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Sensemaking with Wolé and Tobi

Sensemaking with Wolé and Tobi

De: Wolé and Tobi
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Sensemaking (formerly titled 'The Yellow Pill') is a podcast where Wolé and Tobi navigate life, work, technology, and culture with thoughtful conversation, personal clarity, and modern insight, one honest episode at a time.

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  • 118: The Case for Getting Your Hands Dirty
    Apr 13 2026

    What begins as a DIY story turns into a conversation about why some cultures build things themselves, and others have forgotten how — and what gets lost when an entire generation grows up treating practical skills like they don't count.

    We get into education, labour, cost, and craft.

    Why does a carpenter send his son to study medicine? Why did we spend years labelling insects in school but never take workshops seriously? And what happens to quality — in roads, in work, in training — when nobody sticks around long enough to learn a trade properly?

    There's also something in here about just starting. About the gap between the person who plans and the person who doubts, and what it looks like when one of them picks up a shovel anyway.

    If you've ever talked yourself out of trying something because it seemed too hard, or wondered whether the things you learned in school actually prepared you for anything useful, this one's for you.

    . . .

    If, while you're listening, something crosses your mind, or you get that urge to jump into the conversation, we'd love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

    Join our WhatsApp Community for episode alerts and to chat with other listeners and us: https://chat.whatsapp.com/E1zfJLM46L01jR809JmURz

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    36 m
  • 117: Why Your Favourite Tech Company Might Not Survive
    Mar 30 2026

    You use their apps every day. You've watched their stock prices climb. Maybe you've even built your career around their tools.

    But what if the tech companies you rely on most can't actually explain how they make money?

    In this episode, we get into something that's been on both our minds for a while — the growing gap between what the tech industry celebrates and what it actually delivers.

    We're not coming at this as industry analysts or investors, but think of us as two people who use these products, work in and around tech, and have started to notice that a lot of what gets called "innovation" doesn't seem to solve problems anyone actually has.

    We talk about AI — what's changed recently, what the difference is between the tools that just talk back to you and the newer ones that can actually do things on your behalf, and why that distinction matters even if you've never written a line of code.

    We go company by company and ask uncomfortable questions. Why has one of the biggest names in AI backtracked on so many promises? Why does a company worth billions still not have a clear product focus? And why are some of the fastest-growing tools in tech already showing signs they won't last?

    So we put together a test. Three fundamentals that any business — tech or not — should be able to answer.

    • Is there a real problem worth solving?
    • Is there a reason for people to choose you over the alternative, or over doing nothing at all?
    • And do the economics actually work — are you making more than you spend to serve each customer?

    It's not complicated. But it's surprising how many of the biggest names in tech can't pass all three.

    We also zoom out and ask which tech companies have genuinely lasted. Which ones have become as permanent as a bank or a soft drink brand?

    The answer is shorter than you'd think, and it raises its own set of questions about what the last twenty years of tech have actually given us.

    . . .

    Jargon Decoder — a few terms we throw around in this one, explained plain:

    • Agentic AI — AI that can take actions for you (book a flight, fill out a form, organise your files) instead of just answering questions in a chat window.
    • Generative AI — AI that creates things — text, images, code. ChatGPT is the most well-known example. When someone says "AI" casually, this is usually what they mean.
    • Unit economics — whether a company makes more money per customer than it costs to serve that customer. The most basic maths of whether a business can survive.
    • Future state selling — pitching investors on what a product will do someday, rather than what it does now. A red flag when the "someday" keeps moving.
    • Moat — what stops a competitor from copying your business. Borrowed from the idea of a castle moat — something that protects you.

    . . .

    If, while you're listening, something crosses your mind, or you get that urge to jump into the conversation, we'd love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

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    49 m
  • 116: When People You Rated Stop Making Sense
    Mar 23 2026

    What happens when something you used to believe doesn’t make sense anymore?

    In this episode, we get into that experience of going back to people, ideas, or opinions you’ve held for a long time, and realising you’re not as convinced as you once were.

    Sometimes it’s obvious why. Other times, you can’t even trace where the belief came from, but it’s just been there.

    So we try to unpack that.

    • Why did this make sense to me before?
    • Was it the idea itself, or the person saying it?
    • And what does it actually mean to change your mind?

    We also talk about how this shows up with public figures. People you used to listen to, agree with, or rate, and then, over time, you just stop connecting with.

    And even between us, we realise we don’t handle it the same way. Sometimes it’s a slow drift, where you just stop paying attention.

    Other times it’s more direct, you hear something, and you’re like, yeah… I’m done.

    That opens up a few other things.

    Like why some people never really evolve with their audience. How easy it is for your identity to get tied to certain beliefs. And how you can end up holding onto views long after the moment that made them useful has passed.

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    .

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    If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

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    34 m
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