They Per­sisted



Four women with game-chang­ing ideas

De­sign­ing a high-tech so­lu­tion for a thorny prob­lem: mak­ing bus and train travel as ef­fort­less as fly­ing

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 trans­porta­tionin­dus­try 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.

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. –ZOË HENRY

Pho­to­graph by HEATHER STEN

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