Obsidian Memo] Leadership Ground Truth: What Cuba and Puerto Rico Taught Me About Capital

The only thing more powerful than hate is LOVE.

"How Did You Find the US Football Halftime Show?" My Friend Asked Me the other day.

I have to be honest, I hadn't even heard about Bad Bunny until that very moment. The question caught me off guard. Bad Bunny's Super Bowl halftime performance wasn't just entertainment to me—it was a portal back to memories of Caribbean islands that shaped how I see politics, economics, and resilience.

Cuba: The Forbidden Land

I still hear the pilot's voice crackling through the intercom: "Ladies and gentlemen, I never thought I would say this in my life—but we are approaching Cuba. If you look out the window on the left side, you'll be able to see the land."

It was right after Obama opened the door in 2016. I wanted to visit before relocating to London in 2017—to see with my own eyes the forbidden land we couldn't even dream of visiting.

My timing was surreal. Coincidentally, I arrived during Fidel Castro's funeral, during national mourning. No alcohol. No parties. The markets and ration stations told the story socialism's textbooks never did—poverty infiltrated into everyday life. Even the policemen made me uncomfortable, their attention lingering on what I suppose was the rare sight of an Asian woman on those streets alone. Yet, one thing stayed with me. The culture and people's smile and loving presence, no matter how hard things are.

I walked through the Che Guevara museum, along the coastal Malecón, asking myself: why didn't their system take off? Why do democracy and capitalism still persist as the dominant systems today? The revolutionary passion was palpable in every mural, but the reality on the ground told a different story.

Puerto Rico: The Atlantic's Lessons from Accidental Discovery to Climate Risk

I first visited Puerto Rico as a tourist, not an investor. It was a quick weekend getaway from Manhattan—Atlantic beaches, rum, and the carefree energy of a spring break destination.

I accidentally stumbled into a marathon happening on the island. That's where I first learned people travel the world to participate in these races—a concept that seemed foreign to me then, but planted a seed that would stay with me.

Puerto Rico came back on my radar years later, but through a different lens—the devastating 2017 blackout. What was once my weekend escape became a case study in municipal debt default, climate risk, and infrastructure failure. The island that partied became the island that waited in darkness. For years.

The contrast haunted me. I'd lived through Hurricane Sandy in 2013 in New York—fleeing Manhattan for Jersey in what felt like a Hollywood disaster movie. Our blackout was addressed within weeks. Puerto Rico's took years.

Watching Bad Bunny's halftime show, I realized he was bringing that reality to public awareness—the island America remembers for spring break but forgets when the lights go out.

This is where sustainable investing becomes real, not theoretical. Physical climate risk isn't an ESG checkbox—it's the difference between a two-week recovery and a multi-year humanitarian crisis. It's the gap between how we treat citizens in Manhattan versus San Juan. It's why the same hurricane produces completely different investment outcomes depending on whose infrastructure fails.

The Atlantic Ocean around Puerto Rico taught me about more than trade routes and colonization history. It taught me that geography, governance, and capital allocation determine who recovers and who gets left in the dark.

Reflections: The Island That Became a Warning

Bad Bunny's performance carried another layer I couldn't ignore—his deliberate cultural resistance echoing Ricky Martin's earlier stance: Puerto Rico must not become another Hawaii.

Hawaii is my spiritual home. The islands where historically, after WWII, Japanese, Korean, and Chinese migrants came for sugar cane and pineapple farms now have a population that's over 37% East Asian descent. I found comfort there, familiarity in the faces and flavors. But once you hear the history of the indigenous Hawaiian people—their language nearly erased, their land commodified, their culture turned into tourist performance—you cannot help but wonder about the cost of that transformation.

Hawaii was annexed in 1898, became a state in 1959, and transformed into America's Pacific resort. Puerto Rico was also acquired in 1898, remains a territory, and now stands at a crossroads. Both islands: strategic military assets, economic dependencies, tourism economies. But Hawaii's path showed what complete cultural absorption looks like—where the Aloha spirit became a brand and native Hawaiians became a minority in their own homeland, priced out by mainlanders buying second homes.

That's the future Bad Bunny was pushing back against. Not just economic exploitation, but cultural erasure disguised as development.

Sometimes a halftime show isn't just a halftime show. Sometimes it's a reminder of the islands we've visited, the systems we've questioned, and the people whose stories deserve more than a fifteen-minute performance to be understood. Sometimes it's an artist drawing a line in the sand: this far, no further.

The Leadership Lesson

As investors, we're trained to read balance sheets and model risk. But I found the best investment decisions come from reading what the spreadsheets can't capture—the boots-on-the-ground reality of how systems actually function, how capital flows through societies, and why some structures create value while others destroy it. Ground truth beats theoretical models every time.