We were all told we needed AI. So, we got AI. And for a lot of companies… nothing really changed. Pilots worked. Tools got adopted. But when AI hit real workflows, things stalled or broke. The reality is, unless your business was built yesterday, it probably wasn’t designed for AI. This podcast is about that moment—when companies realize AI isn’t just something you add. It changes how the work actually gets done. We talk to the people figuring that out in real time—what worked, what didn’t, and what they did next.
Your AI Isn’t Broken, Your Process Is | with Alyssa Clarcq, “Alyssa with AI”
CPA-turned-AI-builder Alyssa Clarcq chats with Jess Lampe about her path from Big Four external auditing to vibe coding an "AI-native company" with no programing background.
15 Sept 2026
Babysitting vs. Delegating: How to Actually Trust an AI Agent
Everyone was promised that AI would hand back their time — so why does it still feel like you're babysitting four terminals and clicking "yes, allow this" one prompt at a time?
In this episode of Why Isn't This AI Thing Working, Jess Lampe talks with Jim and Alysha Rosser, co-founders of Entry Studios and the team behind Grove. Their take on why AI stalls after the pilot: it's a trust problem. Agents skip instructions, invent their own commands, and declare victory before the work is done.
Grove is their answer — wrapping AI in old-school determinism with task lists, proof requirements, permission "boundaries," and executive summaries that show the receipts on every session. The result: a two-person team that queues work overnight and reviews about ten PRs each morning (~900 merged since July). Along the way — cognitive load, "making determinism cool again," and why living in the chat window means you're doing it wrong.
Learn more at entrystudios.com.
1 Sept 2026
LLMs vs. Agents vs. Harnesses: How AI Actually Works
What's the difference between an LLM, an agent, and a harness? Launch Consulting's Alex Kozlowski joins Jess Lampe to pull back the curtain on how AI actually works under the hood — why hallucinations happen, what an "agent" really means, and why the "learn it the hard way" philosophy still matters. A practical, hype-free conversation about adopting AI tools, augmenting teams instead of replacing them, and building solutions that deliver real value.
18 Aug 2026
Edge AI Explained: Local LLMs, Token Costs and ROI w/ Ozzie Diaz
As AI shifts from flat subscriptions to metered, pay-per-token pricing, leaders need a clearer way to evaluate cost, performance and business value. Jess Lampe talks with Microsoft’s Ozzie Diaz about edge AI, local LLMs and the changing economics of enterprise AI. They explore when organizations should run AI models locally, what edge computing can offer and how leaders can think about privacy, latency, infrastructure and token consumption. Listen to understand the tradeoffs between cloud and local AI, how AI pricing affects financial planning and what CFOs and technology leaders should consider before scaling their next AI investment.
6 Aug 2026
Responsible AI: Building Customer Trust at Scale w/ Ieshika Chandra
Trust is what turns an AI experiment into a system people will continue to use. Jess Lampe talks with data science leader Ieshika Chandra about building responsible AI for real-world customer experiences. They explore how AI, machine learning and agentic systems can support personalization and product discovery, why reliable and fair models matter and how thoughtful guardrails help reduce errors. The conversation also examines customer trust as a measure of AI performance and what organizations need to operate intelligent systems at scale. Listen for a practical perspective on responsible AI, AI governance, customer trust and the balance between innovation and control.
21 Jul 2026
Generative AI Myths: What AI Can and Cannot Do w/ Luc Julia
Can machines truly create, understand or make decisions? Jess Lampe talks with AI pioneer and author Luc Julia about the biggest generative AI myths shaping today’s business conversations. Luc explains why AI should be understood as a powerful tool rather than an independent intelligence and why human creativity, expertise and critical thinking remain essential. The conversation examines generative AI limitations, workforce concerns, productivity and the difference between artificial intelligence and augmented intelligence. Listen to learn how business leaders can move past the hype, choose practical AI use cases and use AI to strengthen human capabilities rather than attempt to replace them.
14 Jul 2026
How to Build an AI Business Case That Proves ROI
Why do so many AI initiatives struggle to demonstrate measurable business value? Jess Lampe talks with Launch Consulting’s Nick Polachek about how to build an AI business case that resonates with CFOs and connects technology investment to real business outcomes. They explore why cost cutting alone is not a strong AI strategy, how token-based pricing changes financial planning and what leaders should consider when evaluating potential use cases. Nick also shares a practical six-step framework for selecting, launching and measuring AI investments. Listen for a clearer approach to AI ROI, enterprise AI strategy and scaling the initiatives that create lasting value.
22 Jun 2026
AI Adoption Starts With Curiosity, Not Technology
AI adoption often stalls because people feel intimidated, skeptical or unsure where to begin. Jess Lampe talks with Mike and Sammy Jacobson, creators of the AI-powered comedy show It Writes Itself, about using humor, creativity and experimentation to make AI more approachable. They share unforgettable audience reactions, unexpected live performances and lessons from helping people engage with AI in a low-pressure environment. Listen to discover why curiosity can be more valuable than technical expertise, how play can reduce resistance to AI and what organizations can learn about building confidence, participation and lasting AI adoption.
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