Landing at the airport on the tiny West African island of Príncipe, the plane seems to skim the top of the dense jungle canopy, almost like a pebble skipping the surface of the water. Runway and shack-like terminal aside, there’s barely any evidence of human intrusion into the Jurassic Park–like landscape. Later, as you roam through that jungle on foot, the sensation of time warping is only magnified. The strange caws and yelps that ricochet round the canopy, evidence of the dozens of unique bird species here, could just as easily be a dinosaur’s, out of place and time.

It’s an impression that also hit Mark Shuttleworth when he first touched down here in his Bombardier jet over a decade ago, casting around with his pilot for a handy pit stop between his two permanent bases, the Isle of Man in the Irish Sea and Cape Town, South Africa, where he grew up. “I was looking for an out-of-the-way place where I could essentially just enjoy being at ease with nature in Africa,” he recalls. Though he admits, “I was almost going to write this off,” his mind changed, quickly, after disembarking on Príncipe. “My overwhelming impression was that this was both extraordinary and extraordinarily fragile. And I wanted to take the opportunity to do something with the people there that gives them something unique in the world, forever.”

That impromptu mission—he even showed up at the president’s office unannounced, without an introduction, seeking a meeting—has become a driving force in Shuttleworth’s life and turned the country of São Tomé e Príncipe into one of his primary passions. The 48-year-old South African–born multimillionaire has plowed more than $138 million of his fortune into Africa’s second-smallest nation by area (after the Seychelles), aiming to shore up its economy and thereby help prevent uncontrolled exploitation of its chief resource: nature. His plan is to lure wealthy, eco-conscious travellers here, mimicking the high-spending, low-footprint tourism strategy proven successful in Rwanda and Botswana, for two examples.

São Tomé e Príncipe investor Mark Shuttleworth. Maique Madeira

Ten years in, concrete results are now becoming apparent, with three hotels up and running and another on track to reopen by year’s end. HBD Príncipe Group, the company he created for the project, prioritizes the social good, but its chief executive, Malcolm Couch, expects to break even in two to three years and begin generating a profit within a decade. Couch says HBD will reinvest any earnings in the island’s economy.

“We’d want to say to other folks who may have wealth that they wish to do something with, perhaps in other parts of the world, that you could use this model. We’ll show you how to do it.”

Shuttleworth has an estimated fortune of approx. $920 million, accrued mostly through tech start-ups. He’s famous for splurging $28 million of it to go into space 20 years ago as a paid passenger on a Russian Soyuz craft, the first person from his continent to do so, earning him the nickname the Afronaut. It’s a misleading headline-grabber, as Shuttleworth is no playboy prone to frittering away his money on gimmicks. Think of him rather as the antithesis of countryman Elon Musk. He wants to deploy his enormous wealth during his lifetime and in productive ways that emphasize social—rather than social-media—impact. At the same time as he was prepping for space, he established the Mark Shuttleworth Foundation, which provides small grants to Shuttleworth Fellows, who pursue humanitarian and environmental projects around the world, including, but not limited to, in São Tomé e Príncipe. One recent grantee is working on tagging turtles here, to monitor their laying habits.

Such social engineering, and patrician largesse, can reek of neo-colonialism—a charge that Shuttleworth doesn’t dismiss. He understands the complexity and optics of a wealthy, white African funneling his fortune into a poor, majority-Black nation in the 21st century. “I think there is a profound difference between national dominance and investment, but they can sometimes get intertwined,” he tells Robb Report in a rare interview. “I have no real interest in extracting anything from Príncipe or exploiting it. It would be crass to think in those terms.” Shuttleworth presents his intentions as altruistic: “Príncipe is a once-in-a-lifetime opportunity to steer development in a different direction.”

Fishermen bringing their daily catch to shore. Elsa Young

Shuttleworth believes he is not alone. “I see other very successful, privileged people almost universally have a desire to do something good with their gains in life,” the reclusive Shuttleworth says. “But it’s difficult if you try to do that in your 80s, because you end up with a very limited set of options. I wanted to use the energy and perspective I could bring to bear as a younger person.” And unlike many of his peers, he sees no need to bequeath his wealth; Shuttleworth is resolved to never becoming a parent. “I had the snip in my early 30s to make damn sure, because I came to the view you couldn’t be a great parent and really great at difficult things,” he offers, unprompted. “The fact is that the evidence shows you’re going to be happier, have a better quality of life and a vastly decreased carbon footprint if you don’t have children. I wish we celebrated and talked about that more.”

The missions that appeal most to him are signaled by the HBD name: The acronym stands for Here Be Dragons, an old cartographer’s shorthand for terra incognita. It’s a nod to pushing boundaries and also suggests why he’d champion a place like São Tomé e Príncipe. The tiny, twin-island nation is barely 1000 square kilometres in total landmass and is volcanic in origin. There were no permanent inhabitants when Portuguese explorers chanced upon the lush, rocky land in the Gulf of Guinea in the late 15th century. They encountered true virgin territory, where almost every inch was heavily forested; the colonials commandeered the land to repurpose as plantations. Initially, they produced sugarcane, but that crop was elbowed aside on the order of the Portuguese king around 1820; deploy the fertile soil, he decreed, on the new, lucrative crop of cacao. The tree had been co-opted by Europeans after they stumbled on it in Brazil, and the chocolate produced by its cocoa beans became a global obsession—so profitable for the Portuguese-speaking world that cacao remains slang for money. By the mid-19th century, what’s now São Tomé e Príncipe was one of the world’s foremost cacao producers. For labour, the industry initially relied on enslaved people, and then indentured workers after slavery was outlawed in Portugal’s colonies in the mid-1870s. Many of those laborers were imported from other Portuguese fiefdoms, notably the Cape Verde islands. They lived on vast roças, estates that functioned more like miniature countries than companies; each typically had its own hospital, food supply and railway.

A restored colonial-era building overlooking Ana Chaves Bay on the coast of São Tomé. Elsa Young/Frank Features

In the early 20th century, the cacao industry here came under fierce critique from the British, whose best-known chocolatiers were Quakers, longtime abolitionists who viewed the indentured labourers as enslaved peoples in all but name. Rowntree, Cadbury and Fry eventually succeeded in implementing boycotts of the islands’ crop. (It may not have been coincidental that cacao producers from nearby modern-day Ghana—then a British holding known as the Gold Coast colony—were competing for the same market.) The snub, along with the islands’ struggle for independence, which was won in 1975, and post-colonial hardships, proved almost lethal to São Tomé e Príncipe’s main industry, and many of the roças fell into disrepair. Since then, some have been rebooted, and cacao remains synonymous with the country. Comprising a majority of the nation’s exports, the produce is touted as among the world’s best and is used by countless luxury chocolatiers. But São Tomé e Príncipe has another asset that Shuttleworth believes could be even more valuable: the land itself.

The larger, dominant island, São Tomé, is more populous, with almost 97 per cent of the country’s just over 200,000 residents. It has plenty of ramshackle charm and a relaxed affect summed up in the local maxim léve-léve, or easy-easy. Water sloshes around the rocks at the Boca do Inferno, or Hell’s Mouth, on its east coast, shooting up in unpredictable spouts; the beach nearby is a fine surfing spot thanks to those same waves. Piglets often scamper down the roads; one resident jokes that owners push them into the street, as the local custom compels any driver who hits a pig to both hand the carcass back and pay appropriate compensation. The capital, namesake city has a faded glamour, its beachfront rimmed by a colonial-era promenade with missing chunks like a gap-toothed smile. In the center, Claudio Corallo, the country’s best contemporary chocolatier, makes his products, which have been sold at high-end shops around the world, including London’s Fortnum & Mason. In Africa for almost five decades, the 70-year-old expat Florentine leads taste-and-tell classes at the factory he built from two shipping containers in his backyard. The raw material on which he relies is cacao from his farm on Príncipe.

The Príncipe kingfisher, one of many species unique to the island. Elsa Young/Frank Features

And it’s Príncipe that is the real draw for most visitors, as Shuttleworth quickly realized on his first trip; today, with the exception of the Omali hotel on São Tomé, most of HBD’s in-country operations are focused here. The smaller island, around 50 square miles, is a UN biosphere. It’s home to dozens of creatures indigenous only to this country, leading it to jostle with the much larger and better-known Madagascar for rights to the lazy but useful sobriquet “Africa’s Galapagos.” This richness of unique fauna is a legacy of the land’s volcanic origin: The island’s never having been connected to the continent proper allowed species to evolve without its influence. Praia Grande, one of Príncipe’s largest beaches, is prime turtle-nesting territory. Leatherbacks and green sea turtles scuttle along the sands starting in late fall to lay their ping-pong-ball-sized eggs under the watchful protection of a local nonprofit. By February, hatching season has begun, and for three months or so, the sands teem with tiny turtles as they exit their nests and make straight for the choppy seas.

In the colonial era, both islands held plantations. On São Tomé, many remain in some form, quarters for enslaved people often still used as housing. On Príncipe, though, the jungle has reclaimed most of the grander roças, with nearly 60 percent of the island’s landmass reserved as a national park. The best way to see it is by sailing through the Baía das Agulhas, or Bay of Spires—on a fine day, the skyscraper-like igneous-rock towers are free of mists, spiking above the canopy into the sky. Hike through the undergrowth on foot, and it’s easy to discover a man-made detail—a brick bridge, perhaps, or some old railroad tracks—that seems out of place in the wild forests, like an outtake from the finale of Planet of the Apes.

The O Quê Pipi Waterfall on Príncipe. Scott Ramsay

If you want to stay on Príncipe, HBD now owns and operates three hotels here, each anchored in the landscape in a particular way. “Príncipe is incredibly safe, remote and everybody knows everybody—that’s sort of unique,” Shuttleworth says of the strategy behind his tourism operation. “It allows us to try some things we wouldn’t in other places.” Take Sundy Praia, a tented camp on the beach, which was built from scratch four years ago and is deliberately hidden from view so as not to impinge on the untouched landscape. It lacks barbed-wire border fences or any other evidence that the local community is unwelcome; indeed, one Sunday morning, a group of teenagers loll on one of its beaches. Each structure has been built to minimize its impact on the land and can be removed leaving virtually no trace. The air smells warm and slightly moist, and the only sound other than the birds is the waves. A gray-bearded lepidopterist, one of the hotel’s guests, appears occasionally from the undergrowth, net in hand, questing for specimens of the island’s unique butterflies; he has been coming to Príncipe for decades to combine vacation with a little fieldwork.

A 15-minute walk up the hill is Roça Sundy, a former plantation home that has been repurposed as a 16-room hotel. Close by sit the sanzalas, erstwhile quarters for enslaved people, which 150 or so families still occupy; many of the residents work on the cacao farming that HBD has undertaken on the property. The final holding is Bom Bom (Good Good), the island’s best-known hotel, which sits in an extraordinary setting, perched on a promontory wedged between two beaches that face east and west, respectively, ideal for sunrise and sunset both. The cabin-like rooms connect by a bridge to a tiny islet that’s home to the resort’s restaurant and bar. An avian-friendly garden, planted by Shuttleworth’s bird-watching mother, helps draw the island’s exotic species to flutter through the property.

The infinity pool at Sundy Praia, a five-star tented camp on Príncipe. Scott Ramsay

Robb Report has exclusively previewed the next phase of HBD’s efforts on Príncipe. Bom Bom, first built as a fishing lodge in the 1980s and currently shuttered, will receive guests again later this year, after an extensive renovation. “We’re celebrating those extraordinary beaches, that kind of Robinson Crusoe feeling of just you on a beach that no one has ever been to before,” Shuttleworth explains. “When you’re sailing past Bom Bom in the future, you won’t know it’s there.” Sundy Praia will get a new spa, as well as an alfresco gym, integrated into the forest. HBD has also bought a building in the island’s tiny capital, a 40-minute drive away, where it will create a new market, gallery, offices and restaurant, as well as a few guest rooms. And at Roça Sundy, the company plans a renovation of the sanzalas. Shuttleworth hopes they will be reborn as a marketplace for São Toméans to sell food or crafts; the families currently residing there will decamp to an HBD-constructed modern village nearby.

HBD has made significant efforts to ensure its building projects aren’t destructive, even inadvertently. Shuttleworth has worked to provide an economic uplift as a result of HBD’s presence—all but one of the 50-plus staff at Roça Sundy, for instance, are São Toméan. (As is still unfortunately common in the African hospitality industry, the general managers of all three properties are white.) Many of the employees live in the sanzalas, and guests can even dine there at a restaurant run by one of the women, who cooks up superb fresh-caught calamari and fish to serve at a long table wedged under the wooden awnings that jut out from the old concrete quarters. As for the environmental side, Emma Tuzinkiewicz arrived in March as HBD’s first on-site sustainability director, lured from an executive role at KKR & Co. in New York. HBD is also part of the Long Run, a nonprofit that brings together resorts and lodges in remote destinations around the world, from Kenya to Australia, collaborating to share sustainable practices.

A papaya and passion-fruit smoothie served at the property’s Oca Sundy restaurant. Elsa Young/Frank Features

“It’s very important that the people who are there now feel like they had a hand in shaping things,” Shuttleworth says, acknowledging that the new housing development he’s funding and into which the current sanzala residents will move, has a name that might seem patronizing, at best: Terra Promitida, or Promised Land. But the community chose it for themselves. “I was taken aback, as it’s a little awkwardly biblical for my taste. After I got over my eek, at the very least we know this community desperately wanted better [housing] and saw this as their best shot.”

Shuttleworth has actively engaged with São Toméans from the outset, seeking their counsel. “My first impression of [Shuttleworth], I confess, was suspicious. I thought, ‘Why would a young man, apparently in his 30s, be interested in investing in a lost island in the Atlantic?’ ” José Cassandra writes in an e-mail.

The 57-year-old was regional president of Príncipe island for 14 years, until August 2019, and worked closely with Shuttleworth as HBD’s interest in the country grew and their visions aligned. Cassandra notes approvingly of that resettlement project, as well as HBD’s approach to job creation, preserving the island’s natural resources even as unemployment levels were high.

Cassandra dismisses concerns of neo-colonialism outright, noting that locals already occupy several senior roles across HBD’s various enterprises. “We need investors who believe in the potential of our country, in various domains like agriculture and tourism, and will involve people and train them, as HBD has done,” he writes. “This will contribute to creating a national know-how to assume our own development projects. The opposite would be some kind of colonialism.”

Blue-and-white azulejos above the main altar in Sé Catedral de Nossa Senhora da Graça (Our Lady of Grace Cathedral) in São Tomé. Elsa Young/Frank Features

It’s heartening to hear, but Shuttleworth remains aware of the uneasy bargain into which Cassandra and his country entered. “I would say it’s sort of icky to see a place like Príncipe, so fragile, precious and beautiful, and do nothing,” Shuttleworth says. “One might easily look at it, and think, ‘This will soon be destroyed,’ and then walk away. Development tends to follow a tragic curve, with a tremendous destruction of culture and identity. Would the locals and that environment end up in a better place if I did nothing? That’s unanswerable.” He’s perhaps being modest: When he first took interest in the island, the Sundy plantation area had been earmarked for sale to Agripalma, an oil-palm business, which would have felled the rain forest to replant it with palms—an economic uplift, for sure, but an environmental catastrophe. Shuttleworth and his team petitioned the government that they could create jobs without destroying the jungle.

Shuttleworth’s efforts are certainly well placed in terms of the trends in African tourism, according to Deb Calmeyer of Roar Africa, the elite travel specialist. “There’s a new wave of places that are becoming reachable and just about luxurious enough without [a guest] needing to be a pioneer adventurer,” she says. “It’s sad that when Americans think of Africa, it equals safari—the coastlines are sometimes so dramatic, and you can have the feeling of living on the edge of the wilderness on African beaches. You’re not going to find overdone, heavy-traffic resorts like in the Caribbean. There’s a raw beauty.”

Diving to a sunken airplane at the bottom of Bom Bom Bay. Scott Ramsay

São Tomé e Príncipe remains one of the least-visited countries in the world—it logged only 33,000 visitors in 2018, before the pandemic slashed numbers. The count is destined to remain comparatively low, at least in part for logistical reasons: International flights are limited to connections to a few West African hubs, including Accra in Ghana, and the colonial holdover route to Lisbon. Private jets are a handier way to visit.

Which is how Shuttleworth continues to alight here three times a year for monthlong stays on his properties, enabling him to remain involved, firsthand, with HBD’s efforts. “After a week in Príncipe, I feel like I’ve deepened something about myself— somehow soothed and challenged at the same time,” he says. “Life passes us by no matter what, and we only get to wake up and go to sleep so many times, and this feels like something that’s profoundly important.”