March 29, 2018 23 min read

This story appears in the April 2018 issue of Entrepreneur. Subscribe »

When Hurricane Maria raked across Puerto Rico last September with wind speeds of up to 155 miles per hour, it left a path of unprecedented destruction. The storm flattened houses and forests, flooded towns and made hundreds of thousands of people homeless. It knocked out most of the island’s power grid, leaving nearly all 3.7 million residents in the dark, and severed 95 percent of cell networks as well as 85 percent of aboveground phone and internet cables. Eighty percent of the island’s crops were decimated.

Related: Is Your Business Ready for the Next Devastating Natural Disaster?

Once the hurricane moved on, an all-too-common aftermath unfolded. Local emergency responders became overwhelmed. There was, memorably, public fighting among political officials — San Juan’s mayor versus President Trump. Relief agencies and volunteers flooded in. People who wanted to help could find long lists of organizations to donate to, though, as is typical after a disaster, it wasn’t clear where the money was best spent. Dollars often flowed indiscriminately. 

Ten days after the hurricane, a different kind of responder arrived on the island. His name was Jesse Levin, a 32-year-old serial entrepreneur with close-cropped hair and aviators, and the co-founder of a series of rock-climbing gyms called Brooklyn Boulders. He had no military background, though he had volunteered in past disaster zones and spoke the language of relief — casually discussing “air assets” and “force multipliers.” Before he arrived he’d made plans to help, help that didn’t necessarily involve the cluster of government agencies and NGOs that were scrambling to advance their operations. “It was mind-boggling,” he recalls now. “There was just completely ineffective communication going on.”

A rented jeep was waiting for him.

Once in Puerto Rico, Levin spent several days crisscrossing the island’s debris-strewn roads, talking to residents, business owners, mayors and policemen. He rarely came across an aid worker or a utility truck. In the media, he’d kept hearing that people were desperate for food and water. But in village after village, Levin encountered grocery stores open and stocked with enough provisions to sustain the local communities. Enterprising merchants had even rustled up generators to keep on the lights. But many customers couldn’t buy anything: Around 40 percent of Puerto Rico’s population depends on food stamps, which require Electronic Benefit Transfer (EBT) cards to make purchases. With the island’s telecommunications network down, the cards couldn’t be processed. This particular problem didn’t require an intensive governmental effort to distribute food and water. It was just a connectivity issue that nobody else was solving. 

So Levin coordinated with Steve Birnbaum, a satellite communications expert he works with, who had arrived on the island a week before the hurricane to prep for the storm’s aftermath. Their plan: to personally buy a bunch of small satellite terminals from Focused Mission, an emergency response business on the island. Levin then worked some local government contacts until he wrangled a helicopter. Among them was Puerto Rico’s chief information officer, Luis Arocho, who came along for a beta test to see if their plan would succeed. Soon this small team was airborne and installing terminals on two grocery store rooftops. They flipped the switches and boom — EBT purchases now worked. Levin would go on to install 12 more.

The experience was validating. “If the economy is broken in a place, the location can’t heal,” Levin says. But now, functioning EBT machines can lead to more products sold, more employees paid and more shelves restocked — an economic system revived, and saved from further dependence on FEMA aid. He says the hard costs totaled $33,000, which was ultimately reimbursed by the Foundation for Puerto Rico, and that around $3 million in transactions have since passed through the satellite terminals.

But it was legitimizing on a far larger level as well. Levin isn’t here in Puerto Rico simply to do one-off projects like this. He’s here to advance a concept — an audacious idea that he calls “expeditionary entrepreneurship.” In essence, it’s disaster relief in the form of entrepreneurship. Governments and NGOs are important, he says, with their standard operating procedures and approaches to administering aid. But entrepreneurship — not profiteering, but the principles of entrepreneurship — can accomplish what those bodies cannot: quick and nimble responses to ground-level problems, and connective tissue between foreign aid resources and capable local actors like grocery store merchants who are often not engaged. The same instincts that help an entrepreneur build a business, in other words, can help them rebuild a region from catastrophe.

Levin explains this to me as we drive past toppled power lines and landslide debris in Puerto Rico’s lush interior mountains. It is mid-January, four months after the storm has passed. “An entrepreneur looks at systems and comes up with creative fixes,” he says. “We start from the bottom up.”

Image Credit: Andy Isaacson

Levin didn’t just dream up “expeditionary entrepreneurship” one day. Instead, he came to it after pursuing two parallel paths: He was an adventurer, and an entrepreneur.

Related: 5 Ways to Prepare Your Business for Natural Disasters, Catastrophes and Income Loss

He’s always had an entrepreneur’s sensibility — that ability to sniff out an opportunity and boldly claim it. As a middle schooler in Connecticut, he launched a guerrilla marketing company called Jesse Levin’s Adrenaline Marketing. (Slogan: “With all due respect, you need a kid.”) He talked the beverage company SoBe into paying him $15,000 and helped promote them at extreme sports events by dyeing his, his friends’ and even his dog’s hair the brand’s hue of green. 

During summers, meanwhile, he also attended wilderness survival classes, learning how to build shelters and track animals through the woods. He became captivated by the power of resourcefulness — how solutions exist all around us. “Survival school informed every facet of my life,” Levin says. “My relationships, how I see things, how I conduct my business.”

After graduating from Babson College in 2007, those two passions continued apace. He moved to Panama, got into real estate, eventually bought a farm, and then launched a consulting firm. A Dutch company hired him to do project management and cultural mediation work in a remote coastal area where it had acquired land. The area — a haven for narcotraffickers and local mafia — was prone to flooding, and Levin inadvertently became the go-between for the special maritime police and the Red Cross to deliver medical care and supplies to his local community. The experience got him interested in disaster relief, so he followed the typical path: He volunteered. Following the historic earthquake in Haiti in 2010, he joined the NGO Hope for Haiti and spent six months crawling around the rubble. After the 2013 typhoon in the Philippines, he split his time between Manila and a town named Tacloban, where he worked alongside Team Rubicon, a relief organization made up of veterans.

Amid these overseas excursions, he was also pursuing traditional entrepreneurship. He became co-founder of Brooklyn Boulders, a New York climbing gym that was expanding into new cities. The first location was just outside Boston, and Levin’s goal was to draw people to the space. He realized that the same principles he’d learned in Haiti and the Philippines — drop in with no agenda, assemble a capable operational team and work closely with locals to find culturally relevant solutions — could work here as well. “We found the bike builders, the finger painters, the VCs and the nonprofits, and as we built, we said, ‘Here’s our philosophy: How can you leverage this space to amplify what’s going on here locally?’ ” Soon the place became a hybrid gym/community center/co-working space, hosting drone races, TEDx events and nude drawing classes, with MIT engineering students mingling with graffiti artists. Levin would replicate the concept in Chicago, and sell most of his stake in 2016.

Throughout this period, starting in 2010, he also launched and ran a company called Tactivate, which pitches itself as a project manager inspired by the strategies and tenets of Special Operations. Through his disaster work, Levin had befriended many Air Force pararescuemen and Army Ranger types. He found them to be inherently entrepreneurial, but their resourcefulness, wide-ranging capabilities and “operational mentality” often went unappreciated in the civilian world. Tactivate could bridge that divide, he reasoned, by combining military veterans with what its website describes as “installation artists, hospitality gurus, bootstrap entrepreneurs, branders” and more, for whatever project needs doing. 

That’s turned out to include running events, art installations and a “pop-up outdoor survival training bar” in Miami. His parallel life pursuits had begun to bleed together, each informing the other. In entrepreneurship, he was channeling disaster relief — the idea of moving quickly, identifying needs and bringing people together. In disaster relief, he’d been applying entrepreneurship — dropping into post-disaster environments and creatively supporting local capacity.

Along the way, Levin had assembled a vast Rolodex of relief operatives, from medics, communications specialists and private pilots to people involved in emergency logistics and air freight transport. “We all just kind of team up and see how we can fix things,” he says. “We’re fixers.” By last year, he’d come up with the phrase “expeditionary entrepreneurship” as a way to formalize his approach to disaster relief. Now he wouldn’t just be freelancing his way through regions; he’d be enacting a named strategy, which he could communicate to others. 

On September 20, this new phrase had its first test case: Hurricane Maria hit.

Image Credit: Andy Isaacson

“Cómo estás, señor!” Levin says, as he bro-hugs the guard at the security desk.

“Todo bien, caballero,” replies the guard chummily.

We’re breezing into La Fortaleza, the bright-blue governor’s palace in San Juan’s colonial quarter, as if Levin didn’t just land in Puerto Rico for the first time three months earlier. We head across the lobby’s marble floor and up the stairs to the corner office of PRITS, or the Puerto Rican Innovation and Technology Services. It’s a newly formed unit headed by two former executives — Luis Arocho, the island’s chief information officer, and Glorimar Ripoll, its chief innovation officer — and tasked with introducing data science and technology into Puerto Rico’s bloated bureaucracy. It’s also become something of a home base for Levin, a place receptive to his particular brand of entrepreneurship. 

As we approach, we find the office in a flurry of redecoration. A black love seat, armchairs and gold side tables form a new reception area by the door. We stand and watch long slab tables crafted from trees felled by Maria — and a large wooden PRITS sign emblazoned with the Puerto Rican flag — being hoisted into an open window by a cherry picker. A giant, flashy canvas donated by a famed local artist, painted with the words La Gran Fiesta, is carried in and then promptly taken away: too much. Levin smiles. 

In his vision, everything is scalable — every relationship, every idea. You start with one thing and build off it. It’s not always easy to draw a straight line from one to the next, but what’s happening in this office, at least, offers a useful pathway of how Levin’s philosophy unfolds.

Related: 5 Steps for Managing Disaster Recovery for Your Business

It started with that project to install satellite terminals. Originally, Levin had asked Arocho, the chief information officer, for help. “I thought, This is great, but knowing government, it probably won’t happen as fast as we need it,” Arocho recalls. It had taken six weeks to request and launch Google’s balloon-powered Project Loon internet service on the island. But when Levin and his team produced  the technology in less than a week, Arocho was impressed. “At that moment, I knew these guys were for real,” he says. “They’re forward thinkers. They offer a different approach — that entrepreneurial mindset — to dealing with government problems.”

Now Levin had a useful new relationship. Arocho became willing to provide, as he calls it, “top cover” for his efforts — signing forms when necessary, opening doors. And meanwhile, Levin was repeating this process with other key players around Puerto Rico. He’d befriended the heads of the Foundation for Puerto Rico, as well as key officials from FEMA, the military and the Department of Homeland Security. Leveraging his network, Levin often just connected dots. A cutting-edge, solar-powered water-purification system was installed at a Boys & Girls Club in the town of Loíza because of an introduction Levin made between MIT’s Lincoln Laboratory and the Roddenberry Foundation. He introduced Global DIRT, a disaster response team, to a local organization in St. John requiring assistance, leading to a major response and connectivity operation benefiting the U.S. Virgin Islands. “This connection was immensely valuable,” Devin Welch, a solar-power-business owner, told me. 

Direct relationships and one-off operations can only scale so much, Levin knew. What he needed was to re-create what he had with Brooklyn Boulders — that gathering point where infinite other relationships could thrive and people could find new ways of helping the island. “Whether in business or disaster response, informal relationships are how everything gets done,” he says. So, not long after arriving in Puerto Rico, Levin took over a six-bedroom house near the beach in San Juan that he found on Airbnb. At $275 per night, it came with a bar and an outdoor pool yet cost the same as a room at the nearby Hyatt. Then he invited everyone he’d met for regular Thursday happy hours (but also almost any time), offering a retreat where exhausted relief workers could decompress over cheese, crackers and bottles of Medalla Light, and even crash in a bedroom if necessary. Here, he believed, the silos of NGOs and government and military could break down. 

Arocho became a regular. So did senior officials from the U.S. military and FEMA, Puerto Rican bureaucrats and businesspeople and private-­sector technology specialists. Smart, young Puerto Rican doers arrived and began working out collaborations with PRITS. A filmmaker hired by AARP showed up and found people to help her document Maria’s impact on the elderly. Members of relief organizations swapped insights, and found partners for their work ahead. “We were better prepared for what was to come during our time there by hearing real stories of what was occurring and needed,” says Tamara Robertson of Engineers Without Borders.

The house created new relationships, but it also continued to strengthen Levin’s existing ones. And that’s how, last January, Levin came to suggest that Arocho redesign the government office. If PRITS is to be an emblem of collaboration and make Puerto Rico attractive to innovators, he argued, the space ought to look the part. Arocho agreed; the office was originally nothing more than a drab, government-issue space. So Levin found a sponsor to put up $15,000, linked in a California-based furniture designer named Marcus Kirkwood and enlisted Levin’s twin sister, Sefra Alexandra, who had also come to Puerto Rico after the hurricane and built seed banks in 26 schools across the island. 

Now, on this day in January, we’re watching the fruits of collaboration and relationships. The new tables are being arranged. Sefra is decorating the room with tropical plants. Arocho stands by Levin and looks on happily, snapping pictures. 

Image Credit: Andy Isaacson

Much of the attention on Puerto Rico’s hurricane response has focused on government’s colossal failures: FEMA’s sluggish response. The island’s struggle to get a handle on the situation. Corrupt utilities and local mayors. Mismanagement and dysfunction. Wastewater systems and an electrical grid left vulnerable after years of neglect. 

But there’s another story: how Puerto Rico’s citizens took care of themselves. Neighbors banded together. They shared food, fuel and shelters, driving their own hyperlocal response efforts. Levin talks about Alberto Delacruz, a Coca-Cola distributor he met who mustered 2,000 generators, loaded them on his fleet of trucks and delivered them to stores, clinics, salons and restaurants across the island. “Yes, he wanted his clients back in business,” Levin says. “But he solved a problem.” Necessity also inspired D.I.Y. solutions. I heard about residents powering homespun washing machines with battery-operated drills that they charged with solar panels; about electrifying their homes with car batteries. Local businesspeople began talking of themselves not just as merchants or salespeople but as sources of solutions — as linchpins of their communities.

This is, it turns out, a regular though less reported part of the disaster-recovery cycle. “History has shown that the disruption of existing traditions, policies and structures can create a climate of innovation and entrepreneurship,” reports a 2017 study in the International Journal of Entrepreneurial Behavior & Research. The research was put together by two DePaul University professors who surveyed decades of reports on how entrepreneurship rises in areas that fall victim to disaster. Their conclusions: Perceptions of entrepreneurship always improve as local people, with their deep knowledge of their community’s needs, become effective in ways that large institutions like government can’t. And local entrepreneurs themselves go through a transformation, shedding anxieties that might have held them back before. “Necessities of the individual and his community override increases in fear of failure,” the DePaul writers report. From this, new solutions are created and new businesses are born.

(This phenomenon extends to Levin himself: The co-directors of the University of Delaware’s Disaster Research Center tell me that, after disasters, independent people often step in to do what he does — help forge connections. They just don’t typically think of themselves as entrepreneurs.)

Related: Volunteer to Help Those in Need – and Become a Better Entrepreneur

However, something is happening in Puerto Rico that the DePaul writers hadn’t chronicled elsewhere. Entrepreneurs from outside Puerto Rico are arriving with vigor. Within days of the storm, scores of technology companies in particular have made landfall, ranging from large entities like NetHope and Tesla, which is launching new battery projects on the island, to smaller makers of passive water collection and purification systems and “mobile ad hoc” wi-fi networks. Many see the island as a test bed for their new technologies. Wealthy cryptocurrency entrepreneurs have arrived en masse, eyeing Puerto Rico’s generous tax incentives, broken systems and humbled government as an exciting set of challenges. “It’s turned out to be this really amazing opportunity to put to work block-chain technology,” Reeve Collins, cofounder of the company BlockV, told me.

Levin watched this happen on the island, and two months after the hurricane, he felt it was time to move on to a new phase of his expeditionary entrepreneurship project — away from disaster relief, and toward disaster preparedness. (Hurricane season begins in June.) He’d now play superconnector for this new community on the island, locals and newcomers alike, whose products and services could help Puerto Rico in the long run. 

By this point, Levin had stopped renting his communal Airbnb; the aid workers who frequented the house had largely left. Now he makes connections on the fly. “I go into an area and try to identify who’s who. And I try to empower them and connect them around a goal,” he says. Over the course of my three days with him in January, this is almost entirely what I witness Levin doing. He meets with property developers and investors and lawyers and local foundations and youth activists and surfers and (of course) cryptocurrency entrepreneurs. We stopped in at a tech accelerator one morning to meet re:3D, a startup experimenting with an industrial 3-D printer to fabricate storm-­ravaged stuff like furniture and coral. We had lunch with Milton Soto, an influential bartender who is rehabilitating an elementary school after the hurricane, before stopping by Aqui Se Puede, a watering hole whose owner and resident carpenter once worked for Andy Warhol. For Levin, these encounters are mostly soft touches — rapport building, part of his overarching effort to piece together a network of “local capacity” in the event of another disaster. 

One morning, I join Levin for a 7:45 a.m. workout on the beach with Carlos Guardiola, a well-connected Puerto Rican entrepreneur who owns one of the island’s largest warehousing businesses as well as medical cannabis licenses; Rafael Ortiz, who is in private equity; and Ben Manning, a former Navy SEAL fresh out of eight years in the service, whom Levin had taken on as something of an apprentice. (Each night before bed, Levin and Manning “debriefed” about the day’s meetings and exchanged the lessons learned.)

After burpees and sprints, we sit down for breakfast at a beachfront inn.

Guardiola describes his role as an unofficial connector. “I have a very simple rule: I don’t do business with anybody unless I eat with them seven times,” he tells Levin. “I like to see how you treat the waiter. I like to see who you know around. I like to see how you react. Because everybody’s a great first date.” Since 1996, he’s frequently hosted invite-only salons that bring together venture capitalists, housewives, street artists — an intentionally diverse mix — and after the hurricane, that made him a natural contact point for many people on the island. Not unlike Levin, Guardiola began making connections that helped the disaster recovery along. In one case, he connected GivePower, a major clean-energy nonprofit, to local partners to install water desalination and purification systems.

“And that’s how real recovery happens,” Levin says. “It’s understanding the landscape, and making very unconventional, strategic relationships of human capital, and understanding the capacity of respective operating groups, and putting them together.”

“It basically comes down to what we’re doing here — it’s breaking bread,” Guardiola replies. “I’m not in the business of employing people, because I think that’s what kills Puerto Rico. That whole mindset of I want to get my sure thing. There is no such thing as a sure thing! And that’s why this is really the perfect storm. You know everybody was thinking, Oh, the United States, they got our back. Bullshit! Oh, we’re going to get money from FEMA. Bullshit!” 

If Puerto Rico has a savior, they agree, it will be the entrepreneurs on the island — both the ones born here and the ones flocking in. This is the lesson they took from Hurricane Maria. “Once you realize that no one is here to save you,” Guardiola continues, “that is the most empowering thing, or the most frightening thing. And whoever is frightened should get on a plane and go to Orlando. Get the fuck out of the way.”

Image Credit: Andy Isaacson

One day, before a meeting with a lawyer from a prominent Puerto Rican real estate family, Levin takes me to the ruins of the former Naval Reserve Officers Beach Club. It’s perched over the sea, above a popular surf spot and in the shadow of an old Spanish fort, but it’s an absolute mess: small buildings stripped down to the concrete and covered in graffiti, hunks of wood scattered like discarded toys. The site belongs to the city of San Juan, but he’s actively courting the city government and pitching investors to turn it over to him. 

Related: 8 Ways to Use Emotional Intelligence and Make Lasting Connections

Here, Levin says, is where he can have a truly lasting impact.

“I’m proud of our ability to drop in and be operational, but really, at the end of the day I’m just another guy going out and fixing a radio, or clearing search and rescue,” he says. 

That’s why he wants this permanent space — a place to once more repeat what he learned at Brooklyn Boulders. When he’d bring the climbing gym to a new city, Levin would start by inviting a diverse group of locals — from investors to artists — into the space as they were building it. He called the gatherings “hard hat dinners,” and the goal was to get influential constituencies in the community to meet each other and have a say in what became of the space. That way, when it opened, they’d already feel like it was theirs. 

This is what’s missing in Puerto Rico right now, he believes. The worst has passed. Electricity is slowly returning. But what about the next Maria? All of this entrepreneurial energy — the resurgent locals and the innovators coming with their cutting-edge resiliency technologies — needs a central place to organize around disaster preparedness and recovery. The way Levin envisions it, this could become an open-air market: a hybrid pop-up space where military veterans teach preparedness skills to patrons amid food trucks, live entertainment and off-grid-technology exhibits. He’d been involved in a project like that in Miami — minus the disaster element, of course — and thinks it can work here, too.

Recently, Levin signed a one-year lease on an apartment in San Juan. He’s racked up a hefty credit card bill during his time here, but he’s determined to bring his new concept to life and recoup his costs in the process. “Puerto Rico is a phenomenal place to demonstrate this concept of community self-sufficiency,” he says. And if it’s successful, he wants to replicate the idea back in the continental U.S. — and prepare us all for whatever is to come.