Fresh Faces: Jet Set World Travel


Lauren Maggard and Julia Douglas in the courtyard of The Elysian Chicago. Douglas founded Jet Set World Travel in 2005 and was joined by her friend, Maggard, soon thereafter

Introducing four fresh faces taking the industry by storm with a style all their own

Meet the Jet Set girls: There’s the founder and president, Julia Douglas; her best friend and director of operations, Lauren Maggard; and the two independent contractors, Monika Weinsoft of Portland, OR, and Jill Taylor of Little Rock, AR. Together they are Chicago-based Jet Set World Travel.

Why are we telling you this? Because they just might be the hottest thing in travel-selling today. No doubt one of the youngest (Douglas is 28), a trait that helps them cultivate a much-needed, much-younger clientele (85 percent of their clients are under 40).

How, then, does an agency, scratch that “travel consultancy,” which hates booking air (they don’t even use a GDS), doesn’t have office space and has two members with no formal travel experience produce annual gross sales of over $3 million? The quick answer is they are doing things differently.  “We fuse the travel and concierge concepts,” Douglas says. As Taylor succinctly puts it, “We are luxury consultants, not travel agents. There’s a big difference.” The long answer, however, lies at the beginning. For that we go to London.

That’s where Douglas, who was working in insurance at Lloyd’s of London, met Maggard, an art student at Sotheby’s. There, Douglas was tagged with a moniker that stuck. “Every weekend I’d go off to somewhere new,” says Douglas, who speaks in a sprightly manner, befitting someone as passionate about travel as she is. “The joke in the office Monday was, ‘Oh, Jet Set Julia, where did you go this weekend?’”

“Julia was always the person you turned to ask where to go to dinner,” says Maggard, who is just as fervent about travel as Douglas (she’s expecting her first child in April, but was on a plane to Mexico for a fam trip in late February). “She’d whip out her list. It was, ‘Just ask Julia.’”

Decision Time

In 2005, a decision had to be made. Stay in insurance, or…“I didn’t have a mortgage, I didn’t have a car, I wasn’t married and I didn’t have a kid,” Douglas says. She decided to make the leap to travel and moved to Chicago to join her boyfriend and future husband. Starting her own business at such a young age may have been daunting, but she was surrounded by entrepreneurs: Maggard’s parents both were, as were her now husband’s.
“There was enough encouragement and people to bounce ideas off,” she says.

Jet Set World Travel was born, operating out of Douglas’ townhouse. Like anyone starting out, it wasn’t easy at first. “You can have a great idea, but if you don’t have a customer, you don’t have a business,” she says. “I didn’t even know how to earn a commission or what a realistic fee was.” A chance meeting with June Lewis, a consultant with Travelong of Summit in New Jersey, changed all that. Lewis told Douglas about Virtuoso and faxed her a profile of CEO Matthew Upchurch. At Luxury Travel Expo, in September 2006, Douglas met with Virtuoso reps, which led to Jet Set’s affiliation with host agency Travel Experts. But, as Maggard, the blunter of the two, puts it, “Why were we still with them? We wanted to be independent.” Says Douglas, “We wanted to be out of the closet and have our brand visible instead of Travel Experts getting all the credit.” Just last July, Jet Set World Travel became a Virtuoso direct member.

How did the company, in just four short years, become such a powerhouse?
It’s a combination of youth, vitality and the desire to do things differently. “We have the most nontraditional approach,” says Douglas. Like eschewing the GDS, which Maggard compares to archaic DOS language. “We don’t like doing air,” Douglas says. “It’s boring,” Maggard says, displaying a bit of precociousness that has served the business well so far. “We take a creative approach and really listen to our clients—we want to get to know their personal tastes. It’s the same way interior designers go about their job.”

For a while, it was only two. But a 2009 meeting between Taylor and Douglas at Virtuoso’s TravelMart changed that. Taylor recommended her friend Monika Weinsoft, who was looking for a change (at the time she was with Cruise Masters in Portland). She joined Jet Set World Travel in November. (Weinsoft, in 2008, was one of Travel Agent magazine’s “Top 30 Agents Under 30.”) Subsequently, Taylor got to thinking that she too wanted to join the fun. A Travel Agent magazine 2009 Top 25 agent, she joined Jet Set World Travel a month after Weinsoft, leaving her position at Poe Travel in Little Rock.

Jet Set was now a four-woman team. Like Douglas and Maggard, Taylor and Weinsoft, who met each other on a trip to Australia, enjoy quite a rapport. Taylor, the more loquacious of the two, was impressed by Douglas’ smarts and creativity. “I was excited about what she was doing,” Taylor says with southern charm. “She is the next wave and is selling travel the way it should be sold—more in concierge service and consultancy, as opposed to just doing the regular agent thing.” Says Weinsoft, “It’s a new model: travel consultancy service versus travel agency service. Not a lot of agencies are doing it like us. We are envisioning the future.”

Meeting Taylor and Weinsoft was fortuitous; they were in New York hosting one of several client/supplier events, which seek to drum up business. “There was huge buzz after our Chicago event,” Taylor says. She got this a lot: “Who are these Jet Set girls?” They are doing future events in Durango, CO, and Santa Fe, NM.

The two are also using social media to get the word out on Jet Set. The duo’s Facebook page already has 100 fans and is updated frequently with tidbits about their travels, along with photos.

Part of the reason Jet Set World Travel is succeeding is because all four are still hungry and humble. Taylor and Weinsoft are so stoked at what they do, they don’t care if they have to share a room on a fam trip—even better. “We’ll sleep wherever,” Taylor says. “We’re young, but we back up what we do with our production.”

Youth Served

Though small in number, the foursome are pumping out some major-league itineraries. Maggard wins the award for arranging the most lucrative trip: a half-million-dollar European excursion for a family of six. “They were traveling from Wyoming to Paris for three nights, then 17 days through Italy,” she says. Some highlights: occupying the Presidential Suite at the Four Seasons Hotel George V, staying at the top suite at Villa d’Este and cinching a private viewing of da Vinci’s The Last Supper at Santa Maria delle Grazie in Milan. Oh, and the price tag to charter a private jet from the U.S. to Europe: $300,000. “The family sent me 17 roses for 17 beautiful days in Italy,” she adds. “We are the ones usually sending the flowers.”


Douglas visiting Santorini, Greece, in October 2009.



Who says people aren’t traveling? Douglas is currently putting together a 35-day itinerary for a “hedge-fund guy,” which includes 10 days in Morocco, a Nile cruise and stays at the Oberoi and Four Seasons in Egypt.

And what about targeting younger clients? Can this be a viable business plan? Taylor recently put together a seven-week $250,000 honeymoon through Australia, Fiji and New Zealand. The couple was under 30.

All this success has garnered Jet Set World Travel lots of attention. Douglas was tapped by Virtuoso to be part of a group called NextGen, a kind of think tank composed of about 15 agents who are seen as visionaries. The group will meet in Bhutan in May with Upchurch. Douglas is a certified seller of Virgin Galactic space flights. She thinks parabolic travel will redefine the industry. “Think about flying from L.A. to Sydney in three hours instead of 14,” she says.


This Past June, Maggard hiked the Inca Trail to Machu Picchu.

Jet Set World Travel is also gaining corporate attention. Gatorade chose them to design three $75,000 trips for the winners of Gatorade’s Tiger Woods Moonshot Sweepstakes. Meanwhile, Taylor serves on the advisory board for Saveur magazine; Weinsoft in the same capacity for Islands magazine.

Sometimes, the better you do, the more demanding your clients get. Jet Set World Travel was thankful for its first-ever non-family/friend client six weeks into business, the chef at a New York sushi restaurant called Japonais (he found them via a piece on the website, Now, Jet Set has no problem jettisoning a client it thinks isn’t worth its time. The stories are priceless. “We had one client,” Maggard says, “who just checked into the Capri Palace. We received a call shortly thereafter from him, enraged that his bags had not yet been brought up to the room. He wanted us to ring the bell desk to inquire why.” He’s no longer with Jet Set. Another phoned from the St. Regis Bora Bora complaining that water from a faucet had run rusty for a few moments. “How dare you send us here?” she bellowed. They ended up having to move the woman to another hotel; then ended the relationship. “If 20 percent of your clients are taking up 80 percent of your time, then there is something wrong,” Douglas says.


Weinsoft aboard the Paul Gauguin in French Polynesia.


Then there are those you especially want—the so-called whales with deep pockets and a zest for traveling. “We had one prospective client come to us who already was paying a fee to an agency in New York,” Julia says. “He told us outright that he was going to shop us against the agency and wanted us to put together an itinerary for him.” He’s a Jet Set client today.

Not too bad for a Vanderbilt grad who started a travel business with not a whiff of travel-selling experience. She and three colleagues have built something to be reckoned with down the road. Growing the company seems inevitable. “There is no magic number,” Douglas says. “The challenge is finding people who have the right mindset and are able to maintain the brand we’ve built.” She envisions adding as many as two new independent contractors per year.

She already has two good ones, who aren’t only staff, but friends. So much so that Taylor saw to it that Douglas’ February trip to Napa Valley was one to remember. The region is famously known for two things: Cabernet Sauvignon and Thomas Keller’s impossible-to-snag-a-table French Laundry. “I got her a reservation,” Taylor braggingly says. It’s no easy feat. One usually has to call 60 days in advance just to be told nothing is available. That didn’t stop her. “I just worked it,” she says. “I was scared I’d have to fly out there and wash dishes.” Weinsoft notes that while securing things like a reservation at French Laundry aren’t easy, they are easier when you have connections.

The five-hour dinner went off memorably for Douglas and her husband, who couldn’t suppress his excitement and let the cat out of the bag shortly before the evening’s gourmet spectacular. Of course, Douglas was elated. Even so, she wanted to make one thing known. “I know how [Taylor] did it,” she says. We’d never doubt it.


Jet Set World Travel

President: Julia Douglas

Staff: Lauren Maggard, director of operations, and two ICs: Jill Taylor and Monika Weinsoft

Gross Annual Sales: $3.8 million (2009)

Affiliations: Virtuoso Direct Member

Accreditations: Virgin Galactic



Taylor, a Travel Agent magazine 2009 Top 25 agent, joined Jet Set last year.




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