Rejection, embarrassment and failure. Stitch Fix CEO Katrina Lake ’05 told students that “you would think that 50 venture investors telling me no would make me less confident.” 

“But I would argue that it ultimately made me more confident.” 

Now one of America’s richest self-made women, Lake told students at a Wednesday talk sponsored by the Stanford Technology Ventures Program that she grew her confidence by putting herself in embarrassing situations and embracing rejection.

Lake is the founder and CEO of Stitch Fix, an online fashion subscription service that sends personalized clothing items to subscribers. In 2017, Lake became the youngest woman to take a company public. (Bumble CEO Whitney Wolfe Herd now holds this title.)

“I am a confident person, and I’m not sure that I would have said that when I was a student at Stanford,” she said. “Like a lot of things, it’s learned — it’s a skill that you can develop over time.”

To illustrate her point, Lake told a story about a time at Stanford when a friend asked her to fill a vacancy on the squash team just days before the national competition. With no prior experience, Lake competed against students who had been playing squash their whole lives. She said the experience was humiliating, but she now laughs about it. 

She encouraged students to step outside of their comfort zones and to do things that they think are “mildly embarrassing.” According to Lake, if you continue doing embarrassing things, they eventually will not be embarrassing anymore. She said that her experiences with embarrassment and rejection ultimately benefited her. 

“Getting rejected from jobs, getting rejected from schools — ironically I think those things actually can, in the right light, make you more confident,” she said. “I think so much of the confidence question is a fear of the unknown.”

Lake added that part of encouraging people to take risks and to become more confident is to shift the burden of imposter syndrome, a feeling of inadequacy and self-doubt, from the people who experience it to the community that causes it. According to her, imposter syndrome currently puts the burden on women and underrepresented communities, when it is really a communal problem that everyone needs to help solve to ensure equal access to success. 

Now, Lake is investing in companies in an attempt to uplift these underrepresented communities. She said that she only invests in diverse founding teams because it’s the best way to build wealth in underrepresented communities and to create a diverse future. 

“I’m putting my money where my mouth is, and I’m backing people that I know share the same values as me,” she said.