They Persisted

- Polina Raygorodskaya

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 Raygorod skaya, who’s now 31.