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Ryan Holiday argues that while AI can generate outputs, it cannot generate wisdom. Drawing on a story from Seneca about a Roman who used educated slaves to sound intelligent, he compares outsourcing thinking to outsourcing exercise: the value comes from becoming the kind of person who can do the work, not simply producing the answer.
The conversation explores the difference between useful cognitive offloading and surrendering judgment entirely. Ryan explains that while tools like GPS may replace navigation skills without much consequence, writing, decision-making, and critical thinking shape the person on the other side of the process. AI, he argues, tends to amplify existing tendencies. People satisfied with mediocre work will settle faster, while people pushing for exceptional work can use AI to refine and challenge their thinking.
Throughout the episode, Stoicism serves as a counterweight to both panic and hype. Change and uncertainty are constants throughout history, not exceptions. Ryan reflects on leadership, family, adaptability, and skepticism, arguing that in a world where AI can confidently produce both insight and nonsense, the ability to question, verify, and think independently becomes increasingly valuable.
Key Takeaways:
Ryan's website: ryanholiday.net
00:00 Intro: You Can’t Outsource Wisdom
00:29 Meet Ryan Holiday
02:03 The Dream Was To Work Less
03:07 Who Actually Gets The Time?
06:32 Leadership, Culture, And Family First
08:38 How Will You Measure Your Life?
10:11 The Stoic View Of Change
14:44 AI Hallucinations And Shameless Confidence
17:21 You Cannot Outsource Wisdom
19:08 Cognitive Offloading Vs Real Understanding
20:22 Ego, Flattery, And AI
22:52 AI As Editor And Thought Partner
24:59 Mediocre Vs Exceptional Work
31:15 Why Bullshit Detection Matters
38:06 Stoicism, Agency, And Adapting To Change
43:31 The Debrief
📜 Read the transcript for this episode: you-cant-outsource-wisdom-bestselling-author-ryan-holiday-on-what-the-stoics-have-to-say-about-ai/transcript
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
Laura Jones explains that generative AI is raising the bar for creativity. When everyone can produce “pretty good” content, the real challenge is creating something that actually stands out. The risk is not poor output, but settling too quickly for what already works.
She argues that as products become more similar, brand becomes a signal of trust. Not in a visual sense, but in the experience behind it. At Instacart, that shows up in details like how a banana is selected. With over a billion bananas delivered and millions of orders including notes on ripeness, customers are expressing very specific preferences. That behavior led to both new product features and the creative idea behind their Super Bowl campaign.
The conversation also explores how teams should work with AI. While it can automate repetitive tasks and speed up iteration, it can also create a tendency to agree with what’s generated, especially when working alone. Laura emphasizes that the best ideas still come from people challenging each other, building on different perspectives, and pushing beyond the first acceptable answer.
Key takeaways:
Instacart: instacart.com
00:00 Intro: Originality vs AI Complacency
00:27 Meet Laura Jones
01:23 Brand as trust when products converge
03:50 Personalization and reducing mental load
06:24 What still matters in marketing
10:33 Why need-finding cannot be shortcut
14:09 Using AI without losing judgment
16:33 New channels and where customers actually are
21:35 Why “dopey ideas” matter
25:42 Human plus bot plus human
28:44 Inside the Super Bowl ad
31:47 From banana insight to product
34:49 Taking creative risks at scale
37:34 Fear, pressure, and team chemistry
46:24 AI and faster prototyping
53:26 The debrief
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
Dan Klein, professor at UC Berkeley and CTO at Scaled Cognition, explains that AI systems generate answers based on patterns in language rather than verified knowledge. This makes them highly capable across many tasks, but also means they can produce confident answers even when they are not fully accurate.
He introduces the “jagged frontier,” where AI performs very well in some areas and less reliably in others. Because responses are fluent and convincing, it is often hard to see where those limits are, which makes it important to stay engaged when using these systems.
The conversation also explores hallucinations as a natural part of generative systems. In some cases, this is what makes them valuable, especially for creative or open-ended tasks, while in other cases reliability becomes more important.
Finally, Dan highlights that working effectively with AI is a skill. As more people start using these systems in their daily work, knowing how to guide them, evaluate outputs, and apply them in the right contexts becomes increasingly important. He also shares how his team at Scaled Cognition is tackling this challenge by building AI systems with fundamentally different architectures, focused on determinism and reliability — aiming to ensure systems follow rules, reflect underlying data accurately, and behave predictably in high-stakes, policy-driven use cases.
Key Takeaways:
Dan's LinkedIn: linkedin/dan-klein/
00:00 Intro: Fluency vs Truth
00:34 Meet Dan Klein
02:53 Why Fluency Misleads
05:11 How LLMs Guess
07:30 What Is Hallucination
08:54 Deception and Alignment
11:22 Why Agents Break
12:48 Chaining and Determinism
16:01 When Hallucination Helps
22:33 Beyond Scale for Reliability
30:40 Synthetic Data Training
31:10 Enterprise Agent Use Cases
33:44 Healthcare Risks
39:13 Enterprise Literacy Gap
41:27 Delegation and AI Management
54:37 The Debrief
📜 Read the transcript for this episode: nobody-is-getting-new-manager-training-for-their-ai-team-with-dan-klein-uc-berkeley/transcript
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
Melissa Cheals leads Smartly, a payroll and people management platform serving 24,000 small and medium businesses in New Zealand. In this conversation, she shares how AI is reshaping product development, leadership, and how organizations operate.
A key moment comes when her team estimates new features will take 12 months and $1M to build. Instead of accepting it, Melissa pushes back, using AI to better understand her team’s perspective and communicate the need for change more effectively. This becomes a broader shift in how she approaches leadership, using AI to think more clearly and navigate conversations with less friction.
Key Takeaways:
Smartly: smartly.co.nz
00:00 Intro: Challenging AI Assumptions
00:28 Meet Melissa Cheals
01:17 The Spark For Change
02:36 Vision And Early Signals
03:48 Hiring For Transformation
06:12 Unlocking Data With AI
08:27 Breaking Silos Across Teams
10:39 Why Leaders Must Learn AI
13:42 Leading With AI And Clarity
17:05 The AI-Native Decision
21:45 Thinking Bigger With AI
25:23 Less Meetings More Writing
26:33 The Self-Disruption Imperative
29:11 Breaking Silos With Value Streams
31:28 Managing Fear And Change
32:50 Learning And Shipping Faster
34:58 Debrief
📜 Read the transcript for this episode: ai-native-or-not-the-defining-choice-for-companies-right-now-with-melissa-cheals-ceo-of-smartly/transcript
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
Greg Shove describes a growing gap between individual and organizational AI adoption. A small group of employees are already using AI effectively, while most companies are still early. AI is generating real productivity gains, but those gains are not being captured at the company level. Instead, they are absorbed by individuals who use AI to work faster, often without changing team outputs or structures — raising a central question: if AI creates time, where does that time go?
The conversation explores why enterprise AI adoption remains uneven. Many organizations lack a clear point of view on AI, and workflows take time to adapt, making it difficult to turn individual gains into coordinated results. At the same time, AI is breaking capability boundaries, allowing people to take on work across roles while companies remain structured around existing ways of operating.
From a leadership perspective, Greg emphasizes that the challenge is not just efficiency. AI creates capacity, but without clear direction on how to use it, that capacity disappears. Leaders must decide how to reinvest the time AI creates if they want to capture real business value.
Key Takeaways:
Greg's LinkedIn: linkedin/gregshove
00:00 Intro: Entering the Era of AI Chaos
00:31 Meet Greg Shove
01:32 Enterprise AI Is a C Minus
01:51 AI’s ROI Is “Leaking” to Employees
03:04 When Individuals Outrun the Organization
05:44 When AI Breaks Workflows
06:47 Disposable Software and New Ways of Building
09:10 Cut vs Create
12:01 Using the Calendar as a Lever
16:24 Why Enterprises Don’t Move
17:32 When Customers Force Change
21:31 AI Breaks Capability Boundaries
25:44 The Productivity Firehose
27:49 Who Actually Captures the Value
28:45 Why Everyone Needs Good AI
32:00 Adoption Beats Buying More Tools
40:17 Teaching the 90 Percent
43:48 Where Humans Still Matter
48:09 The Debrief
📜 Read the transcript for this episode: greg-shove-on-why-most-companies-are-not-seeing-roi-on-ai-yet/transcript
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
Leidy Klotz has spent years studying a simple but overlooked phenomenon: when we try to improve something, our first instinct is to add rather than remove. He shares the Lego bridge experiment that sparked his research and explains how this additive bias scales from small design decisions to entire organizations. Over time, companies accumulate reporting lines, meetings, software, and policies without questioning what no longer serves them.
Henrik and Jeremy explore how AI tools intensify this pattern. When generating ideas, launching projects, writing code, or producing content becomes effortless, the temptation to add grows stronger. The cost of producing information drops, but the cost of consuming it rises. Without guardrails, organizations risk what Leidy calls “organizational indigestion.”
The discussion moves from insight to implementation. Leidy outlines practical ways to counteract additive bias, including stop-doing lists, default kill dates on projects, and designing environments that make subtraction visible and acceptable. In a world of accelerating AI output, leaders must intentionally decide what to remove, what to protect, and what truly matters.
Key Takeaways:
Subtract: amazon/Subtract-Untapped-Science-Leidy-Klotz
00:00 Intro: Our Instinct to Add
00:28 Meet Leidy Klotz
01:15 The Subtract Idea
02:56 Organizations Get Bloated
03:49 Scandinavian Design Mindset
04:32 New Book: In a Good Place
05:59 AI Abundance and Indigestion
08:12 Curate Context, Not More
11:38 Cues and Stop-Doing Lists
15:00 Default Debt and Kill Dates
17:10 Odysseus Contracts and Biases
21:28 Reengage the Physical World
29:17 Bike Shedding and Priorities
36:10 Making Is Thinking
49:16 The Debrief
📜 Read the transcript for this episode: how-to-subtract-the-most-underrated-skill-of-the-ai-era-with-leidy-klotz/transcript
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
Fathom was built on the assumption that transcription would become commoditized and generative models would steadily improve. Rather than training proprietary models, Richard focused on building the infrastructure around them and waiting for model capabilities to reach the right threshold.
In this conversation, he explains why AI has made effort and impact harder to predict, and why that shifts product development from roadmap execution toward experimentation. He describes separating an exploratory AI team from core engineering, structuring that team to prototype and write specs, and expecting a meaningful portion of experiments not to work.
Richard introduces his Jenga model for AI development, testing different models and use cases to find where resistance is lowest. He also discusses the operational realities of rapid model updates, hallucination rates, and what he calls the LLM treadmill.
The discussion explores qualitative QA, organizational design, buy versus build decisions, and why leadership taste plays an increasingly important role as AI lowers the barrier to generating outputs.
Key takeaways:
Fathom: fathom.ai
Fathom LinkedIn: linkedin/company/fathom-video/
Richard's LinkedIn: linkedin/in/rrwhite/
00:00 Intro: Why AI Breaks Roadmaps
00:19 Meet Richard White (Fathom AI)
02:16 From Roadmaps to R&D
04:49 Designing AI Teams for Speed
07:11 The Jenga Model
09:56 Failing 50% & AI Team Psychology
13:40 LLMs as Interns & Anti-Planning
21:01 QA, Data Pain & Developing Taste
24:59 Executive Taste & Culture Rules
27:20 Reacting to AI Waves
28:50 Fathom’s 4-Step Product Plan
30:47 What New Models Unlock
32:13 From Scribe to Second Brain
40:32 Build vs Buy in AI
45:32 The Debrief
📜 Read the transcript for this episode: from-roadmaps-to-rd-how-ai-is-changing-product-development-with-richard-white-founder-of-fathom-ai/transcript
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
In this episode, Bryan McCann joins Henrik and Jeremy to explore how search is evolving from simple queries into more conversational and agent-driven systems, and why prompting is likely a temporary skill. Bryan shares how his definition of productivity changed as an AI researcher, moving away from doing the work himself and toward designing plans and experiments that machines could run continuously.
The conversation expands to leadership and organizational design. Bryan explains why helping others learn how to work with AI became his highest-leverage activity, and offers a simple rule of thumb: try to get AI to do the task first, and treat anything it can’t do as an interesting research problem. Henrik and Jeremy connect this to Bryan’s view that organizations may increasingly resemble neural networks, with information flowing more freely and decisions less tied to rigid hierarchies.
Key Takeaways:
YOU: You.com
Bryan's website: bryanmccann.org
LinkedIn: linkedin/company/youdotcom/
00:00 Intro: Keeping the GPUs Full
00:22 Meet Bryan McCann: CTO & co-founder of You.com
00:43 Why Search Is Breaking - and Why It Becomes a Skill
01:41 From Search to Agents
03:18 The Case for Proactive, Context-Aware AI
04:30 We Don’t Need New Hardware - We Need Trust
05:43 The Trust Problem of Always-On Listening
07:57 Trust as the Real Bottleneck (Not AI Capability)
09:52 Delivering Immediate Value to Earn Trust
12:13 Business Models and Escaping the Attention Economy
17:27 What “Agents” Really Mean - and Why the Term Will Fade
20:37 Productivity, Parkinson’s Law, and Keeping the Machines Running
23:52 Scaling Yourself vs. Scaling Your Team
29:57 Building Culture: Automate, Throw Away, Rebuild
35:46 Designing Organizations Like Neural Networks
45:02 Recruiting for Initiative in an AI-Native Organization
49:18 The debrief
📜 Read the transcript for this episode: podcast.beyondtheprompt.ai/heres-how-to-know-if-youre-getting-the-most-out-of-ai-with-bryan-mccann-cto-of-youcom/transcript
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
In this episode, Humza Teherany breaks down how he bridges deep technical fluency with strategic leadership at MLSE, home to the Raptors, Maple Leafs, and more. He shares how a vacation turned into an AI reawakening and how that hands-on immersion led to a fundamental shift in how his organization builds and experiments.
Humza walks through MLSE’s build in a day practice, their internal AI platform, and why speed to prototype now unlocks more than just efficiency. It changes who gets to shape the future. He, Jeremy, and Henrik explore the limits of traditional enterprise AI rollouts and how to build spaces for superusers that enable company-wide transformation. The conversation covers how technical literacy impacts credibility, why idea execution is the new differentiator, and how Humza’s five-year-old inspired a bedtime story app powered by AI.
Whether you're a CTO, a founder, or just figuring out where to start, Humza makes a compelling case. The best leaders don’t delegate this moment. They build.
Key Takeaways
MLSE: mlse.com
LinkedIn: Humza Teherany - LinkedIn
00:00 Intro: Humza Teherany and MLSE
00:27 The Role of C-Suite Leaders in AI
01:08 Reconnecting with Technical Skills
02:08 Diving Deep into AI Tools
03:03 The Importance of Hands-On Learning
04:25 Progression from Consumer to Technical AI Tools
07:28 Building a Business Case for AI
10:03 Creating a Culture of Innovation
14:00 Implementing AI in Business Operations
21:05 Challenges and Strategies in AI Adoption
26:17 Organizational Structure for AI Success
32:02 The Importance of Reviewing and Planning Code
33:01 The Future of Solo Developers and New Technologists
34:58 Reimagining Company Structures with AI
38:55 Key Skills for Future Technology Leaders
41:19 Personal AI Experiments and Innovations
46:52 Encouraging Creativity in Children with AI
49:11 The Debrief
📜 Read the transcript for this episode: building-an-enterprise-ai-innovation-lab-a-master-class-with-humza-teherany-chief-strategy-officer-of-maple-leaf-sports-and-entertainment/transcript
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
In this teaser, Henrik and Jeremy debrief their conversation with Humza Teherany, Chief Strategy and Innovation Officer at MLSE. They reflect on how Humza rebuilt his technical fluency, why he believes leaders can't delegate this moment, and what it actually looks like to launch an internal AI lab that ships in 24 hours. Full episode out next week.
Full episode LIVE NOW.
For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:
Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley
Show edited by Emma Cecilie Jensen.
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