Nostalgia Is Holding Us Hostage

Why is there such an excitement about people being out of work?

I’m talking about the Oracle layoffs—30,000 people deleted from a payroll at 6:00 AM by a corporate noun with no face. But this isn’t just another post about “tough decisions” and “market headwinds.” It’s about the silence that follows when a decade of loyalty is answered with a DocuSign link at dawn. I talk about the reality of the corporate trenches: the political capital you burn to protect your team, the weekends spent fixing decks for bosses who don’t know your name, and the quiet, uncredited work that keeps the world turning—only to realize that to the people at the top, you are just “bloat” waiting to be purged. But more than that, I’m looking at the energy in the room when billionaires talk about AI. I’ve noticed a specific, physical kind of glee in their voices—a glow that comes from describing the elimination of human livelihoods like it’s a successful product launch. I contrast the cold inevitability of Oracle with the choice made by Ikea, who turned 8,500 call center workers into a billion-dollar design force, proving that mass unemployment isn’t a technological necessity—it’s a leadership choice. We’ve handed the keys to our entertainment, our information, and our democracy to a handful of people who prioritize outrage over joy. Now, we’re handing them the very concept of work. I’m not technophobic; I’m building a company with AI right now. I believe in the tool. But I don’t believe the people sending 6:00 AM termination emails are dreaming of a better world for you. They’re dreaming of a world that is clean, profitable, and entirely unburdened by the “inconvenience” of human beings. This episode is a question about what we are actually building towards. Because if progress means reaching 30,000 people via email before sunrise to tell them they no longer exist—who is that progress actually for? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leegray04.substack.com [https://leegray04.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

I'm back because I cannot afford therapy right now.

I’m talking about Cleared, my second venture: what it is, why I built it, and why I’m not going to dress it up in founder mythology and sell you a story about destiny. I started this company because I’ve seen first-hand what happens when the financial system can’t read you — when you’re earning, working, building, and still somehow invisible to the infrastructure that’s supposed to let you live your life. But this episode isn’t really about the business. It’s about what it actually feels like to do this a second time. When you know too much to be naive and not enough to feel safe. When two investors pull out over a weekend because of a war starting on the other side of the world. When the doors that were briefly opened to founders like me have quietly closed again — and been repainted to look like they were never there. I talk about the friends who are overqualified and underpaid, grinding through six-round interview processes for jobs they could’ve managed years ago — and why that takes a kind of courage we never put on a pedestal. I talk about the myth of the brave founder, who the safety net actually belongs to, and why risk tolerance is sometimes just a bank account with a different name. This isn’t a pitch. It’s not a highlight reel. It’s me, at the intersection of terrified and certain, trying to figure out if those two things can coexist long enough to build something real. Because if the traditional path no longer guarantees security, and the alternative path never promised it — what exactly are we all working towards? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leegray04.substack.com [https://leegray04.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Nostalgia Is Holding Us Hostage

In this episode, I ask the important questions: do we really need another Batman? Hasn’t Cinderella had enough traumatic shoe fittings? And who exactly demanded a Mean Girls movie of the musical of the movie? We’re talking about the endless parade of remakes, reboots, sequels, prequels, “gritty” reimaginings, and live-action adaptations that nobody asked for - from The Lion King: Beyoncé Edition to the Harry Potter reboot you didn’t put on your vision board. Yes, nostalgia sells. Yes, we all keep showing up for it. But at what cost? Are we so busy reliving the past that we’re forgetting to make space for the stories that could define the future? Plus, I pitch a few upcoming Hollywood hits you’ll be seeing soon: * Toy Story 12: Andy’s Funeral * Shrek 5: Donkey’s Divorce * Jurassic Park: The Pension Years If the only stories we tell are ones we’ve already heard… how will we ever surprise ourselves again? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leegray04.substack.com [https://leegray04.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Wear Your F*cking Clothes

In this episode, I’m holding space for one thing and one thing only: wearing your own damn clothes. Yep, that dress you wore to brunch last month? Wear it again. Those jeans that have seen every bottomless mimosa in the city? Wear them again. Somehow we’ve ended up in a world where repeating an outfit is treated like a scandal. Instagram has tricked us into believing visibility equals expiration. But unless you’re being paid to wear head-to-toe newness every week - baby, wear your f*cking clothes. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leegray04.substack.com [https://leegray04.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

What If Your Job’s Already Gone and You Just Don’t Know It Yet?

This week, I’m thinking about my first job at River Island on Oxford Street — the job that made it possible for me to intern at Vogue for free, survive London, and start building the career I have now. But if I were 16 today… would that job even exist? I was in Zara the other day, scanning my own items, realising: I didn’t speak to a single person. No one helped me, no one offered advice — it was just me, my card, and the algorithm. It got me thinking about how quickly AI has shifted how we work, how we shop, and how we survive. This episode isn’t about fear-mongering. It’s about facing what’s already happening. From CEOs cutting jobs in the name of “efficiency” to governments pretending like regulation is someone else’s problem, we’re watching a massive shift unfold — and too many people are acting like it’s still hypothetical. I talk about universal basic income, why $1,000 a month might sound cute but won’t save you, and how AI can either work for us — or erase the spaces that helped so many of us get our start. Because if AI is coming for your job, the real question is:What are you going to do if your politicians, CEOs, and safety nets don’t come to your rescue? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leegray04.substack.com [https://leegray04.substack.com?utm_medium=podcast&utm_campaign=CTA_1]