Aileen Lee: Cowboy Ventures Founding Partner, Founder of All Raise, 2019 Time 100 Most Influential People

Aileen Lee would be near the top of any short list of the most influential women, and people, in VC. After 13 years at Kleiner Perkins, Aileen struck out on her own, founding seed stage firm Cowboy Ventures, which has invested in many eventual unicorns, a term Aileen actually coined in her famous NYT article. Her conversation with Next Play Founder Ryan Nece explores many of the ways she has felt like an outsider in VC. Her gender is the most obvious, but she also confesses to sometimes feeling like a "guppy swimming with sharks." She's found her swim lane enough to now feel more like a dolphin, not less than, just different. Aileen also shares some insight on where Cowboy is investing these days, and why they increasingly love "un-sexy" businesses, especially those that build software for businesses that rely on archaic systems and infrastructure. Aileen is full of actionable pearls of wisdom that apply to many walks of life. This great friend of Next Play does it all with a humility that almost makes it hard to appreciate just how accomplished she really is.