The future of workflow with Andie Dovgan

AI Built for Law: Thomson Reuters CPO David Wong on why purpose-built tools matter in legal

AI is really good at coming up with plans. It's not always great at executing them. David Wong thinks that gap is the whole story for legal AI right now, and it's why Thomson Reuters has been building the way they have. David is Chief Product Officer at Thomson Reuters, which has been around for over a hundred years and is one of the most established names in legal information. He leads CoCounsel, their AI platform, which recently hit 1 million users across 107 countries. He also just published a widely read Fortune piece laying out his framework for where legal AI is heading. We recorded the day after Anthropic launched Claude for the Legal Industry, with both Thomson Reuters and Descrybe included as MCP connectors. So this is a conversation about what it looks like when a 100-year-old company and a three-year-old startup end up in the same lineup, and what separates purpose-built legal AI from generic tools. We dig into: • The plan vs. execution gap at the center of David's Fortune piece, and why generic AI tools often stumble at the second part • The "wrong tool for the problem" framing, and why hallucination isn't the real risk; choosing the wrong tool is • Why both Descrybe and Thomson Reuters count as purpose-built tools, even though they sit at very different ends of the legal tech market • Thomson Reuters's "we replaced ourselves" moment: rebuilding Westlaw on a generative AI foundation, and why staying still wasn't an option • The PC software ecosystem analogy David uses to explain where this is all heading, and why no single AI company is going to write every legal application • Claude as orchestrator, not soloist: what it looks like when frontier AI delegates to a "team of specialists" through MCP connectors • The access to justice payoff both ends of the legal tech market are betting on David has been at the front of Thomson Reuters's AI strategy from the beginning, and his Fortune piece moved a chunk of the current debate about how AI actually executes on legal work. But this conversation stays grounded in customers, coexistence, and what it actually takes to ship this stuff responsibly at scale.

Boston Tech Week with Rose Johnson on Building AI Boston

Traditional conferences put everyone in one venue and hand them a ticket. Tech Week flips it: hundreds of events across a city, hosted by whoever wants to host, all on a single calendar. Rose Johnson thinks this format gives the power back to creators, and Boston is about to find out what that looks like. Rose is a marketing partner at Andreessen Horowitz, where she leads Tech Week, a16z's decentralized conference series that started in LA in 2022 and has expanded to four cities. Boston is the newest. They set an internal goal of 500 events for the debut. They blew past 600. We recorded ahead of Boston Tech Week (May 26 to 31), which runs back-to-back with New York Tech Week so attendees can do both. This is a conversation about why Boston was the next city, what a "platform not organizer" model actually looks like, and what to expect when 600 plus events take over a town that's never done this before. We dig into: The origin story of Tech Week, from a post-COVID LA experiment in 2022 to a four-city circuit Why the decentralized format works, and why "power back to the creators" is the whole point Boston's response, well past the internal 500-event target, with deep tech and biotech sharing the calendar with hackathons for marketers What it means to treat Tech Week as a platform rather than a conference, with hosts setting the format and a16z staying out of the way The "renaissance, not revolution" framing, and why collaboration between cities matters more than rivalry How each city develops its specialization, from LA's entertainment AI and defense clusters to whatever Boston ends up becoming known for Practical advice for founders, students, and curious newcomers on how to navigate 600 plus events with a mindset of abundance Rose has been on the Tech Week team since the beginning and has watched it go from one LA experiment to a four-city circuit that companies like Anthropic, OpenAI, and Axios now return to year after year. But this conversation stays grounded in Boston specifically: the calendar, the hosts, the people showing up, and what the city gets to put on the map. Learn more about Boston Tech Week: https://www.tech-week.com/boston View the official Boston Tech Week schedule: https://www.tech-week.com/calendar/bo... Learn more about Rose Johnson at a16z: https://a16z.com/author/rose-johnson/ Boston Tech Week is presented by a16z and is scheduled for May 26 to May 31, 2026, with events hosted by companies and organizations throughout the city. Rose Johnson is listed by a16z as a marketing partner supporting Tech Week for a16z speedrun. Tech Week calendar + dedicated tracks: tech-week.com/calendar/boston Tech Week website: www.tech-week.com speedrun: a16z.speedrun.com Tech Week socials X: https://x.com/Techweek_ LinkedIn: / tech-week-a16z Instagram: / techweeka16z My linkedin if you need it: / rosejohnson32

“It’s About Us” with guest Bryan Reimer, Research Scientist at MIT

Most AI conversations start with the technology. Bryan Reimer thinks that's exactly the problem. A research scientist at MIT and global expert on AI, human behavior, mobility, and public policy, Bryan joins us to talk about his new book, How to Make AI Useful, and the thesis that cuts through the noise: the technology was never the point. We are. In this episode of Building AI Boston, we get into autonomous vehicles as a live case study in what happens when deployment outpaces policy, trust, and common sense — and what that tells us about where generative AI is headed next. We dig into: * Why 80% of today's generative AI advancements may already be beyond what businesses can actually use * What autonomous vehicles reveal about what happens when technology outruns policy — and why the next major incident isn't an if, it's a when * How to think about AI as a co-pilot, not an autopilot — and what gets lost when we confuse the two * The difference between the "wow" and the "whoa" in AI adoption * Why Bryan is betting on the wet computer — the brain between your ears — for a long time to come * What AI2030 is building to make sure the responsible side of this conversation doesn't get drowned out Bryan has advised transportation leaders at the federal level, including serving as vice chair of the AI subcommittee under Secretary Pete Buttigieg. But this conversation stays grounded — in the practical, the personal, and the question of whether we are going to let AI change us.

The Ethical AI Puzzle with guest Cansu Canca on Building AI Boston

What does it mean to build AI that actually works? Not just technically, but for the people it touches. In this episode of Building AI Boston, we sit down with Cansu Canca, philosopher, Founder and Director of the AI Ethics Lab, and Director of Responsible AI Practice at Northeastern University, to talk about why getting AI ethics right is less about adding a policy at the end and more about how you build from the start. Cansu came to AI ethics through philosophy, public health, and law — fields where the stakes are high and the time to decide is short. That combination shaped her belief that ethical thinking is not a luxury or a slowdown. It is how you get to better technology. We dig into: • Why every AI system already reflects someone's values, whether you planned it or not • What autonomy, fairness, and harm reduction actually look like when you move from principle to practice • Her Puzzle-solving in Ethics (PiE) Model for working through ethical questions in real time, when there is no perfect answer and no time to wait • How bias in your model is often just a sign that your model is not doing its job • Why academia is one of the few places left that can ask hard questions without a product to protect • What responsible AI governance inside a university looks like when you are the builder, the buyer, and the classroom all at once Cansu has advised the UN, Interpol, the World Health Organization, and the World Economic Forum. But this conversation stays grounded — in the practical, the urgent, and the question of who is actually in the room when these decisions get made.

Reimagining Healthcare in the Age of AI with Sheila Phicil

What happens when we introduce powerful new technology into a system that was already failing the people it was built to serve? That is the question at the heart of this conversation. In this episode of Building AI Boston, we sit down with Sheila Phicil, social change futurist, founder of Phicil-itate Change™, and author of the forthcoming book Remembering How to Care: Reimagining Healthcare in the Age of AI, to explore what it will truly take to redesign healthcare from the bottom up. Sheila's journey began in Port-au-Prince, Haiti, where a volunteer medical mission taught her that even the best-intentioned care can miss the mark entirely. That lesson, listen first and design second, has driven nearly two decades of work inside institutions like Dana-Farber Cancer Institute and Boston Medical Center, and now sits at the core of everything she builds. We dive into: * Why the U.S. spends the most on healthcare yet ranks last in life expectancy among developed nations and what structural forces are really driving that gap * How the SEEDS of Innovation™ Framework helps health systems get to the root of the problem instead of repeating the same costly mistakes * The Listen Phirst™ platform: using voice AI to collect lived experience at scale and center the voices of the most vulnerable in innovation decisions * Why digital health fails at a 98% rate and what that tells us about introducing AI into already strained systems * The coming collision of rising unemployment, shrinking healthcare coverage, and burnt-out providers * Data sovereignty and why your health data is an extension of your identity, belongs to you, and should be treated as the asset it is * Why the people experiencing the most pain are the ones best positioned to drive the innovation Sheila also shares her open letter to the CEO of Anthropic on how current AI models risk undermining human sovereignty and makes the case that the most urgent question of our time is not how to build smarter AI, but who gets to decide what health, safety, and care actually mean. This is a conversation about listening, equity, and what it looks like to walk up to the top of the river and ask why people are falling in. The future of healthcare will not be designed by the system. It will be built by listening to the people living it. ____________________________________________________________________________   Sheila Phicil, MPH, MS, PMP, FACHE | Social Change Futurist ™ | 4x Founder  Phicil-itate Change: https://phicil-itatechange.com [https://phicil-itatechange.com/] Listen Phirst™ Platform: https://listenphirst.com [https://listenphirst.com/] Sheila's Open Letter to the CEO of Anthropic: https://helpthisbook.com/sheila-phicil/open-letter-to-anthropic [https://helpthisbook.com/sheila-phicil/open-letter-to-anthropic] Guest Bio  Sheila Phicil is a Social Change Futurist™ with nearly two decades of experience shaping healthcare innovation. She is the founder of Phicil-itate Change™, an innovation studio helping startups, investors, and health systems implement ethical, patient-centered solutions. She’s held leadership roles at Brigham and Women’s Hospital, Dana-Farber Cancer Institute, and Boston Medical Center, where she served as Director of Innovation for the Health Equity Accelerator. She developed the SEEDS of Innovation™ Framework and launched Listen Phirst™, a platform translating patient stories into actionable insights, while advancing data sovereignty through consent and compensation. A first-generation Haitian American, Sheila launched her first nonprofit at age 14. She holds dual master’s degrees from Boston University, is a PMP and FACHE, and has received multiple leadership honors. She is a sought-after speaker and a published contributor to journals including JAMA Oncology. Her forthcoming book, Remembering How to Care: Reimagining Healthcare in the Age of AI, explores reimagining healthcare in the age of AI.