Jan 24, 2017 · 12 minutes

Her name isn’t Jess Lee, Ann Miura-Ko, Theresia Gouw, or Ellen Pao. It’s Aileen Lee. And she’s sick of you confusing the five of of them.

Seriously: That actually happens.

Last November, Polyvore founder Jess Lee finally became the first female investing professional at Sequoia Capital, after much criticism, some horrifically gendered remarks by Mike Moritz, and at least one of the partners admitting Sequoia had “a gender problem.”

Aileen Lee posted this on Facebook:

Hmm, should i be flattered, insulted, or just brush off that a number of people have confused me with my friend/great CEO Jess Lee, think i'm joining Sequoia Capital, and shutting down Cowboy Ventures? Do they think what we're doing at Cowboy is not that big a deal; that i'd opt to join a legendary all male firm if given the chance; or that asian women in VC are not worth telling apart? (because Theresia Gouw, Ann Miura-Ko and i often also get confused by people...). Just wondering. 

When she was starting her firm Cowboy Ventures, she says she repeatedly had to explain that although, yes, she was an Asian woman, and yes, she’d previously been at Kleiner Perkins, no, she was not Ellen Pao.

That Lee so openly calls people out who confuse her with other prominent Asian female VCs shows how she feels about gender in Silicon Valley. She is not one of those women who pretends the problem doesn’t exist or says she never faced sexism. She is outspoken about the depictions of women in the venture world, and how much harder they have to work to network and get a deal. (As a mother of three, she’s coming soon to a Uterus Is A Feature not a Bug episode near you…)

That anyone in Silicon Valley can’t pick Aileen Lee out of the very thin line up of prominent women of color in venture capital is getting more absurd by the day. For one thing, she’s the person who coined the term “unicorn” to describe a company valued at more than $1 billion— a more overused buzz phrase at this point than “pivot” was a few years ago. It’s the “dot com” of this era. And thanks to the actual unicorn exit of Dollar Shave Club, Lee is one of a handful of female VCs dramatically boosting their performance across the board, according to a Women.VC study that said women on average perform better than male VCs.

Pretty soon, Lee will be able to test out another sexism cliche in the Valley: Whether people in business meetings naturally defer to a male partner. Up until now, 5-year-old Cowboy Ventures has been an entirely woman-owned, woman-staffed venture firm. Lee is announcing today the addition of a second partner, and it’s a well-known name in the Valley: Ted Wang, who helped run the startup practice at Fenwick, which has clients as tiny as Pando and dominant as Facebook. During our PandoMonthly with AngelList’s Naval Ravikant, he referred to Wang as the “lawyer to the stars” for Silicon Valley. (I’d be committing the same sin as I just described if I didn’t acknowledge that another strong woman, Cindy Hess, ran that practice with Wang.)

Although Wang identifies so much as a “law-talkin’-guy,” that he made Lionel Hutz his Twitter pic, he’s wanted to make a change. Wang is one of those lawyers who wants to go deeper with clients. He’s been in so many board meetings and in so many M&A deals that he can read the tea leaves of what’s really happening, and isn’t happy staying quiet about it. (I know this as an entrepreneur first hand.) I’ll be interested to see who his Twitter picture switches to now… Mr. Burns?

It’s an impressive hire on Lee’s part, and will certainly change the nature of the firm, which has mostly lived or died on her reputation, her deals, and her brand thus far.  No matter how respected Wang is, it takes a big leap of faith to decide to share what you’ve painstakingly built for four and a half years with a new partner.

I caught up with Lee yesterday to talk about the decision and what it means for Cowboy going forward. As I was transcribing our conversation, it struck me how much more she sounds like an entrepreneur than a VC. That is a crucial difference with some of the newer firms that have popped up in the last few years: They are startups as much as they are “gatekeepers.” While a partner at a firm like Sequoia or Kleiner or Accel can sit back and be relatively assured, he or she (usually he) has a steady job for the next ten years or more, startup firms are hustling not quite as hard as the founders they back, but they’re hustling nonetheless.

The following are edited excerpts of our conversation.

Sarah Lacy: Did you always think you wanted to add another partner?

Aileen Lee: I think I always thought it’d be great to have another partner. Starting out Cowboy I wanted to get into business, so I just started it on my own. But I’ve always had a hope that we would not fail in the first couple years, and I’d be able to bring a couple people into the team. I’m a team person; I love being part of a team.

I’ve talked to LPs over the years about that, and the advice that I got was if you are going to bring someone on at the partner level, ideally it’d be someone that you’ve known for a long time. And someone who you really trust. They have seen some partnerships fall apart. Often with the ones that don’t work out; it’s because the people didn’t know each other that well.

So when Ted mentioned that he had decided he was going to try to become an investor, I was sort of like “Oh, that’s interesting…” because he is someone I have known for a long time and I really trust and I really respect.

SL: Can you tell me more about professional experiences you had with him that made you feel like this was someone you could really trust?

AL: We started as friends; we actually met at an election party [more than a decade] ago. And it turned out we lived around the corner from each other, so we wound up having dinner, with [our spouses]. This was before any of us had kids and we just started hanging out. They wound up having a daughter and we wound up having twins, so we ended up seeing each other quite a lot with little kids.

He mentioned outgrowing where he was, so I knew some folks at Fenwick, and introduced him and he wound up going there. And over the years, we always talked about companies, new clients he had taken on.

I remember vividly having a conversation in the early years of Twitter. We had met Twitter at Kleiner and not invested, and he was their outside counsel. He had actually been outside counsel to Odeo and then helped wind down Odeo and turn it into Twitter, and I was like “I don’t get it.” At the time Twitter was like the “I just had a great sandwich for lunch” social network, and I was like “I don’t get it.” And he was like “Yeah, you don’t get it. Let me explain to you why Twitter is so awesome.”

And he gave me this whole explanation that I hadn’t really heard before about why Twitter could be so powerful and why it was also so defensible and why it wasn’t a feature that everyone else was going to have. And he was right.  And so we’ve had those kinds of conversations over the years where sometimes he would say “Explain this to me” or “What do you think about this?” And I would do the same, and it’s been a great [ongoing] conversation to have.

And then there was a Kleiner-backed company I ran for two years, and he was our outside counsel, so I got the experience working with him. There are many lawyers who we get to work with who are more like lawyers, and Ted is more like a business advisor. After a board meeting he will be like, “You know what’s happening now, right?”

He’ll explain to you his interpretation of when a board member said “X” what he really meant was “Y”, or he’d give me advice on “here’s how this could play out” during times we acquired companies. “If they say this, you might want to think about this…” He’s just really good at seeing the big picture, much more so than any other lawyer I’ve worked with.

SL: Whenever I think of lawyers turned VCs I think of David Hornik, who also described himself as one of those lawyers who couldn’t stop advising on the business during his clients’ board meetings. Are there other prominent examples of lawyers turned VCs? I guess, Michael Arrington is one, but I’m not sure how great of a comp that is. He was a better entrepreneur than VC.

AL: VC in general is a really small industry, almost everybody is an outlier, there isn’t any one path. There are journalists who make great VCs. There are operators, engineers, analysts who’ve all made great VCs, there are different types. I don’t actually know him, but there’s a gentleman named Jim Gaither who is a really successful VC. Peter Thiel was a working corporate lawyer, and Keith Rabois was a working lawyer.

So in our vintage there haven’t been as many. Ted running the tech practice at Fenwick is a little unusual, but I think that’s another-- among many reasons-- why I like it. Cowboy Ventures isn’t traditional, and bringing Ted on is a different thing. His experience, his track record at being able to pick people and companies at an early stage, and all the M&A and financings and IPOs and everything he’s seen is going to be hugely helpful to entrepreneurs.  

SL: So where do you see Cowboy going in the next four to five years? It’s one person, but going from one partner to two is a big change.

AL: I don’t know. My goal for this year is to make Ted really successful and continue to improve the way we help our portfolio companies and continue to make us a place the best founders want to work with and co-investors want to work with. We’ll see. I am not trying to build the next Sequoia or Kleiner or Benchmark, but I really admire firms like FirstRound and True and Union Square that have stayed smaller and done great work.

We started almost five years ago, and I think for the first four years I was trying to get us into business and show we can do great work. I feel like we’re on a great path. There’s never victory, but I think adding Ted is a big step for our firm.

SL: What’s been the most surprising to you over the last four or five years doing this?

AL: That’s a good question… I guess I’d reframe it a little as some of the things that have been really enjoyable… you know, seed is a more collaborative stage. We always co-invest with others, and I really enjoy that. I really enjoy that and hope that does not change. I think that’s the way Series A used to be, firms used to split Series A rounds. But over the years, firms wanted more and more ownership, so it’s become more binary. So I really like that seed is a more collaborative phase.

The thing that’s something I knew, but …. It takes a long time to build a big company and companies have ups and downs, so you know that you are in year two of a ten year journey, and you wish you knew how the movie was going to end. But that’s the deal with working with startups. The journey is the beauty of it; it’s not about the end. But, still, sometimes you wish you knew how the movie was going to end.

I really like what we are doing at Cowboy and I feel like we are non-traditional. We are a female-founded firm that is all female currently, and we’re adding a guy. The entrepreneurs that we work with whether we wind up investing or we don’t give us great feedback that the questions we ask and ways we help are different.

And I feel like we’re doing that in a way that is personal. We really care about the people we are working with. Having the chance to start from scratch four-and-a-half years ago and build a more modern firm that is not stuffy and doesn’t have a lot of formality or isn’t set in its ways in the way a lot of VC firms are…. I’m really excited about that. I think it makes our industry more accessible and more human.

But I probably shouldn’t talk about that so much, because it’s also important as a female-founded firm...I feel like a lot of women don’t get credit for being smart, they get credit for being nice and being human. Hopefully people think what we are doing and the way we help is really smart as well.

Great entrepreneurs are always happy never satisfied, and I think that’s kind of how I am. I am happy with how things are going, but we can always do better.