Aileen Lee traces her path from Gap's chief of staff under Mickey Drexler through an apprenticeship at Kleiner Perkins under John Doerr to co-founding Cowboy Ventures. She explains how VC works as a mentorship business, sharing practical lessons from working with founders and portfolio companies.
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The CEO of Gap at the time was a guy named Mickey Drexler, who's probably one of the greatest living merchants in America or in the world. After Gap, he did J. Crew. He's just an incredible retail leader and merchant, and he had this internal star search to pick. He had decided he was going to take on a chief of staff every year, and I wound up being a finalist. And he basically put maybe 8 or 10 of the finalists at a lunch table together. And he basically would just sit. He'd. He sat there and he just peppered us all with questions. It was such an odd process, but he really wanted to know where you came from and what you cared about and what your values were and what motivated you. And I talked a little bit about my family, and I talked a little bit about working in retail, and I talked a little bit about caring a lot about customers. And I don't really know what it was, but I got the job. So I wound up being chief of staff to the CEO of a public company when I was just a year out of business school. And I just worked my tail off. I was there two hours before he showed up every day. I was there for two or four hours after he left every day. And it was, like, ridiculous multitasking, because on the one hand, it's a public company, and you're supporting the CEO who's got shareholders and real estate and debt and financials and analyst reports and store reports and international and Gap and Baby Gap and Banana Republic and all these different things. And we care a lot about customers. We would read customer complaints. We would read letters and write them back. So kind of from the high to the low, it was an amazing. And then also, sometimes people would, like, you know, some famous actor or journalist would walk in, and Mickey would say, what's happening? Dennis Hopper? And Dennis Hopper would be like, dude, Stockholm is so cool right now. And then he would just look at me and he'd be like, make it happen. And then, like, basically, 48 hours later, I would be on the phone calling all of Mickey's friends, being like, what are the cool stores we should visit? What are the right hotels? What are the restaurants? What are the cool trends? What street should we go to to see people wearing streetwear? And then, like, three days later, we would have this junket of Gap people going to Sweden or going to Stockholm to check out the fashion and the style and the culture and putting together two dream days. It was just like every day, your schedule would get totally blown up, and you'd Be doing crazy things. And after that job, I got to kind of pick where I went in the organization. And I picked the Internet job. The Internet business was the thing that was kind of, I thought, the most exciting gatt.com and it was a tiny team. And so we were just really trying to. It was like a startup inside of a big company. And we just had to learn about. What do you do to run a site every day? Do you change the homepage every day? Do you keep it the same? Do you send emails? Do you not send emails? What do you do with customer data? So many things that there are no rules back then. And we just were trying to figure it out. And so I guess all those things prepared me for going into venture capital in the way because I got exposed to a lot of different functions I did inside the same company. Change jobs pretty much every year. And the chief of staff job actually helped me because I effectively went to Kleiner as a chief of staff, as one of the associates working for John Doerr. And just John had such a full plate and so many different portfolio companies, and so many people wanted to meet with him. And it was really important for us to make sure we always showed entrepreneurs the utmost courtesy and professionalism and attentiveness. And then also he had a lot of kind of political or kind of civic cause, things that he was passionate about, like public education and improving California schools, things like that. And so I just was constantly thinking about what is important to John and what are his priorities and also what are the priorities of the firm. And I just tried to apply myself to whatever things needed to be done so that we could accomplish our goals as a team. And I think that mentality, I mean, it's something that we talk about at Cowboy Ventures that has served me incredibly well in my career. So that whenever I got placed into a situation where I didn't really know a lot, you know, I'm trying to learn and I'm asking questions so I can make the team achieve its goal, help the team achieve its goals. And so it has. Basically, lots of people were helpful to me to help me figure out the things that I don't know. So I'm trying to think about. So the VC mindset was, in my opinion, VC was an apprenticeship business. So I didn't jump in and say, oh, yay, I'm ready to be a vc. I took the job and I was like, I'm ready to learn and serve. And that's basically what I did for five or six years, working for different partners, first John, and then different partners at Kleiner Perkins, and trying to understand how they work with their portfolio companies, how they help founders navigate problems, how they help them raise money or introduce them to customers, or work on marketing programs or those kinds of things. And so I kind of learned through apprenticeship by going to lots of. Lots of meetings and spending a lot of time with founders interviewing candidates, trying to understand, like, if a candidate didn't work out, why, if we were part of the interview process, what should we have asked differently so that we could have figured that out? So I just did that for many, many years. And that was what kind of helped me develop my mindset as an investor, also getting to see what happens to the company. So you have a thesis, you write a memo, you do your diligence, you make the investment, you work with the founders for a number of years, and sometimes it goes well and sometimes it doesn't. And so trying to basically piece together some heuristics about, like, what do they have in common, or what are the signals that you can tell you're at a fork in the road and that you need to help the founders understand that they're at an important fork in the road and that the decisions that they're going to make could basically send their company in this direction or in this direction.
