How I Became a Partner at Sequoia Capital & Former CEO | Jess Lee | Talks at Google

Hey, so today, welcome to this talk at Google with Jess Lee. So I'm Dan Carey and joining me is Jess. Hi. She is a partner at Sequoia Capital. Previously she was at Google as a product manager and then Polyvore, which you joined as a product manager. You were then VP of product, honorary co founder and ultimately CEO. Led the company through the acquisition with Yahoo. In 2015, you were Fortune's 40 under 40 list. Glamorous top 3535 women in tech and a whole bunch of other things. So welcome. Thanks for coming.

Yeah, thanks for having me.

So thank you. So what's it like to be back at Google?

Oh, it's totally. It's trippy. It's very surreal. I used to sit in this building in like 2005, I think, when it first opened. Yeah, it's kind of cool to be back. I learned a lot of things on this campus. I was an APM and I worked on Frugal, which was product search back in the day. And then after a short stint there, I stayed. I moved to Google Maps. But this was when Google Maps was a desktop product and we did not have smartphones. So it was a pretty long time ago.

So you joined Polyvore right, from Google. Right. And it was kind of a weird journey. Right? Like it wasn't normal circumstances for leaving Google and joining a company.

Yeah, yeah. I would say it was a little bit of an unusual path. So I remember I was sitting at Google in my office with another Google Maps pm and he was like, hey, you should check out this site called Polyvore that my friend is working on. And I was like, okay, I checked it out. And I was like, oh my God, this is amazing. What Polyvore does is it lets you mix and match and create outfits out of real products. And you can create those outfits and share them with your friends. It's kind of like a fashion magazine created by a community of women all over the world, but everything is shoppable. So I fell in love. I started using it two or three hours a night and just couldn't get it out of my brain. And then because I was a pm, I wrote. I had a lot of complaints about the product, so I wrote them all down and I sent an email to the co founder and one of the founders and I was like, hey, I love this product. I think it's going to be huge, but can you fix this, this, this, this, this? And here's some suggestions for how to fix them. And then he wrote back and said, hey, these are all great suggestions. Why don't you just come work here yourself and fix all this stuff yourself? And so that's what ended up happening and that's how I ended up at Polyvore.

So you filed a bug report and got them assigned to you?

Yeah, kind of.

Polyvore is fantastic and awful. My wife used to work at Polyvore, joined Polyvore for the same reason, because she needed to pay for all the stuff she was buying on Polyvore. So it's a very good site. So what was it about Polyvore that caught your interest when you were using it? What clicked? What made you so passionate about it?

So before getting into computer science and Google and all that, my original goal in life was to be a comic book artist because I really love to draw. That ended up not working out because my parents wouldn't let me go to art school because they're Asian. They thought it wasn't like a legitimate career. But what drew me into Polyvore was the ability to self express. I mean, it was a creative tool ultimately and it was kind of at the intersection of art and fashion and technology. So I thought, wow, how often does something like that happen where you pull together a lot of your passions? It's something that's at the very earliest stage. So if I went there, even though there's not a lot there, I would get the opportunity to learn a ton. Which actually reminded me of the APM program. I got into the APM program thinking like, okay, I don't know how to do. I don't even know what a PM is. But at least if I come here to Google, I'll grow and I'll learn and maybe it'll work, maybe it won't, but at least I would challenge myself and grow. And that's exactly how I felt about Polyver. There's nothing here. Maybe I can volunteer and step up and do some of those things and I'll grow a lot. And that's what ended up happening. I actually kept volunteering to do various different things at the company. I was like, oh, let me write the blog since we don't have a marketing person. Or let me answer the phone when the advertisers call because we don't have a sales team. And then what ended up happening is I would try that job, learn just enough to be a little bit dangerous, like just enough, and then figure out I wasn't very good at it, and then hire someone else to do it. But having done it myself, I was a little Bit better at finding the right person to hire. And then that person would inevitably end up reporting to me because I was the only sort of business person at the time. And then we just kept growing and eventually all the departments were reporting into me except for engineering, and my title was still VP of product. And at that point we decided to make the switch where I became CEO. So very unusual path to sort of running a company, but that was mine.

That's really interesting. And in that time, was there anything that you came across that you were like, no way. Never do this. Huge mistake, way too dangerous at this point?

Yeah, that was like, every day, I mean, startups are incredibly hard, right? Every day is a new obstacle. And I definitely felt like, especially since I was growing quickly and the company was growing every time I felt like, okay, I've got it now. I figured out how to do my job. I think I might have figured it out finally. That feeling would, like, inevitably only last for a brief moment because then the company would get bigger and then everything would change all over again. You people, you know, the process that was perfect for communicating with 20 people broke at 50 people. And then as we got that right, it broke again at 75, and then at 125. And then, you know, it's just things, when you're growing, things just keep changing. You just kind of have to get used to the feeling of constantly not knowing what you're doing or not not knowing how to do something, which is essentially the same thing as learning. So you should kind of seek. I've always felt like you should seek out that feeling. You should try to find that really nauseous, horrible feeling of, I don't know what I'm doing, because that's how you know you're getting career growth.

And then, was there anything while you were kind of the CEO of Polyvore that kept you up at night? I mean, what was your biggest worry while you were doing it?

Yeah, so specifically, I mean, there were so many things, you know, product, market fit, you know, was our product serving the users? Well, we were very, very community driven. And then figuring out, like, is the market that we're in big enough? Do we have to evolve the product? Lots of hiring, lots of the. Especially later, all the issues became very much related to, like, people. So did I have the right VP of sales? Did I have the right VP of engineering? Were these people clicking? I mean, there were so many moments and strangely, they all felt very existential because I think when you're the. When you're running the company, your identity becomes intertwined with the company's identity. And every bump in the road feels very, very personal, which is part of what makes startups so hard. Yeah.

So I was kind of stalking you on your Sequoia page before this, and you talk about grit a little bit. You talk about being able to create delight and overcome obstacles, just kind of sticking with it. I'm sure everything wasn't always, like, on the up and up. And it's a startup, so there's tons of times where you feel like you're dying.

Yeah.

So any advice for people in terms of developing grit? Is it something that's an eight and you just kind of have to express it, or is it something that you practice over time?

Yeah, I definitely think, you know, some people start out, there's this concept of distance traveled. Like when you're looking at, say, an interview candidate and you look at their resume, I think if you look at the distance traveled, like, where did they come from and how far have they gone? That's actually a good metric. That's how I really think about grit. Like, if you started at an easier place in life, like more privileged, maybe your distance, you know, your distance traveled might actually be less than someone who had none of the privilege. So I think sometimes your upbringing and where you came from, that original distance travel to get to where you are actually increases your grit sort of naturally. Like, could be your family circumstances, could be your socioeconomic classes. But on top of that, I think grit is something you actually develop over time. And the way you do that is you push yourself to travel further. You get used to just forcing yourself to do things that are hard, that feel bad, that nauseous feeling of learning that I was talking about. And that's actually what increases your grit, because grit is really. It's really pain tolerance. So if you can put yourself into those painful situations and those challenges, rather than kind of taking the easy route or coasting, that's, I think, how you develop grit. And I think grit is one of the most important ingredients in startup founders because it's just so hard. You don't control so many of your circumstance. Right. You don't control what happens with the market. You can't control the fundraising climate, you can't control what all the people on your team decide to do or if there's a competitor that comes along. So you really have to have grit. You have to practice at getting stronger and stronger to put up with all the ups and downs.

So is that something you look for now that you're on the other side of that funding table now that you're at Sequoia.

Yeah, absolutely. You know, I think a combination of grit and passion, right? Like, to get through the pain of just the basics of starting a company, you either have to really care about the problem and be mission oriented or you have to have that natural grit. But there has to be something driving you, right? Because on average, it takes, I think, eight or nine years to build a company.