Building AI Boston

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Building AI Boston episodes

October 04 Beyond the Prompt: Building Worlds with AI | Michael Gilday
What happens when AI becomes more than a tool and starts becoming part of the creative process itself?
On this episode of Building AI Boston, we sit down with Michael Gilday, Founder, CEO, and Executive Creative Director of Deep Vibe, to explore the evolving relationship between human imagination and artificial intelligence.
Michael’s career has crossed television, radio, advertising, technology, and creative leadership, including early production work on ABC’s Lost and leadership roles at companies including Pegasystems and DataRobot. Today, he and his team at Deep Vibe are exploring an entirely new kind of storytelling through Taste Networks, The District, and WRXLnoise, where AI characters, shared memory, custom technology, and human creative direction come together to build living fictional worlds.
We talk with Michael about why taste, context, and human judgment may become even more important as AI gets more powerful, how small creative teams can now build experiences that once required massive organizations, and why the conversation around AI shouldn’t only focus on what might go wrong, but also on what humans might be able to create.
We also explore Boston’s role in the rapidly growing AI ecosystem, the importance of bringing technologists and creatives together, and what Michael believes the next generation of AI-powered storytelling and experiences could look like.
Can AI amplify human imagination rather than replace it? And are we entering an era where stories no longer have to end?
Join us for a conversation about creativity, technology, storytelling, and the possibilities emerging when humans and AI build together.
Building AI Boston explores the people, companies, ideas, and technologies shaping the future of artificial intelligence in Boston and beyond.

Learn more about Michael Gilday & Deep Vibe:
Deep Vibe: https://www.deepvibe.com
Michael Gilday on LinkedIn: https://www.linkedin.com/in/gildaymonster/
Connect with Building AI Boston:
Website: https://www.buildingaiboston.com
YouTube: https://www.youtube.com/@BuildingAIBoston
Apple Podcasts: Building AI Boston on Apple Podcasts
LinkedIn: Building AI Boston on LinkedIn
Building AI Boston is a proud media partner of Boston AI Week:
https://aiweek.boston

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49 min
September 21 The Open Accelerator: Turning AI Ideas Into Scalable Companies | Guest Stefanie Chiras
Boston has no shortage of people building ambitious AI products. The harder part is turning those ideas into companies and technologies that can actually work, scale, and succeed inside an enterprise.
That’s where the The Open Accelerator comes in. The new Massachusetts initiative is designed to help early-stage AI companies bridge the gap between promising prototypes and real-world adoption.
Our guest, Stefanie Chiras, brings an unusually deep perspective to that challenge. She began her career working on the materials and technology inside silicon chips, moved progressively up the technology stack, and eventually led major businesses and ecosystem work at Red Hat. Today, she is helping build the Open Accelerator around many of the same principles that made open source transformative: shared knowledge, strong communities, clear standards, and the idea that innovation gets better when more people can contribute.
The Open Accelerator brings together Red Hat, the Massachusetts AI Hub, IBM Ventures, founders, investors, technical experts, and others across the Massachusetts innovation ecosystem. Its 16-week residency gives selected AI startups access to business and technical mentors, enterprise expertise, connections, and a community designed to help them move faster without requiring them to give up equity simply to participate.
We dig into:
• Why AI has dramatically accelerated the journey from idea to prototype, but not necessarily from prototype to successful product
• What open source can teach us about building AI communities and ecosystems
• Stefanie’s journey from materials science and silicon chips to software, product leadership, and the Red Hat ecosystem
• How Red Hat helped make open-source technology enterprise-ready, and why that history matters for AI startups today
• Why Boston and Massachusetts have an opportunity to become a place where people not only come to learn, but stay to build and grow
• How the Open Accelerator helps founders with enterprise technology, sales, mentorship, connections, and funding opportunities
• Why participation in the accelerator does not require founders to give up equity
• What the Open Accelerator’s first cohort is teaching the team, and what comes next
• Why strong guardrails can actually encourage AI experimentation rather than restrict it
• The role government, universities, companies, investors, and community organizations can play in creating a stronger AI ecosystem
This conversation is about what happens after the prototype. It’s about the infrastructure, expertise, relationships, and community that help good ideas become viable companies, and why Massachusetts may be particularly well positioned to build that kind of ecosystem.
LINKS:
https://the-open-accelerator.com

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40 min
September 11 Boston AI Week with Judah Phillips
What does it take to build an AI ecosystem that starts in one place but reaches far beyond it?
That’s the idea behind Boston AI Week, the community-driven festival Judah Phillips created to connect companies, academics, investors, government, cultural institutions, job seekers, students, and people who are simply curious about AI.
Judah is Chief AI and Product Officer at Market Holdings and has been building AI communities in Boston for years. This year, Boston AI Week includes more than 500 participating organizations and more than 150 events, with visitors and delegations coming from 23 countries. Boston is the home base, but increasingly it isn’t the boundary.
What makes the event unusual is the model. Judah deliberately rejected the traditional conference format in favor of something decentralized, largely free, and built by the community itself. He describes it as a “civic action.”
Building AI Boston is part of that ecosystem too: Kara serves on the Boston AI Week board, and Kara and Anna will be on site as official media partners.
We dig into:
• Why an AI ecosystem can’t just be software companies talking to other software companies
• The four goals behind Boston AI Week: broaden understanding, create jobs, connect the ecosystem, and strengthen the Massachusetts economy
• Why Judah built a decentralized festival instead of a traditional conference
• Why keeping most events free matters to the mission
• How Boston AI Week became an international draw
• The career fair, and why job creation matters in a conversation often dominated by job loss
• Judah’s bigger ambition to make AI part of business, culture, community, and everyday life
• Why he prefers “humans in control” to simply “human in the loop”
This conversation is really about who gets to participate in the AI economy, how you build the connections that make an ecosystem work, and what happens when you invite a much bigger group of people into the conversation.
Boston AI Week https://aiweek.bostonBoston AI Week Schedule: https://aiweek.boston/scheduleJudah's Linkedin: https://www.linkedin.com/in/judahphillips

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51 min
June 15 Authentic AI Marketing with Molly Mahoney on Building AI Boston
In this exciting episode of Building AI Boston, hosts Anna and Chris sit down with AI marketing strategist, speaker, and entrepreneur Molly Mahoney to explore how artificial intelligence is transforming the way businesses connect, communicate, and grow.
Known as “The Prepared Performer,” Molly has helped thousands of entrepreneurs leverage AI, content creation, and authentic storytelling to build profitable businesses while staying true to their unique voice. Her viral content has generated millions of views, and she has been featured in Forbes, Entrepreneur, Inc., and major marketing conferences around the world.
During this conversation, Molly shares:
• How to use AI without sounding robotic
• The future of content creation and marketing
• Why authenticity matters more than ever in the AI era
• Building meaningful relationships with AI-powered tools
• AI workflows that save time and increase impact
• How entrepreneurs can stand out in a world flooded with AI-generated content
• Why your “weird” may be your greatest competitive advantage
Whether you’re an entrepreneur, marketer, creator, business leader, or simply curious about the future of AI, this episode is packed with actionable insights and inspiration.
SPECIAL GIVEAWAY:
Molly.live/aiboston
Learn more about Molly Mahoney:
https://www.mollymahoney.com
The Prepared Performer:
https://www.thepreparedperformer.com
Listen to more episodes of Building AI Boston:
https://www.buildingaiboston.com
Subscribe for more conversations with the leaders shaping the future of artificial intelligence.

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45 min
June 01 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.

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37 min
May 27 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

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30 min
March 29 “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.

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33 min
March 11 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.

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40 min
March 02Reimagining 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
Listen Phirst™ Platform: https://listenphirst.com
Sheila's Open Letter to the CEO of 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.

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32 min
December 19, 2025 The future of workflow with Andie Dovgan
In this episode of Building AI Boston, we sit down with Andie Dovgan, Chief Growth Officer at Creatio, a Boston-based unicorn CRM and workflow automation company, to explore what happens when AI moves beyond pilots and hype and starts reshaping real business workflows.
Andie breaks down the difference between AI as an assistant and agentic AI — autonomous systems capable of executing entire workflows — and why the future of work depends on how well organizations combine digital talent with human judgment.
We dive into:
• Why AI is an economic shift, not just a technology trend
• What most leaders get wrong about “job replacement” narratives
• How CRM is being reimagined to reduce friction and increase insight
• Why no-code tools empower business teams to adapt faster — without waiting on IT backlogs
This is a conversation about building systems that work in the real world — and a reminder of what Boston does best: turning big ideas into practical impact.

Guest
Andie Dovgan
Chief Growth Officer, Creatio
🔗 Creatio Website: https://www.creatio.com
🔗 Andie Dovgan on LinkedIn: https://www.linkedin.com/in/andiedovgan/

#BuildingAIBoston
#AgenticAI
#AIInBusiness
#FutureOfWork
#NoCode
#CRM
#BostonTech

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37 min

About Building AI Boston

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“Building AI Boston” is a dynamic and engaging show dedicated to exploring artificial intelligence (AI) through open, inclusive conversations. Centered in Boston, a hub of innovation and technological…

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