From Practicing Law to Building Legal AI: My Chat with Bob Ambrogi on LawNext
Where I share my recent conversation with Bob Ambrogi about life, work, and the pursuit of happiness through community-building
Welcome, legal tech enthusiasts and future-forward counselors! 🤖⚖️ Pour yourself something rebellious (perhaps with a splash of punk rock attitude) and settle in for some technological truth-telling. Today, I'm sharing highlights from my recent chat with the legendary Bob Ambrogi on his LawNext podcast, where we explored my journey from traditional lawyer to legal tech entrepreneur.
If you've ever wondered how a California probate attorney ended up building AI tools in rainy Vancouver, teaching at Suffolk Law School, and organizing punk-infused legal tech awards ceremonies, all while maintaining a serious mission to transform legal service delivery, you're in for a treat! Consider this your backstage pass to the sometimes messy, always exciting convergence of legal tradition and technological revolution. No AI hallucinations here, just real talk about building bridges between what law has always been and what it could become.
This substack, LawDroid Manifesto, is here to keep you in the loop about the intersection of AI and the law. Please share this article with your friends and colleagues and remember to tell me what you think in the comments below.
I recently had the pleasure of joining Bob Ambrogi on his LawNext podcast, where we explored my journey from California lawyer to legal tech founder in beautiful Vancouver (when it's not raining, that is!).
First off, I need to thank Bob for that flattering introduction where he suggested I might have "figured out how to use artificial intelligence to clone myself." If only! Though with the pace of AI development these days, perhaps I should add that to my product roadmap...
My Legal Tech Journey
My journey from attorney to legal tech innovator wasn't a dramatic pivot but rather a natural evolution of my lifelong passion for technology. As I shared with Bob, I've been enamored with tech since childhood when I first encountered the Apple II. My legal career began traditionally enough with a California-based probate practice (which I still maintain remotely after 14 years), but I found myself increasingly drawn to the intersections of law and technology.
The real catalyst came when I read about Joshua Browder helping people contest parking tickets in London through automation. Chatbots were, as I told Bob, "love at first sight." I immediately saw the potential for chatbots and AI to revolutionize legal information delivery. The birth of LawDroid nine years ago started modestly as an experiment with a chatbot designed to help people incorporate businesses in California, which, remarkably, was still a paper-based process at that time. What began as a simple test quickly evolved as I saw positive responses from users and began exploring partnerships with legal aid organizations, a natural fit for scaling their services through technology.
These early years were formative as I learned about automation and incorporated early AI models like BERT to understand natural language input. Rather than an "all-in" moment that most associate with entrepreneurship, my path was incremental, testing concepts, refining approaches, and gradually expanding capabilities as the technology and market evolved.
Perhaps the most surprising revelation from my journey was how long it took for the legal industry to catch up with where my head had been all along. I never anticipated it would take seven to eight years for the concepts I was exploring to gain mainstream traction within the legal community. When generative AI exploded onto the scene with ChatGPT in November 2022, it felt like vindication, suddenly everyone was talking about the potential that I had seen years earlier.
The pandemic served as an unexpected accelerant, forcing legal professionals out of the "this is how it's always been" mindset and creating receptivity to technological solutions that might have taken another decade to achieve otherwise. This convergence of factors has finally created the environment where the ideas I've been championing have found their moment, making it easier to have meaningful conversations about using this technology to enhance our professional lives.
LawDroid Today
As I explained to Bob when he asked that important question, "What the hell is LawDroid and what does it do?", our mission is fundamentally is to promote justice everywhere by helping lawyers work smarter, not harder. We've developed two core products that approach this challenge from different angles.
LawDroid Copilot, which we launched in January 2023 (just two months after ChatGPT hit the market), was designed specifically for busy attorneys who lack the time or inclination to master prompt engineering. My bet was that most lawyers wouldn't want to climb that learning curve, so we curated all the complexity into simple buttons that allow them to summarize documents, create counterarguments, and perform other legal tasks without needing to craft perfect prompts. It's essentially a more secure, private, and legally-focused version of ChatGPT.
Our second product, LawDroid Builder, takes things a step further by enabling users to build custom AI agents through a no-code platform. It's remarkably comprehensive yet accessible; we offer templates for phone assistants that can answer calls, website assistants that capture leads, and even client interview tools that generate documents automatically. In fact, we used LawDroid Builder to create LawDroid Copilot itself, demonstrating the platform's robust capabilities.
The evolution of our business has naturally included a significant consulting component, which I recently formalized under the name Deep Legal Consulting. Throughout LawDroid's journey, I've worked extensively with legal aid organizations, state courts, state bar associations, law firms, and corporate legal departments to help them understand and implement AI effectively. What's fascinating is how the lessons I've learned working in the access to justice space apply with equal relevance to corporate and Big Law environments, it's just that these approaches haven't been widely applied in those sectors until now.
The consulting practice addresses everything from the fundamental "buy versus build" question to preventing organizations from "reinventing the wheel," which happens all too often. As I told Bob, working with an experienced legal AI vendor provides significant advantages: we've encountered and solved countless implementation challenges across diverse client situations, allowing organizations to leverage that collective wisdom rather than starting from scratch. This consultative approach reflects my belief that successful AI adoption isn't just about the technology itself but about understanding the specific value it can create for each organization and implementing it in ways that align with their unique objectives.
The Mindset Shift in Legal AI
One of the insights I've gained through my work with legal organizations is that successful AI implementation begins not with the technology itself, but with mindset, which precedes both tactics and strategy. During my conversation with Bob, I shared what I've come to call "Moravec's irony" (though perhaps I should rename it "Martin's irony" because I’ve based it on feedback I have personally received from lawyers): the paradoxical situation where lawyers simultaneously complain when AI doesn't magically solve all their problems, yet express anxiety about AI potentially replacing them. The irony, of course, is that they're essentially frustrated that the technology isn't yet advanced enough to take their jobs!
This contradiction reveals a fundamental misunderstanding about AI's role in legal practice; it's not an either/or proposition where technology either fails completely or renders attorneys obsolete. Rather, it's about finding the complementary sweet spot where human expertise and technological capabilities enhance each other.
The notorious Schwartz case perfectly illustrates the dangers of approaching AI with the wrong mindset. The problem wasn't fundamentally with the technology itself but with viewing AI as an oracle, an infallible, magical entity whose outputs should be trusted implicitly. As I emphasized to Bob, this oracle mindset is precisely what led to the citation of non-existent cases. Had the attorneys approached the technology with an "assistant mindset" instead, recognizing that assistants, whether human or digital, make mistakes and require supervision, the outcome would have been drastically different. Their failures stemmed not from using AI, but from abdicating their professional responsibility to verify information.
The transition to effective AI implementation in legal settings requires abandoning abstract discussions about “use cases” and focusing instead on concrete value creation. Too often, vendors speak about AI capabilities in the abstract without tying them to specific problems that create measurable value for legal organizations. This approach has led to widespread experimentation without strategic implementation.
The firms finding success with AI aren't those chasing the latest technological trends; they're the ones approaching implementation with a problem-solving mindset, asking "What specific challenges can this technology help us overcome?" rather than "What can this technology do?" This value-first orientation represents the most important mindset shift required for legal professionals navigating the AI landscape.
Teaching the Next Generation
My journey into legal education began when I was invited by Dyane O'Leary to join what I called "the Legal Tech Avengers" at Suffolk Law School in Boston. The faculty roster reads like a who's who of legal innovation: Marc Lauritsen (who was recently recognized for his lifetime achievement at Suffolk’s LIT Conference), Dean Andrew Perlman, Gabe Teninbaum, David Colarusso, Quinten Steenhuis, and even Sam Glover of Lawyerist fame.
When Bob asked about the structure of my course on "Generative AI and the Delivery of Legal Services," I had to laugh and admit that I initially had "no idea what I was doing." This has been something of a pattern in my career. I tend to jump into new challenges headfirst and figure things out as I go. Law practice was like that, founding LawDroid was similar, and teaching proved no different. What started as a daunting 13-week course to design from scratch evolved into an immersive educational experience that pushed both my students and me to explore the frontiers of legal technology.
The course development became an adventure in itself as I essentially wrote a textbook on the fly, with my students serving as accountability partners each week. The curriculum evolved into a comprehensive exploration of generative AI's impact on legal practice, covering everything from historical foundations and ethical considerations to practical applications and real-world case studies.
I didn't stop at traditional teaching methods: I created a multi-modal learning experience that included weekly workbook exercises, guest speakers like Scheree Gilchrist of Legal Aid of North Carolina, discussing access to justice, and Troy Doucet from AI.law, offering Legal AI vendor perspectives, mini-lectures for each class, and even custom podcasts created through NotebookLM. Perhaps most meta of all, I developed a chatbot tutor trained on the course materials that could help students work through complex concepts outside of class hours.
The most important aspect of my teaching philosophy has been ensuring students don't just understand AI concepts in the abstract but can apply them practically in their future careers. The culminating capstone project requires students to develop a comprehensive AI implementation plan for a law firm. My goal is for them to walk into job interviews or their first positions with something tangible they can show to prospective employers: "Here's an AI implementation strategy I've developed that maps out how we could leverage this technology effectively."
This practical orientation reflects my belief that legal education should prepare students not just to understand emerging technologies theoretically but to navigate their implementation challenges in real-world settings. Today, in fact, marks the final capstone presentations for this semester's class, a bittersweet moment as I've genuinely enjoyed watching these future legal professionals develop their understanding of how AI can transform legal service delivery. Their perspectives and questions have been as educational for me as I hope my teaching has been for them.
American Legal Technology Awards 🏆
The American Legal Technology Awards is entering its sixth year, and I'm thrilled that we'll be hosting this year's ceremony on Wednesday, October 15th in Boston, strategically scheduled right before ClioCon and at Suffolk Law School where I teach. As I shared with Bob, the awards began during the pandemic as a way to bring our community together and recognize exceptional work in legal technology. I'm incredibly thankful to my co-founders Cat Moon, a professor at Vanderbilt Law School, and Patrick Palace, who runs a personal injury and workers' compensation practice in Tacoma, Washington.
Together, we've created a platform to celebrate innovation across multiple categories including journalism, startups, lifetime achievement, access to justice, courts, and education. What started as a virtual gathering (our first two years were fully online due to COVID) has evolved into a meaningful in-person celebration that's become a fixture in the legal tech calendar.
Each year, we see growth not just in the number of nominations but in the caliber of innovators being recognized. As I mentioned to Bob, the awards didn't begin with grand intentions, we simply wanted to bring friends together and acknowledge the positive impact of legal technology. Some might dismiss us as "just a bunch of do-gooders," but I wear that badge proudly.
We're trying to make a difference in the legal world, and these awards help shine a spotlight on those efforts. The nomination process is open now, and we welcome self-nominations with no fee required (the only charge is for attending the dinner itself). And as Bob humorously pointed out, if nothing else, attendees can look forward to seeing what flamboyant outfit Patrick Palace will be wearing this year! The awards represent the collaborative spirit that makes the legal tech community special, bringing together diverse perspectives united by a common goal of improving legal services through innovation.
What's Next?
Bob asked what's next, and honestly, I'm just enjoying bringing people together around legal innovation. I'm working on a book about implementing AI in law firms and business more broadly, and you can expect more events that let us learn, enjoy each other's company, and go out in the world to do good.
And yes, there will definitely be more punk and goth musical interludes. As I told Bob, it's not just about the music, it's a frame of mind about not taking things for granted, being curious, being rebellious and practicing what I call “healthy anarchy,” and getting into some "good trouble."
Thanks to Bob for the great conversation, and to everyone who tuned in to listen. Here's to making legal services more accessible and more human through technology!
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Cheers,
Tom Martin
CEO and Founder, LawDroid
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