Sally, the owner of Oiselle, invited Fleshman to see their business headquarters in Seattle. Fleshman felt drawn to the space for its small size (reminding her of her own business in its infancy) and to the all-female staff and focus. She went for a run with Sally, who understood her frustrations with Nike.

Fleshman discussed her concerns over the latest young female phenomenon, Mary Cain, training with Alberto Salazar, with Oiselle investors.

Fleshman, now three months pregnant, signed on with Oiselle; she was the first athlete to sign an endorsement deal while openly pregnant. Although the starting salary they offered was small, they also made Fleshman a partner in the business and offered her stock.

Fleshman modeled Oiselle workout clothes on the runway at New York Fashion Week a few months after the birth of her son, Jude. Realizing that she was contributing to the pressure on women to return to pre-baby weight, she was quick to publish other, less flattering photos of herself, which trended with the hashtag #KeepingItReal.

Fleshman began writing a column for Runner’s World. For her cover photo, she objected to their creative guidelines specifying that women must wear form-fitting spandex shorts, insisting on wearing her looser-fitting ones.

Oiselle circulated Fleshman’s “Letter to My Younger Self,” and Fleshman was celebrated for her advocacy on social media.