Kennedy (29:44-30:07)
"I'm looking forward in some ways to retiring. It's not because I'm not going to be thinking about these things. I just want to spend more of my time on some of those things." - Dennis Kennedy (1:01:20-1:01:25)
"AI is pushing us to the most fundamental issues and questions really quickly... We say, well, we couldn't have AI be a judge, right? And then we start to say, well, what is it that's magic about biased human judges?" - Dennis Kennedy (48:28-48:57)
"I've seen so much change in the last two and a half months in AI that is staggering to me. If you're having a conversation about what AI was like last summer, you're not even describing what's going on in the world right now." - Dennis Kennedy (47:29-47:47)
Clips
Future Lawyers and AI: Bridging the Knowledge Gap
Creating A Legal Tech Course
A Leap from Law Firm to Startup
A Memorable Encounter at ABA Tech Show
Dennis Kennedy's story embodies the essence of legal innovation – recognizing transformative potential before others, having the courage to pivot career directions, and maintaining a continuous learning mindset. His journey from small-town Indiana to legal tech pioneer demonstrates how combining diverse interests and experiences can create a unique perspective that anticipates and adapts to technological change. As the legal profession faces the AI revolution, Dennis's insights about engaging with technology rather than resisting it offer a valuable roadmap for legal professionals seeking to remain relevant in a rapidly evolving landscape.
Closing Thoughts
What strikes me most about my conversation with Dennis is his remarkable ability to anticipate technological shifts before they become mainstream. From recognizing the internet's transformative potential in 1995 to his current work with AI, Dennis exemplifies what it means to be a true digital disruptor in the legal space. His journey reminds us that innovation often comes from cultivating diverse interests and experiences, from punk rock to farming to corporate law, and using them to form unique perspectives.
The comparison Dennis draws between today's AI revolution and the early internet days is particularly resonant. Both represent watershed moments that fundamentally alter how we practice law, and both require us to confront core questions about what value lawyers bring to the table. As Dennis aptly points out, the legal profession faces a choice: engage meaningfully with technological change or risk irrelevance as clients and businesses move forward without us.
I'm inspired by Dennis's experimental approach to innovation, treating new ideas as hypotheses to be tested rather than solutions to be defended. This scientific method applied to legal innovation offers us all a framework for navigating uncertainty. As we continue to witness the unprecedented pace of AI development, Dennis's insights provide not just a history lesson in legal tech evolution, but a blueprint for those of us committed to shaping the profession's future rather than merely responding to it.
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Cheers,
Tom Martin
CEO and Founder, LawDroid
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