And I think it's important for them to actually hear what people are worried about - where they may have blind spots, bumps that are coming ahead in the road - so that they can be prepared," she said. "I think a lot of founders are just being shined a lot of time. And she offers tough love, in contrast to this era of super "founder friendliness," as she put it. She helps with hiring, financial plans, crafting the perfect pitch deck, and troubleshooting bumps. These days, Lee prides herself on helping founders, not being their overlord. So she left the comfort of her established role and took a similar risk on herself. "And I'm definitely by nature more of a collaborator. "It seemed a little more collaborative, like they were coinvesting with each other," she said. She was intrigued and soon learned the key to seed investing was just as much about working together with other early-stage investors as it was about supporting founders. "The seed investors were just starting earlier and taking more risks when there was really, very little due diligence," she said. These were riskier investments into startups that hadn't proved themselves, but the early funding gave them an outsize share of the profits relative to those of investments down the line. In 2010, Lee noticed a trend: Her peers, including Steve Anderson and Ron Conway, were forgoing backing startups at the midstages in favor of seed investing, often being the first check into a startup. Lee learned the trade of startup investing from John Doerr, a famed investor and the chair of Kleiner Perkins, and she was soon racking up Series A and Series B deals for Kleiner Perkins, like the consumer megahit Rent the Runway. Both lists were compiled with data from Tribe Capital. 2 on Insider's Seed 25 list of top female investors and No. With that track record, Lee is ranked No. Others in Cowboy's portfolio include Chime, which is headed for an initial public offering, and Product Hunt (which sold to AngelList in 2016 for $20 million, TechCrunch reported, citing a person close to the situation). Her investments include Dollar Shave Club, which sold to Unilever for $1 billion in 2016, the edtech unicorn Guild Education (valued at $3.75 billion in the summer), and, most recently, the no-code marketing tool Mutiny, which raised an $18.5 million Series A in September led by Sequoia Capital. The leap of faith for Lee has been worth it: Cowboy Ventures has invested in over 140 startups and raised three funds, with the most recent one closing at $95 million. I was wondering after leaving, 'Would anyone still talk to me?'" "It was like leaving the Harvard of venture capital. "It was scary," Lee said of her decision to leave Kleiner. It was much rarer in those days for anyone to fire up a new fund, but on top of that, she was one of the first women in venture capital to start her own firm. 33 on our Seed 100 list of best early-stage investors.Īfter spending more than a decade at Kleiner Perkins, Aileen Lee made what felt like an enormously risky career decision: In 2012, she went out on her own and founded a seed fund, Cowboy Ventures (named after her son, Cowboy Stinson). She founded one of the first major female-led seed firms, Cowboy Ventures, and never looked back.
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