If you want to understand how empathy, storytelling, and technology can converge to make legal services accessible to people who need them most, you need to listen to this episode. Jonathan is at the forefront of access-to-justice innovation and brings a decade of hard-won, on-the-ground experience to this conversation.

Turning Empathy Into Access: How Upsolve Is Rewriting the Rules of Bankruptcy Law

Join me as I interview Jonathan Petts, co-founder and CEO of Upsolve.

In this insightful podcast episode, Jonathan shares his journey from the Upper East Side of Manhattan to the clerk’s offices of Brooklyn bankruptcy court , and ultimately to building one of the most impactful legal tech nonprofits in the country. He dives deep into how Upsolve has evolved from a manual spreadsheet operation into an AI-powered platform that helped 115% more people get a fresh financial start last year alone. Jonathan also walks us through how their AI Paralegal tool is deflecting 50% of support questions and enabling each paralegal to serve four times the number of people they once could.

His stories and insights reveal what it truly takes to close the access-to-justice gap, not with theory, but with practical, iterative, deeply human-centered design. This episode is a must-watch for anyone who believes that technology should serve people first, offering a powerful model for what legal innovation looks like when empathy leads the way.

The Skinny

Jonathan Petts, co-founder and CEO of Upsolve, has spent the last decade building what he describes as a “TurboTax for bankruptcy” for low-income Americans who can’t afford lawyers. In this conversation, Jonathan traces his path from growing up on Manhattan’s Upper East Side, shaped by an English father who prized education and a California mother who modeled social ease, through an English degree at the University of Pennsylvania, to law school and a pivotal summer interning in a Brooklyn bankruptcy court clerk’s office during the chaotic lead-up to the 2005 bankruptcy law reform. That experience, watching overwhelmed people wade through 100 pages of dense legalese with Staples-bought form packets, left him both inspired and angry at how unnecessarily hard the system made it to access a constitutional right. After being let go from two large law firms, Jonathan found his footing by returning to serve, eventually co-founding Upsolve with Harvard undergrad Rohan Pavluri after a chance meeting at a pro bono lunch. A Y Combinator alum, Upsolve has now helped thousands find a fresh financial start, and with the addition of an AI Paralegal tool, the organization saw the number of people each paralegal could serve quadruple last year, with users of the AI finishing the process at three times the rate of those who don’t use it.

Key Takeaways:

• Upsolve’s AI Paralegal tool now deflects approximately 50% of questions that previously required human paralegal response, allowing staff to serve dramatically more people

• Users who engage with the AI Paralegal complete the bankruptcy filing process at a three times higher rate than those who don’t

• Last year, U.S. bankruptcy filings rose 15%, but the number of people Upsolve helped get a fresh start rose 115%, a gap largely attributed to the AI tool and operational improvements

• Jonathan’s formative experience in a Brooklyn bankruptcy court clerk’s office during the 2005 reform period revealed the human cost of bureaucratic complexity and set him on his mission

• The AI Paralegal is context-aware, it understands where a user is in the filing process and tailors its responses accordingly, making support feel less like a chatbot and more like a knowledgeable guide

• Jonathan’s advice to new legal tech builders: think carefully about distribution from day one, because building a solution is now easier than ever, but getting it into the hands of people who need it remains the hardest challenge

• Focus beats expansion: when Upsolve tried to expand to immigration and debt lawsuits simultaneously, their core bankruptcy service suffered, a reminder that doing one thing well is harder than it looks

• Jonathan is candid about his own struggles with work-life balance as a founder with two young daughters, and is planning a three-month sabbatical to mark Upsolve’s 10-year anniversary this summer

Notable Quotes:

1. “We have 56,000 people each year who start this tool and don’t get to the end of it. Part of the reason is because they can’t get the support they need.” - Jonathan Petts (00:01:44-00:01:58)

2. “People that use the AI are finishing at a three times higher rate. All of that gives us a lot of conviction that this AI tool to empower folks to unblock themselves is a really high leverage way to increase access.” - Jonathan Petts (00:06:32-00:06:49)

3. “Why is it so hard? Why do you have to fill out 100 pages of dense legalese in order to access this legal process that’s guaranteed by the Constitution?” - Jonathan Petts (00:18:39-00:18:47)

4. “These forms were designed by well-intentioned experts, but those experts weren’t talking to the folks that I was talking to in Brooklyn who couldn’t afford lawyers. And they weren’t designed with those folks in mind. And that, I believe, is the cardinal sin of so much of our consumer legal system in the U.S.” - Jonathan Petts (00:18:51-00:19:23)

5. “When you have no confidence, the thing to do is to find someone you can serve because service connects you with everything you have to give. And that builds confidence.” - Jonathan Petts (00:21:24-00:21:37)

6. “It’s never been easier to create useful solutions and never been cheaper. And the question is, are you going to be able to get that solution in the hands of the people that need it?” - Jonathan Petts (00:28:33-00:28:45)

7. “Building one good access to justice tool — if it’s not getting better, it’s getting worse. That’s a big learning for me.” - Jonathan Petts (00:32:55-00:33:05)

8. “Every day or every other day, I’ll wake up to a new Google review from someone who I’ve never met, in who knows what part of the country, that talks about how Upsolve guided them through one of the darkest times of their life to a better future.” - Jonathan Petts (00:35:18-00:35:32)

Clips

The Cardinal Sin of Legal Design

Built a Non-Profit TurboTax

AI Tripled Completion Rates

YC Forced Us to Think Big

Jonathan’s story is ultimately a story about what happens when you design legal tools for the people who actually need them. From spending a summer watching desperate filers wrestle with $29.99 Staples packets to building an AI-powered platform that quadruples paralegal capacity, he has never lost sight of the human being on the other end of the process. His approach, start by doing things that don’t scale, learn deeply, then build, is as applicable to legal innovation as it is to any startup.

What stands out most is Jonathan’s insistence on focus. The temptation to expand Upsolve’s model to other legal domains was real, and the pilot revealed a hard truth: doing two things at once can make both worse. That discipline, staying close to the mission, improving incrementally, and letting the impact compound, is what has allowed Upsolve to outpace the rising tide of financial distress in this country and actually move the needle for real people.

Closing Thoughts

Jonathan’s journey is one that I find genuinely moving. He didn’t start from a place of certainty, he was fired from two law firms, told he shouldn’t be a lawyer, and had to rebuild his sense of purpose from scratch. What he found when he returned to serving people was something we talk about a lot in the Legal Rebels community: that the legal profession, at its best, is a calling to help people through their hardest moments.

What strikes me about Upsolve’s AI Paralegal isn’t just the impressive numbers: 50% question deflection, a 3x completion rate, paralegals serving four times as many people. It’s what those numbers represent: real families who got a fresh start because someone decided that the bureaucratic complexity of our legal system wasn’t acceptable, and then built something to fix it.

For those of us building in legal tech, Jonathan’s story is both a challenge and an invitation. The tools have never been more powerful. The access-to-justice gap has never been more visible. And the model Upsolve has pioneered, empathetic design, iterative improvement, ruthless focus, is one any of us can apply in our own corner of the profession.

The future of legal services belongs to those who keep the human being at the center of everything they build. Jonathan Petts and the Upsolve team are showing us exactly what that looks like.

LAST CHANCE! — the LawDroid AI Conference 2026 starts tomorrow: April 28–29, virtual, and completely free — two days of keynotes, panels, and workshops on AI and the legal profession. I’d love to see you there.

Register Now!

Next week, on April 28 and 29, I’m hosting the LawDroid AI Conference 2026, and I want you there!

This is the third year we’ve done this, and every year I’m amazed by the community that shows up. Lawyers, legal aid advocates, court innovators, technologists, professors, and people who simply refuse to be left behind by the changes happening all around us.

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This year’s theme is The Year to Build, and the agenda reflects that. We have three keynotes from Bridget McCormack, Ron Flagg, and Nikki Shaver. We have panels on ethics, journalism, access to justice, courts, education, and the practice of law. And on Day 2, we have a full slate of hands-on workshops covering skills engineering, vibe coding, document automation, context engineering, and AI agents.

It’s free. It’s virtual. It’s two days you can attend from anywhere in the world, picking the sessions that matter most to you.

Over 1,000 people have already registered. If you’ve been reading this newsletter, you already know why this matters. Come join the conversation.

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See you next week!

Tom Martin

CEO & Founder & Host, LawDroid AI Conference 2026

P.S. - It will be recorded, but you need to register to get access to the recordings.

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If you want to understand how experiential learning can transform the way lawyers think about AI, and why automation bias is one of the most urgent issues facing today’s legal profession, you need to listen to this episode. David is at the forefront of legal technology education and brings a uniquely hands-on, human-centered perspective to how we prepare lawyers for an AI-driven world.

Shaping the Next Generation of AI-Aware Lawyers Through Experiential Learning

Join me as I interview David Colarusso, Practitioner in Residence and co-director of the Legal Innovation and Technology Lab (LIT Lab) at Suffolk University Law School.

In this insightful podcast episode, David shares his remarkable journey from growing up near White Sands in New Mexico, to designing a custom interdisciplinary major at Cornell, to teaching physics with six million YouTube views, to becoming a public defender, data scientist, and now one of legal education’s most inventive minds. He dives deep into how he uses experiential learning, including a brilliantly designed classroom simulation, to teach law students about automation bias and the hidden dangers of over-relying on AI tools.

His stories and insights underscore the critical importance of helping lawyers understand not just how to use AI, but when to question it. This episode is a must-watch for anyone curious about legal education, access to justice, and the human skills that will define the lawyers of tomorrow.

The Skinny

David Colarusso, Practitioner in Residence and co-director of the LIT Lab at Suffolk University Law School, brings one of the most unconventional and intellectually rich backgrounds in legal tech education. A self-described perpetual learner who went from “nature’s laws to people’s laws,” David designed his own major at Cornell combining physics and film, earned a master’s from Harvard’s Graduate School of Education, built a following of over six million YouTube viewers with physics explainer videos, and became a Fulbright exchange teacher in Scotland before ultimately going to law school and serving as a public defender in Massachusetts. It was during his time at the Public Defenders Office, where a massive drug lab scandal forced his entire office to manually search paper files for a chemist’s signature, that David recognized how technology could transform the way the legal system handles data. That insight led him to become the office’s data scientist, then to an adjunct role at Suffolk, and eventually to his current position leading the LIT Lab. In this episode, David walks us through a vivid classroom experiment in which he tricked law students into experiencing automation bias firsthand, revealing how quickly humans learn to over-trust AI tools, and how dangerous that trust can become when those tools fail in ways users don’t anticipate.

Key Takeaways:

• Automation bias, the tendency to over-rely on AI decision tools, is a real and measurable phenomenon that affects even attentive, well-intentioned users, as David’s classroom simulation powerfully demonstrated

• David designed a doc review simulation where students worked with an AI tool that was 100% accurate in early rounds, causing them to stop double-checking, and then performed significantly worse when the tool’s accuracy dropped in later rounds

• Experiential learning is David’s pedagogical superpower: rather than lecturing students about AI risks, he creates simulations that allow students to discover those risks themselves

• David’s path from physics teacher to public defender to data scientist to law professor illustrates the value of interdisciplinary thinking in addressing legal technology challenges

• The Massachusetts drug lab scandal, in which chemist Annie Dookhan falsified thousands of drug tests, became a formative moment that revealed how the legal system’s data practices were woefully inadequate

• Suffolk’s LIT Lab focuses on public interest law and access to justice, building tools that serve real people facing real legal challenges

• David draws a sharp distinction between “access to justice” and “access to an attorney”; technology can expand legal access in ways that don’t always require a lawyer

• Students at the LIT Lab build tools that go out into the world and serve real people, meaning their education creates direct public benefit

• The future of legal employment isn’t just about big law; the majority of attorneys in the U.S. work in smaller, solo, or public interest settings, and those contexts may benefit most from AI

• Work-life balance for David means choosing an intentional life: watercolor painting, poetry, walks, and a deep commitment to the examined life, values he absorbed from living abroad in Scotland

Notable Quotes:

1. “I sort of walked in. I was like, you don’t really know who I am... I’m going to ask you first off to just sit down and we’re going to spend 20 minutes doing doc review.” - David Colarusso (00:03:09-00:03:18)

2. “Almost all of them fell victim to something. It’s called automation bias. And so this was a way that I was able to sort of teach them about that, but without having to just say it to them.” - David Colarusso (00:04:48-00:04:55)

3. “They learned to trust the tool, and then the regime in which the tool performed the way they thought it did shifted. And they did not reevaluate their assessment of the tool. And so became over-reliant on it to a detriment to their accuracy.” - David Colarusso (00:08:23-00:08:37)

4. “The problem with a lot of these tools is they sort of upset our traditional signals for what represents quality.” - David Colarusso (00:11:02-00:11:08)

5. “I thought I was simplifying my life... And so that ended up with me becoming the data scientist at the Public Defenders here in Massachusetts.” - David Colarusso (00:32:11-00:32:25)

6. “I don’t want to make the mistake of thinking that access to justice means access to an attorney. In fact, some of the tools we make recognize that that’s not always the case.” - David Colarusso (00:34:57-00:35:05)

7. “I went from nature’s laws to people’s laws. And one of the things that’s nice about people’s laws is unlike nature’s laws... our laws are not set in stone. They’re not the weather. We can do something about them. They’re aspirational.” - David Colarusso (00:39:27-00:39:46)

8. “It mostly is my students, right? I’ve been a teacher in many different guises, and being able to interact with people and help them to sort of lead that examined life and to question what it is they want to do and how it is they want to look at the world and give them a tool set they can use when they go out into the world to make the impact they want to make.” - David Colarusso (00:38:34-00:38:55)

Clips

I Built My Own Major

The “Jagged Edge” of AI

You Aren’t Immune to AI Bias

Growing Up With Missile Tests

David’s classroom simulation on automation bias is more than a clever teaching exercise, it is a microcosm of one of the most pressing challenges facing the legal profession today. When students learned to trust an AI tool that was perfectly reliable, they stopped verifying its outputs. When that tool then failed in subtle ways, they performed worse than they would have without any AI assistance at all. This pattern—trust, reliance, reduced vigilance, degraded performance—is not unique to law students. It is the default human response to any decision-support tool, and it will play out in courtrooms, law offices, and regulatory agencies unless lawyers are deliberately trained to guard against it.

What makes David’s approach so compelling is that he doesn’t just warn students about these risks: he lets them live them. The pedagogical philosophy behind the LIT Lab is grounded in the idea that experiential learning changes people in ways that lectures simply cannot. When students build tools that go out into the world and serve real clients, they develop not just technical competence but moral accountability. That combination, technical literacy plus human judgment, is exactly what the legal profession needs most right now.

Closing Thoughts

Conversations like this one remind me of why I started LawDroid in the first place. David Colarusso represents something rare in legal education: a true polymath who has lived across multiple worlds (physics, film, public defense, data science, and now law school teaching) and brought the lessons of each one into his work with students. His automation bias simulation is one of the most elegant pieces of legal pedagogy I’ve come across, because it doesn’t just teach a concept. It makes students feel it.

What strikes me most is David’s underlying conviction that the law is aspirational. Unlike the laws of physics, which simply describe a universe we didn’t choose, our legal system is something we actively construct and can change. That perspective, hopeful, humanistic, and grounded in real public service, is exactly the kind of energy we need shaping the next generation of legal technologists.

For our Legal Rebels community, the lesson here is not to fear AI, but to approach it with clear eyes. Understanding where your tools work well, where they struggle, and when to question their outputs is not a technical skill, it’s a professional one. David is helping law students develop that skill before they step into practice. The rest of us need to keep developing it too.

If you found this article useful, you’ll love the LawDroid AI Conference 2026. April 28–29, virtual, and completely free — two days of keynotes, panels, and workshops on AI and the legal profession. I’d love to see you there.

Who chooses the problem we’re solving today?

You can build the most powerful search engine ever created, but someone still has to type in the query. You can build an AI that drafts a brilliant legal memo in seconds, but someone still has to decide that this memo, on this issue, for this client, is the thing that needs drafting right now, and not the forty-seven other things competing for attention.

We’ve spent the last three years getting very excited about AI’s ability to solve problems. We’ve spent almost no time asking who decides which problems get solved. And that silence tells you something about a profession that has, for too long, confused doing legal work with solving legal problems.

I call this the Selection Problem: the irreducibly human act of looking at the full landscape of possible problems and deciding which ones deserve our finite attention, resources, and care. It is, I believe, the domain where lawyers will create the most value in an AI-augmented world, and it is the domain that AI is least equipped to occupy.

If this sounds interesting to you, please read on…

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.

The Objective Function

Here’s a concept from the world of algorithms that I think illuminates everything. When engineers build a system to find the “best” answer to a problem, they first have to define what “best” means. They write what’s called an objective function: a set of instructions that tells the system what to aim for. Minimize cost. Maximize speed. Find the shortest route. Each goal produces a different answer, and the system will faithfully pursue whichever goal you set. But, and this is the critical part, the system never chooses the goal for itself.

Want the cheapest solution? The system will find it. Want the fastest? It’ll find that too. But it will never look at your situation and say, “Actually, you’re optimizing for the wrong thing. Cost isn’t your real problem here.” That judgment, the act of deciding what matters, always comes from outside the system. Always.

A logistics AI doesn’t wake up one morning and conclude that carbon emissions matter more than delivery speed. A legal AI doesn’t decide that a client’s emotional wellbeing should outweigh the letter of the contract. Those are value judgments, and value judgments live upstream of computation.

Now, to be fair, AI has become remarkably good at creating structure from unstructured information. Hand it a pile of disorganized client documents, contradictory witness statements, or a sprawling regulatory landscape, and it will impose order. It will categorize, cluster, summarize, and surface patterns you might have missed. That is genuinely valuable, and it would be dishonest to pretend otherwise.

But structuring information is not the same as deciding which structures matter. AI can organize the mess on your desk into neat piles. It cannot tell you which pile represents the problem your client is afraid to name, or which pile contains the seeds of a crisis that hasn’t yet become visible. It doesn’t know what counts as a problem because “what counts as a problem” is a function of human values and worry, fear, sleepless nights, shame, but also institutional priorities, and contextual judgment, not data patterns.

The gap is between structured and what’s worth solving.

The Myth of the Liberated Lawyer

You’ve heard the pitch a hundred times. AI will handle the drudge work, the document review, the research, the first drafts. You’ll be free to “think more strategically.” You’ll “practice at the top of your license.” The tedious stuff drops away, and what remains is the good stuff: the high-level judgment, the creative strategy, the work you went to law school to do.

I want to take this claim seriously, because I think it contains a genuine insight buried inside a significant blind spot.

The insight is real: AI does, in fact, liberate time. When a task that took forty hours takes four, something has to fill the remaining thirty-six. And the optimistic case is that lawyers fill it with higher-order thinking.

The blind spot is: “think more strategically” is not a self-executing instruction. Strategy doesn’t simply appear when you clear calendar space for it. Strategy begins with problem identification, the act of surveying a complex, ambiguous, often contradictory landscape and deciding what the actual problem is. Not the obvious problem. Not the problem the client thinks they have. The real one.

And here is where the profession needs to have an honest conversation with itself. For too long, we’ve defined lawyers by their outputs: wills drafted, contracts reviewed, motions filed. We’ve treated legal work as a series of tasks to be completed, turning lawyers into, frankly, task rabbits. But the definition of a lawyer has never been “a person who produces legal documents.” A lawyer is a person who identifies and solves legal problems. The document is an artifact of the solution; it is not the solution itself.

When we reduce lawyering to task completion, we hand AI its easiest possible victory. Of course a machine can draft a will. The question was never whether it could produce a document. The question is whether it can sit across from a grieving widow, understand the family dynamics she’s too proud to articulate, and recognize that the real problem isn’t the will at all; it’s the estranged son and the business succession plan nobody wants to discuss. That’s problem identification. That’s lawyering.

Consider a general counsel with fifty matters on her desk. AI can help with every single one of them. It can draft motions, summarize contracts, flag regulatory changes, analyze discovery. But it cannot tell her which five of those fifty matters actually threaten the company’s strategic position. It cannot weigh the CEO’s appetite for risk against the board’s tolerance for ambiguity against the competitive dynamics of a shifting market. It cannot feel the political undercurrent in the organization that makes one seemingly minor compliance issue a powder keg and another a non-event.

Those are selection problems. And they require a human being standing in the middle of the mess, accountable for the consequences.

The Multiplication Paradox

Here is where the Selection Problem gets harder, not easier, with better AI.

Consider what happens when AI gets dramatically better at solving problems. Every task that used to take a team of associates a week now takes an afternoon. Contract review that consumed months of junior lawyer time happens in hours. Regulatory analysis across twelve jurisdictions, something that would have been a major staffing decision, becomes a Tuesday morning prompt.

This sounds like liberation. It is, in fact, a multiplication of the Selection Problem.

When your capacity to solve problems expands by an order of magnitude, the number of problems you could solve expands with it. That general counsel who had fifty matters on her desk? Now she can meaningfully act on all fifty. But she still has the same number of hours, the same budget, and the same board with the same risk tolerance. AI didn’t reduce the number of decisions she has to make; it increased them. Every problem that was previously too expensive to touch is now within reach, which means every one of them demands a selection decision that didn’t exist before.

A law firm that once had to triage aggressively because capacity was scarce now faces a different kind of scarcity: the judgment to know which of its newly solvable problems actually deserve solving. A legal aid organization that can suddenly process ten times the inquiries now confronts a question it used to answer by default through resource constraints: which of these clients’ problems do we prioritize when we can technically help all of them?

More capability, more choices. More choices, more consequential selection. The resource allocation question, who gets our finite attention, our finite hours, our finite best thinking, doesn’t get answered by better AI. It gets amplified by it.

And the counterargument, that AI will eventually learn to select problems through preference learning or value alignment, misses the point. Even if an AI could perfectly model a firm’s stated values and a client’s expressed preferences, it would still be optimizing against an objective function that someone had to define. The recursive problem remains: who decides what the AI should value? Who writes the function that tells the machine which problems are worth its attention? That’s still a human standing in the gap, making a judgment call, bearing the consequences.

The Selection Problem doesn’t shrink as AI improves. It grows.

The Exposed Gap

If the Selection Problem is as important as I’ve argued, you would expect the legal profession to have spent decades cultivating it. Training it. Rewarding it. Building institutions around it.

We haven’t.

Here’s what actually happened: AI didn’t create the Selection Problem. It exposed a gap that was already there. For decades, the economics of legal practice allowed us to avoid confronting it. When the billable hour was king, there was no incentive to ask whether a problem was worth solving; there was only an incentive to solve it and bill for the time. When task volume was the measure of a practice, selection was a luxury. You did the work in front of you. You didn’t ask whether it was the right work.

Law schools don’t teach problem selection. They teach issue spotting, which is not the same thing. Issue spotting is a bounded exercise: here is a fact pattern, find the legal issues. Problem selection is unbounded and human-centered: here is a client, a community, an institution embedded in a web of human relationships and competing pressures. What, among everything that could be a legal problem here, actually is one? And among those, which ones matter most?

The profession never built this muscle at scale because the old economic model didn’t require it. Task completion was profitable. Document production was measurable. Problem selection was invisible, done informally by senior partners with good instincts, never codified, rarely taught, impossible to bill for directly.

Now AI is stripping away the task layer. The work that used to fill our days and justify our billing is increasingly handled by machines. And what’s left, what AI cannot do, is the Selection Problem. The thing we should have been training for all along.

This is not a story about AI’s limitations. This is a story about ours. And it leaves us with a single, direct challenge: when the task work disappears, what remains underneath it?

Closing Thoughts

I started with a simple question: who decides what is worth solving? The answer, it turns out, is more revealing than I expected.

AI is the most powerful problem-solving engine humanity has ever built. It can draft, research, analyze, and synthesize faster and more reliably than any team of lawyers. And as it gets better, it doesn’t solve the Selection Problem; it makes the Selection Problem bigger, more urgent, more consequential. Every new capability is another fork in the road that requires a human being to choose a direction.

The profession’s future doesn’t belong to the lawyers who learn to use AI most efficiently. It belongs to the ones who can stand in a room full of newly solvable problems and say: this is the one that matters. Not that one. Not those. This one. And here’s why, and I’ll own the consequences of being wrong.

We’ve been task rabbits long enough. The machines are here for the tasks.

It’s time to choose wisely.

If you found this article useful, you’ll love the LawDroid AI Conference 2026. April 28–29, virtual, and completely free — two days of keynotes, panels, and workshops on AI and the legal profession. I’d love to see you there.

Register Now!

If you want to understand how a bias toward action — not endless deliberation — is what actually moves the needle on access to justice, you need to listen to this episode. Sam is at the forefront of legal innovation and brings a rare combination of practitioner experience, entrepreneurial grit, and systems-level thinking to the challenge of making justice work better for everyone.

From Courtroom to Code: How One Lawyer Decided to Build the Tools Justice Needed

Join me as I interview Sam Harden, Innovation Strategist at Affinity Consulting Group.

In this insightful podcast episode, Sam shares his winding path from Birmingham, Alabama to the forefront of legal technology — from teaching himself Python to build a court date search tool, to lobbying for criminal justice data reform, to helping legal aid organizations and law firms harness the power of AI. He dives deep into what he calls “Law Town,” a provocative vision of a future where lawyers supervise AI agents handling routine tasks so they can focus on what actually matters: counseling, advocacy, and human connection.

His stories and insights underscore a powerful philosophy — that the justice system is an ecosystem, and that small, well-placed interventions can ripple outward in ways that change lives. This episode is a must-listen for anyone who believes technology has a role to play in closing the justice gap, and wants a pragmatic, honest take on where AI can help and where the hard work still falls to us.

The Skinny

Sam Harden, Innovation Strategist at Affinity Consulting Group, brings a rare résumé to the legal tech world: criminal defense lawyer, self-taught coder, legal analytics entrepreneur, access-to-justice advocate, lobbyist, and now consultant to law firms and legal aid organizations navigating the AI era. Raised in Birmingham, Alabama by a family of pharmacists, Sam found his way to law through a passion for advocacy and a desire to push for justice in whatever form that took. His pivot away from trial law came not from a lack of passion but from burnout — and led him to build courtdatesearch.com, a tool designed to prevent the cascading spiral that a single missed court date can set off for vulnerable defendants. Throughout the conversation, Sam articulates a clear-eyed view of AI’s potential: it has made many things cheap and fast, but the hard problems — organizational culture, siloed law firms, human capacity constraints at legal aid organizations — remain stubbornly hard. His “Law Town” concept imagines lawyers as supervisors of their own AI workforce, freeing them to deliver the counseling and advocacy that no algorithm can replicate. Sam’s north star is simple: if the justice system is better ten years from now, it was worth it.

Key Takeaways:

• Sam’s “bias toward action” philosophy — being on “Team Do Something” rather than “Team Commission a Study” — has driven every chapter of his career, from building his first legal tech tool to advocating for criminal justice data reform

• A single missed court date can trigger a devastating spiral: warrant issued, arrest, job loss, eviction. Sam built courtdatesearch.com specifically to interrupt that chain of consequences for vulnerable defendants

• The justice system functions like an ecosystem, where small, targeted interventions, like reintroducing wolves to Yellowstone, can produce outsized, lasting change

• Legal aid organizations are not resource-limited in motivation or talent; they are human-capacity limited, and AI represents a genuine opportunity to extend their reach

• AI has made many legal tasks fast and cheap, but the hard organizational problems, siloed law firms, broken workflows, institutional resistance, are not solved by flipping the AI switch

• Sam’s “Law Town” concept envisions lawyers as supervisors of AI agent teams, offloading rote tasks like document review so they can focus on counseling, advocacy, and client relationships

• The greatest risk of AI in law is that lawyers become rubber-stampers, automating the drudgery without reclaiming the work that actually matters

• Work-life balance in the AI era is genuinely difficult; keeping up with the pace of change often means sleepless nights, and Sam is refreshingly honest about that struggle

Notable Quotes:

1. “If a problem is really bad and everybody agrees that the problem is bad, the best thing to do is do something. I’m on team do something. I’m not on team let’s talk about it, let’s commission a study and then write a report and then not do anything.” - Sam Harden (04:28-04:51)

2. “What if there was an easy way for people to just put in their name or their case number and check their upcoming court date? People are getting mailed a summons to court. A lot of people in the criminal justice system don’t have a fixed address.” - Sam Harden (20:52-21:12)

3. “You may start out with a driving while license suspended case. You don’t show up for your hearing, so the judge issues a warrant. And if you get pulled over, you go to jail. And while you’re waiting in jail, the job that you were working is going, where is this person?” - Sam Harden (23:05-23:35)

4. “I think the justice system is kind of like an ecosystem where small changes can have big impact years later. That’s kind of where I hope I have an impact — figuring out where I can push and where I can pull in the justice ecosystem to make it better.” - Sam Harden (46:07-46:29)

5. “AI has made a lot of things cheap. The hard things still are hard. You can automate a ton of stuff now, but figuring out how the pieces fit together is still really hard. And it takes time, it takes effort, and it takes experimentation, frankly.” - Sam Harden (34:53-37:49)

6. “The practice of law is the counseling, is the advocacy, is the handholding, is the talking to the client, making the client understand their options, being that personal helper for people.” - Sam Harden (39:39-39:54)

7. “Could a lawyer take all of the things that they don’t want to do — the rote document review — and have an AI agent run their playbook? And then the lawyer takes that and goes to the client and says, here’s how I would counsel you. And instead of charging by the hour for that, maybe it’s a different kind of value delivery.” - Sam Harden (40:07-41:09)

8. “The thing that makes it worth it to me is feeling like I’m having some sort of impact on the delivery of justice. If the justice system is better ten years from now, I’m happy.” - Sam Harden (45:04-46:35)

Clips

AI’s Hallucinated Case Law

AI Won’t Fix Lawyer Fiefdoms

Bias Towards Action

AI Can Draft Court Pleadings Now

Sam Harden’s career is a case study in what it looks like to take justice personally — not just as a professional obligation, but as a design challenge. His court date search tool didn’t change the law; it changed the information flow, and that was enough to interrupt a cycle of harm for people who had no other lifeline. That is systems thinking applied with humanity, and it is exactly the kind of ingenuity the legal sector needs more of.

What I find most compelling about Sam’s perspective is his refusal to be either a techno-utopian or a skeptic. He has used Claude Code, tested Google’s agentic tools, worked inside legal aid organizations, and consulted with law firms — and his conclusion is nuanced: AI lowers the floor on what’s possible, but raises the stakes for getting the organizational and human factors right. The “Law Town” vision is not a fantasy of lawyers replaced by robots. It is a vision of lawyers finally freed to do the work that only humans can do.

Closing Thoughts

Conversations like this one remind me why I started LawDroid in the first place. Sam Harden is not a theorist, he is someone who saw a problem, taught himself to code, and built something. The fact that courtdatesearch.com made zero dollars and still found its way onto the county clerk’s own website is exactly the kind of story I want our Legal Rebels community to carry with them. Impact doesn’t always look like a unicorn startup.

What strikes me most about Sam is his clarity about where AI fits and where it doesn’t. He is not selling a silver bullet. He is doing the hard, unglamorous work of helping organizations figure out how to actually use these tools, not just adopt them in name. That distinction matters enormously as our profession navigates what may be the most consequential technological shift in the history of law.

The “Law Town” framework is one I think every lawyer should sit with. Ask yourself: what are the things in my practice that I wish I never had to do again? Those are your candidates for automation. Now ask: what are the things I do that no AI can replicate — the moments where a client needs a human being who understands their situation, their fear, their options? That is your value. Protect it. Build toward it.

Sam’s north star — a justice system that is measurably better a decade from now — is one I share. I believe technology is one of the most powerful levers we have to get there. But as Sam makes clear, the lever only works if the people pulling it are thoughtful, honest, and relentlessly biased toward action.

In this month’s AI Double Take, LawDroid CEO Tom Martin and Chief Legal Futurist Sateesh Nori tackle a packed April in AI, from a surprising generational divide in attitudes toward AI, to the accidental leak of Anthropic’s Claude Code codebase, Google’s powerful open-source Gemma 4 release, and the rise of the first AI-powered solo billion-dollar company. The hosts debate whether AI should be regulated as a public utility, what the telehealth startup model could mean for legal access to justice, and why, despite the turbulence, both remain convinced the best is still ahead.

Key Takeaways

1. The Generational Divide — Gen Z vs. Gen X on AI

Counter to expectations, it’s Gen Z — not older generations — who are most resistant to AI in the workplace. Having grown up in a surveillance state, experienced social media’s harms firsthand, and come of age amid constant digital scrutiny, Gen Z brings deep skepticism to new tech. Gen X, by contrast, remembers the “before” — typewriters, microfiche, physical courthouse trips — and sees AI as liberation. The takeaway: the same technology looks entirely different depending on your “before snapshot.”

2. The Claude Code Leak — A Wake-Up Call

Around April Fool’s Day, Anthropic accidentally leaked the Claude Code codebase — including what appeared to be a pre-release model called “Mythos.” Key observations: (1) it can happen to anyone, even a $30B company; (2) the underlying system prompt code was simpler than expected — basic behavioral directives; (3) some instructions told the model to avoid leaving “fingerprints” when crawling for information, raising copyright questions; (4) Anthropic had apparently seeded the codebase with misleading decoy information before the leak. Once out, it spread instantly — the genie couldn’t be put back in the bottle.

3. Google’s Gemma 4 — Open Source Raises the Stakes

Google released Gemma 4, a powerful open-source model under Apache 2.0 licensing — meaning it can be freely copied, modified, and even resold. This puts real pressure on the defensibility of OpenAI’s and Anthropic’s proprietary model businesses, and dramatically expands what developers can build independently.

4. AI as Public Utility — The “Department of Intelligence” Idea

The Claude Code leak triggered a broader debate: should AI be regulated like electricity or water? Sateesh argued for a publicly regulated AI baseline — universally accessible, consistently priced — with private innovation building on top. Tom framed it as a “Department of Intelligence” or public library model: shared intelligence infrastructure that anyone can tap. Both hosts see self-regulation through market competition as insufficient.

5. The Two-Person Billion-Dollar Telehealth Company

A college dropout and his brother built a telehealth company — powered by AI and focused on GLP-1 weight loss drugs — to a $400M first-year revenue and billion-dollar valuation (verified by the New York Times). The model: AI handles scale, humans manage the customer relationship. The question for legal: why can’t this model be replicated for access to justice?

6. The Access to Justice Opportunity — Rethinking the Nonprofit Model

Sateesh challenged the traditional nonprofit legal model, noting that many legal aid organizations function more as jobs programs than delivery systems. With 92% of legal needs going unmet, AI-empowered individuals could scale their impact 10x beyond what a bureaucratic organization can achieve. LawDroid is actively building tools to enable exactly this kind of leverage.

7. Human Judgment + AI = Exponential Impact for Good

Both hosts’ final takes converge on optimism: the telehealth story proves that a single motivated person with practical intelligence and AI tools can create extraordinary impact. The challenge — and the mission — is to point that power toward good. Tom noted the current geopolitical climate as a prerequisite: nothing else can fully flourish until conflict is resolved.

Show Notes

Topics Covered

• Generational divide: Gen Z skepticism vs. Gen X techno-optimism toward AI

• Social media’s long-term impact on Gen Z’s mental health and trust in tech

• Personal anecdote: Tom’s Pixar-style AI photo and his daughter’s reaction

• The accidental Anthropic / Claude Code codebase leak (circa April 1, 2026)

• Leaked reference to a new Anthropic model: “Mythos”

• System prompt simplicity and “no fingerprints” crawling instructions

• Anthropic’s decoy/trap content pre-planted in the codebase

• Google Gemma 4: open-source, Apache 2.0, strong performance

• Competitive defensibility of proprietary AI models

• AI as commodity/utility — the electricity and internet analogies

• Proposal for a publicly regulated AI baseline (”Department of Intelligence”)

• First AI-powered one-person billion-dollar company (telehealth / GLP-1)

• Nonprofit legal aid model critique — the 92% unmet legal need figure

• LawDroid’s mission to empower AI-enabled legal access at scale

People & Organizations Mentioned

• Tom Martin — CEO & Founder, LawDroid

• Sateesh Nori — Chief Legal Futurist, LawDroid

• Ron Flagg — President, Legal Services Corporation (LSC); conference keynote

• Bridget McCormick — Conference keynote speaker

• Nikki Shaver — Conference speaker / thought leader

• Anthropic — AI company; Claude Code leak, “Mythos” pre-release

• Google — Released Gemma 4 (open-source, Apache 2.0)

• OpenAI / ChatGPT — Referenced in competitive defensibility discussion

• Unnamed telehealth founder — College dropout; first AI-powered one-person billion-dollar company (GLP-1 / weight loss drugs, verified by NYT)

Upcoming: LawDroid AI Conference 2026

• Dates: April 28–29, 2026

• Format: Virtual (attend from anywhere)

• Cost: Free

• Theme: The Year to Build

• Keynote speakers: Bridget McCormick (AAA), Ron Flagg (LSC), Nikki Shaver (LegalTech Hub), and more

• MC & Day 2 speaker: Sateesh Nori

• Register at lawdroidaioconference.com

Final Takes

Sateesh Nori:

“We’re already in April 2026, and I still feel like we haven’t crested the mountaintop on what’s coming. I’m with bated breath about what could happen tomorrow, next week, in May and June and beyond — not just in world politics, but in AI and the way our world is going to change, hopefully for the better.”

Tom Martin:

“I really hope the conflict going on right now resolves itself — nothing else can fully happen without that. But assuming it does, knock on wood: we’re at a place where everything seems possible. The telehealth story shows that someone who’s a college dropout can use the intelligence they have, with the aid of AI, to have an amazing impact. If only that were used for good — and I believe it can be — there would be so much more good in the world.”

AI Double Take is produced by LawDroid | lawdroid.com

If you want to understand how human-centered design and conscious self-awareness can help lawyers navigate the AI transformation without losing themselves in the process, you need to listen to this episode. Mia is at the forefront of legal design and AI adoption and brings a uniquely grounded, human-first perspective to one of the most urgent conversations in our profession.

Designing a Human Future for Law in the Age of AI

Join me as I interview Mia Ihamuotila, Legal Tech & Design Lawyer at Castrén & Snellman and Chair at the Legal Design Summit.

In this insightful podcast episode, Mia shares her journey from a childhood rooted in dance and creativity near Helsinki, through her studies in law and legal design, to building a hybrid role that bridges legal practice, design thinking, and AI strategy. She dives deep into her framework for the human-machine symbiosis, arguing that the real risk of AI is lack of intentionality in how we engage with it.

Her stories and insights underscore the importance of self-awareness, process thinking, and mindset in successfully navigating legal transformation. This episode is a must-watch for any lawyer curious about what it truly means to work alongside AI, not just how to use the tools, but how to remain grounded, creative, and deeply human while doing so.

The Skinny

Mia Ihamuotila, Legal Tech & Design Lawyer at Castrén & Snellman and Chair at the Legal Design Summit, shares her remarkable journey from a childhood spent dancing near Helsinki to building one of the most thoughtful and human-centered approaches to legal AI in the profession today. Raised outside the city with deep ties to nature, dance, and creativity, Mia was drawn to law for its power to shape society and its potential for transformation. After early traineeships in legal design with mentor Antti and a formative exchange year studying legal tech in Hong Kong, she wrote her master’s thesis at her current firm, empirically testing how legal design could improve the transparency and understandability of privacy policies. What sets Mia apart is her conviction that the human-machine relationship is not adversarial but symbiotic: that AI has the potential to elevate human thinking if we engage with it consciously, with self-awareness, and through multi-step collaborative processes. Her work now includes AI workshops and transformation consulting for both her firm’s lawyers and their clients, with the Legal Design Summit serving as a global platform to expand this conversation.

Key Takeaways:

• Mia’s path to legal innovation was shaped by a lifelong commitment to dance, creativity, and human connection: qualities she now brings directly into her legal design and AI strategy work

• Her origin story includes early burnout and a period of depression that led her to self-awareness practices like breathwork and meditation, which now form the foundation of her approach to balance and conscious design

• She argues for a symbiosis between human depth and machine breadth, when combined, these two dimensions create an entirely new dimension of capability

• The real risk of AI is not the technology but unconsciousness: the danger arises when people engage with AI without awareness, intention, or a structured process

• Practical AI adoption starts with mindset, not tools, mapping the lawyer skill set to include creativity, data literacy, interdisciplinarity, and design thinking before moving into tool use

• Mia conducts AI and design workshops for both internal lawyers and clients, framing this as a shared transformation journey rather than a one-directional education

• Legal design and legal tech are not separate disciplines: they are complementary life forces that belong under the broader umbrella of legal innovation

• The Legal Design Summit is evolving toward a chapter-based model with country-level ambassadors to maintain a coherent, year-round global community

• Balance is not just work vs. rest, it requires designing your environment around your nervous system’s needs, knowing when you need solitude, creativity, or social engagement

• Mia begins every day with breathwork, meditation, and movement, refusing to engage with the world before first centering herself

Notable Quotes:

1. “I usually talk about the symbiosis or the synthesis between the human and the machine and how it becomes kind of a wavy flow between those two. So it’s not about like man versus machine.” - Mia Ihamuotila (27:34-27:45)

2. “The machine has enormous capability to create breadth... but then as a human we have an immense capability to create depth in things. And I think these two dimensions, when combined, create a new dimension.” - Mia Ihamuotila (27:48-28:18)

3. “I really honestly believe that AI has the potential to elevate our thinking as human beings if we allow it to do so. And I think the tool for that is self-awareness.” - Mia Ihamuotila (28:23-28:36)

4. “I see this as a conscious evolution that is happening.” - Mia Ihamuotila (29:01-29:04)

5. “I don’t see the risks and the fear in there. I think the risk is this unconsciousness—the lack of consciousness in people in that case.” - Mia Ihamuotila (30:56-31:07)

6. “Everything starts from this mindset and the attitude and the mapping of skills, the lawyer skill set.” - Mia Ihamuotila (33:17-33:24)

7. “I don’t want to jump into the waves of the world before saying hi to myself.” - Mia Ihamuotila (44:08-44:14)

8. “I get to do transformation as the main driver in my career. And that’s been the main driver of my personal life forever. So that’s perfect.” - Mia Ihamuotila (46:21-46:35)

Clips

Death, Rebirth, and New Beginnings

Design and Tech: Inseparable Forces

Human-AI Symbiosis

Use Process Thinking Without AI

Mia’s story is a reminder that the legal profession’s transformation is not just technological, it is deeply personal. Her journey from dance studios and burnout to building a hybrid law career grounded in design thinking and conscious AI adoption reflects the kind of inner work that most transformation conversations leave out entirely. She brings to the table something rare: a framework for remaining human not despite the AI revolution, but through it.

What makes her perspective especially compelling is the practical dimension. It’s not enough to talk about consciousness and symbiosis in the abstract. Mia is in law firms, running workshops, mapping skills, and guiding lawyers and clients through the early and middle stages of this transformation, meeting people where they are and building the capacity they need to move forward. Her work at the Legal Design Summit amplifies this further, building a global community of practice that embodies the very transformation it champions.

Closing Thoughts

Talking with Mia was genuinely one of those conversations that changes how I think about what we’re doing in this space. As someone who has been building legal technology for years, I sometimes get caught up in the tools: the capabilities, the models, the use cases. Mia reminded me that the foundation of all of that has to be the human being holding it.

Her concept of conscious engagement with AI is something I want every lawyer in our community to hear. The technology is not the problem and it is not the solution. The quality of our attention, intention, and self-awareness is what determines what we build with it and what it does to us. That’s a profound reframe.

What inspires me most is the way Mia has integrated who she is, dancer, designer, lawyer, meditator, into a coherent whole rather than treating these as separate identities. That kind of integration is, I think, exactly what the profession needs right now. Not lawyers who bolt AI onto existing practice, but lawyers who are willing to grow into a fuller version of themselves and let their work reflect that.

For our Legal Rebels community, Mia’s story is both a challenge and an invitation. The invitation is to approach this transformation consciously, to start with mindset before tools, to design your environment around your nervous system, and to begin the day by saying hi to yourself before jumping into the waves of the world. The challenge is to do that inner work consistently, even when the pace of change makes it tempting to skip it.

The future of law belongs to those who can hold both depth and breadth, who can be fully human while working alongside machines that are becoming more capable by the day. Mia is living proof that this is not only possible but extraordinarily exciting.

We’ve all heard the pitch. Staring at a blank page? Just prompt AI!

In seconds you’ve got a working draft: structured, coherent, surprisingly competent. The blank page problem, that ancient enemy of productivity, has been vanquished.

Except the blank page was never just an obstacle. It was a space of possibility, of roads untraveled. And for lawyers, it was the space where the most important part of our work actually happens.

I call it the First Draft Trap!

The moment you accept an AI-generated draft as your starting point, you’ve already made the most consequential decision of the entire project; and you made it by not making it. You let the machine choose your direction, your framing, your theory. Everything that follows is editing. And editing, no matter how rigorous, is not the same as thinking.

If this sounds interesting to you, read on…

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.

The Cognitive Hijack

There’s solid psychology behind why this happens. Daniel Kahneman and Amos Tversky demonstrated in their landmark 1974 paper, “Judgment under Uncertainty: Heuristics and Biases,” that once people are exposed to an anchor, even a transparently arbitrary one, it distorts their subsequent judgments. In their experiments, subjects who watched a roulette wheel spin to a random number still let that number influence their estimates of completely unrelated quantities. The anchor held even when people knew it was meaningless.

An AI first draft is the most seductive anchor imaginable. It’s not random; it’s plausible. It’s well-organized. It sounds like something a lawyer would write. And that’s precisely what makes it dangerous. You know intellectually that it’s just one of many possible approaches. But the anchor holds anyway. Kahneman would tell you that knowing about the bias doesn’t protect you from it.

There’s an even more precise concept here. In 1942, the psychologist Abraham Luchins identified what he called the Einstellung effect: once a person finds a solution that works, they become functionally blind to better solutions, even when those alternatives are obvious to someone encountering the problem fresh. The first working solution doesn’t merely compete with alternatives. It blocks perception of them entirely.

That’s the First Draft Trap at the pyschological level. The AI draft isn’t just one option you happen to prefer. It’s a cognitive filter that prevents you from seeing the other options that were available to you: the roads you never even noticed you didn’t take.

The Anti-Socratic Method

Now consider what this means for a profession built on the opposite instinct.

From the first day of law school, we’re trained to resist the obvious answer. The Socratic method exists for exactly this reason. A good professor hears your confident response and asks: What else? What if the facts were different? What’s the argument on the other side? The goal isn’t to arrive at an answer. It’s to build the mental habit of holding multiple possibilities in tension before committing to any of them.

The First Draft Trap is the anti-Socratic method. It delivers a confident answer before you’ve even formulated the question properly. And instead of interrogating it, you polish it.

Think about what a senior partner actually does when a junior associate brings a memo. The partner’s value isn’t better writing. It’s peripheral vision: the ability to see what the memo doesn’t address. The argument it didn’t consider. The framing that would land differently with this particular judge or this particular jury. That capacity to see beyond the document in front of you is what clients pay premium rates for. And it’s exactly the muscle that atrophies when your default workflow begins with “generate a draft.”

There’s a direct parallel to case strategy. A litigator who latches onto the first viable theory of the case is a dangerous litigator; dangerous to the client. The great ones hold three or four theories in suspension, stress-test each against the facts, and only then commit. That uncomfortable period of ambiguity, of genuinely not knowing which path is best, is where the real lawyering lives. The AI first draft is the equivalent of committing to a theory of the case before you’ve finished reviewing discovery.

System 1 Hijacks a System 2 Profession

Kahneman’s two-system framework gives us a clean way to describe what’s going wrong. System 1 is fast, intuitive, pattern-matching. System 2 is slow, deliberate, analytical. The practice of law, at its best, is a System 2 discipline. We’re trained to override our gut reactions, challenge assumptions, and think through consequences before acting.

The AI first draft feels like a System 2 output. It’s structured, footnoted, methodical. But your decision to accept it as a starting point is pure System 1: a fast, intuitive grab at the nearest plausible answer. You’ve used a sophisticated tool to bypass the sophisticated thinking the tool was supposed to support.

What to Do Instead

None of this means stop using AI. It means stop using it to skip the part that matters.

Before you ever ask for a draft, ask for the map. Try a prompt like this:

I’m working on [describe the matter, motion, or document]. Before drafting anything, give me:

1. Three fundamentally different strategic framings for this problem.

2. For each framing, the strongest argument in its favor and its most serious vulnerability.

3. Which framing best fits [the client’s goals / the audience / the procedural posture].

Do not write a draft. I want to choose the direction before we start building.

That last line is the key. It keeps you in the driver’s seat during the phase that matters most. You’re using AI to expand the possibility space before you collapse it, not after.

In Kahneman’s terms, use AI to fuel System 2, not to hand the controls to System 1. Let the machine generate options. You exercise judgment. And, also don’t forget to add your own ideas and explore them too!

The blank page was never your enemy.

It was the last place where all possibilities were still alive; where your judgment, your experience, and your capacity to see what others miss had room to operate. The First Draft Trap paves over that space with something that looks like progress but might be the most expensive shortcut you’ve ever taken.

For lawyers, the ability to see what isn’t there is the whole game.

Don’t let the first draft trap blind you to it!

If you found this article useful, you’ll love the LawDroid AI Conference 2026. April 28–29, virtual, and completely free — two days of keynotes, panels, and workshops on AI and the legal profession. I’d love to see you there.

Register Now

If you want to understand how AI is fundamentally disrupting legal client acquisition, why lawyers are getting ripped off by outdated marketing models, and what a scientist-turned-tech-founder sees that most lawyers are missing, you need to listen to this episode. Edward is at the forefront of rethinking how lawyers connect with clients and brings a uniquely cross-disciplinary perspective that cuts through the noise.

Following the Money: How AI Is Rewiring Legal Client Acquisition

Join me as I interview Edward Bukstel, CEO of Giupedi, Inc., a legal client acquisition platform built at the intersection of healthcare data, AI, and access to justice.

In this insightful podcast episode, Edward traces an extraordinary journey: from building one of the first networked electronic health records in 1987, to going toe-to-toe with a pharmaceutical giant over stolen software, to applying that same structural thinking to the crisis quietly unfolding in how lawyers attract and acquire clients. He reveals how Google’s AI overviews are already siphoning 56% of clicks that used to land on law firm websites, and why most lawyers are still paying the same marketing bills with dramatically less to show for it.

His stories and insights expose the mechanics of a broken system, from geofencing hospitals to generate personal injury leads, to the way legal directories like Avvo, FindLaw, and Martindale-Hubbell disproportionately serve high-ROI cases while leaving everyday people with limited legal options with nothing. This episode is a must-watch for anyone who wants to understand what’s really happening beneath the surface of legal AI, and where the real opportunities lie.

The Skinny

Edward Bukstel, CEO of Giupedi, Inc., brings a perspective on legal AI that few in the industry can match. With a background spanning molecular biology, early electronic health records, WebMD, and a personal legal battle against a pharmaceutical company that stole his software, Edward has spent decades seeing how technology intersects with broken systems, and figuring out how to fix them. In this conversation, he maps the structural forces reshaping legal client acquisition: AI overviews eating 56% of law firm web traffic, legal marketing companies charging the same fees while delivering less, and a $14 billion industry built around feeding high-value contingency cases while leaving underserved clients largely invisible. His platform, Giupedi, is built on the insight that the real moment of legal need begins not with a Google search, but at the point of injury: in ERs, urgent care facilities, and clinics. Edward also digs into the Bloomberg GPT effect, the UPL question no one is asking about AI foundational models, and why the legal profession needs to lead on AI adoption before the models do it for them.

Key Takeaways:

• AI overviews are now capturing 56% of clicks that previously went to law firm websites, while marketing companies continue charging the same rates, lawyers are paying more for far less

• Traditional legal SEO and directory-based marketing (FindLaw, Avvo, Martindale-Hubbell) are losing their effectiveness, and most law firms have no in-house marketing director to navigate the shift

• ChatGPT and other LLMs are now a meaningful source of legal referrals, 40% of people who ask an AI for a lawyer recommendation will choose one of the AI’s suggestions, compared to 2–4% conversion under old Google SEO

• The real origin point of a personal injury or workers’ comp legal need is the moment of injury, at the ER or urgent care, not a billboard or a Google search, which is the founding insight behind Giupedi

• The Bloomberg GPT effect demonstrates that more capable base models outperform older models fine-tuned on massive domain-specific datasets, meaning the smartest general model will often beat a “specialized” one trained on more data

• Legal directories like Avvo and FindLaw lavish resources on high-ROI contingency cases while underserved clients, such as tenants facing eviction, are nearly invisible in the same platforms

• If the legal profession doesn’t lead on democratizing AI-assisted legal help, foundational models will fill the gap on their own terms, raising real unauthorized practice of law questions that no one is yet asking

• Edward maintains balance amid nonstop entrepreneurial demands through open-mic comedy, gym time, and the grounding reminder of his two daughters

Notable Quotes:

1. “Lawyers are getting ripped off and there’s a better way to do it.” — Edward Bukstel (08:14-08:17)

2. “56% of the clicks that would normally have gone to a law firm website is now going to an AI overview.” — Edward Bukstel (04:52-05:05)

3. “40% of the time, someone that asked ChatGPT ‘tell me the best personal injury lawyer in Philadelphia’ will make a decision and choose one of the ones recommended by ChatGPT — as opposed to the old Google SEO days where it was maybe 2% and 4% was considered really good.” — Edward Bukstel (07:40-08:07)

4. “The smart lawyer is going to outperform the one that’s not so smart. And that’s what we’re seeing with the models. The most up-to-date models are going to always outperform.” — Edward Bukstel (32:43-32:54)

5. “If you go ahead and take a look in those same directories for folks that are concerned about getting evicted, you don’t even have pictures of lawyers. It’s like, we don’t want you to contact us because we know we’re not going to make any money on you.” — Edward Bukstel (35:36-35:52)

6. “Why haven’t some of the big law firms out there sued these models — not just over copyright issues, but over what really does look like an unauthorized practice of law?” — Edward Bukstel (36:50-37:03)

7. “If we’re not going to provide those same kind of gilded on-ramps and services to folks that really need it with a human lawyer, then why not provide them with an LLM?” — Edward Bukstel (35:59-36:20)

8. “You gotta hit some singles before you go ahead and take that big swing.” — Edward Bukstel (41:05-41:11)

Clips

Lawyers Are Getting Ripped Off

Too Big To Sue

Chat GPT Becomes The New Source of Leads

Lawyers Geofence Hospitals

Edward’s perspective is rare in the legal tech conversation because it comes entirely from outside the legal profession. He’s not a lawyer theorizing about disruption; he’s a builder who has created real systems, fought real battles, and watched real industries get restructured by technology. His analysis of what’s happening in legal client acquisition isn’t speculative; it’s grounded in data he’s actually collected, from website traffic studies to conversion rate comparisons between Google and ChatGPT.

What makes this episode particularly timely is Edward’s attention to the access-to-justice dimension. The same market forces that are enriching legal marketing companies and personal injury firms are systematically underserving the clients who most need help: people facing eviction, workers’ compensation claims, and other legal needs that don’t generate the contingency-fee returns that attract premium directory placement. His argument is simple: if the legal profession won’t close that gap voluntarily, AI will close it anyway.

Closing Thoughts

Conversations like this one remind me why I started LawDroid in the first place. Edward isn’t a lawyer, and that’s exactly what makes his perspective so valuable. He sees the legal industry the way a scientist sees a system: following the structure, following the money, and asking questions that people inside the profession are too close to ask.

The numbers he shared stayed with me. Fifty-six percent of clicks gone to AI overviews. Forty percent of people taking action on an AI’s lawyer recommendation. Billions spent on legal marketing while legal aid organizations beg for a fraction of that to serve the people who need it most. These aren’t abstract trends, they are reshaping the economics of legal practice right now, and most lawyers I talk to still haven’t fully reckoned with what that means.

Edward’s work with Giupedi is a bet that the future of legal client acquisition starts at the point of need, not at a search bar. That’s a structural insight, and structural insights tend to be right. For our Legal Rebels community, the takeaway is clear: the game has changed. The firms that understand where clients are actually coming from, and who build authentic, substantive presence in AI systems, are going to win. Those who keep paying for the old playbook are going to keep getting ripped off.

The access-to-justice piece matters too. AI is going to fill the legal help vacuum whether the profession leads or follows. I’d rather we lead.

If you liked this podcast, you’ll love the LawDroid AI Conference 2026. April 28–29, virtual, and completely free — two days of keynotes, panels, and workshops on AI and the legal profession. I’d love to see you there.

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I’m a fan of Christopher Nolan’s Interstellar. In it, there’s a scene where Cooper and his crew land on Miller’s planet, where the gravitational pull of a nearby black hole distorts time so severely that one hour on the surface equals seven years back on Earth. They spend what feels like minutes collecting data. When they return to the orbiting ship, twenty-three years have passed. Their colleague has aged. Their children have grown up. The world they left behind no longer exists.

We are living through our own version of this time dilation, except nobody gets to stay on the ship.

The gravitational force warping our timeline isn’t a black hole. It’s artificial intelligence. And the distortion isn’t theoretical. It’s measurable in months, not decades. The intervals between transformative capability shifts are compressing so rapidly that our institutions, our industries, and our individual capacity for adaptation are being stretched past their design limits. I call this phenomenon cascading transformations, and I believe it represents the most consequential structural dynamic in technology today, not because of what AI can do, but because of what the rate of AI advancement does to everything around it, including us.

If this sounds interesting to you, please read on…

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.

Cascading Transformations: Everything, Everywhere, All At Once

To understand what cascading transformations are, let’s trace the sequence of events.

In late 2022, OpenAI released ChatGPT. It was a chat interface, a text box and a response. Impressive, novel, but bounded. It didn’t, on its face, look like the kind of thing that should reshape entire industries. It was an ingenious parlor trick.

Then, in 2023, came retrieval-augmented generation and fine-tuned models. Then, in 2024, basic agentic capabilities: AI that could use tools, browse the web, execute multi-step reasoning. Then, in 2025, autonomous agents, capable of planning, adapting, and self-correcting. Then, in 2026, the orchestration of multiple agents working in concert, approximating something that begins to look like an autonomous organization. And threading through all of it, the expansion of context windows, transforming AI from a system that could hold a conversation into an engine that could ingest, synthesize, and reason across vast bodies of information.

We’ve leapt across the five stages of AI evolution in almost a single bound:

• Stage Level 1: Chatbots, AI with conversational language

• Stage Level 2: Reasoners, human-level problem solving

• Stage Level 3: Agents, systems that can take actions

• Stage Level 4: Innovators, AI that can aid in invention

• Stage Level 5: Organizations: AI that can do the work of an organization

Each of these developments, taken individually, looks like a reasonable incremental step. A better model. A new capability. But cascading transformations don’t operate linearly. Each capability multiplies the impact of every capability that came before it.

An agent that can use tools is interesting. An agent that can use tools and reason across a million tokens of context and coordinate with other agents and operate autonomously within defined guardrails, that’s not an incremental improvement. That’s a phase transition. And the evidence is everywhere.

A year ago, Anthropic published research on Claude’s capacity for extended autonomous operation, running for hours without human intervention, navigating complex multi-step workflows. OpenAI announced its Operator agent framework. Google DeepMind’s Gemini models began demonstrating agentic reasoning across modalities. These are tectonic plates shifting in real time.

Meanwhile, the research frontier accelerates independently. Breakthroughs in mixture-of-experts architectures, retrieval-augmented reasoning, reinforcement learning from human feedback, and long-context processing aren’t happening sequentially, they’re happening simultaneously, each one creating downstream butterfly effects that compress the next cycle of innovation further.

When Breathing Room Disappears

In most technological revolutions, there’s breathing room. The printing press took decades to reshape European intellectual life. The internet took roughly fifteen years to move from curiosity to infrastructure. Even the smartphone, which felt fast at the time, gave industries about a decade to adapt from the iPhone’s launch to the mobile-first economy.

With AI, that buffer has evaporated. The distance between “chatbot” and “autonomous organization” is not a decade. It is, by any reasonable assessment, three to four years. And the rate of cascading transformations is not linear; it’s asymptotic. The curve bends sharply toward vertical.

This is where the Interstellar analogy comes in. On Miller’s planet, the crew felt like they had time. The waves looked manageable from a distance. It was only upon return that the devastation of time dilation became apparent. Right now, organizations across every sector are standing on their own version of Miller’s planet. The waves are coming. And every hour of delay costs disproportionately more than the last.

Consider what has already shifted in legal services alone. Three years ago, “AI for law” meant document review automation and basic contract analysis. Today, we’re deploying AI-powered legal information assistants that provide guided access to justice at scale, building autonomous workflows for court systems, and watching the emergence of AI-native legal organizations that operate with a fraction of traditional overhead. The firms and legal aid organizations that moved early aren’t just ahead, they’re operating in a fundamentally different competitive reality than those still deliberating.

The Human Cost of Cascading Transformations

Here is the dimension that receives the least attention and deserves the most: what sustained, accelerating technological disruption does to people.

There is an emerging body of research on what psychologists are beginning to call change fatigue, the cumulative cognitive and emotional toll of continuous adaptation without recovery. A 2024 study from the American Psychological Association found that technology-related workplace stress had increased significantly over two years, driven not by any single disruption but by the relentlessness of sequential disruptions. Gartner’s research tells us that employee willingness to support organizational change has dropped to historic lows.

This is not a productivity problem. It is a human sustainability problem. When the rate of cascading transformations exceeds the rate at which individuals can integrate, process, and find meaning in that change, something breaks. Not the technology, us. Decision fatigue becomes the default operating mode. Strategic paralysis masquerades as prudent deliberation. The most capable professionals in the room aren’t resistant to change, they’re exhausted by it.

And this is the paradox at the heart of our moment. The technology that promises to reduce cognitive burden is, by the very pace of its advancement, creating an unprecedented form of it. We cannot solve this by moving faster. We can only solve it by moving with greater intentionality.

Closing Thoughts

In Interstellar, Cooper makes a choice. He enters the black hole, not because he understands what’s on the other side, but because staying in orbit means watching everything he cares about slip further away. The event horizon demands commitment.

I believe we face an analogous decision. The cascading transformations I’ve described, the multiplicative capabilities, the compressing timeline, the human toll of perpetual disruption, are not going to slow down for strategic planning cycles or regulatory deliberation or professional comfort. The physics of this moment are pulling us forward whether we consent to it or not.

We must be deliberate about your trajectory. Purpose matters more when speed increases. Clarity matters more when complexity compounds. Alignment, between your technology, your values, and the people you serve, matters more when the margin for course correction shrinks with every passing quarter.

These cascading transformations will reshape our industry, our practice, and our careers. Are we building with enough intentionality to shape how that change lands? Or will we be the outside observer, watching decades pass through the window of an orbiting ship, wondering when the world became unrecognizable?

The event horizon doesn’t wait.

Neither should you.

If you found this article useful, you'll love the LawDroid AI Conference 2026. April 28–29, virtual, and completely free — two days of keynotes, panels, and workshops on AI and the legal profession. I'd love to see you there.

Register Now

If you want to understand how technology can be used as a force for access to justice, and what it really takes to build a mission-driven legal tech nonprofit from scratch, you need to listen to this episode. Amanda is at the forefront of justice technology in Louisiana and brings a rare combination of legal expertise, product thinking, and deep community roots to this work.

The Something Extra: Amanda Brown

Where I interview Amanda Brown, Executive Director of Lagniappe Law Lab, about building a statewide justice technology nonprofit from the ground up and using AI to expand access to justice across Louisiana.

Hey there Legal Rebels! 👋 I’m excited to share with you the 63rd episode 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 how technology can be used as a force for access to justice — and what it really takes to build a mission-driven legal tech nonprofit from scratch — you need to listen to this episode. Amanda is at the forefront of justice technology in Louisiana and brings a rare combination of legal expertise, product thinking, and deep community roots to this work.

From Rural Louisiana to the Forefront of Justice Technology

Join me as I interview Amanda Brown, Executive Director of Lagniappe Law Lab in New Orleans, Louisiana.

In this insightful podcast episode, Amanda shares her remarkable journey from a small, impoverished rural community in central northern Louisiana to a fellowship at Microsoft, and ultimately to founding Lagniappe Law Lab, a statewide justice technology nonprofit dedicated to helping legal aid organizations across Louisiana serve more people through smarter technology. She dives deep into how vibe coding is transforming her ability to prototype tools in real time, how she thinks about AI as a new layer in a complex system rather than a silver bullet, and why building technology thoughtfully — with the full picture in mind — is the only way to close the access to justice gap for real.

Her stories and insights underscore the power of approaching legal technology with both humility and ambition. This episode is a must-watch for anyone passionate about access to justice, legal innovation, and the enormous potential of AI to help the people who need legal help the most.

The Skinny

Amanda Brown, Executive Director of Lagniappe Law Lab, traces her path from growing up in a small, under-resourced town in rural Louisiana to earning a law degree at Loyola University New Orleans, completing a Microsoft fellowship focused on the Legal Navigator portal, and ultimately founding a statewide nonprofit dedicated to justice technology. Amanda reflects on how her economics background, her grandfather’s influence, and a formative litigation technology clinic in law school planted the seeds for a career at the intersection of law, access to justice, and technology. Throughout the conversation, she shares how she is using vibe coding to rapidly prototype tools for legal aid organizations, challenges the misconception that AI simply reduces workload, and emphasizes the importance of thinking holistically about technology as just one layer in a broader system. Her deep passion for the mission, and her honest acknowledgment of what is and is not known about where AI is headed, make this one of the most grounded and genuine conversations about legal technology you will hear.

Key Takeaways:

• Amanda grew up in a small, impoverished rural community in central northern Louisiana, an experience that deeply shapes her commitment to access to justice and Lagniappe’s focus on serving rural areas across the state

• Her grandfather, who never earned a high school diploma, was the key figure who pushed her toward college and ultimately toward law school, instilling a lifelong sense of justice and integrity

• A litigation technology clinic in her final year at Loyola University New Orleans was the pivotal moment where she first saw the connection between technology and scaling legal services

• A fellowship at Microsoft from 2017–2018, working on the Legal Navigator portal with the ABA Center for Innovation and the Legal Services Corporation, gave her the technical credibility and product management skills to launch Lagniappe

• Lagniappe Law Lab functions as a centralized, statewide technology resource for Louisiana’s legal aid ecosystem, solving the problem of organizations duplicating effort without coordinating

• Amanda is actively using vibe coding to prototype tools in near real time, describing the ability to go from a stakeholder meeting to a working prototype in under an hour as genuinely unfathomable compared to the past

• Her biggest pushback on AI misconceptions: AI does not reduce work, it creates different work, and the legal profession lives at “the edges of novelty” where human judgment will always be essential

• She is clear-eyed that nobody, not even the leading experts, truly knows where AI is headed, and that curiosity and openness are better responses than fear or hype

• Work-life balance, for Amanda, is a practice: clear work hours, time for exercise, travel, reading, and relationships, all of which she connects back to being able to show up fully for the mission

• Lagniappe derives its name from a Louisiana Creole word meaning “a little something extra,” and Amanda sees that spirit of going beyond as central to what justice technology can offer

Notable Quotes:

1. “I think technology is not the end all be all. It’s an additional layer on top of the core things that we’re doing. And so this version of technology, this tool is another layer that we have to think about.” - Amanda Brown (00:03:58-00:04:16)

2. “We have to really think of this holistically if we’re going to design and create technology systems that don’t further entrench problems that exist out there.” - Amanda Brown (00:06:25-00:06:39)

3. “My grandfather, he looked at me, he’s like, you know, that’s what lawyers do. That still sticks with me to this day, this concept of like the law is an instrument for justice.” - Amanda Brown (00:13:25-00:13:35)

4. “I think life is boring if you have a plan. A lot of life is kismet and accidents and how things fit together that we don’t expect. And that’s what makes it interesting.” - Amanda Brown (00:14:11-00:14:23)

5. “Being able to go from one meeting and listen to what problems people are having and what it is they actually need and want to — I’m looking at a prototype of what I built in response to that conversation right now on my screen. It’s unfathomable.” - Amanda Brown (00:27:36-00:28:07)

6. “The biggest misconception that you’re going to offload everything in your entire life to software. We’re in the legal profession. I think we live at the edges of novelty. AI is not good at novelty.” - Amanda Brown (00:31:39-00:32:11)

7. “Maybe the biggest one is that anybody knows what’s gonna happen. We don’t. Nobody knows what’s gonna happen. Don’t let Elon Musk tell you what’s gonna happen.” - Amanda Brown (00:32:33-00:32:44)

8. “Lagniappe — it’s the magic of a little something extra. In the early days, technology was extra. I don’t think it’s extra now. I think it’s actually essential.” - Amanda Brown (00:39:07-00:39:17)

Clips

AI Won’t Eliminate Novelty Jobs

AI Doesn’t Reduce Work

Why Rapid Prototyping Changes Everything

Work That Feeds the Soul

Amanda’s story is one of the most compelling I’ve heard in this space, not because it follows a straight line, but precisely because it doesn’t. She took the long way around, through economics, disaster recovery law, and a corporate fellowship in Redmond, Washington, before finding her calling building infrastructure for justice. And in doing so, she has helped ensure that legal aid organizations across an entire state don’t have to navigate the technology landscape alone.

What resonates most from this conversation is Amanda’s insistence on honesty. Honest about the complexity of the access to justice problem. Honest about what AI can and cannot do. Honest about the fact that nobody has all the answers. In a space that can be dominated by hype and grand promises, that clarity is both refreshing and necessary.

Closing Thoughts

What I love most about talking with people like Amanda is the reminder that the best legal tech work is rooted in something real — a community, a problem, a mission that goes far deeper than any particular tool or platform. Amanda didn’t set out to become a justice technology leader. She followed her sense of what was right, found the places where law and technology intersect in ways that actually help people, and built something that her state genuinely needed.

The vibe coding conversation was a highlight for me. The ability to move from a stakeholder conversation to a working prototype in under an hour is exactly the kind of practical empowerment I’ve been excited to see more lawyers and legal professionals embrace. It lowers the barrier to building, which ultimately lowers the barrier to access.

And I appreciate Amanda’s honest take on AI misconceptions. It creates different work, not less work. It is not magic, and it is not the end of legal professionals. But approached thoughtfully, as one layer in a broader, human-centered system, it is one of the most powerful tools we have for closing the justice gap.

For our Legal Rebels community, Amanda’s journey is both an inspiration and a model. You don’t need a perfect plan. You need integrity, curiosity, and the willingness to keep asking how can we do this better. That’s the something extra that makes the difference.

LawDroid AI Conference 2026

April 28–29, 2026 • Virtual • Free

The Year to Build

Sponsored by Practising Law Institute and ARAG Legal Insurance

Register Now

Let a friend know about this event before all the spots are taken!

Hey everyone! Tom Martin here, CEO of LawDroid and host of the upcoming LawDroid AI Conference 2026.

I’m thrilled to share an exclusive, behind-the-scenes look at what we have planned for you on April 28–29, 2026.

As a loyal subscriber to LawDroid Manifesto, you get the first peek at the speaker lineup, workshop details, and emerging AI tools on display, before anyone else!

This year’s theme is The Year to Build, a rallying cry for a legal profession that has spent years talking about AI and is now ready to act. We’re not just exploring what’s possible. We’re building it!

Our goal? To give you real, immediately applicable insights to harness the power of AI in your own practice, whether you’re just getting curious, actively experimenting, or already deploying agentic workflows in your organization.

And the best part? The LawDroid AI Conference 2026 is completely free and entirely virtual, so you can join from anywhere in the world.

Day 1 — April 28, 2026: Keynotes and Panels

All times Pacific • Add 3 hours for Eastern

8:00 AM — Welcome

Tom Martin, CEO of LawDroid; Adjunct Professor, Suffolk University Law School

I’ll kick off Day 1 with opening remarks, laying out our vision for how AI can transform the legal profession and address access to justice challenges.

8:15 AM — Keynote: Bridget McCormack

President and CEO, American Arbitration Association

Bridget is one of the most respected voices at the intersection of justice and innovation. Her keynote will set the tone for the entire conference, expect a bold, grounded perspective on where AI is taking the legal profession and what it means for how justice is delivered.

9:00–9:50 AM — AI and Ethics

Moderator: Joey Gartner | Panelists: Mark Palmer, Catherine Reach, Sateesh Nori

AI is powerful—but with great power comes great responsibility. This panel will tackle bias, transparency, and accountability in legal AI tools. Expect a frank, nuanced conversation about using AI responsibly while upholding the highest ethical standards.

10:00–10:50 AM — AI and Journalism

Panelists: Victor Li, Niki Black, Stephanie Wilkins

How is AI reshaping legal journalism—and how are journalists covering the AI story itself? This panel dives into the stories that matter, where AI has helped, and the concerns about accuracy and trust in an era of generative content.

11:00–11:50 AM — AI and A2J: Legal Aid

Moderator: Angela Tripp | Panelists: Scheree Gilchrist, Zach Zarnow, Lisa Colpoys

AI isn’t just for big firms. This panel spotlights how legal aid organizations are using AI to close the justice gap and make legal services more accessible to everyone. Real deployments. Real results. Real impact.

11:50 AM — Keynote: Ron Flagg

President, Legal Services Corporation

Ron leads the nation’s largest funder of civil legal aid. His perspective on AI’s role in expanding access to justice is essential listening for anyone working at the intersection of technology and the law.

12:30–1:20 PM — AI and A2J: Courts

Moderator: Shellie Reid | Panelists: Sonja Ebron, Jeannie Sato, Jason Tashea

Courts are on the front lines of the access to justice crisis and some are using AI to help. This session explores what court innovation looks like in practice, from self-represented litigant tools to case management.

1:30–2:20 PM — AI and the Legal Profession

Moderator: Nick Rishwain | Panelists: Carolyn Elefant, Brittany Hernandez, Mitch Jackson

From document automation to agentic coworkers, this panel explores how solos, small firms, and large practices are putting AI to work right now. Expect practical, real-world strategies you can implement immediately.

2:30–3:20 PM — AI and Education

Moderator: Kenton Brice | Panelists: Mark Williams, Colin Lachance, Nicole Morris

How do we prepare the next generation of lawyers for a world where AI is standard practice? These panelists are already updating law school curricula and CLE programs to include generative AI, data literacy, and practical AI skills.

3:45–4:35 PM — Women in AI

Moderator: Cat Moon | Panelists: Sharon Crane, Anastasia Boyko, Heidi Brown

A vital conversation about representation, leadership, and the unique perspectives women bring to the development and deployment of AI in law. Moderated by the remarkable Cat Moon—not a panel to miss.

4:45 PM — Wrap Up

I’ll close Day 1 with a recap of the key insights and a preview of what’s coming next.

Register Now

Day 2 — April 29, 2026: Keynote, Workshops and Tech Talks

All times Pacific • Add 3 hours for Eastern

8:00 AM — Welcome

Sateesh Nori, Chief Legal Futurist, LawDroid

8:15 AM — Keynote: Nikki Shaver

CEO and Co-founder, Legal Technology Hub

Nikki brings a global perspective on legal technology adoption and what it actually takes to make AI work in legal organizations. Her keynote kicks off a day of hands-on learning with real vision and context.

9:00–9:50 AM — State of AI

Moderator: Tom Martin | Panelists: Dr. Megan Ma, Damien Riehl, Joanne Sprague

Where is legal AI right now—and where is it headed? This panel takes stock of the state of the art, from frontier models and agentic workflows to the practical realities of deployment in legal organizations.

10:00–10:50 AM — Workshop: Skills Engineering

Instructor: Hannes Westermann

Learn how to design and build reusable AI skills, structured workflows that help AI models perform legal tasks consistently and accurately. This is next-level prompt engineering for professionals who want to build, not just use.

11:00–11:50 AM — Workshop: Vibe Coding

Instructor: Conor Malloy

You don’t need to be a developer to build with AI. Conor will show you how to use natural language to generate and iterate on functional tools, a practical, accessible introduction to coding in the age of AI.

12:30–1:20 PM — Workshop: Document Automation

Instructor: Quinten Steenhuis

Quinten is one of the foremost experts in legal document automation. He’ll walk you through building automated workflows that standardize document generation, reducing errors, saving time, and delivering better client work.

1:30–2:20 PM — Workshop: Context Engineering

Instructor: Kezia Hill

Context is everything when working with AI. Kezia will show you how to structure information, memory, and instructions to get dramatically better results from AI systems, an essential skill for building reliable legal AI tools.

2:30–3:20 PM — Ten-Minute Tech Talks

Patrick Palace, Maya Markovich, Claire Robinson, Marc Lauritsen, Taylor Sartor

Five innovators. Ten minutes each. Maximum impact. This rapid-fire session showcases some of the most exciting ideas and tools in legal AI right now.

3:45–4:35 PM — Workshop: AI Agents

Instructors: Tom Martin & Sateesh Nori

Agentic AI is the frontier—and this workshop will show you how to harness it. Sateesh and I will walk you through how AI agents work, how to design them for legal tasks, and how to start deploying them in your own practice or organization.

4:45 PM — Wrap Up and Thank You!

I’ll close the conference with key takeaways, a look ahead at where legal AI is going and a heartfelt thank you to everyone who made this event possible.

Register Now

Why You Can’t Miss This

• The Year to Build: From AI agents to document automation, walk away with tools and strategies you can deploy immediately.

• World-Class Speakers: Hear from Bridget McCormack, Ron Flagg, Nikki Shaver, and dozens of leading practitioners and innovators.

• Access to Justice Focus: Dedicated sessions on legal aid and court innovation—because AI should work for everyone.

• Hands-On Workshops: Five workshops covering Skills Engineering, Vibe Coding, Document Automation, Context Engineering, and AI Agents.

• Global Community: Connect with thousands of legal professionals from around the world—no travel required.

Thank You to Our Sponsors

A huge thank you to PLI (Practising Law Institute) and ARAG Legal Insurance for making this event possible and free for everyone.

Secure Your Spot Now

Ready to join us? Registration is free and open to all. As a LawDroid Manifesto subscriber, you have exclusive early access, so don’t wait!

Register Now

Thanks for reading, and I can’t wait to see you (virtually) on April 28–29. Let’s build the future of law together!

Tom Martin CEO & Founder, LawDroid Adjunct Professor, Suffolk University Law School Host, LawDroid AI Conference 2026 Creator, LawDroid Manifesto

If you want to understand how courage, vision, and a willingness to take a leap can completely transform not just your career but your entire life, you need to listen to this episode. David is a legal entrepreneur who has built LawLine into a leading CLE provider while also uprooting his family to live in Barcelona for two years—and he has the stories and the lessons to prove it.

Steering Your Ship: Lessons in Courage, Family, and Legal Entrepreneurship

Join me as I interview David Schnurman, CEO of Lawline and author of the newly released memoir 11 Suitcases.

In this rich and wide-ranging conversation, David shares his journey from a feral Brooklyn childhood to studying communications at George Washington University, through a winding road of sales jobs and real estate, and ultimately to building Lawline into the successful online CLE company it is today. He also takes us behind the scenes of his bold decision to move his family to Barcelona for two years, an experience that transformed his children, his company culture, and his own sense of what’s possible.

His stories weave together themes of entrepreneurship, intentional family life, the power of writing down your vision, and the courage it takes to turn your ship when you feel stuck in a narrow river. David also shares insights from his new book 11 Suitcases, which is already a bestseller on Amazon, and from his earlier book Fast Forward Mindset, which laid the philosophical groundwork for his leap to Barcelona. This episode is a must-watch for any lawyer or legal professional who has ever wondered whether it’s too late to make a bold change.

The Skinny

David Schnurman, CEO of Lawline and author of 11 Suitcases, brings a uniquely human perspective to legal entrepreneurship. In this episode, David traces his origin story from growing up in Park Slope, Brooklyn, where his father drove taxis through law school and his parents founded the original version of LawLine as a public access TV show in 1985, through his own circuitous path to building LawLine into a thriving online CLE company. The conversation centers on David’s decision to move his family to Barcelona in 2019, how that experience reshaped his children and his company culture, and the lessons he’s distilled into his memoir 11 Suitcases. David offers a compelling framework for anyone who feels stuck: write down your vision, tell people about it, take small steps, and be willing to turn your ship even when the current feels fixed.

Key Takeaways

• David’s father drove taxis through law school and founded the first version of LawLine as a public access TV show in 1985, giving David both grit and an entrepreneurial blueprint from an early age

• After graduating from George Washington University with a communications degree, David spent five years in sales before discovering his passion for law through studying for the real estate broker’s exam, a late pivot that ultimately led him to law school

• LawLine was rebuilt from scratch in 2006 when David joined; leveraging the company’s history since 1999 gave it credibility for accreditation that was critical to early growth

• The move to Barcelona in 2019 was not one big decision but a series of small steps: applying to schools, applying for visas, telling friends and family before they’d fully committed, each step making it harder to turn back

• David’s framework for taking a leap comes from his book Fast Forward Mindset: get out of your comfort zone, nip fear in the bud through journaling and gratitude, and define focus by setting a hard deadline

• Writing down a family vision and sharing it with others is a powerful catalyst, David’s decision to include “travel” in his family’s core values in 2015 set in motion the chain of events that led to Barcelona four years later

• LawLine operates on a four-day work week and prioritizes family-first values, which David sees as essential to his mission and his legacy

• The book 11 Suitcases was finally completed in honor of David’s mother, who passed away a year and a half ago, she had been his biggest cheerleader and visited the family in Barcelona during their stay

• Being comfortable and being happy are not the same thing, David’s personal mission is to inspire and empower people to live fully so they can look back with no regrets

Notable Quotes

1. “In 2019, I moved with my family to Barcelona for two years and we packed 11 suitcases and all of our things on the plane. It’s a story of why we went, what happened while we were there, and then how we transformed as a result.” - David Schnurman (00:01:25-00:01:42)

2. “What I love uncovering is somebody’s story. Whether we’re on air, on a podcast, or just meeting in person, I just need to understand who they are and what makes them tick.” - David Schnurman (00:25:18-00:25:30)

3. “I wrote it for my kids so they can memorialize this amazing experience that they had together.” - David Schnurman (00:02:15-00:02:20)

4. “It wasn’t one big decision. It was a lot of small steps. Like applying to the school. You can get in the school and still not go.” - David Schnurman (00:38:15-00:38:24)

5. “Write it down and tell it to people because I could tell you almost everybody doesn’t do that. And doing that—there’s a lot of data out there. If you write something down, it is much more likely to happen.” - David Schnurman (00:34:32-00:34:49)

6. “Being comfortable and being happy are not the same thing. And I’ve recognized that.” - David Schnurman (00:45:22-00:45:26)

7. “My personal mission, even though it’s broad, is to inspire and empower people to live their life to their fullest so they can look back and have no regrets.” - David Schnurman (00:44:50-00:45:02)

8. “You get 80% of your time with your kids before they’re 18. And so this trip really enriched that.” - David Schnurman (00:36:03-00:36:11)

Clips

Write Your Family’s Vision

How Grief Finished My Book

How Travel Changed Our Kids

How a Kayak Metaphor Changed Everything

David Schnurman’s story is a masterclass in the relationship between vision and action. From his father’s taxi rides through law school to his own improbable leap to Barcelona, David demonstrates that the most meaningful transformations rarely come from a single bold moment—they come from writing things down, telling people your intentions, and taking one small step at a time until the momentum carries you forward. His work at LawLine, now built around a four-day work week and family-first values, reflects the same philosophy: that professional excellence and a life fully lived are not in competition with each other.

Closing Thoughts

David Schnurman’s episode reminded me of something I believe deeply: the legal profession has always attracted people with far more complexity and range than we give ourselves credit for. David is a CEO, an entrepreneur, a stand-up comedian, a marathon runner, a two-time author, and a father who moved his whole family to Barcelona and came back transformed. None of those things exist in spite of each other, they’re all expressions of the same core drive to live without regret.

What struck me most was his point about how the Barcelona move wasn’t one courageous decision. It was dozens of small ones. That’s actually how most meaningful change happens, not in a single leap but in a series of steps that, taken together, add up to something remarkable. For those of us in the legal world who feel locked into a course, David’s story is both permission and a roadmap.

His new book 11 Suitcases is out now on Amazon and at 11suitcases.com. If you’ve ever felt like you’re steering a cargo ship down a narrow river and can’t turn around, read it. You might just surprise yourself.

Hey everyone!

Last year, I challenged us all to embrace healthy anarchy: intentional disruption, open-minded exploration, curiosity and freedom. That message was about giving ourselves permission to break from tradition and reimagine what legal practice could look like in the age of AI.

This year, I want to build on that foundation. Because disruption without construction is just noise.

When I co-hosted the American Legal Technology Awards in October of last year, I shared something that’s been on my mind: We’ve had our year of experimenting. We’ve had our year of planning.

Now is the time to build!

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.

A Time to Build

Think about where we’ve been. In 2024, legal professionals were experimenting with AI, testing the waters, kicking the tires, figuring out what these tools could even do. In 2025, we started planning, developing strategies, thinking about integration, imagining possibilities. But planning without building is just dreaming.

2026 is different.

AI is reshaping the legal industry at an unprecedented pace, and it’s creating opportunities that were once unimaginable. The blueprints are drawn. The tools are in hand. Now is the moment for all of us as legal innovators to roll up our sleeves and harness this power to make positive change in the world.

Exceptional Legal Innovators who are building this year are:

• Jamie Tso, who is ushering in a wave of lawyer vibe-coding.

• Amanda Brown, who is using code vibing to bring justice to the people.

• Zack Shapiro, who is a 10x lawyer with his Claude-Native law firm.

This isn’t about waiting for perfection.

It’s about shipping. Iterating. Getting something out there that serves real people with real legal needs, and then making it better.

LawDroid’s mission remains simple yet powerful: empowering justice everywhere. But empowerment in 2026 means moving from vision to execution, from talking about what AI could do to showing the world what it does.

What Are We Building?

Building in this context means more than writing code or deploying chatbots. It means constructing new systems, new relationships, and new pathways to justice:

Building Access at Scale: We now have the tools to deliver high-quality legal guidance to anyone, anywhere. The question is no longer can we but will we. Every AI-powered legal tool we build is a brick in the bridge between those who have access to justice and those who don’t.

Building New Models of Practice: The old billable-hour, office-bound model isn’t just outdated, it’s a barrier. Builders in this space are creating dynamic, responsive, human-centered legal services that meet people where they are, on their phones, in their communities, in their language.

Building Community: At the American Legal Technology Awards, I was reminded that what holds this movement together isn’t technology, it’s us. It’s the sense of belonging, togetherness, and camaraderie we share. Technology is one way we come together, but at bottom, it’s human beings collaborating from a common place of experience, wanting better lives for ourselves and our families.

Why Building Matters Now

We’re living through a difficult time. Political tensions, economic uncertainty, and deep divisions make it tempting to retreat, to wait, to play it safe. But this is precisely when building matters most.

In times of difficulty, the answer isn’t to hunker down. It’s to build something that makes the world a little more just, a little more accessible, a little more human.

The mission we’ve carried from day one at the American Legal Technology Awards captures this perfectly:

• Expand our understanding of what’s possible. Every builder pushes the boundaries of what legal technology can achieve.

• Encourage a virtuous cycle of improvement. When we celebrate achievements, we inspire others to build more and build better.

• Create a more just society. Heaven knows we need that right now.

This aligns with LawDroid’s mission: to promote justice everywhere.

Come Build With Us

The Year to Build isn’t just a theme, it’s an invitation.

I’m calling on every lawyer, technologist, legal aid worker, and innovator to stop waiting for someone else to solve the access-to-justice crisis. Stop waiting for the perfect tool. Stop waiting for permission.

The future of law won’t be built by spectators. It will be built by people like you: the ones who showed up, who care, who are ready to get their hands dirty.

So here’s my challenge for 2026: Build something.

Build an AI tool that helps a pro bono client. Build a workflow that gives you back hours to spend on meaningful advocacy. Build a partnership with someone outside your usual circle. Build a practice that looks nothing like what came before.

If you’d like to learn how, attend the LawDroid AI Conference, coming up next month:

LawDroid AI Conference 2026

April 28-29 • Virtual • Free (Sponsored by PLI)

“The Year to Build”

This free, two-day virtual conference brings together lawyers, legal aid advocates, court innovators, technologists, academics, and legal-tech enthusiasts from around the world to learn, share ideas, and discover practical ways to use AI in legal work and access to justice. I’ll be sharing our full two-day schedule later this week.

Don’t miss it, snag your spot today!

Register Now

The healthy anarchists lit the fire. Now it’s time to build with it.

Let’s build the future of law — together!

Tom Martin is CEO & Founder of LawDroid, Adjunct Professor at Suffolk University Law School, and Author of the forthcoming AI with Purpose: A Strategic Blueprint for Legal Transformation (Globe Law and Business). He is “The AI Law Professor” and writes his eponymous column for the Thomson Reuters Institute.

If you want to understand how to practically implement AI at the very core of a law firm, not as a bolt-on tool but as a fundamental way of working, you need to listen to this episode. Zack is at the forefront of Claude-native legal practice and ignited a profession-wide conversation with a single article that reached over seven and a half million views.

How One Lawyer Built a Claude-Native Law Firm and Changed the Conversation

Join me as I interview Zack Shapiro, founder of Raines LLP.

In this insightful podcast episode, Zack shares his journey from Yale Law School through federal clerkships, a stint at Davis Polk, startup co-founder life, and finally to building a lean, AI-powered boutique firm that punches well above its weight. He dives deep into the philosophy behind his viral article on building a Claude-Native Law Firm, and more importantly, the practical reality of how he actually practices law today using custom AI skills, Claude Code, and agentic workflows that handle everything from contract redlining to multi-threaded legal research.

His stories and insights make a compelling case that the secret to using AI well isn’t the output of the model: it’s the quality and specificity of your inputs. This episode is a must-watch for any lawyer trying to understand not just what AI can do, but how to build a practice around it in a way that compounds value over time.

The Skinny

Zack Shapiro, founder of Raines LLP, sparked a global conversation in the legal profession when his article on building a Claude-native law firm accumulated over seven and a half million views, including roughly a million and a half lawyers. In this conversation, Zack unpacks exactly what that phrase means in practice: a two-person firm that represents about 200 startups and investors, powered not by expensive legal AI tools, but by deeply customized Claude skills and agentic workflows that Zack built through iterative conversation with the AI itself. His core thesis is simple but counterintuitive: the legal AI industry is largely focused on the wrong thing. Fine-tuning models on legal documents or wrapping Claude in a specialized dashboard misses the point. The real leverage is in how you instruct the model—and lawyers, trained to be precise and detailed communicators, are uniquely positioned to excel at this. For Zack, this isn’t a mindset shift that requires technical skill. It requires imagination, curiosity, and the willingness to treat AI as a thinking partner rather than a magic output machine.

Key Takeaways

• The viral success of Zack’s “Claude-Native Law Firm” article reflected widespread anxiety about AI’s impact on white-collar work, but his message was fundamentally optimistic: there is a path forward for lawyers, and it looks like what he’s already doing.

• The secret to getting great results from AI is not the model’s training data: it’s the quality and specificity of the input. Lawyers’ training in precise, detailed communication is a natural superpower for prompting.

• Specialized legal AI tools often constrain rather than enhance the underlying model. Zack argues that working directly with frontier AI is both more powerful and more flexible than operating through a pre-built legal dashboard.

• Zack’s practice runs on custom Claude skills, essentially AI standard operating procedures that encode his preferences, formatting requirements, and quality-control steps so he doesn’t have to repeat them with every task.

• Skills are built through conversation, not coding. Zack fed Anthropic’s 33-page PDF on building custom skills directly into Claude, asked it to review his prior chats, and had Claude recommend and build the five most useful skills for his practice.

• For complex legal assignments, Zack writes prompts that are around 2,000 words, more like the detailed briefing a partner gives a senior associate than the one-sentence queries most people use with ChatGPT.

• The ideal AI interface for lawyers isn’t a legal-specific dashboard. Zack points to the onboarding scene from the movie Her as a closer model: an AI that absorbs your context, interviews you, and then starts working with you directly.

• Lawyers who adopt this approach will be able to deliver better quality work faster and at lower cost than those who don’t, and that gap will widen quickly.

• The next wave of legal questions will involve truly agentic AI operating in the real world, intersecting with blockchain, legal personhood, and regulatory frameworks that haven’t been written yet. That’s an enormous opportunity for lawyers with the right mindset.

• Work-life balance, for Zack, comes from doing work you genuinely love, and modern AI has made the interesting parts of legal practice more accessible by eliminating a lot of the drudgery.

Notable Quotes

1. “I think there is a lot of anxiety happening right now about the way that AI is going to change the white collar economy in America... I wanted to reply to those two articles in some way and say, listen, there is an optimistic path here for professionals, and it looks like what I’m doing now.” - Zack Shapiro (01:44-02:28)

2. “The secret sauce about using AI well versus poorly is not about the output of the LLM. It’s about the input. It’s about the prompt.” - Zack Shapiro (03:49-03:57)

3. “LLMs are the sort of general purpose technology where if you give it fuzzy, vague instructions, it’s going to give you fuzzy, vague output. Whereas if you are really detailed and you’re really specific about what you want out of the LM—both skills lawyers are really used to having—you can get pretty incredible results.” - Zack Shapiro (04:09-04:31)

4. “I think a lot of these legal tech tools feel a bit like Juicero... The magic is the bag. The bag here is the frontier model and you actually want to be able to squeeze it with your hand in the way that you want. You don’t want it inside this large chrome press.” - Zack Shapiro (17:55-18:36)

5. “The limiting factor is not your skill. It’s not your willingness or ability to learn tools. The limiting factor is your imagination and just willingness to go for it.” - Zack Shapiro (21:31-21:44)

6. “If you don’t do this and you compete against people who do, they’re just going to run circles around you on quality of their lawyering and price.” - Zack Shapiro (21:59-22:07)

7. “If you know how to talk to an associate, you know how to talk to Claude.” - Zack Shapiro (30:50-30:54)

8. “Since the sort of modern version of AI has come out, I found myself just waking up being more excited to work than I ever had before... The drudgery that made that hard is increasingly just gone.” - Zack Shapiro (38:19-38:35)

Clips

Stop Buying The Juicero of Legal AI

AI Agents + Crypto Could Go Rogue

The Secret Isn’t Output — It’s Input

Spend $100 or Get Left Behind

Zack’s story is a rare combination: a practitioner who has actually built the thing he’s writing about, a legal thinker who predicted where the profession was heading before most others could see it, and a communicator who found a way to articulate something genuinely new in language that resonated with millions. What makes this conversation so valuable isn’t the abstract vision, it’s the concrete, step-by-step reality of how a working lawyer rebuilt his practice around AI. From the mechanics of custom skills to the philosophy of treating AI as a thinking partner rather than a search engine, Zack offers a blueprint that any motivated lawyer can follow. He’s also clear-eyed about what’s at stake: this isn’t a story about a technology you can safely ignore until it matures. The window for early movers is open right now.

Closing Thoughts

As someone who’s spent years in the legal technology space, I found this conversation with Zack one of the most grounded and practically useful I’ve had. What strikes me about Zack isn’t just the viral success of his article, it’s the fact that he built the system first and wrote about it second. He’s not theorizing. He’s practicing.

The point he makes about inputs over outputs is something I think about constantly. We tend to fetishize the model (its size, its training data, its benchmarks). But as Zack demonstrates, the leverage available to any lawyer today comes from the quality of the conversation they’re willing to have with the AI. Detailed, specific, iterative. The same discipline that makes a great lawyer makes a great AI collaborator.

What also stays with me is his urgency. Zack isn’t alarmist about this, but he’s honest: lawyers who adopt this approach now will have meaningful advantages over those who don’t. The gap is real and it’s growing. The good news, and Zack genuinely means this as good news, is that the barrier to entry is a conversation, not a certification. If you can explain your work clearly, you can build something powerful.

For our Legal Rebels community, I’d encourage you to take Zack’s advice seriously. Start the $100-a-month subscription. Ask Claude to interview you about how you work. See what it builds. The door is open, and as Zack’s article proved, the people walking through it are already running.

Link to Zack’s article: The Claude-Native Law Firm (February 27, 2026)

In this month’s AI Double Take, LawDroid CEO Tom Martin and Chief Legal Futurist Sateesh Nori survey a turbulent February in AI, from a bombshell economic forecast to a viral legal AI post, a proposed New York law, and a surprise leap to the top of the App Store. The hosts wrestle with AI’s accelerating displacement of white-collar workers, what it means for the legal profession’s identity, and why human judgment still matters.

Key Takeaways

1. The Citrini Research Memo — A Sobering Economic Forecast

A report by Citrini Research predicts that by 2028, AI could trigger a cascade economic collapse: starting with the software sector, spreading to SaaS, then causing a mortgage crisis as unemployed white-collar workers default, potentially ending in a depression. While the outcome is not certain, the scenario deserves serious attention.

2. Dario Amodei on Accelerating Intelligence

Anthropic CEO Dario Amodei stated in a recent interview that AI models are doubling in intelligence roughly every four months — a pace that makes the economic disruption scenario plausible, not just speculative.

3. The Viral “Claude-Native Law Firm” Post

Zack Shapiro’s post on running a two-person law firm with Claude, doing the work of ten lawyers, surpassed 7.5 million views. Tom sees this as validation of LawDroid’s core thesis: AI doesn’t replace lawyers, it multiplies their impact. Tom plans to bring Zack on as a podcast guest.

4. The Legal Profession’s Identity Crisis

The hosts argue that AI is forcing a fundamental reckoning for lawyers. Traditional roles, translating complex legal machinery for clients, are no longer exclusively human. The real crisis is one of professional identity: if AI can do legal work faster, cheaper, and at scale, what does it mean to be a lawyer? Sam Glover’s Substack explored similar themes.

5. The Case for Dismantling Legal Friction

Sateesh argued that much of the legal system’s complexity has historically served lawyers more than clients, from the billable hour model to access barriers. AI presents an opportunity to rebuild a frictionless, affordable, 24/7 legal system. The hosts invoked Roscoe Pound’s century-old distinction: a profession serves people; a job just makes money.

6. New York’s Proposed AI Legal Advice Ban — A Step Backward

A proposed New York bill would make it illegal for AI chatbots to provide legal advice. Both hosts see this as misguided. Sateesh argued UPL enforcement should focus on quality of legal help, not who delivers it, and pointed to the ongoing Upsolve First Amendment case as a parallel battleground. New York’s millions without legal access make such legislation particularly damaging.

7. Depositron as a Model for Empowered Consumers

LawDroid’s Depositron app (NYC tenant security deposit recovery tool) was cited as an example of consumer-driven legal AI: users make informed choices about a tool that provides legal information, not advice, and helps draft letters at their direction. The hosts argued consumers deserve this kind of access and are capable of exercising informed choice.

8. Anthropic Tops the App Store — AI as Utility

After Anthropic’s high-profile pushback against Department of Defense requests to use Claude for surveillance and lethal autonomous drone applications, Claude became the #1 app on the App Store, with a server outage from the surge in users. The hosts see this as consumers voting with their downloads, and as evidence that AI models are now essential infrastructure, akin to utilities.

9. Human Judgment Remains Irreplaceable — for Now

Both hosts’ final takes converge: even if AI can replicate decisions, humans are accountable in ways machines are not. Society values human judgment because humans can be held responsible. The legal profession must lean into empathy, ethics, and accountability as its durable differentiators.

Show Notes

Topics Covered

• Citrini Research Memo: AI economic collapse forecast (2028 scenario)

• Dario Amodei / Anthropic: AI doubling in intelligence every 4 months

• Zack Shapiro’s viral “Claude-Native Law Firm” post (7.5M+ views)

• Sam Glover Substack on agentic legal AI

• The lawyer identity crisis in the age of AI

• Roscoe Pound quote: profession vs. job

• New York proposed bill banning AI legal advice chatbots

• Upsolve First Amendment / UPL case in New York

• LawDroid’s Depositron (NYC tenant security deposit recovery app)

• Anthropic vs. Department of Defense (surveillance / autonomous drones)

• Claude #1 on App Store + server outage from demand surge

• AI as utility infrastructure

People & Organizations Mentioned

• Tom Martin — CEO & Founder, LawDroid

• Sateesh Nori — Chief Legal Futurist, LawDroid

• Zack Shapiro — Lawyer / solo practitioner, viral Claude law firm post

• Sam Glover — Legal tech writer / Substack

• Dario Amodei — CEO, Anthropic

• Bridget McCormick — Keynote speaker, LawDroid AI Conference 2026 (Day 1)

• Roscoe Pound — Historical legal scholar (cited)

• Citrini Research — Economic research consultancy

• Upsolve — Legal access nonprofit, subject of pending First Amendment / UPL case

Upcoming: LawDroid AI Conference 2026

• Dates: April 28–29, 2026

• Format: Virtual (attend from anywhere)

• Cost: Free

• Features: Panels, workshops, keynote speakers

• Third annual conference — register at lawdroidaiconference.com

Final Takes

Sateesh Nori:

“There’s always something new coming down the road. Every day I wake up excited because something’s happened in this space — and it keeps me motivated.”

Tom Martin:

“It seems scary sometimes with all the change, but there’s definitely a place for us. Human judgment cannot be replaced — not because machines can’t reach conclusions, but because we value humans making decisions. We can be held accountable. There will always be a place for human judgment.”

AI Double Take is produced by LawDroid | lawdroid.com

Last week, Zack Shapiro published a post on X called “The Claude-Native Law Firm.” If you’re reading this newsletter, you probably saw it. Over 7.5 million people did. More than 320 comments. Thousands of reactions, and lawyers reaching out to him directly. For context, there are about 1.3 million lawyers in the United States. This wasn’t a legal tech moment. It was a cultural moment — a signal that the anxiety around AI and professional work had been waiting for someone to say: here’s a path forward, and it’s not as scary as you think.

I got Zack on the LawDroid Manifesto Podcast this week (that episode drops Monday) and the conversation went deeper than the article. What I want to share isn’t a summary of his workflow. It’s what I think his breakthrough actually means, and why it matters far beyond one lawyer’s practice.

If this sounds interesting to you, please read on…

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.

The Real Unlock: Mindset, Not Technology

Most of the commentary around Shapiro’s post has focused on the how. The skills. The prompts. The tracked changes. All of that is impressive. But in our conversation, Zack said something that cut through the tactics: “The limiting factor is not your skill. It’s your imagination and your willingness to go for it.”

That’s not a statement about technology. That’s a statement about mindset.

For three years, the legal profession has been circling AI like it’s a dangerous animal. Cautious. Skeptical. Waiting for someone else to go first. What Shapiro did (and why it resonated with millions) is he walked into the room and said, I went first, and I’m thriving. Not surviving. Thriving. Having more fun practicing law than ever before.

The unlock isn’t Claude. It’s permission. The permission we grant ourselves to reimagine what it means to be a lawyer when the tedious, mechanical parts of the work (the formatting, the first-pass drafting, the citation checking) are handled by a machine, and what’s left is the part you actually went to law school for. The judgment. The credibility. The human relationship with the client who needs you to understand what’s really at stake, for them.

Zack put it beautifully in our interview: “It’s not how we do things. It’s how I do things.” That single shift, from institutional conformity to individual expression through AI, is the psychological breakthrough most people missed in the viral noise.

The Mindset Beneath the Method

Here’s what I’ve learned teaching law students at Suffolk University Law School and building AI legal tools for over a decade: the technology is never the hard part. The hard part is the shift in thinking that lets you use it.

Shapiro’s prompts for complex assignments average 2,000 words. He’s not chatting with AI. He’s briefing it the way a senior partner briefs a trusted associate, with context, nuance, judgment, and specificity. That skill, the ability to be precise and detailed, logical, in written instructions, is literally what “thinking like a lawyer” develops. Lawyers don’t need to learn prompt engineering. They need to recognize that they’ve been doing it their entire careers.

This is what I call the hidden superpower of the legal profession. The same discipline that makes a great contract drafter, anticipating edge cases, being specific about terms, structuring logic clearly, is exactly what can make someone effective with AI. The profession that’s most anxious about being replaced is, paradoxically, the one best equipped to lead the transformation.

In our conversation, Zack talked about how he hates learning tools. Hates dashboards and toggles. Has ADD. And yet he’s built one of the most sophisticated AI-integrated legal practices in the country. Why? Because this technology doesn’t ask you to conform to it. It conforms to you. You speak to it in plain English. You tell it how you think. And it remembers and understands.

That’s a fundamentally different relationship between a professional and their tools than anything we’ve seen before. And it changes who gets to be good at this. Not the most technically skilled. Not the most institutionally compliant. The most self-aware, curious and brave. The ones who can articulate how they think and why they make the decisions they make.

The Knock-On Effects No One Is Discussing

If Shapiro’s approach scales (and it will) the ripple effects go far beyond efficiency gains for boutique firms.

The mentorship model inverts. Zack described packaging his judgment into a plugin that any associate could install and immediately produce work at his standard. Think about what that means. The traditional apprenticeship model, where it takes years of proximity and correction to transmit a senior lawyer’s way of thinking, compresses into an instruction file. Knowledge transfer doesn’t disappear. It accelerates. The junior lawyer’s job isn’t to slowly absorb the partner’s preferences through osmosis. It’s to exercise judgment on top of a baseline that’s already calibrated to the highest standard.

The value of experience appreciates, not depreciates. This is the most hopeful implication for lawyers fearing replacement, and the one I keep returning to in my teaching. If AI handles execution, then what clients pay for is the judgment that only comes from years of practice. Experienced lawyers aren’t threatened by this technology. They’re the ones with the richest raw material to feed into it. As Zack told me, “Experienced lawyers have an enormous advantage in this new world, and most of them don’t realize it.”

The access-to-justice gap finally has a credible path to closing. Shapiro’s article is about a Yale Law grad, as a two person law firm, punching above its weight. But the same architecture (encoding expert judgment into AI skills) can be pointed at an entirely different problem: the 80% of Americans who face legal issues without any legal help at all. When expert legal reasoning can be captured, verified, and deployed at scale, the question shifts from “can we afford to help everyone?” to “what’s our excuse for not trying?” That’s the work I’ve dedicated LawDroid to, and it’s why this moment matters beyond productivity.

The Transformation Triangle

What Shapiro illuminated brilliantly is the tools layer. But tools alone have never transformed a profession. You need three things working together: Tools (the AI capabilities), Expertise (the human judgment Shapiro rightly champions), and Education (teaching the next generation how to think within this new paradigm and the feedback loop to improve). That’s what I call the Transformation Triangle, and it’s the framework behind everything I do: my building AI, my teaching, my consulting, and the book I’m writing.

Shapiro’s post went viral because he made the tools layer tangible and real. But the reason millions responded isn’t that they want a workflow tutorial. It’s that they want to know: Is there still a place for me?

The answer is yes. A bigger place than before. But only if you’re willing to do the thing Zack did: sit down, articulate how you think, and trust that your judgment is the asset that makes all of this work.

Closing Thoughts

Something is shifting. Yes, technology is rapidly advancing day-by-day. But, what’s really shifting is mindset. Shapiro’s post landed like lightning because the ground was already charged for it. Professionals everywhere are feeling the tremors and looking for a signal that says: you’re not being replaced, you’re being unleashed.

That’s the real story here. Not a workflow. Not a tool. A new relationship between human expertise and machine capability that makes both more valuable. And we’re just at the beginning.

Listen to my full conversation with Zack on the LawDroid Manifesto Podcast, dropping Monday morning. He’s candid, sharp, and genuinely optimistic. I think you’ll hear what I heard: not just a clever practitioner, but someone who stumbled into a truth the whole profession needed to hear at exactly the right moment.

Stay tuned!

Tom Martin is CEO & Founder of LawDroid, Adjunct Professor at Suffolk University Law School, and Author of the forthcoming AI with Purpose: A Strategic Blueprint for Legal Transformation (Globe Law and Business). He is “The AI Law Professor” and writes his eponymous column for the Thomson Reuters Institute.

Related:

1. Zack Shapiro, The Claude-Native Law Firm (February 27, 2026)

2. Thomas G. Martin, The Transformation Triangle (August 28, 2025)

Hit reply and tell me — I read every response and it shapes what I write next.

If you want to understand how technology is transforming the pro bono ecosystem and closing the justice gap for tens of thousands of people who desperately need legal help, you need to listen to this episode. Kristen is at the forefront of legaltech innovation for access to justice and brings a unique combination of mission-driven passion and hard-nosed startup experience to this critical challenge.

Building the Infrastructure That Pro Bono Always Needed

Join me as I interview Kristen Sonday, co-founder and CEO of Paladin, the leading pro bono management platform.

In this episode, Kristen shares her remarkable journey from first-generation college student in New Jersey to Princeton, the U.S. Department of Justice, and ultimately to building Paladin, a platform that has now facilitated over 55,000 pro bono connections across the country. She dives deep into how Paladin is transforming the pro bono ecosystem by replacing manual emails and spreadsheets with real-time, data-driven infrastructure that connects legal aid organizations with law firms, in-house teams, and law school students nationwide.

Her stories and insights underscore the urgency of the access to justice crisis, where 92% of low-income individuals’ civil legal needs go unmet, and how Kristen believes AI may be the single most powerful development of our generation to help close that gap. This episode is a must-watch for anyone who cares about using technology to democratize legal services and build a more just society.

The Skinny

Kristen Sonday, co-founder and CEO of Paladin, shares her journey from a working-class New Jersey upbringing through Princeton, the U.S. Department of Justice, and a New York tech startup, to co-founding the legal profession’s leading pro bono management platform. Kristen explains how Paladin replaces the fragmented, manual ecosystem of emails and spreadsheets with a real-time database of pro bono opportunities that connects nonprofits and legal aid organizations with big law firms, corporate legal teams, bar associations, and now law schools. With 55,000 pro bono connections made to date, Paladin is demonstrating measurable impact at scale. Kristen also explores how the professionalization of pro bono (through billable credit, CLE integration, and data-driven reporting) is shifting firm culture and engagement. And she makes a compelling case for AI as a transformative force in intake, triage, and case matching, with the potential to finally address the staggering reality that 92% of low-income civil legal needs go unmet.

Key Takeaways:

• Paladin was born from the intersection of Kristen’s DOJ experience witnessing justice system barriers and her startup experience building matchmaking technology at Grouper; Paladin is, at its core, a matchmaker for pro bono

• Prior to Paladin, the entire pro bono ecosystem ran on manual emails and spreadsheets with no real infrastructure; Paladin built the first real-time national database of pro bono opportunities

• Paladin has facilitated over 55,000 pro bono connections to date, serving low-income immigrants, veterans, elderly individuals, children with special needs, tenants, and benefits seekers

• The professionalization of pro bono is accelerating, firms are now offering billable credit, incorporating pro bono into performance reviews and CLE requirements, and using data to measure ROI

• Paladin boosts attorney engagement in pro bono programs by over 30% in the first year and gives administrators actionable insights they never had before

• Paladin launched for law schools this past fall, partnering with over 30 schools and 22,000 students who took on 5,600+ pro bono opportunities in just the first semester

• Approximately 92% of low-income individuals’ civil legal needs are unmet, and legal aid organizations must turn away about 50% of people who qualify due to lack of capacity

• Kristen believes AI could be the most powerful development of our generation for closing the justice gap, particularly in intake, triage, issue-spotting, and eligibility vetting

• Kristen’s nonlinear career path, from DOJ to startup to Paladin, was essential; she argues that diverse early experiences compound into greater impact over time

• The key to managing multiple roles and organizations is identifying which balls are glass and which are plastic, and delegating ruthlessly in areas of weakness

Notable Quotes:

1. “I think AI could be the single most powerful development in our generation to help close the justice gap.” - Kristen Sonday (00:38:18-00:38:25)

2. “Prior to Paladin, the entire ecosystem was run on emails and spreadsheets that were incredibly manual and ad hoc. And there just hadn’t really been tech investment in this area.” - Kristen Sonday (00:06:27-00:06:38)

3. “You are 11X more likely to win an immigration case if you have a lawyer with you than not. The statistics are just crazy about how meaningful it is to have representation.” - Kristen Sonday (00:22:45-00:22:57)

4. “Paladin has helped make over 55,000 pro bono connections. And these are low-income immigrants, veterans, elderly folks, kids with special needs.” - Kristen Sonday (00:43:38-00:43:50)

5. “The path is never linear. I think of every career experience, especially that you have as someone on the junior side, is really a stepping stone to figuring out where you’re meant to be, what you’re meant to do.” - Kristen Sonday (00:20:54-00:21:07)

6. “You’re juggling a million balls and you have to figure out which ones are glass and which are plastic because some are bound to drop.” - Kristen Sonday (00:42:40-00:42:50)

7. “Paladin wouldn’t be as successful as it is if I hadn’t had that nonlinear path of access to justice and technology, because now Paladin is this great intersection of both of them.” - Kristen Sonday (00:29:07-00:29:17)

8. “These legal aid organizations have to turn away about 50% of people, even who qualify for pro bono, because of a lack of capacity. AI, I believe, can help with both the lack of capacity and the lack of infrastructure.” - Kristen Sonday (00:38:41-00:38:53)

Clips

There Is No Work-Life Balance

Excellence Is How You Change the World

Representation Changes Outcomes

How Paladin Boosts Pro Bono Engagement

Closing Thoughts

What I love most about Kristen’s story is that it is proof of something I deeply believe: the people who change the legal profession aren’t always lawyers. Kristen came at pro bono as an operator, a technologist, and a mission-driven builder, and she saw the gap that those of us inside the profession often take for granted. The fact that the entire pro bono ecosystem was running on emails and spreadsheets before Paladin is both astonishing and all too familiar.

What moves me is the scale of what she’s built. 55,000 pro bono connections. Over 22,000 law students engaging with real cases in their first semester on the platform. Those are not abstract numbers, those are people who got a lawyer when they needed one most. Veterans. Immigrants. Tenants facing eviction. Families navigating systems designed to confuse them.

And then there’s the AI conversation. Kristen put it plainly: 92% of low-income civil legal needs go unmet. That is a crisis hiding in plain sight. For the first time, I genuinely believe technology gives us the tools to do something about it, not just incrementally, but at scale. Intake automation, triage, issue-spotting, case matching, these are not futuristic ideas. They are being deployed right now by organizations like Paladin and LawDroid.

For our Legal Rebels community, Kristen’s episode is both a call to action and a reminder of why we do this work. If your firm doesn’t yet have Paladin, go to joinpaladin.com and change that today. And if you’re a law student, a legal aid attorney, or a corporate counsel wondering how to make your pro bono hours count, Kristen has built the on-ramp. All you have to do is show up.

If we achieve artificial general intelligence, will we still need lawyers?

The typical answers fall into two camps. The doomers say no: lawyers are just information processors, and AGI will process information better. The deniers say of course: because law is special and machines could never understand it. Both camps are wrong. And the reason they’re wrong isn’t philosophical. It’s mathematical.

There’s a concept in computer science called tractability that gives us a far more precise, and far more useful, answer to this question than any amount of hand-waving about “the human touch.” It tells us exactly what remains for human lawyers, and why, even in a world with superintelligent machines.

If this sounds interesting to you, please read on…

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.

What Is Tractability?

In computer science, problems fall into two buckets. Tractable problems can be solved efficiently: as the problem gets bigger, the time it takes to solve it grows at a manageable rate. Sorting a list of names or searching a database? Tractable. A computer handles these gracefully, even at enormous scale.

Intractable problems are different. They aren’t impossible, they’re just impossible to solve efficiently as they grow. Think of the difference between cleaning a room and counting every grain of sand on a beach by hand. You could technically do the latter, but you’d run out of time before you finished.

The classic example is the Traveling Salesperson Problem: given a list of cities, what’s the shortest possible route that visits each city once and returns home? With 10 cities, your laptop can figure it out over lunch. With 100 cities, the number of possible routes exceeds the number of atoms in the observable universe. The problem didn’t change; it just scaled beyond any computer’s reach.

One of the greatest unsolved questions in all of science, known as the P vs NP problem, asks whether every problem whose answer can be checked quickly can also be solved quickly. In plain English: if I hand you a solution and you can verify it’s correct in seconds, does that mean a fast method to find that solution must exist? Nobody knows. It’s a million-dollar question, literally, the Clay Mathematics Institute has a prize waiting. Most experts suspect the answer is no, meaning some problems are fundamentally, permanently hard to solve efficiently, no matter how powerful the computer.

This matters enormously for law.

Mapping Tractability Onto Legal Work

Here’s where it gets interesting. Much of what lawyers do day-to-day is already tractable, or rapidly becoming so.

Document review? Tractable. Predictive classification can sort millions of files into “relevant” and “not relevant” at scale. Legal research? Tractable. Finding a specific precedent is fundamentally a search-and-index problem, and databases like Westlaw handle it beautifully. Contract management? Tractable. Tracking thousands of expiration dates and flagging non-standard clauses is exactly the kind of structured, repeatable work that machines eat for breakfast.

These are the tasks that AGI, or even today’s narrow AI, will continue to absorb. And we should let it. Automating tractable work frees lawyers to focus on what actually requires them.

Because the practice of law, at its core, is intractable.

Why Legal Judgment Resists Computation

Corporate litigation is the textbook real-world intractable problem. Consider the variables: millions of documents, thousands of precedents, multiple parties with competing interests, and the gloriously unpredictable variable of human behavior. Add more defendants and the number of possible cross-claims and settlement combinations doesn’t just double: it explodes exponentially.

Worse, litigation is a moving target. A witness changes testimony. A judge issues a surprise ruling. New regulations land mid-trial. In a tractable math problem, the rules stay fixed. In litigation, the problem itself keeps changing.

And then there’s the adversarial dimension. Unlike a math equation, litigation involves an opponent actively trying to make the problem harder for you. This creates layers of strategic recursion (“I think that they think that I think...”), that no algorithm can cleanly resolve.

In-house counsel face their own version of intractability. Balancing a CEO’s aggressive growth targets against a CFO’s budget constraints, a board’s fiduciary duties, and a regulator’s shifting rules is what physicists call an “N-body problem.” Calculating the gravitational pull between two planets is straightforward. Three or more? Famously unsolvable by any simple formula. There is no “correct” answer that satisfies everyone simultaneously. There is only judgment, applied under pressure, in real time.

And consider what I call the Prevention Paradox. In computer science, the Halting Problem tells us it’s impossible to build a program that can always predict whether another program will eventually stop or run forever. In-house counsel face an analogous challenge: their primary job is preventing things that haven’t happened yet. How do you calculate the value of a lawsuit that didn’t occur? How much risk is too much? The problem space is infinite, filled with unknown unknowns.

How Lawyers Already “Solve” Intractability

Lawyers have been managing intractable problems for centuries using the same strategies computer scientists use.

Settlement is a heuristic — a “good enough” solution that avoids the exponential cost of a full trial. If solving the problem costs more than the solution is worth, you settle. It’s not mathematically perfect, but it’s rational.

Summary judgment is scope restriction — pruning the decision tree, removing legal issues from dispute to make the remaining problem smaller and more manageable.

Standard contract templates are what I’d call “tractabilizing” — taking a complex negotiation with infinite possible variations and reducing it to a plug-and-play exercise with known parameters.

Lawyers have been acting as human heuristics, making the intractable manageable, all along. They just didn’t have the vocabulary for it.

How Tractability Informs Our Response to AGI

When AGI arrives, the tractable work (the research, the review, the routine drafting) will be handled by machines, and much of it already is. Lawyers who define their value by those tasks are in trouble.

But the intractable work isn’t going anywhere. Strategic judgment in multi-variable, adversarial, constantly shifting environments. Ethical reasoning at the edges where rules conflict. The human capacity to weigh incommensurable values — justice against efficiency, risk against opportunity, the letter of the law against its spirit — under genuine uncertainty.

You can automate the process of law. You cannot automate the judgment of law.

AGI, when it comes, will be the most powerful tool lawyers have ever had for conquering tractable problems. But intractability isn’t a limitation of current technology. It’s a property of the problems themselves. More computing power doesn’t make the Traveling Salesperson Problem tractable. And more artificial intelligence won’t make the judgment calls of a general counsel or a trial lawyer computable.

Closing Thoughts

I’ve spent a decade building AI tools for the legal industry. I’ve watched AI go from a novelty to a necessity. And I’ll be the first to tell you: the vast majority of what lawyers currently bill for is tractable work that machines will do better, faster, and cheaper.

But the longer I work at this intersection, the more convinced I become that the core of lawyering (the part that actually matters) was never about processing information. It was about making judgments in the face of irreducible uncertainty. About standing in a room and saying, “This is what I believe is right, and here’s why, and I’ll be professionally responsible for it.”

That’s not a tractable problem. It’s not even an intractable one. It’s a human one.

And, that’s not a consolation prize. That’s the point of being a lawyer.

The machines will handle the sand-counting. You handle the judgment.

Tom Martin is CEO & Founder of LawDroid, Adjunct Professor at Suffolk University Law School, and Author of the forthcoming AI with Purpose: A Strategic Blueprint for Legal Transformation (Globe Law and Business). He is “The AI Law Professor” and writes his eponymous column for the Thomson Reuters Institute.

If you want to understand how to reinvent your legal career with purpose and intentionality, and why it’s never too late to embrace innovation, you need to listen to this episode. Robert is at the forefront of global legal transformation and brings a uniquely reflective and hopeful perspective to where the profession is heading.

Transforming a Career, Transforming a Profession

Join me as I interview Robert Dilworth, Executive Director of the Digital Leaders Exchange at the Liquid Legal Institute and Honorary Fellow at Cambridge Judge Business School.

In this insightful podcast episode, Robert shares his remarkable journey from growing up in the Atlanta suburbs to practicing law at Deutsche Bank and Bank of America for nearly three decades, and ultimately reinventing himself in retirement as a global advocate for legal innovation. After relocating to Hamburg, Germany, Robert found himself drawn into the world of legal tech and transformation during the pandemic, and never looked back.

His stories and insights underscore the power of staying curious, embracing optionality, and remaining in motion even when conventional wisdom might suggest otherwise. This episode is a must-watch for anyone who wonders whether their best contributions to the legal profession still lie ahead of them, offering a compelling and practical roadmap for meaningful reinvention at any stage of a legal career.

The Skinny

Robert Dilworth spent 35 years as a corporate lawyer, including 27 years at Bank of America as Managing Director and Associate General Counsel. Rather than retire quietly, he made a deliberate pivot, relocating to Hamburg, Germany, and stepping into a new chapter as Executive Director of the Digital Leaders Exchange at the Liquid Legal Institute, and as an Honorary Fellow at the Cambridge Judge Business School working at the intersection of AI and financial services regulation. Throughout this conversation, Robert reflects on what it means to reinvent yourself with intention, the role that optionality plays in shaping a rich legal career, and why the legal innovation community—filled with hopeful, selfless, and idealistic people—has given him more energy than he ever expected.

His story is a reminder that the best careers don’t end; they evolve.

Key Takeaways

• Robert’s pivot from corporate law to legal innovation leadership was driven not just by a push to leave, but by a genuine pull toward something meaningful and new.

• The Liquid Legal Institute is an independent, neutral, non-profit global think tank with roughly 1,500 members in more than 20 countries, focused on designing a more human-centered and tech-enabled future for law.

• Robert argues that the legal profession is moving from the “weather and the why” of transformation to the “hard yards and the how”—meaning leaders must now focus on practical implementation rather than making the case for change.

• Corporations represent more than 50% of global legal spending, which means corporate clients are increasingly the force driving law firms and in-house teams toward innovation.

• Robert’s mother instilled in him a foundational belief that there was very little he couldn’t accomplish if he put his mind to it—a mindset that enabled him to take risks, embrace optionality, and stay open to unexpected opportunities throughout his career.

• His advice to young lawyers: don’t pre-emptively exclude yourself from opportunities; reach for the opportunity and let life deliver the no.

• The pandemic served as a catalyst for Robert’s transformation, a period of enforced stillness that prompted him to ask what role he could play in improving the legal system and strengthening access to justice.

• Robert describes himself as “a living experiment in radical adaptation,” and encourages peers to see that it is not too late to reinvent themselves if they are so inclined.

• His work mentoring students has been as enriching for him as for those he mentors—perhaps more so.

• The key to sustainability in this new chapter is being selective and intentional about what you say yes to, doing fewer things better rather than spreading yourself thin.

Notable Quotes

1. “Life must be lived forwards, but can only be understood backwards.” - Robert Dilworth, citing Kierkegaard (00:13:53-00:14:01)

2. “Water goes where it’s needed and in different forms. And the legal system is not as agile—it was more rigid than society really needs.” - Robert Dilworth (00:03:19-00:03:34)

3. “I knew I couldn’t go from going 200 miles an hour for decades to going zero miles an hour. But I needed to be in motion.” - Robert Dilworth (00:33:21-00:33:31)

4. “I felt like I’m a living experiment and kind of radical adaptation at my career point in age to kind of pick up everything.” - Robert Dilworth (00:36:37-00:36:47)

5. “I hope other people can see—and people who are my contemporaries can see—that it’s not too late to reinvent yourself if you’re so inclined.” - Robert Dilworth (00:27:01-00:27:05)

6. “Be open to recognizing an opportunity and a break when you see it.” - Robert Dilworth (00:17:36-00:17:44)

7. “I just crafted it so that by the time I left, I felt it’s not just that I’m leaving something—but I also have something that’s pulling me.” - Robert Dilworth (00:31:14-00:31:23)

8. “They inspire me and they give me a lot of energy—hopeful and optimistic, and many of them pretty selfless with some idealism to them, regardless of the decades they may have been working.” - Robert Dilworth (00:40:02-00:40:13)

Clips

Who Really Buys Legal Work

Bar Associations vs. Legal Innovation

Why All The Effort Is Worth It

What The Liquid Legal Institute Does

Robert Dilworth’s story is one of the most quietly profound I’ve encountered in the legal innovation space. He didn’t arrive here by accident or ambition alone. He arrived by staying curious, by allowing himself to be pulled toward something he believed in, and by having the courage to reinvent himself when most people might have simply coasted. His trajectory—from Atlanta suburbs to Columbia and the Sorbonne, through Deutsche Bank and Bank of America, and now to Hamburg, the Liquid Legal Institute, and Cambridge—is a testament to what happens when you stay in motion with intention.

What stands out most is Robert’s insistence that this chapter of his life isn’t a postscript to his career; it is a full and meaningful continuation of it. He is mentoring young lawyers, shaping the direction of global legal innovation conversations, and contributing to interdisciplinary research at Cambridge—not despite having “retired,” but because he approached retirement as a beginning rather than an end.

Closing Thoughts

Robert’s story landed with me on a personal level. As someone who has spent years championing legal innovation, I know how rare it is to find someone who combines deep institutional experience with genuine humility and openness to the new. Robert has both.

What I find most compelling about his journey is the intentionality behind it. He didn’t stumble into this chapter—he built toward it. During the pandemic, he asked himself some hard questions about his role, his purpose, and whether he had more to give. The answer, clearly, was yes. And so he leaned in: promoted innovation culture inside Bank of America before he left, built relationships in the legal tech community, and arrived at retirement with something pulling him forward rather than just pushing him out the door.

For our Legal Rebels community, Robert’s story is a reminder that reinvention isn’t just for the young. The legal profession gives so much to those who commit to it—and those of us who have benefited from that commitment have an opportunity, and perhaps an obligation, to give something back. Whether that’s mentoring a student, championing a new tool in your department, or making a bold career pivot at 60, the door is open.

Stay hopeful. Stay in motion. And never assume the most exciting chapter of your career is already behind you.