Skift Power Rankings: Who’s Making the Biggest Bets in Travel

Airbnb co-founder and CEO Brian Chesky is clearly thinking about more than short-term rentals: “Why would Airbnb just offer homes? Why couldn’t we offer significantly more things? And that’s the future of this company,” Chesky said last fall at the 2024 Skift Global Forum.

In Chesky’s view, that could mean new business launches each year with the potential to do $1 billion a year in sales.

First up are the new Experiences and Services offerings, and it’s risky given the company’s track record. Airbnb’s tours and activities segment debuted as “Trips” in 2016, and was a key component of Airbnb’s vision to become a travel “superapp.” The product didn’t get traction and Airbnb temporarily halted accepting new applications for Experiences in 2023. The investment adds risk too. Airbnb is dedicating $200-$250 million in 2025 toward building and scaling it.

To Chesky, Experiences is central to Airbnb’s mission, and there is a personal angle, too. He has spoken about loneliness and how Experiences can foster human connection. This time around Airbnb is making it easier for operators to integrate their Experiences into Airbnb, and is using celebrities and athletes to create marketing buzz. One issue with Experiences in the past is that Airbnb targeted customers with a niche product. This time around, Airbnb is trying to appeal to a broader audience while trying to retain the tours’ signature Airbnb touch. That may be an intricate dance — one that investors will be following closely.

– Dennis Schaal

Risk Number 1: Going after Google, which everybody knows dominates search. Risk Number 2: Not having sponsored results, which was one of the innovations that made Google billions of dollars – and one of the best business models in history.

But Perplexity co-founder and CEO Aravind Srinivas saw the opening for an AI-driven answer engine focused on curiosity and knowledge. And to build trust, every result would have a citation, much like an academic paper, and answers wouldn’t have advertisers.

What about making money? That’s where travel – along with other services – comes in. The travel search and booking process is seamlessly integrated into its products through partnerships with Tripadvisor and Selfbook.

“I think the business model is more around the assistant,” Srinivas said in April on the podcast, Tetragrammaton with Rick Rubin. “After answering a question about ‘what do I do in Kauai’, it can help you plan some activities. And part of actually booking the hotel and the trips and car rental – all that’s time-consuming, that you would pay an AI to do that for you. And you pay a lot, maybe, if it’s actually done reliably.”

That experience is also part of Perplexity’s recently launched Comet browser, which Srinivas calls the company’s next big bet (“The perfect blend of AI, navigation, and agents,” he says.) Importantly, the user can do all their searching – and travel booking – in one place with no need to open new tabs.

—Lex Haris

United States Commerce Secretary Howard Lutnick is betting he can dismantle decades of tourism marketing and infrastructure — and the travel industry (along with the broader economy) will be just fine, thank you very much.

The longtime Wall Street executive — best known for turning Cantor Fitzgerald into a post-9/11 bond trading powerhouse and spinning off a multi-billion-dollar empire in BGC Partners — has brought that same profit-maximizing, no-hand-holding style to America’s travel economy.

So far, Brand USA, the destination marketing organization tasked with bringing international tourists to the U.S., has lost 80% of its federal budget. Several board members have been sacked. And that’s by design. Lutnick is betting destination marketing can still “work” with a fraction of the money. So if travelers still come, the program was bloated. If they don’t, the market will correct.

Visa fees are up. Entry policies are tighter. Tourism promotion is down. And Lutnick shows no signs of reversing course. His Commerce Department continues to crank out clean dashboards and export data, but the broader orientation towards potential U.S. visitors has fundamentally shifted. The Trump administration seems to be telling tourists who are offended by higher fees or a colder welcome, that someone else will fill the gap — or they won’t. Either way, Lutnick placed his bet. It’s risky and unsentimental. Yet Lutnick appears totally convinced the numbers will bear him out.

– Sarah Kopit

Blake Scholl is betting that air travel’s next leap will be flying twice as fast as today – and that his company will get there first. Based in Colorado, Boom is building a new generation of supersonic jets. It’s no easy task, with countless hurdles and critics aplenty, but Scholl and his team are holding the course.

“I think it’s the natural progression that technology and air travel should get faster and better,” Scholl told Skift earlier this year. Reflecting on the stagnation of true innovation in the sector, not least the demise of Concorde, he adds: “We lost our way, and it’s a great tragedy.”

Boom Supersonic hit a major milestone in January when its XB-1 model broke the sound barrier during a test flight at the Mojave Desert. Scholl hopes to start test-flying a full-sized version in 2027 and enter service around 2030.

Boom will build the planes in North Carolina while also designing the engines itself, breaking with the conventional practice of outsourcing power. As for the energy source, they’ll run on sustainable aviation fuel.

Boom is not short of skeptics, but it also has a long list of believers. Big-name brands including American, United, and Japan Airlines have collectively ordered 130 Overtures – the name of its new supersonic jet. The aircraft will hold up to 80 business-class seats, flying at roughly twice the speed of today’s planes. A New York to London trip would take less than four hours; Seattle-to-Tokyo under five.

Scholl says the technology for supersonic flight has improved significantly since the days of Concorde: “Look at what we’ve accomplished. People said a startup couldn’t build a supersonic jet, but we did. People said that it could never be done with a small team and a small budget. Yet it was.”

If Boom succeeds, the implications extend far beyond aviation. “We’re not smart enough to predict every effect,” Scholl said recently on the Skift Travel Podcast. “But one thing we can be sure of is it will mean more travel and more cultural connection.”

– Jay Shabat

When it comes to tourism in the United Arab Emirates, Dubai has always led. But that balance is slowly shifting. Both Abu Dhabi and the once-quiet northern emirate of Ras Al Khaimah are now aggressively staking claims as global travel hubs.

Under the leadership of His Highness Sheikh Mohamed bin Zayed Al Nahyan, president of the UAE and ruler of Abu Dhabi, the capital has seen major tourism wins. In just a few years, it has secured the rights to a new Disneyland and a Sphere venue — two megaprojects poised to draw millions of visitors. Not only does Al Nahyan’s emirate have the right to build a Sphere, Sphere Entertainment granted Abu Dhabi exclusive rights to develop all future Sphere venues in the Middle East and North Africa.

Further north, Ras Al Khaimah is undergoing its own transformation. His Highness Sheikh Saud bin Saqr Al Qasimi has positioned the emirate at the center of one of the Gulf’s boldest tourism experiments. The $5 billion Wynn Al Marjan Island resort will include the region’s first legal casino – a move that could redefine tourism in the UAE when it opens in early 2027.

Wynn Al Marjan Island’s president Max Tappeiner said in a keynote speech in May that “the royal family could not be more supportive” of the project. RAK’s ruling family oversees the emirate’s government, and that government is a part-owner of the Wynn project.

The impact extends beyond RAK. Abu Dhabi has established a federal gaming commission, and other projects are underway. MGM Resorts is developing a property in Dubai, and Wynn has trademarked the term “Arabian Strip,” hinting at further expansion.

– Josh Corder

September 16-18, 2025 – NEW YORK CITY

Mandarin Oriental had long stood for quiet luxury. Its fan logo, heritage properties, and service-first ethos made it one of the most respected names in hospitality. But Laurent Kleitman saw room to evolve after taking over in late 2023.

He’s launched a 10-year “accelerated growth strategy” to more than double the group’s footprint. In his first year, Mandarin Oriental opened 11 hotels. Today, it runs 44 properties and has over 30 hotels and resorts in development.

The company is also reinvesting in its roots, with multi-million-dollar restorations underway at its flagship properties in Bangkok and Hong Kong.

Since its 1963 debut in Hong Kong, Mandarin Oriental has built its brand on consistency, emotional connection, and highly personalized service. Expanding into unfamiliar markets with different cultural expectations and competitive dynamics raises the stakes. Kleitman’s challenge is to protect that DNA even as the group innovates with new digital channels.

This April, the group unveiled its first brand refresh in nearly four decades with its first-ever mobile app and a new loyalty program. The aim was to make Mandarin Oriental relevant to a new generation of global luxury travelers.

“What truly sustains a luxury brand,” Kleitman says, is “the power of emotional connection, the art of storytelling, and an uncompromising commitment to excellence wherever and however you connect with the brand.” He adds: “Understanding our brand’s heritage and trajectory is essential to knowing where continuity matters and where change can unlock potential.”

– Luke Martin

TravelPerk founder and CEO Avi Meir isn’t afraid of risk: “Whenever I make these big life decisions, I sometimes try to build an Excel, provide weighted average criteria, and be very scientific about it…and then I end up following my gut feeling,” he told the Early Days podcast in 2022. “I literally have nothing that you don’t – except my willingness to take risk based on my gut feeling.”

In fact, there is a lot more of a plan and framework than those comments let on, but there’s no question that TravelPerk makes big bets. Meir and his co-founders started the Barcelona-based company in 2015 and saw an opportunity in booking and managing travel for small- and medium-sized businesses. Strong growth has followed: TravelPerk has had several fund raises to develop the product and make a series of acquisitions to expand its reach and offering.

Last year, it acquired Chicago-based AmTrav, which added 1,000 businesses as clients and doubled TravelPerk’s revenue in the U.S. This past January, it acquired Yokoy, which adds expense management to the offering – a big step. “It’s very innovative for our segment,” says president and chief operating officer Jean-Christophe Taunay-Bucalo, who joined in 2017.

TravelPerk said it has exceeded $2.5 billion in bookings annually and has grown revenue over 50% each of the last two years to over $200 million. It raised $200 million in January, bringing the company’s valuation to $2.7 billion.

According to Taunay-Bucalo, the key to the bets is keeping a focus on the user and on the long term.

“We want to be able to make investments for five years, for 10 years, for 20 years,” he says. “We like to have a big money chest so that we can think long term. So that we are not geared toward the next milestone, because the danger of always kind of cutting to the limit before your next round of funding is you’re optimizing for the very, very, very, short term and that can get you to the things that are not user focused.”

– Lex Haris

While most hotel chains keep operations as light as possible, Sharan Pasricha’s Ennismore is playing a very different game: Everything from restaurant concepts and interior design to digital storytelling is kept in-house. No outsourcing. That way, Ennismore is able to control the quality, and ensure that the guest experience remains authentic to the brand’s DNA.

According to Pascricha, lifestyle hotels are “experiences in their own right.” The focus, he says, is on creative storytelling through everything a guest sees and touches.

Pasricha started Ennismore in 2011 with a fresh idea: “to create hotels with soul, places that felt part of their neighborhoods, where people could gather, work, eat, celebrate, and feel connected,” he tells Skift.

His fascination with understanding how spaces can bring people together led Ennismore to acquire The Hoxton, Shoreditch. The company now has more than 180 operational hotels. With a pipeline of more than 140 hotels across the Middle East, Asia Pacific, and the Americas, Ennismore includes brands like SLS, Mama Shelter, and Delano.

Even a major joint venture with hotel giant Accor in 2021 didn’t dilute the brand’s essence. “They brought the infrastructure and scale, we kept the entrepreneurial spirit and creative control,” Pasricha says. Now, Ennismore is considering an IPO in the U.S.

He thinks of his leadership style as that of a curator. “My role is to bring together people who are way smarter than me…and give them the freedom and tools to do their best work.”

-Bulbul Dhawan

Starting out as a college dropout who taught himself to code, Toby Xu joined Alipay in 2007. “In 2014, I proposed an initial version of the Alipay+ strategy, and today, after more than 10 years of fast testing, improvement and implementation, we have finally developed our vision of a global Alipay+ ecosystem with rich digital use cases,” Xu tells Skift.

When faced with the choice between upgrading a legacy system or building an entirely new global payments backbone from scratch, Xu chose the harder route. “This idea of ‘calculated risk’ continues to drive our innovation spirit at Ant International,” he says.

Now, as chief strategy officer at Ant International, Xu is doing something utterly challenging: turning your digital wallet into a full-blown travel companion. Alipay+ Voyager, the latest brainchild, is an AI-powered agent that can book your hotel, plan your trip, translate your menu, calculate your tax refund, and still leave you time to post selfies with a panda.

“We believe that e-wallets and super apps go beyond just payment, they represent a new digital ecosystem bridging lifestyle and commerce, all within one app,” he says.

Under Xu’s watch, Alipay+ has grown into a cross-border juggernaut, partnering with wallets across Asia and now pivoting into AI-driven travel without losing sight of its payments DNA. The biggest risk, Xu says? Not innovating.

-Peden Doma Bhutia

Shai Zelering didn’t plan his way into Brookfield Asset Management. In 2014, he was at Thayer Lodging Group, and Brookfield scooped up the firm as part of its first opportunistic real estate fund. Zelering took that break and ran with it, and now leads the company’s hospitality investments division, managing a $22 billion portfolio.

“Thayer was a pioneer in hotel private equity,” he tells Skift, noting turnarounds like the Diplomat in Florida and the Ritz-Carlton San Francisco. “But it was only at Brookfield that the opportunity to build something truly global and impactful came to life.”

Brookfield’s portfolio ranges from hostels in Europe to Leela Palaces in India and Atlantis in the Bahamas. Think luxury meets volume, with over 40,000 keys across hotels, lodges, extended stays, and 12 portfolio companies spread far beyond the U.S.

“One of the benefits that we have is that we are really a global firm,” Zelering said on a Skift podcast in August. Noting that the company has 30 offices around the world, he said, “That is really powerful because we can really play different games in different regions.”

Investing in the hotel sector requires mastering both real estate fundamentals and the operational intricacies of hospitality. “We need to balance risk and returns, and not confuse brains with bull markets.”

Brookfield is clear that it is open to anything when it comes to business expansion, except commoditized business. “That is the standard. It doesn’t have to be only high-end or low-end. It has to be differentiated.”

What sets Brookfield apart? Smart contrarian bets. “We invested in India before others focused on it as a market. We invested in economy extended stay hotels before the hype. And bought some great hotels during Covid,” he says. “We take swings, but we have rigorously vetted plans.”

-Bulbul Dhawan

Eric Resnick’s journey from a ski-loving Cornell graduate to the CEO of KSL Capital Partners blends his passion for sport, deep sector expertise, and a realistic attitude toward risk.

After a stint as a consultant at McKinsey, Resnick took a senior partner’s advice to “combine your vocation with your avocation.” He joined what would become Vail Resorts in 1996, then owned by Apollo, where he gained front-line experience in IPO prep and acquisitions.

As co-founder and CEO of KSL Capital Partners for nearly 25 years, Resnick now oversees $25 billion in travel and leisure assets. In 2025, KSL and a joint venture partner acquired Hyatt’s real estate portfolio in Playa Hotels & Resorts for $2 billion. His strategic focus has positioned KSL to benefit from trends like rising U.S. passport ownership and the popularity of all-inclusive resorts in Mexico and the Caribbean while carefully navigating the challenges of operating in high-cost markets.

Resnick emphasizes that the goal is not eliminating risk, but managing it with discipline and creating a margin of safety to deal with volatility and factors such as government regulation. His risk tolerance is tempered by systematic assessment and a collaborative approach — often partnering with major operators like Hyatt to combine KSL’s capital and industry insight with operational expertise.

– Dennis Schaal

In an industry dominated by the Big Four — American, Delta, United, and Southwest — Ben Minicucci thinks there is room for Alaska Airlines. “When I look at the entire U.S. domestic market, we’ve got scale, relevance, and loyalty,” Minicucci tells Skift.

Alaska has long been a domestic airline with roots in the Pacific Northwest. But under Minicucci’s leadership, the carrier is now setting its sights on becoming a global airline.

Less than a year after the federal government officially approved Alaska’s merger with Hawaiian Airlines, the Seattle-based carrier is already on track to launch routes to Tokyo, Seoul, Rome, London, and Iceland.

“Alaska is taking a really bold step to say ‘Look, we are a good, strong domestic airline; West Coast-based, but we fly to the rest of the country,’” Minicucci says. “And this step now puts us on the global map.”

And in an industry that has seen domestic demand slide, Alaska’s profitability, at times, has been comparable to that of heavyweights Delta and United. With its international launch, Alaska has plans to grow its presence in California, open premium lounges at its Seattle hub, and introduce new business class cabins.

His excitement for Alaska’s future is palpable: “I’ve been blessed. I love this company. I love the people. I love our values. I love what this company means to communities, customers, and employees. And so it’s why I’ve been here. And I will be here until the end of my career.”

– Meghna Maharishi

September 16-18, 2025 – NEW YORK CITY

As Albania’s Minister of Tourism and Environment, Mirela Kumbaro is making one of the boldest long-term plays in European travel: using more than €1 billion in public and private funds to transform the country’s airports, roads, ports, and heritage infrastructure, all with the goal of doubling international tourism by 2030.

But the real risk lies not just in the scale of the investment, but in doing it fast, without repeating the mistakes of overbuilt neighbors.

Her ambition reflects visionary thinking: turning Albania from an under-the-radar backpacker haven into a year-round Mediterranean contender, with a goal of weaving sustainability and culture into the very foundation. She has tied tourism growth to environmental preservation, merging the two ministries under one umbrella, and prioritized protected areas, like the new Vjosa Wild River National Park, to anchor a “green growth” narrative.

Kumbaro’s background as a Sorbonne-trained linguist and former Culture Minister gives her an edge in public communication and policy vision. She talks about tourism as a form of identity-building and often leans on symbolic gestures, like restoring heritage towns or setting limits on private beach access.

The risks are very real: critics have raised concerns about environmental overreach, especially near protected coastlines. But Kumbaro has stayed the course, betting that authenticity, infrastructure, and smart growth can coexist. “Elite tourists who stay longer and spend more,” she’s said, are the future, not just crowds.

If her plan works, Albania won’t just be a breakout destination, it could become a case study in how to scale tourism from the ground up, without losing what made it special in the first place.

– Darin Graham

Pieter Elbers is steering IndiGo on one of the boldest growth paths in recent aviation history. A longtime chief of KLM, he led the Dutch flag carrier to steady profits even as its sister airline Air France struggled. But KLM is one of the world’s oldest airlines, and has modest growth. IndiGo is a very different challenge.

When Elbers arrived in 2022, the Indian carrier was already dominant at home and growing at more than 20% a year – many times faster than the global average. It was also consistently profitable, a rarity in Indian aviation. His mandate: turn that domestic success into a global presence.

Under his watch, IndiGo has ordered widebody aircraft and launched its first long-haul routes to Europe. It has forged partnerships with carriers including Turkish Airlines, Delta, and Air France-KLM. At the same time, the airline is upgrading its products, introducing business-class seats, and rolling out a loyalty program.

IndiGo’s ambitions were on display this year when it hosted the International Air Transport Association’s annual meeting in Delhi. It was a symbolic statement of its growing stature and one that likely unsettled rival Air India.

But the job isn’t over. Elbers still must prove that his intercontinental expansion can be profitable. He has hundreds of new planes to deploy, but is up against some of the world’s strongest airlines – many of which are also hungry for India’s intercontinental traffic.

As he told the Skift India Forum earlier this year, financial discipline remains critical: “India is a cost-competitive, price-sensitive, and consumer value-conscious market. Maintaining cost leadership is important for us. Every step we take is keeping that in mind, because if we don’t, we would be out of business.”

– Jay Shabat

Andrew Crawley, president of Amex GBT, has built his career on calculated risks as he helped to transform the airline and business travel status quo. His willingness to tackle complex challenges was evident during British Airways’ post-9/11 restructuring, when he worked closely with a small team and CEO Rod Eddington on cost management and operational efficiency. In 2004, he spearheaded the integration of revenue management and sales functions – a move considered risky at the time but ultimately successful.

“Typically airlines did not put sales and revenue management in the same place,” Crawley says. “They liked the natural tension.” He calls the combination “relatively successful.”

After multiple executive roles at BA and then parent IAG, including chairman and CEO of IAG loyalty from 2017 to 2020, Crawley moved to Amex GBT in April 2020 — joining during the London lockdown as chief commercial officer. Travel revenue plummeted in his first month.

He played a significant role in the 2021 Egencia acquisition, and became Amex GBT president in January 2023. Cultural differences played out in the integration of product and technology-focused Egencia with more service-oriented Amex GBT, Crawley says, adding that Amex GBT is now a “software and service company.” Next up: the integration of CWT, a longtime competitor.

“I love every minute of my job,” Crawley says. “It’s got variety. There is enough change to keep anyone occupied, I get to play with technology, and see new entrepreneurial innovations at work and so much change going on. It’s a real thrill.”

– Dennis Schaal

As the CEO of Visit Greenland, Anne Nivíka Grødem is leading one of the most striking experiments in tourism today: welcoming global travelers without compromising local life, values, or landscapes.

Her boldest move? A new 10-year tourism strategy built not on increasing visitor numbers, but on slowing them down. “Rather than maximizing arrivals, we are prioritizing community involvement, season extension, and regenerative practices,” she tells Skift. The goal is to keep tourism sustainable, before it grows too fast.

Grødem, who previously served as Greenland’s Minister of Finance and Interior, brings a political acumen and a deep understanding of Greenlandic self-determination. That background shows in how she speaks about risk: “In Greenland, true courage is not building more – it’s building better, slower, and more meaningfully,” she says.

Grødem has resisted the temptation of fast gains. Instead, she’s betting on infrastructure, local ownership, and impact. That means letting some communities opt out entirely, and others grow only on their terms. “We are shifting from a demand-driven approach to one grounded in place-based values, cultural self-determination, and ecological stewardship,” she says.

If it works, Greenland could become a model for how to grow tourism with limits and power in the hands of locals. “I lead from a mindset of care,” Grødem says. That includes care for the land, for the people who live there, and for what she calls “the silence,” a uniquely Greenlandic resource worth protecting.

– Darin Graham

For Graham “Skroo” Turner, risk has always been part of the calculation. “Getting my hands dirty on an apple orchard at the age of six set a foundation for my understanding of small business,” he recalls. “When I was about seven, I nearly ran over my old man – so he said, it’s obviously time I learnt how to drive a tractor.”

This early mix of independence and consequence would shape Turner’s pragmatic, but never timid, approach.

A trained veterinarian, in the 1970s he ran bus tours in Europe – the humble seed for what ultimately became the Flight Centre Travel Group. Five decades later, the company operates both leisure and corporate divisions in seven major markets, with its FCM Travel brand spanning more than 100 countries.

Turner is candid about his attitude about risk-taking: “We’ve had some significant failures, but we’ve also had quite a few reasonably spectacular successes,” he tells Skift.

When Covid‑19 grounded global travel, Turner and his team slashed monthly costs from $227 million to $65 million, cutting staff from 21,000 to 6,500 almost overnight – a brutal reset that reinforced his focus on strong cashflow. Though willing to act boldly in crisis, Turner seldom rushes: organic growth is favored, and more recent deals – like the acquisition of British luxury specialist Scott Dunn – are carefully calibrated.

That balance of boldness and caution shows today as FCTG rebrands U.S. stalwart Liberty Travel, while also investing in new technologies to make the business more efficient. Turner believes AI will “give travel agents a significant tool,” but suggests the human touch won’t vanish altogether.

Still healthy and engaged, the 76-year-old shrugs off succession talk. Turner is in the office five days a week and remains what he’s always been – a grounded risk-taker. “If you’re not growing, you’re not going anywhere. Hopefully profit follows, but it doesn’t always.”

– Gordon Smith

Ritesh Agarwal’s American Dream is to turn Motel 6 and its quieter cousin, Studio 6, into sleek, franchise-friendly powerhouses. More than anything, it’s a bid to prove that what he has built with Oyo can scale in the world’s largest economy.

The $525 million deal instantly super-sized Oyo’s U.S. footprint, adding nearly 1,500 properties. Agarwal has said the plan is to add about 150 more properties this year.

The chain’s franchise network is established, and Oyo believes it can work with existing operators rather than replace them. Also, Oyo knows how to work with Indian-origin property owners (many of whom run Motel 6 franchises).

Agarwal’s playbook is predictable: find undervalued assets, add a layer of tech, and scale fast. Despite IPO delays, valuation markdowns, and regulatory dust-ups from Delhi to California, Agarwal’s appetite for expansion remains unshaken. And now, an IPO is back on the table, with a possible filing expected in November.

Agarwal has also eyed Europe. His acquisitions on the continent have included Paris-based Checkmyguest, Croatian and Danish vacation rentals. Also in the bag is Amsterdam’s @Leisure Group. Back home in India, Agarwal is focused on “premiumization,” hoping to turn spiritual getaways into boutique stays with smart check-in kiosks.

-Peden Doma Bhutia

There is no shortage of ways to book travel, but Jason Wynn never saw Chase Travel as just a way to facilitate transactions. Wynn joined JPMorgan Chase in 2021 to head up the new travel venture.

“The crazy thing about Chase Travel was, it was launched during the pandemic, which at the time was a bold move given what the prospect for the industry was,” says Wynn. “We trusted the signals we were seeing, we trusted the data, and we knew we had a unique opportunity.”

To build it, Wynn relied on acquisitions. CX Loyalty gave it the tech platform. Then came Frosch International Travel, with its core in corporate travel and which itself had acquired Valerie Wilson Travel, a luxury agency.

“Of course at the time there was a tremendous amount of risk of making the acquisitions and investments we did,” he recalls now.

But the idea was to be able to offer a wide range of services and tap into JPMorgan Chase’s full network beyond just card holders, including the private bank and wealth management. Chase Travel now offers premium hotels, cruises, and has six airport lounges.

“When we looked at the competitive space, obviously there was a lot going on, but most of the industry was fighting over the same battle ground: customer acquisition, SEO rankings, price comparisons, last click conversions. And fundamentally we’re playing a different game,” Wynn says.

The strategy has led to fast growth. Chase Travel lags behemoths like Expedia and Booking Holdings, but in just a few years, it’s up to $11 billion in sales with 4 million unique customers.

The next step is deepening the integration with JPMorgan Chase’s other lifestyle products. “If you zoom out, it’s more than just travel,” he says. “Our investments across travel, dining, shopping. The full lifestyle ecosystem is delivering this connected element. The job for us now is to keep connecting the dots.”

– Lex Haris

Vlad Doronin doesn’t place small bets. The 62-year-old chairman and CEO of Aman Group has transformed the ultra-luxury hotel brand Aman into a more than $3 billion hospitality empire. Now he’s planning his biggest gamble yet by trying to raise up to $2 billion to scale Aman’s footprint while also growing Janu, a millennial-friendly sister brand.

Luxury brands typically dilute as they scale, with ultra-luxury groups averaging only 25 properties. Aman had 26 resorts when Doronin took over. Now there are 36 Amans, with 8 more announced, and one Janu, with 11 more in the pipeline.

Doronin believes he can maintain exclusivity at scale. “We’ve seen unparalleled ADR [average daily rate] growth across the entire constellation of destinations over the last 10 years,” he says.

Doronin’s appetite for calculated risks traces to Russia’s post-Soviet boom, where he amassed his first fortune in real estate. After acquiring the struggling Switzerland-based Aman Group in 2014, he executed a turnaround.

One of Doronin’s wagers was to open Amans in major gateway cities, beginning with Tokyo and New York City. The brand had a reputation for offering hideaway experiences in rarely-visited destinations with spiritual connotations, such as Balinese villages. Critics questioned whether that would translate in urban hubs. Doronin says demand and repeat visits show the formula works.

Doronin saw that while Aman is about seclusion, younger travelers often crave social connection. So last year, he opened the first Janu, which has livelier bars and higher room counts.

What’s next? Doronin is expanding into branded residences (with over $5.7 billion already sold), interior design services, and membership clubs.

–Sean O’Neill

September 16-18, 2025 – NEW YORK CITY

Mark Hoplamazian has steered Hyatt decisively into the all-inclusive market, a notable shift for a company once best known for its city business hotels.

His latest move: The roughly $2.6 billion acquisition of Playa Hotels & Resorts. The deal handed Hyatt control of 15 resorts across Mexico and the Caribbean. (Hoplamazian quickly flipped the real estate for $2 billion.)

The Playa deal capped a four-year spree that transformed Hyatt into a heavyweight in sun-and-sand vacations. In 2021, Hoplamazian shocked the industry with a $2.7 billion acquisition of Apple Leisure Group, doubling Hyatt’s resort footprint. In late 2024, Hyatt struck a long-term joint venture with Spain’s Grupo Piñero, adding 22 resorts.

Hyatt now operates one of the largest all-inclusive portfolios in the world, spanning 11 brands and over 150 resorts. Few peers moved as early or aggressively. While some questioned whether he was over-indexing on leisure, Hoplamazian read the post-pandemic market correctly: Guests wanted fewer decisions, more value, and resorts that could do it all.

Simultaneously, he restructured Hyatt’s offerings into five brand portfolios — Luxury, Lifestyle, Inclusive, Classics, and Essentials — giving each a clearer focus and leadership. The 2024 acquisition of Standard International gave Hyatt more muscle in the lifestyle segment.

As of July, Hoplamazian is also serving as interim Chief Growth Officer. He sits on the executive committees of the American Hotel & Lodging Association and the World Travel & Tourism Council.

– Luke Martin

In her two decades at JetBlue, Joanna Geraghty has worn almost every hat. Familiarity can foster inertia, but in stepping up to the top job, she is proving that a broad knowledge base can also be an advantage.

When it comes to risk, it helps that business-as-usual isn’t an option. The airline is badly bruised from two failed tie-ups and especially exposed to industry-wide engine problems and air traffic control bottlenecks.

“We have 25,000 crewmembers who rely on us to put food on the table, put kids through school, and at the end of the day, we’ve got to get JetBlue strong and healthy to do just that,” she told the Skift Global Forum last September.

Geraghty’s response? Lean into uncomfortable decisions, trim unprofitable routes, rethink fleet strategy, and position the company for resilience over short-term wins.

The shock sale of JetBlue’s venture capital arm in May illustrated a more aggressive approach from the former lawyer. Geraghty said the move will allow the company to “focus on [its] core operations.” After a messy uncoupling from American Airlines and the Northeast Alliance, she is steering JetBlue into a new commercial partnership with United. Dismissing speculation that it is the first step towards a merger, she said: “No, we’ve spent a lot of time with the Department of Justice over the last five years and we’re playing it safe.” The deal’s speedy passage through the DOT left some asking if Geraghty and team played it too safe.

It’s a reminder that her approach to risk is surgical rather than swashbuckling. Geraghty’s leadership balances urgency with care, boldness with caution, and perhaps above all, a refusal to lose JetBlue’s culture-driven soul amid the storm.

– Gordon Smith

Starting an airline is a notoriously risky venture. They require huge levels of capital, only for most to go bankrupt. But for David Neeleman, who bears the rare distinction of being a “serial airline entrepreneur,” starting new airlines is natural.

Neeleman has founded Morris Air, JetBlue, Azul, and, most recently, Breeze Airways. He also helped found WestJet, Canada’s second-largest airline, and a reservations and check-in system that Hewlett Packard eventually acquired. With the exception of Morris Air (which was acquired by Southwest Airlines in 1993), all of the airlines Neeleman started are still in business, an exceptionally rare feat.

“Other than insanity, I would say every one of them has a story and opportunity,” Neeleman says. “You know, I don’t do it just for the sake of doing it.”

Now, as the CEO of Breeze, a low-cost carrier that offers upscale products, he’s been ahead of the curve when it comes to making the model profitable. Breeze introduced premium seats, free Wi-Fi, and bundled fares during its 2021 launch. Many similar carriers are now following Breeze’s lead.

Such risks have worked well for Breeze. In January, the company reported its first profitable quarter amid a grim landscape for many of its peers. But for Neeleman, his success in the industry wasn’t necessarily rooted in a lifelong interest in aviation. “I was just in the industry that I’ve always kind of fancied myself as an innovator, and it was an industry that really needed innovation,” he says.

– Meghna Maharishi

Matt Welle co-founded Mews in 2012 with Richard Valtr, and has led the company in its drive to become a global, cloud-based hospitality platform.

Used by over 12,500 hotels in more than 85 countries, Mews offers a property management system (PMS), a booking engine, a variety of tools to improve the guest experience, and analytics.

The company closed a $75 million Series G funding round in May, bringing its total funding to about $410 million. Its valuation last year was $1.2 billion.

With this money, Welle plans a few things: He wants to expand further outside of Europe, he wants to push AI, and he wants Mews to become an “all-in-one” solution for its partners. “We have obviously been known as a European tech company, but the U.S. is such an exciting market that we have doubled down on. We now have more than 150 employees on the ground, and we’re adding another 50 people in the next couple of months,” Welle says.

He is also betting on innovation. Of the 1,300 employees at Mews, around 500 are in research and development. “We invest more in research and development than any other hospitality tech company because we believe we have to stay ahead of the curve,” Welle says. “We will continue throwing money at that, and also at fintech.”

– Josh Corder

Palantir is everywhere. The software company has lucrative (and sometimes, controversial) partnerships with governments around the world and works with some of the biggest companies, including Amazon Web Services and IBM. Sometimes the political views of its founders, which include Peter Thiel and Alex Karp, also make headlines.

Even though Palantir is known for its work in the defense industry, the company is expanding into the private sector — and making major strides in travel. Under Karp’s leadership, Palantir is inking partnerships with some of the biggest travel companies, including Airbus, Archer Aviation, and Hertz.

Why is Palantir so bullish on travel? Breno Helfstein Moura, Palantir’s head of hospitality, said on the Skift Travel Podcast that the company sees an opportunity to modernize the technology powering the travel industry.

“It could be revenue management, it could be improving the rates of a hotel or an airline, it could be helping maintenance of airlines on the ground, but it could also be helping the supply chain,” Moura said.

Karp has not been afraid of courting controversy. He once testified to Congress that his company is used “on occasion” to kill people. He’s been outspoken on some of the biggest political issues in the U.S., including the Israel-Gaza war (Palantir has a contract with the Israeli government). He says some of his critics have just called him “batsh** crazy.”

But that controversy hasn’t deterred travel companies — especially at a time when everyone is looking to integrate AI into its operations.

– Meghna Maharishi

Barry Sternlicht surprised the hospitality industry this year by reviving the Starwood Hotels brand. After three decades of transforming hospitality, the 64-year-old mogul is betting his legacy on proving that lightning can strike twice.

The revived Starwood begins with three brands (the eco-conscious 1 Hotels, ultra-luxury Baccarat Hotels, and lifestyle brand Treehouse Hotels) with 15 open hotels. There are more than 40 properties open or in development.

He grew Starwood Capital Group from a $20 million startup in 1991 into a real estate powerhouse managing $115 billion in assets today. Yet he says his proudest triumph was building Starwood Hotels.

Sternlicht created the iconic W Hotels chain in 1998, surpassing expectations with glamorous lobbies and sleek design. He acquired and refined the Westin brand and introduced innovations like the Heavenly Bed. Starwood’s loyalty program earned fans for not having blackout dates and having many partnerships with non-hotel brands.

He departed from the CEO role at Starwood in 2005, and Marriott acquired the portfolio for $12.2 billion in 2016.

Sternlicht’s leadership edge remains his obsessive attention to detail. He’s called himself “the style police,” personally offering input on everything from pillow counts to porter protocols. An avid art collector who studied liberal arts at Brown, he draws inspiration from modern art and architecture as he guides hotel design.

Referring to his revival of Starwood, Sternlicht recently described himself in June at the NYU IHIF hotel conference as “a singer having one song” who wants “two songs.”

“This is my passion,” he says. “Designing hotels and keeping them on brand is fun.”

– Sean O’Neill

Zhang Xiaoqiang, chairman of Shanghai Jin Jiang International Hotel Co., oversees the world’s second-largest hotel group, with 1.29 million rooms and a 13% share of China’s market. But while Jin Jiang dominates at home, Zhang’s ambitions are global.

In 2015, it bought Louvre (at the time, Europe’s second-largest privately held hotel group) and Vienna Hotel Group. In 2016, it took over Plateno. In 2018, it bought Radisson Hotel Group. It currently owns 5% of Accor. Zhang has pushed Jin Jiang Hotels to seek an IPO in Hong Kong and has told investors the goal is to support international growth.

Louvre is in a multi-year turnaround effort with plans to renovate and remodel 80 hotels, mainly in France, and sell other low-performing hotels.

In China, Zhang has released a “12+3+1” brand strategy, which strives to build 12 mature brands by 2028, strengthen three core mid-to-high-end brands by improving guest experiences, and launch a vacation rental business. And last year, it created a joint venture with Ascott China to expand two serviced apartment brands.

Zhang also has his eye on Asia Pacific, a popular destination for Jin Jiang Hotels’ 205 million loyalty program members. The company had a strategic win in May, when it orchestrated a joint venture with Malaysian hospitality group Riyaz to establish RJJ Hotels. It aims to have 108 hotels operational across Malaysia, Indonesia, Vietnam, the Philippines, Cambodia, and Laos within five years.

–Sean O’Neill

Prince Abdulaziz bin Turki Al-Faisal is the Saudi Minister of Sports who bet the Kingdom on travel.

When Prince Abdulaziz took over as sports minister in early 2020, the Kingdom was still a fledgling player in the global sports economy. Five years later, it’s become one of the most aggressive bidders for the world’s attention and its tourism dollars.

A former professional race car driver, Prince Abdulaziz logged years on Europe’s racing circuits, including Le Mans and the FIA GT3 series. Now that same nerve is powering a national rebrand, with the prince overseeing one of the most expensive experiments in sports-led tourism.

Saudi Arabia is committing tens of billions of dollars to bring global sports – and the global spending public – through its borders. That includes a multi-billion investment in sports between 2021 and 2030, part of Crown Prince Mohammed bin Salman’s broader Vision 2030 initiative to diversify the economy away from oil.

But perhaps no gamble is larger than the Kingdom’s successful bid to host the 2034 FIFA World Cup. The decision to pursue the tournament was made public just hours before FIFA’s deadline last October. Within weeks, Australia – the only other potential contender – withdrew, citing logistical and timing challenges.

Asked at the Saudi Arabian Grand Prix in Jeddah about the 2034 World Cup, the prince replied simply: “We’re ready, or we will be ready, inshallah.”

– Sarah Kopit

Nguyen Thi Phuong Thao built her career on the art of the calculated gamble. Vietnam’s first self-made female billionaire, she transformed how the country travels through low-cost carrier VietJet Air.

Popularly known as Madame Thao, her instinct for opportunity surfaced early. While studying economic management in 1980s Moscow, she imported fax machines and latex rubber. By the time she turned 21 – before even graduating – she made her first million. “I have always aimed big and done big deals. When people were trading one container [of goods], I was already trading hundreds,” she told The Guardian.

After riding Vietnam’s real estate boom, Nguyen applied her Moscow trading instincts to aviation. She researched the low-cost airline model and launched VietJet in 2011, entering a regulated, capital-intensive, and male-dominated sector.

Her bold moves have reshaped Vietnam’s aviation market and forced legacy carriers to rethink how they serve a fast-growing middle class. VietJet now serves dozens of destinations across Asia and shows no sign of slowing.

In May, VietJet announced a joint venture in Kazakhstan. A month later, Nguyen was in Paris signing a deal with Airbus for 100 aircraft. “I have a vision and the determination to make Vietnam a regional aviation hub… [this] is more than a commercial contract – it is a significant milestone that marks the beginning of Vietjet’s new journey,” she told reporters.

Nguyen also thinks big beyond aviation. In 2021, she gave £155 million ($212 million) to Oxford’s Linacre College – its largest gift in 500 years.

“The reward for us comes from the feeling that taking flight is a sign of civilization,” she said in a Harvard Business School interview. “When stepping out of their village, our passengers feel like another person and become global citizens.”

– Gordon Smith

Tony Douglas left Etihad in late 2022 with a reputation as the CEO who grounded fantasy fleets and actually made money in the desert.

Now he is orchestrating the launch of Riyadh Air – a self-described “hospitality and digital company” that just so happens to operate commercial aircraft.

“Airlines have been slow to adapt to how customers live today – connected, mobile-first, and expecting seamless service. Starting from scratch gave us the chance to rethink the experience end-to-end,” Douglas tells Skift.

While most start-ups begin in a garage, Douglas’ began with nearly 200 aircraft on order. “Ordering early wasn’t a gamble. It was a strategic move to secure delivery slots in a constrained global supply chain… We’re confident there’s a gap in the market for a premium, digitally native carrier connecting Riyadh to over 100 destinations.”

Not everything has gone to plan. The company has been forced to push back its launch date towards the end of 2025. It had initially hoped to be in the air in the first half of the year. When the airline eventually takes flight, it’ll launch long-haul from day one.

“By paying attention to the details – from the couture uniforms to the incredible amenities, we’re creating an identity that sets Riyadh Air apart globally… That doesn’t mean we’re ignoring efficiency,” Douglas adds.

For a man who views widebody-first, legacy-free airlines as “less risky than retrofitting old systems,” the concern isn’t betting billions, it’s missing the chance to cement Saudi Arabia’s $30-billion bid for a place on the global aviation map.

-Peden Doma Bhutia

Of all the daring decisions New Yorkers make daily – jaywalking, ordering sushi from bodegas, marrying poets – perhaps the boldest of 2025 is a two-fold political and infrastructural gamble: Gothamites are on the cusp of electing a democratic socialist as mayor and they continue to voluntarily fly through Newark Liberty International Airport.

Electing a mayor who rails against the billionaires who built the City is a bet only New Yorkers would place. The candidate, state assemblyman Zohran Mamdani of Queens, promises rent control with teeth, city-run supermarkets, and a municipal Green New Deal. It’s a civic moonshot for a town powered by Seamless, a broken subway system, and $22 salads. If it works, it might remake one of the biggest travel destinations in the world. If it doesn’t? Well…there’s always Newark airport.

New Yorkers don’t fly through it because it’s convenient (it isn’t). And, truth be told, this year’s touch-and-go air traffic control situation was even a bit much for the most hardened strap hanger. Yet the gates remain packed, filled with people who know better and fly anyway – usually for a good deal.

In other words, there is a particular madness to living in New York City. It’s a place where rules are negotiable. Bureaucracy is a sport. And risk-taking is assumed. For that, New Yorkers, we honor and salute you.

– Sarah Kopit (New Yorker)