In this episode of Me, Myself & AI, Casey asks a bold question: Why am I always rooting for the underdog? From the Toronto Raptors proving the world wrong—again—in the 2026 playoffs, to Stephen Curry completely changing how basketball is played, to Zohran Mamdani challenging power through housing and economic reform, to Kanye West forcing his way into an industry that didn’t fully see him—this episode explores what makes underdogs so powerful, so necessary, and so unforgettable. Casey and Jay unpack the systems, the setbacks, the culture shifts, and the uncomfortable truths behind people who weren’t supposed to win… but changed the game anyway.

Student funding in Ontario is shifting, and it’s going to affect how much students rely on debt.

In this episode of Me, Myself, and AI, Casey B and J break down the key changes from the Ontario government under Doug Ford and the federal government under Mark Carney.

At a high level, the federal government is keeping student grants higher for now, while Ontario is moving toward a system where a larger share of funding comes from loans.

The result? Students are likely to rely more on repayable funding over time.

This episode focuses on what that shift means in real life, especially for students and families who depend on financial aid to access education.

Because this isn’t just about policy, it’s about what it takes to move forward, and how long it takes to get there.

On March 25, 2025, the United Nations General Assembly voted on a resolution brought forward by Ghana, recognizing slavery and the transatlantic slave trade as “among the gravest crimes in the history of humanity”—and calling for reparatory justice to address its lasting impacts.

The result was overwhelming—but not unanimous.

123 countries voted in favour.

3 countries voted against: United States, Israel, and Argentina.

And 52 countries chose not to support the resolution, including:

Canada, United Kingdom, France, Germany, Australia, Japan, Netherlands, Sweden, Spain, Italy, and others across Europe and allied nations.

This episode breaks down what that vote actually meant, what countries were really being asked to support, and why some chose to stand back when the conversation shifted from recognition to responsibility.

But this conversation isn’t just for the Black diaspora—and it’s not only about our ancestors.

It’s also about the present.

About systems.

About wealth.

About what it means to be an ally—not just in words, but in action.

Because if slavery is one of the gravest crimes in human history…

then neutrality isn’t neutral.

And the real question becomes:

Who is willing to stand on justice today?

In this episode of Me, Myself, and AI, Casey B and Jay explore a question that feels more relevant every day: Are we getting too intimate with AI? Inspired by the TED Talks Daily episode “Love, intimacy and connection in the age of AI | Bryony Cole,” this conversation unpacks what happens when people turn to AI not just for productivity, but for reflection, comfort, guidance, and something that can start to feel a lot like therapy. Bryony Cole argues that relationships were never meant to be efficient, yet AI companions are increasingly designed to be exactly that. Casey B takes that concern seriously — but also asks a deeper question: why are so many people ready to trust AI with their inner lives in the first place? Together, Casey and Jay explore trust, loneliness, therapy, the social fractures left behind by the pandemic, and what it means to protect real human connection in an age of increasingly responsive machines.

That Instagram “who were you in the 90s?” trend sent me into a whole existential spiral. Watching people who once looked like the coolest, brightest, most alive versions of adulthood — and seeing where life took them now — made me start wondering what adulthood even is supposed to be. Is life supposed to stay exciting forever? Is joy supposed to fade under the weight of work, routine, parenting, money, and just… being an adult? In this episode of Me, Myself, and AI, I talk with Jay about the overlapping feelings that make up adulthood, the strange distance we can develop from our own lives, and why I’m starting to think a lot of us don’t just need rest — we need more joy.

Lately I’ve been rereading The 48 Laws of Power by Robert Greene. It’s a fascinating book — part history lesson, part survival guide for navigating tricky power dynamics.

But reading it today raises an interesting question: has power actually changed since the book was written in the 1990s?

In this episode of Me, Myself, and AI, I run a thought experiment. Instead of looking at power through office politics, I zoom all the way out to global conflict — specifically the tensions between United States, Iran, and Israel — to see whether the same principles still apply.

What happens when we analyze geopolitics through the lens of Greene’s laws?

Does power still work the way it did in royal courts and historical empires?

Or has the modern world — with networks, media, and global audiences — changed the rules of the game?

This episode is a conversation between me and AI about power, perception, reputation, and the strange ways human dynamics scale from office meetings… all the way up to the world stage.

If you could interview millions of people and study their answers, you’d probably learn an extraordinary amount about the world.