Catherine
Heald

The Dossier

Right now, somewhere over the Himalayas, a reconfigured Airbus is carrying eighteen people who could buy the plane. Catherine Heald drew the route. She picked the monastery, the helicopter pilot, the man who would pour Champagne at 14,000 feet while Everest sat in the window. The guests think they are buying a holiday. They are buying her phone book.

Heald is co-founder and CEO of Remote Lands, the New York and Bangkok tour operator that designs bespoke private journeys across Asia for celebrities, Fortune 500 chiefs and the kind of wealth that travels with security. She is also the exclusive operator of Aman Jet Expeditions, which strip a 140-seat jet down to roughly eighteen and limit the manifest to eight or nine couples. The starting price of a three-week, seven-country run is $188,888 a head. People pay it.

"Anyone can plan a fancy trip and book expensive hotels, but my aim is to take travelers to a deeper level - to people and places they would never have thought to try on their own."

The interesting part is not the price. It is that the woman selling the most analog luxury on earth - a guide who knows a Bhutanese abbot by name - spent her first career writing software.

The first act ran on floppy disks

She was born Catherine Evans in Pittsburgh, went through Shady Side Academy, then crossed to New York for Barnard College at Columbia. She studied computer science when Columbia had only recently made it a major, graduating in 1984. The next three years she spent writing code for the Wall Street firm LF Rothschild while chipping away at an MBA at NYU's Stern School - a degree she abandoned the moment Hong Kong called.

In 1987 she flew east for what should have been a stint. She stayed seven years. By 1989 she had co-founded InterOptica Publishing, one of the world's first e-book houses, pressing 25 CD-ROM titles - many of them about travel - back when a CD-ROM was a small miracle. Apple agreed to distribute them in 1993. The company later folded into the lineage that became Take-Two Interactive, the eventual parent of Rockstar Games. She served as president of Take-Two.

Then came the panther. For her second company, Wanderlust Interactive, she licensed the Pink Panther from MGM and cast him as a globe-trotting tutor teaching kids about foreign cultures. In 1996 she took Wanderlust public on NASDAQ under the ticker LUST - what Crain's New York Business called Silicon Alley's first IPO. She was 33, among the youngest female CEOs of a publicly traded American company, and operating then under the name Catherine Winchester.

Three software companies. One IPO. A cartoon cat teaching geography. And she was just getting started.

The second act runs on relationships

The thread through all of it is Asia, and a fascination that never cooled. In 2006 she reunited with Jay Tindall, an old colleague from the Hong Kong travel-tech world, and they built Remote Lands to own a single niche: ultra-luxe Asia, end to end. The division of labor is geographic - Heald runs sales from New York, Tindall runs operations from Bangkok, so the company is awake on two clocks at once.

The aim was never to be the most expensive. It was to be the most connected. Remote Lands keywords read like an atlas of obsession - Bhutan, Burma, Papua New Guinea, North and South Korea, private islands, helicopter charters, luxury train journeys, off-the-grid spiritual treks. The point is depth. A trip might include a hike to the Tiger's Nest monastery in Bhutan, a private yacht through Phang Nga Bay, or that helicopter loop around Everest with breakfast served mid-air.

The recognition followed the method. Conde Nast Traveler named her a Top Travel Specialist for seven consecutive years. Travel + Leisure put her on its A-List of advisors. In an industry where anyone with a login can book a suite, Heald sells the thing a website cannot: the door that does not have a handle.

Still reinventing the jet

The Aman partnership keeps mutating. Remote Lands has run the jet expeditions for well over a decade, and each year brings new routes - 2025 expeditions across seven countries and three continents, 2026 Private Jet Journeys, 2027 itineraries with fresh destinations. For a former engineer, the expedition is the ultimate system: a flying machine, a manifest of eighteen, a continent of moving parts, all tuned to feel effortless.

What makes Heald worth reading is the contradiction she carries lightly. The serial founder who shipped software now sells handshakes. The IPO veteran now measures success in whether a guest meets someone they will remember for life. She spent the first half of her career teaching machines to do things, and the second half proving the most valuable things still cannot be automated.