Rebekah Tolley: British Art Fair - Keeping Art Human Centric in the Digital Age

This is an episode about what art has always done in moments of technological upheaval: reflect them back to us. Rebekah Tolley curated British Art Fair's first digital art section in 2024, a show that broke records and helped formalize "Digitalism" as a recognized movement. She joins Christine to talk about AI-era artists as this century's surrealists, the echoes of the Industrial Revolution in today's anxieties about work and labor, and why human-centered art matters more, not less, as the tools get stranger — quantum-entangled sculptures, a shaman, and all.

About Rebekah Tolley
Rebekah Tolley is a hybrid artist, filmmaker, and arts educator with 25 years across fine art, photography, and digital media. She curated British Art Fair's first digital art section, helping launch Digitalism as a movement, and is now writing its first history, out next year.

Connect with Rebekah: LinkedIn | British Art Fair

About Christine Kahn

Christine Kahn is a Principal Technical Program Manager with 12+ years of experience across Playlist, Intuit, OpenTable, 20th Century Fox, and Realtor.com, specializing in AI/ML platforms and program delivery. She’s also a published musician and sound bath meditation practitioner. Dreams and Delivery is where she brings both worlds together — real stories from people who deliver at work and dream beyond it.

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This is a conversation about what it actually means to call yourself a builder in the age of AI agents, why judgment and taste turn out to be the scarce resource instead of production nowadays, and how the things you care about outside of work end up shaping what you choose to build.

At the moment in tech careers, tools are changing faster than job titles can keep up. Andrew Cunliffe has been living inside that moment for the better part of a year, building his own fleet of AI tools on nights and weekends while running design on Intuit’s AI+HI Expert Platform by day.

Andrew went from the 82nd Airborne to startup app development to 8 years at Intuit, where he now leads design for the AI expert platform inside QuickBooks and TurboTax. Outside of work, he’s built Raven MCP, an open-source design tool that runs a “taste engine” right inside your workflow instead of a separate canvas, plus HighLvl, a calorie-tracking app built for athletes.

Bonus: Andrew walks through a live demo of Raven MCP and explains why he made the deliberate choice to open-source it.

About Andrew Cunliffe

Andrew Cunliffe is a Senior Staff Product Designer at Intuit, leading design on the AI+HI Expert Platform inside QuickBooks and TurboTax. Outside of work, he builds and open-sources his own AI tools, including Raven MCP, a design system and “taste engine” for AI-assisted product work. Connect with him to see Raven MCP and his other projects in action.

About Christine Kahn

Christine Kahn is a Staff Technical Program Manager with 12+ years of experience across Intuit, OpenTable, 20th Century Fox, and Realtor.com, specializing in AI/ML platforms and program delivery. She’s also a published musician and sound bath meditation practitioner. Dreams and Delivery is where she brings both worlds together — real stories from people who deliver at work and dream beyond it.

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© 2026 Dreams and Delivery LLC. All rights reserved.

This is a conversation about what happens when AI screens resumes before a human ever sees them, why “AI integration specialist” means something different to everyone who says it, and the case for staying a generalist in a market that keeps chasing the next niche. 

We also get into the quiet cost of the specialist bet, how fast a hot skill set can turn cold, and why the people who keep their base skills sharp are the ones still standing when the trend moves on.

Jack Smith started his career installing Windows 95 as a HelpDesk Tech and has spent the years since moving data centers, opening data centers, and learning over and over that the skills worth keeping aren’t the ones tied to a single tool or title.

Now, as AI reshapes hiring on both sides of the table, he’s watching the same mistake repeat itself: companies rolling three jobs into one impossible profile, and candidates rewriting themselves into keyword matches for roles they’ve never actually done.

Bonus: what 25 years of hard-won IT stories taught Jack about learning from failure instead of hiding it — the same instinct that led him to launch his own podcast.

About Jack Smith

Jack Smith is an Infrastructure Project Manager and the host of IT Horror Stories with Jack Smith, a podcast exploring the human side of technology. He spent more than two decades building a career across cybersecurity, data centers, networking, and digital transformation, learning that resilience comes from what you take from failure, not from avoiding it. Outside of infrastructure work, he’s been part of the demo scene — real-time digital computer art on old and new hardware — since 1991.

Connect with Jack: ithorrorstories.eu | LinkedIn | Spotify | Apple | YouTube

About your host
Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.

Connect with Christine: bio.site/dreamsanddelivery | LinkedIn

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The White Belt Founder

This is a conversation about what it's like to be a beginner again on purpose: as a first-time founder, and as a brand-new senior white belt in a taekwondo class full of kids (he and another dad have been dubbed "the Dadvengers"). Lawrence and Christine talk about AI as a force multiplier for solo builders, protecting remote work and family time after years of return-to-office pressure, and why treating the founder journey as a marathon — not a race against every competitor who beats you to market — is the only mindset that holds up.

Just weeks after being laid off from MailChimp, Lawrence Ma has a working beta. Acquire Scout — a platform that aggregates business listings, scores them against a buyer's profile, and walks you through every step of acquiring a small business — is something he built solo, with Claude Max standing in for the three or four engineers a job like this used to take. Some nights that means being up until 2 or 3am, after his kids are asleep.

He's also a brand-new content creator, whose raw first video about his layoff hit 80,000 views and became the accidental springboard for everything else he's building.

About Lawrence Ma
Lawrence Ma is a software engineering manager turned founder, building Acquire Scout after a layoff pushed him to solve a problem he'd hit himself as a business buyer. He's led engineering at two startups and most recently MailChimp. Outside of work, he's a dad of two boys, a recently enrolled martial artist, and new to content creation, sharing the journey in real time.

Connect with Lawrence: Instagram & TikTok @thelawrencema | acquirescout.com

About your host
Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.

Connect with Christine: bio.site/dreamsanddelivery | LinkedIn

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This is a conversation about creating from identity instead of approval: what it looks like to weave your grandfather's WWII story and your family's traditions into work for the next generation, how to use AI as a tool without losing your own voice in it, and the unglamorous research (licensing fine print, ownership rights) that protects years of creative work before you ever publish a thing.

At nine years old, Nicole Rykbos was already building databases for her family's business and making up stories to entertain a houseful of cousins whenever the Nintendo broke. Decades later, those two instincts collided into Sealybooks Studios, a catalog of children's books, music, and animation rooted in Filipino culture, built nights and weekends alongside a full-time tech career.

Bonus: Nicole is currently developing a cat-themed fairy tale series that teaches kids, parents, and grandparents how to spot scams — proof that even the most serious lessons can start with a love-bombing cat prince.

About Nicole Rykbos
Nicole Rykbos is a tech PM and the founder of Sealybooks Studios, where she writes, produces, and animates children's books, music, and family content rooted in Filipino storytelling. She built her career across health communications, healthcare, and fintech before turning Sealybooks from a side project into a full creative catalog. Beyond her own books, she partners with the nonprofit Team Only Stronger on child safety storytelling, including "Warrior Princess Bunny," with proceeds supporting their mission.

Connect with Nicole: Sealybooks.com | Instagram @sealybookstudios | YouTube @sealybookstudios

About your host
Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.

Connect: linkedin.com/in/christinekahn | christinekmusic.com | bio.site/dreamsanddelivery

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© 2026 Dreams and Delivery LLC. All rights reserved.

Exploring the Human-AI Connection

This conversation goes places most AI discussions don't. We get into why most companies don't have an AI problem — they have a human-AI coordination problem — and what that distinction changes about how organizations actually adopt these tools. We also talk about whether AI can dream, what the word "hallucination" reveals about our assumptions, and what it looks like to leave a staff-level role and build something completely your own. Plus: what parenting a two-year-old in the age of AI is teaching him about the things no model can replace.

Aaron Kagan has spent his career studying the gap between how people actually think and how the technologies we build assume they think. At Google, Meta Reality Labs, and Native Instruments, he was asking the same question the whole time — and going independent with GraspingAI gave him the space to finally pursue it on his own terms.

Bonus: the rubber duck analogy that perfectly captures what AI actually does when we think it's being creative.

About Aaron Kagan

Aaron Kagan is founder of GraspingAI, a human-centered AI research and strategy practice, and co-author of An Introduction to the Embodied Mind (Routledge, 2026). He held staff-level UX research roles at Google, Google X, Meta Reality Labs, and Native Instruments, studying how people think, decide, and work with complex technologies. He now helps individuals and organizations build better relationships with AI through research, strategy, and open community workshops.

Connect with Aaron: linkedin.com/in/aaronkagan | graspingai.com

About your host

Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.

Connect: linkedin.com/in/christinekahn | christinekmusic.com

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© 2026 Dreams and Delivery LLC. All rights reserved.

This conversation is about what happens when you realize your TPM and ops skills are already a product and decide to package them. Martina shares the origin story behind Clervio, the fractional operator venture she co-founded with partner Jim Elvidge while navigating her next chapter. We get into the juggle, the mindset shift, and why a friend in Paris funding a writing life through walking tours became a concrete blueprint for what's possible.

Bonus: What crochet teaches you about pacing a transformation.

Martina Ziegenfuss spent years inside big tech turning complexity into execution: post-acquisition integrations, cross-functional programs, operating model design. She's the person you call when things need to actually work.

Then she built something of her own.

About Martina Ziegenfuss

Martina Ziegenfuss is co-founder of Clervio, a fractional operator and enterprise transformation venture, alongside partner Jim Elvidge. She also runs MZConsulting, where she works as a Fractional Chief of Staff for CEOs and leadership teams navigating M&A, operating model changes, and transformation. She previously held cross-functional delivery and operations roles at Intuit and NortonLifeLock.

Connect with Martina: linkedin.com/in/martinaz | clerv.io

About your host

Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.

Connect: linkedin.com/in/christinekahn | christinekmusic.com

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© 2026 Dreams and Delivery LLC. All rights reserved.

This conversation is about what it feels like when your work stops matching your frequency and what it takes to build something completely different. Mary-Lynne also shares how AI agents have reshaped her workflow, freeing her to put her energy where it matters most: the humans in front of her.

Mary-Lynne Williams spent 20 years delivering at the highest levels of tech in Microsoft, Meta, Zillow. Product design, systems thinking, leading teams. By every external measure, she was succeeding.

Then she left to found Buffalo Firefly, a sound healing company now operating in Richmond and Brooklyn.

About Mary-Lynne Williams Mary-Lynne Williams is the founder and CEO of Buffalo Firefly, an energy wellness company bringing sound healing and energy medicine to communities in NYC and Richmond, VA. Before founding Buffalo Firefly, she spent over two decades as a product design leader at Microsoft, Meta, and Zillow, working at the intersection of systems thinking, user experience, and human behavior.

Connect with Mary-Lynne: linkedin.com/in/mary-lynne-williams-4a90932 | buffalofirefly.com

About your host Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.

Connect: linkedin.com/in/christinekahn | christinekmusic.com

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© 2026 Dreams and Delivery LLC. All rights reserved.

This conversation is about what organizational change actually teaches you about personal transformation, how Jess turned a layoff into a launchpad, and what it looks like to build a life outside performance. She also shares her honest take on where AI is and isn’t landing in the change management space.

Jessica Valentine Nelson spent 15+ years inside global organizations: Accenture, Dell, lululemon, helping leaders and teams navigate transformation. She knew the craft of change management from the inside.

Then she went through her own.

About Jessica Valentine Nelson Jessica Valentine Nelson is an executive coach, organizational change consultant, and founder of Guided by Jess Valentine and Full Body Studio. She spent 15+ years at Accenture, Dell Technologies, Optiv, and lululemon helping leaders and teams navigate transformation. Today she runs a coaching practice and a community wellness space in Bastrop County, Texas, and writes about purposeful living on her Substack, Lead with Heart.

Connect with Jessica: guidedbyjessvalentine.com | fullbodystudio.com

About your host Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com, and a musician and soundbath practitioner outside of it.

Connect: linkedin.com/in/christinekahn | christinekmusic.com

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© 2026 Dreams and Delivery LLC. All rights reserved.