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Key Takeaways Crisis is where the real deals are: When a market enters crisis, the assets do not become worthless — the fundamental value remains.
Real asset deals in distressed markets aren’t won by the highest bidder. They’re won by the person who spends time on the ground, builds relationships, earns trust and commits to staying.
The best business decisions often look like the worst ones in the moment. If you’re willing to look past the headlines, you can find great opportunities in the places everyone else is avoiding.
In 2014, when I first landed in Puerto Rico to explore business opportunities, the island felt like a place the world had given up on. The government was drowning in what would become a $72 billion debt default. Unemployment was above 13%. Entire neighborhoods had boarded-up storefronts and aging infrastructure. People were leaving — between 2010 and 2020, Puerto Rico lost nearly 12% of its population. Everyone I spoke to on the mainland told me I was making a mistake.
I moved forward anyway. What I saw was not a failing economy but a mispriced one — an island with extraordinary natural assets, a skilled workforce, U.S. legal protections and deep cultural resilience that was being valued at its lowest possible point. Over the following years, I built a portfolio of real assets across the island. Today, the island’s transformation has been so dramatic that the same people who questioned my decision are now asking how to get in.
Here is what I have learned about betting on a place when nobody else will.
Crisis is where the real deals are
When credit agencies downgraded Puerto Rico’s bonds to junk status in 2014, capital fled. Businesses that depended on government contracts or local consumer spending struggled. Real estate prices collapsed. For most investors, this was a signal to stay away.
But for someone willing to look past the headlines, the distress created an extraordinary window. Real assets that would have been fiercely competitive in Florida were suddenly available at a fraction of their replacement cost. The regulatory approvals and permits attached to those properties — which take years to obtain in normal conditions — came with the deals. The underlying demand had not disappeared. It was just waiting for someone to invest in the infrastructure.
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