Having three distinct careers by the time you're 25 sounds ridiculous, unless you've been reinventing yourself since age 4. In 1990, Polina Raygorodskaya and her family fled Communist Russia, arriving in the Boston area on a refugee visa. "I felt like an outsider," says Raygorodskaya, who, despite being half Jewish and barely able to speak English, joined a choir at the local Catholic church, hoping to blend in.

Ever since, Raygorodskaya has discovered the virtues of adaptation, with a career that has spanned fashion, communications, and now transportation tech. At 16, the lanky high school student caught the attention of a modeling agency and began turning up in ads and walking the runway at New York Fashion Week. Then, when she was 19, studying entrepreneurship at Babson College, small fashion designers turned to her for publicity help, and she hatched a public relations firm.

So when a new business idea came to her in her mid-20s, Raygorodskaya decided it was time to make her unlikeliest career pivot yet. Wanderu, as her new company would be named, was a technology solution for a longtime transportation-industry problem. Raygorod­skaya often took trains and buses across the Northeast to meet with her clients, but there wasn't a single website where you could figure out the cheapest and most efficient routes using different modes of transportation, and then purchase the corresponding tickets. Each carrier had its own ticketing system, and there wasn't an aggregation site like Kayak for trains and buses. "You could find anything else on the internet, but you couldn't get from point A to point B using non-air transportation," says Raygorod­skaya, who's now 31.

In 2013, two years after founding the Boston-based company, she launched the platform: Wanderu helps travelers map out the best sequence of transportation to a particular destination using a combination of buses, trains, and ferries. Then it provides directions between modes of transportation--and takes a cut of ticket sales. To date, the startup--co-founded with COO Igor Bratnikov, a fellow émigré Raygorodskaya met as a teenager at a Russian-language afterschool math program--has booked more than $1 billion in partner ticket sales and now generates over $100 million in annual revenue. "She took a couple of long-distance bus trips and came up with an idea and a team that could solve the problem that I couldn't solve," says Craig Lentzsch, the former CEO of bus giant Greyhound and a Wanderu investor.

In the startup's early days, Raygorodskaya couldn't get transit companies to take her seriously. For the business to work, she needed to partner with hundreds of transportation companies, most of which didn't want to appear on the same platform as their com­petition, particularly one that nobody had ever heard of. Ray­gorodskaya called Lentzsch for help. He agreed to become an adviser, but told her that before he'd invest, she'd first have to prove she could recruit carriers.

Polina Raygorodskaya at Boston's South Station, which, thanks to Wanderu, may soon be much more crowded.
CREDIT: Heather Sten

Raygorodskaya tried courting bus and train companies, but "trying to get through the levels of bureaucracy was impossible," she says. So she reverted to a strategy she had picked up during her days in fashion: ego stroking. She asked to feature the CEOs on her blog. "The second you say you want to interview them, they'll talk," she says. These conversations led to deals with several regional carriers. Lentzsch participated in the company's $2.45 million seed round--along with former Orbitz chairman Jeff Clarke--helping lead to dozens of deals with national carriers, including Greyhound.

Still, the technical challenge was so massive that by late 2014 Raygorodskaya was running out of cash. The seed funding had been used to build Wanderu's own third-party bus and train carrier data system, one similar to what the airline industry already had. But bus data was far more complicated. Whereas airlines travel in and out of the same airports, which use standard carrier codes, buses dock in dozens of places across any given city, and the codes they use vary by operator. Then in November 2014, after months of trying to pull together $5.6 million in funding--and considering salary cuts--Raygorodskaya was able to lock in the investment, giving her time and teaching her a formative lesson: prioritize generating a profit.

On a humid Monday in August, Raygorodskaya gathers her 28-person staff while Bratnikov pours champagne. Since that precarious year of 2014, Wanderu has expanded throughout North America and Europe, boasting more than 300 bus, ferry, and train partners, including Amtrak. Over the past year, it's inched closer to Expedia and Kayak turf, partnering with flight-data provider Skyscanner for airline bookings, with hotel bookings in the works. Raygorodskaya, who was invited to Richard Branson's Necker Island a couple of years ago, has even been promised a capital investment by the mogul. But for now, her most important piece of news is the one she reveals to the staff while tipping her glass in the air: "We are profitable," she says.