It was back in the early-2000s, and Lee was on the brink of accepting an engineering position at Intuit after graduating from Stanford with a degree in computer science.
Out of the blue, Lee got a call from Google. Someone had seen her resume and thought she'd be a good fit for the company's elite associate product manager program.
Lee took the interview but tells Business Insider that she was pretty iffy about the position - she didn't know anything about being a product manager and had planned on going into engineering.
Marissa Mayer, now CEO of Yahoo, had started the APM program, and interviewed Lee about the position.
"I straight up told Marissa [Mayer] 'I don't know if I want this job,'" Lee says. "And she said, 'Let me give you some career advice.' And then she told me that you should always take the more challenging path. When you have different options, you should choose the thing that looks like it will be more difficult, because that usually turns out to be the right choice.'"
Lee knew that joining the then-fledgling Google in a non-engineering role would challenge her more seriously than joining Intuit, so she took the APM job. She worked on Google Maps for four years, until she became obsessed with a recently-launched site called Polyvore that let users mix-and-match different products to make digital collages.
After sending a complaint-filled letter to its founders highlighting a bunch of her frustrations with the site, Lee had another big decision in front of her: The Polyvore team had asked her to join the company and come fix the product issues herself. Mayer's advice came to mind.
"When I was thinking about joining Polyvore, I was wondering, 'Should I leave Google's warm embrace to go to this crazy, tiny little startup that no one's ever heard of?'" she says. "I felt like, 'That's going to be really challenging. I should do that.'"
Lee became CEO of Polyvore, a social commerce site that lets users make artistic product collages, in 2012. The company has now been profitable for nearly three years, has more than 20 million unique users every month, and is one of the largest referrers of social commerce traffic on the web, driving more retail sales than Pinterest and Twitter combined.
Lee says she still uses leadership skills she learned at Google and from Mayer while leading Polyvore.