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Jess Lee: “Partner at Sequoia Capital and Former CEO” | Talks at Google

Jess Lee: “Partner at Sequoia Capital and Former CEO” | Talks at Google


DAN CAREY: So today,
welcome to this Talk at Google with Jess Lee. I’m Dan Carey, and
joining me is Jess. JESS LEE: Hi. DAN CAREY: She is a
partner at Sequoia Capital. Previously she was at
Google as a product manager, and then Polyvore– Polyvore. She 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, Glamour’s top 35 Under 35 Women in Tech, and a
whole bunch of other things. So welcome. Thanks for coming. JESS LEE: Yeah,
thanks for having me. [APPLAUSE] Oh, thank you. DAN CAREY: So what’s it
like to be back at Google? JESS LEE: Oh, it’s totally– DAN CAREY: Is it wild? JESS LEE: It’s trippy. It’s very surreal. I used to sit in this
building in 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 Froogle, which was product search back in the day. And then, after a short stint
there, 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. DAN CAREY: So you joined
Polyvore right from Google, right? JESS LEE: Yeah. DAN CAREY: And it was kind
of a weird journey, right? Like, it wasn’t
normal circumstances for leaving Google
and joining a company. JESS LEE: 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, OK. 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 shopable. 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 one of the founders,
and I was like, hey, I love his product, I think
it’s going to be huge, but can you fix this,
this, this, this, this, and here are 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. DAN CAREY: So you
filed a bug report and got them assigned to you? JESS LEE: Yeah, kind of. DAN CAREY: Polyvore is
fantastic and awful. My wife used to work
at Polyvore and 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? JESS LEE: 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 loved to draw. That ended up not working out,
because my parents wouldn’t let me go to art school
because they’re Asian and they thought it wasn’t
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
it pulls 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, OK, 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 Polyvore. I was like, 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. You know, I was like, well,
let me write the blogs, since I’m 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 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 in to 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. DAN CAREY: That’s
really interesting. And in that time,
was there anything that you came across that
you were like no way, I can ever do this, huge
mistake, way too dangerous at this? JESS LEE: Yeah, that
was like every day. I mean, startups
are incredibly hard. 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, OK,
I’ve got it now, I’ve figured out
how to do my job, I think I might have
figured it out finally, that feeling would inevitably
only last for a brief moment, because then the
company would get bigger and then everything would
change all over again, new 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,
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 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. DAN CAREY: 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 that? JESS LEE: Oh, yeah. So specifically– I mean,
there were so many things. Product market fit. Was our product
serving the users well? We were very, very
community driven. And then figuring
out 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 of the issues became very much
related to 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 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. DAN CAREY: 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 on the up and up, and it’s a startup,
so there tons of times where you feel like dying. JESS LEE: Yeah. DAN CAREY: So any
advice for people in terms of developing grit? Is it something that’s innate
and you just kind of have to express it, or
is it something that you practice over time? JESS LEE: 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, and then 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. If you started at an easier
place in life, more privileged, maybe 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 traveled to get to where
you are, actually increases your grit sort of naturally. It could be your
family circumstances. It 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 circumstances, or 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 need to practice at getting
stronger and stronger to put up with all the ups and downs. DAN CAREY: 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? JESS LEE: Yeah, absolutely. You know, I think a combination
of grit and passion. 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, because, on average,
it takes, I think, eight or nine years to build
a company from ground zero to a successful outcome, like
an [INAUDIBLE] or a large M&A. And so, you know, imagining
that amount of time, it has to be something
you probably care about. You need the grit to power
through all the problems. DAN CAREY: Yeah. One of the other things that
you mention on your Sequoia profile and a few
other interviews that I’ve seen with
you is you talk about focusing on one thing and
doing it really, really well. JESS LEE: Yeah. That was one of the core
value at Polyvore, yeah. DAN CAREY: Do one thing. JESS LEE: Mm-hmm. DAN CAREY: So how has that
one thing kind of changed? I’m sure being a wannabe
comic book artist, being an APM at Google,
being at Polyvore in all those different
roles, it’s changed a lot. How do you kind of
pick that one thing? JESS LEE: Yeah. I think when I was a
PM, one of my strengths was actually
empathy, it was being able to think what does the
user want in this situation? As they’re printing out their
driving directions before– on Google Maps back when we used
to print driving directions, because remember,
this is desktop days, what are they thinking? What do they want? And that empathy helped guide
a lot of product decisions. But then as you become– then I became– I transitioned,
and at Polyvore I started answering the
phones for sales calls. Then the empathy
was applied to what does the advertiser want,
and trying to research and understand enough about
the advertising industry to imagine, OK, it’s not
just this is an advertiser. The person that I am talking
to is an account manager at a large agency who is
trying to advance their career and wants to do good
for this client. The client probably
thinks this way. And being able to
take all of that and figure out what the
right ad product was. Then, as the company got large
and I started managing people, it was what does
my team care about? Where is this person
in their career? How do they feel about the
current state of the company, their team, their career goals? And now that I’m
investor side, again that applies to trying to
understand the founder. And then trying to understand
the market that they’re in, the users that they’re serving,
what do they care about. So I would say that first I
thought, oh, my one skill is actually product design
and product manager, and then I looked
a little bit deeper and I realized it was probably
something to do with empathy. DAN CAREY: Do you
think that’s just the key for consumer
businesses is empathy kind of across the board? Is that the thing to nail? JESS LEE: Not
necessarily, because I think with the help of
amazing user researchers who can tell you these are your
three personas of, you know, the three types of users that
you’re solving for, you can actually– if you’re an
analytical, smart person, if you have that
data given to you, rather than having
to imagine it, you can still be a
fantastic product designer. I think the key
with great consumer design, product design, is
creating a kernel of delight. It’s not enough to have a
product that solves a problem and sort of does what
people ask you for. You have to go way
above and beyond. And there has to be this moment
of, whoa, I didn’t expect that, or that was amazing or
unexpected, to the point where you would bother
to tell a friend. A good example is
actually Snapchat. When you take your– when you do the filters and you
do one that’s the face swap. That’s really clever
because I didn’t expect that inside some sort of chat app. And then, it’s inherently viral. I will sit there and
show it to my friend, and we’ll do it together. And that’s a moment of
word of mouth delight. So I think the secret to
great consumer products is you have to grow. And if you’re
growing organically, it’s because people
are talking about you. And the way to get people
to talk about your product is to do something above and
beyond that’s really, really delightful. So that’s how I think about it. DAN CAREY: So what do you
think the most important thing was that you worked at
while you were at Polyvore? And I’m wondering if you
knew how important it was at the time. JESS LEE: Yeah, I
don’t think I did, but it turned out to be culture. In the beginning,
when you’re starting, the product you build
as a CEO, as a founder, is the product, the service
that is delivered to your users. But then as the company
grows, your attention actually– you get further and
further away from the product, because you’re not the one
writing the code anymore, or you’re not the one making
the day-to-day decisions, you’re managing through a team. And the product actually
starts to become the company and the organization. And the same way that you
instrument your product and measure is this
feature working or not, your AB test, or you carefully– you know, you put Google
Analytics on everything. You actually have
to do the same thing with your company and your
team to make sure it’s healthy. Like are you measuring your
employee engagement scores? Are people happy and thriving? Is code being checked? And you actually have to
pay a lot of attention to how people work together. And, most importantly,
the culture is basically the
operating system. So it’s about
building the operating system for the company,
which is the culture, and then all those metrics
and things that you monitor. And the larger and
larger you get, the more and more
important it becomes, because you need people to
be aligned on how to behave. And that’s something
I’ve always thought was really great about Google. I always felt like there was a
clear culture when I was here, and it was measured and
defined and really cared about and thrived, and everyone
knew what being Googley meant. And I think that’s part
of why Google has always been successful. DAN CAREY: So did you
just fork Google culture and bring it over to Polyvore? JESS LEE: No, actually. I had made some– a lot of it’s the same,
like empowering engineers to make decisions,
empowering product people and try to be a little bit more
bottoms up, or at least that’s how it felt when I was here. I copied a lot of that. But the one thing
I did not copy, and I think you can’t
at a startup, is you have to be very cognizant
that you’re on a clock and you’re running out
of money all the time. Google has one of the best
business models in the world, and basically
AdWords and AdSense are printing money
in the basement to power all kinds
of amazing projects. Now that’s evolved to Android
or maybe other business lines, but that luxury of, oh,
we need to just purely focus on building
the right product and not have to worry too
much about revenue, which is the case– it’s probably
changed since then, but that was certainly
the case when I was here. I could not copy that
over into a startup where you have 24
months of runway. And it’s not even just the
runway of money you’re funding. It’s also the runway of
people’s time and patience. If you’re underpaying your
team, because they’re not at Google or Facebook,
then you have to make sure they see a path to success. So I think being much more
conscious about spend as well as urgency and people’s time
was a big part of our culture that I would say was
different than Google. DAN CAREY: So a couple things
I keep hearing is learning, people, caring. Are these the things
that motivated you? Has your motivation been
the same across an APM, being a CEO, being at
Yahoo, being at Sequoia? JESS LEE: Personal motivation. I think I care about two things. One is impact. Like what kind of
impact are you leaving? What sort of dent are
you making universe? And the second is just
personal growth and learning. I found that if, again, if
you optimize for learning, then you think about success
and failure in a different way, because sometimes you learn
the most in the toughest situations where you
are most likely to fail. So if you reframe that
conversation into am I learning or not learning, and
learning is success, then you stop thinking
about whether you’re getting the A or
the C or whether you sold for a billion dollars
or a hundred million. You just stop thinking purely
about the outcome, which makes you afraid sometimes,
because you don’t want to risk what you already have. And then the other is impact. One of the things that I
really loved about Polyvore was it had this very
democratizing effect on fashion. It was about letting
a community of women all around the
world say, no, this is what I think is
stylish, and I don’t want to listen to the fashion
magazines telling me this is what you’re
supposed to look like. And, for the women who used
it, it was very empowering, and that allowed
them to– you know, when you feel like you
look a little better, then you might feel a
little bit more confident. And we had so many
girls from school age to girls applying to college,
to older women, just talking about how it helped
their confidence. So, for me, that was always
was part of the mission. And then part of the
mission, for me, at Sequoia is– you know, the venture
is probably 7% women. And that, I think,
has downstream impacts on the percent of women
who start companies and the percent of
innovation that happens in fields targeted at women. And then that affects execs
and all the way down the chain. So I thought maybe if I
could move into venture and change the ratio
just a little bit and help back amazing
founders, both men and women, but I might be a little bit
more inclined to understand some of the female
founders who are working on products targeted at women,
which I was at one point too. So that’s on the impact side. DAN CAREY: So how are
you approaching your role as a partner at Sequoia now? I know it’s still relatively
new, but anything where you’re like, this is what
I’m going to do, I’m going to be
focused on this, I’m going to provide
this value to people? JESS LEE: Yeah. So I think the investors
that do the best are probably the ones that are actually
helpful to their founders. So I’ve tried to focus on
where can I be really helpful. And some of those
areas are in consumer, because that was what I did. My whole career has
been mostly in consumer. I’m also starting to look at
some spaces like AR and VR and robotics. I spend a lot of time meeting
female founders as well. I’ve been looking at
direct-to-consumer brands, which is fairly new for
venture and for Sequoia. Yeah, those are some of the
areas that I tend to focus on. DAN CAREY: And any
kind of niche fields that you’re kind of geeking
out about, excited about? JESS LEE: I’m pretty
excited about robotics. I think now that computer vision
is of age, computers can see, you’re seeing a lot more
tech moving out of the phone. Instead of it being in a little
screen or on your desktop, it’s moving out into
the physical world. And maybe the first– basically it’s sort of
the intersection of it’s all the tech that we know
from the internet moving from pure bits into
the world of atoms. So maybe the earliest
version of this might be something like
DoorDash or Instacart or Google Shopping Express
where it’s not just software and are my bugs OK? It’s like software
and then, oh my god, all the problems of the
real world, like the driver was drunk or missed the
delivery, or the food’s cold. These are not
things that software can catch, which is why I
think a lot of these companies are run by hardcore operational
people who just know how to grind it out and
have a lot of grit, because it’s not beautiful,
elegant software anymore. And I think you’re going to
see more and more of that as we move into
fields like robotics and more automation
in the real world. DAN CAREY: You
realize that now you have to combine
fashion and robotics, and I guess Google Maps now. JESS LEE: Yeah, I have
not seen that pitch yet, but that would be pretty cool. DAN CAREY: I’m sure
it will come up. So before I ask you about
the most important thing that you’re working
on at Polyvore, but what’s the most
important thing that you’re working on today, if
you’re aware of it? JESS LEE: The most
important thing. I think, at the end of
the day, Sequoia’s mission is to help daring founders build
really legendary companies. So the most important thing
is to find those people and help them. I have done two investments. I spent a lot of time
with those founders. One is a seed. One is a Series B. Because
I’m on the early-stage team. We do everything from seed to
basically Series B. Every day is just trying to figure
out how to help them. And then the other piece
is I’ve been working on various initiatives to
try to figure out how to help female founders more so. There’ll be more on that
probably in a few weeks. DAN CAREY: OK. Yeah, I know you’ve been
doing a lot of talks lately. A conference a couple of
weeks ago for women in tech. JESS LEE: Yeah, yeah. I love going to those events. It’s so amazing to see all the
activity and the excitement. DAN CAREY: So when you were
running a startup, when you were talking about
product market fit, how did you know
when you nailed it? I mean, delight won’t give
you product market fit, it will give you virality. How do you know
that you’re actually providing that value early on? JESS LEE: So I actually do think
that when you found delight and you found product
market fit that you do start to see organic growth. You do start to see
that word of mouth. You’re right, there
are moments where you’re seeing that word of
mouth for other reasons, like maybe you had a really
viral piece of content on your platform. So you have to be able to figure
out how to distinguish that. But, generally, I think organic
growth means that you’ve found product market fit. The question, though,
is how large of a market is it that you’re working
on, and how– you know, you can have product market
fit for some very tiny sliver of a market or for
a particular user, and you have to be
able to distinguish is this enough for a
sustainable company or not. I mean, I think that’s the
biggest lesson that I’ve learned on the venture side. I can assess the match between
maybe a user and a product, but thinking through the
market structure, like is this a good market to be in? Are there tons and
tons of competitors? Are the platform companies
most likely going to dominate the space
in the long run, and, therefore, your tech
will be commoditized? Thinking through those kinds
of issues in market size and market structure
has sort of been one of the biggest lessons. DAN CAREY: Any tips
for learning that stuff other than joining a
VC firm and thinking about it 40 or 80 hours a week? JESS LEE: Yeah. I think– this is
maybe something I didn’t do enough of as a
PM, is competitive analysis. Look through what other people– you should obviously
figure out what’s great about your product,
but you also have to think– when I say delight, when
you’re going above and beyond what people expect. What people expect is set by
what’s available in the market. So just because you solved
their problem doesn’t mean you’re going to win if
there’s another product that also solves their problem but
has much better distribution than you do. So you really have to think
about that line of what people expect being set
partly by competitors. A good example of this is when
all the smartphones came out. Before that, BlackBerry
was the best phone. It had a keyboard. You could your email. And then when the iPhone
came out, that was just– I don’t need a keyboard, like
I can browse the entire web with this. It just reset
everyone’s expectations. And it took– a lot of companies
died during that because they didn’t catch up and
they were just focused on what they were doing. You have to think about who
else is innovating out there, and what are they doing. So I would say spending a lot
of time on competitive analysis. And then also thinking through
here’s where we are now, where will we be in five years? Where will my competitors
be in five years? And then skate towards that. You know, skate to
where the puck is going, not to where it is right now. So just getting really good
at thinking about that is, I think, the most
important thing. DAN CAREY: And I’m guessing
that advice holds true for CEOs, for basically everybody? JESS LEE: Yes. DAN CAREY: OK. JESS LEE: I think that matters
a lot for founders and CEOs as well. DAN CAREY: Does
stage matter there? Should early-stage
startup founders be worrying about
their competitors, or should they just be
focused on delight and value, like you said? JESS LEE: I think you still
have to think about it. It’s not something you spend
every day obsessing about. I don’t think you can be
constantly looking behind you, looking in the rear
mirror, but you have to know what
the baseline is, and you have to have a sense. And that’s part of how
you set your strategy. And then you just focus
on getting to that point. But you have to make sure do
those checks periodically. It could be once a
year, if you’re smaller. It could be every
quarter, if you’re larger. But it is really
important to have that, to check the expectations of
the market on a regular basis but focus most of your
time on actual execution. DAN CAREY: I’m
really curious what you think about the early
stages of community. Obviously, Polyvore had
a really good community. It had a good company culture. Do you see differences between
how you seed culture internally at a company and how you
seed it in a product? JESS LEE: I think it’s
best if they’re somewhat aligned, because, if they
are, then I think it comes across more authentically. For the community, what we did
is the same way that we cared about our individual employees,
we cared about our community. When we would have
a community event, we would apply– do
a few things well, rather than having
a massive conference where we couldn’t really
spend time with people, and we also didn’t have
the money for that, we chose to have
smaller meetups. So we got 20 people to come to
New York Fashion Week with us, and we threw a beautiful
breakfast for them. We took a couple of
them to some shows. We tried to give them the
tickets, instead of us going. Our community manager went
through all their Polyvore profiles and picked
out items that– products that they had used
regularly and then bought them. We got our advertisers
to just give us swag, free stuff and coupons
and shoes or whatever. We packed them into these bags. And I remember we
had these breakfasts, and some of these women
would open it and just start crying because
they were so happy. It was just the immense
delight was amazing, and it was just such a bonding
moment for those teams. And then they went on to
talk to the other community members about it. So it was great for us. It’s hard to measure
whether that was really an ROI-positive investment,
which is sometimes how people think about
community, but I think that’s just not the right
way to think about it. Think about Zappos. Zappos has an
amazing reputation, and that’s because of good
customer service, but also those stories of the woman
who wrote in or was on a call with a Zappos person for
an hour talking about how she had a whole
series of life events and therefore needed
to return the shoes, and they’d let her
return it and then they counseled her for an hour
and then gave her something– I don’t know. I don’t even remember
the lore anymore. But that’s the point. All I remember is there was
a story, and it was amazing, and that’s part of
what cemented, I think, the brand for Zappos. DAN CAREY: Do you think
people are focusing, founders, as much as they
should, on culture today? Do you see a lot of these
really big, scalable networks that don’t really have
an identity to them? JESS LEE: Yeah. I think sometimes it’s easy to
just be obsessed with winning and not think about culture. And that’s fine if
you’re always winning. People love to work at
companies that are winning. That’s a huge part of it. You can’t just have
an amazing culture and then drive your
company into the ground. You have to have both. But I think some companies
have prioritized winning over treating people well. And that works as long as you’re
on that upward trajectory, but as soon as the
going gets tough, I think people start to
look around and question, and they’re like,
why am I here again? I’m being treated horribly. And then they start to bail. So part of culture and creating
that right operating system is it smooths out the
bumps in the road, because when the
going gets tough, which it almost always
does at a startup, there’s always going to be
something that goes wrong, you get to keep your team
together for just a little bit longer. They have a little bit
more loyalty, a little bit more patience, and that
extends that runway that I was talking about. Because it’s not just
a runway of money and not being able
to pay people, it’s a runway of
people’s patience. As an employee, you
have a million things to choose as a job. If you’re great, you
can come work at Google, you can work at Facebook, and
then you get paid more too, but they choose to
work at your startup, and you have to
figure out how do you get that little bit
of extra loyalty when the going gets tough. So I think culture
is very important. I think, in general,
Silicon Valley does really focus on culture. And every kind of culture. You know, there are
eccentric cultures. It can be extreme, that’s fine. Yeah. But I think treating
employees right is really, really important. DAN CAREY: So if
you weren’t in tech, let’s say you’re not
at Sequoia, let’s say you’re banned from the
tech industry forever, are you going to go become
a comic book artist? What would you do? JESS LEE: That’s
a good question. I don’t think I would make
it as a comic book artist. I don’t think I’m
talented enough. But I might give
it a try anyway. Yeah, or a
professional cosplayer. DAN CAREY: Oh really? JESS LEE: Yeah. DAN CAREY: Can we touch on that? Because that’s divergent. JESS LEE: Yeah. Well, I love anime, and I
cosplay now, rarely, but, yeah. DAN CAREY: That’s pretty fun. JESS LEE: Yeah. DAN CAREY: So you were at
Yahoo for a bit of time. You were at Polyvore
for a very long time. You were at Google
for a bit of time. Those are three companies in
relatively similar spaces, or at least parts of them. What was it like working
across them over time? Did you have to adapt yourself
to provide the most value and provide the most
impact, or was it more of this is what
you bring to the table, here’s how you can influence
the group around you? JESS LEE: Oh, it change a lot. At Google I was an APM,
fresh out of Stanford, computer science. I had never led a team before. I had no idea what I was doing. I never had a real job. And you come into that
situation with a bunch of experienced
engineers, and you’re like, how do I get these
people to listen to me at all? I have no credibility. So there, I
remember, I was like, how do I get them to respect me? I know, I’ll fix a bug. So I just checked
in code and tried to prove that I was useful and
that I was going to work hard, and slowly built that
relationship with that team. But it was all about
rolling up your sleeves and getting stuff done. Then when I had
the credibility, I was able to lay out more
of the product roadmap. But everything was
very, very in the weeds and working with the team,
making decisions myself. At Polyvore, it was,
early days, very similar. I mean, they hired
me and I didn’t have to work so hard
to earn the respect, but it was a lot of in the
weeds and making decisions, writing code, all that stuff. Then when you switch into
becoming a manager or VP or moving up in the
org, you are no longer focused on the solution. You are focused on the problem. And the art– I think the reason
why no one likes mic– no one really likes
micromanagers. What’s annoying is that the
micromanager is a person who is trying to tell you,
here’s the solution, let me tell you, like, do
it this way, do it my way. And what you really want is
an explanation of, like, no, this is the problem
we’re trying to solve. The reason I don’t
like your solution is because you didn’t think
about this part of the problem. So if you just articulate
the problem clearly and the guardrails of
what’s acceptable and not, then people start to come
up with the solutions that are a little bit closer to
what maybe you think is ideal. And even they don’t, you have
to still accept it sometimes, because they could
be totally right. I’ve been proven wrong
many, many times, as I’m sure we all
have, if we’re managers. But that just keeps changing
as you grow in the org. So you start with
a solution creator, then you become a
problem creator. And then at some point,
no one tells you anything. There’s no problem given
to you and you don’t have to articulate, you’re just– here, you are a VP at Yahoo,
create value for our company. And then no one tells you– you know, so we
invented products. So that’s a very
different way of thinking. But I would say that that was
the difference between all the different roles and stages. DAN CAREY: So did you
approach that by trying to find problems for people, or
did you just try to find teams and then say, bring me problems
you think are important? JESS LEE: Yeah, so I set
up a very– you know, I was a VP of the
lifestyle group. And we knew that
to create value, we wanted to build a bigger
mobile user base for Yahoo, because it was still quite a
home-page, desktop-centric. I actually had a lot of– Yahoo Weather is amazing, but
still, more mobile growth. And we wanted lifestyle,
which, to me, meant a younger audience and a lot of women. So then what we
did is we started outlining what are the
verticals that we could go into? Health and wellness. Fashion. Beauty. Social. And so we picked verticals. And then what we
did is we started to build out user personas. What are the different types
of people in this space? And then what are the problems? And what I did was I didn’t
tell them, here are the people, I know exactly what
women 13 to 25 want. I said, here are the
parameters of those users. Come up with a process to
understand these people. And then the team got
really good at that. They got great at
creating user personas. They became amazing at
coming up with a brainstorm. Erica was involved in
this, actually, your wife. She’s awesome. And they would– DAN CAREY: I know. JESS LEE: — run a process
with the team to brainstorm different products. And then we came up
with a process for how to test that very quickly. And then what we
ended up doing is creating a process to get
apps shipped in eight weeks. So we would brainstorm, and
then eight weeks later, we would push something to Android. And it would be an MVP,
but we’d get enough data. And then we’d do two or
three more iterations. And there, we
actually shipped, I think, four or five apps inside
of Yahoo under some umbrella company so it didn’t
say Yahoo on it, because we didn’t want
to risk the brand. But it was a great, fun thing
for the team to work on. For various reasons– well,
we didn’t ship all of them. You know, some of
them actually sucked. And some of them had
interesting traction, but we ended up deciding
they weren’t strategic. And the one that
eventually launched was Cabana by Tumblr, which is
a live-streaming, group-watching app. You know, I think there’s
a lot more work to be done, but I think– that’s sort of how we
managed that process, or how I managed it as
the VP without– while wanting to empower the
team but also making sure we were doing something useful
and strategic for Yahoo. DAN CAREY: It’s
really interesting. JESS LEE: Yeah. And these were teams
of five people– no, six. Three or four engineers and
then a designer and a PM, so a very small
team, eight weeks. DAN CAREY: We do have a
Dory with some questions, and we also have
a mic in the back. So the Dory link, for
anyone on the livestream, is go/ask-jesslee. But why don’t we bring this
up and take a few of these. OK, so what’s the difference
between being a PM at Google and being a CEO at a startup? And, in your case, did
you see any challenges during that transition, and
how did you get over them? JESS LEE: Yeah, so I
think I’ve mentioned some of that, the culture
and the environment in terms of having to
think through revenue very early on was different. You know, at Google,
the responsibility was much more about
the product and less about the people and the org, or
the product became the company at the CEO stage. It was a challenging transition. Like I said, I constantly
felt like I didn’t really know what I was doing,
and the job just kept evolving underneath
me, then I’d figure it out and then it would change again. DAN CAREY: So you’ve been on
both building and financing side of products and businesses,
so which would you pick? JESS LEE: Oh, that’s
a tough question. There are pros and cons to each. On the building side,
as a founder and a CEO, there’s a lot of existential
stress, because you become– your identity
becomes the company, and you’re constantly worried
about are we going to make it? You know, I’ve brought 125
people with me on this journey, what am I– you
know, is this going to work out for all of us? So it’s much more existentially
stressful than being on the investor side where
the value of your work is spread out across a portfolio
of companies versus all your risk tied to
one single company that you are responsible for. So existential stress is much
higher on the founders side. I do miss getting my hands
dirty, like writing code, making product designs. I get to do a little bit
of it with my earlier stage companies, so that
scratches that itch. I would say, though, that
the learning is enormous, and that’s a huge upside,
by being an investor. It’s such a privilege to meet so
many amazing founders, working on so many different markets. Every day I learn something
new about the latest, greatest state of some
technology or a market that I wouldn’t have
known anything about. And it’s just a privilege to
meet all those awesome people and to just constantly
be learning. DAN CAREY: So a lot
of times people– I mean, you always
hear don’t identify too much with your work, but you
see people do it all the time. Do you think that’s actually
a useful thing for startup founders to be doing? You said, as a startup
founder, you sometimes see people’s opinions
of a startup being a reflection of your work. Is that a good
thing to care that much, like to be that invested? JESS LEE: I think there’s
certainly a personal sacrifice that comes with it. But part of me also
feels like it’s necessary in order to get through it. So, yeah, I think it’s
a little inevitable. If you’re too checked
out, you don’t really care what happens
with your company. I think it’s hard to actually
tough it out and make it work. And I feel like I’ve been making
startups sound really terrible, which it’s not. It’s just that it’s epic
highs and epic lows. And the epic highs
made it all worth it. I had so many moments
where I was like, I can’t believe this is my job. I’ve found my calling in life. This is amazing. I love my team. This is the best
feeling in the world. And then also moments
of like, oh my god, why did I leave Google? But that’s just
par for the course. And I think it’s like that for
every founder and every CEO. DAN CAREY: So why don’t we take
a live question in the back. AUDIENCE: Thank you. Thanks so much for
coming to Google. It’s really interesting talk. I have a question. Did you come across, in Sequoia,
any interesting fashion tech companies? JESS LEE: Yeah, I
have seen a lot. The problem is I know where
all the dead bodies are buried because I did fashion tech. So they actually say that
a lot of times investors are less likely to invest in
things that they know too well. So I feel a little
bit like that. Something– let’s see. What have I seen? I think there’s a lot of
interesting computer vision stuff that’s happening now
that enables fashion companies. Fashion is one of the hardest
recommendation problems. Netflix had the whole Netflix
prize for figuring out movie recommendations. But, if you think about it,
there’s not that many movies. Like how many movies
come out per year? Not that many. And then, how much does
your movie taste change, versus fashion? It’s like not only does your
taste change over the years, trends change, seasons change. And then the amount of product
out there is astonishing. And it’s very
difficult to describe. Little touches like silk
or white stripe here, it’s just so unstructured,
and it’s very difficult. And people like very
specific things. And so it’s one of the
most difficult problems. There are some really
interesting computer vision companies that are classifying
products that look similar. And I think that that’s
a very interesting space. I think you can do a lot
more once you have vision. DAN CAREY: OK. Another question in the back? AUDIENCE: Hi. Just thanks so much
for coming here. I’m [INAUDIBLE] in search. JESS LEE: Hi. AUDIENCE: One of the things I’m
curious to know a little bit more about is how
did you balance having a focus versus writing
a blog, being the marketing person, being the salesperson,
being the product manager and so on and so forth? Can you touch a little
bit more on that? JESS LEE: Yeah. So what I tried
to do was I always had my core duties of
product management, and then I tried to only do
one new frontier thing outside of that. So I was not writing code and
doing ad sales and the blog at the same time. I did the blog first, and
I was like, oh, there’s a lot of community
stuff to do here. Let me hire a community manager. And then she took
over that that. Then I think after that
I moved to ad sales. I did that a little bit, then
hired a great New York Times salesperson. And so they were more one– you know, it’s one extra thing. Yeah. DAN CAREY: How many people were
at Polyvore when you joined? JESS LEE: Just the
founders, so three. Yeah. DAN CAREY: OK. And when you left? JESS LEE: 125. DAN CAREY: OK, so a
little bit bigger. JESS LEE: Yeah. Yeah. DAN CAREY: OK. Another question in the back. AUDIENCE: Hi, Jess. So two of the things
that you talked about being very
important to you are having a big impact and
kind of doing a lot of learning across disciplinary areas. It kind of seems like at a
company at a Google scale, it can be hard to have as
big of an impact on the thing that you’re working on and
also to kind of be given those additional
responsibilities or even to be able to seek
them out yourself. Do you have any
advice for I guess trying to find those
opportunities when you’re in a bigger company? JESS LEE: Yeah. Yeah. It can be harder, for sure. What I would recommend, and
what I think I ended up doing, actually, inside Polyvore as
well, was just go do them. If you see something, come up
with a solution or do a little bit of that work and then bring
it to the person who maybe owns that area or might be a manager
and be like, hey, you know, could I work– look, I already
did some work here, can I– prove to them that they
should have you helping them before you ask them,
can I help you? Just go ahead and do it. So that was a big
part of my journey, and I think that works anywhere. In terms of impact, Google
touches so many, many, many people though
that even when you own a small
part of something, you might still be as impactful
as working on a huge thing inside of a company with
much less, many fewer users. But I think the
autonomy is maybe one of the key differences
between small startup and large companies, so
that one’s very hard. I think you just have to
pick where you want to be. AUDIENCE: Thanks. DAN CAREY: So another
question from the Dory. Part of being a CEO and a
PM is making hard decisions. Can you share an example of one
of these really hard decisions and how you approached it? JESS LEE: Yeah. Let’s see. We pivoted our
business model twice. That’s probably– those
were hard decisions. And then other hard
decisions were probably when people had to leave. I would say one thing that’s
interesting about startups that I didn’t realize
until I went through it is there are
people who are just awesome at the early stage, they
love being one of 10 people, they’re so good, they’re
jacks of all trades, and they just love the
freedom and the autonomy. And then as the
company gets bigger, they start to feel
really encumbered and they don’t like it anymore. And you keep trying to make
it work because you just love that person, but
really the best thing to do is actually let them go free
and find the next company. So those were some of
the hardest decisions, because I was like
why isn’t it working, let’s just make it
work, we’ll just rearrange the universe
to work, and it just doesn’t work that way. Some people are just great
for different stages. So I think that was a hard one. The other one was, like I
mentioned, just pivoting. Sometimes there’s
pull there, you know your business
model is not working and you’re not making money, and
you have to do something else. So those are difficult
to roll out to a team. If a whole group of people work
on this particular business model and are no longer
needed, that’s very difficult, but you have to do the
right thing for the company and for the greater
good of that group. DAN CAREY: Now that
you are evaluating new companies,
potential investments and potential founders
that you’re looking at, do you consider that
when looking at founders, like is this person
great in the beginning but I worry about
them in the long run, or is it too hard to predict? JESS LEE: It’s pretty
hard to predict. Honestly, I think if you
met me before Polyvore, you might not have
assumed that I would have been able to get
to the larger company stage. I’m more on the
introverted side. I hate public speaking. I don’t think you
would have said, that person can
definitely scale to run– you know, have VPs and
stuff reporting in to them. So I try to be very, very
open minded about that, and I just look for that
grit, like distance traveled, like can you keep
pushing yourself, do you have a history
of pushing yourself, because you might be
able to push yourself all the way through. Because it’s not rocket science. It’s hard, but it’s a
lot of trial and error and just learning on the job. So that’s more what I look for. DAN CAREY: Any advice for
introverted PMs or founders? JESS LEE: Oh, yeah. I mean, I think you
can be a great leader, even if you’re very,
very introverted. You know, you might not be the
highlight of a cocktail party or something, but who cares? At the end of the
day, you have to be able to convince your team
of what the vision is. You have to be
able to rally them. You know, for my [INAUDIBLE] I
really hated speaking in front of the whole company a lot. So what I did was I actually
had a lot of the other folks on the team speak and explain
what they were doing, which is actually nice,
because other people like being in the spotlight,
they like getting credit for what they’re doing, instead
of me talking the entire time. That was something that I did. And I was still
able to have lots of really meaningful, great
one-on-one conversations or smaller group conversations. And, because I didn’t
like public speaking, I would always have slides. I love to draw, I’m
a designer, so I would make sure that
whenever I was giving a talk, I had a beautiful set of slides
so that everyone be looking at that instead of at me. And that helped. It made me less nervous. And it also, I think, was a
guide for what I needed to say. Yeah. You know, you just find
your tips and your tricks, and I think you’d be a
great leader as an introvert or as an extrovert. DAN CAREY: Why don’t we take
another question from the back. AUDIENCE: Hi, Jess. JESS LEE: Hi. AUDIENCE: I was
wondering if you could share your most recent
public investment and I guess what drove you to
actually invest in that team. JESS LEE: Yeah. It’s in stealth, so
I can’t share it. Maybe I can tell you a little
bit about what they do. So this company is an
on-demand staffing platform, so they match workers,
blue collar workers, to jobs or shifts at companies
like Target or Uniqlo or at a warehouse. They’re live in eight
different cities. So it’s not just a
San Francisco problem. But there’s a lot
of people who– I mean, there’s a lot of
employment in this country, and some of it is actually
due to inefficiencies, so they are a marketplace that
matches people, a really great, hardworking, humble team. They continue to do jobs on
the weekends, themselves, just to make sure they
don’t forget what it’s like. And a lot of distance
traveled with these founders, so I really love their grit. AUDIENCE: I guess
kind of a follow-up. Do you think that
there’s a trend of I guess a lot of
startups that focus more on middle America and a
lot more blue collar things that tend to succeed
and might be harder to find as an investor
since investors tend to be in the Silicon
Valley bubble or New York, stuff like that? JESS LEE: Yes, I do
think that that’s true. It’s something I
think about a lot. Like I think, you know, is
this thing gap widening, or does it help with– obviously, you know, we’re not
pure impact social investors, like Sequoia is where it is
and has been for 45 years because it produces tremendous
returns consistently and has backed legendary companies
like Google or Apple or Nvidia and Airbnb. So it is important that it does
drive performance and drive returns, but those are
things that I think about. And I think there are a lot
of untapped opportunities. And I think that the
company I just mentioned falls perfectly in
that realm, yeah. DAN CAREY: So why don’t we
take one more Dory question. It’s what is
something that Google can learn from other companies? Now that you’re back
here after a decade, what lessons have you
brought back for us? JESS LEE: Oh, I mean, it’s
hard to tell Google, hey, you’re not doing very well,
because that’s clearly not the case. I thought it was
very clever to break Google into multiple companies,
to give more autonomy and breathing room and
leadership for a lot of people. I thought that was a
very, very clever thing. So I guess that’s more something
that other companies can maybe learn from Google. And I think that comes from
maybe caring about that growth and investing in people. Or maybe there’s
financial reasons. I don’t know, but that’s
how I thought about it. Let’s see. I do think the focus– the one thing that I
had already mentioned was just knowing that
you have a runway and that sense of urgency. I do think that sometimes
that can be a really helpful forcing function. Like when you’re in a
meeting with someone for the third meeting
about the same topic, and you can’t everyone
to agree and you’re try to get consensus,
sometimes it is good to think, like, we have six
months to live, should we be arguing
about this right now? Because I think getting rid of
some of those extra meetings would make people a
lot happier probably. So maybe that’s my one thing. DAN CAREY: And then why don’t
we take one last question from the back, and
then we’ll wrap up. AUDIENCE: Thanks. Thanks for the great talk, and
thanks, Dan, for organizing it. So, first, let me apologize
by saying that [INAUDIBLE] going Polyvore’s side,
and so please pardon me. So I understand
that the users were a big component of
your product design and success of the
company, and sometimes when users get too powerful,
sometimes their power is as that troll
mentality as a community. JESS LEE: Sorry. Sometimes there are power users? AUDIENCE: Yeah, they’re power
users within the [INAUDIBLE] users. JESS LEE: Sure. Sure. Yeah. AUDIENCE: They troll everything. Was this the case in
Polyvore’s case that you got blindsided by what users
were saying in some cases or where you had to take
decisions against what the users were asking for? [INAUDIBLE]? JESS LEE: Yeah. Yeah. I think knowing your users
and listening to your users does not mean doing
everything your users want. Because sometimes
they ask for things that just don’t make sense. If every user was
a product designer, then we’d all be
designing products and we’d all be
rich entrepreneurs. So you have to
listen to– you know, when they say I want
something, you have to think, OK, you’re giving me a solution. What was the problem you
were trying to solve? And then you have to remember
that for every vocal user, there’s a ton of silent
users out there, which is why, for us, personas
were very important. So we had clear personas for
the different types of users. There was the creator,
who made all the content and was constantly asking
us for features and talking. And then there were the more
casual shoppers and browsers. And we had personas
for them as well. So I think you use user
research, plus talking to your users, plus personas
and all these other tools to get a sense of how
much to prioritize across your entire user base. But, yeah, definitely
don’t just listen directly and do everything that they say. DAN CAREY: OK, let’s
thank Jess for coming. It’s been great. JESS LEE: Thank
you for having me. Thanks, Dan.

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