Matador CEO Says A.I.-Powered Travel Tool GuideGeek Can Forge Human Connections

It’s a brisk morning on the San Francisco Bay as Ross Borden unlocks the door to the Sausalito warehouse Matador Network calls home. The co-founder and CEO of one of the planet’s most prolific travel websites hasn’t been to this dockside doorstep in a while, he admits. He’s got a newborn at home.

As one might expect from a global network of travel writers and content creators, Matador’s home office is seldom used. But as the mid-morning sun begins to burn a porthole to the glistening city in the distance, Borden swings open the latch and takes the pulse of the one-room loading bay framed by natural woodwork, fatigued leather couches, a garage door and a 6,000-pound family safe from a bank in Idaho.

The spires of San Fransisco strike an Oz-like pose over this marina. The specters of Salesforce tower and the Transamerica pyramid loom over Matador’s home like watchful bastions of big tech, monitoring the moves of startup enterprises and next new things swirling around them daily.

“Is that where you keep GuideGeek?” I ask Borden, pointing to the safe.

It is not. The secrets harbored during a years-long development process to create an A.I.-powered travel assistant are unlocked and open for viewing now. They’re public knowledge unleashed among the torrent of A.I. tools being put to use by companies as far ranging as JPMorgan Chase, Netflix and Adobe.

Borden settles in to a comfortable spot in front of a large desk lined with offline computer monitors to tell the tale me the tale of how Matador—a travel website spawned by group emails and a mountain climbing trip to Peru in the pre-blogging era—now finds itself spearheading travel itineraries built by artificial intelligence.

GuideGeek is a Matador’s free, A.I.-powered travel assistant that is currently being integrated into the largest message platforms in the world. GuideGeek’s Instagram following is already more than 1.3 million. It’s on WhatsApp and Facebook Messenger, too. And it works just like a chat or a direct message to a human user on those apps.

GuideGeek gets to know travelers. It attempts to understand the likes, dislikes and motivations of each traveler before cultivating destination recommendations based on specific people.

“It’s read every hotel review, every restaurant review and stalled up the entire internet essentially up until 2021,” Borden says. “It’s a massive resource for planning travel and for people who are traveling right now.”

In addition to hotel and restaurant reviews, Borden says GuideGeek integrates with SkyScanner to find flight deals. It will soon launch live hotel data to allow booking accommodations within the chats as well—and it’s fluent in 45 languages. In galactic terms, GuideGeek is the C-3PO of travel agents.

“What I love about GuideGeek is that you can converse with it,” Borden adds. “As you talk, it’s learning who you are as a traveler and the things you’re interested in. We think it’s the most elegant use of A.I., because it’s just a totally natural language conversation. It’s different from that A.I. trip planner tool that TripAdvisor has, which is still working out some kinks. It’s different than ChatGPT integration in the Expedia app, because GuideGeek doesn’t just spit out a list of top ten recommendations.

“We have trained it to really ask questions,” Borden says. “So, if you ask it for recommendations in Amsterdam, it’s going to ask you about yourself and deliver results that are more tailored to you and more conversational. It’s digging deeper to give you an itinerary really based around who you are as a person to find the right museums, the right restaurants, or—if you want—the right lesser-known places that are hopefully away from the crowds.”

To a seasoned vagabond and travel writer that ditched the planet’s beaten paths long ago, I admit that GuideGeek sounds fanciful. Frightening, even. It sounds like the kind of software the fog-speckled guardians of big tech across the bay would adore. But I didn’t come to Sausalito to hear Borden’s elevator pitch. I came to Sausalito to find out if Matador, the company behind the new tech, has a soul.

Travel is all about soul. It’s about human connection, about natural conversations, spontaneous events and the lessons we take home from the road.

Right now, GuideGeek ambassador and chef Michael Motamedi is traveling the world on a six month quest lead entirely by the A.I. travel assistant. He’s been seen sauntering around Spain, Morocco and France alongside his family, guided by sacrilegious hand of A.I. Anthony Bourdain. The trip, according to Motamedi, is going surprisingly well, though GuideGeek does throw in its fair share of surprises.

On a quest to film the three most famous French cocktails in Paris, Motamedi was told to ask for a Corpse Reviver No. 2, a cocktail he was promptly told is actually from London. While seeking a haircut in Marrakech, GuideGeek lead Motamedi into a market where he did succeed in finding a haircut—inside of a local man’s home who appeared to be a skilled barber simply willing to accommodate a perplexed traveler’s request.

“For me, that’s exciting,” Motamedi relays from the road in Paris. “I come from a mindset that it’s going to make mistakes and it’s going to be okay. In the infancy of Google Maps, you heard horror stories of people driving into lakes or rivers because Google Maps would say ‘turn left.’ With GuideGeek, you have to put your common sense hat on. It’s not perfect, but there are real-time individuals working on this to make sure the details are as good as they possibly can be, and 95% of the time, the answers are fantastic.”

Motamedi says his cocktail quest in France led to some of the coolest bars in the city. There, he made friends, gained a better understanding of the history of French cocktails and “had an amazing time.” He’s still not sure whether GuideGeek knew about a specific home cooked barber in Marrakech or if it just lead him to an area where he was most likely to encounter one.

Borden says GuideGeek now has a 95% accuracy rate. Currently, Matador employs four U.S.-based agents that pour over thousands of GuideGeek conservations each week. They scour the results for kinks, bugs and errors in an ongoing effort to refine the system. Soon, Borden expects the accuracy rate to be greater than 98%, but learning experiences are okay, he says. If anything, they’re a testament that non-human guidance is unlikely to take the humanity out of travel anytime soon.

Borden is insistent that GuideGeek can empower travelers to find greater meaning in their travels. Instead of spending hours filtering through results on search engines, Matador handles the heavy lifting. In an instant, travelers are directed to digital sign posts pointing to real world destinations.

A recent internal study concluded that one third of Matador readers and social media followers were likely to use A.I. to plan trips in 2023. And that sample size is significant.

Matador charts between two and five million website visitors in an average month. Their short form videos generate around 180 million views per month. In addition to being the top travel platform on TikTok, Matador’s Creator Network acts as a liaison between travel brands like tourism boards and hotel companies to place content creators in the midst of destinations flush with content opportunities. Borden, clearly, has a hive of movement going on behind the scenes; but he still wears the aura of a backpacker, a “dude with a bag” that tore through the pages of countless Lonely Planet guidebooks in an age when reels had more to do with fishing than filmmaking.

As a travel writer, I’m curious to pinpoint A.I. as good or evil. “Will it take the jobs of writers?” I ask. The question floats over the floor, over a can of sparkling water before landing on the ground with a dud.

Like many outlets, Matador has experimented with A.I.-powered stories. Most of those, Borden says, were littered with too many liabilities to be published. But GuideGeek is not just powered by ChatGPT. It’s based on its own software that’s tailored to a specific task.

While Borden acknowledges GuideGeek has the potential to transform Matador’s business, he says human connection is still at the heart of travel. He notes some media outlets are using A.I. tools to power published copy; but says the written content at Matador leans heavily on human experiences, which can’t be replicated by A.I.

A.I. can guide you to a great restaurant or hotel, Borden explains. But despite early attempts to meet up with its makers in the real world, GuideGeek can’t go to a chef’s dinner in Italy and tell you about the incredible experience that it lived. Matador still needs humans to craft that story.

“The power of GuideGeek is the accessibly and speed with which you can explore options very quickly. It does read every review on the entire internet. So, it knows where to go before places get crowded. It knows when there are no ATMs on a particular island and it has answers, where travel writers have experiences. We spoke to some companies before ChatGPT-4 launched that told us no content will be written by humans a year from now. I just don’t believe that.”

Borden imagines a near future when GuideGeek directs travelers to destinations like “the coolest waterfalls in Bali” and then connects humans with that experience by booking flights to Bali lodging in Bali and showing them videos (Matador owns a massive library of original content) of people swimming underneath those waterfalls.

“A.I. has not been under those waterfalls,” he adds. “But it will show you people doing that and help make the connection more real for humans.”

In doing so, Borden believes GuideGeek can drastically reduce the amount of time people need to plan trips, providing more time to enjoy experiences on the ground.

Borden digs through his memory to another time—a sunset on the side of a 5,800-foot volcano named Misti near Arequipa, Peru. A younger man then, fresh out of college, Borden and a group of friends clung to the mountainside with tents, camp stoves and sleeping bags. On a trip with a budget so tight they agreed to avoid splurging even on hostels, the group of post college climbers let camera shutters clack in the radiant, fading light.

Days later, they descended the peak and bee-lined to an internet cafe, launching the photos into space in a group email to 96 humans back home.

That was the beginning of Matador.

“It was exciting and fun and satisfying to relay those stories to our friends that had not taken the dirtbag route. We got tons of emails back from them,” he recalls. “They went right into their nine-to-fives out of school.”

Decades later, Borden is still on a mission—now powered by A.I.— to free them all.

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