AI-Curious with Jeff Wilser

Jeff Wilser
  • 4.9 (24)
  • TECHNOLOGY
  • UPDATED WEEKLY

A podcast that explores the good, the bad, and the creepy of artificial intelligence. Weekly longform conversations with key players in the space, ranging from CEOs to artists to philosophers. Exploring the role of AI in film, health care, business, law, therapy, politics, and everything from religion to war.  Featured by Inc. Magazine as one of "4 Ways to Get AI Savvy in 2024," as "Host Jeff Wilser [gives] you a more holistic understanding of AI--such as the moral implications of using it--and his conversations might even spark novel ideas for how you can best use AI in your business."

  1. 1D AGO

    AI Adoption Case Study Masterclass, w/ WCCB’s Krista Snelling & Matthew March

    What does it take to make AI adoption stick in a high-stakes, heavily regulated industry, without triggering job-loss panic? In this episode of AI-Curious, we have a hyper-specific case study of AI adoption. Host Jeff Wilser talks with Krista Snelling (CEO and Chairman) and Matthew March (CIO and EVP) of West Coast Community Bank about their practical playbook for rolling out AI the right way: governance first, culture second, and measurable wins that free up time without cutting headcount. Why this is something of a “very special episode”: The story and success of the West Coast Community Bank is something that Jeff knows personally. Jeff was honored to visit WCCB’s headquarters and work with their leadership team on AI culture and AI strategy, helping to transform curiosity into clarity. In this podcast for the first time, Jeff peels back the curtain to share the AI and Leadership workshops he conducts for businesses.  Special thanks to Vistage Chair Richard Bell and the larger Vistage community.  Guests Krista Snelling — CEO and Chairman, West Coast Community Bank Matthew March — CIO and EVP, West Coast Community Bank Key topics we cover 00:37 — Why we’re sharing this case study and what “curiosity-driven” adoption looks like06:58 — Bank scope and context: footprint, size, and what makes this implementation notable10:29 — When AI shifted from “vaporware” to something teams could use right now15:23 — The banking reality: protecting customer data and operating in a regulated environment17:43 — Governance first: policies, model risk management, and third-party/vendor risk23:02 — The “Curiosity Canvas,” the “drudgery dump,” and targeting tedious work for automation25:14 — Building an AI Working Group across departments and flipping the pyramid33:51 — Making adoption repeatable: SharePoint collaboration, prompt sharing, Teams channel support36:24 — A concrete workflow win: extracting data from PDFs to generate letters automatically39:19 — Another win: scraping hundreds of statements for key data elements in a fraction of the time42:21 — System conversion regression testing: validating outputs at scale with better traceability44:35 — Security approach: approved tools, tenant controls, DLP settings, and “what not to use AI for”49:29 — A hard boundary: avoiding AI for anything that directly impacts financial reporting52:11 — The culture message: “efficiency, not reduction,” and why that unlocks curiosity53:02 — Advice for leaders: start small, build momentum, and appoint an internal champion56:51 — Quick personal use cases: everyday ways they use AI outside the officeFollow AI-Curious on your favorite podcast platform: Apple Podcasts Spotify YouTube All Other Platforms Vistage Chair Richard Bell: https://app.vistage.com/sites/s/chairs/0038000000sllSFAAY/richard-bell West Coast Community Bank: https://app.vistage.com/sites/s/chairs/0038000000sllSFAAY/richard-bell For anyone interested in Jeff’s AI Workshops for their company: Reach out directly at jeff@jeffwilser.com

    59 min

  2. FEB 12

    Deep-Dive Into Agentic Workflows, w/ Cognizant’s Head of AI

    What happens when software stops just “chatting” and starts acting in the real world, across real workflows, with real consequences? In this episode of AI-Curious, the Head of AI at Cognizant goes deep on AI agents and agentic workflows: what they are, why enterprises are investing heavily, and what it actually takes to make agent systems reliable and safe at scale. We unpack what separates an AI agent from a traditional chatbot, why “agency” changes the stakes, and how multi-agent systems can be designed to reduce risk instead of amplifying it. We also explore concrete enterprise use cases, including agent hierarchies that coordinate across complex systems (like networks, utilities, and other operations), plus how “agentic process automation” builds on older automation models while adapting to unexpected edge cases. Finally, we zoom out to the future of work: which tasks get augmented first, why disruption is happening faster than most forecasts, and how trust in AI systems may shift over the next several years. Guest Babak Hodjat — Head of AI at Cognizant; leads AI lab work focused on scaling reliable, trustworthy agent systems; longtime AI builder with deep experience in applied natural language systems.  Key topics we cover 07:00 — What an AI agent is (and how it differs from a chatbot)13:03 — State of play: what’s working, what’s not, and why “agent systems must be engineered”17:00 — A practical multi-agent design pattern across telecom, power, and agriculture20:28 — Agentifying rigid processes (and handling unforeseen situations)24:14 — Who should deploy agents, why single “do-everything” agents are risky26:34 — An open-source starting point for experimenting with multi-agent systems29:12 — Guardrails: reducing hallucinations, adding redundancy, and safety thresholds35:29 — Why we should use LLMs for reasoning, not knowledge retrieval38:15 — The future of work: tasks, jobs, and decision-making roles shifting upward41:59 — AGI, limitations, and why modular multi-agent systems may matter44:57 — A prediction: we’ll delegate more than we expect as systems become more trustworthyFollow AI-Curious on your favorite podcast platform: Apple Podcasts Spotify YouTube All Other Platforms

    47 min

  3. FEB 5

    The CEO of Upwork, Hayden Brown: AI is Creating Jobs, Not Killing Them

    Is AI quietly creating more work than it’s replacing, and are we measuring the job market the wrong way? In this episode of AI-Curious, we talk with the CEO of Upwork, Hayden Brown, about what the platform is seeing across the global freelance economy, and why the “AI is killing jobs” narrative can miss what’s happening at the edges of the market. We also dig into how to adopt AI inside an organization without just “sprinkling fairy dust” on old workflows, and what it takes to make AI rollout a cultural shift, not just a tooling upgrade. Guest Hayden Brown is the CEO of Upwork, the global work marketplace connecting businesses with freelance talent across knowledge-work categories. We discuss Upwork’s vantage point on hiring trends, the rise of fractional work, and what AI-driven change looks like when companies redesign workflows end-to-end rather than retrofitting existing systems. Key topics we cover 03:50 — A global background and why opportunity access shapes the mission05:27 — The scale of Upwork and why freelancing is a major part of the economy07:14 — How we approached AI adoption as a structured, company-wide program08:47 — Early “two-year vision” ideas that reshaped marketing and product workflows11:34 — Reducing fear: how we framed AI internally, including room for mistakes16:03 — Building an AI agent experience (and what it changed about job posts)17:14 — Why “reinventing, not retrofitting” separates AI winners from strugglers22:24 — Why macroeconomics can explain more than AI in hiring slowdowns23:01 — The core claim: AI creating more opportunities than it’s destroying24:05 — Fractionalization: how full-time jobs get broken into AI + human slices25:09 — A concrete example of humans working alongside AI in production workflows26:32 — From “prompt engineer” to “AI generalist”: orchestration becomes the ask28:11 — Why the AI jobs debate is too binary, and what’s getting missed31:43 — Practical reskilling: embedded experts who train teams while upgrading systems36:29 — AI’s impact across unexpected categories, including creative work39:15 — Five-to-ten-year outlook: humans as orchestrators, premium on human skills43:22 — Career advice for early-career listeners in an AI-shaped job market45:40 — Real-life AI use: editing, learning, and replacing the blank page problem Follow AI-Curious on your favorite podcast platform: Apple Podcasts Spotify YouTube All Other Platforms

    49 min

  4. FEB 2

    How to Make Human-First Tech Decisions, w/ Tech Humanist Kate O’Neill

    What does “human-first AI” actually look like when you have to make decisions under pressure, hit numbers, and keep trust intact? In AI-Curious, we talk with Kate O’Neill — “the Tech Humanist” and author of What Matters Next — about how leaders can adopt AI in ways that strengthen human outcomes instead of quietly eroding culture, morale, and customer experience. We dig into why so many AI initiatives fail for non-technical reasons, how to think beyond short-term wins, and why prompting is less “prompt engineering” and more like learning to delegate clearly. Key topics: Prompting as delegation: defining success conditions, constraints, and what “good” means (00:00) Kate’s early work at Netflix and what personalization taught her about human impact (04:45) What “human-unfriendly” tech looks like in practice, from subtle friction to scaled harm (09:28) The Amazon Go example: how small design constraints can scale into behavior change over time (11:19) AI in the workplace: why “cut, cut, cut” is shortsighted, and what gets lost when you optimize only for this quarter (14:14) Trust and readiness: why reskilling fails when people don’t believe there’s a future for them (16:45) The now–next continuum: making decisions that “age well,” not just decisions that look good immediately (17:29) Preferred vs. probable futures: identifying the delta and acting to move outcomes toward what you actually want (19:22) “Chatting with Einstein”: using AI to become smarter vs. outsourcing thinking (22:13) Why most AI pilots fail: human and organizational readiness, not the tech itself (24:02) Questions → partial answers → insights: building an organizational muscle that compounds (28:21) Bankable foresight: why Netflix invested early in what became streaming (30:37) Trend watch: the pivot from LLM hype to agentic AI, and why prompting still matters (38:58) Sycophancy and “best self” prompting: getting better outputs by being explicit and structured (41:01) Probability vs. meaning: what LLMs can do well, and what they can’t replace (44:45) A fun real-world workflow: Kate’s Notion + AI system for hotel coffee-maker recon (46:26) Career advice in the AI era: adaptability, “human skills,” and shifting definitions of value (49:21) Guest Kate O’Neill is a tech humanist, founder and CEO of KO Insights, and the author of What Matters Next: A Leader’s Guide to Making Human-Friendly Tech Decisions in a World That’s Moving Too Fast. She advises organizations on improving human experience at scale while making emerging technology commercially and operationally real. KO Insights: https://www.koinsights.com/about-kate/ Follow AI-Curious on your favorite podcast platform: Apple Podcasts Spotify YouTube All Other Platforms

    53 min

  5. JAN 22

    Deep-dive on AI and Creativity, with The Man Designing the World’s Creative Tools (Eric Snowden, Adobe’s SVP of Design)

    What happens when the world’s most-used creative tools get smarter — and creators worry they’re losing the wheel? In this episode of AI-Curious, we talk with Eric Snowden, Senior Vice President of Design at Adobe, about how Adobe is weaving AI into Photoshop, Lightroom, Acrobat, and beyond — while trying to keep the tools respectful of craft, muscle memory, and the human spark. We dig into the bigger question beneath the feature releases: as AI accelerates creation, do we get more powerful… or do we become passengers approving machine outputs? Key topics: Two buckets of Adobe AI: upgrading existing tools vs building net-new AI products (00:04:55) Photoshop “harmonize,” Lightroom auto culling, and Acrobat “PDF spaces” (00:04:55) Why PDFs are a bottleneck for knowledge work, and how Acrobat can help you “get 80% of the way there” (00:07:18) Project Graph explained: node-based workflows that stitch together building blocks like Firefly and Photoshop (00:08:25) A concrete Project Graph example: 2D product photo → 3D asset → generated ad → multiple animated versions, with the user still in control (00:09:42) Time saved vs creating more: how Firefly helped Adobe teams move faster and “make more things,” including “like 40% improvement” on time-to-market (00:14:28) A Max London demo that captures the core principle: “his hand was on the wheel” (00:17:45) “Quiet AI” in practice: enhanced audio in Adobe Podcast that can make phone-recorded audio sound studio-ready (00:19:57) Respecting creative muscle memory: why “subtraction is not always good,” and why Adobe adds new workflows without removing old ones (00:24:43) Firefly’s principles: licensed content, knowing what’s in the model, and compensating creators (00:29:29) Content authenticity as a “nutritional label for AI”: immutable metadata describing what was done to an image (00:30:15) The self-driving car analogy: creators need to be able to “grab the wheel” and tweak under the hood (00:36:00) Vibe coding inside Adobe: designers using Cursor and internal tooling to build prototypes that hit real APIs (00:39:18) A leadership playbook for AI adoption: focus the OKRs, make training practical, show examples, remove roadblocks (00:44:19) The future of AI creative tools: communicating intent beyond text prompts, and shifting from “look what I do with AI” to storytelling (00:46:36) Guest Eric Snowden is the Senior Vice President of Design at Adobe, overseeing design and the AI-infused creative tools used by millions of creators. Mentioned in this conversation Adobe Firefly Project Graph (node-based creative workflow building) Enhanced audio in Adobe Podcast Content authenticity / provenance metadata (“nutritional label” concept) Cursor and “vibe coding” for rapid prototyping inside enterprise teams Follow AI-Curious on your favorite podcast platform: Apple Podcasts Spotify YouTube All Other Platforms

    50 min

  6. JAN 15

    AI Broke the Web’s Social Contract, w/ Tony Stubblebine, CEO of Medium

    What happens when AI can “read the whole internet” but the internet stops volunteering its best work? In this episode of AI-Curious, we talk with Tony Stubblebine, CEO of Medium, about what he calls AI’s “broken social contract” with the web, and why the next era may be less about a “dead internet” and more about a dead public internet. We unpack the incentives that made the open web thrive, how AI search summaries change the traffic bargain, and what a realistic path forward could look like for publishers, platforms, and writers. Key topics we cover: -Why generative AI broke the web’s old value exchange, and what “social contract” means in practical terms (00:03:24) -Tony’s “three Cs” framework for a healthier AI ecosystem: consent, credit, compensation (00:05:13) -The publisher response spectrum: blocking crawlers, fighting spam/slop, and what happens if collaboration fails (00:04:25) -The shift from public publishing to private communities (Discords, group chats, newsletters) and what drives that retreat (00:07:06) -How AI search summaries can cut the incentive to publish publicly by reducing click-through and traffic (00:08:21) -Why AI systems still depend on human source material, and what happens when the best content moves behind “closed doors” (00:09:27) -Cloudflare’s role in the escalating crawler arms race, including large-scale blocking and other countermeasures (00:16:48) -A proposed solution: an internet-wide licensing standard instead of one-off deals, including the Really Simple Licensing (RSL) approach (00:18:07) -What “paying creators” could look like in practice, including opt-in/opt-out controls and better transparency for writers (00:19:33) -“Dead internet theory” vs. the more plausible outcome: a dead public internet, and why Tony is cautiously optimistic about a new equilibrium (00:23:06) -The “second wave” of AI: moving from replacement to augmentation, and how Medium is thinking about AI tools that support flow state rather than write for you (00:26:03) -Why AI detectors don’t solve the problem, and why Medium focuses on quality and reader value as the enforceable standard (00:34:04) -Advice for writers: the difference between the creator economy and the “expert economy,” and what’s likely to be more sustainable (00:38:43) -Tony’s prediction: “trust but verify” becomes the balance point, and the web finds an equilibrium because AI can’t function without public sources (00:43:27) Guest Tony Stubblebine is the CEO of Medium and a leading voice on the evolving relationship between generative AI and the open web. Mentioned in this conversation Medium’s framework: Consent, Credit, Compensation Follow AI-Curious on your favorite podcast platform: Apple Podcasts Spotify YouTube All Other Platforms

    47 min

  7. JAN 8

    The “Talk With Einstein” AI Rule You Should Follow, w/ New Yorker Cartoonist Victor Varnado

    Is AI making creators more powerful… or more replaceable? And if you start with a blank page for a living, there’s an even sharper question underneath it: should AI write for you… or write with you? In this episode of AI-Curious, we sit down with Victor Varnado—a New Yorker cartoonist, comedian, actor, and creative technologist—to explore a grounded, practical philosophy for using AI without becoming a passenger. Victor draws a sharp line between generative AI (press a button, get “a masterpiece”) and what he’s more interested in: transformative AI—tools that take messy raw material (notes, transcripts, half-ideas) and turn it into something structured enough to revise. We also talk about how taste becomes a real moat in an AI-saturated world, why “vibe coding” can go sideways fast when you don’t understand the domain, and how Victor’s accessibility-first mindset shapes everything he builds. Along the way, Victor breaks down his tools—including Magic Bookifier and the Writing Coach—designed to get writers from zero to first draft faster through guided questions and structured interviews. He frames the goal with a concept he calls cognitive discourse: using AI like a thinking partner that makes you sharper, not a crutch that makes you lazier. His metaphor is perfect: do you talk with Einstein and get smarter… or do you just hand Einstein your homework? We wrap by looking at Victor’s newest effort, BrightWrite, which aims to bring structured, supportive AI into education—especially for students facing cognitive or creative barriers. Victor also shares discount/freebie codes for listeners who want to try his tools, and we’ll include the specifics in the show notes and links. Topics we cover: Victor’s multi-hyphenate path: comedy, New Yorker cartoons, production, and techWhy “transformative AI” is more useful than one-click generative outputThe Writing Coach approach: structured interviews that turn your ideas into drafts“Cognitive discourse” vs. “cognitive offload” (and the Einstein metaphor)Why taste may be the creative moat in an AI-heavy worldThe risks of “vibe coding” outside your expertiseBrightWrite and the promise (and limits) of accessibility-first AI in educationPractical ways to use AI for writing, revision, and everyday communicationGuest: Victor Varnado Tools mentioned: Magic Bookifier, Writing Coach, BrightWrite

    41 min

  8. JAN 1

    The New Year Reality Check: Who’s Really Adopting AI, w/ Ramp Economist Ara Kharazian

    What’s actually happening with AI adoption inside U.S. businesses—and how much of the public discourse is just vibes? In this episode of AI-Curious, we dig into the hard numbers behind AI spend and adoption with Ara Kharazian, an economist at Ramp and the leader of Ramp Economics Lab. Using anonymized, real-time corporate spend data across tens of thousands of businesses, Ara shares what the “receipts” reveal about who’s buying AI, how fast budgets are shifting, and where the hype diverges from reality. What we cover Ramp’s unique vantage point: why transaction-level corporate spend data can reveal real behavior—not just surveys or anecdotesAI adoption is rising: what Ramp’s data suggests about the share of businesses paying for AI tools and APIsThe “ROI” question: how we can infer whether AI is working (hint: contract sizes and renewals)Where spend is concentrating: tech and finance lead—but healthcare and manufacturing are climbing faster than many expectChatbots vs. real workflow change: why “everyone has a chatbot” isn’t the same as transformative productivityWho’s winning the model wars: OpenAI’s default position, Anthropic’s growth, and how buyers behave differentlyBundled AI and hidden usage: why Copilot/Gemini adoption is hard to measure, and why employees expensing personal accounts mattersTrust, governance, and observability: the fast-growing category of tools that monitor AI outputs and reduce reputational or security risk996 culture is real: what corporate receipts suggest about weekend work patterns in San FranciscoOpen source reality check: what the data suggests about DeepSeek-style hype vs. actual enterprise adoptionLooking ahead: why we likely won’t see a reversal in AI adoption—and why it’s still unclear who the ultimate winners will beTimestamps: 00:06:00 – What Ramp is, and what “Ramp Economics Lab” tracks00:08:00 – The biggest headline: adoption, spend, and contract sizes00:11:00 – Which industries are adopting fastest (including surprises)00:12:00 – Chatbots vs. productivity gains: where AI is actually moving the needle00:15:00 – Signals of ROI: contract renewals and retention trends00:16:00 – OpenAI vs. Anthropic: what spend reveals about “default” vs. multi-provider behavior00:18:00 – Why Copilot/Gemini are tricky to track (bundled AI)00:21:00 – The real blocker: trust in outputs (and how companies respond)00:26:00 – The rise of AI observability / governance tooling00:30:00 – What spend data can reveal about how work is changing (996 / SF)00:33:00 – How rare it is to see a trend that truly moves an economy00:36:00 – Is AI spend crowding out other budgets?00:38:00 – The narratives that bother Ara most: data-poor hot takes00:42:00 – Predictions: continued growth, unclear winners00:44:00 – DeepSeek and open source: what actually happened in the spend dataIf you want to understand AI adoption the way a CFO would—through budgets, renewals, and real purchasing behavior—this conversation will give you a sharper, more grounded lens. Guest: Ara Kharazian, Economist at Ramp; Lead, Ramp Economics Lab

    43 min
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4.9
out of 5
24 Ratings

About

A podcast that explores the good, the bad, and the creepy of artificial intelligence. Weekly longform conversations with key players in the space, ranging from CEOs to artists to philosophers. Exploring the role of AI in film, health care, business, law, therapy, politics, and everything from religion to war.  Featured by Inc. Magazine as one of "4 Ways to Get AI Savvy in 2024," as "Host Jeff Wilser [gives] you a more holistic understanding of AI--such as the moral implications of using it--and his conversations might even spark novel ideas for how you can best use AI in your business."

Information

  • Creator
    Jeff Wilser
  • Years Active
    2023 - 2026
  • Episodes
    123
  • Rating
    Explicit
  • Copyright
    © 2026 AI-Curious with Jeff Wilser
  • Show Website
    AI-Curious with Jeff Wilser

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