The Untold Stories of Y Combinator with Co-Founder Jessica Livingston

It'll be quick. There's not much to it.

I always felt like you grew up in the Northeast. Is that correct? Like, what, you know, what was growing up like for you? I grew up.

in a town called Wellesley outside of Boston, typical, you know, nice suburb. And I had a little bit of an unconventional childhood in that my parents were divorced got divorced when I was six months old. My father raised me. My mother left.

So my father raised me, but because he was working, I lived with my grandmother, his mother, down the road all during the week, and she was essentially my mother. And, you know, in the seventies now, of course, that wouldn't be unconventional at all, would it? But back in the seventies, it was very strange. Like, I didn't know anyone who didn't have a mom.

But for the most part, it was a pretty conventional childhood outside of of that. I, you know, had a lot of friends at school. Academically, I worked really hard when I was young, and I liked sports. I was pretty typical typical Yeah. Kid. What kind of sports did you play? You know, in elementary school, I played everything. I was excited about everything.

But then as I got older and into high school, I played soccer, and I played goalkeeper in in soccer.

And I really I really liked that. That was sort of my focus. What did your dad do for work? Like, how how did you sort of you know, obviously, now and since you've just become literally the social radar for what business is and could be, you know, what was that interaction like if you had to reflect on that? This is why it's so strange. I mean, I'm I'm so.

grateful that I finally got involved in startups, and I always feel like I got involved in startups, like, fifteen years too late because my dad, believe it or not, worked at the same company for his entire career. He worked at the Gillette company, and he did various things.

He worked for different divisions, so it wasn't like the exact same job for thirty five years or forty years or however long he worked. But he always worked for Gillette, and he commuted in with a suit every day. And, you know, I mean, it was great because it was very predictable, and he was home for dinner and, you know, didn't work on weekends.

So it was, you know, very good for me as his as his only child at the time. So we were really close, but that's what seemed normal to me. Like, I never knew anyone. I barely I don't even know if I knew anyone who, like, had their own business, much less a startup.

And in fact, I have told this story once before, but when I decided with Paul to start Y Combinator, I remember the most scary part about it was just telling my father that I was, like, quitting my job at an investment bank that had all benefits and had a secure salary and all of that.

I remember being so scared to tell him that I was doing this new idea that I couldn't even barely explain because we didn't really even know exactly what it looked like. It was just I'm doing an investment company with Paul. And I remember the first thing he said was he looked at me probably a bit shocked. And then he said, does it have health care coverage?

Like, that's what you care about as a parent. And I, of course, said no, but I'll figure I'll go on COBRA or something. But, yes, he had a very traditional sort of job, that he was very good at, but it was traditional.

Makes sense. Was it, like, marketing or sales, engineering? Like, was there a particular focus? It was all in accounting and finance.

That makes sense. He he is a numbers person and very organized, like, fastidious and organized, and I am not a numbers person. He's sort of appalled how I, you know, I struggle to read a balance sheet sometimes.

After getting to know you over many years, you seem like an extreme people person to me. Were you always like that? Jessica, in high school, was that what was that like? That's an interesting question because high school was sort of unique.

I will say I was a people person. I had lots of friends. I always liked people. And because I grew up as an only child, I really depended on these friends. And I, you know, I'd have lots of sleepovers, or I'd stay over at friends' houses all the time. So I was always doing stuff with friends because it was, you know, kinda lonely at home.

But when I got into high school, I wasn't quite as much of a people person, I think. I went to this boarding school that was very academically rigorous. And unfortunately for me, I don't I think it was too much for me.

I I had gone to a school that, you know, I was a straight a student, did very well, and then switching to this this much more difficult school, I struggled and sort of lost my confidence. So I I think I became less of a people person in high school, but then in college, I was pretty social in college.

I spent a lot of time socializing, and I did I laugh a lot because when people ask about the social radar, you know, do you learn this sort of thing? I don't first of all, I don't know what I don't think I can read people all that well. Maybe better than Paul, you know, Paul, my husband.

But I will admit that in college, I did spend an extraordinary amount of time analyzing situations, romantic situations with my friends and, oh, what do you think he meant by that? Or, you know, just spending a lot of time. I'm always drawn to people's personalities and.

what's going on. So I I that is definitely that interest is innate.

It is funny how in, like, social settings, there's so much can be communicated in, like, the turn of a phrase or just nonverbal communication just like, did you see the way that person, you know, looked at or and even during YC, I I always thought it was fascinating how the ten minute interview was so powerful because you could tell so much about a person even in an incredibly short amount of time.

Oh my god. So much information.

If you're looking for it, you know, so much information like body language. You know? I I often tell people, like, we'd have we'd be doing an interview. I remember there was one where someone the cofounder was talking, and the other person literally put their arm in front of them and said, I'll take that question. Like, basically, shut up.

And and I'm sure that person, like, didn't mean to do that, but there's so much body language and sort of expressions.

say a lot too. What would you say to, I don't know, the 16 or 18 year old version of yourself? Like, if you just explained what happened in over the course of your career and life thus far, like, that be surprising to you?

Oh, very surprising. I would say I mean, honestly, when I was 16, I was pretty lost. I just and I think it's because I I wasn't great at school anymore, and I didn't have a project. I just sort of didn't I just felt sort of unmoored for many years, actually. And, you know, it was very clear to me that, like, I was I I just sort of felt like an outcast, sort of like a bit of a loser.

And I've written about this in a blog post I did called Grow the Puzzle Around You, which essentially was a little bit the most autobiographical thing I've ever written, and it really is to inspire other people. Like, if I can become successful at doing something like this, you can too. Because I guarantee you, the teachers in my high school, I'm sure had written me off as totally irrelevant.

And, like, I never would have been voted most likely to succeed. I was not I I bet teachers wouldn't even remember my name if you said it or who I was. I was that, you know, I just blended in. I mean, if I could send a little message back to me, I would change a lot. I I mean, the first thing I'd say is like, it's gonna get easier. I don't know.

And I'd say focus focus on your schoolwork because you are pretty smart. And if you just I think I got so insecure about not about struggling that I didn't know how to ask for help. And so I would have told myself, like, focus on getting better grades. And I wish I honestly wish I had sort of learned to build things back then or learned to program. As you know, I'm I'm in my fifties now.

I just I I never say never, but I really don't think it's in the cards for me to program. You know? I'll just ask Paul to do it or one of the many other programmers I know. But I wish I had experimented with that. I wish I had experimented with all sorts of different, you know, studies and fields, and I just I totally gave up on math.

I dropped math after junior year, never took it again, swore it off. And then when I went to college, I just didn't work hard. I I think I'd tell myself, maybe take a gap year and sort yourself out for a year. Just take a little breather, and get energized to go back to college because I really I kinda squandered my college years a little bit, not working hard.

And then strangely and I graduated which with a degree in English, which is not really that practical. Can't do a whole lot with that. Although I tell Paul this all the time. I say, I do think it helped me with writing, at least practicing.

But I remember when I first started working, I got a job at Fidelity Investments right out of college because, Gary, Fidelity was a big company in Boston, and that's what I knew. You know? My dad had worked at Gillette, also based in Boston. For me, I didn't know what I wanted to do, and a friend was like, well, they have a training program. Why don't you go work there?

And I just sort of thought, okay. Well, that's safe. You know? I trust that. So when I started working at Fidelity, I loved working. It, like, changed ever. I just felt like I felt like trying hard. I felt like doing a good job.

And I really, really enjoyed sort of focusing during the day at what I was doing and then not having to, like, write papers or, you know, study for exams and things like that. I mean, chose you in some respect then. It sounds like Randomly.

What was that process like? I mean, because even by college, like, graduation's coming, like, all the different options sort of, like, unfold, and then it sounds like that there was a program for leadership really spoke to you. Or just, like, man it's, like, sort of, like, a program scary. Oh, I don't know. Scary. A program for leadership? Oh, I don't know.

I mean, it sounded like there was, like, a thing that you wanted to do. Like, you were like, oh, here's a thing that I could go start in start in. I don't know. No. People like programs.

Let me be clear. I'm playing when you say finance, we're playing fast and loose with the, like, definition. I was in, like, a customer service call center for mutual mutual funds at Fidelity Investments. So Okay.

If you own, you know, the long term growth fund or Magellan fund or whatever, Contra fund, you know, and you and and actually, I started out at the lowest point you could, customer service. I couldn't even make a trade. Customer service, you wanted to change the beneficiary on your account? I took care of that. You had wanted to know what your account was worth or change your address?

I did all of that. You know? And if I couldn't help couldn't help you, I'd transfer to the brokerage department to do the trades, or you wanted to make a new investment, transfer you to the sales. So and oh, by the way, it was the night shift. It was like well, it wasn't fully the night shift. It was 03:30PM to midnight. That was my shift.

And actually, I was just psyched to have a job and to be getting paid something. You know? I loved getting paid. And there was a nice group. So, like, they train you. That was the great thing about Fidelity is that they bring you on, you know, me with an English major, someone else with something else.

As long as you're a smart person, they'd train you on on on a lot about mutual funds and how everything worked. And then once I was into the organization, that's when I got, as everyone did, you know, a little bit more ambitious.

And I studied for my series six, series seven, and sixty three, which are these brokerage, you know, licensing things that, you know, not not the hardest thing in the world, but I'll see you definitely had to to study at them and passed. And then I was able to move into the sales group and make trades.

And, I mean, it's still a little frightening thinking of me at age 24 advising people on where to put their retirement money or whatever. But, you know, the Fidelity to their credit did teach everyone a lot of things, and and I did that for, like, year and a half or two years. Yeah.

So it was, I guess, a lot of, explaining to people how, like, pretty complicated things work actually and or here's what you should do. Yeah. Although, honestly, mutual funds, which is what I was focused on, I mean, nothing more fancy than that. They're pretty straightforward.

And, you know, there is it it it it's pretty if you distill it down to, you know, if you have a long term time horizon, how risky do you wanna be, that sort of thing. There is it it's not that hard to understand. It's not like I was choosing specific stocks or doing anything more complicated than, like, mutual funds. But it was a great great experience. I got these licenses.

I was able to sort of parlay that experience into my first job where I moved to New York City and worked at an agency. It was like an investor relations agency for health care and biotech companies. And so there, what I did was it was it was in the the late nineties.

So there were a lot of companies going public, a lot of companies getting acquired, and you had to have a, basically, a PR firm that tried to to communicate directly with the mutual fund companies and the fund managers and the research analysts, you know, who are ranking the the stocks and things like that.

And we'd set up quarterly earnings calls, and of course, we're using faxes back then because email was out, but it was just starting to become more adopted. So the the way that the analysts heard, you know, where the companies made announcements to the for their quarterly conference calls was on a fax. So we used to send stuff through a fax machine.

And, you know, put out wrote a million press releases, and, you know, we got media interviews, and it was it was really very interesting. Again, because at the time, late nineties, it was the bubble. Lots of exciting stuff was happening. Basically, I mean, this was even before the Internet. Right? So I all of this is online now, but or maybe it was just beginning.

It was just beginning, and it was it was this company in New York. So it was in, like, 1995. That's when I first used, like, Netscape Navigator.

to find stuff. It was it was just starting to happen. I guess it's interesting to reflect on. That's how people would raise money, and that's how people would get started. And that's how still a lot of people get raise money or get started is they sort of start a business, and then later they have to hire sort of a a PR firm or, a, you know, an agent to go out there and try to raise money for them?

Well, we wouldn't raise money for them. We would like, my job was to call or, you know, to try to.

gather interest. I would set up meetings with research analysts, you know, who would cover Oh, yeah. Companies in the biotech or healthcare space and get meetings with them in hopes that, you know, Morgan Stanley would pick up coverage on this company or, you know, meet with the fund managers, you know, at Fidelity or Warburg, Pincus, and all these companies. Were these public companies? Yeah.

A lot of them, they were either gonna go public soon or they they were public. But back then, I mean, this is in the late nineties, companies were going public. Companies were, like, getting slapped together to go public. It was.

was crazy. Yeah. I guess today, those companies are increasingly staying private. Yeah. Oh, yeah. And then there's all these other ways to keep the companies, like, sort of funded and growing and alive, which is interesting.

And this was before stuff like Sarbanes Oxley and stuff like that. But, you know, I loved being in New York. Very social. Definitely people person there. I was very interested in my job and and writing stuff and, you know, promoting people and, you know, with their constituencies and stuff like that. And I liked it. It was a bit of a it was like long hours, really long hours you'd have to work.

And I but I was young, you know, so I didn't really mind. I'm curious,.

like, what would, you know, the Jessica of that time think of what you know now or what you've seen now? Like, it must have been a shock to think about, okay. Well, here are these public companies, and then here are the people who have money, and then we have to explain to them that the company's good. And then embedded in that is like, shoot. There's, like, demo day in there.

How we help companies or even in our office hours. Like, say this. Don't say that. Right? Like, were you doing that kind of thing back then?

Sometimes. Yeah. I mean, we'd be writing, you know, roadshow presentations. I mean, we wouldn't write it from scratch. We'd be collaborating with the CEO and the CFO. But we you know, there's a lot of of storytelling. I'll say that, and I worked on a few annual reports. So there was a bit of that.

And, you know, press releases, I always joke because they seem so formulaic, but I think they're sort of you a useful thing to be able to concisely and clearly persuade people. I'm not saying I'm very good at persuading people as evidenced by some of my early efforts at YC with the press and stuff, but I enjoyed it.

So after I spent a few years in New York City and sort of I always used to tell people it was a great place to live when I could afford not to be able to afford to live there. Like, I didn't save up a cent. And one thing I wish I could go back and beat myself over my head about was why did I just throw away so much money? Like, why didn't I save my money?

Because what gives people power and flexibility in terms of their career, in my mind now, young people, is having some sort of nest egg that you can fall back on if you ever got fired or laid off. If you wanted to start a startup and you could pay the rent for a year, you'd be able to take a risk.

But when you're living paycheck paycheck to paycheck, which I essentially was, you can't lose that job. You can't leave that job. And I blew through it, you know, like an idiot. You know, I was 25, but I was so irresponsible. So irresponsible. So finally, I decided, you know, I'm gonna go back to Boston where my dad was and still had a lot of friends and stuff there. And what did I do?

Oh, I know what I did. I first, I I worked at this magazine called Food and Wine Magazine. Have you ever heard of it, Gary? I I feel like it's pretty mainstream. Yeah. Totally. And, you know, it would have, like, this big event called every year in Aspen, Colorado called oh my god. The Classic at Aspen.

That's what it was called. And they'd have, like, Jacques Pepin and Emeril Lagasse, Bobby Flay, all these people. And I worked on that for, like, there for, like, nine months, and I loved it. I didn't get paid much. And this is what happened. So I worked on that to do a total change, like get out of the finance world and just sort of do more event and marketing.

And I loved it, but I didn't get paid much. And so then I said, I better go back to Boston, and I moved back in with my dad at that point. And then I got a job. Well, I ran a marathon in between moving and going back to Boston. I sort of spent two months training for a marathon, and I did one and done. Amazing. Checked that off my bucket list. That was in 1998.

Yeah. And then I got a job, ugh, at this consulting company in the automotive industry, but doing their conferences. They had a bunch of conferences, and I would plan those. And I loved it. I loved running events. I don't know.

I don't know why. I just did. That to this day is like a huge part of what YC is. Well, it is. We have software, and we have events, and it's like sort of all of the things, like, are actually have to work together to make it work. Well, this is what I wrote about in grow the puzzle around you. I had this, like, really kind of random background.

and, like, events I could run with an arm, you know, tied behind my And so y c though was so much about events and still is, like you you say. But back when it was just me, Paul, Robert, and Trevor, you know, the events were on a much smaller scale, but they were still events. The dinners were events.

You know, interviews essentially were events because we had people coming in and out the door, and you had to plan the logistics, and what how do you greet people, and have food for them while they're waiting, and all that stuff, and keep everything running on time.

And then we do start up school, which was our big event every year, and that, you know, was couple hundred people, but it would grow every year to hundreds and hundreds till it was like a thousand. And so events were always a very important part of YC, and I was able to do those by myself for many years.

I guess your story, like, really reminds me of, like, you know, at 25, I also '20 yeah. Twenty two to '24, I was definitely spending every dollar I was getting from Microsoft. So That makes me feel better. Advice. I was definitely doing that. And then I also had a, I don't like this anymore. How do I do something very extreme that's, like, different?

And then I was I tried to be a a hip hop photographer for a magazine. Also a magazine. For.

which magazine?

I think it was like I can't remember what it was called. It was like a hip hop magazine out of East Palo Alto. Don't remember the magazine that I did. It was just like, you know, hip hop something rather magazine. But I mean, it wasn't a big magazine.

And then what's funny though is I remember the name of the other magazine the producer did or the guy who I worked for did, and it was Damn Girl magazine, and it was like a pinup magazine. I was like, sorry. I can't work on that one. But.

my gosh. You never told me that. I never knew that about you. Before.

that's why I went to your went to the startup school events with my camera. So I had, like, these big giant, like because that that was my gear that I was, like, trying to turn into an editorial photographer.

Oh my gosh. That was my pipe dream. So And and instead, you started posterous instead. Yep. Yep. This is the thing, though. I think like, I love though I had a sort of random and varied background, I guess, because I am where I am now. Now if I could, like, give myself advice back then, I would have said, first of all, I was a very hard worker, even though in college I was not.

Once I got into the real world and employed, I worked very hard. Well, I should have joined a startup. You know, I couldn't program, but I could do everything else. And, you know, as you know, the early days of a startup, you just have to have someone doing a little bit of everything. And I'm certain I would have been a good early employee at a startup, but I didn't know what they were.

I didn't really know I didn't know anyone who worked at them. You know, it was just completely foreign world to me. And so I think young people are lucky now because even if their even if their direct family aren't involved in startups, it's out there. You can find startups and information about startups much more easily.

I guess the wild thing is there are gonna be people watching this right now who are literally in those shoes, and they're like, oh, what is this thing? How do I get over there? So that's why this is this media is, like, not necessarily for it's for basically us when we were, you know, from twenty or thirty years ago, actually.

Well, then here's here's the advice that I it's it's gonna sound I I'm not joking when I say this, but I'm a little bit joking. Like, I cannot tell you what a loser I felt like in high school and college. Like, just didn't feel very good at anything. Didn't feel very ambitious or interested in much.

I mean, I had friends and I had a lot of fun and all of that, but I just was not very focused on anything. And I don't think people thought that I'd probably accomplish very much. I don't think they had super high hopes for me. And the point is, like, anyone can do what they want later in life if they focus. You know? And it took me a long time.

You know, we didn't start Y Combinator till I was, I think, 33. So I feel like I lost this decade of really an important time in my life. I mean, my twenties were when I had the most energy and was the least distracted as a human being. I mean, if I could have started a startup in my twenties, ugh, I would give anything to go back and be able to do that.

Because now it's like I'm distracted by a million things. I feel like I need to, like, practically take a nap every day. You know, I just, like, do not I I do not have nearly as much focus and energy as I did. But like anyone, if they are okay with the risk and have some, you know, interesting ideas and are open to possibilities,.

I feel like they can do it. I guess one thing that's coming out from this is, you know, there are just so many like, you would find a job and then you would learn something from it, and then you sort of move on, whether it's like communication or working like PR, working with investors, and then and then events.

I mean, Food of Land sound like it was a really fun time, actually, because that was also even seeing like an event at that scale at that level of like Yeah. Taste and was like very.

A very com complex event. They had, a whole team of people that worked all year round on it. You know, I just came in as sort of a intern kind of thing. But the last step on this job thing before y c was that after the automotive consulting conference planning thing, I got a job in the marketing department of a boutique investment bank in Boston.

And for the most part, I I really loved it there because I was doing a little bit of everything. And this this job was like, you know, PR, marketing, writing, press relations, and things. You know, it was all it was just a little bit of everything that I had done. There was a annual, you know, conference at this bank, and it was just it was really fun.

I don't know if the rest of the the bank really valued what we were doing, but I had a really nice boss and liked my team and I sort of enjoyed what we were doing until like the bubble burst and they had all these cutbacks and I'd, you know, fire people. And then, you know, the other people at the investment bank really didn't want any money going to marketing.

And I finally said, this is sort of a drag.

What was doing marketing for that like? Like, who are sort of the people you're trying to reach? And like, what were the messages that actually landed for them?

So the bank was it was called Adams Harkness and Hill, and it was it had been around for a while, but it was very it was a boutique bank. It was very small compared it wasn't like on the level of Goldman Sachs and Morgan Stanley and Merrill Lynch and all those ones. It had traditionally been focused on Boston companies, you know, doing m and a, trading.

You know, they had research analysts, you know, covering companies in certain sectors. It was primarily, like, technology, health care, and consumer companies. But when I joined, they were really trying to expand nationally and change their reputa their sort of I don't wanna say like sleepy reputation, but that's kinda what it was. So expand their reputation, and that was fun. You know?

We and they they my boss came on and got like, a budget kind of for the first time. There was an organized marketing push. And we did this, like, whole advertising campaign in, the red herring. Do you remember that publication? And this is back when people read magazines, you know, paper magazines.

And so we worked on, like, the the the messages we were basically trying to say is like, we can offer you you should choose us as your investment bank because we're just as good as the big the big guys, basically, but you get more personalized service. I forget all of the all of the different things, but we did all these focus groups and just like it was just really interesting.

And we then tried to also, like, promote the different organizations within the bank that had never gotten special special interest in them. Like, I remember the trading floor. Like, let's face it. One trading group it's hard to distinguish trading trading groups at the different banks. They all kind of are doing the same thing. And the traders were what's the right word?

They were a bit of a hardcore group, let's just say. And they weren't as refined, maybe in polite at sometimes as as maybe the investment bankers were. But, you know, they said, look, you know, we wanna be on the cover of Traders Magazine. That's all we care about, you know, to get some legitimacy, you know, amongst their peers and things.

And I remember finally, we got them on the cover of Traders Magazine, and the photo was, like, taken on our trading floor with all it was, like, from way above showing all the traders. And I remember just being like, yes. We finally delivered for these guys. Because I really like the traders, you know, and we wanted to help them, and that was what they had they had wanted. You know? That's awesome.

It's fun. Is is it just like reaching out, getting to the right people, and then boom, there it is? Or We actually worked with a PR firm, this great agency up in Portland, Maine, and they kind of just started we started building a relationship. You know, this Just getting to know people. Just getting to know people. And, you know, can we help you understand, like, just being proactive.

Like, our traders can talk about x y and z. If you ever need someone, please let us know. Oh, and I remember we also got the budget to install a camera on the trading floor. So we could now pitch to CNBC and all of those TV station you know, television shows.

And once we started having our analysts, investment bankers, traders, being interviewed on our bustling trading floor, that was a total game changer.

That's so interesting.

Yeah. So it's all, like, just step by step, you know, trying to get a little bit more little bit more publicity. And then if a reporter's writing something, they need to call someone they can trust will share a few interesting insights. So we got, you know, calls much more often once we once we just started appearing and had that camera capability.

I guess what's emerging is, like, so many of the things that YC became good at, like, sort of came out of a lot of your experiences. Because, like, being able to deal with media or, like, get placement or, like, build those relationships was like a whole thing. Then there's there's, like, media and there's events.

And then when you add software and then you guys you know, all of that together created community, it's like a lot of these things sort of come together a little bit more. It's like sort of magical set of things, really.

Yes. It is a sort of magical set of things that you don't know what these things are gonna be. Like, it depend you know what I mean? Like, anything can be a magical combination. I do hesitate to take any credit with Y Combinator and the media because I really Oh, you're just being modest. No. I'm really not. Like, no one Early then.

I don't know. Us early on. And I just yeah. I feel like when I think back of my relationships with the press and YC, I feel like many were not very good. I don't know. Because it's funny because it went from being desperate for the press to write about Y Combinator, you know, and getting some publicity. And for, like, a year, it was terrific.

And I remember, like, when Stephen Levy wrote I think it was, like was it Newsweek? We got this expose on it was in oh god. Was it in it was the Octoparts. It was the one that they were in. And it was, like, meet the next billionaires. And and I was just like, we've arrived. People know about us. This is so exciting.

And then it was game. So a boot camp for the next tech billionaires in late two thousand seven.

Okay. So 02/2007. Okay. So that's, like, two years later. That's not awful, you know, that we got that two years into things. But then things could get a little antagonistic with the press, and they were always trying to knock us down and, like, I feel like take things we said and twist it around, and I feel like I just have this list of media that I don't like. I don't know.

It's sort of a It's still like that. Someday I'll write about what? Don't worry. It's still like that. Oh, okay. Alright. That makes me feel better. And never start you know, it was always like that.

I don't know. Was it I mean, maybe just they're more tech press now, and they're not all dedicated to being good reporters. They're just wanting to get clicks. I don't know. When you're coming up, you're the golden child,.

and, you know, you people do wanna help. And then at some point, it flips, and then you're the you're the the man or the thing to, like, sort of tear down because there's someone downtrodden, which is, like, I totally get. Like, that's that's like a whole trope for them. But Yeah. It's it's it's fun tearing people down, I guess. You guys did a bad job. I thought you did an incredible job, honestly.

I don't know. It was that the other thing that I I was so maybe someday I'll write about the media from my perspective. The other thing I wanna do someday, I wanna have, like, a start up school reunion on, you know, Carolyn and my podcast, the Social Radars, of, like, all the crazy stories of stuff that went wrong.

Because the startup school every year that we do, there was always some bananas, like, thing that happened. Like, one year when Justin TV had just started Justin TV, there was, like, a bomb threat at Stanford while it was going on. We almost had the whole event shut down.

But I wanna have like a little reunion of of of startup startup school players and reminisce about all the crazy stuff that happened. You should not feel like you were bad at the media stuff. I think that was a really important part early on. What was it like gen was it Jenny eight Lee wrote like an article or.

Oh. What was.

Yes. Jenny eight Lee wrote no. The first article ever written about us was after the first summer, and I think it was Ryan Single. I think that was his name. And he wrote just a very quick little thing, and Sam Altman was in it. And then Jenny Lee, I forget how we even met her, but she came to one of our dinners and or something, and she wrote a pretty nice article about Y Combinator.

And that that was when we really thought, oh gosh. We've now arrived. We've been in the New York Times, and that was heaven.

Even for YC to know that that was meaningful or valuable to work on is, I think, credit to you and what what you worked on before then. I don't know. I mean, everything that came before comes from someplace.

I do I do think that my varied background did I I was able to draw on certain things for Y Combinator. And and to be fair, I did, you know, I did used to invite the press, do a little outreach and invite them all to demo day.

Because I think even if I wasn't good at convincing them why Y Combinator was so great, I think if they came to demo day, they could observe for themselves why Y Combinator was so great. I mean, there was just so much so many novel things back then that people take for granted now, but even demo day.

Think about as an investor, you have to take all these, like, singular meetings, you know, one after the one after another. Imagine being able to con see, you know, ten, twenty, 20 five startups all in one afternoon. You know, that was that was novel. And then, you know, talk to them all there.

And, yeah, we just I feel like a lot of the the things that we did, I think reporters could sort of observe and think, wow. That's pretty different than what's usually going on. Now we're at the point where okay. So you're at the investment bank,.

and then did you leave the investment bank to work on YC?

Or actually, there's, like, a whole story that you have talked about, at least privately with me. Oh, yeah? What? I'm a like, what what? Flybridge Capital Partners. Is that right? So okay. I have to remember the timing because it all gets it gets a little fuzzy.

But, basically, I met Paul in 02/2003. And through Paul and his friends, I was sort of introduced to this whole world of startups, and I immediately was drawn to it. I mean, I just felt like this is so cool and so much more exciting than anything I've ever done or seen. And I decided what was going on at the bank. I mentioned the bubble had burst.

They're making cutbacks, and it just it just became a little bit boring at that point, and I wasn't that enthusiastic about, you know, writing another press release, you know, because I had to fire the person that usually handled that.

So to combat my boredom, I decided to write a book called Founders at Work, and it was based on the Writers at Work series that how they interviewed writers about how they wrote and stuff like that. And I said, there's nothing out there about startups. I read this book called Startup by Jerry Kaplan about his story about the go, and I I was riveted. And I just wanted to hear more of those stories.

It was so crazy. And Paul told me stories about Veoweb, and I remember thinking, this isn't mental. Like, I don't know about this stuff. Most people don't know about this stuff. And so I decided just for a fun distraction for myself, I'd talk to some startup founders. And, you know, I had a little tape recorder, and I interviewed them. And, I mean, I started small.

I didn't have connections at this point, but I sort of would get an introduction. I interviewed Paul and then got a couple introductions. I forget who my first interviewees were. But then I got a book deal. It was actually I got a book deal from O'Reilly, and I got a little advance. And that is when I quit my job.

Because I was getting kind of burnt out from the investment banks, and I wanted to focus on the book. So I got this little advance, and I said, I'm gonna quit. But what had also simultaneously happened was that I had interviewed at this venture capitalist firm.

It was for the director of marketing at their venture capitalist firm, and I sort of felt like be working at a VC is one step closer to an early stage startup, you know, than an investment bank. So I was really interested in this. And they just sort of maybe in hindsight, they didn't take that long, but to me, it felt like they were taking months and months.

And I'd, like, interview with one person. They'd say, great. We'll come back in another two weeks. It just took a long time. And so in this, like, six week period, that is when Paul and I would go out to dinner every night, and we'd be talking you know, he'd be like, oh, well, if you worked in marketing and then at a VC firm, maybe you could convince them to, like, make smaller investments.

You know? Because right now, you know, they put in millions of dollars, but these, you know, young founders just they don't need millions of dollars. They just need enough to pay the rent. And so we'd have all these conversations, And we thought, you know, they could really increase their deal flow by doing events like start up school and all these different things.

And over, you know, six weeks, Paul, that's when he said, you know what? Let's just start something ourselves. And I said, great. And that's when I went and told my dad I was quitting my job and I was there gonna be health care insurance, but I also had the book advance and the book to work on.

So it was sort of like I had this crazy idea with Paul, but also the book, And I'd work on both, like dual track. And I just did not wanna be employed. And I actually did get offered a job at the VC firm, but I had already, you know, decided that this is what I was gonna do.

The best thing I ever did was take that risk, quit my job to start something new, even though it was a little scary and certainly unknown.

The other amazing part of it that I just will tell people in hopes of inspiring them is that if you feel excited about something, to do something where you don't need to have a boss or you don't need to ask permission to do it for yourself, like writing a book, yeah, I had a publisher, but that was being driven by me.

Everything about it was me and I put everything into that book and it turned out really well. But I wasn't constrained in any way by, you know, other employees or, you know, it was just if you feel like you just take the risk, it will pay off. And if it doesn't work out, go back and do it. You'll get hired again doing what you were doing. That's so empowering.

That's that's awesome. That's a perfect message. And save up the nest egg so that you can pay your rent. That sounds right. Can I ask about, like, the first batch? There was Garden Street, obviously. And did you already have the space? Like, I mean, I Oh my gosh.

I'd love to hear about, like, even just from the perspective of you were potentially gonna go into VC, and then this got a bunch of things sort of jogging in your heads. Like, we Yes. This could be done in a different way. But that's still, like, pretty you know, being able to do it a different way is still very different than, like, okay.

Here's the summer founders conference, and this is happening.

Okay. So let me try to recreate this. So we said Paul said, let's just do this ourselves. And the plan was, at first, was that it would be a regular investment company. And Paul, who wanted to be an angel investor and help startups, but you know, he does not like looking at pitches. He does not like taking meetings. He does not like distractions. He didn't want all of that.

So I was gonna run the company and, you know, we'd have an office in Harvard Square, and we'd take meetings and make investments, and he would specifically be there to advise the specific startups. And it was gonna be all his money, and and then he got Robert and Trevor to pitch into. So just be very simple, but asynchronous investing.

But immediately, we thought, well, gosh, none of us really know how to be angel investors. So let's do let's teach ourselves by doing this, like, program this summer. Because I think it was in March, and we thought we have time to catch people as they're graduating from college or are looking for an internship in the summer if they're junior or something. Let's catch the programmers.

Because the whole thing we wanted to fund programmers who might not know about business side of things, but they're good programmers and they could learn the business side of things, like Paul himself had to do. So we said, let's just do a summer summer founders program is what we called it. And Paul, like, cooked up the website. We had, you know, a few questions.

And we said, you know, literally, it just happened all so quickly. We're like, let's, like, put the application out there, and we'll interview people in three weeks or something. Very quick tie time frame. And we'll call it the summer founders program. It'll happen in Cambridge.

And we were gonna use Paul's personal office that he had bought and just had, like, renovated and soundproof so that he could write without any, you know, distractions. And it was the sweetest space. As you remember from being there that February,.

wasn't it just the most fabulous space ever? Oh, yeah. It was perfect. I mean, perfect for dinner and conversation, and it felt like custom designed.

It did, didn't it? It had, like, open kitchen into this living room where we had the table. So then we had the tables built, and they were, like, trestled tables and benches. We had those built. But actually, I think first, before we built the tables and everything, we said, will we be funding anyone? Like, we didn't even know if anyone would show up.

But Paul posted this thing on his website, which and I think it must have gotten on to, like, delicious or /. Because he had been writing essays. That's the only way Y Combinator could get started was that people, programmers specifically, followed Paul Graham because he was an expert in Lisp and he wrote some interesting essays.

So having distribution is a big deal. It's like that Huge deal. Media stuff is important. You know, just just as like for bankers, like, you you have to, like, get into traditional media or Newsweek or different things like that. For hackers, it was it had already gone on on the Internet first.

Yeah. And no one would know to have applied, you know, if that we didn't have this distribution. So that was key that we had this small, you know, niche distribution channel, but it was the niche we were trying to appeal to. Perfect. And lo and behold, we got, like, a bunch of applications. We're like, oh my gosh. There are a lot of people.

So I think we forget how many people we chose, but let's just I think it was something like maybe 15 startups a day. And we had, like, these half an hour long interviews. Maybe they were even forty minutes. I really should go back and and check just to see how long, but they were super long.

And at the end of the weekend oh, so part of this, we said, we're gonna decide that day, and we're gonna call them all and tell them yes or no that night. Because that was one of the things that Paul said should be changed about venture capital is how long it took. You know, how you get strung along, and you just need a decision.

The longer it takes, the more information the investor has, but it can kill a startup. You know? A matter of months can kill a startup. So we interviewed them, called them back that night, and there were, like, seven startups that we were funding. The Reddits were in that batch. Sam Altman was in that batch doing his, like, geolocationcom company before smartphones. Oh my gosh.

He was eight, like no. He wasn't 18, but he was 19. He couldn't even rent a car, but he had to, you know, fly to do deals with the carriers. Like, that's what he was doing that summer, deals with carriers and stuff. And then, you know, Emmett Sheer and Justin Kahn of Twitch were in that doing a calendar app. So, you know, we didn't know what we were doing, Gary.

We just sort of put one foot in front of the other and said, well, we're gonna help them. We're gonna have these dinners once a week. And then Paul would cook the dinner, but I would like I remember I put, like, candles out. We'd light a fire in the fireplace. I'd get cheese from Formaggio Kitchen, lemonade and stuff from Whole Foods. So it was like a dinner party every week.

And these startups would come together and we'd have a guest speaker who we'd, like, scrounge up from our network. I mean, I I think I invited our someone from our investment bank to come talk about m and a. You know? Like, these guys needed to know about m and a. They didn't at that point, but this this is what we're working with. We had patent lawyer and stuff like that.

But it was still the model seemed really interesting, how people would come together once a week and they became friends, and they'd, you know, tell each other about their progress that week. And, you know, Paul would advise them, and I helped incorporate them. I had sort of had to, like cause we wanted to save people the legal fees of having to hire a lawyer.

So we thought and this was totally novel at the time. We said, let's create template documents to incorporate. And there were like seven different documents you needed. But you really it seemed complex, but you really just filled in the blanks here and there. And so I would go sit down with the founders and say, okay. This is what you do, and this is what you have to think about.

How much stock do you wanna allocate, and here's what it means. And then they'd file all the stuff and become companies.

That's so cool. I mean, I guess you just detailed, like, so many different ways where there was, like, an edge or a bug or just, like, a thing that was not quite right about how startups would start or how investors would invest in startups. And then each of those were different enough, like, on their own that they'd be differentiating.

But when you combine them all together, they were sort of this mega punch, I guess Yeah. Just like to the industry.

We were trying to lubricate that fulcrum of the world. You know what I mean? Because there were just all these teeny little hurdles that, you know, young programmers might think were insurmountable, but they're not. And we thought younger people get get started. Now all they need is a is a laptop and pay some hosting fees and stuff, and it was just getting a lot cheaper to start startups.

And we thought younger people should be doing this. They don't need millions of dollars. They just need enough to help them pay the rent and eat and stuff until they can build something to then go on and get more funding. And that that was demo day at the end of the summer.

It's so interesting to to hear this arc because it sounds like the book was one of the first, like, of a sort, a startup because,.

you know, prior to that, you sort of had a boss or you had to, like, sort of be a part of a team or a system that was not your own. And then the book gave you total agency, and then y c was like this another level beyond that Yeah. That, like, has touched everyone. It's, like, so insane.

Turns out I love the freedom. I love working on my own projects, honestly. And had I been more self aware or more in tune with the kind of person I was, I wish I kind of had discovered that when I was 23, but I didn't. But I loved working on my own projects. And with like, I loved working with Paul.

He was so, like, smart and amazing, and we just everything we had so much fun working together, especially when it was just like the two of us. We just, you know, we'd split up for the day. He'd do his thing. I'd do mine. We'd come together at night and continue to talk about it. We talked about YC all the time, always coming up with ideas to improve things.

Because that's that's one of the things that we did at YC. We changed things on the fly. You know, we always were experimenting with trying to improve things. Well, what if we just tweaked this? Would that improve it? And that's why I think I mean, YC's constantly being improved. You're improving it.

You know, a lot of the partners are improving it, but you gotta be open to changing things a little bit. Yeah. Having I mean, having a great cofounder then, it's a that's the proof's in the pudding for your story then too. It's Oh, yeah. Oh my gosh. I think Paul and I were each each other's, like, perfect cofounders because we were so different in many ways, but we were so similar.

We shared the same values. We wanted the same things. We treated people. We had the same, like, moral compass, if you will, but we had totally different skill sets that were so foreign to the other. Like, I don't I think Paul was still, like, amazed that I was able to open up a bank account, you know, like, because that would stop him in the in his tracks.

And, of course, Paul is, like, a genius for startup ideas and things like that. And he's, you know, very much he'll say whatever he thinks needs to be said, and whereas I'm, like, behind the scenes and I don't talk to people, you know, publicly. We're just different different personalities, but it worked perfectly.

So picking the right cofounder is critical. What I'm hearing is like, if you've if you had figured out that you wanted to be a founder or to have agency, like, really deep agency earlier, that would have helped you in, like, sort of all these other respects, like, earlier maybe. And that you had to it had to come to you, like, in this in the way it did.

But people watching often are like, I you know, I don't feel I don't feel like I have ownership over my life. Like, things don't quite feel right. They're not clicking.

I definitely felt like something's not clicking, and I just always felt like I worked to earn money so that I could live. And I, like, live for the weekends or my vacations or whatever. And even though I, like, enjoyed, I guess, what I was doing, I wasn't really that into it, and I certainly wasn't making money from it. That's the thing.

You know, you as a 25 year old, I was working, you know, super long hours, but that didn't affect my salary. You know, I work all weekend on an m and a announcement. All weekend, I remember there was one weekend where I had, like, two hours of sleep for two nights in a row because the deal was being announced.

And we're up, you know, with the investment bankers and the the executives at the company. And my agency made tons of money. And I think, you know, we got an orchid or something, you know, as a thank you. And it's just like, So when I say I wish I had been more in tune with working on my own projects or thinking like and maybe I didn't know enough back then to add any value.

But again, when I was in my twenties, there wasn't the Internet. You couldn't publish any blog posts. So I don't know where I would have published anything if I did have any pearls of wisdom for anyone. But the point is, I wish I had known that I could work at a startup.

I wish that seemed normal to me or or a path that I could have taken because I think it would have been a hell of a lot more interesting. I might have made some more money. And I don't know. I just think for me, it would have been better. The years 02/2005,.

you did your first, then your second sort of summer you know, it was like summer and then winter. Like, what were some of the things that were most surprising about, like, the interviews themselves? Because that's one thing that I realized was very special about YC.

It's like, on the one hand, you know, we give people money and we help them with their business, but part of the reason why we can help a lot of people is that we actually help all these other people too. I mean, the social radar, at least partially, I think, is also the sheer volume of having seen so many smart people and all the things that could go right and could go wrong.

I mean, you think about what a VC does, a VC might meet, like, hundreds of people a year and then fund, like, five of them. And then the ability to read thousands of a thousand applications, like meet hundreds of people, and then like directly work with dozens of people per year over many years.

Like, you see startups in a way that like no like, the reason why venture capitalists do it the way they do it is, like, it's designed for them. It's not designed for, you know, sort of founders, and then you just see so much more. So it's almost like having a radar that only does a turn every year or something as opposed to, like, every five minutes or every two minutes.

Like, you you actually understand what's going on. And maybe that links into, like, what social radar or, like, radar period means. It's just like a frequency and, like, you just see so much more.

Well, I'll tell you what one thing that's interesting, and I hadn't really thought explicitly about it till you just asked me about it, but I had all of these startups that I was working with, helping, advising, seeing fail, seeing succeeds, all of this shit that you just see when you're funding, you know, 80 start ups, hundred start ups.

I mean, by the time I left, the batches were getting pretty big. So you just see a lot of it. But don't forget also that every Tuesday night, we would have a Mark Zuckerberg come or, you know, some famous successful startup come talk. And I was I pulled up my chair, you know, right next to the YC founders in the audience. I never missed a talk because I learned so much from them.

So I have crazy stories coming at me from, like, the YC founders who are just getting started. Then you have the kind of crazy stories in hindsight that were by the way, back when I was there, people were sharing stuff they had never shared publicly. You know? And and because they trusted the YC audience, and we had rule, you're not allowed to tweet about anything that's shared.

And for many years, secrets were kept in the office, in the YC office. So I was learning about it from that end too. Then I did, you know, the Founders at Work book, learned a lot from that. And during startup school, I would often be the one interviewing the speakers. Like, if they didn't wanna prepare a presentation, I'd interview them.

So I loved learning about them from, questions that I had from that. So I was just having all of this input come in, and I think I can't help but wanna do something with that. You know? And I love talking to people. I love hearing about how people overcome adversity in any in any way, but especially in startups. I love hearing stories about that.

I love talking to these super successful famous people who tell me about how they couldn't raise any money because everyone starts out the same way. You know, you're nobody when you start. And it's just I find it very inspirational because I do I've always believed and I still believe that anyone who is sufficiently ambitious and determined and reasonably smart can start a startup.

Like, anyone can do this if they want to. So I just hope, you know, I I like to continue sharing stories from the most successful startups because I just feel like it'll just inspire more people to do it themselves.

Jessica, that's perfect place to end. Thank you so much. This is awesome. Welcome.