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.
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.
I'm Jessica Livingston. I'm a co-founder at Y Combinator.
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's 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.
I'm Paul Graham and I'm Jessica Livingston's husband.
What do you think people sometimes miss about what Jessica's contributed to YC?
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.
Today, the story behind the magic of Y Combinator.
How are you doing?
Look, I'm super excited to talk to you today. 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?
Oh, well, I was born in Minneapolis, but I only lived there for a few months because when I was 6 months old, my parents got divorced. 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 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 standard, pretty happy.
Yeah. Tell me more about your dad and your grandmother. What were they like as people?
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. 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 in diapers. 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.
Do you think there was anything growing up that kind of, you know, you famously have this sense for people, like where do you think that came from? Was it something growing up or was it something that developed later?
I think it was growing up. I just 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 know that they were trying to do that and I'd ask a lot of questions. I was very inquisitive. I'm just very interested in human psychology. I don't know. It's in me.
Do you remember at that point in time like did you have something you imagined being when you grew up?
No, David. I'm going to be the most boring person you interview because I had no idea what I wanted to do. Everything was 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 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 the newspaper. I mean, listeners are just going to 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. 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.
And I said, 'Yeah, this isn't for me.'
Talk to me a little bit about what 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.
Yeah, there really is like no rhyme or reason in my professional background honestly to Y 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 sweat shop. You know, if you left at 6:00 p.m., that was an early night. And I remember this one woman I worked with, 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, 9:00 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, time stamp, she was there at 9:00 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, 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'd started dating Paul. And I remember saying to Paul, this is just now so not fun working here.
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, right? But like she worked so ridiculously hard for them and you know what good does it do, right? So she definitely seems like the kind of person you would want to work with for sure.
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.
Do you remember from your perspective how she first got interested in startups?
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. 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. I was hooked.
We'll be right back.
And now back to the interview.
It sounds like startups, I mean, the way that you described your early work experience, you almost you learned a lot that you eventually brought to Y Combinator, but you also learned some of the stuff that you didn't like, like people being phony in that corporate work environment. And it sounds like when you found startups that was kind of like almost the big reveal.
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 got treated not super great by some people 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 for sure. 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.
So, so before we kind of get into starting a Y Combinator, 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?
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 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 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 got to 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 Mary in 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 going to go to. So this guy Morat 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 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, I'm Jessica Livingston. I'm here to see Morat. And the guy who greeted me was like, Morat, 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 going to go in and if I don't know anyone, I'm just going to 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 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.
Do you remember when you and Jessica first met?
Oh, yes. Very vividly. 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. And she remembers thinking that I was sophisticated 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 your first impression when you met her?
Well, I remember she told me an idea of mine was stupid. I have this domain facto.com that I was I've been sort of vaguely planning to use for 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 and 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.
And then he asked me out. He got my email from the third co-host and he asked me out on Monday and we went out on a date that weekend. That was it.
