The Flatiron Building, one of New York's most iconic architectural structures, was originally viewed by critics as a disaster: The New York Times called it a "monstrosity," while the New York Tribune declared it "a stingy piece of pie." Even many native New Yorkers do not know that bit of trivia, which is why it's part of the sightseeing tour offered by Nowaday, a newly launched New York City-based startup that wants to be the Airbnb of tour companies.

Airbnb took off by promising travelers a different way to see cities: unique home stays versus cookie-cutter hotels. Nowaday wants to do something similar for attractions. On Nowaday tours, sightseers skip the double-decker bus and traditional tourist traps like Times Square and the Statue of Liberty. They instead hop inside a restored classic car, such as a 1932 Chrysler Imperial or a 1928 Ford Model A, for a 1920s-themed view of Manhattan's less-frequented but historically important sites like Bryant Park and Carnegie Hall. The hour-long tour, which costs $49 per person, is chauffeured by a guide who is dressed in Jazz Age garb--from flat cap to Oxfords.

Nowaday wants to set itself apart by delighting travelers with storytelling, rather than just feeding them standard facts. The ideal Nowaday tour is supposed to evoke a feeling of old New York. Jaime Getto, Nowaday's 28-year-old co-founder, says, "Unlike a traditional tour, it's more of an experience. When you get into our car, you step into the story."

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While the company began booking paying passengers in November, it has been refining its tours and training guides with several hundred trial runs since January 2019. Getto and co-founder Heather Stupi, also 28, have raised ­$3.5 million from Greycroft, Pritzker Group, and the Raine Group in part for their vision for rethinking tourism.

"Venture investors are constantly looking for industries where innovation has lacked for a long period of time, and where a consumer experience is missing the mark," says Will Szczerbiak, an investor at Greycroft. "There aren't many where that's more true than the tourism industry."

The Art of the Excursion

Nowaday's founders, Getto and Stupi, met while working together at the New York City-based recruitment startup Vettery, where Getto was director of acquisition marketing and Stupi was director of operations. The idea of moving into the travel industry developed organically when Stupi hosted a visitor and was lost for ideas when she had to play tour guide. They went on a traditional bus tour and listened to the prerecorded talk, fed through broken headphones. "I felt I walked away with only a few facts and figures, and didn't get the full story of New York," Stupi says.

That inspired the two to research ways to rethink the mundane city excursion. "We landed with cars," Stupi says, "because it provided a way to make the sightseeing experience private and personal." By fall 2018, they had purchased their first car--a Ford Model A--and found their first tour guide.

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Nowaday's staff of full-time employees and mostly part-time guides now numbers 24 and its fleet stands at 12 cars. 

While the vehicles--which are sourced from private collectors and dealerships--remain the centerpiece of the tours, they are but one lens through which to tell the story of New York City. The team wants to dabble in other experiences, molding tours to align with the character of a given city--and they may or may not include cars. When it expands to Los Angeles--which tops its domestic expansion wishlist--Nowaday foresees using 1957 Chevy convertibles to evoke the Once Upon a Time in Hollywood aesthetic. A potential expansion to Paris, the first international city on its wishlist, could be centered around cooking classes, for instance.

"Our mission," Getto says, "is really to tell the story of whatever city that we're in."

Taking On the Big Apple

Of course, Nowaday is just one of many companies that's pitching higher-level experiences to travelers. The San Francisco-based Airbnb launched its "experiences" vertical in 2016, and its full-service "adventures" platform this year. The former typically involves a guided tour or class while the latter involves a small group trip with lodging and meals included. Meanwhile, travel activity sites like Viator, owned by TripAdvisor, and Peek Travel have similar offerings including mixology and pasta-making lessons and classes in photography and pottery. The tie that binds is curiosity, says Alice Jong, an analyst at travel research firm Phocuswright--and a more curated, intimate experience, which is something smaller companies are well-positioned to provide. "This sector is mainly built on the backbone of small businesses," she notes.

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Besides direct competitors, Nowaday's founders still have to contend with legacy providers. Visitors generally do still want to check out the famous landmarks that mass tours offer, notes Jong. So any tourist activity must compete for travelers' time and money, she adds.

Getto and Stupi are well aware of the competition. They're betting their unique spin on tourism will be both needed and welcome among travelers. "Anyone could memorize facts," Getto says. "That's just not engaging." Nowaday's guides, she says, are put through training courses that bake in improvisation and other performance techniques. The focus, she says, is to "master the art of storytelling."?

Greycroft's Szczerbiak is similarly convinced Nowaday's founders will succeed. "They have a real knack for listening to the customer and just delivering," he says.