On Nov. 7, 2012, Jess Lee published a blog post titled “Why startup founders are so unhappy.” In it, she reflected on her experience building the fashion tech site Polyvore, and the unique challenges she faced as a self-described introverted CEO.
At the time, Polyvore was cash-flow positive and approaching 20 million unique visitors per month. The company had raised a $14 million Series C round earlier that year (and more than $20 million total). The five-year-old start-up was proving itself a success. Even so, Lee said that she struggled with moments of “extreme unhappiness”—something she identified as universal among startup founders, no matter their temperament, because of the high volatility and uncertainty of the journey. But early on, her introversion held her back in dealing with that unhappiness in one critical way.
Because she hated networking so much, she mostly kept her head down during Polyvore’s early years. In hindsight, she identified that as one of her biggest mistakes:
Without any perspective from other founders, my only data points on startups came from TechCrunch, which is filled with overnight success stories and positive spin. Therefore, every one of Polyvore’s problems felt like the end of the world to me. After I started talking to other founders, I got the benefit of their wisdom, their encouragement, and their suggested solutions. It was a huge relief and good for my mental health.
Fast-forward exactly four years, and on Monday, Nov. 7, 2016, Lee began her job as Sequoia Capital’s first US female partner. After eight and a half years building Polyvore (and eventually selling the company to Yahoo for more than $200 million in 2015), Lee decided she wanted to advise other startup founders. She tweeted about it when her hiring was announced, linking to her 2012 blog post:
Excited to help other entrepreneurs navigate the roller coaster that is startup life. The struggle is real :-) https://t.co/s4HW2vAU1N— Jess Lee (@jesskah) October 20, 2016
Lee had found a way to get over her fear of networking by bringing a social connector with her to events to navigate the scene. And while she did her fair share of public speaking during her tenure as CEO, she also found that by spotlighting employees and asking them to take the floor, she gave them a greater sense of ownership.
“I don’t think I quite fit the traditional mould for what a CEO is supposed to be like,” she wrote on her new Sequoia bio. “Personality-wise, a certain set of skills, being introverted—none of those things are your classic CEO. Figuring out how to lead in my own style, authentically, has shaped me tremendously.”
Instead of holding frequent group meetings, for instance, Lee opted to meet 1:1 with employees throughout the company, a move that suited her personality type and gave her a competitive advantage in rooting out issues. “I have a lot of 1:1 conversations with people, which means that I have more time to get know someone better, or time for them to tell me if there’s a problem,” she explained to Quartz earlier this fall. “As a leader, you can’t fix problems that you don’t know about.”
She emphasized that the strategy only works, however, when a leader is willing to be transparent with their employees. “When you see leaders being authentic and being real and talking openly about their failures and not just the successes—and not just talking about how awesome the company is and how awesome they are—it creates an environment where people feel more comfortable approaching you,” Lee said, noting that she made a point to be open with employees about the company’s financial situation and strategy, and for the most part “telecast” her own emotions. “If they see you be vulnerable then they’re more willing to be vulnerable with you. That’s part of what makes leaders approachable.”
Netflix’s Reed Hastings, she said, is an example of a leader who “does a good job of coming across as a normal human being.” After the very public failure of Qwikster, which led to a PR disaster and a major drop in stock, he spoke “openly and authentically about it … and that was really refreshing. For a leader to say that [he failed] it makes you trust them more.”
As an investor, surfacing problems from entrepreneurs is a critical part of Lee’s new job. Her ability to see vulnerability as strength—through her own experience, and identifying it in others—is one of the biggest assets she brings to the table.
(Image via Flickr user fortunelivemedia)