Sitting down for dinner at a popular South Boston restaurant, Polina Raygorodskaya ’08 is faced with a decision: What wine should she order? “I like things sweet,” she tells the waitress. “What’s the sweetest wine you have by the glass?”
Raygorodskaya has a reason to celebrate this evening, but that’s nothing new. Her business is going well. Actually, it’s better than well. “We just hit a sales record this week. That happens all the time now,” says Raygorodskaya, a menu open in front of her, the dinner crowd slowly filling up seats around her.
Raygorodskaya is co-founder and CEO of Wanderu, a travel website and app that allows consumers to search bus and train schedules and book tickets. Think of it as Kayak for ground transportation. Experiencing sensational growth, the Boston-based travel company has attracted $8 million in funding in recent years, and billionaire entrepreneur Richard Branson counts himself a fan.
At this moment, though, the matter at hand isn’t business. As she sits in the sleek restaurant, Raygorodskaya is still working on finding a fitting drink. The waitress has returned with a sample, and Raygorodskaya takes a sip. “I can do it,” she says, but adds, “It’s not as sweet as I would do,” a remark that sends the waitress off in search of something else.
Raygorodskaya is someone who knows what she wants. Inspired by the sacrifice and grit of her immigrant parents, Raygorodskaya isn’t afraid to push, to be bold. As she puts it, she’s not content to simply be content. When she was younger, she left behind a modeling career in New York City, in large part because she wasn’t in control. “I like to be in control of my own fate,” she says. “I really quickly realized I hated modeling. You’re just there to have something hang on you while they take the picture.” Later, as a sophomore at Babson, she started a public relations firm focused on fashion. The New York firm thrived and had great clients, but eventually Raygorodskaya left that behind as well. “It wasn’t something I was passionate about,” she says.
When she co-founded Wanderu, Raygorodskaya faced many obstacles: technological hurdles, naysayers, no salary for a year and a half. None of that mattered. “From day one, I knew the company would be successful,” she says. “I’m an entrepreneur. That’s how we are. It’s probably being crazy.”
At the restaurant, the waitress returns with a glass of Moscato d’Asti. Raygorodskaya sips. She nods. The effort was worth it. “It’s perfect,” she says.
Nothing Is Impossible
Wanderu makes its home in a century-old building in Boston’s Financial District. With its red brick, hardwood floors, and wood beams stretching across the ceiling, the office is bright, open, and quiet, which the engineers of Wanderu appreciate as they code. The only sound you’ll often hear in the office is typing.
Wanderu moved to this space in the fall. With the company’s staff doubling to 25 within the past year, a bigger office was needed. Raygorodskaya’s desk sits by the window, which looks out on the Rose Fitzgerald Kennedy Greenway and offers a glimpse of Boston Harbor beyond. Next to her sits Igor Bratnikov, the company’s COO and co-founder. The two have known each other since middle school. They were part of the close-knit Russian community in Newton, Massachusetts, and met while taking math classes at an after-school program frequented by Russian students. She went on to attend Newton South High School, and he went to Newton North. “He’s my best friend,” Raygorodskaya says.
On a recent Thursday morning, Raygorodskaya walks through the Wanderu office eating banana bread baked by a co-worker and sporting a fish pendant hanging from a necklace. “It’s for good luck,” she says. As they do every Thursday, Raygorodskaya and Bratnikov soon gather in a conference room for a one-on-one meeting. Apollo, Raygorodskaya’s Pomeranian dog, also wanders into the room and sits under the table. Normally Apollo has free rein about the office, but this meeting is just between the co-founders. “I don’t know why you’re in here,” says Raygorodskaya, shooing Apollo out the door. “No one invited you to this meeting.”
Peering at a laptop, the co-founders sit side by side, almost elbow to elbow. Wasting no time with small talk, they delve into business matters, dealing with issues big and small: revenue, travel schedules, Wanderu swag, guest bloggers for the website, efforts in Mexico, head shots, meetings. “They work well together. They rarely have a butting of heads,” says Kate Thompson, Wanderu’s operations manager.
Raygorodskaya and Bratnikov started Wanderu out of frustration. Raygorodskaya was a veteran of many a bus ride while running her PR firm, and she was baffled that no site like Kayak was available for buying tickets. To compare prices and schedules, she had to visit each individual bus company’s website.
That frustration came to a head when she and Bratnikov found themselves stranded in a small town in rural Virginia. The pair, along with a couple of other friends, were taking part in an initiative to raise awareness of national parks and forests. The group was to trek to parks across the country and document their travels. For Raygorodskaya, who has a strong case of wanderlust, this seemed like a great summer vacation.
The only catch was that the group had to travel using shared rides, so when a driver canceled on them at the last minute in Virginia, the friends were left stranded. Trying to find bus or train routes to their next destination proved difficult without a Kayak-like site. Eventually, the group broke down and rented a car, but for Raygorodskaya and Bratnikov, a business idea was born. “We decided this problem has to be solved,” Raygorodskaya says. “We’re doing this.”
To start Wanderu, the pair dropped everything else. Raygorodskaya gave up her PR firm and a sought-after loft in Soho, while Bratnikov passed on a tempting job offer that was waiting for him when he graduated law school. Both moved home with their parents in the Boston area and went to work. “It was just the two of us and our own savings,” Bratnikov says. Early on, the pair heard from many in the bus industry who said a centralized travel site couldn’t be done. The industry was too old and entrenched, and each bus company had its own data and system that would need to be integrated into the central site. “If someone said no, we got pissed off, had a drink, and said, ‘Screw that,’” Bratnikov says. “We don’t take no easily.”
Wanderu launched in 2013 and, in time, proved the naysayers wrong. Today, the site works with more than 40 bus companies, and users can peruse about 160,000 bus and train routes for some 2,000 stations across the U.S. and Canada. “Nothing is impossible,” Raygorodskaya says. “That’s something we learned from the very beginning.”
No Reason I Can’t
Facing down the impossible is a big part of Raygorodskaya’s job. After her meeting with Bratnikov, Raygorodskaya returns to her desk to pursue an advertising opportunity that seems a long shot: getting Wanderu’s ad on a billboard at the well-traveled entrance of New York’s Lincoln Tunnel. She spotted the billboard when she was last in the city, and now she has to have it.
“It’s a good spot,” says Raygorodskaya, talking to Wanderu’s creative director, Ani Avanian. This causes Bratnikov to chime in from his seat, “It’s insanely expensive.”
“I’m trying to get it down,” replies Raygorodskaya, undeterred. The billboard owner has a month that is uncommitted to an advertiser, but Raygorodskaya isn’t happy with the price he quotes her. “I said, no, that’s not going to work for us,” she says. Others in the office are unsurprised by Raygorodskaya’s persistence, her willingness to haggle and deal. “She will never buy anything at full price,” Thompson says. “It’s amazing how thrifty she is.”
Whenever she confronts a challenge, Raygorodskaya thinks of her parents. When she was 4 years old, they left behind their lives and careers in St. Petersburg, Russia, and moved with Raygorodskaya and her older brother to the U.S. Her parents dreamed of a better life for their children, but the move wasn’t easy. The family had no money, and they squeezed themselves into a small apartment in Somerville, Massachusetts. Her mother worked as a research assistant, and her father, who barely spoke English, worked as a pizza delivery driver. Knowing he needed a better job to support his family, which soon included another son, he saved his money and began taking computer classes at night. He eventually became an engineer, and that determination and success inspires Raygorodskaya. “They started with nothing and had a whole family to take care of,” she says. “They made it work, and there’s no reason I can’t.”
Later at the office, Raygorodskaya learns that the billboard owner has accepted her offer. Avanian immediately goes to work on designing the ad.
Diving with Sharks
Around noon, a curious smell begins to waft through the Wanderu office. A yoga teacher has arrived, and she has lit incense in the back conference room, where employees move aside a pingpong table so they can lay down their yoga mats and practice. On the conference room wall, near a standing desk with a treadmill, press clippings are framed along with Richard Branson’s scorecard from a startup competition called the Extreme Tech Challenge. Last year Wanderu was one of three finalists, all of which were invited to Necker Island, the entrepreneur’s private getaway. Raygorodskaya and Branson talked about transportation, the billionaire taking notes the entire time, as reportedly is his habit. “He got it,” says Raygorodskaya, who found the acknowledgement gratifying. “What we’re doing matters.”
Now that lunchtime has arrived, Raygorodskaya leaves to grab something to eat. She’s joined by Bratnikov and Staffo Dobrev, Wanderu’s PR manager. Their destination is a nearby Thai restaurant, where Raygorodskaya orders one of her favorite dishes, spicy hot basil. Dobrev has known Raygorodskaya for years, having first worked at her PR firm. Like others at Wanderu, Dobrev praises the respect and support Raygorodskaya gives her employees. “If she sees value in you,” he says, “she will invest in you and nurture you and teach you so you can reach your full potential.”
Lately, Raygorodskaya has been trying to convince Dobrev to go scuba diving. She’s certified, and Dobrev is open to the idea, except for one thing: what might be lurking underneath the water. “I’m scared of sharks,” he says. “She says, ‘If you don’t bother them, they won’t bother you.’ I don’t know about that. Would you go diving with the sharks?” (Asked later about the danger of sharks while scuba diving, Raygorodskaya says, “There are sharks. But they’re small. They’re not great whites or anything.”)
Raygorodskaya certainly has an adventurous streak. It’s no accident she started a travel company. She has traveled to all 50 states and some 30 countries, including New Zealand, Bora Bora, and Myanmar, and she’s constantly on the road for work, whether participating in conferences or meeting with potential partners and investors. “If she had a free month now, she would pack a bag with a few pieces of clothing and see the world,” says Bratnikov. “She loves being out, being free.” For Raygorodskaya, scuba diving, traveling, and entrepreneurship are about the same things—meeting people, pushing yourself, and having experiences. “Nobody who is an entrepreneur wants an ordinary life,” she says.
When she has the opportunity, Raygorodskaya likes to talk to college students about her experiences. At Babson, she felt inspired to take on a business, and she wants to do the same for others. She tells students of her successes and failures, the path that has taken this child of immigrants from modeling, to the PR firm that was her first startup, to her success with Wanderu. It’s a journey that has left her, quite simply, happy. “I love, love what I do,” Raygorodskaya says. “I enjoy working. This is my baby.”
After lunch, Raygorodskaya and Thompson leave the office for a special assignment, heading to a wine store that is conveniently located only a few doors away. Raygorodskaya and her team are not bashful about celebrating successes, and today brings another in a long line of them. On the tech side, the company has constructed a more efficient way to receive pricing and trip data from bus companies. The effort took months of work. “We need some Champagne,” Raygorodskaya tells the store clerk, who leads her to a fridge in the corner. The entrepreneur pulls out two chilled bottles.
Back at the office, Raygorodskaya returns to her desk to do more work. At a table nearby, the Champagne waits to be popped.