AI-Curious with Jeff Wilser

It’s happening everywhere. And no one’s really talking about it. What happens when your employees are already using dozens of AI tools your company never approved?
In this episode of AI-Curious, we talk with Rick Caccia, co-founder and CEO of Witness AI, about the rise of “shadow AI” inside enterprises and why it has become one of the biggest practical challenges in AI adoption. We explore how employees, often with good intentions, are quietly using ChatGPT, Copilot, and thousands of other AI apps to do their jobs faster, sometimes with sensitive data that should never leave the company.
We also dig into what happens when that behavior scales. From customer support teams pasting financial information into AI tools, to marketers uploading customer lists, to developers sharing source code with external models, we look at the real security, compliance, privacy, and cost risks companies are now facing. We also discuss why this problem gets even harder with AI agents, which can take actions, access systems, and create new forms of risk far beyond a simple chatbot prompt.
Along the way, we talk about prompt injection, jailbreaks, token costs, insider risk, enterprise governance, and how leaders can build an AI strategy that enables productivity without creating chaos. This is a practical conversation for anyone trying to understand how AI is actually being used inside organizations right now, and what it takes to manage that responsibly.
Guest
Rick Caccia — Co-founder and CEO, Witness AI
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For anyone interested in Jeff’s AI Workshops for their company:
Reach out directly at [email protected]

What happens when an AI prediction does not just forecast the future, but helps create it?
In this episode of AI-Curious, we talk with philosopher and ethicist Carissa Véliz about AI ethics, AI privacy, predictive AI, and the hidden power of algorithmic decision-making. We explore how AI systems used in hiring, lending, insurance, and other high-stakes settings can become self-fulfilling prophecies, shaping outcomes rather than simply measuring them.
We also examine the growing privacy risks of large language models and AI agents, especially as they gain access to more personal data, communications, and systems. Along the way, we discuss automated decision-making, surveillance, human autonomy, and why predictions about people are far more ethically fraught than predictions about things like the weather.
This conversation also goes beyond policy and into philosophy: how narratives about AI shape public thinking, why humor can be a response to technological power, and how individuals and companies can use AI responsibly without giving up judgment, control, or resilience.
If you are interested in AI ethics, algorithmic bias, AI privacy, AI agents, responsible AI, predictive algorithms, self-fulfilling prophecy, and the future of AI, this episode offers a clear and thought-provoking framework for understanding what is at stake.
Guest
Carissa Véliz — Philosopher, Associate Professor at the Institute for Ethics in AI at the University of Oxford, and author of Prophecy, Prediction, Power, and the Fight for the Future: From Ancient Oracles to AI.
Carissa's TED talk:
https://www.ted.com/talks/carissa_veliz_beware_the_power_of_prediction
Carissa's new book: Prophecy, Prediction, Power, and the Fight for the Future: From Ancient Oracles to AI.
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For anyone interested in Jeff’s AI Workshops for their company:
Reach out directly at [email protected]

What if the job you have today will soon require a completely different set of skills? 
In this episode of AI-Curious, we talk with Dan Roth, Editor in Chief of LinkedIn, about what LinkedIn’s data reveals about the future of work, the rise of AI literacy, and why deeply human skills may matter more than ever. We dig into LinkedIn’s “Skills on the Rise” research, what employers are actually looking for now, and why the shift toward skills-based hiring is changing how people get hired, promoted, and evaluated.
We also explore the surprising rise of storytelling, public speaking, conflict resolution, and stakeholder communication in an AI-driven workplace. Along the way, we discuss why traditional resumes and polished cover letters may matter less in a world where anyone can use AI to sound impressive, and why some companies are moving toward live prototyping and real-time problem solving in interviews instead.
Later, we get into AI agents, what Dan is building himself, and how leaders can create stronger AI adoption inside their companies. We also talk about what it takes to stay competitive in a job market where AI is changing the stack of work, but not necessarily replacing the worker.
Guest
Dan Roth — Editor in Chief, LinkedIn
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For anyone interested in Jeff’s AI Workshops for their company:
Reach out directly at [email protected]

What does it actually look like to use AI tools in the real world, beyond the usual chatbot prompts and hype?
In this episode of AI-Curious, Jeff Wilser shares five AI tools and workflows that are shaping how he works right now, from Claude Code and personalized news briefings to NotebookLM, multi-model prompting, and using AI to write more closely in your own voice. The goal is not to offer a comprehensive list of every AI product on the market, but to show how these tools can be used in practical ways that expand capability, streamline research, and create new workflows.
We explore how vibe coding and AI agents can help non-coders build useful internal tools, why personalized AI news feeds may become increasingly common, and how NotebookLM can synthesize large amounts of information across transcripts, documents, and YouTube videos. We also look at the benefits of using multiple AI models together instead of relying on just one, and why feeding AI much richer context can dramatically improve writing outputs.
Throughout the episode, we return to a core idea: using AI to empower, not eliminate. Rather than treating AI only as a cost-cutting tool, we examine how it can help individuals and businesses do more, think more creatively, and build smarter systems around the work that matters most.

Key topics we cover
3:15 — Claude Code, vibe coding, and why non-coders should be paying attention
6:01 — Building a custom AI-powered conference outreach and research tool
11:05 — “AI to empower, not eliminate” as a guiding philosophy
16:16 — Personalized AI news briefings and the future of customized information
21:58 — How NotebookLM helps synthesize transcripts, documents, and YouTube content
27:04 — Why a “polymodel” approach can be better than relying on one chatbot
31:15 — Using AI to write more closely in your own voice through deeper context
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For anyone interested in Jeff’s AI Workshops for their company:
Reach out directly at [email protected]

What happens when AI stops being a productivity tool and starts reshaping the structure of work itself?
In this episode of AI-Curious, we talk with Kelly Monahan, a future of work and AI advisor, about what AI may actually do to the workplace over the next few years, and why the reality is likely to be messier than both the hype and the fear suggest. We dig into the tension between using AI for augmentation versus automation, why so many companies are still struggling to prove ROI, and how AI agents could transform business workflows while also creating major governance, accountability, and implementation challenges.
We also explore what this means for knowledge workers, middle managers, and enterprise leaders trying to adapt in real time. Along the way, we discuss why small businesses may have an advantage over large organizations, how workers can focus on higher-value contributions, and why the future of work may require not just new tools, but a new mindset.

Guest
Kelly Monahan — Future of Work and AI Advisor

Key topics we cover
2:49 — Kelly’s optimistic and pessimistic theses on the future of work
5:15 — Where AI is overhyped, and the disconnect between leaders and workers
6:35 — Why generative AI adds complexity inside organizations
10:05 — What the research says about AI ROI
12:54 — Where AI is delivering real wins today, especially for freelancers and small businesses
16:27 — Advice for leaders and middle managers inside large organizations
18:39 — Why curiosity, learning, and experimentation need to be rewarded
19:02 — AI agents, the hype cycle, and why the excitement may still be justified
22:25 — Why enterprises are struggling to keep pace with the speed of AI change
29:18 — What the future of work may look like over the next 3 to 5 years
30:02 — Why white-collar work could face major disruption
33:37 — The “elevator to skyscraper” analogy for how AI should reshape work
35:08 — Predictions for AI adoption, governance failures, and labor market shifts
39:00 — How Kelly uses AI in her own work and business

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For anyone interested in Jeff’s AI Workshops for their company:
Reach out directly at [email protected]