How Y Combinator Helped 172 Startups Take Off – With Paul Graham

Want to see how much impact Paul Graham can have a startup? Here are 3 examples from past Mixergy interviews. The first is Alexis Ohanian, who told me that his life changed when he headed to snowy Boston over Spring break so he could hear Graham talk about startups. Graham ended up investing in Alexis’s company through what became the seed funding firm Y Combinator, but the amazing part wasn’t the money. It was that Y Combinator helped him move past a bad business idea that he and his partner spent a year on, and discover a better one, which became Reddit, the social news site that was sold to Conde Nast within 2 years of launching.

Then there’s Kevin Hale who told me that when he interviewed with Y Combinator, he and his co-founders had an idea for an elaborate content management system. During the interview, despite initial resistance, they were convinced to create a form builder instead. The business became Wufoo, the startup that reached profitability within 9 months.

Finally, a few weeks ago, I talked to the founders of AirBnb. When they joined Y Combinator, they had a site that gave travelers an affordable alternative to hotels by matching them with locals who had space in their homes. They had a national presence, but they were constantly struggling for cash. Y Combinator gave them some funding to keep going, but they told me it was Graham’s suggestion that they focus on just one city till they got their product right, which changed everything. Within a few months, they had a better product and they were finally profitable.

How does Graham do it? That’s what I wanted to find out in this interview.

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Paul Graham, Y Combinator

Paul Graham is a partner at Y Combinator, which gives startups seed funding and mentorship. He’s known for his work on a new Lisp dialect called “Arc,” his essays, and for founding and administering Hacker News. Previously, he co-founded Viaweb, which was sold in 1998 and became Yahoo! Store.


Raw transcript

Mixergy's audio transcription is done by Speechpad

Andrew: This interview is sponsored by Wufoo, which makes forms and surveys that you can add to your website right now. Check out It’s also sponsored by, where you can create an online store right now, within five minutes, and have all the features that you need to keep selling online. Check out It’s sponsored by Grasshopper, the virtual phone system that entrepreneurs love because it has all the features that they need and can be managed directly online. Here’s the interview.

Hey, everyone, it’s Andrew Warner, founder of, home of the ambitious upstart. You, guys, know we do here, I interview entrepreneurs about how they built their business to find out what the rest of us can learn from their experiences. Paul, I’m going to ask you about that smile in a minute because I love your feedback on some of the way that I do my interviews here.

Today, I’ve got Paul Graham. He is the co-founder of Y Combinator, which funds and advises startups. He’s also an author whose essays are devoured by entrepreneurs. He’s a hacker who administers Hacker News, and previously, he co-founded Viaweb which he sold to Yahoo. The smile, by the way, that I was asking about, a lot of times, when I do my interviews, I start them off with ‘Home of the ambitious upstart.’ I look at the person who I respect, who I brought on here to do this interview, and I wonder, do you think it’s ridiculous or is this a charming, interesting part of the program? What do you think?

Interviewee: The ambitious upstart part?

Andrew: Yes.

Interviewee: Well, what I was thinking when I heard it is, ‘Oh, good, this is my kind of place.’ I was thinking about whether it was a particularly good marketing tagline.

Andrew: Oh, good. Then, if you think it’s your kind of place, then it is a good tagline for me.

Interviewee: Yes. Ambitious and upstart, that’s exactly what I’m looking for.

Andrew: Perfect! So, as I told you earlier, I’m going to start throwing this as the biography of Y Combinator. Along the way, I’d like to see what you’ve learned as you funded, I think, it’s a 172 startups, you told me?

Interviewee: 172, yes.

Andrew: Wow! It’s a lot. Let’s start off with the essays, since that’s how many entrepreneurs get to know you. Why did you start writing about entrepreneurship?

Interviewee: Well, I write about whatever I’m thinking about, and so I just started thinking about entrepreneurship. I think that started because I had to give a talk to the Undergraduate Computer Society of Harvard. In fact, that’s what Y Combinator grew out of. So if I give a talk to these undergrads, and I thought, ‘What shall I tell them? What can I tell them?’ So I thought, ‘All right, I’ll tell them how to start a startup.’ So I gave them this talk about how to start a startup, and I put it online later as an essay called, ‘How to Start a Startup.’ That, Y Combinator, literally, grew out of that talk.

Andrew: What happened? How does a talk become a revolution?

Interviewee: (laughs) Well, what happened was I was giving them advice, sort of in the real time that they should raise money from angels. The best thing was to raise money from angels who had themselves made their money from doing a startup, because then, they could give you advice as well as money. I noticed that all these guys were looking at me, sort of expectantly, in fact, sort of like baby birds. I was like, ‘Jesus, they’re all going to there to meet their business plans.’ So I said, ‘Not me.’ I had never done any angel investing at that point, and I didn’t want to start.

But you know, then I immediately felt guilty, and I went to dinner with some of them afterwards, and I thought, ‘Even though these guys are just undergrads, I bet a lot of these guys could do it.’ They could figure it out. And so, I thought, ‘All right. All right. I’ll start angel investing.’ So, Y Combinator happened just because I wanted to start angel investing. Originally, Y Combinator was just going to be like regular angel investing, a synchronist, not this whole batch model. We discovered that later by accident.

Andrew: So, who are the original startups that were so good, were so inspiring that you said, ‘I’ve got to back these guys.’

Interviewee: Well, Reddit, the founders of Reddit were at that talk. They came on a train from Virginia.

Andrew: From Virginia, they told me that they got over to see you.

Interviewee: Yes. That’s a long train ride, right? So, I was impressed by their determination, and that was actually why we funded them. They were so determined that they came on the train all the way from Virginia to hear that talk.

Andrew: What else was it about them? I’m sure there are a lot of people now who come and travel a long way to see you. They don’t have that magic. But I talked to Alexis and he said that you didn’t like his original business idea, but you liked something about him to bring him back. I asked him, ‘What it was that Paul Graham saw in him?’ He couldn’t defined it. So now that I’ve got you here, what is it about him? Maybe from there, we can extrapolate.

Interviewee: He and Steve were both smart. They were determined and they seemed flexible. They seemed like they really wanted to start a startup. But you know, it’s a little bit misleading to ask what I like. Jessica, her nickname in Y Combinator is ‘the social radar.’ I actually have bad judgment of character. I’m not good at judging people. I, really, I’m kind of bad at it, and I know I’m bad at it. But, Jessica, she is very rarely wrong.

There’ll be somebody I meet and really like and she says, ‘You know, there’s something off about him.’ And it always turns out she’s right! Always. So, I’ve learned, like when Jessica says, ‘These people are good’ or ‘These people are bad,’ I should really listen. A lot of people don’t realize, strangely enough, I’m actually sitting where the founder sit in Y Combinator interviews. This is what the world looks like. What I see is what the world looks like to them, what’s behind me is the back of the room.

And, we bring these people in for interviews, and I think a lot of them think Jessica is like some kind of a secretary or something like that. She’s the one who sort of smiles at them and greets them and remembers their name.

Interviewee: But you know it’s a little bit misleading to ask what I like, because Jessica is, her nickname in Y-Combinator is “The Social Radar”. I actually have a bad judgment of character. I’m not good at judging people. I really, I’m kind of bad at it. And I know I’m bad at it, right? But Jessica, she is very rarely wrong. They’ll be somebody I meet, and I really like, and she says, “You know, there’s something off about him.” And it always turns out she’s right. Always. So I’ve learned, like when Jessica says these people are good or these people are bad, I should really listen.

Andrew: OK. Let’s pause here and go back a little bit and talk about the people, the people who started Y-Combinator with you.

Interviewee: OK.

Andrew: In that talk, you said that it’s important to get the right team together. And on your team you had, it sounds like from the start, you had Jessica Livingston, who was an investment banker at Adams-Harkness before. You had Robert Morris, who was your partner at Viaweb and a long-time friend.

Interviewee: And Trevor. He worked on Viaweb, too.

Andrew: And Trevor Blackwell from Viaweb, also.

Interviewee: Yeah, it was basically the same three people from VeoWeb.

Andrew: Oh, so Jessica Livingston was at VeoWeb with the Ö I’m sorry, we had a little bit of a lag. Was Jessica Livingston…

Interviewee: No, no.

Andrew: No, she was not. OK, so it was the three of you.

Interviewee: Right.

Andrew: How did you find Jessica Livingston? And what was it…

Interviewee: I was dating…

Andrew: Sorry.

Interviewee: I was going out with here. She was my girlfriend. [conversations cut off]

Andrew: How did you go from girlfriend to partner?

Interviewee: Well, when we were going to start, we were going to start investing, right? And we didn’t know anything about the logistics of investing. You know, she had one of these weird securities licenses that is called a Series 7 or something like that. She actually knows about this whole world. To this day, I have only like skimmed our legal agreements, right? But she keeps this stuff in line. She knows how to do the mechanics of investing, and we didn’t know how to do it. Like, if it hadn’t been the three of us, we never would have started this ourselves, because who would have done all that crap, right? Oh, sorry, who would have done all that very important work?

Andrew: Ha-ha. OK, so we got to know her. How about Robert Morris and Trevor Blackwell? What did they bring to the partnership?

Interviewee: They’re very smart. I mean, they’re the smartest people I know. And they’re also, they’ve done the start up themselves. I mean, they had basically the same experience I do, in the same companies. So, I can work with them, you know.

Andrew: OK…

Interviewee: And Robert, our SysAdmin.

Andrew: I’m sorry.

Interviewee: And Robert is our SysAdmin.

Andrew: I see.

Interviewee: We’re probably the only company that has a full professor at MIT as their grumpy SysAdmin.

Andrew: All right, so let’s go back then. Jessica Livingston sees these guys. She says, ‘I like them, there’s something about them, let’s invest.’

Interviewee: You mean the Reddits?

Andrew: The Reddits.

Interviewee: Right.

Andrew: Yes. So, you guys bring them in. What kind of structure, what kind of support system did you have back then?

Interviewee: It was pretty much the same as now, right? That very first summer, I mean, the reason we decided to invest in start ups in batches, all at once, was because we didn’t know what we were doing. And so we thought, well, you know what we’ll do. We’ll have a summer program, because everybody, I don’t know if you have a programming background, but everybody treats summer jobs as kind of throwaway jobs, as a programmer, right? You’re not expected to get a lot done. It’s just so the company can decide later if they want to hire you after you graduate. So, for both the hirers and the employees, summer jobs are kind of like a throwaway thing. So, we thought, well, as long as everybody treats summer jobs as a throwaway thing, we’ll have this summer program, and if it turns out to be a disaster, no one will blame us, right? We can sort of learn how to be investors, at the same time these guys learn how to be start up founders. And the fastest, the most efficient thing was, since it was going to be a summer program, it was synchronous, right? All these start ups would get founded at once, just like everybody who works at Microsoft for the summer…

Interviewee: Öjust like everybody who works for Microsoft through the summer shows up at about the same time. So, the whole doing things in batch we discovered by accident, but it worked so well we decided, “All right, we’re going to keep doing this, you know, starting batches of starting startups all at once. Initially, though, it was just an accident.

Andrew: What kind of help did you give them as you were doing this? I know about the weekly dinners that Alexis Ohanian said that he got a lot out of. I know that the entrepreneurs got to talk to each other and show each other their progress. What else did you do to support them along the way?

Interviewee: We got all their paperwork done, right? And we got them set up cleanly so if there was some weird ‘gotcha’ about the IP, like they had started working on the thing at their previous employer, you’d tell them no, rewrite that code. And so, by the time they got to the end, the demo day, they were like a clean startup with no weird ‘gotchas’ that would make investors barf. Like former co-founders who were gone but still had 30 percent of the company or, you know, they didn’t own their IP or someone hadn’t signed some agreement or something like that, right? And they hadn’t really properly incorporated as Delaware C-Corps instead of whatever broken LLC they came in with, all that stuff. It’s not nothing, right? That’s actually the kind of stuff Jessica does. Everybody, demo day, everybody is in good shape as a company, right? We also gave them a lot of product advice, and it turned out we had a knack for this from having worked so long making web apps ourselves, I mean, literally since the beginning.

Andrew: How did you do that? That’s another thing that Alexis told me that the idea for Reddit came from you, and a lot of the entrepreneurs have come back and told me


Interviewee: The idea for Reddit was a combination of us and them. We told them we didn’t like their original idea. We said, “Come back and we’ll talk about other ideas”. But we didn’t say, “Look, here is a wire frame. Build this”.

Andrew: I see. Right. You said, “Here’s an idea. Go run with it”, and they did go out there. Actually, it was an idea that you guys came up with together.

Interviewee: Yeah.

Andrew: But, you led them in the direction.

Interviewee: But, they came back. When they came back from the next day and we talked for quite a long time the next day. When we cooked something up in that, we saidÖ I just called them on the phone and said, “We loved you guys even though we rejected you. If you come back, we’ll figure out something new for you to do”.

Andrew: I see. So, how do you do that? I mean, yes, you did create one of the early web apps. Yes, you did create Viaweb and you saw it all the way through to a sale to Yahoo, and you got to see the inside of a big company like Yahoo. But, that still doesn’t seem like enough experience to be able to sit down with an entrepreneur and say, “Here, I’m going to help guide you in that direction. What else was going on?”

Interviewee: You know, I have a weird ability to do this, or something like that. I don’t know why. I often worry that it will stop working, you know, but it’s almost like some weird knack that people have. Like people who can tell you that December 21st, 1960 was a Tuesday. You know what I mean?

Andrew: Mm-hmm.

Interviewee: It’s like that because it’s true. It wasn’t that I had such an enormous amount of experience. Somehow, I seem to be able to look at a web app and think, “No, this is wrong. This is right”. And now, I can say, “Well, it’s because I worked with 172 startups. Now, I have tons of experience, you know, probably more than anybody else”. I seem to always have some kind of natural ability to do this.

Andrew: OK. So, what did you learn from that first class? What did you learn from that first experience of working with a batch of entrepreneurs on new companies?

Interviewee: We learned a lot of stuff, right? We learned some of these things we had done by accident were really good, like funding a whole bunch of startups at once. It’s really good because they can all help one another. We learned that young people can actually successfully start startups. I think in How to Start a Startup” I said, “You know, you should probably be like 24 or 25 or something like that for starting a startup. Some of these guys in that first Y Combinator batch–Sam Alman was 19 and he was the best startup in the batch. So, lo and behold, you can start a startup even younger than we thought which is not to say that’s the only age you want to start a startup. The age range of potentially successful startups extends frighteningly low, right?

Andrew: I think actually you said that the cutoff was 38, and you’re over 38 running essentially a startup with Y Combinator.

Interviewee: No, I’m not. There’s one big difference between Y Combinator and a product company. We do not have customers who can call us at any random time because something is breaking, and that is what makes a startup so hard. The closest thing I have to that is Hacker News. But if Hacker News is down for a day, it wouldn’t be the end of the world, right?

Interviewee: ÖWhereas, Viaweb was down for like ten minutes, (laughs) we have full of really angry people calling us, because there’s a big difference. I can go on vacation, a startup founder cannot go on vacation, because who’s going to watch it?

Andrew: I see. So, I happened to know that the guys from AirB&B prided themselves on getting as many minutes of your time as they could while they were building out their product. But, you’re saying there’s a limit to when they can call you. If they had a question in the middle of the night, at two o’clock, they’d have to wait until the next day to call you.

Interviewee: Yes. I mean, They’re kind of questions that founders to ask me are not usually the kind of things that have to be answered at 2 a.m. I mean, sometimes, they are like if someone is getting acquired or something like that, but even then, guys aren’t doing stuff at two in the morning.

Andrew: Right, and it’s not breaking at two. Well, it might, but not often.

Interviewee: Yes. If it happens at 2 a.m., they’re usually technical problems.

Andrew: All right. So let’s talk about then the second group of people. What did you do differently as you’re assembling that group?

Interviewee: Well, the second batch, the biggest and most obvious thing it was different was we’re in California. We decided, in our second batch, that we would try doing one in California, partly because it was much nicer in California in the winter. So, we could be self-indulgent and also ambitious at the same time. We didn’t want somebody to say, ‘We’re going to be the Y Combinator of Silicon Valley,’ after we started it. We can kind of see, through the year and on, that people would start copying us. In fact, it’s kind of a surprised us it took as long as it did. But we didn’t want somebody to say, ‘We’re the Y Combinator of Silicon Valley.’ We wanted to be the Y Combinator of Silicon Valley.

So we thought, ‘All right, we’ll do a batch out in Silicon Valley.’ We decided, at the last minute, to do it Silicon Valley. The application form for that batch set on it. We don’t know where it’s going to be. It might be in California, it might be in Boston. If you can’t do it in some place, tell us here. The only we could get a space in time was to carve out a piece of Trevor’s robot company building, which is where I’m sitting now. To this day, we’re still in the middle of this robot company. It’s quite kind of entertaining, actually. There’s always these robots strapping around.

Andrew: This is Anybots.

Interviewee: What else do we do differently? Not that much else, really. I mean, it wasn’t a winner. So, there was no question of it being a summer job for people.

Andrew: Did you get the sense, by then, of the kind of entrepreneur you wanted? Maybe there was a kind of entrepreneur that you thought you wanted but wasn’t a good fit.

Interviewee: We were getting better. We gradually got better, and we’re still not very good, even though we’re much better than we were when we first started. But we started to learn, for example, that it mattered a lot how much people actually wanted to do a startup, people who really did think of it just a summer job. You know, at the end of the summer, they will go back to school just like people do in a summer job. So we were starting to learn that determination was the most important thing.

Andrew: How can you find determination? How can you know that somebody is determined for real and not just, ‘This is it.’ It’s not just a temporary thing.

Interviewee: That’s actually our single hardest problem, telling how determined people are. I mean, there are two things we care about ñ how determined people are and how smart they are. We can tell, in a ten-minute interview, how smart someone is. You just like hit a few tennis balls across the net at them and see how hard they hit it back, or if they with entirely. But telling how determined someone is in a ten-minute interview, we are often fooled. Actually, the Y Combinator alumni kind of hose here, because they tell people how to pretend to be determined during the interview. We meet these guys during the interview and they seem like real butt capers. Lo and behold, as the challenges of doing the startup emerge, they kind of fall apart. So, we’re often fooled, it’s hard to tell, it’s hard to tell. You can’t just ask people so, ‘Are you really determined?’ It’s pretty obvious what the answer to that is supposed to be. So, it’s hard.

Andrew: What kind of things does an entrepreneur do to fool you into thinking that they’re really determined?

Interviewee: Well, being seeming really tough and calm during the interview. I mean, why am I telling people about this guy?

Andrew: Because you guys are going to get better, and as long as this information is out there, you might as well get it all the way out there in even playing field.

Interviewee: There’s the danger of life. Matt Maroon of Blue Frog gaming. He was a professional poker player, talk about pokerfaced. So, he came in for his interview and he just seemed like absolutely unflappable. We thought, ‘Boy, this guy is tough. This guy is not a wimp.’ Actually, we were right, he was really tough. But, to this day, he is genuinely unflappable. I probably would want to fund more people who are really good poker players. I’ve noticed, empirically, there seems to be a high correlation between playing poker and being a successful startup founder. That’s how he seemed tough.

Andrew: That’s not fooling you, that’s just he had a calm strong presence about him. What else? Do they tell you specific stories about the time that they sold candy in elementary school?

Interviewee: Oh, yes! Actually, that’s a good one, people have evidence of their determination. So for example, the AirB&B guys, at one point, they were running out of money in their startup, they’d been working on their startup for quite a while before Y Combinator. I think, maybe, around a year or the bulk of the year. At one point, they were out of money.

Interviewee: We thought, boy, this guy is tough, this guy is not a wimp. And actually we were right, he was really tough, right? But like, that’s — to this day he is — he is genuinely unflappable and I probably would want to fund more people who are really good poker players. They’re seem unnoticed [xx] there seems to be a high correlation between playing poker being a successful startup vendor.

Andrew: But then — that’s not —

Interviewee: Yes. (Overlapping conversation)

Andrew: — that’s just he had a calm, strong presence about him.

Interviewee: Yeah.

Andrew: What else? Did they tell you specific stories about the time that they sold candy in elementary school? Did they —

Interviewee: Oh! Yes, actually that’s a good one. If people have [xx] their determinations, so for example the AirBnB guys.

Andrew: Um-hmm.

Interviewee: At one point, they were — you know they were running out of money in their startup, they didn’t work in their startup for quite a while for like how many years, I think maybe around a year or the bulk of year. And at one point they were out of money and they — they made their own package breakfast cereal, within Obama and McCain theme, you could buy either one. And we —

Andrew: Obama always?

Interviewee: Yeah, yeah, I have a box of Obama, it was going to show behind me, in fact. And I’ll tell you, like I think they made like $30,000.00.

Andrew: Um-hmm.

Interviewee: And they’re like design the box.

Andrew: They — they design it, they sold it?

Interviewee: Yeah. You know, as soon as we heard that story, they [xx] basically. There’s — there’s — there’s often a point in the interview where we all kind of look at one another and decide, OK, we’re funding these guys. And at that point the remainder of the interview, we were just chatting. And as soon as — as soon as we heard that story, you know, it was all over it, they were in.

Andrew: What about Kevin Hale and the Wufoo guys? They also had similar experiences, didn’t they? What —

Interviewee: Yeah.

Andrew: — what drew you to them?

Interviewee: They had Particle Tree. They had made Particle Tree and I knew Particle Tree. I don’t know how I knew it but I knew about this website and I knew it was really good. So I knew they could make things, you know, and they were not just thinking, oh, maybe we’ll start a startup. And then a few months later they will say, oh maybe we won’t, all right? Obviously they were — they had some practice during the project [xx] and they could work well together, you know.

Andrew: I see. So, maybe one of the — one of the ways —

Interviewee: All of the Wufoo guys were terribly nervous during their interview.

Andrew: Were they?

Interviewee: Yeah. Oh, they were so nervous. I mean we — we tried everything we can to make people calm during the interview. We now we have people, like waiting outside, sort of talking calmly to term — for the interview because we don’t want people to be flustered during the interview. Our goal was not to try and break them. If people are nervous, all it does it add noise to the interview, right?

Andrew: Um-hmm.

Interviewee: We need — need all the signal strengths we can get, so we want people to be calm. But this, the — you know, the Wufoos were only our second batch, and we didn’t have anything to, like help people be calm or we didn’t write this — we didn’t write these instructions about how to ease your interview or anything like that. Now there are such things, we sent the people that like how they do well in the interview, right? The Wufoos were so nervous, and after the interview, like, you know, reactions were divided about whether to fund them I said no, they’re not stupid, they were just nervous. And it’s true, that was it, they were just nervous.

Andrew: And there is another situation where Kevin told me that he had one vision for what he want to do and you had another. You said, oh, what you’re looking to build the forms? And he said no, not forms, forms are these ugly things, it don’t make sense, nobody wants to be in — in the form based — in the form business and he said no. Program said this is the opportunity, in fact, he said I think that that the guys at Y Combinator, he didn’t just say you, but the people sitting — sitting across the table from him helped him come up with the —

Interviewee: In the interview?

Andrew: Yes.

Interviewee: [xx] happens that the idea for the startup, yeah it’s crystallized even in that ten-minute interview. I mean what we start — what we do in the interview, we don’t like to ask so, where do you see yourself in five years or [xx] always around there some crap like that? I mean what we do in the interview is we just start doing Y Combinator. The first ten minutes of Y Combinator is the ten minutes of the interview, right? And so, if we like a group like we just start. OK, what about this interview, what about this, have you tried this, right? And that’s why people come out of the interview thinking like, oh my god, they asked us so many questions. Our goal isn’t to — like badging them with questions and see what happens. The goal was like to figure out the startup, right? And that’s why they’re so many questions, what should the startup do? It’s a momentous question.

Andrew: I see.

Interviewee: You’re going to spend like years of working on this.

Andrew: I see. Then, how do you know of the — if the business idea is going to be big enough? How do you know if there was enough money in the form business? How do you know if there’s — if there is enough of a market around ready or do you even know that?

Interviewee: We don’t — we don’t know that and we don’t worry about that — that really. We don’t care that much about the idea. I mean, it would be bad if it wasn’t obviously terrible idea, right? Like —

Interviewee: Like start a new search engine with no features that are any different from Google, right? It’s like if someone was determined to do that as their idea, we would reject them. Like, I mean, they’d be stupid. We should reject them. But unless it’s an obviously terrible idea it’s not the idea that’s important. At this stage we care about the founders. We’re going to have three months to figure out the perfect variant of the idea.

Andrew: Okay. Did you, by the way, get into search? I think you did, right? One of your start ups was going to get into search.

Interviewee: It’s okay if people are doing a search that’s not exactly the same thing as Google. So, for example, Octipart does electronic part search. Those guys are really good, so that’s search. And there’s a start up in the current batch that hasn’t launched yet. Or at least hasn’t outed themselves. It’s Y-C that’s doing search. But again, it’s a specific vertical. That’s okay. That’s fine.

Andrew: Okay. Yeah and Web…I never know how to pronounce them even though I use this…

Interviewee: Web mind.

Andrew: Web mind! That’s how you pronounce them? Web M-Y-N-D? Of course! Web Mynd! They’re the…

Interviewee: `They don’t do search themselves. Well, they do sort of do search. Yeah, they put search over on the right hand side of Google search.

Andrew: Yeah, they enhance Google search.

Interviewee: Yeah. Yeah. Okay. So they do do search.

Andrew: Okay.

Interviewee: It’s funny. I think of them as this sort of plug in for Google but they do actually…they do have to do some amount of search to make that work.

Andrew: Okay. I don’t want to stay too much on Woo Fu but I know them best because I’ve used them for years so let’s continue there. You decided to back them. Did you have, at the time, an idea for an exit or did you say this is an interesting…

Interviewee: No.

Andrew: No. What was your thinking in the future here? For the future?

Interviewee: …take care of themselves. We don’t have…It’s so impossible to predict something like that. You know, the founders themselves don’t know. Think of all the stories about…like Larry and Sergei, right? They funded this company, I don’t know, founded this company that’s worth something like 200 billion. I don’t know what Google’s market cap is but it’s gigantic and when they first started out they were walking around to the existing search engines trying to sell the technology to them for a couple million, right? So if someone…if the founders themselves can be off by like many orders of magnitude about the exit, it’s stupid to even think about it. You just want to fund people who are good and some of them will go public and some of them will just like explode on the starting line and there’s not much you can do about them.

Andrew: Okay. And then…so then they went through the program. They had a product at the end and then you and Paul Buheit invested in them. At that point did you say, ‘Now I see an exit for myself? Now I see that these guys can go public or be sold.’ Is it important…?

Interviewee: No. Even then, even then you can’t predict exits. They really are genuinely unpredictable. And it’s better just to not think about it.

Andrew: To just say, ‘This is a good business. I see it growing, I’ll support them.’

Interviewee: Yeah. ‘These guys are good.’ And, you know, if they have some kind of exit at some point in the future, it’ll be good for them. So we have… we’re all in the same boat. We have the same kind of stock, right? So you have to assume that if they do something that’s good for them it’ll be good for you too.

Andrew: Okay. All right. So let’s suppose somebody’s listening to this and says, ‘Man, Paul Graham is incredible. He can help shape an idea, he can help draw out the best in you. I don’t have Paul Graham in my neighbourhood. Or maybe I’m too old to fit the criteria or maybe I just want to fund the business myself. How can I find somebody like Paul Graham?’

Interviewee: Well, the first two don’t matter, right? Like you don’t have Paul Graham in your neighbourhood? Most of the people who do Y-Combinator don’t come from the Bay area. They come from all over. They come from all over the world. So that doesn’t matter. And the thing about age, that doesn’t matter either. We funded a bunch of people over forty. I don’t think we’ve ever funded anybody over 50 but some of the most successful start ups have been founded by people over 40. The third thing, like you’re determined to fund the company yourself. Well, why? If we’re willing to give you money why not take it, right? I suppose you might not like the dilution but a lot of people think it’s a good deal. So really, you could, if you wanted to, in all those cases. But if someone wanted to find someone local to advise their start up I guess the best thing to do would be to do what I suggested in that original talk about how to start a start up. Find somebody’s who’s done it themselves. And that’s the person to ask.

Andrew: I see. A lot of people don’t have this gift. A lot of people can’t, if you bring them an idea, rattle off a solution. I watched Jason [INAUDIBLE] on This Week in Start Up, some guy will call up with an idea and he’ll kind of bat the idea back and forth with them and brainstorm until there’s something that’s fundable there. There aren’t a lot of people who can do that. How do you find those people?

Interviewee: You know, I don’t know. I don’t know.

Andrew: How important do you think it is?

Interviewee: Obviously it’s very important, right, if that’s what you’re looking for from the guy. And if your idea is not already perfect ñ if your idea is perfect then any start up founder can tell you, ‘Okay, here’s how to approach VC’s. Here’s the right point to hire people. Here’s what not to do.’ But if you still need to work on the idea then you need to find somebody who can munge ideas. I don’t know. I don’t know actually how you could recognize people like that.


Interviewee : if your idea is perfect, than any startup founder can tell you ok here’s how to approach VCD’s, here’s the right point to hire people, here’s what not to do. But if you still need to work on the idea then you need to find somebody who can munge ideas, and I don’t know, I don’t know actually how you could actually recognize people like that. Because there’s probably a lot of people, there’s probably a lot of people who do it badly and as a founder how could you tell the difference between someone who did it well and did it badly right? You can’t. So I don’t know, I don’t know. Apply …(inaudible)…

Andrew : Here’s something that I noticed about you from your writing. You seem to be looking for a formula for success in entrepreneurship, that you’ll try to list all the reasons why companies fail and then hopefully at the end you’ll be left with reasons that they succeed or you try to figure out…

Interviewee : yeah..

Andrew : ..what it specifically takes. Am I reading it right?

Interviewee : Well.. whenever you’re writing an essay you don’t wanna just like do a lot of hand waving and you know, never get to the point. You wanna, I.. my goal in writing any essay is to make the strongest statement that you can make without being false. Right?

Andrew : Uh huh, uh huh.

Interviewee : So whenever I’m writing anything I’m trying to think, all right what do I tell people here? What’s the.. How do you get to the heart of the matter? And so it’s not just in the essay’s about startups, everything I write, I try and get, I try and figure out what the heart of the matter is otherwise it’s useless.

Andrew : But are you also trying to find formulas.. is there a formula here that people could apply, could say, look this is a guy who’s, who’s now worked with 177 startups, did I get that right or 172? My handwriting stinks.

Interviewee : 172

Andrew : 172, let me make that clear on my paper. He probably knows the formula at this point, or if he doesn’t, when he hits 372 he’ll have the formula. Do you agree..

Interviewee : No

Andrew : at that point there will be one?

Interviewee : No, no. There is not like a formula. Like you know a bulleted, a sort of itemized list of stuff we could suggest to people, do this, do that. Startups vary, right? But there are definitely some patterns. There are some things that work and some things that if you do them then they are going to hose you, right? So.. launching pretty fast, almost always works. Like being highly engaged with your customers almost always works. Sitting around spending a long time noodling on the idea is almost always a mistake. It’s like a form of procrastination that you can convince yourself is work.

Andrew : I see. Ok.. Alright let’s take a look at some of the questions people put up on hacker news. Max Kline is asking about your personality and I noticed it here too. Is it always this calm? Do you lose it?

Interviewee : No.. I’m not always this calm. I saw that question too and he asked like if I threw chairs? No I definitely don’t throw chairs, like if I’m really mad I’ll, I’ll just sort of talk calmly to someone, like this.

Andrew : I see.. I’ve heard people, here’s the thing a lot of our entrepreneurs are now studying you for years, they’re in this community, you’re the leader of this hacker news community of entrepreneurs who are developers… If you, if you don’t like their ideas or disapprove of their progress or if they perceive that either of those are true, they’re, they’re hurt. I’ve talked to a few people who felt that way. What are you noticing?

Interviewee : Did it help? When I disapproved did it seem like a wake up call or did it merely depress them?

Andrew : I don’t know.. I know that some…

Interviewee : Well it’s a big difference right? If it’s a wake up call that’s good. If it merely depresses them that’s bad.

Andrew : Well I don’t know that I can make sweeping generalizations, I haven’t had that many conversations, like that. But yeah..

Interviewee : Well if you find out let me know.. I’m trying to get better at this.

Andrew : You are. Are you active in trying to get better at the way you communicate with them?

Interviewee : Oh yes!

Andrew : How? What have you done that helps you communicate with them better? How do you bring out the best in people?

Interviewee : Well… One thing I’ve been trying to figure out is how to tell which people to keep nagging and which people to give up on right? Cause you know there are some people, when.. basically we made a mistake. There’s always going to be some, we get to demo day and like we know they’re not going to raise money and they probably know they’re not going to raise money and they’re gonna like go back and get jobs. You know there’s always some percentage that are just doomed. And so the ones that are doomed it’s just tormenting them for me to keep nagging them and encouraging them, right? Cause they’re not going to make it, and so whereas there are others who are on the borderline, who you know might be, might fail and might succeed. And then if I nag them and nag them and nag them I can maybe push them over the threshold, right? And so it’s one of these situations where right on this threshold you have two extremes of what you want to do. The ones, the guys who are just good enough you want to nag enormously and the ones who are not going to be good enough you want to nag not at all. Right? It’s not a continuous function, there’s a step there, so it’s kinda hard to optimize, but I spend some time thinking about that. And I, we spend time…


Interviewee: We spend time thinking about all aspects of why a company is better. Not just how to give people advice, but how to pick products, how to match them up with investors, it’s all new. Most of the stuff we’re dealing is stuff that people haven’t done in exactly that form before. So we can’t help thinking about how to try and do it better because we’re so bad at it.

Andrew: Really? Really!? So you still consider yourself bad at it?

Interviewee: Oh god yes, we think of ourselves as just utterly terrible at picking these terms.

Andrew: Why? What’s bad about it?

Interviewee: Because our choices are always wrong! That’s why. We have tons of evidence of how bad we are.

Andrew: What are your percentages of bad companies to good ones, would you say?

Interviewee: At least a third are just disastrous, you know. In the venture business generally a lot of the investments are failures. Even a venture fund which has a lot more at stake and spends a lot more on effort in due diligence than our ten minute interviews. Even a venture fund half the investments will be failures. So everyone in the venture business is bad, right? And maybe if we had more experience in the venture business we would take this badness for granted and think “oh well, actually we’re really good if only half of our investments are failures”, but we’re not in the venture business so it seems intolerable.

Andrew: So the four of you might sit around maybe with some entrepreneurs and try to bat around ideas about why that…

Interviewee: Amongst ourselves. Amongst ourselves. We talk about like start ups that we picked that we were really glad we picked. We say “how do we recognize more people like that?” And, there are start ups that we were fooled by and we think “how do we stop being fooled in the future?”, you know? We learned a lot by interviewing Woofoo. We learned how to tell the difference between people who are nervous and people who are lame. And we were figuring that out in that interview, so we get better from practice.

Andrew: Okay, what about the bad ones? What have you noticed that is disastrous? What kind of people?

Interviewee: Wimps.

Andrew: Wimps?

Interviewee: Yea.

Andrew: What is a wimp like?

Interviewee: They have a certain body language. You should really ask Jessica. Jessica is the expert at telling when people are going to wimp out. She’s so much more sensitive to this. She has much more natural ability and like, when we were writing code in college, she was judging people’s characters, right? So, both by nature and by training she is so much better than I am. Like if I want to know if someone’s a wimp, basically the high bit is ask Jessica. She’s the one who will tell you.

Andrew: I do have to have her here on mixergy. I don’t know if you know, back when I had a book case behind me for I guess the first year of doing these interviews, I often put her book behind me, “Founders at work”, knowing that if somebody saw my interview and recognized “Founders at work” even though the cover was a little blurry and it was hidden behind, well it wasn’t hidden, but it was a little hard to see, but if they recognized it and they loved it, then they’re the kind of people I want in my tribe here on Mixergy.

Interviewee: Yea, yea, same with us actually. That book was, I mean the way she chose who to interview for that book was who we ourselves wanted to hear the stories about.

Andrew: How did that factor in to Y Combinator, the book itself?

Interviewee: She was working on “Founders at Work” before we started Y Combinator. The book came before Y Combinator and it was part of the reason we started it. That was one of the reasons I was thinking about start ups so much. Because for a long time I didn’t think that much about start ups. I was working on programming languages and then spam filters, you know? But I was talking to her about it for that.

Andrew: I see, so she was telling you what she saw? What was it about that that inspired you to look into start ups? What was it about the stories she was collecting?

Interviewee: It wasn’t so much the specific story. She hadn’t done a lot of interviews yet, but she was sort of thinking about this book. We were talking about who she might go with for the interview and so we were just talking a lot about what start ups are really like and she, she didn’t really know what start ups were really like. For example, one of the big mistakes that people make about start ups, people out in the real world, even founders to some extent, they think like it starts because there’s some brilliant idea. Like, you know, success is for-destined. And I told her, “no the idea changes a lot, people start out they’re not even sure they want to start a company”, and Google is the perfect example of this, right? And so I would tell her what things were actually like in the start up world, and she was shocked. Yet, she had worked for this investment bank that thought of itself as being involved with technology companies and no one in the company had a clue what start ups were really like. You know? So she was just astonished to hear all of these stories from us and other start up founders who knew about what things were really like.

Andrew: Is that how you met? When she…

F: Is that how you met?

Andrew: When she — well, no, she didn’t come to him; she met her before she even wrote the book.

Interviewee: Oh, yeah. I’ve known her for — I think we’d been dating for over a year before YC got started.

Andrew: OK. I am going to go to another question from that [xx] lot of interesting questions here. If a Y Combinator company becomes a lifestyle company, can you guys still profit from the business? Or do you need —

Interviewee: No.

Andrew: No.

Interviewee: No. I mean there’s got to be an exit for it, equity holders to get any money. I mean, maybe — maybe in the future there is some model where companies pay dividends instead of an exit that like we’ve never tried to get anybody to do that, and we don’t have any real hopes about it. So, no.

Andrew: OK. So you are thinking when you are investing, you’d at least — you’d like to be able to sell out the company. You’re personally invested —

Interviewee: [xx] the public, right.

Andrew: They’ll go public.

Interviewee: There’s got to be some sort of liquidity, you know, in getting bought and going public [xx] two big firms’ liquidity. Now they — although there is evolution in this world, look at Facebook. Facebook’s stock is liquid, right, and they’ve either been bought or got public. So, who know what will happen in the future? In that effect, there is no difference [xx] investing. The only way you are getting money out of a startup is some sort of liquidity.

Andrew: I see. Why the name Y Combinator?

Interviewee: It’s a trick in the lambda calculus. It’s a programming trick.

Andrew: Oh.

Interviewee: And I — I realized later that it had — it was related to what we do, that the Y Combinator is sort of self-referential in the way that Y Combinator is.

Andrew: Hum.

Interviewee: But initially I called the — I wanted to call it Y Combinator just because I thought the Y Combinator was a really cool thing. And so it would be the — it would be the perfect name for picking out the kind of people who we wanted, right. Hackers would look at this and think, Y that’s so cool, they’ve named it after Y Combinator. There must be something going on here. I am like students would look at it and think, Y Combinator what’s that, you know? And that was what we wanted. We wanted hackers to notice us and see we didn’t care.

Andrew: I see. And apparently it’s working. Well, I noticed you guys, but I didn’t know what the meaning was. Actually, I’ve got to be honest, I still don’t understand it. And I even saw it in Wikipedia before I did this interview. That probably would be the wrong person for you guys to back then —

Interviewee: No. Well, the Y Combinator is notoriously one of the most contorted ideas in computer science.

Andrew: OK.

Interviewee: It’s — it’s kind of thing you — you wouldn’t even think that something like this would be possible, you know.

Andrew: Hum.

Interviewee: And I myself like whenever — I can’t like sit down and write out the Y Combinator for you in lambda calculus. I have to look it up too, you know.

Andrew: OK.

Interviewee: Not the kind of thing you actually use in day to day programming very much. It’s more of — it’s more of mathematical interest than practical interest.

Andrew: OK. What about this? All the companies you guys back within three months are able to get this beautiful user experience; I always know instantly what they are about. I always can navigate them quickly; and —

Interviewee: Yeah.

Andrew: — they look beautiful — so beautiful that I want to — that I’d be proud to show them as my own website if I owned them. Within three months are able to do that. How do you do that? How do you get that user experience?

Interviewee: I mean, I nag — I mean, some of them — some of them are great already, but the ones that aren’t great, I nag and I say, look, what is — like, people showing it at some website, they don’t care about it as much as you, the founders, care about it, right.

Andrew: Um-hmm.

Interviewee: So — and — and they don’t — what you care about with most web apps is the person who shows up randomly. You don’t care about the person who has already signed up for your service. They are already sold. All they need is a little log-in button up in the right hand corner, right. So, what you care about is the person who randomly clicks on your website and has their fingers poised over the back button. Because think how many websites you visit every day, and most of them are no good; you know, you just click on back and then you go on with your life, right. So, you’re designing your website for the guy who is just about to leave, he is just on the cusp of like even caring what you do, right. And he — like you do know what your website does but he doesn’t, and he doesn’t even care that much. So you have to tell him. You have to say, this website is about such and such, right. And you have to tell him what he is supposed to do there, you know. The button we want you to click on is this big red one in the upper left hand corner. That’s what we want you to do, you know. So, at least he knows what he is supposed to do, you know. I don’t want to click on it before I do, but — the thing that kills you is ambivalence, where he is like, I don’t even know what this website is about. How many times have you like clicked on some website and you think, what is this startup even for, you know?

Andrew: But there is the curse of knowledge, as I think they said in the book Made to Stick, that you work so hard on this site, you understand everything about it to try to simplify it for somebody who is brand new. It’s really hard there, and then to do it all in such a short period of time to figure out design is tuff. Do you have somebody on board who does that?

Interviewee: Right — yes.

Andrew: Sorry.

Interviewee: No. It’s just like writing an essay. You have this big complicated situation, you need to boil it down to its essentials. So I just look at the startup and I think like if I were writing something about it, how would I describe it, right? This is the essential thing. This is what they should say. We don’t have a graphic designer on staff, although we have been thinking of it. We have a lawyer now. We have a lawyer on retainer, who like fixes the startups ordinary everyday legal problems, and that turns out to be huge. That is great. That has saved so much money in trouble. So we are thinking of getting a graphic designer on retainer too, it’s just we haven’t got around to it yet.

Andrew: …is tough. Do you guys have somebody on board who does that?

Interviewee: No. It’s just like writing an essay. You have this big complicated situation, you need to boil it down to its essentials. So I just look at the start up and think like, if I were writing something about it how I describe it, right? This is the essential thing. This is what they should say. We don’t have a graphic designer on staff although we’ve been thinking of it. We have a lawyer now. We have a lawyer on retainer who fixes the start ups’ ordinary, everyday legal problems. And that turns out to be huge. That is great. That has saved so much money and trouble. So we’re thinking of getting a graphic designer on retainer too but we just haven’t got around to it yet.

Andrew: I notice that you have legal documents, and you’ve had for a long time available to entrepreneurs, documents that they can use for investors and documents I guess, that they use along that process. What about a set of documents for entrepreneurs who are just starting to team up? Where they can help spread the ownership of the company properly, where they can ensure that they each own the IP?

Interviewee: We have that.

Andrew: You do have that?

Interviewee: Yeah…I think that…paperwork on line. I mean, maybe it isn’t but I thought it was. I think it is. Yeah, I think it is. …for starting a company in the series documents.

Andrew: I’m sorry so we just lost the connection for a little bit. So if I and this guy Wallflower on Hacker News decided to partner up because we liked the way we’ve exchanged ideas here in the Comments, we can go to Y-Combinator, get a legal document that we can use to split up ownership of the business and then start working?

Interviewee: I think so.

Andrew: Okay. I’ll have to look and if somebody in the chat room knows I’d love to see what you guys think of that. I’d love to see if you can find it and maybe link us to it.

Interviewee: Go to Google and search for ‘series A Y-Combinator’. That’s what it’s called. Series A. Yeah, I think so.

Andrew: How do you find a partner? If you’re just working on your own and you’re to team up with, how

Interviewee: and so the two biggest ways people find co-founders is to go to school with them or to work with them at the same company. Because you don’t really know what someone’s going to be like until you’ve worked with them on stuff. They might seem smart but, you know, they’ll turn out to be flakes or something like that. So what I would tell people, I think having a cofounder is very important. We’ve seen tons of evidence of this. We do fund some number of single founder start-ups and they do worse than start-ups with multiple founders. And there’s a lot of empirical evidence too. If you look at all the start-ups the technology companies that are most successful very few of them have single founders. Even companies that seem now like they have one guy, like Oracle, initially they had more than one founder, right? He just came to the fore. Same with Microsoft. Or Apple. Initially you need a couple guys to spread the load over. So having a co-founder is very important. So what I would do is if you don’t have a co-founder, find a co-founder. Because we not having a co-founder is going to kill you. That’s the part that’s going to kill you. Fix the part that’s going to kill you. Spend six months trying to find somebody that you can work with and then do the start-up instead of rushing into it unprepared.

Andrew: I see. So find somebody who you can maybe work with on a small project, maybe on Hacker News. Maybe at Bar Camp or some other event.

Interviewee: And the project you work with does not have to be the start-up. It’s just as well if it isn’t because then you don’t have to figure out how to…like who’s in charge of what and how to split the intellectual property or what to work on. Just work together with them on some open source projects for a couple months and then you’ll know if they’re good.

Andrew: All right. Let’s talk about Hacker News. Why did you launch Hacker News?

Interviewee: Well, originally I just wanted some kind of application to test this new programming language, Arc On. If you’re going to write a programming language you ought to write some kind of application in it to make sure it’s actually good for writing programs. So I wanted to write some kind of program in it. And I had tried to convince the Reddits to create a sub-Reddit for start-ups and they were like talking forever to make up their mind about how…what was the right way to implement sub-Reddits. They took out a long time to figure out how to do sub-Reddits. They had the [Joel] sub-Reddit first and that was a one-off. But like general purpose sub-Reddits where you could create them about any topic was much later. So eventually, this combination of the desire to write some kind of application in Arc and be getting tired of the waiting for the Reddits to make a start-up sub-Reddit made me decide I would start a website about start-up news. And that’s what Hacker News was originally called. It was originally called Start-Up News but after six months we changed it to Hacker News because we got sick of reading about nothing but start-up stuff.

Andrew: So was it to find new stories for yourself or did you have a vision for what this community would do?

Interviewee: Well, we already had a whole bunch of Y-C founders at that point. We probably had like 150, 200 founders. And so we had this community of people who were interested in the same stories and they were the original users of Start-Up News. It was sort of like a news aggregator for those 200 people.

Interviewee: [49:55] Well, we already had a whole bunch of YC founders at that point. We probably had like 150-200 founders. And so we had this community of people who were interested in the same stories. And they were the original users of ‘Startup News’. It was sort of like a news aggregator for those 200 people.

Andrew: I see. OK. And who’s managing it now? Who’s deciding what stories get killed? Who’s the person behind…

Interviewee: Me.

Andrew: That’s you.

Interviewee: There’s a bunch of editors, but it’s shocking. Probably one of the biggest surprises in my life is how much time gets sucked up by Hacker News. There is just so much crap. You know, and there’s enormous amounts of spam, there’s a thousand and one varieties of semi-trolls, some of them well-meaning, some of them just crazy. God, they suck up a lot of time. The whole site just sucks up a lot of time. And I try to automate as much as I can, but it’s not that automatable.

Andrew: Is there a payoff in that? I mean, with all the work that you’re spending there?

Interviewee: Well, I mean, it’s a great source of people applying to [xx] I think. I never tried to track it. It means that huge numbers of hackers spend every day looking at this little orange ‘Y’ up in the left-hand corner. Right? That can’t be bad. At least people know about us. So I think it’s good, but I’ve never actually tried to measure whether it’s good. It’s more like, it just got started and I got sucked into working on it. And now I spend too much time on it, but what am I going to do, shut it down? So, I didn’t really make any conscious decisions about it.

Andrew: Who are the other editors?

Interviewee: YC founders. I think there are around 30 of them. So they’re all people I know and trust and they have good judgment and care about the site. But I’m not even sure, actually, who they are. I’m not sure which people are editors. There’s something I can go and look at and see who the editors are, but I don’t know.

Andrew: OK. And if there’s somebody whose stories automatically get killed or specific sites that are automatically killed that’s probably you saying ‘No, I don’t want this as part of my community.’

Interviewee: Sites getting killed, anyone can do. Actually, anyone can ban a user too. But usually most of the people who get banned, unless they’re obvious spammers or trolls ñ like really really egregious trolls who are obviously just…they think of themselves as trolls ñ editors will ban them.

Andrew: OK. Can you say why certain sites get banned, even if they are in the hacker space, or in the news space? Are there certain things that you just don’t want, certain kinds of stories that don’t fit?

Interviewee: Well, most of the sites, the huge majority of sites that are banned are just spammers. I don’t think there are an awful lot of sites that are banned that are related to the stuff that gets talked about on Hacker News. We wouldn’t ban a site unless it was… I think is banned, for example. Because it’s crap. It’s deliberately created fluff. I just doubt there’s anything interesting on there, that would engage someone’s intellectual curiosity. But that’s the kind of site that’s not a spammer site that is actually banned. I’m not sure, it might not be banned, I’m not sure.

Andrew: OK. Alright. Let me start asking you a little bit about my work here. I love the community that you’ve built there. That you built on Hacker News and around Y Combinator and the influence that it’s had on this whole space. I feel like, who do I want to reach? I don’t want to get a huge audience; I want to get the right audience. And I’m looking at the people who care about your work and I’m saying, ‘They, to me, are the right audience.’ How can I serve that audience well, Paul, with my interviews?

Interviewee: Well it seems like you are. Because it seems like people… Hacker News, from what you say, it sounds like Hacker News is identical with your audience. So, you seem to be pretty popular on Hacker News, so it seems like you’re doing fine. I don’t think there’s anything you have to change dramatically.

Andrew: I have your kind of curiosity, though, about what it takes to build a successful company, and what the entrepreneurs are thinking of, and who they are. Give a sense of what you like to see, or how to bring that out of entrepreneurs.

Interviewee: Well, you want to ask different questions than news reporters generally ask. There’s all these traditions in the news business that people now take for granted. Of asking sort of shallow questions that create controversy. For example, a classic old-fashioned dumb ass reporter, if they were interviewing Larry and Sergei, they would say, ‘So Larry, what about China?’ Who gives a fuck about China? It’s just some political controversy, there’s nothing intellectually deep about it. What I care about is things like, when did they make the architectural decision to make their search engine work on a whole bunch of crappy cheap computers? That’s important!

That’s not current events and it doesn’t generate a lot of controversy and sort of cheap, short term interest, so I would say, the way to serve this audience, I mean this is the kind of audience that doesn’t go for that kind of crap, mostly, unless, you know, unless like there’s people there I would rather not have there, but be deep. Ask the questions that matter instead of the kind that merely elicit controversy. And it seems like you’re pretty good at that.

Andrew: I’m trying. I do feel like those other stories get more attention. That if I, if I interviewed, for example

Interviewee: Sure, in the short term, yes, sure, but this is a different audience.

Andrew: I see. Okay, is there something

Interviewee: Tell me, like ask, ask the questions that would be helpful to someone starting a start up.

Andrew: Mmhmm. Do you see somebody who does that well now? Who brings out those key moment is entrepreneurs?

Interviewee: You mean an interviewer who asks

Andrew: Yeah an interviewer or writer

Interviewee: those questions. Yeah, you know, I do see someone like that, fairly frequently in fact.

Andrew: [laughter] But she doesn’t, you know what, does she blog? I’d like to see a chapter of the “Next Founders at Work,” every week on her site, I could read that all day long. I know she doesn’t have the time for it, but.

Interviewee: Oh God. You know about these interviews. It takes her more than a week to do one of these interviews.

Andrew: I see. I get that. I wish she had more time to be able to do that. Would you please giver her the space to go and do that?

Interviewee: You know, that is her deepest wish. If she is watching this, she’ll be laughing so much at this point because that’s what she would like the most too to be able to spend more time on the new version of Founders at Work. There’s a new, she’s working on a new edition, with a bunch of new interviews.

Andrew: Oh wow. Really.

Interviewee: Yeah, the big problem in her life is that she has to spend all her time on random crap and doesn’t get to spend time on the book.

Andrew: I’m going to have to ask her

Interviewee: Which is exactly, that’s the problem that everyone has in writing a book, incidentally.

Andrew: That there just isn’t enough time to do it while you’re doing everything else.

Interviewee: Yeah that they end up having, you know, because the book doesn’t have deadlines and other things, like do you have deadlines?

Andrew: Yeah.

Interviewee: Right. This interview happens at a particular time.

Andrew: Yeah, yeah.

Interviewee: And the secret, the crap, crap work has evolved this protective mechanism to not get ignored called deadlines, right? And so if you look at what most people do instead of their great vision for their life, they spend their time doing things that have deadlines.

Andrew: Yeah, like email. Answer it monthly.

Interviewee: Yeah, yeah. So one of the secrets to getting stuff done is to be able to blow off stuff. Even stuff that seems important.

Andrew: I see, piss off some people who have imposed a deadline on you

Interviewee: Yeah

Andrew: just so you can get to the stuff that you really care about.

Interviewee: You got to be, you probably have to piss people off to get really hard work done.

Andrew: Hmm. Alright. Well thank you for doing this interview with me, I’m so glad to finally get to meet you and I hope I get to meet you at some point in person too.

Interviewee: Yeah, you should drop by to dinner. Send me an email.

Andrew: I’d love, I’m still in Buenos Aires but when I’m back in the US, I’d love to come by and

Interviewee: Shit, Buenos Aires!

Andrew: Yeah.

Interviewee: That is the internet for you.

Andrew: Alright, well thank you. If you’re ever down here, we’ll have you over for a steak and a Malbac, if not, I’ll wait till I get back to the U.S.

Interviewee: Alright, thank you very much. Nice talking to you.

Andrew: Thank you and thank you all for watching, if you have any feedback or comments on how can I become a better interviewer, who else should I be interviewing, please, bring it on, I always love to hear that stuff. Bye.

Interviewee: Bye.