Being an Accidental Startup CEO

A conversation with Lilly Chen, CEO, Contenda

I started this series to give insight into the challenges leaders face. I want to change the way we see leadership and who gets to be a leader. I recently tweeted that I was looking for more underrepresented folks for the series. Lilly Chen, the CEO of Contenda, answered the call. I’m thrilled she did. She spoke eloquently about her past as a Buddhist monk, how she accidentally created a startup (and became its CEO), and made a conscious decision to change the culture of the company. Lilly also offers a different take on the CEO role, one I hope more will consider.

This interview has been lightly edited for length and clarity.

Can you introduce yourself, Lilly?

I graduated from undergrad in 2019. I studied math and econ. I'm currently the CEO and founder of Contenda. Contenda is a unified content repository that helps businesses resurface and repurpose technical content.

I want to talk about Contenda but first, I understand you were a monk?

I was a monk. Yeah.

Can you tell me more about that?

So when I was 16, I dropped out of high school. I actually had a chronic illness, a thyroid disorder. And there was a time when we weren't sure what the cause was. We were seeing all sorts of doctors, and going to all sorts of places. No one understood my symptoms. Eventually, my mother who’s relatively religious was like, "The answer is to become a monk. Why don't you move to China and live in a monastery and just see how that goes." The worst part is it worked. The worst part is it worked. It's one of those things where chronic illness can be managed through diet and lifestyle as well. When you're a monk– you live a vegetarian lifestyle, you have a very regular sleep schedule, there are no electronics, there's nothing kind of out there to stress you out. That worked for my symptoms.

Obviously, you're not a monk now, you're a CEO. How did you come to leave the monastery?

The monastery was in a pretty remote mountain location in China. So we didn't really have any technology, no entertainment. So the only thing I took with me besides a few changes of clothes were books. I really, really loved to read as a kid, as still an adult, love to read. So one day I was just reading on the footsteps of this temple and the head monk comes up to me, he notices I'm reading. He said, "You're always reading." I said, "Yeah, I like books." He said, "There are not many books here." I said, "That's okay. I brought my own." Then he asked me, "Why are you here exactly?" I told him, "Oh, my mother is here." I'm 16, so that's a very valid answer to be in any place. The monk said, "Do you want to be here?"

When you're a teenager, no one ever really asks you what you want out of life. You go to high school, you take your SATs, you go to college, you get a job, that life is planned for you. When he asked me that, I paused for a second and really thought about it and I was like, "I don't think so. I think I miss my friends. I want to be a teenager. I want to go to prom. I think I want to go to college." He told me, "The monastery will always be here. You can’t make an informed decision unless you've actually lived that other life." He encouraged me to do it. I told my mom and my mom was like, "Well, if the monk said it, then yeah." So we moved back to America and I re-enrolled in high school.

How long were you a monk?

I was a monk for two years. I dropped out of school for about a year and a half and I lived at that particular monastery for two to three months. 

That's such a fascinating story. I have 10 more questions about that, but I'm going to save them. So you end up going to college and then working at Facebook.

I did. Begrudgingly. When I went to college, I was a little behind.. At that point, I always felt like I was playing catch up. In college, I studied math and econ because I wanted to get a PhD in economics. One of my college professors encouraged me all the time to pursue research, to pursue economics. It was a passion point for me, but because my parents (they're no longer active monks) are practicing Buddhists. They don't have many means and my little sister also developed an illness a few years ago that required a lot of medical attention. The burden kind of fell on me to resolve those family debts. So I needed to make money and you know what doesn't make money? A PhD student.

After I graduated college, I knew I needed to make money somehow. So I started learning how to code by just basically trolling Twitter and seeing what people were writing about. Like, "How do I break into tech without a CS degree?" I started just coding on my own, doing HackerRank problems on the internet. That's how I got my first software engineering job in Boston as a DevOps engineer. I was the first engineering hire at a gaming AI startup. And then ultimately ended up doing a stint at Facebook as well. I was building CI/CD pipelines for ML engineers there.

Very cool. I'm a former COO of Travis CI, so I know the CI/CD world and have spent a lot of time in the developer tools space for some reason, even though I'm not a software developer. No one wants me to code for them. I talk to the code. I'm like, "What are you doing? Why do you want to do that?" And the code doesn't change.

Beep, beep boop.

Right, right. It's a one-sided conversation and the cursor just blinks. How did you come to start Contenda?

Kind of out of boredom. I was working at Facebook. I needed the job because that signing bonus alone paid off pretty much all of my family's credit card debts. So I’d never look down on anybody who works at a FAANG company, Facebook, Coinbase, wherever you work it's a job. If you need that money, you get that bag. So that's what I was doing. But the job itself wasn't extremely fulfilling. I thought I was going to just take some time off, and hang out with my sister. I was in California, she was in the suburb outside of Philadelphia. So I thought like I want to spend more time with her, maybe after this is all done I'll just take a break for a while. So I decided to take leave from Facebook. 

And I had a few weeks before my flight back, this was peak COVID time. I asked my childhood friends, I asked them I was like, "Hey, do you guys feel comfortable getting on a plane? Because my house is empty and I'm kind of lonely and I kind of want to hang out. I'm a little bored. I don't really have anything going on. Do you guys want to just come hang out? We'll just play some video games." They responded to the call. I’m really lucky. They were like, "Yeah, we'll get on a plane." So they came out to California and we just started hanging out playing video games. After a few days, I was like, "Hey, do you remember when we used to do hackathons in college and stuff like that? When you just build something over 48 hours or a week or whatever, that could be fun. Maybe we'll do that. That might be enjoyable." It was kind of like, "Yeah, yeah. Sure, sure, sure." Very non-committal.

We ended up building something. There was a Twitch streamer at the time who had broken a Guinness world record for most subscribers in a month. His name is Ludwig and we'd emailed him. We asked him, "Were you interested in doing some kind of retention strategy with your subscribers? If so, we'd love to build something for you to help you do that." And so he broke a record for 200,000 subscribers that month and we signed a deal with him for a dollar per subscriber.

What a great story. What happened after that? Did you go get funding? How did you decide, "Oh, this is a business that we need to start building?"

We didn't. My friends were still in college. They're like, "Should I just finish college? If we started a business, I'd have to drop out." I was also thinking, "Yeah, I'm bored at Facebook, but the money is good. It's consistent. Do I really want to risk my family's financial stability to pursue some kind of pipe dream?" And we ended up talking to a few investors, met some really, really cool people and they were all like, "You got to do this. It's a once in a lifetime opportunity." There are not many people who could happen upon something like this the way you guys did through your friendship, through essentially just chasing something fun, not necessarily money. And so yeah, we took it. We took our first pre-seed funding for a million dollars in March of 2021.

How many founders are there?

Yeah, so I am CEO. I'm the only one with a C-suite title. The other founders have the title Founding Software Engineer. There are three of them, Clara, Johnson, and Steven.

How many folks are at the company in total now? Is that?

Ooh, I want to say there's nine in Philadelphia. Then we have five or six remote folks. So we should be around 15. You think I would know, right? You'd think I'd have that number off the top of my head. I don't.

Is this your first leadership role?

Yeah, I was in IC before this. At Facebook I was just a regular software engineer.

You were at a startup before, right?

Yes. I worked at a friend's gaming AI startup called Midgame, based in New York.

How big was that startup?

It was three full-time and then we would occasionally have a couple of interns floating around and maybe some other people come in and out, but that was kind of the core team. That startup went under largely due to COVID. So when COVID very, very first time came around, I think the markets got really unsteady. And when I joined, they were limited to I think four or five months of runway. So it was already going to be very, very tight. And at the end of that runway, everything shut down. 

We went to complete quarantine for the first and only time. At the end of that, I told myself I was like, "You know what? This is awful. Startups are so risky. Every day you wake up, you have no clue what you're doing, you don't know where you're going, what's happening. It's not great being your own boss. It's terrible. You can't slack off."

Oh, interesting. You went back to startups and became the CEO of one. What changed your mind?

I don't know if anything actually did. I mean, the first time we had a term sheet in my hand…Both Steven and I were laying on the couch with bags in our hands because we were worried we were going to throw up and we couldn't move, we both hadn't slept. It was truly awful. I mean, I remember in the most ironic of things, we were watching Silicon Valley on HBO, the one about startups. And we were watching Richard, that poor CEO, going through the runs, the motions we'll say.

I remember just the two of us watching the show, eyes glazed over in fear and exhaustion and then looking at each other, looking at our bags, looking at the TV, we did that for almost like a week. But yeah, I mean honestly I think part of it was we never really made an active decision to do it. We just said as long as this continues to be fun and enjoyable for us, we'll just keep doing it. If it stops being that we'll just stop doing it.

I love that decision-making process. How did you become CEO?

Well, we grew up together. I'm the oldest of them. So when you're kids, you know when neighborhood kids form playgroups, and they always kind of default to the oldest person. Truthfully I think the other founding team members are better engineers than me. I learned how to code after them, they actually have CS degrees and things like that. So they've been coding much longer than me. But I have more industry experience because I'm older and I kind of jumped right in. But yeah, they kind of just decided they were like, it makes the most sense for you to be the CEO.

This whole thing is so great. You and I connected on Twitter and when you sent me a DM I thought, "Oh my gosh, I need to tell this person's story because it's such a fascinating story and you are living up to it and more." The whole process of how you... being the oldest and them being better engineers means you became the CEO.

You know when you play pretend CEO when you're five years old? Yeah that, but now in adulthood.

Sometimes I think there's this idea that people might fight over being CEO, that people want the CEO role. I don't know about you, but I don't want the CEO role. I think it's high pressure, you're doing everything, with high scrutiny, a lot of weight rests on you even when you have co-founders. It's a tough role.

I have actually tried to give it up in the past. There was one time when I said like, "UN-ironically, would any of you be interested in a little swippy swap? You know like that show Wife Swap, a job swap. Would any of you be interested? I really miss coding." I have not coded for a majority of my day, probably since August. And I feel like I had just started, right? I had just become a software engineer. I had worked so hard just to become a software engineer only for this to happen. And for it to just... It's not for nothing, but it's just like I see them coding sometimes, I get jealous.

I take it no one took you up on your offer.

No, no. They were like, "Ooh, we don't want none of that." We did play a fun hypothetical game, like Succession. It was when Succession was trending on HBO. We were like, "Yeah, who would take over the empire? If I were to die suddenly?" It's a gruesome thing. Don't mind us.

I love the relationship you all have. Well, I guess a little bit more about this whole idea of CEO, what are the parts you like?

I think at the end of the day, I have it way better than everybody else. I know you were saying being a CEO is a tough job. I agree that it's a tough job, but I think that in today's markets, the CEO is probably the best role actually in terms of society. Let's take the worst hypothetical Contenda fails. In that situation, yes, I am the one responsible for the failure. But theoretically, at this point we still have almost two years of runway, right? So we'd still be doing this for a couple of years. 

As a CEO, I get to decide all the things that I do, the skills that I pursue, I need no clearance from anybody else. I will learn how to do sales, marketing, and product, as well as all the engineering skills I had, as well as managing, as well as investing, and pitching all of those things.

I often get to do a lot of things like speaking at conferences or traveling to meet investors. And that's all things that regular ICs don't get to do. And on top of that, I'm not at risk of being mismanaged. 

So when you're early in your career, your manager kind of has your whole career in their hands. And having a bad manager can create a lifetime of bad habits. I think there are a lot of people out there who you start working with and you're like, "Oh, why do you hide things? Why are you worried about telling somebody that this didn't pan out the way you expected? Why do you feel like you need to work when you can't because you're sick or because you have a family emergency? Why do you do that?" And it's oftentimes because their first manager pushed them to do that and it became a lifetime habit. So really working at a startup puts you at risk for all those things. Being the CEO of a startup does not.

That's a fantastic perspective. I want to talk about culture. You have a hybrid structure, right? Some remote summer in an office, as we kind of talked about what have you all had to sort of think about when it comes to having a hybrid sort of structure?

Yeah. The first things that we did were, we just made sure that we had the hardware to support this. So we call it the Eyeball. You can buy this conference camera essentially that has a remote control that has 270 degrees of view, it zooms in, zooms out. It has a mic that can pick up 20 feet in either direction. That's important because it's frustrating when you're the remote person to not be able to hear or see. So that's number one, just make the day-to-day easier. There are a lot of really, really small things you can do. When you have an in-person conversation, make sure that you close the loop on that async platform that you use. If it's Slack or if it's Discord, whatever it is just summarize. Be like, "Hey, Blank and I talked and we made this decision for these reasons. If anybody wants to add anything, let's do it here."

I also think there's no substitution for face-to-face interaction. So we just fly everybody out. We bring them to Philadelphia. It's nice here, we hang out with them. We play a lot of games. That's I think an old tradition for us just amongst the founding team. We call it the Contenda Hack House Showdown Throwdown. The one that's on the calendar that's coming up, because we have a couple of people remote who are flying in. Our next one is called the Contenda Hack House Showdown, the sixth, Return of the Jedi, Revenge of the Contendeez, Tom versus Jerry. We like ridiculous names. Tom is one of our employees, he just joined.

It's not about how well you think you're incorporating remote folks, but how well the remote person feels like they're being included. So gut-check them, not yourself.

Solid advice. Startup CEOs think a lot about product/market fit but also about how to create an effective company culture. So was that something that you thought about, I mean you all sort of accidentally found a startup. Is that accurate to say?

That's true. I would say that I fell into it. You know when you slip and fall?

Slipped and fell into a startup.

When you think about culture, was that something that as you started that you thought about, what kind of culture do we want to create, values, mission? How did that come about?

I would say it's an ongoing process. I did not sit down before founding a startup and think about all the things that I saw in my previous companies that I would never want to do. Like “I'm going to do it differently!”-- I didn't have that. There was no epiphany moment. I honestly think that culture-wise, at most companies it was fine. There was nothing wrong with it. Nothing glaringly wrong anyway. I will say this, I think that at the beginning, I think I was a really bad manager. I think I was at risk of doing terrible things to my employees because I remember at the beginning we were working 10 to 12 hours, five to six days a week. It was really bad. We were doing that because we felt like we needed to, we were like the clock is ticking. Everything is urgent. Startups are urgent. You need to build fast.

And then at the end of that, we finally found something. The current product that we're building, we're building an enterprise SaaS tool for developer advocates. That came at the very, very end of that. The way it happened was so serendipitous, that I realized that putting in all these hours is very performative first of all because you hit a point where you just stop being productive. So there's really no reason to enforce hours on anything. And there's no reason to enforce an in-person thing either. So we were originally in person and completely synchronous. The day started at 10:00 AM and it theoretically ended around 7:00 or 8:00 PM. It sometimes went on longer than that. But there was a mandatory thing that everyone needed to be here exactly at 10 o'clock or earlier. I realized at the end of that sprint, that this was actually kind of unproductive.

It's also not inclusive of people who have other things happening in their lives. Or even if you don't have other things. And you just realize that it's more convenient to work out at a gym at 10 because it's less crowded. There are just so many reasons why having a flexible work schedule, as long as you get your work done and you're making progress on your business goal, you don't need to enforce these things. I did it at first because that's what all my other jobs did. They were 9 to 5s, you clocked in at 9:00 and you clocked out at 5:00. You moved your life around to accommodate your work. From there on out, we agreed that we would move our work around to accommodate our lives.

I love that because also there are people like me who have chronic illnesses. I would never be able to have a job like that because my body doesn't want to cooperate sometimes at noon. It might cooperate at 8:00 pm or sometimes at 7:00 am. I think it's easy to fall into modeling what we saw before. Most of us do this.  

For sure. Yeah. And you know what, that's part of the problem was. My chronic illness is under control and so I no longer see symptoms from it. So I don't live that life, but I realized it when one of my engineers was like, "Hey, I have a chronic thing. Some days just aren't good for me. And I can't get anything done even if I'm here. I can be here if you want me to be here, but it's not going to be good for anybody.” I thought, "Okay, you're totally right. And there's no reason for me to do this, so we're going to stop doing it."

What an incredible conversation. I have the chills as you describe it. That person was like I'm willing to be vulnerable and say, "Hey, this isn't working for me. Even though there's all this momentum it's not working." And for you to go, "Okay, let's change it then." Being so flexible about that.

For sure. I do think our team culture... Well it's because we're childhood friends, right? So we've known each other for a very long time. We talk about a lot of things. Our families have known each other forever. I think that's something that as we've grown, we've tried to keep doing that with every new person, but it's tough. Vulnerability can't be exposed instantaneously upon meeting a large group of people, but we're working on it.

What was the transition to this new way of working like?

Growing pains for sure. We weren’t as good about getting communication documentation out. When we first started, it was just so hard to know where we were. And there's this discomfort of not knowing what people are working on, are they making progress, are they asking for help if they need it? I can't physically see it, how do I know?

I realized the discomfort was a conflict within myself wanting control over this situation. I think just realizing that you actually have very little control. You have very little control over most things. Life will do things, the market will do things.

People will do things and you can't control them, you can't control the markets, you really can't control many outcomes. So just focusing more on what I can do to best support people, help them grow and also think a lot about what do I want to get out of this? Because I don't think I ever really thought about that. What do I want to get out of building a startup? Like you said, we happened into it. So I never had that purpose and because I didn't have that purpose, I don't think my actions early on had a well-defined kind of motive.

It sounds like you became more clear. At that point did sit down and think about what kind of culture do I want to build? Or was it more about putting in place some structures and things around half being remote, working when you want?

I think more fundamentally I needed to answer the question, what kind of leader did I want to be? Or maybe even more fundamentally, what kind of person do I want to be? I mean, I'm now 26. When we started this I was 25, just a couple of years out of college. And again, these are people that I grew up with. It was tough to figure out what my identity was outside of the group dynamic. Outside of the expectations of, you're a fresh college grad you should just focus on climbing the corporate ladder.

Did you come up with something?

I realized that the thing I wanted at the very most to get out of Contenda, was I wanted to help as many people as I could. I think Suzan, you, and I understand this about each other. Whether it was my employees, my customers, my investors, or, anybody I came in contact with, I wanted to lift them up as high as I could. When I realized that, that was my goal, it became so much easier to make decisions around company culture because now I have a purpose, now I have a motive. Now I'm not trying to maximize the amount of productivity that I can extract from you as a human, but I'm more trying to figure out, how can I help you get the things that you want in your life?

So that engineer who has this chronic health thing, where every couple of days they're a little bit incapacitated, we'll say, I asked them I was like, "I'm assuming that someday you might like to have a kid. You want to take them to places. You might want to do these things. I know that about you. So how can we find a way to make it so that you can get those things in life without letting this illness kind of bog you down and prevent you from getting there. Because these sound like things that you want to do." So we've been working on things like that. I try to figure out how do I set my schedule in a way that's productive and understand more about what my needs are so I can ask for them too.

That's a really big shift. It sounds like figuring out how to take individual needs into account and support them to be their best selves. Not just productive human beings, but their best selves and accomplish all the things what they want.

And I don't think it's mutually exclusive to running a good business either. We do less, but we do more important things because we're very focused now on what matters. We spend less time worrying about, "Did I work enough hours today?" We spend more time thinking about, "Did I bring the value that I promised?"

It's so true. As we discussed before, as someone with chronic illness, I can't work 10, 12 hours a day so my life is about focusing on what is most important and urgent. If I get that done, I feel happy. It's been a discovery process for me too around that. It sounds like you all thought about this consciously.

Yeah. I'm definitely trying to help a lot of people figure out that discovery process of what is urgent and what is important to you. That matrix that people talk about. Identifying what those things are because I do think a lot of times you go through life and you don't think about what gives me energy? What makes me feel recharged and motivated? What makes me feel like myself?

I think it's true. We can get on autopilot. You might cringe at this, but it kind of reminds me of that monk who sat you down to ask what do you want?

Yeah. It’s true. I think that's where it came from. This man didn't really know me. I just called him shifu (掌握) which in Chinese means master. I didn't have a name. I was just a floating teenager, a passerby. He sees a lot of people. A lot of people come to the monk to pay tribute and things like that. But he took a moment just to check in with me as a person, to see what I wanted out of life to see if maybe he could offer something. 

He just offered a few words, "I see that you enjoy something. I'm acknowledging you. I acknowledge this thing that you like doing. I noticed that you can't do that thing as much as you'd like here and now I'm going to ask, would you like to return to a place where you could do those things?" And that framework is exactly how I interact with all of my employees. I say, "I notice that this thing is occurring. I acknowledge you. Is that something that you want? Is there some way I can support you in getting the thing that it is that you want?"

That's an incredible thing that you learned at a relatively young age, that you bring to being a CEO. It’s a wonderful gift to give to the folks you work with.

Yeah. I mean, I think it's the minimum I can do, considering that they are entrusting me with their careers and their financial stability. I think that's probably the least I can do.

What’s been the hardest challenge you’ve found being a CEO?

Probably realizing that I didn't know very much about myself. I thought I did. You always want to think that, right? You always want to think that I know who I am. I know what I want in life. But no, I think early on, I was solving immediate problems. Like my family needs money. I need to find money. It was very much a problem, solution, problem, solution. I always try to solve other people's problems, but what am I looking for? Realizing what my motivations are, what gives me energy, right? The same questions that I'm asking other people. I realize the things that give me energy are seeing others progress.

Seeing others grow, fulfills me. It makes me so happy. It makes me content with life. And there are a lot of small things for me. Right? I notice that I really enjoy the feeling of progression. I've been working towards a backflip. I've been working towards this backflip and there's no reason for it. I just think it'd be cool. I just think it'd be cool to bust out a backflip at the bar or a party. It would just be fun. But working towards the backflip is interesting because if you're an adult who has no gymnastics background, you should not just attempt the backflip. You will break your neck. But the way an adult who has no previous experience, the way they learn a backflip is the coach starts you off with things like, just jump as high as you can and try holding your arms by your ears.

It's a really weird motion. Then they say, "Try doing a backward somersault." Which is also a weird motion. The idea of rolling upside down and backward is foreign to most people if you've never done it. Then they try to get you to jump onto something high and roll backward off of it. There's this progression feeling. Eventually, they take away those mats, and then they're like, "Okay, so now we're going to do that same exact motion but I'll spot you." And they do that. And then you realize at some point that you've been doing backflips and they're not even holding you anymore. I think that feeling is something that I've enjoyed so much.

This past year, I've learned how to snowboard besides backflipping. I've been learning West Coast Swing dancing, which is really fun. I have no dance experience. I got into powerlifting and things like that. All these fun life things. Bringing kind of that same philosophy to work, to grow, to other people's progress, helping them get to wherever they need. Because sometimes you just need a coach to tell you, "Well, let's just try this thing and I'll spot you, so don't worry about it. You will not break your neck. I got you."

It’s like CEO as coach. Rather than just taskmaster, which I think is a very strong stereotype we see in the media and we think of a CEO maybe. But I see you as like CEO as a coach, it sounds like the frame of reference you had to a degree.

Exactly. That's exactly how I see it.

As a coach obviously, I love that. What advice might you give to other CEOs or leaders who want to approach their job as more of a coach rather than a taskmaster or a boss?

I think about the first time I said no to an investor. So investors often see a lot of CEOs. I think there's a push to be a certain way. I'm going to name those that failed in my opinion, like the original CEO of Uber Travis and Adam Newman of WeWork. These are people who are taskmasters. Those companies ultimately I don't think achieve the right outcome, but they did grow. They did the thing that venture capitalists want to see. They became unicorns. I think that because of those people's examples, you start building this archetype of what a leader looks like. You think you need to be these things, need to be intense, tough, and push everybody. And if somebody stops working, you better fire them. They actually say that. They say, "Hire slow, fire fast." That's a saying that I was taught very, very early on.

Think about what kind of person you want to be. In a worst-case situation, if everything goes to crap, what do you want to get out of this? What kind of person do you want to be at the end of this?

I know that even if everything goes terribly, all my employees are extremely hire-able and you'd be lucky to have them because they're not only fantastic engineers, they are amazing humans. They understand business problems, they work really, really well with others and they know how to have a good time. They're extremely ideal hires. And I know that for myself, that's also true. There are many, many ways to lead a team, to lead a company, but think a lot about who you are and what you want to get out of it.

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