Jess Lee’s success comes down to two things: a desire to be surrounded by insanely smart people, and a hunger to learn. It’s what took her to Google straight out of college; to the startup Polyvore, where she became its CEO and oversaw its sale to Yahoo!; and to her new role as the first female investing partner in the U.S. at Sequoia Capital.
It also made her perfect for an onstage fireside chat at our June event.
For roughly an hour, Jess talked about what it’s like on both sides of the investment fence – what inspired her to be an entrepreneur, what she’d tell her younger executive self, and the advice she gives founders today.
It’s the kind of conversation I envisioned when I started UPWARD and that has helped to create a thriving global network of executive women. We have nearly 5,000 members today and my goal is to reach 100,000 in the next five years. To do so, we need to keep telling our stories, giving advice, and lending a hand.
Jess put it well: “It’s up to us to win and do well and make it clear that women can be founders and can be leaders for the next generation.”
Mother Sets Example
To understand how Jess rocketed ahead, you have to scroll back to when she was a child growing up in Hong Kong. She watched her mother run a small translation service from the family apartment, an experience that primed her for startup life.
“It never occurred to me that a woman couldn’t be a leader or couldn’t be a CEO,” she said.
At 17, Jess enrolled at Stanford University and earned a degree in computer science. After graduating, Google invited her to check out its associate product manager program. It was there she met Marissa Mayer, who later became the CEO of Yahoo! and Bret Taylor, who would eventually become the CTO of Facebook.
Jess said to herself, “Wow these people are really smart, I should hang out with them.”
So she did. She also took to heart a comment from Mayer: “She said, ‘I always try to pick the most challenging path because at least I would grow and learn.’”
Little did she know the quirky way her own path would reveal itself.
The Non-Founder Founder
Jess wasn’t looking to leave Google when she came across a fashion Web site called Polyvore. She just wanted to email her suggestions and requested changes to the founders and be done with it. But then they asked: why not come here and fix these things yourself?
“I met the founders and I thought they were really smart,” she said. “And the company was small enough that I could work on a lot of different things. It was just the three founders. I was the first hire.”
After that, life became a blur of building an organization and eventually raising cash – which is no mean feat when trying to convince male funders to back a fashion site for women. So Jess came up with one of the best pitch stunts ever.
“We took a stack of fashion magazines – the September issues with thousands of pages – and threw them on the table in front of the VCs and said, ‘This is hundreds of millions of dollars in ad revenue. Now imagine that on the Internet.’ And they said, ‘Oh, we get it.’”
I asked Jess the advice she’d give her younger self during those fundraising days. She said both the funder and the firm matter. “Ask yourself,” she said, “would the investor in front of you be your first call when times are bad – and more than a cheerleader when times are good? As for the firm, does it have the network of companies, deep knowledge of your markets, and bench of other founders who can help you get better?”
Jess quickly became more than just an employee at Polyvore. She was named an honorary co-founder and in 2012 became CEO. Three years later, she negotiated the company’s sale to Yahoo!, helmed by her mentor Marissa Mayer, for reportedly $200 million.
Next Job Starts With ‘No’
Jess’s third act started in 2010 when she spoke about Polyvore at a Goldman Sachs conference. In the audience were a couple of partners from Sequoia Capital. A few years later, one of them invited her to lunch and asked if she had considered a career in venture investing.
“No way, I’m an entrepreneur,” she told our audience laughing. But she kept the conversation in the back of her mind.
After Polyvore was acquired, the partner reached out again, this time with an invitation to meet other leaders at Sequoia and listen to founder presentations.
“I sat in on pitches. Got into a lot of arguments with partners on why certain investments were great – that I was wrong about. But I met these amazing people and got that feeling that this is what it’s like to be around amazing people again…just like Google.”
Then she said no – again.
The reason was simple: it was too soon after the acquisition of Polyvore to make a jump. But a year later, after the announced sale of Yahoo! to Verizon, Jess called the partner and asked if the job was still available. It was – and it’s now hers.
As an investor, Jess stays focused on consumer technologies. She also spends a lot of time listening and learning. “It takes a lot of data points to know how to differentiate what is a great opportunity as opposed to one that is OK or good,” she said.
But what she does know, and conveys regularly, are the lessons she learned from her life in a startup. She knows that time is a founder’s most precious resource and is willing to point out when they’ve taken a wrong turn.
“When I was a founder, VCs didn’t tell me when I was making a mistake because they wanted to have a good personal relationship. I feel like rather than trying to be nice all the time, the nicest thing I can do is save that entrepreneur a little bit of time.
She also understands what makes a good leader. “Do they understand the problem they’re solving and can they crisply explain it? And is that problem a big enough problem to get hundreds of millions of dollars in investment and billions of dollars in market cap?”
It’s the kind of hard-won perspective she considers not only helpful, but also essential to convey. “I think it’s incredibly important to pay it forward. Just like UPWARD is doing.”
In addition to founding UPWARD I am a Managing Partner at the Westly Group and responsible for investments in software, IOT, and the Internet. I also sit on the NVCA Board of Directors, where I’m actively involved in policy and facilitating collaboration between private and corporate venture firms. Prior to joining the Westly Group, I was a vice-president at Intel Capital and the Managing Director of Intel Capital’s Software and Services Fund and the founder/Managing Director of the Intel Capital Diversity Fund.