Tom Kerwin
Tentacles - the podcast from Crown & Reach
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.
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Episodes
146: Weak signals in AI – or it grew really tall and fell over 08.07.2026 40:08
More apps are shipping to the app stores, but the same number of apps are getting downloaded. In this one we're pushing a pram round Bournemouth with a one-month-old and making sense of the current AI moment — from the slop machine that online advertising has become to why the big frontier model bet may have misfired, and what a walking creature that just falls over can teach us about software dev...
145: What Xerox PARC actually got wrong 28.05.2026 38:53
Xerox PARC famously invented the mouse, the graphical user interface, and the printer — then watched Steve Jobs walk off with all of it. The usual lesson: silly management didn't recognise what they had. The actual lesson is more useful ... and more uncomfortable for innovator types. Sit in your beanbag so you can't storm off. In this one, we use Xerox PARC as a case study in what happens when an...
144: The domino rally delusion 24.05.2026 30:17
What do you do if Strategy Doesn't Exist? Tom and Corissa have built a strategy consultancy and they're here to tell you that strategy doesn't exist. At least, not in the way everyone sells it — and probably not in the way you've been trying to do it. This one was sparked by a recent episode from friends-of-Tentacles Kyle and Jen on Notes from the Swamp . We start with domino rallies and end up so...
143: The breadmaker trick 13.05.2026 39:43
Bread makers don't knead dough the way a human baker does. They get to the same result via a completely different route — and that turns out to be a pretty good map for what's actually happening with AI right now. We start with brioche, end up in a crisis of professional tacit knowledge, and find a surprisingly useful frame for thinking about what machines can and can't do — and what that costs us...
142: Sit with it 29.04.2026 24:38
When a hiring manager asks an unanswerable question, what if that's the whole point? In this one, Corissa brings along a Reddit thread that stopped her in her tracks. A candidate who discovered, mid-interview, that the interviewer had never once rejected someone based on their actual answer. What they were watching for was whether you'd sit with the discomfort of having no right option, or immedia...
141: Indifference is the default 20.04.2026 40:52
Everyone's got a brilliant value proposition. And most of them fail. Tom's been reading a book that argues the problem isn't your messaging, your features, or your market research. The problem is that most people — most of the time — simply don't care . Indifference is the default. And you can't overcome indifference by being more persuasive. (Nor by shipping faster, dear LLM code wrangling friend...
140: A pandemonium of stochastic parrots 23.03.2026 27:00
Your hospital has a brilliant new security measure. Your doctors have a paper cup. Your IT team demands a new password every fortnight. Your staff have a Post-it note. Every time someone tries to make a system more secure, the system gets less secure. Tom and Corissa roam from hospital proximity sensors to vibe-coded spreadsheets, and find the same story playing out everywhere: different incentive...
139: Sturgeon's Vibe Code 18.03.2026 27:56
Everyone’s got an opinion on vibe coding. Half the internet says it will save you £150,000 a year and you will never need a developer again. The other half says it is a dumpster fire of security holes and spaghetti code. Both camps are loud. Both camps are partially right. And lots of us watching the bunfight are just confused. In this one, Tom and Corissa try to make sense of it — not by picking...
138: Kill, pivot, commit? … the swing dance switcheroo 05.03.2026 37:39
You're doing everything right. The team is working hard, the process looks sensible, the effort is real. And yet — somehow — it's still not working. And nobody quite wants to say why. In this one, we use our own dance teaching as a live case study in kill, pivot, commit decisions: two years of tweaks, probes, and exhausted options before one unexpected forcing function finally made the decision fo...
137: The six or seven problem when "being more strategic" 20.02.2026 28:21
Being strategic sounds like it should be serious business. It turns out the seriousness can be exactly what gets in the way. Following on from episode 136, Tom and Corissa pick up a listener thread about strategy being a zero-sum status game at the company level — then take a sharp left turn into why most people are stuck in exactly the wrong zone for doing anything useful with uncertainty. The co...
136: When they tell you to "be more strategic" (but not what that actually means) 12.02.2026 32:35
When your boss tells you to "be more strategic," what do they actually mean? Sometimes it's genuine - they see you working hard on the wrong things and want to help you refocus. Sometimes it's politics - they need you to read between the lines they can't legally spell out. And sometimes it's just offloading risk. The problem? You're supposed to figure out which story is true, and then what to do a...
135: The resistance to instability - and why Stewart Lee hasn't finished his show yet 06.02.2026 22:47
What does a comedian's unfinished show, a five-year plan gathering dust, and your CEO's quiet plea to "go back to normal" have in common? They're all wrestling with the sense that eventually, things will settle down, right? That the chaos is only temporary. That once this transformation/restructure/market shift is done, we can finally get back to business as usual. In this one, with plenty of trad...
134: The Protocol Problem part 1 – Geoff's shadow spreadsheet sprawl 20.01.2026 29:59
"Geoff" has been running critical parts of every business on a Byzantine spreadsheet empire for 20 years. Every IT department wants to regulate him. Who's right? (Trick question: you need both.) In this episode, we feel our way through the murky territory of protocols—from life-saving surgical checklists to shadow IT empires built by people like Geoff, who just want to get their jobs done without...
133: Giant hats and fluffy aspirations - a year in review 16.01.2026 38:01
At the start of 2025, we faced a question: should we pack in our business and get [gasp] proper jobs ? Our old brand felt like rotten decking – layers of horrible surprises with no clear foundation. But instead of quitting, we found an octopus, embraced distinctiveness over differentiation, and built something we're actually excited about. In this year-in-review, we trace a tangled thread from nea...
132: Skate where the poke is going 15.01.2026 46:19
What if the reason you can't find the right name for your experiments is because you're asking the wrong question? In this one, we tackle a deceptively simple question from friend-of-Tentacles Matti about behavioural scientists, voting SMS messages, and which Cynefin domain they're playing in. This spirals into a wonderfully messy exploration of why simulation has limits, why "safe to fail" needs...
131: Safe-to-fail boops – a pragmatic critique of pseudo-scientific business experiments 13.01.2026 27:09
Jeff Bezos famously said not to overthink decisions you can just undo. But what if rolling back a change doesn't actually roll anything back? Tom and Corissa explore what can happen when you stack "reversible" experiments until the whole system collapses—from Facebook's slow degradation to an apocryphal Tesco story where undoing an experiment didn't fix what got broken. Along the way: sand pile cr...
130: The Sinclair Effect and the Winkler Constraint 09.01.2026 29:20
Upton Sinclair said "It is difficult to get a man to understand something when his salary depends on his not understanding it." But what if it goes deeper than salary? What if it's about identity itself? In this one, we explore why clear explanations often increase resistance, how an interior designer accidentally solved the change management problem, and what executive data analysis reveals when...
129: Who gets to decide what counts as an insight? 07.01.2026 31:56
Can "insights" be pre-packaged? Should they be? In this one, we wade into the murky distinction between polished agency deliverables and raw, messy data exposure. From a bank that knew what it wanted (and just needed to show due diligence) to clients who fundamentally changed direction after reading customer transcripts, we explore when different approaches can actually work. Along the way we talk...
128: Chalk, plasticine, and the art of experimenting when broke 22.12.2025 43:24
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 inf...
127: The unbundling and bundling of jobs 21.11.2025 24:52
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 play...
126: Critique-al Thinking 07.11.2025 19:31
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 e...
125: Peak uncertainty and the pickle jar 21.10.2025 22:58
Q. When do teams want certainty the most? A. Exactly when it's least available! Not a joke. Just true. This time we look at the patterns of peak uncertainty: those make-or-break moments when an organisation desperately wants a clear plan but is operating in conditions where rigid plans are most likely to fail. We bang on about our Go to Market Sprint offering and the uncertainty-native methods beh...
124: Norman doors, knuckle-scrapers, and the Cost-Pain Seesaw 14.10.2025 22:43
What do post office doors that won't open and door handles that scrape your knuckles have to do with product strategy? Something , it turns out. We start with Corissa's baffling post office experience (like in any good panto, the button is behind you! ) and we tumble into the world of Norman Doors, affordances, and why bad design persists even when everyone knows it's bad. We turn the lens on our...
123: Unpacking the Go-To-Market Sprint 07.10.2025 54:28
You've got a brilliant idea. Everyone agrees it could work. So why has it become the project nobody wants to hear about anymore? We dissect our Pitch Provocations method and package it up as a Go To Market Sprint that compresses 12 months of market learning into 3 weeks. We use a real agency case study to work out how to explain what we do (and realise we forgot to check how the story ended). This...
122: Platform Incentive Gravity 16.09.2025 16:21
Platform incentive gravity: it's why all the rental bikes end up at the bottom of hills, and why the most "popular" game on Roblox rewards you for doing absolutely nothing. Tom's teenagers declare Roblox dead, overrun by "slop games" where 200 million people "play" by opening the game and walking away. Meanwhile, the rich, creative games they actually love are withering with tiny player counts. We...
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