Couverture de Tentacles - the podcast from Crown & Reach

Tentacles - the podcast from Crown & Reach

Tentacles - the podcast from Crown & Reach

De : Tom Kerwin
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Hi, we’re Tom and Corissa from Crown & Reach, and this is Tentacles.


With over 100 episodes behind us, this might just be the best bad podcast out there. Unfiltered, unedited, and deeply curious.


We talk strategy, sense-making, and the blurry edges between work and the rest of life — because sometimes, the only way through the fog is to feel your way forward, limbs outstretched.


While we're migrating podcasts across, you can find all the goodness from our first 100 or so episodes here: https://shows.acast.com/triggerstrategy

Hosted on Acast. See acast.com/privacy for more information.

Tom Kerwin Direction Economie Management Management et direction
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    Épisodes
    • 128: Chalk, plasticine, and the art of experimenting when broke

      128: Chalk, plasticine, and the art of experimenting when broke
      Dec 22 2025
      You've been told you must transform your business with AI. But you have no budget for consultants, no runway for experiments, and absolutely no permission to fail.So... what now?This is the impossible bind facing many executives right now. And spoiler: trying to brute-force it is exactly how you end up as the expendable experiment in someone else's portfolio.Drawing lessons from electricity infrastructure booms, a hapless lettuce entrepreneur, Tom Chi's plasticine prototypes, and our own white-knuckle cash crisis earlier this year, we explore what actually works when resources are scarce, pressure is high, and the path forward is genuinely uncertain.Including-but-not-limited-to:Complexity of abundance vs complexity of scarcity: why portfolio strategies collapse when you run out of eggs to put in basketsThe electricity/steam substrate shift: why you can't just "add AI" to your existing factory layout and expect magicWhy some execs are being set up as expendable experiments in someone else's portfolio ... and how to spot if you're one of themOur own near-death cash flow moment, and why we didn't buy any of the blueprints that promised us a solutionWatchful waiting: the counterintuitive move that actually worked when all we wanted to do was panicWhy the lettuce man was right but early, which is functionally the same as being wrongTom Chi and the art of radical cheapness: testing Google Glass with plasticine, wire, and half a dayThe oblique AI productivity hack where you get productivity ... but not by trying to be productiveHow to make experiments so cheap that you can afford to throw most of them awayTesting your core assumptions vs your peripheral ones—why people protect their existential beliefsThe dangerous middle ground: trying to get early adopter benefits without an early adopter resource cushionWhy substrate change happens through billions of individual choices, not top-down mandatesJP Castlin's bind: when your assumptions don't match reality, you can try to change your assumptions or you can try to change reality. Choose wisely."If you're really at the point where you've got no resources left, you have to focus on survival first. You can't do transformation when you're in survival mode."References:East of Eden by John Steinbeck (the lettuce carriage story)Shape Up by Ryan Singer / Basecamp (fat marker sketches)Dave Snowden - Cynefin framework https://cynefin.io/wiki/CynefinImre Lakatos - philosopher (research programs: core vs peripheral assumptions)JP Castlin https://strategyinpraxis.substack.comTom Chi - Google Glass rapid prototyping https://youtu.be/d5_h1VuwD6gRob Snyder - PULL framework, AI note-taker example https://howtogrow.substack.com/p/nobody-wants-aiJohn Cutler & Tom's article about leading in ambiguity https://cutlefish.substack.com/p/tbm-274-how-capable-leaders-navigateUncertainty bubbles / The Double Game (deliberate vs emergent strategy) Opportunity Method Format (OMF) https://shows.acast.com/triggerstrategy/episodes/052-omf-opportunity-method-formatMultiverse Mapping https://multiversemapping.com4U framework: Unpack, Undergo, Unfold - https://crownandreach.com/#resourcesObliquity by John KayThe Founder (McDonald's kitchen scene) https://youtu.be/F-7cjdtrQ9YMinority Report (gesture interface scenes)Episode on Founder Mode / Brat Summer https://shows.acast.com/triggerstrategy/episodes/073-brat-summer-for-billionairesEpisodes 007-009: Pitch Provocations: https://shows.acast.com/triggerstrategy/episodes/663109cbcff31b0012ae9326Find out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.
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      43 min
    • 127: The unbundling and bundling of jobs

      127: The unbundling and bundling of jobs
      Nov 21 2025

      Is your very job dissolving? You're not imagining it.


      As festive redundancy season rolls around (you've noticed the seasonal pattern too, right?), we explore how the boundaries around professional roles have been blurring and melting, and what that means for anyone who feels like their job identity is slipping away.


      Using the corollary of music – from vinyl singles through to algorithmic playlists — we map that to knowledge work. How do patterns of democratisation, "AI", and evolving business models play into what a job even is?


      And we look at how these cycles always create new opportunities from the mess. The big question is how to reposition yourself if the ground keeps shifting.


      Including-but-not-limited-to:


      ● The bundling and unbundling pattern: from singles to albums to MP3s to playlists, and how it applies to your career right now

      ● "Mandatory entrepreneurship" and the pressure to become self-employed even when you'd rather just do good work (hat tip Lex Roman)

      ● How roles like designer, engineer, and product manager are blurring beyond recognition

      ● Why jack-of-all-trades is hot again (and what that means for specialists)

      ● Democratisation that scales quality vs. democratisation that cuts costs

      ● How to joyfully remix your own job: what do you actually like doing and what would you happily leave behind?

      ● Henrik Karlsson's musician story: what your role "ought" to mean vs. what you actually want to do

      ● Practical strategies for increasing your luck surface area (without becoming a hustle bro)

      ● The grieving process that comes with career rebirth


      For anyone who's wondering why their carefully-built expertise suddenly feels less solid than it used to, and what the heck is next.


      References:


      • John Harvey Jones - The Troubleshooter - at Morgan Cars https://www.youtube.com/watch?v=PtDA714SdgQ
      • Henrik Karlsson's musician friend https://www.henrikkarlsson.xyz/p/constraints
      • Episode 043: Do 100 Thing https://shows.acast.com/triggerstrategy/episodes/043-do-100-thing
      • Visakan Veerasamy's Do 100 Thing https://www.visakanv.com/blog/do100things/
      • Mandatory entrepreneurship concept from Lex Roman https://www.linkedin.com/posts/lexroman_were-you-forced-to-become-an-entrepreneur-activity-7371539212074004480-8Z7R
      • "There's only two ways to make money in business: One is to bundle; the other is unbundle." - Jim Barksdale, former Netscape CEO
      • Corissa's Ultrabangers playlist https://open.spotify.com/playlist/3FFiwdRsFjMXYvye4lbzE4?si=9242add1c657441c



      Find out more about us and our work at crownandreach.com

      Hosted on Acast. See acast.com/privacy for more information.
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      25 min
    • 126: Critique-al Thinking

      126: Critique-al Thinking
      Nov 7 2025

      Tom got AI to critique his sales call. The feedback was detailed, line-by-line, technically correct... and basically useless.


      In this episode, we dig into the surprising limitations of LLMs that most people don't seem to be talking about. Not the obvious media fluff about hallucinations or training data or taking everyone's jobs, but the deeper constraint: they can't reorient.


      We start with our experiment using an LLM to critique one of our client discovery calls, which led to an observation about what's missing. We talk about what happens when AI conducts research interviews, why care home robots are increasing the workload they're supposed to decrease, and the crucial difference between "reading all the books" and actually understanding what matters.


      This isn't anti-AI. It's about being clear about what these tools can and can't do, and why that matters for anyone doing customer research, strategy work, or trying to understand real human problems.


      Including-but-not-limited-to:


      • Why the AI critique of Tom's sales call was technically brilliant but fundamentally unhelpful
      • Boyd's OODA loop and the missing "orientation" capability in LLMs
      • What happened when someone showed up to a research call... with an AI interviewer
      • The emotion gap: why LLMs can't follow the rich seams of energy in a conversation
      • Why LLMs don't know when to pivot and when to push
      • Japanese care home robots that create more work than they save, and the babysitting idiots effect
      • Venkatesh Rao's "it's read all the books" theory of LLM usefulness (and when it actually works)
      • How our "expert panel" AI prompt is useful for critique—if you keep your critical thinking switched on
      • Why pattern-matching to words isn't the same as understanding context
      • You heard it here second? Active inference models: the next wave beyond LLMs?


      If you'd like a copy of our experimental "expert panel of dissenters" prompt, email us at tentacles@crownandreach.com and remember the risk: it requires your critical thinking.


      References


      • Ben Ford ("Commando Dev") on No Way Out Podcast https://podcasts.apple.com/gb/podcast/agentic-ai-thinks-like-boyd-the-ooda-upgrade-llms-cant-touch/id1663685759?i=1000734032438
      • Venkatesh Rao https://substack.com/@contraptions
      • John Boyd's OODA Loop and Snowmobiling
      • JP Castlin's Strategy in Praxis https://strategyinpraxis.substack.com/p/the-only-one-writing-and-ai
      • Dave Snowden's Ritual Dissent - https://cynefin.io/wiki/Ritual_dissent

      Find out more about us and our work at crownandreach.com

      Hosted on Acast. See acast.com/privacy for more information.
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      20 min
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