AI is eventually going to wipe out a lot of private equity and investment banking analyst roles. It will be same with junior roles across legal, accounting and other high paying careers. AI can be shit at times but let’s not kid ourselves, the models will keep getting better. One thing AI will never be able to do is tell stories. That’s one edge we will always have. My thesis is that all lucrative roles will have to be those that leverage stories. So I’m investing in that skill. How are you improving your storytelling skill?

Many senior professionals go through an existential crisis at some point - continue to bank the cash in a soulless job or take a risk and do something more fulfilling. Most professionals in banking, consulting and other high-paying careers find out sooner rather than later that they are a tiny cog in a large corporate wheel. I started my first job in February 2006 so many of my peers are going through this right now. In the past few weeks, I've spoken with a few who are considering leaving their stable corproate gig for entrepreneurship. Here's a combination of what I shared, that I wish someone had told me before I set out on my own. 1️⃣ It is okay to remain at a 9 to 5, as long as they will have you. Don't leave a job just because the internet says the only way to freedom is to start a business. 2️⃣ If you have to be an entrepreneur, know what you're getting into. Give yourself a long transition by starting something on the side. 3️⃣ Don't found a tech startup, it is a trap. Just don't do it 4️⃣ Similar to 3), start something you are comfortable with, shiny is miny so it always looks like you could be a great restauranteur because you want nothing to do with banking for instance. 5️⃣ Whatever time you think you need before your business stabilises, multiply that by 5. Think it will be 6 months, 3 years is more realistic. 6️⃣ Prepare for the culture shock when you drop your fancy corporate title, people will instantly treat you differently. 7️⃣ You need a support system - spouse, friends, and other entrepreneurs. No matter how awesome you are, you will not make it without this. What's the best advice you received to help with your transition from corporate life to entrepreneurship?

Picture this... You're a partner at a top VC, It's September 2026 and one of your portfolio companies is asking for advice as it seeks to raise next round of funding. The company is raising a $45m Series C at a $400m valuation and wants to seal the deal before the end of the year. In the summer of 2022 you led the Series B, investing half of the $40m round at a $250m valuation. Since then the company has grown: ✅ ARR from $8million to $20million ✅ Customers from 2,500 to 6,000 ✅ Headcount from 30 to 75 However, like a lot of startups, the company is not yet profitable but has about 9 months of runway. What would your advice be to the founder?

Liz Upton does not follow convention, pair that with a massive risk tolerance and you have ingredients of a successful entrepreneur. Her path from food blogger to co-founder of Raspberry AI, an LSEG listed company is a pretty rare success story. She was a great guest and we chatted about everything from community and risk to building one of the UK's best-selling computers. Oh.. and how she learnt to solder! You'll need to listen to the full episode to find out who taught her. kayfin.co/23milepodcast24 @23milecapital

When I started building Caena 5 years ago, one thing I quickly found out was that entrepreneurship is a group activity and not a solo one. Since then, I’ve joined many founder communities which have all served their purpose. But now I’m building one, well a super simple version for London and environs. Just a group of founders coming together to help each other with what matters most. In this case, I believe going from a company that sustains you to one making over a million pounds in revenue is the most critical part of the journey. Many just don’t make it. There will be no membership fees, yoga or any bells and whistles. It’s purely to help each other grow. Think of it as an opportunity to build a board of advisors of people who get it and have your interest at heart. If you want to know more, send me a message or leave a comment. By the way I’m deeply passionate about good coffee so I suspect coworking locations will have that. 📸 I think I’ve found a good spot, shout out if you can identify it

Who is the banker is wrong question. What’s debt figure? Nearly 8 trillion so bank charges is ~2% annualised. Makes sense.

The world may feel like it sucks but if we take a moment to marvel at technology, we realise humans are amazing. @Starlink on @emirates Great combo

Tell them

Using AI to create decks can be good but only if you put in some work. Simple prompting will generate "lazy", generic slides that will get get dismissed as AI slop. Here's a simple process that gets much better results with Claude 1) Sample: give Claude 3 to 5 examples of decks you've built in the past, include other quirks and design principles like font and colour. 2) Systemise: ask Claude to turn these into explicit design principles or “skills”. 3) Suppress: and this is important, explicitly tell Claude to avoid defaults. 4) Supply: AI does best when working within closed constraints, provide all inputs perhaps in a word doc. 5) Sharpen: you should have a deck that looks unique but spend time tweaking and refining for a better quality deck. Give it a shot especially for decks where the outcome matters to you.

I'm conscious everyone has a hot take on AI and there's little middle ground but this from Kyle Harrison is a good one. Use AI for writing and for decks but pls pls put in some work to customise it. Here's a simple approach you can try: 1) Sample: give Claude 3 to 5 examples of decks you've built in the past, include other quirks and design principles like font and colour. 2) Systemise: ask Claude to turn these into explicit design principles or “skills”. 3) Suppress: and this is important, explicitly tell Claude to avoid defaults. 4) Supply: AI does best when working within closed constraints, provide all inputs perhaps in a word doc. 5) Sharpen: you should have a deck that looks unique but spend time tweaking and refining for a better quality deck. Give it a shot especially for decks where the outcome matters to you.

Quick quiz: do you know how many women have taken a startup they co-founded public in the UK in the past ten years? Well, in 2024, @Liz_Upton was the only female co-founder of a company that went public in the UK and one of only three across Europe. Her journey to the London Stock Exchange LSEG wasn't intentional. Back in 2011, Liz was having a pretty good time in journalism as the author of one of the UK's top food blogs and co-author of a bestselling National Geographic book. When a fledgling, pre-product startup needed her help to market their product ahead of launching, she reluctantly agreed to help them out for a few months. The startup happened to be her husband, @EbenUpton's company and a few months became a 14-year journey. Raspberry Pi ended up becoming the UK's best-selling computer and hitting a billion-pound valuation after IPO. In this episode of the 23mile Podcast, Liz talks about: ✅ Taking the unusual decision to mortgage their houses and build the company without venture capital ✅ How she built the community that became Raspberry Pi's moat ✅ The chaos of launching with 2,000 computers and receiving 100,000 orders ✅ What she's now doing to support the next generation of deep-tech founders through Negroni Venture Studios, and as Chair of OLO Robotics and Coherence Engine I really enjoyed speaking with Liz, episode is now out on Spotify, LinkedIn and Apple Podcasts kayfin.co/23milepodcast24 @23milecapital

My thoughts, founders shouldn’t let startups with good customers go to zero. Pulley may no longer be venture scale but it could have run as a good business. nitter.cf/kayodeodeleye/status/2…

How important is community to scaling a tech startup? Back in 2011, Liz Upton was enjoying her career as author of one of the UK's top food blogs and co-author of a bestselling National Geographic book. She agreed to take a break to help her husband's fledgling startup with marketing as they prepared for launch of their experimental product. Her work building the community helped turn that idea into the UK's best-selling computer of all time and a billion-pound valuation. This was a really exciting conversation 🎧 Episode out Thursday 17 September. @23milecapital

Imagine raising 50 million dollars in funding from some of the biggest names in the investment world and being a household name amongst your clients in the US and globally. Huge success, right? Yes, but only for a while. Most venture backed businesses don't become profitable for years meaning they are just one funding round away from failure. Endless cycle of raise >> scale >> raise. As a former tech founder, it is sad when startups fail as founders pour their blood and sweat. Sad to see Pulley throw in the towel. The biggest tragedy are the solid businesses (real customers and good business model) that end up shutting down. It's the simple message I've been banging on about for years, failing to raise does not mean you have to shut down. What successful steps have you seen founders take to save company from failure?

367 days post Achilles Rupture. Couldn’t be happier with longest run in 18 months

Well done guys, distressed M&A is net positive for venture. We will see more even among earlier stage nitter.cf/kayodeodeleye/status/1…

Lots more to come. Every inflated fundraise of the SaaS era ends at best like this distressed M&A or worse still complete shutdown. nitter.cf/kayodeodeleye/status/1…

Some say AI is a passing fad... No, it is by far the biggest technological shift of our lifetime. So says Joshua Summers a four-time founder, with previous exits to Paypal and AT&T, he has seen it all. He was there for the advent of the internet and is now at the forefront of AI, building EnFi, Inc, an agentic credit platform for banks. Full episode of Finance Upturned with Kayode Odeleye now streaming kayfin.co/financeupturnedpod…

A few months ago, Standard Chartered CEO got into hot water for saying his bank was going to “replace lower-value human capital” with investment in AI. Though Bill Winters later apologised for causing upset with his comments, he did not retract the underlying point. It reveals how some senior bankers are thinking about AI and back-office functions in the future. When I asked Joshua Summers, my latest guest on the Finance Upturned podcast, he says: “not yet.” But he sees something potentially more significant: AI allowing banks to grow much faster without growing headcount at the same rate. Which is exactly what his AI startup ENfi does. Fingers crossed this continues to be the case, with humans and AI working together to increase efficiency. Finance Upturned episode 2 now streaming on Substack kayfin.co/financeupturnedpod…