In the latest episode of the “Taking Note” podcast, we sat down with Jess Lee, an Investing Partner at Sequoia Capital and former CEO of Polyvore, a popular style community that democratizes fashion and e-commerce. Jess discussed what she learned when starting her career at Google, how it helped her grow Polyvore, the challenges of innovation, why some companies are unable to cultivate good company culture, and why women in the tech industry are still struggling to get ahead. She also shares her methods for staying grounded and organized throughout her day (hint: it includes both handwritten notebooks and Evernote). Check it out:
Taking Note: Episode 9
In this episode:
- [1:20] What does Jess’s work week typically look like?
- [6:10] What skills from her time at Google did Jess bring to Polyvore?
- [7:20] What leadership lessons did Jess learn as Polyvore grew?
- [12:55] Jess is now in venture capital, why the shift?
- [14:55] What areas of innovation have Jess’s attention right now?
- [16:55] What are some of the biggest roadblocks to innovation?
- [20:40] About to start your first company? Build something useful and delightful.
- [22:25] Why is it still difficult for women to get ahead in the tech industry?
- [24:55] How can we fix toxic culture at work?
- [26:45] How does culture impact innovation and creativity?
- [28:45] As a VC, what does Jess look for in a company?
- [33:50] What is Jess’s daily routine?
- [36:10] How does Jess manage information overload?
You’ve had a fascinating, varied career, and it doesn’t follow the standard narrative. What are your core interests? What is it that drives you personally?
I think when I look back on all my career decisions, I’ve been primarily motivated by growth and learning. Basically, if I feel like my learning is plateauing, then it’s sort of time to do something different. That’s what’s driven me at all the major pivots in my career.
After [four years at Google], you wound up doing product management at Polyvore, which is a very interesting company.
Polyvore is a fashion community app, where basically you can mix and match all your favorite products in different stores into outfits or collages, and then millions of people come every month to browse and shop those looks.
When I first discovered Polyvore, it was just the outfit creation tool, and it was kind of like online Photoshop, but with shopping integrated, and it was super fun to play with. So I started playing with it all the time. I was using it maybe three or four hours a night, as a very addicted user. Then I wrote a note to the co-founders with a series of complaints and suggestions for how to make the product better. They wrote back and said, “Hey, why don’t you just work on this stuff yourself? Why don’t you just come join us?”
I ended up joining as the first PM, and that eventually grew into a co-founder role, strangely in reverse, and then eventually the CEO role. But part of the reason I went there was definitely because I felt like I would learn a lot, ’cause there were only three other people at the time.
Were there any specific things that happened at Polyvore which affected the way you view leadership?
I had never managed a single person before arriving at Polyvore. So I kind of had to learn it from scratch, on the job, through a lot of trial and error. You can read a lot about management best practices, but there’s no replacement for actually doing it.
“You can read a lot about managing best practices, but there’s no replacement for actually doing it.”
I think one of the biggest lessons for me was how to lead authentically. I tried for a while to copy different leadership styles that I had seen, especially very classic, extroverted leadership styles, which you see in the movies. Sort of like the War General.
It took me a while to figure out my style, because I’m more of an introvert. I was an inexperienced first-time CEO, so I couldn’t say with much authority, “I know exactly where we’re going,” exactly what we needed to do. I figured out eventually that, at the end of the day, you need your team to trust you, and to feel like they have a purpose and a mission. There’s an art to cultivating that, and I realized that rather than pretending that I knew everything all of the time, it’s actually better to just sort of point the ship in a general direction, say, “This is the destination I would like us to get to. It’s going to be bumpy along the way, and I need you, I need your help to get there.”
I was really inspired by Cheryl Dalrymple, who is the CFO that I eventually hired at Polyvore. When I first met her, I just remember being really blown away. She’s now the CFO at Confluent. She taught me that you can be a leader while still being very warm, and very authentic, a little quirky. People would follow her to the ends of the earth, and that’s something I took a lot of inspiration from.
After I met her and realized she had this quality, and I could learn a ton from her, I bent over backwards to just try to hire her, to try to get her to be an executive at Polyvore so that I could learn as much as possible from her.
That’s maybe another lesson, surround yourself with awesome people who you admire.
What are you most proud of, from your time at Polyvore?
I’m proud that we built a company that was profitable for three years. I’m proud of the impact we had on some of the users who would write in to say things like, “You gave me more confidence in life, because I figured out a style that worked for me. I felt better.” We even had one girl write in to say that she was inspired to study Computer Science by Polyvore. That was her admissions essay into Cornell, was about Polyvore. And that was a really proud moment.
I was really proud when we won “Great Places to Work.” We won in 2014, overall, for tech. And then in 2015, for best workplace for diversity and women. I’m proud of the culture and the team that we built.
You’ve moved from there into a new role in venture capital. What drove that move?
Part of it was definitely, again, maximizing for learning and growth. Investing is not something I’ve done before, and that’s the best way to learn, is to do something you haven’t done before. On top of that I thought, “How do I leverage the eight and a half years of lessons from Polyvore, through all the epic highs and epic lows, the ups and downs?” Some of those lessons were really painful. “How do I leverage that, and make a big impact?”
I thought if I could help the next generation of entrepreneurs and founders, and help them maybe shave off a day here, not make a mistake that I made, or just advise a little bit, and then spread out that help across the portfolio companies, that I would feel great about that.
Also, there aren’t a lot of women in venture, and I think that ends up impacting the number of women who get funded. That impacts women executives, and then eventually, the percentage of women in engineering. It all trickles down and I thought, maybe I can make an impact there, as well.
Working with Sequoia, I’m sure you’re seeing a lot of very interesting pitches coming your way, you’re involved with a lot of interesting companies. What areas of innovation are particularly exciting to you right now?
There are so many. I have been spending most of my time in consumer, but that doesn’t just mean consumer, internet and mobile. I’ve also started to look a little bit at consumer use cases in robotics, in direct-to-consumer brands, in AR and VR … there’s a lot going on. That’s been exciting.
I feel like I’m seeing a big trend towards tech moving out of your devices and into the real world, whether that’s home automation, or tech-enabled commerce, or tech impacting the way we work on a day-to-day basis. I think that’s one of the more interesting trends. I’m seeing a lot of activity, and I expect to see a lot more.
What do you think are the biggest roadblocks to innovation within companies today?
I think companies can get addicted to their own success, and then start to fear jeopardizing it, or feel like if they step away from that core business, that something might go wrong. So I think the best way to get around that is to dedicate an entire team whose job is to just think about what’s new. You kind of want to create a little bit of separation.
We did a little bit of this after Polyvore was acquired by Yahoo. We took a portion of the Polyvore team, and got them staffed to just work on completely brand-new ideas in the lifestyle space. While we were there, we actually shipped maybe five or six prototypes of apps that we were able to brainstorm and build in, I think around seven weeks turnaround time, from inception and brainstorming to putting them in the App Store.
We were able to test quite a few ideas. One of which eventually turned into Cabana, by Tumblr, which is a live streaming app that the Polyvore team worked on.
It sounds like a good approach to fighting that fear of change that can become ingrained in a large company. There’s also, I think in a large company, that problem of, once something’s that large, it’s hard to turn the ship. Is there a way to fight that sort of inertia?
I think part of it also comes from setting the tone of the culture at the very top. Companies that are able to reinvent and reinvigorate are the ones that are a little bit paranoid and have a really, really high bar. If you know from the get-go that you’re a consumer company… it depends on the product, exactly, but for some consumer-use cases, like social communication, a lot of that is driven not just by the utility or the functionality of the product, but also by how cool it is.
“Companies that are able to reinvent are the ones that are a little bit paranoid and have a really, really high bar.”
So, if you accept that you’re on this treadmill of cool, which is definitely the case for some hardware, some communication apps. I think Apple gets that. I think Snapchat gets that. So they hold the bar very high, and even though they’re doing well, they still feel this urge to reinvent and raise the bar higher and come up with the next thing, or the next feature. I think that’s baked into cultures, at the very highest levels.
When we’re talking about little companies, startups or individual entrepreneurs … of course, the fact that they can pursue the cool is their advantage, but it can also be a downfall. Maybe it’s hard to know when an idea is worth pursuing. When do you think is the right time to jump on an idea?
You know it’s good when people start to tell each other about it. You find this kernel of delight. And delight isn’t just, “Yes, this was useful.” It was a moment of, “Wow, that was cool.” And then the notion that you might want to tell someone else about it. That’s what leads to word-of-mouth, that’s what leads to growth, and that’s how you know that something is worth pursuing.
What would your advice be for someone who’s maybe thinking of starting their first company?
Build something useful and delightful, might be the first one. Second, just understand that great companies take, usually, a while to grow. There’s no real overnight success. Polyvore was an eight-and-a-half year journey, and I think our acquisition by Yahoo was seven and a half years in. But the average exit time for a successful startup is eight years. So, pick an idea and a co-founder that you’d be excited to be married to for at least eight years. That would be my advice.
I want to dig a little deeper into some of the issues of leadership and culture that you brought up earlier. In particular, you mentioned that one of the things that inspires you in your role now as a VC is the opportunity to help more women get involved in engineering, in company-building, in all of those fields.
This is a part of the world that still, I think, has a very male-dominated culture. There are lots of women working [in the field], but it seems like almost every month, there’s another story about how it’s still difficult for women to make an impact in the world of tech and get ahead. Why is this still a problem?
Part of it, I think, is the ratio. But part of it has been, up till now, kind of a lack of recognition that it is a problem. I think what’s the good part of all the news that’s come to light lately is, people were talking about it now. And also, it reflects a change in the norms, in that when someone comes forward, it’s no longer the norm that her career is destroyed … I think that was more the norm, before. So just the shift that’s been happening over the last few months represents a change.
I think now that the news is starting to come out, people are realizing, “Oh wow, this was happening all along. This is happening in my organization, I’ve just been unconscious of it the entire time.” But now that that recognition is happening, that’s when change can begin.
This intersects with other areas of culture, and we’ve had some prominent examples where culture can just go toxic. When that happens, it doesn’t just necessarily affect the company itself. It can also affect the economy at large.
I think about some of the more prominent cases lately of toxic culture, and these are sometimes some very large companies that are very disruptive in their space, and that are considered real trendsetters. If they can’t get it together, what does that mean for tech as a whole?
Startups go through all kinds of ups and downs, and culture can be your lifesaver when you’re in the downs. When you’re no longer winning, and crushing it, and going “up and to the right,” and there are issues, people flee your company. They will flee if your culture is bad, because that was part of what was making them unhappy all along. But they’re willing to put up with it to be part of a winning team. And as soon as you’re no longer winning, they leave.
I think culture is something you entirely control, as a founder within your company. You are the person who sets the example, you hire the people. It’s something entirely within your control, unlike economy or the market or competitors, which are all risks to your startup. So there’s really no excuse for getting it right, because you entirely control it. And the benefit of getting it right is whenever you hit a bump in the road, your team is much more likely to be loyal, and to believe, and to want to stick around to fight the battle, if they love the culture and they love the team.
So, culture is something you should absolutely invest in, unless you plan to be winning 100% of the time, which is impossible, as has been shown by all the latest news. It’s just not possible to win all the time.
How does culture impact innovation and creativity, and how did you foster innovation and creativity when you were at Polyvore?
At Polyvore, our three core values were, “Delight the user,” “Do a few things well,” and, “Make an impact.” For every new person who joined the company, day one on orientation, I would walk them through … probably the first meeting of the day, after they signed their papers, was to meet with me and I would walk them through those three values and what they meant with quite a lot of detail into the examples.
The bulk of orientation was culture, and then part of it after, we went into the product and the strategy and the users. But I felt like hearing from me as the CEO what the culture meant, and how to live it, was actually a really strong indicator that the culture’s really important. It was also an opportunity to ask questions about it, and to understand it. That’s part of how I tried to make sure the culture permeated through the company.
In terms of innovation, “Delight the user,” going back to that one, the first value, I would explain kind of what I talked about earlier. How you have to constantly raise the bar, and not just build a functional product, but a functional and delightful product. You would constantly have to top yourself.
I would give examples. I used Apple as an example of how people think they want a better, faster horse, but really what they want is a car. And they’re not going to tell you, if they’ve only ever seen a horse, that they need a car. So you have to come up with it.
And then, even when you build that car and people are really happy with it, then you have to come up with the rocket, a spaceship, whatever’s next.
It sounds like the concept of being functional and delightful applies externally, in terms of the product you build, but also applies internally, in terms of the culture you build.
How about now that you’re on the VC side? What do you look for in a healthy company?
I think there are some classic things that pretty much all VC’s look for, like a very large market, a founding team that’s capable. For me, personally, a few additional things that I look for are grit… because, like I said, it takes a really long time to build a great company, and you want someone who can weather the storms, who can go through the ups and downs. So, I look for grit.
Another trait I find quite useful is the ability to take something complex, and explain it simply. That applies to so many things. It’s your elevator pitch when you’re talking to investors, it becomes important. Your ability to communicate to your team, and even more important than that though, to be able to run an all-hands and explain to your team where you’re going and how you’re going to get there. All of that is really, really important. So, I look for the ability to explain complex things simply.
Is there one particular skill that you wish every businessperson would learn?
Maybe empathy. The ability to understand something from someone else’s perspective. Whether that’s a coworker or an employee, or even your customers, that’s a pretty useful skill.
We’ve talked a lot about culture and working effectively as a team. How about working effectively as an individual? How do you manage your very busy time?
I take a lot of notes on everything, to be honest. They may not always be the most organized of notes, but I do find it’s important to capture the information. I can always go back later and make sense of it, but it’s helpful to have it there so that I can even try to retrieve it in the first place.
I take a lot of notes on everything, to be honest. They may not always be the most organized of notes, but I do find it’s important to capture the information.
I do it both on my computer and Evernote, as well as… since I love to draw, I always have a small sketchbook with me, and a pen. So, I’ll take notes on paper as well. And then I take photos of it using Evernote’s capture feature, and then store it in Evernote so that it’s searchable later.
I know a lot of people who are into that visual note-taking approach, the sketch notes idea. Do you have a particular way you like to do it? Is there a format? Do you have a shorthand of visual symbols?
No, it’s not particularly organized. They look probably like doodles.
I find that what I’ll do is, I’ll just take notes during a meeting, and then later I’ll go back and kind of draw and organize them at the same time … create dividers, draw in little pictures, sort of summarize, and then the key things jump out at me later when I go back to look at them. Key numbers, sometimes I’ll draw a little picture to indicate something that was important.
So notes are a cornerstone of how you manage your time. Is there anything else that you use? Do you have a particular toolkit?
I think it’s really just document everything. And then, for the key things that I have to do every week, that I cannot miss, which is basically keeping up-to-date and communicating with companies that we might want to invest in, or might be passing on … keeping a running list of those, and making sure that those really, really important to-do’s get done.
I feel like my brain is not particularly organized, kind of like a black box. And then, occasionally, connections will spark, and I’ll come to some sort of Eureka moment about a company, or a trend, or an idea that I want to go back on, and then I have it all there at my fingertips in Evernote, so I can go back and search for it.
That’s what creativity and innovation are, really, isn’t it? It’s making those connections. It’s finding those moments of spark between the things that you’ve already collected and just drawing that new link.
There are so many inputs in our world, and in our lives. We’re constantly getting messages from all sorts of different apps and media and we’re expected to deal with it all. “Information Overload” is not a new term, that’s been around for decades, but it’s still very much with us. How do you manage it?
I try to clear the slate in my brain as well. If something is not immediately important, I just kind of tuck it away, and hopefully that black box brings it up at the right moment, the random spark of connection. But I think it’s important to keep the slate clean. I find that yoga helps clearing the slate as well, so that’s something small that I do.
This is a partial transcript of our interview. For the rest, be sure to listen to the complete podcast.
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