Sequoia Partner & CPO Jess Lee: What Great Founders Do Early and How AI Will Change Consumer Apps

As a founder, you're almost starting a cult, getting all these people to follow you on this journey. Bad companies that, you know, don't amount to anything. And so he just laid out those extra dimensions for me and I just use that now all the time. I think, I think he actually invented that frame. I've never heard it from anyone else, but it's like so apt.

Do you think it's worthy to try to be good at all of those or you should try to surround yourself with people who compliment you.

I'm a big believer. Like, nobody's good at everything. And so you just really need to figure out what you're really good at and then you assemble teams that complement you. And I look for very spiky people that complement each other, essentially.

Yeah. So you started as a PM at Google and every company is known for excellence in one area or another. So as you were at Google, as it was scaling pretty rapidly, what were those excellent things about Google's culture that are still with you today?

Yeah, I think being at Google in the era that I was, yeah, actually ambition's a double edged sword and I think this is true of anything. Like your greatest strength is also your greatest weakness. And so the ambition. I watched projects sometimes go off the rails. There was this one project where it was meant to be a classified competitor, like a competitor to Craigslist. And it got brought into review with Larry and Sergey. And Larry said, well, isn't this just structured search, like a classified has a price and a value and just a bunch of structured fields. Why don't we just make structured search and we can put DNA into it and recipes and classifieds. And I remember thinking, who wakes up and says I want structured search today? Like, nobody. And so it's just weird to see that project kind of evolve into this thing that nobody wanted, frankly, because the level of ambition was that classifieds was too small of a market. And I think this is why Google has not traditionally been great at vertical search. It's like each one of those like, shopping. How come Google never completely nailed shopping? It's actually because it was like almost, that's too small for us, which is a weird thing. And maybe another piece of that that Google is not great at was talking to customers at the early stages because you could have caught that very quickly. If you just talk to a bunch of customers up front and say, do you have this problem of no structured search? People would say, no, I don't care about that at all. I don't even know what you mean. Right. But what we would always do is we did a lot of user research at the end of projects. So we would build this complicated product almost to full production scale and then we would put it in the usability lab and we'd have users come in and we say, please complete this task. And they click on it and they try to complete the task. But that's like much too late to be doing customer research. I think we didn't have a culture of customer discovery upfront and I think that's really, really important. And startups in particular be talking to customers all the time. Constantly, Totally.

And I think that leads to a question that I had near the end that I'll ask now. You know, Google was maybe a visionary company in a way. And so sometimes you may talk to customers and they may say they don't want something when maybe the thing you're building is more of like a horizontal enablement layer. Like, I don't want to post pictures online, but then I had Instagram. So how do you think about the balance between talking to customers and just saying we're going to define the vision for them?

Yeah, yeah, yeah. I think Delphi is such a good example of this because, you know, no one is out there saying yet, man, I really need an AI clone.

Some people, you hear me so surprised.

Yeah, no, no, There's a very specific subset of users where, oh, I really wish I could scale my time. See, I think you really have to be careful to understand user problems, not user reaction to the specific thing you are pitching them. And then you just have to have a lot of faith. Right. I think you in particular have this. I always say this about Dar. He lives like five years in the future and the rest of us are catching up. And so, you know, the idea for a digital to you and even things like how the demo works, like, you know, when you, you can get them to complete tasks like the usability research, but really it has to be about the problem, not about your product and their feedback.

And then all of a sudden you were CEO.

Yeah.

How did that happen and why you over others?

Well, I actually started as a user of Polyvore. I was just obsessed with the product and I wrote in to complain about it, but my complaints were neatly organized like a PM with, you know, problems. And then some of them had suggested solutions, solutions. And then that got me an email back from next office. Figure out the business model, talk to advertisers and figure out can we sell them anything. And so I just kind of became not really A pm, but just sort of this generalist, fill in the gap kind of person. And that also included hiring a lot of the people. So especially outside of engineering, for a lot of roles that none of us are the founding team had ever hired before. Marketing, sales. I just became by default the person interviewing for those roles and then by default the person who those people reported to. And so after a while, we had all of engineering reporting to Pasha, our CEO and then pretty much everyone else reporting to me. My title was officially VP of Product, but I ended up, yeah, just running a lot of different things purely by volunteering. So I think the answer to your overall question is just volunteerism. And then the role of the CEO changes over time. In the beginning, it's all about product, product, market fit. Then it becomes the product is not just the bits and the bytes of the product. It's actually the product is the company, it's the org chart, it's the people, it's how you run things, it's process internally. And so that just was more, I was just doing more of that than him. And at some point he sat me down, he said, hey, why don't you be CEO? And so I was like, are you sure? And we just kind of made the switch and I was very nervous about it. But when we announced it, the team, I think a lot of teams, like, cool, makes sense, let's just keep going. And I was like, oh, well, maybe just kind of naturally evolve that way anyway. And then along the way also the other co founders came to me and they said that they wanted me to be an official co founder and they actually gifted me some of their, their shares, which is really special.

Does it take time for you to overcome that nervousness and imposter syndrome? Like there's no pre buff for being CEO.

Yeah, I know.

How do you know what to do?

Yeah.

Or is it just you embrace the chaos? That's just the way it is.

I don't know if I ever embraced the chaos, but I just sort of accepted it. I think in reflection, I had a lot of imposter syndrome because I did not, I could not pattern match against any other CEO that I had met that felt like me. And so I was trying to take bits and pieces of different people's leadership styles, like try them on for myself. A lot of that didn't feel that good or was not very authentic. And so I just didn't have a lot of role models that I felt like I could learn from or copy from. And then eventually I met this amazing Woman, Cheryl Dalrymple, she was at that time she'd been CFO of AdMob. After polyware, she became CFO of Confluent. She's very successful and when she walked into our office, I just remember thinking, wow, this is a breath of fresh air. She's just 100% herself. She was very funny. She made self deprecating jokes. She had this crew of people who would follow her from company to company. And that was like a little bit of a glimpse of what I wanted. I was like, oh yeah, you can just be yourself, not pretend you know everything you're doing. Be really confident your thing, but not have to. I don't know, I just, I just really related to her. And so we didn't even need a CFO at that time. But I just remember thinking like, I just want you around. And so I tried really hard to recruit her and she's like, I don't want to be the CFO of your small shitty company. So I was like, what about consulting? And so I got her to join as a consultant for a few months and then wooed like crazy. Like, I mean, I've done crazy things to try to get candidates, but for her, she went on a vacation to Hawaii. She didn't tell me where she was staying, but I stalked her to figure out where. And I sent a huge bouquet of flowers and a handwritten note like begging her to please join full time. And it worked. And so I got to learn from, from her. And so I learned so much of how to manage people run teams, like, think about financials, like all the stuff I didn't know from her and then actually from another guy as well, who later became Marcia. But yeah, I think I just had a really good leadership team and good mentors. Yeah, yeah. Good mentors that I found along the way. Yeah. But anyway, there's many paths to nirvana as a leader and that's maybe the biggest lesson is there's lots of different styles.

Yeah. What's the most painful mistake you made as CEO and how did you overcome it?

Yeah. It's ironic that today is the date of figma's ipo and as you know, Sequoias and early investors that were very, very happy for them. I think you said you bought 11 shares today that have since tripled in 3 hours, $33.

Just.

My biggest mistake was picking the wrong market and business model. And the reason I mentioned Figma is because early Polyvore, the actual product was kind of like what FIGMA is today. It was an Endless canvas in the browser where you can drag and drop and design things. And people were using it for art. You know, they were making designs. And then some people were using it for fashion to make outfits and mood boards. And some people were using it for home decor. And I remember we had a very early conversation with the four founders and like, which path should we go down? Should we go down the design path or should we go down the fashion and home decor path? Because that would be maybe easier to monetize because there's revenue, you can buy things on the web. SaaS didn't exist yet. So we were like, who's going to buy this weird design thing? And is the web even powerful enough for that kind of tool? And I just remember I was like, I think we should maybe do design. But I wasn't like, I don't think I was officially even a co founder yet. So we made the decision to go down the path of fashion and shopping, and then we became a social commerce platform. But at our heart, we always had people using us because they love to create and design. And I kind of wish we had leaned into that. So I don't think I had enough faith in the business model potential of the design path. And so two big lessons learned, mistakes made. Pick the right market and business model really matters. Different businesses have different kind of like laws of physics. When you are a recurring revenue business like Figma, you start every day with some revenue, you have a year to lose it or maybe a month, and the cash flow is just better versus social commerce. What we were, we start at zero. Every single day, you start at zero sales, you pray to God those customers come back. But hey, most people only shop three times, four times. How many shirts are, you know, to buy a shirt every day. But you're gonna use Figma every day, right? Or every, every, every workday. And so it's just, it's just inferior business model. And I just never factored that in. And so that's something I definitely think about now as an investor enjoying the conversation.

Got a question? You can ask Jess his digital mind. Just check the link in the comments or description. Okay. And in terms of how that affects the decision making, the reason you guys chose social commerce, because it felt like a better business model at the time.

I mean, SaaS wasn't a thing yet. This was 2000, probably 8 or 9 when we had this conversation.

So there's a good lesson there in, you know, there's an unknown opportunity and you can optimize for revenue or you can Optimize what you're passionate about or where the bigger opportunity is.

I wish I optimized for what I was truly passionate about and just. Yeah. Been willing to take the leap of faith on business model.

Yeah. And be okay if it's not immediate revenue.

There's.

Yeah. What was the hardest cultural challenge that you had as CEO? You know, we've talked about product, talking about team and org structure.

Yeah. Again, going back to greatest strength is greatest weakness. I am very empathetic. I see the good in people and, like, what their spikes and strengths are. I think I did not hold the bar high enough on performance. Performance and did not fire fast enough because I kept wanting to believe, like, oh, just a little bit more time. You're gonna be great. Like, I see the potential and at the end of the day, you. You were like, it's. It's about the outcomes for the company. And every time you don't make that tough decision, all the other great people are like, what are you doing? You're slowing us down. And that. That hurts the overall composition of your. Your team and your. And your progress. And so I think I was not. I think I needed to hold a higher performance, which is related to the other thing that is a strength and weakness. I'm super fine with ambiguity. I love creative ambiguous, like unknown. Like, I'm very comfortable in that space. And I hate process, which is kind of correlated. That and I did not institute much process in the team. I didn't want to have, you know, review processes. I didn't want to have lot of measurement. And some of that actually ended up hurting because I couldn't then hold the team accountable if I said, no, this is the target. This is what we're shooting for. If you have a number, you know, matters, you can actually performance manage better. But everything was just ambiguous. Ambiguous. And so people couldn't even tell if they were delivering on the things that I wanted them to deliver on. So the combination of those two things was very bad for a period until I figured out how to fix them.

Cool. I read that Polyvore had a very committed and loyal user base. They were very passionate about the product. What do you think that was a result of? High touch, customer support, your shipping speed, new features, less features that were very delightful. How did you build that sense of community?

Yeah. Yeah. We just had a culture of talking to the customers all the time. And I think that began with me because I was a user. I was part of the community. I just talked to our users in the product, in the DMs all the time. I was constantly playing with the product, interacting and nich making friends on the platform. And so I knew that that was important. So we kind of instituted that into the culture. We would regularly have meetups with our customers and we would, you know, they lived all over the country, but every once in a while we would hold a meetup at the office and invite people from, you know, top users to just come and hang out. I forced engineers to come to those and present. Like everyone had to come hang out. We treated them like royalty. You know, we would take sometimes, you know, when we got tickets to Fashion Week, we would give them to our customers to go and attend. We would throw, I think we were like very high touch customer service. He said, that's something we did. When you came to one of our meetups, our community manager would have gone through all your polyvore sets and creations and found the one product that you was probably quite expensive, you couldn't afford, but used all the time. And we'd buy you that item. And so you'd open your gift bag, you'd have all the, you know, swag all that standard, and it would have that one item that you'd been sort of playing with in your polyvore sets all, you know, for a long time. And just the, the joy, the like. I remember people were crying at our meetups out of happiness. Just like those little touches, like people remember that people remember. You know, there's that Maya Angelou quote. People don't remember what you said. They remember how you made them feel. And it was really important to us that our community felt really special and important and loved by us. And we also wanted the product to have that feeling as well. So we tried to bake it into the product and the little details and design touches.

And in those details, obviously, it takes time to really care about the details and product. But also velocity is really important in product. So how did your org think about Velocity and Delight? Were there different teams for that? Were there different phases?

Yeah, yeah. I think products go through phases where in the early days, and maybe this is probably true here, they're not sure if this is something that customers want yet. Not entirely sure. And so at that point, you shouldn't build for scale as if it's going to work forever and that this is the perfect idea. And so velocity is really important. I mean, velocity is important, period. But you can lower, I think a lot of times the finesse quality bar when you're still validating. If anybody wants this thing at all. And so we did that. But when we were sure, like customers would constantly request certain features, like I need this new feature in the editor, we knew that there was going to be demand for that. So that better work perfectly out of the box the first time. And so I think we just cut different features and products that we shipped into those buckets and then had slightly different bars. Although one trick we did have was for a feature we knew everyone wanted. Sometimes we would ship it slightly broken and then have the fix ready to go. So as soon as they complained, we would fix it. And sometimes we would also catch things that we hadn't thought of that we'd fix. And so the community felt, oh my God, when I talk to this company, interesting things happen, people reply. But it wasn't just like the thing we held back. But oftentimes we would discover like little and just, you know, I went through every single comment on our blog and I would read it, we would tally them up and say, all right, what percent of people liked it, didn't like it? Like we were really, really customer obsessed. And I think that was just a culture that we set. And so even when we screwed up, people were much more forgiving because they remember they heard about the time that the meetup happened or they, they had seen me. Like I think one time someone what something really mean about us on somewhere from common on the Internet and our community came out in droves and they replied in the comments and like personally defended me, you know, because they kind of knew me from the site, you know. Yeah. I bet your customers love you. Yeah, you come around.

Yeah. So let's talk about you at Sequoia, you've obviously worked with a lot of founders. You run ark. I'm curious, what are traits not just in founders but in teams of early startups that you've seen be indicative of long term success?

The number one is velocity. Yeah. Yeah. So another wonderful coworker, Mike Vernal, he's now a conviction partner, but he was at Sequoia and then before that he was a Facebook product vp. He likes to describe startups as like a turn based game. You play cards and you turn over a card and it's very hard to be more right about the next card or get, you know, figure out like make every decision correctly. But you can certainly make decisions faster and flip more cards and just getting more turns and more add backs, you just find the answer, you get to the right place faster. And so that's the one thing you control is you control Velocity and how fast you ship, like that is really, really important to finding product market fit. So that's like probably the number one thing. And that's something I think this team is very good at. And you in particular. I think one time we had like a one on one and I was like, maybe you should get a PM. And like 15 minutes later you sent me like a PM job description. Like after the one on one. I think you just make decisions quite quickly and then move on things. And so, you know, you don't gain that much from waiting around because you're, you're not, you're.

The best way to get data is just jumping in.

Yeah, yeah.

And moving from operator to investor. Are there any things about your worldview that have changed significantly since joining Sequoia that maybe like before you thought something and it's actually not the case at all?

Yeah, yeah. You know, I used to have this maybe more romantic notion that startups are just excellent teams and excellent products. And then I added excellent business to that and that I just said you have to be brutal about. And it's exactly what I described before. Like some business models are just better than other ones. And at the end of the day a business, a company is also like an engine for producing cash. At the end you have to be a self sustaining cash machine. And there are a ton of metrics that drive that equation. And sometimes let's say you're a beauty business or a commerce business, a GMV business, like you just have worse repeat rates, less recurring revenue. And then because of that, the dollar revenue that you produced is not created equal to the dollar revenue produced by another company. FIS has like a 7 to 10x multiple versus commerce companies have like a 3 to 5x multiple. It's just how the business works. And that is something that I've had to reckon with. I think I have invested in companies where the business model was like just inferior and that just hurt us the entire time. No matter how good the founder was, no matter how great the product was, it's just very, very hard. And so now I try to factor that into my, to my calculus, but that's like a, you know, a big lesson learned.

Totally.

Or maybe the other thing, which is maybe not contrarian, is the importance of storytelling.

Sure, yeah.

That's another trait I look for as a founder. You're almost starting a cult. It almost has to be like a cult leader. Like you're getting all these people to follow you on this journey. That really doesn't make any irrational sense. Like you could go get a job at Google and make like, I don't know, 400k. Why would you go to a startup and make a lot less? You're joining for the dream, the story you like, the person you like, the idea you want to be part of something special. And so the ability to tell that story in a compelling way is so important. And you're not just doing it to people at your team, you're doing it to your customers, you know, investors. And so being able to tell a good story and be compelling, like, really changes your ability to run a company. And so that's, I think something I knew was important but became more important later. It has to be substance and story, but the story really matters.

Yeah, I've realized that as well. Do you have any really hot takes or controversial opinions that might be against the VC tech Twitter norms?

I love consumer. I love this company because I think it's one of the. Has high potential to be a massively adopted consumer company that today feels a little bit unusual or niche. The best consumer companies often start out that way. Remember Snap was this, like, obscure, like, what, your pictures disappeared? That makes no sense. Or Airbnb, Like, I don't want to stay on someone's couch. Like, that's insane. And then they became massive companies, right? And so I think this, this has that flavor. But in consumer, consumer has fallen out of favor for the last, I don't know, 10 years. Not a lot of great new consumer companies have been created. But I think we're in this, like, really fertile period. And there's two types of consumer, right? There's consumer utilitarian. You know, think about DoorDash or Google search. It's very utilitarian. And there's consumer entertainment, there's media, there's gaming, there's like social platforms. That is what I am drawn to. That is what I, you know, will spend a lot of my career building. And I think within that media is having a moment. At this point, all VCs, media companies are not tech companies. Like, media is dead. Like a terrible business model. When I go on TikTok, what I see is I see a lot of what today is termed AI slop, right? Like bad, you know, fanfic, AI generated videos. But it is getting better and better and better. I saw this one that was Harry Potter crossed over with the Hangover. And so, you know, Draco and Harry Potter are like, we can't find Ron. He's gone. Why is there a tiger in our bathroom? Which is like literally the plot of the Hangover. We're Harry Potter characters and it's actually pretty well made. I mean characteristicity is not good. The faces change slightly from you know, part for parts of the story. But it was really entertaining and it would be very hard to make that any other way except with AI. And so I think we're going to see this with like what looks like weird niche fan fiction and then it's just going to start to become AI short form stories, Ao AI micro dramas, just full on content. And I think there's a possibility of someone creating sort of the next YouTube or the next Netflix. But it's a lot a new creator class. Right. Because you could argue that YouTube will be that. But the people on YouTube are FA like they have a class, different skill set. They're famous because they're good at filming, because they're hot, because they're funny. This is a different group of people who are not showing themselves on camera who are just have good ideas and know how to use the tools like that. I don't think will necessarily work right away on all the other platforms. I think there's an opportunity there. I think a lot of people write that off in the same way that they've written off the micro drama category. I don't know if you know this but there's like a $2 billion micro drama category that's you know what Quibi.

Tried to be kind of.

Yes, what Quibi tried to be. Instead they should have focused on romance stuff or romance or like short form. Form cheap. You know. I think it's filmed like by a lot of USC kids who are in film school and that has blown up and now in China that market is bigger than the Chinese film industry. So it's clear there's demand there. So I think though that the combination of these two trends is really interesting. But a lot of VCs and people are going to write it off because media is a bad business.

So you've alluded to spikes multiple times and you mentioned like Dara's was for example like velocity and recently I've been thinking about this as well. One of the people on your guys data science team reached out to me was like talked about like they wanted me to talk about people I know but all I could say about them was what their superpower was.

Yeah.

And I found it to be a challenging exercise to do because I was like saying they're hard working or relentless. Is that even a superpower?

Yeah.

So some something that you're thinking about as you're looking at founders is like, what makes a good, durable superpower for them. Because I think that could also be something that we use when we're interviewing people. How would I evaluate a superpower that actually is valuable as much as something that's kind of out there and present in the market?

Yeah. I think what's really important in hiring is a sense of fit. And, you know, there's also. There's always. That's also culture fit, but like role fit. Right. Because different spirit spikes are useful to different types of jobs. Right. And so you really need to understand what's like the most important thing to get right on this team with this one for this job. Right. Which may be different than a different kind of job. And so I think you just have to identify the fit. And then the other thing you think about is the team composition. So especially in the early days of Polybor when, like, nobody knew who the hell we were and we couldn't hire, like the very, very best, like 10x and all 10x all dimensions, it was very hard to recruit great talent. So I would often just find someone who's really spiky in one dimension, but potentially like a little bit deficient or weird in another dimension that you would normally want for that role. But then I would just pair them with someone who was really good at that one thing, and then the team was able to produce the right output. A very specific example, you think about product managers. Product manager is supposed to be organized and project managed, but if you're working on creative, delightful products, sometimes you need to be really creative and out of the box. And sometimes creativity and organization do not exist in the same person that. Well. And so I think that's true of me as well as a pm. And so I found this guy who was extremely creative and very bright and very high standards, hopelessly disorganized, and usually a PM who cannot organize stuff is like dead in the water. But instead we hired him and paired him with a designer who was really, really, really organized and just project managed the project. Right. And it's just a simple example. Put together a pod of engineer, designer, and PM where you just need all the bases covered, but they don't have to be traditionally good at the thing that they are supposed to be good at. Right. And so that's like, maybe a very small example. Yeah.

You went into an industry without really having, like a investment background. Also, I think you were the first female partners at Sequoia. Like, how did you navigate that?

Yeah.

And.

And learn about the industry and Yeah.

I had not done a single angel investment before joining Sequoia. They made me a scout for like a hot second at Sequoia and I didn't make any investments. So that what you said is true. I did not have sort of the background of having hicked companies. But what's interesting about Sequoia and I think part of what differentiates the firm is the ethos was like, no, no, your job is not like a capital allocator who managed the portfolio. You're not a financier. Your job is to be the consigliere to founders, to be the long term company building partner, to really get to know the team and the people and help especially in the crucible moments, which is what we call the like those inflection points where you have to navigate too big decisions. And that just really appealed to me because I remember that was like as a founder I don't think I necessarily had that person and so I just kind of wanted to be that person. That said, I still very much identify as someone who likes to build things and there are many Pastor Nirvana, including at Sequoia. So within my role there, I'm our Chief Product Officer, which is like a weird title that I don't think I've seen at another VC firm. But what that means is I help run our product and engineering team and our job is to make the firm technology accelerated AI first, help us pick great investments. We just did a hunting party this morning that I helped run where we're like, all right, we're going to scour our database and hunt for interesting robotics companies for one of the growth stage partners and we use a lot of technology to do those things. And so I do, I spend a lot of time on that because I still actually just like building things and that's useful to Sequoia. But then I also help run Sequoia's ARC program, which is our seed and pre seed stage program. And so Sequoia I think gets the best out of me. But it's also what I love to do and I just feel very lucky that I get to do that.

Alright, thank you so much, Jess. It's been great. Thanks for tuning in. If you enjoyed today's episode and want personalized advice from Jess, head to the link in the comments or description to ask her DigitalMind on Delphi.