Partner Venture Capital Special Situation Fund @23mile | Host, 23mile Podcast (Tech M&A and Turnaround Stories)

Joined March 2009
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14 Aug 2025
If I knew what I knew now, I wouldn't have raised venture capital." This is what a founder friend told me the last time we caught up. Two big headaches he's facing: 🥵 sheer weariness from fundraising every year for the past 12 years ❌ constant challenge of meeting sky-high targets after his recent growth equity round And he's one of the lucky ones who has taken some "chips off the table." The fact is that for many founders, the VC path becomes a death spiral, leaving them broken with nothing to show for it That's why we've put together a framework to help founders think through their options and escape the VC hypergrowth model Give it a read if you're on the venture path, thinking of it, or just want to know how venture really works💡 Details below 👇🏽 @23milecapital
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AI checkers may be inaccurate but trust your own instincts If it reads like AI, then it's AI If it's something anyone could have written then it's as good as AI slop
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Once you see it, you can't unsee it. There's AI writing everywhere and it's so obvious. What's harder to say is what makes it clear a piece is AI writing. I'm finalising a piece on how to write with AI without sounding like AI and I'm eating my own dog food. I'd generated a draft paragraph (left) which I then completely rewrote (right). When I passed my draft back to Claude, here's how it compared both versions: ✅ Casual, conversational and slightly meta ✅ The author's personal experience using AI ✅ A behind-the-scenes trick ("I had Claude produce..."). while it's own version was ☑️ Authoritative, commanding, and highly professional ☑️ The reader's professional accountability and judgement ☑️A heavy, resonant anchor ("This stage belongs to you.") So here's the question, do you prefer the "perfect" AI writing or the human version? And why?
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Important for those who care and understand to do their bit x.com/kayodeodeleye/status/2…

I do find it extraordinary that current events in AI don’t make the top ~30 stories on the BBC News homepage
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The narrative violation around A.I. adoption is stunning You’d think younger generation would embrace new technology at a faster rate than older one. With genAI it’s the other way round. GenZ have a strongly negative view to AI which is understandable when you hear them out. I’ve had lots of conversations this week on how older professionals owe younger ones a duty to help them navigate this change. Open to any ideas you’ve seen work out well…
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Your chances of raising venture capital as a first time founder is exactly ZERO I was speaking with a group of founders at a pitch event this week on the complexity of early-stage fundraising When starting out, it seems it can't be that hard - so many VCs invest at pre-seed right? Wrong! Chances of raising from institutional investors is near ZERO if you're not 0.0001% of top founders Jinesh Vohra talks about raising a first round of £300k round from F&F and then the second round from angel investors This strategy worked out as the initial rounds allowed Sprive to achieve enough traction to raise from some of the UK's largest VCs and much recently a £5 round on Republic Europe, taking it's total funding to over £12 million See full episode for how he's managed the funding journey and scaling the business kayfin.co/23milepodcast21 #fundraising
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I used Fable extensively in the 3 days since launch and it’s definitely overhyped Super expensive and still worked like an erratic intern you need to scream at 5x to get basic tasks done Now this 🤔
The US government, citing national security authorities, has issued an export control directive to suspend all access to Fable 5 and Mythos 5 by any foreign national, whether inside or outside the United States, including foreign national Anthropic employees. The net effect of this order is that we must abruptly disable Fable 5 and Mythos 5 for all our customers to ensure compliance. Access to all other Claude models is not affected. We apologize for this disruption to our customers. We believe this is a misunderstanding and are working to restore access as soon as possible. Read our full statement: anthropic.com/news/fable-myt…
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Are GenZ and new grads just being spoilt with their approach to AI? Or are they justified in feeling threatened by a technology that targets them? This week's roundup has some positives from executives starting to understand that young professionals have genuine reasons to fear, and they need help 1️⃣ A new YouGov poll finds 55% of 18 to 24 year olds would erase AI for good, the highest of any age group 2️⃣ Stanford finds young workers in the jobs most exposed to AI are losing out, while older workers in the same jobs are fine 3️⃣ The FCA won't write new rules for AI. It says the rules it already has are enough to hold firms to account 4️⃣ KPMG's own report on the upside of AI turned out to be full of made-up sources, so it quietly pulled it 5️⃣ A judge threw all four lawyers off a case after both sides handed in briefs citing cases AI had invented 🫣 6️⃣ OpenAI has filed to go public at an $852bn valuation 💸 7️⃣ The UK 🇬🇧government is spending £20m to keep entry-level jobs open for young people 8️⃣ Microsoft's president says the graduates booing AI are telling the industry what it needs to hear 9️⃣ Crédit Agricole's CEO is putting €500m into AI and says he won't cut any jobs 🔟 Opendoor is closing its India office, letting 250 people go, and hiring in the US instead 🔖 See the full Finance Upturned issue for what all this means for finance professionals
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See full roundup and don't forget to subscribe 🚀 kayfin.co/financeupturned06

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It's 2026 and professionals still don't know how to use AI SMH x.com/Kayodeodeleye/status/2…

Amazing: KPMG wrote a report describing the successful use of AI by businesses. But the case studies turned out to be AI hallucinations. giftarticle.ft.com/giftartic…
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Feels like the timeline is turning into Moltbook A slurry of writing that’s all very correct and polished and florid, and all lifeless in exactly the same way It would actually be better if people just tweeted the prompt they gave Claude rather than the output it gave them
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It's quite common for bootstrapped founders to go years without getting paid, that's the price of building something from nothing. It's less common for a founder who has raised funding, lots of it from some of the UK's biggest VCs, to deny himself for four years. But that's just one of the sacrifices Jinesh Vohra had to make to take Sprive to the heights it's reached today as one of the UK's most popular finance apps, helping over 160,000 homeowners pay off their mortgage faster. In this episode: 💼 Why he left fourteen years at Goldman Sachs and what he gave up to do it 🤝 Telling his wife she'd never have to work again, then having to ask her to go back 📱 The LinkedIn waitlist that brought in 2,000 sign-ups before launch with no paid marketing 🔄 The pivot that saved the business when the cost of living crisis killed his original model 👶 Getting his kids to scream in his ear while he practised his Dragons' Den pitch 💰 What Dragons' Den actually delivered commercially, beyond the three Dragons and 5% of the business Episode 21 of @23milecapital podcast is out now on YouTube, Spotify and Apple Podcasts.
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Do you use AI to write? You’re doing yourself and your audience a disservice. AI is great at a lot of things but generating blogs, emails or comments is not one of them. Here’s why: writing is about communicating character, personality and knowledge to an audience. AI writing defeats the purpose on all three counts. That’s why many people especially VCs refuse to read emails or decks created by AI. They see it as a sign of sloppiness. See an example in the video or in greater detail in this week's Finance Upturned #artificialintelligence kayfin.co/financeupturned05
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I like levels but this is dishonest His GF bought a plastic Rimowa and he’s whining not stop about it breaking Dude buy the real thing or move on
Update on the Rimowa story: we flew Copenhagen to Lisbon now They somehow managed to do this to it 😂 $1000 suitcase! 🤡 P.S. I didn't buy it, my gf did, she's more susceptible to brand value (and paid influencers) Rimowa I think is really just way worse than any $100 Samsonite or American Tourister suitcase that never breaks If you want to pay 10x more for 10x less buy Rimowa (or anything owned by LVMH) Stay away from luxury brands!
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Too hot to run outdoors in Dubai so today was a strength and run class
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This is just terrible management using claude usage as a KPI Why is no company focusing on outputs?
Last month: Management was pushing us to hit 100% AI adoption, so half the team was basically having casual chats with Claude just to boost AI usage metrics for performance reviews. This month: Mandatory sessions on Copilot token optimization and reducing AI consumption. My org moved from "use more AI" to "please stop using so much AI" in about two weeks. 😂
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Kayode retweeted
Great content does one of three things: 1. Teaches something you did not know. 2. Educates you on something you thought you knew but you were wrong on. 3. Tells you a secret/miracle that changes everything you previously thought.
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This week I hosted 21st episode of my podcast and the biggest lesson is this Achieving success as an entrepreneur takes a long time. Nothing is as important as staying alive until tide turns in your favour
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Banks and finance will be a fertile hunting ground for A.I. native startups x.com/kayodeodeleye/status/2…

If big companies can't make a net return on their LLM token costs, that doesn't mean it's impossible to. In fact this is exactly what you'd expect to happen with a new technology. Incumbents can't use it well, and are replaced by upstarts who can.
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AI writing is abominable, here's a regeneration of a real blog I found The em dash used to be a sign of AI writing but for some reason it's now way way worse Here's a teardown of this blog 1⃣ The title starts with a figure of speech - Antithesis: when humans write, it's typically one coherent strand in a title and rarely with such rhetorical fluorish. The two full stops are also a dead giveaway 2⃣Short sentences: if you want to know how odd this is, read out the first 2 lines (4 sentences) out loud. The left panel squeezes 52 words into 9 sentences with the shortest sentence having just one word. A natural writing style comes close to speaking cadence and combines sentences into paragraphs that support the main point. 3⃣Three clipped words (Tricolon) where one smooth sentence would do. And the main message in the staccato construction serves to emphasise the point made in previous sentence. 4⃣Negative parallelism: this short section of three sentences packs four different figures of speech. The main one is negative parallelism, two short sentences containing ‘never’ then dropping the word to deliver the punch line ‘judgement’. Tricolon, Anaphora and Asyndeton are also squeezed in Simply amazing! 5⃣The chain: the last word of one sentence becomes the first of the next, so each line seems to follow from the one before. In isolation, each of these figures of speech may sound smart and lends the author authority. Stacked tightly as it is in the full writing, you can’t avoid a feeling of deception. As a reader, I get the sense that the “author” could not bother to write with their own character, experience and distinct style. If they’ve fully delegated writing to a robot, then there’s not likely to be any value in reading it. I could just go generate the same thing on my own
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See full compilation and don't forget to subscribe There's a fun exercise on AI writing, check it out kayfin.co/financeupturned05

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