Jessica

We rejected them. Because at that point, we did not realize that when you fund an early stage startup, it's more about the founders than the idea. But I distinctly remember how much I just enjoyed talking to them. And then the next Monday, Paul reached out to them and was like, We really liked you guys. Do you think we could maybe brainstorm a new idea? And they literally got off the train in Connecticut and got back on a train to Boston. And they came up with the idea for Reddit then, and they were in our batch.

David

Welcome to Leap Forward, a show about founders and the people who believed in them before anyone else. I'm David Rusenko, and for this first episode, a person who's given so many founders their start.

Jessica

I'm Jessica Livingston. I'm a co-founder at Y Combinator.

David

I wanted to start this series with Jessica because she's not only been pivotal in my life, but in the lives of so many other founders. So far, YC has launched over 5,000 companies worth almost a trillion dollars. And this time, I wanted to hear her origin story. I first met Jessica in 2006 in a 15-minute interview when my startup, Weebly, got accepted into YC. But there was someone else in the interview that day who I also wanted to talk to to help us fill in the story. Someone who could speak to Jessica's role better than anyone else.

PG

I'm Paul Graham and I'm Jessica Livingston's husband.

David

Oh, what do you think people sometimes miss about what Jessica's contributed to YC?

PG

Oh my god, they miss everything. Like, so there's so many copies of YC now. But why can't they reproduce the magic? Because they don't have Jessica, or they have someone they hired to be a Jessica, right? But it's not the same.

David

Today, the story behind the magic of Y Combinator. How are you doing?

Jessica

I'm good.

David

Look, um, I'm super excited to talk to you today. Um, you've had such a huge impact on startups. You've had a huge impact on me, and you famously have this uncanny ability to just read people really quickly and accurately. And so I really want to dive into a little bit more of your background and kind of where that came from. I'd love to just understand just from the very beginning, where were you born and what was your childhood like growing up?

Jessica

No. Well, I was born in Minneapolis, but I only lived there for a few months because when I was six months old, my parents got divorced. Um, and I moved with my dad to Boston, where he was from. And my childhood, you know, was pretty normal considering I didn't have a mother because I I really was raised by my dad and his mother, my grandmother, who I lived with, I'd live with my grandmother during the week. And my dad lived about a mile and a half away. And I'd go to my dad's house on weekends and he'd come to dinner at my grandmother's every night. But my childhood was, you know, pretty, pretty standard, pretty happy. Yeah.

David

Tell me more about your dad and your grandmother. What were they like as people?

Jessica

Well, my dad was amazing because you have to imagine a single dad in the 1970s being a parent to a daughter. Like, no dad did that, um, really. And so he raised me. And so I'm like forever grateful. He worked for the Gillette company his entire life. And so I had never known about startups as a result. I thought, you know, what you do is you go work for a big company and you stay there for as long as you can and have a good, you know, retirement plan there and all of that. But my grandmother, his mother, she took me in when she was like 62 years old, if you can believe it. Imagine like raising four kids on your own, and then at 62, I mean, you have kids, bringing in a baby. Yeah. Yeah, start all over again. So I owe so much to her. I mean, because what I found very comforting growing up was that she was always there. I could always count on her. And as a result, she was just such a sort of constant, comforting presence for me. So I was really lucky to have that team of my grandmother and my dad.

David

Do you think there was anything growing up that kind of, you know, you famously have this um sense for people? Like, where do you think that came from? Was it something growing up or was it something that developed later?

Jessica

I think it was growing up. I just, I think, I think it's inborn. A lot of people ask me this question, and I feel a little bit awkward because I don't know if I'm that great at reading people's characters, but from a very young age, because I was an only child, and so I think I had a lot of adults around me. And so I was always trying to, you know, read them and what's going on. And like you could never get anything past me. Like, if an adult tried to sort of brush me off somehow, I'd I'd know that they were trying to do that and I'd ask a lot of questions. I was very inquisitive, and I'm just very interested in human psychology. I don't know, it's in me.

David

Do you remember at that point in time? Like, did you have something you imagined being when you grew up?

Jessica

No, David. I'm gonna be the most boring person you interview because I had no idea what I wanted to do. Everything was uh very near term. It was sort of like, what's next on the schedule here? You know, okay, I'm going to high school now. Okay, next I'm going to college. And I graduated, and some of a lot of my friends had jobs. And I was like, I have no clue what I even am good at or want to do. Like this was in 1993. Okay, so this is before the internet. So you're looking for jobs in a newspaper. I mean, listeners are just gonna die when they hear that. So I came home, and very sadly, like the day after I came home from college, my grandmother passed away of cancer. Um, so that set me off on not a great course. I was sort of very sad, as you can imagine. But I was living at home with my dad, kind of like, oh gosh, what do I even do? And a friend of mine from the town, she had gotten a job in like a training program at Fidelity Investments. So this was on the phones at Fidelity Investments, like customer service. And so I thought, well, I could try it out. I mean, I really, that's how clueless I was just like, I don't even know if I am interested in finance. But I was like on the phones on the night shift in this training program, like taking calls. I mean, what I really didn't like at Fidelity was that they monitored your every action. Like on those phones, they knew how long every call was, how long you were off a call before you took the next call, how long you took going to the bathroom, like everything. And it was very intense, you know?

David

Yeah.

Jessica

And I said, Yeah, this isn't for me.

David

Yeah. Talk to me a little bit about what we kind of that transition from. I'm curious to hear those kind of next few job experiences and then how you first got interested or kind of came upon this idea of startups.

Jessica

Yeah. There really is like no rhyme or reason in my professional background, honestly, to why Combinator. Like everyone always wants to see some clear indication that someone who does something interesting later in life, like always wanted to be that way, or like that I sold lemonade or hustled and made money as a child somehow, or was it entrepreneurial? I was not. I was a hard worker. I will say that. I was like a reliable hard worker. I rarely called in sick. And so my jobs back then, the other thing is like you couldn't have like a gap in your resume or it looked bad. So I never left one job until I had a new one going. Like I almost never had time to think about what I want to do. So I was at this investor relations firm, and that was very interesting. But it was a sweatshop. You know, if you left at 6 p.m., that was an early night. And I remember this one woman I worked with, oh, she was such a phony. And she would stay late, get the free dinner, she'd, you know, charge it to a client. She'd call her family, you know, make all her long distance calls. This is at like 8:30 p.m. And then at, you know, 9 p.m., she'd write an email to all of our bosses saying, just a quick update that I've done this. So, you know, timestamp, she was there at 9 p.m., you know, that kind of thing. And so I was there for a while, but then I was like, this is pretty grim. So after that, I did a total about face and I said, what I really love doing is sort of planning events. So I got a job at Food and Wine magazine, working on their big event out in Aspen every year. I mean, it's just such a hodgepodge of experience, David. You know, for someone who started his startup right out of college like you, you probably can't imagine the like weirdness of going from different job to different job. Then I moved back to Boston, back to my dad's house, and got a job at an investment bank where I worked in their marketing department. And then the bubble burst, and then things started to sort of go downhill. You know, 2003, you could feel it in Boston for sure. And I remember at this point, I had started dating Paul. And I remember saying to Paul, this is just now so not fun working here.

PG

I remember as I was dating her, thinking she is so wasted on this lame investment bank. She worked so hard. I don't think she had ever taken a sick day off, like in her life. I think there was one point where she had the flu and she went home at lunch.

Speaker

Right.

PG

But like she worked so ridiculously hard for them. And, you know, what good does it do? Right. So she definitely seemed like the kind of person you would want to work with for sure.

Jessica

And I said, I need to create like a project for myself that I'm interested in that I can be passionate about, you know. And that's when I started writing Founders at Work. And I did that on the side. And that was fully a result of dating Paul and sort of learning about startups for the first time in my life, talking to him. I didn't know any programmers or people who started a startup. I didn't even know the word startup back then.

David

Do you remember from your perspective how she first got interested in startups?

PG

I think it was from talking to me and all my friends. Because, you know, Robert and Trevor and other people we knew had all been involved with startups. And so talking to us, it seemed like everything was much more random and chaotic and irresponsible. There was clearly something there that you could go and start a company to do something. Where back in the days when starting a company meant having a factory, that was not so easy, right? And now just a couple of people in a room with laptops could do it.

Jessica

And so meeting Paul and his friends, it was very interesting to me, and I became really fascinated by it. And I read Jerry Kaplan's book, Startup, that I was hooked.

David

We'll be right back.

Ad

Keeping up with this economy matters, and in a world full of hot takes and noise, Marketplace does things differently. I'm Kai Rosdal, the host of Marketplace, a daily podcast that delivers independent award-winning journalism dedicated to making you smarter about this economy. You can listen to Marketplace on Spotify.

David

And now back to the interview. Like people being phony, yeah, that corporate work environment. And it sounds like when you found startups, that was kind of like almost the big reveal.

Jessica

Well, here's one of the things that really struck me about startups. What I loved about startups as opposed to when I worked at the investment bank. At the investment bank, on the pecking order, like the marketing group was so far down. And as a result, you know, a lot of people you get treated not super great by some people. Um, who, you know, I was told there, you don't even deserve to work here in a bad market. They shouldn't even have a marketing department, you know, in bad times. And it's sort of demoralizing when people are not that nice to you.

David

For sure.

Jessica

And what I noticed though was like a lot of these people who weren't that nice were also just mediocre sort of players, you know, not that good at what they did. And I thought, why am I working so hard and trying my hardest, working with these people who aren't that good and are unpleasant to work with too? And I thought, that doesn't seem right that the mediocre people are running the show. And what I've observed with startups is like, if there's a mediocre person, they get fired, you know? And the people who, of course, are starting the startup, like it's very rare that a like pure mediocre person starts a startup.

David

Do you so so before we kind of get into starting a YCOM now? I also just want to take a pause and like, do you remember the first time that you met Paul? And do you remember like what your first impressions were?

Jessica

Yes. I mean, unlike my childhood, I have very clear memories of meeting Paul. Let's see. I'm trying to think of where to start. So I at age 30, I was sort of having like a sort of midlife crisis a little bit. You know, my sort of long-term boyfriend and I had broken up, and I was really very sad about that. And I oh, by the way, added on to this layer of misery, I was living at home with my dad and stepmother, which was wonderful. I mean, they were could not have been nicer. But as a 30-year-old, like living in the Boston suburbs with, you know, your family is not that cool. And so I just worked all the time, didn't go out much. Then I said, okay, I gotta get out there. And one thing I did was I took this class at Harvard's Extension School. It was an acting class, David. Oh, wow. I've never taken acting in my life. I mean, the last thing that I had done was like marrying the school play in sixth grade. And I took the acting class because I thought maybe it will help me with public speaking, because I would get very nervous. And so I thought, what the heck? It'll be something to do. So I took this acting class and there was a guy in it who was co-hosting a party with two other people in Cambridge that I was gonna go to. So this guy Marat was my friend from the acting class. He said, Okay, the party's this Saturday. Hope to see you all there. So I show up. I almost didn't go actually, because I was sort of like, oh, my wingman, my friend, wasn't available, who usually would come with me. And so I was going by myself and I was like, I don't even want to go. And I think my dad was like, Really, you need to get out of the house. You should go to this party. So I show up on the doorstep and I'm like, oh, hi, you know, I'm Jessica Livingston, I'm here to see Marat. And the guy who greeted me was like, Marat, he's not here. He joined the Wesley Clark campaign and he moved to Arkansas last week. Didn't he tell you? And I thought, like my heart just sank to my stomach. And I thought, no, he didn't. And I thought, okay, I'm gonna go in, and if I don't know anyone, I'm just gonna like go out the back door and no one will notice. As it turns out, not one person from my acting class was there. I literally went to a party where I did not know one person, and it was at Paul's house. He was the co-host. And I actually didn't chat with him. I thought he was married, actually. He where he I a woman, a friend of his was standing next to him, and I assumed they were married, because I didn't know anyone who lived in a in a nice house, you know, who wasn't married. You know, they all lived in apartments if you're single. Anyway, but I did wind up chatting to Paul.

David

Do you remember when you and Jessica first met? Oh, yes, very vividly.

PG

I was standing in the kitchen and she came back into the kitchen, and I asked her if I should take her coat or if it was part of her outfit. Um, and she remembers thinking that I was sophisticated for for as a man for asking such a question, for being able to know the distinction. It was a long white leather coat. Do you remember like like uh your first impression when you met her? Well, I remember she told me an idea of mine was stupid. Um I have this domain, factomat.com, that I was have been sort of vaguely planning to use for uh a sort of encyclopedia of plausible but fake lies, so that people would like search for it and then repeat the lies, you know, like Ulysses S. Grant had a wooden leg or something like that. Like just about plausible, right? And she said she thought it was a stupid idea. So I was impressed that she stood up to me about that. I still haven't done it. But I thought she seemed happy. She smiled a lot.

Jessica

And then he asked me out. He got my email from the the third co-host and he asked me out on Monday. And we went out on a date that weekend, and that was it.

David

And so it sounds like you kind of got immersed in this, in this group of, you know, startup optimism. I mean, that was post-doc-com days. There was a huge amount of skepticism back then. I mean, I remember this dot-com hangover was real, but somehow you guys decided, like, no, we really, you know, love this idea of startups. And where did the idea come from to say, you know, hey, maybe we should start something to help startups?

Jessica

Yeah, well, that that's another part of the story of our relationship. Because I think I mentioned that I was kind of getting bored at the investment bank and I was working on this book, Founders at Work on the Side. And then I became aware of a position that they were looking for at a venture capitalist firm, a VC firm in Boston, was looking for a director of marketing. And I thought, well, that sounds kind of interesting. I'm gonna go interview for that. But they took a long time. And in hindsight, it was probably only two months, but it still felt like a long time.

PG

And like VCs do, they were taking forever to make up their mind. And meanwhile, every night I was telling her, you know what you should do when you go and work for this firm, you should change it in this way and this way and this way.

Jessica

So over the course of those two months, Paul and I would go out to dinner every night. And he would, you know what you should do me. You know, that's when he waggles his finger at you and says, You know what you should do. And he gives you an idea. And we he would just tell me all about, you know, the VC industry is broken. They want to give, you know, five, 10 million dollars to a company when really all you need to do is pay the rent, you know, was getting much cheaper to start a startup because this is in 2004. You really, if you were a programmer, you kind of just needed a laptop to start, you know, a software company. Right. So it's getting cheaper. In Boston, especially, there was no way to get funding except to go to VCs, which again really wanted to invest large sums of money, and you had to have a business plan. Um, but Paul really felt like there was this huge, untapped source of programmers who could start startups if someone helped them along at the earliest stages, because he had been helped that way when he was getting started with Via Web. There was a guy in Boston who's a friend of his and he was a lawyer by trade. So he not only provided their first $10,000 of funding, but he also filled out all the legal paperwork and incorporated them. And, you know, Paul was like, wow, that's amazing. And that's all that they needed to get started to test their idea. That's the thing. You don't need $10 million. You need, you know, back then you only needed a small amount to live, you know, and then you can get funding.

PG

We made the thing that we wished had existed when we were doing our startup via web. We wished there had been somewhere we could get a small amount of money without too much trouble and advice about how to start a startup because we knew nothing. We knew that there would be a need for something like this because we had needed it.

Jessica

So we would talk for hours and hours about how this ecosystem could be improved and how you could do a lot of events to bring people together, to educate them. Um, because remember, back in 2004, there wasn't that much information on startups. It was not a thing. So um, this was going on in the background. The VC was, you know, taking some time to decide. And Paul, one night we were out at dinner, and I think we were walking home, and he was like, Oh, fuck it. Let's just start our own thing.

PG

I remember the exact point on the sidewalk in Cambridge where we decided to do this because it was a large amount of money at the time. But I said, like, you know, I forget exactly what it was, but maybe $100,000 or something like that. It seemed like a lot at the time. And I said, you know what? I'll put up the money for this and you can work for it, and we'll just start our own.

Jessica

And so he thought, you know, if Jessica and I start our own investment gig, you know, I'll work with the star. Up on their ideas, and Jessica will, you know, run everything else. Um, and that's kind of how the seed started.

David

More after the break.

Ad

Business and the ways we do it are changing in ways that are both more subtle and more radical than you realize. Welcome to Compound Interest from Samafor Business. I'm Liz Hoffman. And I'm Rohan Gaswamy. We've been covering the forces behind this revolution, but now we want to talk directly to the people driving that change. Each week, we'll talk to the operators, the experts, and the innovators to go beyond the headlines. We'll dig into everything from hospitality companies that no longer own hotels to companies that will finance through sushi order. We'll unpack the transformation of how business and consumers engage with our economy and figure out what lies ahead. Listen to Compound Interest from Semaphore Business wherever you get your podcasts.

David

And we're back. There's so much that was really distinctive about YC, kind of as you guys getting started. And listening to your story, there's so much about almost what you learned from your past about what you didn't want things to be like and how you wanted to do it differently. One of the things that was so distinctive that I remember really blew people's minds was just this 10-minute interview. And if you have a 10-minute interview, like you don't have months to look at spreadsheets and decks. I mean, so much of your quick assessment that you have to make is the read on the people. How did you guys decide on just that super short interview?

Jessica

Well, a lot of what we did was we tried something out and we improved upon it. So Paul also had a bunch of other like very important ideas. In addition to only giving small amounts of funding, he also said you can't drag the fundraising process on for you know weeks and months. And I agreed, you know, you got to meet with someone and decide then if you want to invest. Because the longer an investor can drag out the process, the more information that they have on that startup. So they're always motivated to drag out that process. So we said we're not gonna do that. And what we decided was because all four of us had never been angel investors, we said, well, we gotta do something to like bring us up to speed and learn how to angel invest. Let's this summer we'll start off by we'll fund a couple at the same time. And then we called a bunch of people to come interview. And that was a thing. I think interviews were at least 30 minutes back then, David. Possibly 45 minutes. I can't remember. But after the first day, we said, you do not need 45 minutes at this stage. Like we knew five minutes into the interview, you know, whether they were yes or no. And so the rest was just sort of painfully long. And you know, Paul's a pretty impatient person. So it would just didn't make sense to sit there for 45 minutes.

David

Do you have any kind of memories from those really early interviews?

Jessica

Well, I do. I mean, I remember with Steve and Alexis, they had come up from UVA. Paul had met them at the How to Start a Startup talk at Harvard. They had like taken the train up to see him give that talk and then applied to Y Combinator. And they were doing this idea. It was ordering food on your cell phone. Go figure. But it was like, you know, 10 years too early, or maybe not 10 years, but you know, it was a few years too early for that idea. Um, because this is before smartphones were even around. And they, of course, had no connections to any food companies. They're like, you can walk into McDonald's having ordered your food and just pick it up. And we thought, great idea, but we just don't see this happening. So we rejected them. But I remember I loved them. I just thought that they were just so earnest. I mean, Alexis is obviously so charismatic. And it was just, we loved talking to them, you know, and and we were impressed with them. Because their idea, even though it was a few years too early, it was a good idea ultimately. But we rejected them. Because at that point, we did not realize that when you fund an early stage startup, it's more about the founders than the idea. We thought it was about the idea. So I distinctly remember how much I just enjoyed talking to them.

PG

And she was bummed that we turned them down. She really liked those guys. And so I thought, oh, Jessica's sad. I need to figure out how to make Jessica not sad. Maybe there's some way we can accept them after all. I know. I'll call them and say we'll fund them if they'll do this other thing.

Jessica

And then the next Monday, Paul reached out to them and was like, we really liked you guys. Do you think we could maybe brainstorm a new idea? And they literally got off the train in Connecticut and got back on a train to Boston. And they came up with the idea for Reddit then and they were in our batch.

David

When did that social radar talent first become apparent? Like, was there one interview, or was it just kind of a process where you're like, oh wow, her judgment is really good?

PG

During the first round of interviews, we went into it thinking that Jessica would just be almost like a clerical worker or something like that in the interviews, because me and Robert and Trevor were the experts, and we were going to interview these guys and decide if we were going to fund them or not, right? And Jessica was sitting there, like almost like keeping track of who they were and going to get to get the next one, right? And in the course of the interviews, we found we were like starting to like listen to our opinion a lot. So the first set of interviews, and that was, I suppose, when I started, when I realized that she was the social radar too. Cause she would look at these people and say, These guys are good. I don't like these ones, you know.

David

You know, so much of what makes YCYC was these like short 10-minute interviews where you had your read on people. It was the events. You know, I really remember just how warm and nurturing of an environment it was for a you know, a smart young founder that was kind of stepping away and doing something interesting. And then also just, you know, I think a lot of what you really brought is also that nurturing element. I mean, how how much of that was planned from the get-go, or how much of that was just kind of follow what felt right and what you learned from your past in terms of what you didn't want things to be like?

Jessica

Yeah, that was all just play it by ear and do what feels right. I was very nurturing. And this was, you know, before I had my own children, I had so much energy to focus on others. And I really like I really did treat these people we funded like my kids sometimes. I mean, we would take them out to dinner, you know, I would talk to them about, oh, you've just broken up with your boyfriend or girlfriend, you know, I'm so sorry, what happened? I'd check on the like I really genuinely cared. I really did. I mean, it got hard to do as we funded more and more people. But in the first few batches, there were eight startups, you know, there weren't that many people. Every Tuesday night when he we'd have dinner, that felt to me like inviting them into our home, even though it wasn't actually our home, but it felt like a home. Inviting them in, I would have gone to Whole Foods and bought all the food and the special, you know, the cookies and lemonade. Do you remember the lemonade we'd always have and everything? And Paul would physically cook the dinner. He was the chef for many years before that became too much. And we realized like he can't chop the onions and advise startups at the same time. So we gotta cook in. But like it really was like a dinner party, and we did care. And we weren't, we were not ever doing it specifically for the money. It was more doing it to see if it worked. Do you know what I mean? Obviously, we wanted to make money because we couldn't keep going if we didn't make money, but that's not what drove us. It sounds so cheesy to say that, but it is true.

PG

It was just the natural sort of thing we would have done. Did it seem unnatural? Of course not. That was just like if we funded people, we didn't know how investors worked. We'd never like been around any investors. We were in Boston. And so we just did what seemed natural to us. And it was in fact very different from the way things had been done previously, but we didn't even know how different. It just seemed natural to us to act the way we did. Like we weren't like acting nice to you guys to, you know, in order to manipulate you.

Speaker

Right.

David

We were just being nice. It's such a critical component, and it's just so interesting how you know her experience with planning events is a critical part of what made YCYC.

PG

Yeah. And if you think of what YC is like, it's just all a bunch of events, isn't it? Right. What do you do in YC? You have to decide who to fund. And then during the batch, the batch is just a bunch of events. There's the dinners, there's demo day, which is just an event, startup school is an event. YC like consists of events. And so it just turned out, I didn't really realize it at the time. But as essentially a professional event organizer, she had the perfect expertise. Plus, being the social radar, she was the perfect person to do the first part, too, which is deciding who to pick. So it was luck. It was luck.

David

She just turned out to be the perfect person for this. What do you think people sometimes miss about what Jessica's contributed to YC? Oh my God, they miss everything.

PG

YC feels like a family when you go there, which is very different from anything that could be produced by VCs, right? Without being super creepy. And it's like a family. The dinner is in the batch, and she's the mom. So what could be more important than that? She's the one who makes it feel like a family. And even now, even now, people copy YC and they don't get that, right? Like so there's so many copies of YC now. But why can't they reproduce the magic? Because they don't have Jessica, or they have someone they hired to be a Jessica, right? But it's not the same. I mean, paint a picture of what do you think YC would have been without Jessica? It wouldn't have existed. It wouldn't have existed. I would never have thought of starting it without her. I mean, someone said almost insultingly, like Paul Graham started Y Combinator to give his girlfriend a job. In a sense, it was true because she was applying for the job at this place that was going to waste her and ignore her, just like her current employer did. And I thought, she's so good, we should start our own and she can work for that one instead. But I never would, I wouldn't have started it otherwise. Because, you know, we used to call her Jessica the Incorporator. Um, like she she got Dropbox Incorporated, all these companies back in the day. She was this de facto peril eagle. She's very organized about shit like that, which is good because neither me nor Robert nor Trevor are. Someone had to be. She was the organized one. She was the one who like got our bank accounts and was in charge of everything.

David

I mean, so it obviously worked. You know, YC's funded some of the biggest companies, you know, of the time. I mean, just to name a few, you have Airbnb, you have DoorDash, you have Stripe, you have Coinbase, Instacart, Dropbox. We talked about Reddit. I mean, these are just the list goes on and on, literally. You know, I don't know how often you just take a moment, but I think it's 5,000 companies, and the companies are worth almost a trillion dollars total between all the companies. I mean, did you I mean, just reflect on that? Like, did you ever think that that's where things would end up when you started this way back in Cambridge?

Jessica

I definitely didn't. I mean, we we were just we had like low standards. We would have been excited if like when Google bought one of our startups, you know, we were delighted. We were so psyched. You know, we had very low expectations. And like I remember thinking when we started, you know, one of the things Paul wrote in an essay was, you know, don't just join Microsoft, start a startup and get Microsoft to buy you. Like that could be a new way to do things for young people, you know, like starting a startup shouldn't be so weird. And I remember thinking, like, oh gosh, that would be really exciting if, you know, Microsoft actually bought one of our startups. But could you imagine if one of our companies went public? That's the holy grail. Like, so it seemed, it just seemed crazy at the time to think that that could ever happen.

PG

You would have had to be some sort of insane, insanely arrogant person to imagine then that it would become what it has been. We were, we, we had a lot of luck. We were doing what we were doing at exactly the right moment to be doing it, right? Betting on young founders instead of MBAs. You know, this was exactly the turning point when it was happening. It was amazing luck that Jessica was the perfect person to do this. I didn't know how perfect she was. All I knew is she seemed to be really hardworking, you know? But it turned out she had all these other skills that were perfect too. But I can tell you the secret. Here's the secret to doing a startup with your girlfriend or spouse or partner. It's really good if you have complementary expertise. So Jessica and I, like Jessica is a really good judge of character. I'm a terrible judge of character. Everybody tricks me. I'm fairly good at like programming and math and stuff like that. And Jessica is not so not so good at programming and math, right? And Jessica's really good at organizing events, and I don't know, don't know anything about organizing events. And so the things we would do didn't overlap. We would completely defer to the other one. Do you know in the entire history of our relationship, we never once had an argument about Y Combinator? Never once. We had arguments about the things other couples have arguments about, like in-laws and stuff like that, but never once about Y Combinator.

David

Wow, that's actually incredible. Like I would I would have imagined being a couple and then working together in a business that somehow there'd be more friction there.

PG

There would be if your if your abilities overlapped. But ours don't. We're completely complementary. And that was another totally lucky thing. The two of us fit together like this sort of jigsaw puzzle or something. And the resulting shape was the perfect thing to run something like that.

David

How have you seen Jessica grow, you know, from those early days grow as a person and as a founder throughout the years?

PG

Um like I thought she was great and like worth starting a whole thing just to employ. But um, she, you know, she like felt like she had to go and work for whoever would have her, you know. Like I was indignant that this investment bank she worked for didn't seem to appreciate her, but more indignant than she was, I think. But gradually she's gotten more confident after 20 years. Still, still, I would say her big secret is she like, you know, she's a big deal in the startup world. And like secretly she still worries that she's a nobody and that everybody overlooks her, which at least makes her nice and modest, unlike most big deals in the venture business. But it's not really accurate, is it?

David

Was there ever a moment where it like all kind of hit you, like looking at all the impacts of everything that you've done?

Jessica

Well, I mean, it it did happen sort of gradually. So, I mean, it hits me now. I think of that, I practically want to cry. And of course, what impacts me is how many lives we've affected, and not just people's professional lives, but their personal lives and their best friends and people who were in their weddings, and people who didn't know each other and helped people with like health crises in the Y Combinator community and all the good things that happen as a result of these people that we funded, not all of whom are successful, you know, a lot of these startups died, but those individuals, the alumni, are still part of the community. And that's what I sometimes am just staggered by. It makes me really proud and happy.

David

Well, thank you so much for doing the show today. You've had such an impact on so many people's lives. And I did want to end just by saying thank you for taking a chance on three college kids from Penn State all the way back in 2007. Um, because Weebly would not have been what it turned out to be without you, without Paul, and without YC. And it certainly had a big impact on my life. So thank you for starting YC and all the work that you put into it. Um, and and look what it turned out to be today.

Jessica

Oh, thank you, David. I'm so glad we funded you all those years ago. And I'm just so glad to see how you've grown up and where you are now. I'm I'm like a proud mom.

David

This podcast is brought to you by Leap Forward Ventures, an investor in early stage startups. If you like the show, the number one thing you'll want to do is sign up to get notified when we release new episodes that includes transcripts and key takeaways from each story. Head to leapforward.fm to sign up. I'd also love to hear your feedback on the episode and who you want to hear from next. Just shoot us a text at 415-915-3050 to get in touch. This episode was produced by Theo Balcom and Kim Naderfane Petersa. Craig Ellie is our engineer. Reese Laudano made our cover art. Music is by Jim Brumberg and Ben Landsverk of Wonderly. I'm David Rusenko, and this is the Leap Forward Podcast. See you next episode.

PG

She has a bunch of nicknames. Um, Detective Livingston, for example. It's disconcerting to live with her because anything that's off or strange or different than you'd expect, she notices and digs in like the strangest things. You leave some random piece of junk in the bathroom and she's like, What's this? Why is this here? And so you could imagine how useful that would be in judging startups, right? Because they're coming to do interviews. A lot of them basically try to lie their way through the interview while they're not lying their way past Detective Livingston.