She invested $10,000 of her family’s savings into giving the idea a six-month go. She named it We Are Rosie, after her young daughter, Margot Rosie, with her own and her family’s legacy in mind.


“There’s a component of my desire to honor the people that came before me, but also to leave a legacy for my kids, because I don’t ever want my daughters to be trapped in a job where they’re mistreated, or they have to sacrifice themselves or their family to participate in the workforce,” Olson says.

It worked. Less than five years into growing the company, We Are Rosie is valued at $110 million, and its 2,267 percent three-year growth rate landed it No. 232 on the Inc. 5000 list of the fastest-growing companies in the United States.


The We Are Rosie platform and community includes some 17,000 marketing contractors, whom the company places at firms for project-based work, capped at 40 hours per week. The company itself has 60 employees, all of whom are remote and enjoy a slate of family-friendly benefits, including mandatory vacation. It’s a perk Olson put in place to combat burnout during the pandemic, inspired by advice a mentor gave her: “People do what you pay them to do.”

“I thought: How can I pay people not to be burned out?” She tied it to quarterly bonuses: To earn their full bonus, an employee must take at least five vacation days every three months.

To listen to my full interview, click here, on the player above, or find What I Know on Apple PodcastsStitcher, or anywhere you get your audio.