Identity leverage doesn’t compound

In the early 2000s, I had a South American roommate in my penthouse loft in Toronto. Total rico suave archetype. He did exceptionally well socially—places like the Drake Hotel were almost tailor-made for him. He even nudged me into making my first serious real estate move: buying a penthouse across the street.

At the time, he was riding the cultural momentum of the Latin music and nightlife wave. It worked—effortlessly. There was a real social tailwind.

Charisma, machismo, rhythm, presence. The moment rewarded it.

I was still figuring myself out then—both personally and in markets—but I paid close attention. I absorbed what it looked like to have that kind of immediate social pull, and what it meant to move through the world with momentum you didn’t have to manufacture.

I think back now and ask whether that same archetype would work in 2026.

The honest answer is: not in the same way.

That form of identity leverage relied on performance—on a very specific expression of masculinity and cultural signaling. The world has changed since then. The incentives are different. The tolerance for certain performances has narrowed, and the upside from them has compressed.

By contrast, I’ve always been a slower burn. Less dependent on timing, more dependent on compounding. What I built wasn’t optimized for a moment—it was built to persist across moments.

That difference matters more with time.

Identity waves and externally controlled - come and go.

Skill compounds.

Judgment compounds.

Execution compounds.

Identity attention doesn’t.

It’s consumptive, not accumulative.

It gives reach without building internal advantage.

When the cycle turns, there’s often nothing underneath.

Any strategy that relies on that is fragile by design.