Opinions expressed by Entrepreneur contributors are their own.
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.
The lesson is universal: When a market enters crisis, the assets do not become worthless. The capital leaves, the operators leave, but the fundamental value remains. Entrepreneurs who can distinguish between a broken economy and a broken narrative will find their best opportunities in exactly the places everyone else is avoiding.
Showing up matters more than your spreadsheet
I could have analyzed Puerto Rico from an office in New York. Instead, I spent weeks on the ground talking to local operators, municipal officials, business owners and community leaders. What I discovered was an island that was desperate for investment — not charity, but real operational commitment.
When I started acquiring assets, the previous owners had deferred maintenance for years. Facilities were deteriorating. Equipment was outdated. Customers and tenants were leaving. The turnaround required more than capital. It required presence, relationship-building and a willingness to solve problems that no financial model could have predicted — from navigating post-hurricane permitting to hiring and training local teams in a labor market that had been hollowed out by emigration.
This is something spreadsheet investors consistently miss. Real asset deals in distressed markets are not won by the highest bidder. They are won by the person who shows up, earns trust and commits to staying. Community relationships become your competitive moat — and in Puerto Rico, that moat runs deep.
The recovery you are not hearing about
The Puerto Rico of 2026 bears little resemblance to the island I arrived on in 2014. The numbers tell a remarkable story.
Unemployment has dropped from over 13% to a historic low of 5.6% — the lowest sustained rate in the island’s history. Private-sector employment reached a record 767,400 jobs in 2025. Tourism has posted four consecutive record-breaking years, with 6.8 million airport passenger arrivals in 2025 alone. Over $2.6 billion in new investments were announced last year. More than 12,500 reconstruction projects, valued at nearly $17 billion in federal funds, are currently underway.
The island officially exited bankruptcy in March 2022. The government recently extended its Act 60 tax incentive program through 2055, offering a 4% corporate tax rate for qualifying export services and favorable treatment on capital gains for resident investors. Net migration has stabilized, and anecdotally, skilled workers are beginning to return.
None of this happened overnight. It took a decade of painful restructuring, devastating hurricanes and stubborn rebuilding. But the trajectory is unmistakable.
What entrepreneurs should consider before making the leap
Puerto Rico is not a shortcut. Entrepreneurs who come solely for the tax incentives without a genuine commitment to operating on the island tend to struggle. The real opportunity belongs to those who see Puerto Rico as a place to build — not just to shelter income.
If you are considering it, here is my honest advice from 12 years of operating there:
First, come in person. Spend time outside San Juan. The East Coast, the South and the West all have distinct economies and communities. Your business model needs to match a real local need — not just a tax optimization strategy.
Second, plan for complexity. Permitting, utilities, logistics and supply chains in Puerto Rico all require patience and local knowledge. Build relationships with local professionals who know the regulatory landscape.
Third, think in decades. The entrepreneurs who have done well here are the ones who committed to the long term. The island rewards patience. It punishes opportunism.
Puerto Rico taught me that the best business decisions often look like the worst ones in the moment. In 2014, betting on a bankrupt island felt contrarian to the point of recklessness. A decade later, it has been the most consequential business decision of my career.
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.
