How The Author Of “Founders At Work” Helps Y Combinator Discover And Mentor Startups – with Jessica Livingston

How does Jessica Livingston do it? How does she look at new, (usually) unproven entrepreneurs and figure out which of them are worth banking Y Combinator’s money, reputation and mentorship on?

When I asked her co-founder at Y Combinator, Paul Graham, he said she has a “social radar.” “She is very rarely wrong,” he told me.

I invited her to Mixergy to find out what she looks for. How can she tell who’s going to be clever and persistent enough to see a business through to success? And, more importantly, how can you be as perceptive when you’re deciding who to work with?

I also wanted to find out how she wrote one of my favorite books on entrepreneurship, “Founders at Work,” a collection of interviews about how the founders of admired companies like Apple and Adobe launched their businesses.

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About Jessica Livingston

Jessica Livingston is a founding partner at Y Combinator, a seed-stage venture firm based in Cambridge, MA, and Mountain View, CA. She was previously VP of marketing at investment bank Adams Harkness. In addition to her work with startups at Y Combinator, she organizes Startup School. She has a BA in English from Bucknell.

She’s the author of Founders at Work.

Raw transcript


Mixergy’s audio transcription is done by Speechpad

Andrew: This interview is sponsored by Grasshopper, the virtual phone system that entrepreneurs love because you can use your own phones and manage it on the Web. Check out Grasshopper.com. It’s also sponsored by Wufoo where you can go right now to get embeddable forms and surveys that you can add to your website for free. Go to Wufoo.com. And it’s sponsored by Shopify. When you go to Shopify.com, you can create a store within minutes and have all the support and features that you need to make that store grow. Check out Shopify.com. Here’s the program.

Hey, everyone, it’s Andrew Warner, founder of Mixergy.com, home of the ambitious upstart. Today, I’ve got with me – man, I’ve really been looking forward to this interview. I’ve got Jessica Livingston, she is a founding partner of Y Combinator, the seed funding firm that helped launch over 200 startups and the author of “Founders at Work,” a book of biographical interviews with 32 founders including the founders of PayPal, craigslists, Hotmail, and TiVo. Here’s my goal for this interview, Jessica and the audience.

Two things. First of all, when I interviewed your co-founder at Y Combinator, Paul Graham, he called you the “social radar.” He said that you know who to invest in, who’s the right fit, who’s got what it takes. I want to learn that from you. I want to find out how you know, and more importantly, how I and my audience can pick up on some of those tips, some of that ability to pick the people that we’re going to be working with. The second thing is, I’m fascinated by “Founders at Work,” a lot of people who care about entrepreneurship, especially in the Internet space, just keep talking about these stories in that book. I want to know how you got those stories. In fact, let’s start with that.

Here’s what I do when I do interviews, and I model a lot of my work here on your book. I hear people say, “Andrew, it’s just stories, they’re not useful. It’s just interesting” or fluffs, somebody called these kinds of interviews on Hacker News earlier today. What do you think the value is of reading or listening to stories of successful founders?

Interviewee: I can tell you, it’s anything but fluff. The reason I worked on “Founders at Work” was because I felt like the early stages of starting a company were totally mysterious. You don’t hear about companies or read about them in the news until they’re much further along. So, what happens when you’re first getting started, like weird things happen with startups, and it’s very mysterious for people. So I thought it was really important to share the stories of the early days with the world. So, if you’re thinking about starting a startup, it’s not quite as mysterious to you. The best way to do that is to sort of unleash the stories that are in the startup founders had in a story format. That’s the way they’re most interesting. You learn important trends based on these stories.

For example, how many startups got started by accident? I don’t think the world like really necessarily knows that. These big companies like Google now and all these successful companies, the founders didn’t say, “Oh, we’re going to do a startup.” Most of them just started working on something that interested them or tried to solve their own problem or just had a little side project going and it evolved. So I don’t think these stories are fluff at all, I think you learn like some really important lessons.

Andrew: Why leave it up to your audience to learn those lessons on their own instead of doing some of the work for them by maybe interviewing the same 32 founders that you interviewed for “Founders at Work,” and pulling out ten lessons from it and saying, “Guys, here are the ten things that you can go and apply tomorrow.”

Interviewee: I think it’s much more interesting to hear from the founders themselves. Who am I to distill this information? I certainly have, I certainly try to draw some conclusions and to try to find personality traits that cut across all these 32 people. I tried to pick out some themes, but who am I to share these stories? It’s so much more interesting when it’s being told by the founder who experienced it. You can sort of get in their mind a little bit better and you can really sense the emotion going on. Some of these stories, I was honestly on the edge of my seat listening to. For me to not include those, I think, it would just have a different feel.

Andrew: What kind of conclusions were you able to draw? What kind of themes stood out?

Interviewee: There were several. The first one I already touched on was that a lot of these successful founders don’t go out trying to start a startup. They’re often trying to fix something that’s broken in their own world…
minute 5 to minute 10

Interviewee: …they’re often trying to fix something that’s broken in their own world. A lot of them are programmers, so they’re curious by nature. They think, “Oh, what would happen if I did this?” Or, they’re trying to solve a problem that they had. Hotmail, for instance, they were working on another startup idea, there were colleagues at work, and they couldn’t communicate via email because of firewall at their company. So they thought, “Gosh, how do we solve this problem?” And they came up with the idea of Web-based email to solve their own problem. So, Paul just wrote about this in an essay the other day, the organic startup ideas, and we see that all the time at Y Combinator. People get started with something to address their own needs.

So that’s one theme. The other theme that I think that’s really important for people to remember was how often startup founders, that are hugely successful now, get rejected early on. [pause] will say, “This is a dumb idea. You shouldn’t be working on that. No investor will invest in them.” I mean, there are countless examples of people trying to raise funding and they just got turned down by investors because they thought it was a bad idea or didn’t think the person was formidable enough. That’s important because it’s hard to start a startup. If you’re a first time founder, you’re going to get rejected a lot in a lot of different ways, and it’s really hard. So I think if you can see that gosh, these successful people were initially rejected, it makes you feel a little bit better.

Another theme that’s really important is openmindedness you have to have and flexibility to change your idea and to listen to users. A lot of the startups in the book, and I see this again in Y Combinator startups, they start out saying, “We’re going to do this.” They try to do it and it doesn’t really stick, and so they think, “Oh, gosh. The users are actually more interested in this aspect of our site,” and they work on that. So there’s a lot of trial and error, and it gets glamorized, I think, in the press with these successful startups. They say, “Oh, he had this brilliant idea. We knew this was going to be big and it was great.” That’s not the way it usually is. It’s usually a lot of testing one thing out, if not working, and then happening up on the right thing.

Andrew: I’ve noticed that there’s the PR story that actually very often, is manufactured by a PR person, and then there’s the real story. I’m wondering how can you get past that PR story? I should say this, too, that sometimes, we kind of make it up ourselves. We look back at our history and we overlook the things that don’t fit our perception of the world and we highlight the things that do stand up for what we believe in the world. How do you, as an interviewer, get underneath and find out what the real story is?

Interviewee: I interviewed the founder and not the PR person of the company. Definitely going straight to the founders is important because they were the only ones who were there. I did interview the first employee with Yahoo, but for the most part, every other person I interviewed for the book was a founder, because things can get changed. If you’re talking to someone who is a later employee, maybe they’d heard stories about what it was like when they first got started, but only the founder knows what it was like when they just got started. So that’s important.

I don’t know, I don’t know how I’ll see and try to get the real scoop. It was interesting, when I asked Steve Wozniak about the garage, the famous garage that Apple got started in, and he was like, “Oh, we didn’t really work in the garage. Yes, we did some QA testing out there, but no, we didn’t really start in the garage.” You just sort of wonder how these things get passed on. I don’t know.

Andrew: You mentioned Hotmail earlier. There was a note on your blog that said that, basically, two pieces of information in your story about Hotmail were false. How did you insure that the information that you got from entrepreneurs was real? I have that issue here with my interviews. I can’t fact check everything before putting it out there. I have to just open myself up, but I’m wondering how you did it.

Interviewee: One of the things that I did was I told every person that I interviewed, before I interviewed them, that they’d have the ability to review the interview and make any edits that they wanted to or deletions or whatever, and they’d have the final approval.
Interviewee: And I did that and I got final approval from everyone in the book. And so that’s the best you can do. I don’t know how else. You have to trust that the founder’s going to tell you the truth.

Andrew: What about this? I did an interview recently with the founder of an online casino company and he did this back in the mid to late 90s, back when he says it was a grey area, online gambling, and back when it was still possible for a kid in his 20s to build a casino online. It’s not true anymore. Today we know that black and white online casinos in the U.S. are not allowed. The ability to create a casino in your 20s isn’t available to anyone. And there’s some feedback you get from people who say, ‘Well this doesn’t apply anymore. Bring me people who started a company last year or two years ago to learn from them.’ What’s the value of learning from entrepreneurs who seize the opportunities that no longer exists?

Interviewee: Well I interviewed a lot of people from all different eras and I think there’s always useful information. Even if the world doesn’t look like that right now, I think there’s some sort of trends and definitely personality traits that will always apply. Like was this person doing the casino, what was unique about what he did? How did he recognize that there was an opportunity there? That’s a big thing. It doesn’t really have to be like, what is the world like right now?

I mean, you can learn a lot about going back to, I’ll give the Steve Wozniak example again and that was in the 70s. There’s some interesting examples from that time. He built that computer because he wanted a computer himself. And they originally thought that they’d have this build-at-home, build-a-computer kit and you can do that, And wow, they learned something interesting from the users. No one knew how to sauter [sp] themselves so they had to do it. So you see some interesting themes like listening to your users and making something that you yourself have a need for.

And so I don’t think it really matters if it’s like, what’s happening right now. And in fact, sometimes it’s hard to get good interviews about what’s happening right now because the people that you’re talking to are still deeply involved with their startup. And I found that people tend not to share quite as much when they’re still deeply involved in their startup. In fact, the more time you can have between the end of the startup or the person’s liquidity event or something and the interview, the better. Because they’re more willing to be open about the embarrassing and funny stories.

Andrew: Yeah, I’ve noticed that too. The more time I could have separated from the subject that I’m interviewing about and the interview itself, the more truthful and the more open that the person can be.

Interviewee: Yes.

Andrew: What about the way that you did it? How much time did you spend with each entrepreneur, with each founder to do the interview?

Interviewee: Well, a lot of these people are super busy, super successful people so I tend to do…I usually have about an hour and a half with each of the people that I interviewed. Some of the super busy ones, it was only an hour. An hour was pushing it because I’d find that I’d always start the interviews trying to warm the people up by saying, ‘Take me back to when you first got started. Tell me what was happening at that time and how did you first got started.” And someone can go on for half an hour giving you the backdrop. And then you’re just getting into the really interesting stuff and that hour’s up. So I usually try to get an hour and a half with the people.

And then I went back and transcribed everything myself and then edited all the interviews myself. That was the most time consuming part, actually. That and doing sort of the preparation, trying to learn about the company and what questions would I find interesting. But I’d go back and edit all of them. I wouldn’t put new things in but I would definitely delete duplicate thoughts and certainly take out the ums and the so’s and all that and just try to make it so it was in an easy to read format. That actually was the most laborious part of the whole thing. Then I’d send back them back the interviews for them to review so it wasn’t super time consuming on their part.

Andrew: OK, so say somebody was listening to us right now, it’s going to be at a cocktail party with someone who has time to teach them. A successful entrepreneur has time to talk about his past…
minute 15 to minute 20

Andrew: If, say, somebody who is listening to us right now is going to be at the cocktail party with someone who has time to teach him. A successful entrepreneur has time to talk about his past and to teach him based on the past, not an hour, not an hour and a half, maybe not even half an hour. What questions can they ask to extract the most value out of that kind of conversation?

Interviewee: I would probably ask them what mistakes did they make, because you can learn a lot from people’s mistakes. What did they get wrong? I might ask them, “What did you wish you had known when you were just starting a company?” They’ll tell you, “Oh, man! I had no idea about this. No one told me how hard the emotional rollercoasters would be.” I’d also ask them what surprised them most about a startup, because that’s a very good question to ask people. What’s the most surprising about X? These are things that even man(?) themselves might not have thought about. You can’t really read too much. If you want to learn about incorporating or you want to learn about something that you can easily find online, don’t waste your time on that. Ask them like, “What did you get wrong that I shouldn’t?”

Andrew: Interesting that you bring that up. I interviewed Jason Fried, co-founder of 37signals and I asked him what he got wrong, and he said he doesn’t think of that. He says, “There’s so many things that could go wrong, so many mistakes that you can make. Even if you study five different mistakes a day, you still will only touch on a small percentage of the overall mistakes that you can make. So why bother learning that instead of focusing on just the successes?” But I share your point of view, that there’s a lot to learn from mistakes. What do you think there is to learn?

Interviewee: From mistakes? There’s a whole general class of mistakes that I know that first time founders all say will get wrong. For example, they spend a lot of time worrying about their equity distribution. There are two founders and they spend all these time, “Should we divide it up equally?” Or, “I’ve spent a little more time or should I get more stock?” and they agonize over this. That’s a mistake, it’s a waste of time. Talk about it, be comfortable with how much stock you’re getting. In most cases, I would suggest dividing up the stock equally. If you’re the next Google, optimizing that initial share distribution is not going to make a big difference at the end of the day. That’s an easily avoided problem that I see, and there’s a whole class of this problems.

I can’t solve someone’s problem in terms of what they’re going to do for their startup idea. But something that I see patterns, it’s easy for me to say, “Don’t make this mistake. Don’t agonize over this. Don’t worry about competitors.” I’ll see someone saying, “Oh, my God. Oh, my God. Google just released this, what are we going to do? We’re dead!” Sometimes, you shouldn’t spend too much time worrying about a competitor. You should focus on your own startup. How are you going to beat them in terms of teachers(?). Again, a lot of times, we’ll see people worrying about things that they shouldn’t.

So, don’t make those mistakes. Don’t worry about those things that aren’t important. Or, “Oh, I have to bring on all these advisers right now. I have to build my adviser team.” You don’t need to build your adviser team when you’re a month old, work on the product. That’s all you need to care about, it’s making something people want.

Andrew: I do see a lot of commonalities in the interviews that I’ve done here with entrepreneurs who’ve had failed businesses. If we were to say that there’s an 80/20 rule, what’s the 20% of mistakes. How many mistakes do you think account for 80% of the failure?

Interviewee: I’m sort of an expert in early stage failure; early, early stage failure. I definitely see some themes, like a lot of the failure is due to not making something that people want. Again, our motto is to make something that people want. If you create something and no one uses it, you’re dead. Nothing else you do is going to matter if people don’t like your product. I see destruction causing death for a lot of company, and that could be destruction of squabbles between co-founders or working on building out that advisory board before you get a product. That’s definitely a big mistake, letting yourself get distracted and a lot of people can get distracted in fund raising and doing all these other things and not working on their product.
Interviewee: And not working on their product. It is hard cause there are co-founders not getting along, and I do not know if I’d call that a mistake. I

guess you can classify it as “you chose the wrong co-founder”, but that is a major cause of early start-up death. It is like co-founders disagreeing and then they break up. Oh, it is awful! A lot of mistakes are fixable. A lot of mistakes, the real bad outcome is that they are mere distractions for you, which again is the biggest cause of death for start-ups. We see a lot of people making mistakes and most you can bounce back from but my point is if you can learn what mistakes to avoid and have other founders say do not spend your time doing this. Then why not learn from those?

Andrew: What mistakes have you made at Y Combinator?

Interviewee: What mistakes have we made? I hate being on this side of the table… Well, one that comes to mind in my world, and I used to, not so much

anymore because we have a lawyer on retainer who works with the local start-ups. I used to be very involved in helping the start-ups incorporate and do all their paperwork, to setup their company properly – equity distribution and employee agreements and stuff like that. And one of these mistakes was that, early on, we had all these templates, and we had them created in a very standard format, and we didn’t want to impose too many rules and restrictions on people, and so I said, in terms of vesting, I said, it’s totally up to you, we recommended vesting, but its up to the founders if they want to have vesting. And so, a lot of founders said, we don’t want vesting; why should we have vesting if we don’t need to? And I saw that led to a lot of bad things, not having vesting. I won’t waste time talking about it, but a lot of bad things happened when there’s no vesting. And so now, years later, and actually it didn’t take me too long to figure that out, but now I basically say, you absolutely have to have vesting, Y Combinator never tells you what you have to do, but I strongly recommend it, and if you don’t want to have vesting, come talk to me because I’m going to convince you otherwise. So that was a big mistake, because we still have some founders who have some major problems because of that.

Andrew: By vesting, we mean that instead of giving the founders the share of the ownership of the company all at once, you say, in time, you’re going to get

your full ownership of this business, and the reason you want to do it is because if you give one of the founders all of his shares right up front, he doesn’t have an incentive to stick around, he can just go on and do the next project. Is that true?

Interviewee: That’s absolutely true. In a nutshell, you have the standard vesting, is sort of your – all of your shares vest yearly over a period of four

years, and what happens if you don’t have vesting is exactly what you said. All of a sudden, someone outright owns a large equity stake in the company, and

after two months, says “I’m not really into this anymore, I’m going to go work for a big company, or I’m going to go back to school”, and you have a huge

equity holder in your company who’s not doing anything to contribute on a daily basis, and that causes lots of problems in terms of founder’s morale, the

person stayed behind working but also investors don’t like to see that, so causes a lot of problems.

Andrew: Okay, and we just anticipated Danno in the audience’s questions, so I’m glad we were able to answer that question for you Danno. Okay, so take me back

to just before you guys co-founded Y Combinator. What was that original vision?

Interviewee: Original vision? I didn’t know there was a vision! When we first started, it was all an experiment, what happened was, Paul, Robert and Trevor

definitely wanted to give back to the start-up community and do some angel investing, because they had been helped out, years before with Feo Lab, but

someone who invested $10,000 in their company and helped them incorporate cause he was a lawyer. And so, they wanted to do angel investing, but they didn’t

want, but Paul didn’t want to have to read business plans every day and he didn’t want to deal with all the things that go along with being an angel investor. And I was leaving my job – I worked at an investment bank – and I was leaving my job to work on the book full-time, cause I had just gotten the book deal.
minute 25 to minute 30

Interviewee: …So I said, “Well, I’m really interested in this sort of thing. I can help with all the business side and the organizational stuff and you, guys, can help work on the idea and strategize with the startups.” So we just sort of said, “Okay, let’s just form something that we can invest in startups.” It was in March, I think, when we said, “Well, we don’t know anything about angel investing. Let’s try to get a whole group together this summer, and if we invest in many startups at once, we’ll learn a lot.”

I remember Paul wrote the Y Combinator website in like a day. We put up this application form and kind of crossed our fingers that people would apply. And, oh, my gosh, we got applications. The deal was they’d have to move to Cambridge in the summer and we sort of based our investment amount on an MIT grad student stipend. So I forgot what the amount was back then, but it’s a small amount of money. They moved to Cambridge and we’d worked with them over the 3-month period and we actually got people to applied and came to interview.

There really wasn’t a vision back then other than we wanted to help people start startups. I mean, there was sort of the whole Paul’s philosophy, he had written that essay, he had written how to start a startup. So it’s definitely on his mind thinking about these things. But he had written, “Hiring is Obsolete,” and we thought, “You know, it’s really interesting. It’s a lot cheaper to start a startup now, even compared to during the bubble time, it’s a lot cheaper. You just need your computer and pay some server fees and that’s it.” So he wrote this essay “Hiring is Obsolete,” which was, you know, start your own startup, don’t climb the corporate ladder. Start your own startup and get Microsoft to buy you in order to get you to work for them. We sort of thought this could be an interesting trend about younger people starting their own companies out of college instead of going to work as a junior junior programmer at some big company.

So, we did this at summer. We got eight groups that came, and it worked. We called everyone we knew in town to be guest speakers, people who were experts in the startup world. We had guest speakers every week and we had a demo day. So lot of the early stuff worked out really well and we’re still doing it today, of course, on a much larger scale. But a lot of those initial ideas worked. But I can’t say we had a big vision, I really can’t.

Andrew: Here’s what I’m wondering. By the way, the decision to do it in batches, that’s why even your competitors say, that’s the biggest innovation that you, guys, brought in. That, and I guess the small amounts that you invest in a company. But what you’re saying is that you didn’t know enough about investing, and so you decided to invest in many companies at once. Why? How do you go from not knowing to say, “We’re going to do multiple startups”?

Interviewee: I think we just thought that’s how we’d learned. If we had eight groups, you learn a hell lot more dealing with eight different companies that just one. Let me tell you, every startup is different, even though they’re patterned, everyone is different. The personalities of the founders, the ideas, things that happened to them, like the outside circumstances, everything is different. So, we said, “Let’s just learn by helping a whole group.” You know, it was an experiment. What we found from that experiment was that investing in batches turned out to be amazing. One of the reasons is because it’s overwhelming(?) doing a startup. If you’re just one or two people working on at your apartment, it’s very isolating. You’re always working in a state of uncertainty, and so it can be depressing.

So, we found that this eight groups just bonded, they could lean on each other for support. “Oh, you’re facing this problem, so am I,” and they helped each other. Now, of course, the Y Combinator community has grown to, I think, around 500 founders, and everyone helps each other. If you have a technical problem, there is someone in this community who can help you. It happens over and over where through the older alumni who’ve been through it before help the new people with problems that they themselves faced. They feel this need to give back to the Y Combinator community. So, it’s really amazing that it worked out so well.

Andrew: I’ve seen it even as an outsider, “Man, they’re the most incredibly helpful people I’ve ever met.” I keep saying it to them both in the interviews and in emails afterwards. I feel like I owe you so much, I don’t even know how I could pay you back…
Andrew: I mean, I don’t know that I could bring up specific examples, but they’ve just been really generous with their time, with dealing with technical issues during an interview like this, and helping me get other interviewees. How did you get that original eight?

Interviewee: They were. I’m telling you, we put up the application, and hoped people would apply. I forget how many groups we interviewed, but we accepted eight. I think they were fans of Paul Brown’s essays,you know, that was sort of our initial marketing thing that we did. So they were fans of his. We had met one the groups, I think the Retec guys we had met at Paul’s How To Start A Start Up talk at Harvard. So we had met them and loved them. And God, these amazing people.. like Sam Altman of Looped was in that batch, and the Justin Tv guys were in that batch. They were doing a different idea at the idea. Jolie Yun of Tex Pay Me, the Retec guys. It mean, it was this great group of people. We were lucky. We were lucky.

Andrew: Okay, now we get into the social radar part. I think it was Alexis O’Hanyan who said you guys didn’t like his idea. He had an idea for using a mobile phone to order food or something kind of convoluted. And he spent years on it it seemed like, really had a lot invested in it. You guys helped him change his focus and got him to, helped him come up with the Retet idea. So, it wasn’t that you loved his business, it wasn’t that you loved his website. There was something about him. How do you know? How did you know he had it?

Interviewee: Well, it was both of them. It was Steven Huffman and Alexis.

Andrew: Right. I say Alexis a lot, not to take credit away from his co-founder, but because Alexis was here doing an interview on Mixer G, but you’re right. How did you know that they both had it?

Interviewee: Well, I’ll tell you. One thing that I thought was amazing about them, and this was back when I didn’t have nearly as much practice at judging start up founders, this was all brand new, but I saw some interesting characteristics in them. The first was that they came up to Cambridge from UVA, like on the train to hear Paul’s talk, like they cared enough about what he had to say and were interested enough in start ups to like, to travel all that way from college. So I was kind of impressed with that. And then, I just sensed their genuine, like their interaction was really good, you could tell they were good friends, that they got along, and that they could really trust each other. I could just sense that. Even. Back in the original interview days, we did like thirty minute interviews. None of these ten minute things. So we had more time to sort of witness the dynamics. And they just seemed so earnest, and like thoughtful, and sort of almost wise beyond their years and mature. And I just loved them. I loved them both immediately, but we thought oh my gosh, these like twenty-two year old guys, they can’t do this idea with like, where they have to cut deals with fast food companies like McDonald’s. This isn’t going to work. So we turned them down.

And I then I was, I was like in pain all night. I remember thinking like I love those guys, I really want to give them a chance. And Paul did too and. So I actually I don’t think I quit my job yet. I was wrapping things up at my job, so I went to work. And Paul emailed me and basically said The Retet, we didn’t call them The Retet, we called them The Muffins actually.

Andrew: Why?

Interviewee: It was just sort of a term of affection. I just loved them so much, and I just called. It was a dumb term, but I called them The Muffins. We have nicknames, had nicknames for everyone. And Paul sent me this email saying The Muffins have been saved. And I was like “Yes!”. And what happened was, that morning Paul called them and was like we really liked you guys, let’s try to think of a different idea. And they got off of the train in like New Haven, and came back to Boston, and like brainstormed with him, and they cooked up this idea for Retet, and the rest is history. Like, those guys are, those guys are amazing.

Andrew: You mentioned that now you give a new applicant ten minutes. When I interviewed Paul Graham, one of the big questions that people said I should have asked him was how can you pick within ten minutes, how can you decide if someone’s a good fit. It does seem like a short amount of time to decide whether you’re going to invest not just money but time and trust in someone. How do you do it in ten minutes?

Interviewee: It is, it is hard, but I think if you talk to a lot of investors, in hindsight, they’ll say I kind of had a feeling after the first five minutes. Like you really don’t need an hour to spend with someone, you know. And I guess it’s different if you’re a VC and you’re investing five million dollars, you want to spend more than five minutes with the, ten minutes with those people.
Interviewee: But, it’s hard to judge, but like you can have a lot of conversations around that idea in that amount, and judge like how are these people thinking about their idea. What have they built? Can they demonstrate that they’re able to build something good. So my three partners are kind of assessing their technical skill, and what I’m doing, I’m embarrassed to recall the social radar, because I don’t know if it’s true, but I’m sort of looking you know, at how, you know, how is the interaction between the two founders. Do they seem to get along or is one sort of steamrolling the whole conversation while the other one doesn’t talk at all. Do these people seem earnest? I know it’s a quick amount of time, but I try tell like are they sort of nice, earnest people who are going to work hard and care. Or are they phony? You know, it’s hard, it’s very hard to tell. And like, sometimes we get tricked, but I think, I think you can tell a lot about a person in ten minutes. You really can. And of course, we have the, now we have the videos where we can, on the applications, we can sort of see people, but it’s not interactive, of course. But you can sort of tell, and you can tell like what someone’s attitude is like in a short amount of time. I don’t know, it’s hard to put into words.

Andrew: So most people aren’t going to be sitting on your side of table looking at founders in this kind of ten minute structure, but they are going to be looking at co-founders, people to trust with departments in their business, people to hire in key positions. What can they do to find that right match, now that you’ve seen so many different co-founders who work well together or work poorly together. What can they look for?

Interviewee: Well, assuming that you’ve never met the person before. I mean, the best kind of person to hire is somebody you’ve already have worked with or know very well, but assuming you don’t know them, I definitely would suggest having a trial work period together. Maybe it’s like you work together for two weeks, and then you decide if this person is right, because I definitely wouldn’t recommend a ten minute interview when you’re hiring someone. And hiring by the way, just as an aside, seems to be like the biggest problem lately that our, the Y Commonator Founders are facing, it’s really tough to find good people. So I’d recommend, you know, the trial, working with them on a trial basis. See what they’ve built before, I mean, have they, are they capable of getting something done. That’s important. Have your best technical people assess, like if you’re not a technical person, find someone who is technical to be able to assess if this person technically is good. Like I can’t judge if someone technically is good, but I have three partners who can. And just like do you get along with them, do they seem reasonable. I know that sounds crazy, but you want to be sure that you work with someone who is level-headed and not obstreperous. Even though a lot of programmers can kind of be ornery, you want to work with someone who has that open-mindedness and flexibility to do different things and you want to kind of judge, look for that I think.

Andrew: How have you been tricked? How does somebody trick you?

Interviewee: (Laughs) Oh gosh. I’m sure I’ve been tricked a lot. (Sighs) I think what happens with me is if I’m, I’m looking for like determination, I’m looking for someone who’s going to hang tough, when the going gets tough. Because, I don’t know if you’ve ever, if Paul has ever talked about this “Trough of Sorrow”, but there’s this idea that when you launch, you get this initial spike. You get a lot of publicity, and then it drops precipitously. And then, this “Trough of Sorrow” which looks like a flat line there. And every start up hits the “Trough of Sorrow”. I mean, some are lucky and they don’t, but most of them do. And that’s when, you know, you can’t grow your user base, and you can’t find investment, no-one wants, you’re getting rejected all the time, okay. So, how do pick trick me, or us I should say. They seem super determined, and they seem like we’re going to stick with this no matter what. And if this idea doesn’t work, we’re going to try something else. And then we find that like they’re not really that interested in sticking around. And they sort of thought, they had thought oh gosh,we are going to join Y Combinator, and everything’s going to be easy, and we’re going to build the thing, and everyone’s going to love it, we’re going to make an investment, and it’s not going to be hard. And it is hard. I think I get tricked by people who seem super determined, but don’t hang in there.
Interviewee: …But, don’t hang in there.

Andrew: Okay, let’s go back then to the second group. You had that first eight run, it worked out well. What were you going to do differently, what, what did you say didn’t exactly work out that we want to improve it next time.

Interviewee: Well, one thing that we did differently to improve was we moved out to Silicon Valley. I remember that, that was a big turning point in Y Combinator actually. Cause, I didn’t want to go initially. I was like, ah, how can you –Paul was like we should go out to Silicon Valley because if we are going to be involved in start-ups, that’s where all, a lot of the action is. And I thought, oh my gosh, we just got everything set up in Boston. We don’t have a place –this is in like October. You know, we don’t have a place to work. We, what are we going to do. I don’t have, like, slow cookers, you know, crock-pots, and like silverware for twenty-five people. All these different things that I thought would be a huge pain in the butt. But we worked it out and Trevor, our other partner, who has space with anti-bots, like, loaned us the space. We moved out there. Got everything set up. And it was the best thing we ever did because we really go connected with a lot of key people out here, investors, guest speakers. I mean, if you are going to do a start up its very important to have some connection with Silicon Valley. So that was something that, that we improved. I can’t, I am trying to remember what we thought we needed to change. There wasn’t, there wasn’t anything dramatically wrong. I don’t think there was anything that we said we’ve got to do, you know we’ve go to do this differently. I think we just said we’ve got to get more investor connections so at demo day there are more than twenty people in the audience. You know, get more people to write checks as follow-on funding. Get more connected with guests, people who could serve as guest speakers and who could serve as advisors to our start ups. Because we do, we spend a lot of time connecting our start-ups with people that can help them, and a lot of people that can help them are out here. So, that, that was one thing we improved upon.

Andrew: Guest speakers seems to be important. How do you make those speakers really helpful to the audience because we’ve all gone to events. You watch, we watch speaker, the speaker was interesting but you know, you still have to go back to work the next day. What he talked about the night before doesn’t necessarily translate into, into practical, useful information that you can use the next day, how do you make them useful?

Interviewee: Well, a couple, a couple things. The first is all of our talks are off the record. And that’s, that doesn’t happen too frequently. I mean, now, everyone wants to live-stream everything, and blog, and tweet and we say no, everything is off the record and that genuinely makes people share things that they wouldn’t share otherwise. And I’ll tell you I’ve learned more things at Y Combinator dinners from these famous successful entrepreneurs that I can’t even share, really but that are mind-blowing because they, they, totally open up. It’s amazing how much they open up. So that’s super useful to learn these sort of secrets that would otherwise not been told. And the other thing, is a lot of these people, it doesn’t just end with here’s my talk, goodbye. A lot of these people maintain relationships with the founders, like the founders get to pitch to them during the dinner and like they’ll carry on conversations. Maybe, that entrepreneur is also an investor and maybe, you know, we’ve had definitely have had some of the guest speakers invest in the companies or connect them with useful people. Or bring them in to get acquired, I mean, that’s definitely happened where someone has been the champion within the firm, so a lot of interesting relationships develop as a result of these dinners.

Andrew: I see that there a couple of people in the audience who asked this question. Do you guys only invest in companies that have a technical co-founder?

Interviewee: Yes. Although, I believe, actually, a, Harge, Harge and Coal of Optimatic and Harg now works with Y Combinator. They were not technical. They were the only people we’ve ever funded who, who were not technical. But, but, they were teaching themselves to program! I heard that, and I was like “Your business guy is teaching yourself to program. I don’t care what your idea is, you’re in,” like I loved them. So, yes, every single group, I believe, that we’ve ever funded has had at least one technical person on the team.

Interviewee: I see, that’s what I thought. Alright, advisors…
Andrew: All right. Advisors. How can a startup make the most out of a relationship with an advisor?

Interviewee: Hmm. Well, I mean it’s hard because people who are advisors are probably very successful, busy people themselves. So you want to use their time efficiently. You know, how do they make the most… I think being well-prepared when you go to talk to the advisor. And say, “Here’s what I’ve done. I’d love your opinion on this specific thing. How can this be improved? What am I doing wrong? And really not go in with sort of vague ideas, like definitely use the advisor’s time efficiently. And ask them like, “Can you help us do this? Can you help us hire people? Here’s what we need.” And people, at least in Silicon Valley, like love to help people out. They want to give back. And they want to help do what they can to help a startup succeed. So I think like using their time efficiently, and knowing what their area of expertise is, and like, I hate using this word, but like leveraging that, with a particular advisor. I think that’s sort of the best way.

Andrew: Before we started the interview, I asked you how many startups did you guys fund or help launch. And I was thinking the number was 172. And you said, “It’s actually over 200 because we just accepted a new group of startups in the program.” Ordinarily, just accepting wouldn’t mean that you helped launched them. But I said, “Yeah, let’s include them because what I know about the way that you work is, when you accept a startup, you already start helping them out. You already start thinking through their idea, the way you did with WuFoo. They already start picking your brain, and spending tons of time with you, the way the guys behind Air B&B said they kept doing with Paul Graham. My question is, how do you do it? How do you help these dozens, and now hundreds of startups, think through their ideas, and decide what company they’re going to go and build? How can you do… How can you help somebody come up with valuable ideas within minutes, within the first time that you meet them?

Interviewee: Paul Graham. [Laughs] No, that is really his department. He works very closely with the startups on their idea, and on their vision, on their strategy, what can they launch with, well, what is the grand vision. That’s his area of expertise, and he’s really good at doing that. And these new founders that we just accepted, the first dinner’s not till June, but we’re working with them now. I’m working with them along with our lawyer to help them get incorporated, to get that out of the way. Paul has office hours so they can sign up and meet with him and brainstorm. But it’s really, Paul’s got the energy and that’s his area of…

Andrew: He’s the product guy, and when I interviewed him, and I asked him how he can do it, how he can help entrepreneurs think through their product, he said, he really doesn’t know. And he has this fear that that gift is going to go away. Now, you as an outsider, you’re laughing before I ask this question, why?

Interviewee: I’m laughing because I don’t think it’s going to go away.

Andrew: I don’t think so, either. But I can see how when it’s so innate, it’s hard for him to figure out exactly what he’s doing. But you’re watching on the outside, you’ve got a talent for spotting patterns. What kind of patterns are you noticing in the way that he helps entrepreneurs create their products?

Interviewee: Well, patterns? I mean, he definitely helps them sort out, they might have this vague idea, he helps them, directs them in a way that’s going to be best for that company. And direct them in a way that’s going to be best for those particular founders. I mean, if they’re not super duper salespeople, maybe there’s a way that they can build this to get users without having that sales person. That’s sort of a bad example, but he’s really good at sort of being a chiropractor for ideas. And helping people brainstorm like new ideas that they might not have thought of, different directions. Helping people sort of wade through the many ideas that they have and boil it down to like, this is what you should launch it with. Focus on this, focus on getting users for this, bearing in mind that your vision is going to be over this way, but you got to start here first. And he’s just really good at that. And I was laughing when you said that he said he was worried this gift would go away, because I’ve known him for a long time now…
Interviewee: Because I haven’t, you know, I’ve known him for a long time now and I just haven’t seen… He always has new ideas and he’s always trying to help people improve things and do new things.

Andrew: You said that he was a chiropractor for new ideas. I wrote that down to ask you what does that mean?

Interviewee: Well that means like you know i have this, i have this bad back and you know he can come and say “er er er” lets move it a little this way just a little bit in this direction and all of a sudden you go “oh its so much better” and so you know chiropractor for ideas like someone will come to him with like sort of a good idea that for some reason isn’t taking off or is going in the wrong direction and he’ll just make, like, you know a suggestion for a little tweak and all of a sudden, whoa, it’s like, a great idea you know and he’s good at that.

Andrew: You said he helps them come up with the new ideas. He helps them brain storm. I remember when I talked to Alexis he said as they began brainstorming the idea that became Reddit they were inspired by delicious’, i forget what it was called, the most bookmarked for within the last day or websites they said “Well it would be nice if there were a way to find to find relevant sites or to find an interesting post.” It seems like one way to find a new idea is to see what already exists and you’d want more of. What other ways are there that, You’ve seen Paul Gram or you guys at Y Combinator or the companies that you’ve, you’ve helped launch. What are some ways that they’ve come up with new ideas?

Interviewee: Well I mean definitely what’s broken what. What is really broken out there and also sort of you know like air b and b is an example of you know a company that’s taking advantage of like, the hotel business being a little bit broken you know and like their letting people rent out space now. Unthinkable 10 years ago. It just seemed so crazy and so if you think about something that, sort of, now with the internet you know consumers can participate more, its not controlled, like newspapers with Reddit. Newspapers were controlled by the editors and that sort of thing and then, like, now that you democratize all these things on the internet there’s all these new opportunities and like that’s sort of a hotbed for ideas i think.

Andrew: How much time do you spend thinking about these questions, looking for patterns of, I asked you earlier about the number of ways that entrepreneurs can fail I’m asking you about where new ideas come from, do you spend time just sitting around saying where do all these ideas, the ones that have worked for us, where do they come from how do we figure out a pattern here that we can then apply in the future or do you feel it. What’s, how much of it is thought out that way.

Interviewee: Do you mean with like regard to start ups like with their, I’m not sure…

Andrew: To everything, do you sit down and, how methodical are you, how methodical are you at saying you know, i really, there’s something about my social radar here that’s worked, I’ve discovered these 20 guys that worked and these 5 that tricked me, what patterns do i see in the five and what patterns do i see in the other 20.

Interviewee: Well we definitely have a lot of data that we do try to keep organized and we’re getting better at keeping organized, Paul writes a lot of software. We’ve been you know just things we’ll think like well, you know, what was it about this group that was so good that you know that we recognized in the interview. Let’s find more people like this you know and we definitely do spend a lot of time sort of trying to be methodical but a lot of it’s just like start ups you know. You can’t plan everything out. So you can only be methodical up to a point but we’re always like trying to improve things, we’re always trying experiments to see if we can make…

Andrew: Can you give me an example?

Interviewee: Experiments…well you know one experiment that we’ve, that was new to this last batch was, we’d always had done this informally, we used to have Paul Bucheit who, if you haven’t interviewed him yet, have you interviewed him yet?

Andrew: Not formally, just at a conference, we flipped the camera on.

Interviewee: Get on him, get on him to do an interview he’s awesome. He was the founder of Friendfeed, now acquired by Facebook and he was the creator of gmail. He’s in my book too. So Paul is an angel investor and we used to have him come in and spend an afternoon listening to the pitches of all the start ups and he’d say like, why he would invest or not invest and he’s really straight forward and it was great. It was great feed back for these start ups. This was prior to demo day and so we’d do this all the time and we’d definitely introduce people to investors informally.
Minute 55 to hour 1

Interviewee: …in the past, but this year, we thought, ‘let’s-, you know, we really want to get people prepared for Demo Day, and we wanna, like, put these founders through the-, through the investor ringer before they present to the investors so they’re not shocked when someone says ‘oh I don’t like that idea.’’ So we had, like, a little Angel Day a month before Demo Day and the founders had like ninety seconds to give their elevator pitch and then we matched them up with, you know, a few angels, you know, eminent-, eminent angel investors in Silicon Valley, and they met with them every week up until Demo Day. And the point was to give their pitch. You know, Paul was in the background working on the strategy and the product, and then they’d go test it out with a real live investor who sees tons of pitches and each week, you know, they’d give the pitch and say ‘would you invest or not?’ And a lot of times the investor, of course, would say ‘no I wouldn’t. And here’s why: I’m skeptical about this. Or, I think you need to go in this direction.’ And we found that that was real useful for people leading up to Demo Day. I think their-, their pitches at Demo Day were a lot more refined, and even they were more confident about their pitches ‘cause they had sort of been through this ahead of time. So that’s just one example-…

Andrew: Give-

Interviewee: …where we didn’t know if it was going to be good or not, but I think it was.

Andrew: Give an example of an experiment that failed.

Interviewee: An experiment that failed…? [clears throat] I can’t think of one off the top of my head, I really can’t. I’m sorry, I have to roll my eyes. I’ll-, I’ll think about it. I can’t-, I can’t come-, think of one off the top of my head. I’m sure there are plenty. I know, but again, we don’t put a whole lot of time into some of the things, so I’m sure there are plenty of examples where we tried something and it wasn’t super successful, so we just moved on. You know, it’s sort of like interning [SP] with software, you try something, it doesn’t work, do something else.

Andrew: I know that you’re-, that you haven’t been feeling well this week, and if you wanna take a-, a moment away from the camera, that’s fine, we can come back. I don’t-, I just have a few more questions to ask though.

Interviewee: No, that’s okay.

Andrew: Keep going?

Interviewee: I just apologize for having to blow my nose on camera. [laughs]

Andrew: I do it too. And I don’t do it ‘cause I’m sick, I just do it ‘cause I’m a big nerd who’s always had a runny nose. So if I do it all the time here, you might as well. Let’s see… Michael Jung- before the interview I took questions from people for you- Michael Jung asked, ‘what’s your biggest lesson from interviewing and working with so many entrepreneurs? Is there one biggest lesson that you’ve taken away?’

Interviewee: There’s so many different ones it’s hard to think of just one. Except that startups are hard, and startups are very fragile. And it can go either way at so many points, like, success and failure are not that far apart at so many points throughout the life cycle of a startup. And, like, the lesson is: you’ve got to be determined, you’ve got to be tough to get through all these challenges and these, like, overwhelming emotional rollercoasters: the rejection, the changing of the ideas, the, like, imminent failure every day it seems like. If you are not determined, like, you’re not-, you’re not gonna make it. And that-, that to me is sort of the most important thing that I took away from all these… it was… oh, one other thing is that a lot of these people who are famous now were not famous when they first got started. And that is, like, so inspirational to me because anyone can start a startup if they really want to. The barrier to entry is not that high. I mean you have to build something that people want, that’s a pretty high barrier, but, like, anyone can do it. And, like, all these people started out getting rejected and not feeling confident, you can do it too.

Andrew: Moses asks, ‘do you have any advice for entrepreneurs who are not part of the program?’ … Not part of Wycom Adiner [SP]

Interviewee: Well, I mean, a lot-, a lot of the advice that I… a lot of our advice, like, Paul writes about this, and that’s, like, easily accessible. Advice for people who are not part of Wycom Adiner? Find-, you know, always pick a good cofounder, make sure you have that, but once you have your team, try to meet other people working on startups. And even if it’s a matter of, like, getting together with them once a week so that you feel like you’re not alone, I think that’s sort of a big part, in-, again, in the early days of starting a startup, is to find other people who can understand. ‘Cause a lot of people, you start a startup and people are skeptical, people won’t understand, ‘why aren’t you working at a big company? That’s so weird.’ And you feel kind of like an alien. And so if you can find other people to…
Interviewee: ..and so if you can find other people to understand what you are doing. I think that would help, finding community.

Andrew: Can entrepreneurs duplicate some of what’s going on at Y Combinator. For example, take what you just said now, meet once a week to show each other what they’re working on, and talk about the progress they’ve made. Maybe invite a different angel investor in each week to be pitched for a minute and get feedback. Maybe bring in a speaker. It seems like all of these can be duplicated, they won’t be exactly a hundred-percent. Seems like some, some value would still happen, would still come across.

Interviewee: …maybe? I, mean, I never I never say never. That is one thing I learned through Y Combinator, is to never say never. But, you know, it takes a lot of organization to do these things and like, I wouldn’t really recommend distraction for founders, I mean we serve it up to the founders, they don’t have to worry about all the time it takes to like organize the guest speakers and to arrange for the food to be cooked and all these different things. But, I mean, informally, of course you can, you can, reach out in your community and organize like, you know, meet-ups and getting to know other, other founders. Because it definitely, definitely helps to know other people that you can reach out with you’re struggling with different problems related to start-ups.

Andrew: Yeah, I can imagine the amount of work that goes into it. People don’t know that even doing these interviews, to just line up the guests. I’m so lucky to have Jenny here as the producer to help me out but its still a lot of work for two people.

I: Yeah.

Andrew: Before the interview, Roman Kocho, I hope I am pronouncing everyone’s names right. He asks a, “How can you get an application noticed by Y-Combinator?”

Interviewee: [Giggle] How can you get your application noticed? A.. build something good. I think if you, if it’s more than just an idea, if you have something to demo, that definitely helps. You know, it’s hard. You know, it’s a lot, alot of different things that we look at. Like, how impressive do the founders seem? Have they build things before? Are they, you know, a big deal at their other company, have they done all these other impressive things. The most important thing is like, how they describe, you know, their, the problem, like, how do they articulate that. You know, again, we usually invest more in the founders and not so much the idea. So if you can sort of show that you’ve build something impressive before and even if that means, like, playing around on weekends, building something just for fun. Like, do that, if you’re not sure if you want to do a start up. Build something for fun, try it out! And chances are maybe you will build something that even a few people like and if you’ve built something before that usually stands out with us.

Andrew: I see, Casey Allen, Why doesn’t Y Combinator only back founders with past success? At this point, you guys can just pick the people who’ve had past successes and only back those proven entrepreneurs . Why do you, why do you back new entrepreneurs he’s asking?

Interviewee: Why do we back new entrepreneurs? Like, new entrepreneurs have some much potential in new entrepreneurs. You know, and, and there are definitely successful entrepreneurs who have come through YC. Certainly, a, there’s some, some big examples there and we’ve had repeat founders, we’ve had people that we’ve funded that come back again for their second start up. But, you know, new entrepreneurs are a great source. Why wouldn’t we fund new entrepreneurs? You know.

Andrew: Okay, I’m surprised by the way that there are entrepreneurs who’ve gone through the program. Who could get funding just about anywhere now. Who could probably get funded by other people in the class that they were in at Y-Combinator, who still want to go through the program. Let’s see, Michael Rekoskiee says, a, he asks, what social skills make for a successful entrepreneur team?

Interviewee: Social Skills? Well, well, definitely being reasonable and being able to communicate and get along as co-founders. That, that’s really important. Social skills like its great if you can talk, do some business talk. Like, if you can communicate well with investors, that’s a major bonus. Because, we get, there are some programmers who prefer to be sort of in, in their home office programming the whole time and don’t like to go out and talk to users. Or, hate the idea of fund raising is just overwhelming. And so I think it’s important to be able, like, first and foremost to be able to actually talk to your users and to have some of the social skills to engage them. That’s, that’s, really critical. And then if you can, like, talk to investors, that’s really good. And I don’t what the social skills are, other than just describing as ability to talk to people, that’s, that’s important.

Andrew: Social skills are big…
Andrew: Communication skills are big. People earlier when we got started said wow she is just amazing, she can communicate well and was never going to look at the chat room here because she is going to be so focused on what she’s saying. What I’ve noticed is, and absolutely here, you’re a great communicator. I’ve noticed in these interviews that entrepreneurs, in fact any guest who writes can communicate exceptionally well and the ones who aren’t writing on a regular basis have a harder time expressing their thoughts. You notice that?

Interviewee: I’ve noticed that a lot of good people we have funded are amazing communicators, but I don’t know if they write actually. I really don’t know. You know, I was an English major, and I’m not saying I can write, but I have always felt writing just helps you articulate things properly and it’s more just being comfortable talking to people. Some people aren’t just comfortable talking to people.

Andrew: You’re writing a new book now. What’s the book?

Interviewee: Well, I am working on another edition founders of work. Just same format with different people.

Andrew: What’s the focus on?

Interviewee: With the same focus. I’m not really…. I’m doing it so slowly because I have different circumstances than when I wrote the first book. We funded 200 companies at Y and C, in our downtime. I put that in quotes because it doesn’t really exist. In our downtime there is always something going on with one of our older companies. That takes up time, you do lots of events, we have start up school that takes up so much of my time and angel comp is coming up. We do a lot of these YC only conferences, where we have experts that are a part of the Y Commentator community and they come and we do discussions and fund raising. You know, we have all this stuff going on and I have a 14 month old son now and that severely restricts my free time. So, I hate talking so much about work…working on a second edition of founders at work. Interviewing new people because I think you can learn so much. There are not just x amount of people you can learn from, there are just so many people with interesting stories. So I’m going to work on that slowly but surely.

Andrew: So the interviews now, you’re doing by Video Skype which I’m doing now. I remember when I talked to James Han the founder of Hoddinott. He said that the reason he was so comfortable sharing his story with you was… I think he said you had coffee with him, it was a relaxing environment and I remember thinking that’s a challenge when the internet is breaking up like it did a moment ago when you were talking, when your not in the same room, there is a little bit of a lag because of the internet connection. How are you finding it doing interviews this way? What’s the difference?

Interviewee: Well, what’s the difference? It’s night and day. The reason I wanted to do the founders at work series, the reason I even started this, you helped inspire this so thank you. I felt like there were so many interesting stories going on with just star alumni. I mean there are so many companies, so much you can learn, but I knew how hard it would be. People would say, you should do commentator at work with just commentator alumni and I thought yeah, but I’d never wind up doing it because it takes so long. So, you inspired me to do these video interviews and damn are they hard. I’ve only done a few, I was supposed to do Wufu this week, but I’m doing it next week. There is like some audio disaster going on, the first interview there was this some echo in my ear; I could barely understand what the RBNB guys were saying. I’m hoping that will only improve. I have to sort out those kinks, but I’m having so much fun doing the video interviews. I hope they are interesting to people, but they are night and day. The book took 2 years to finish, it was so time consuming and you know I still prepare a lot for the Y commentator interviews, but I also know a lot about them. I have that advantage that I know some the inside things, inside stories and interesting things to probe on and I don’t have to start from scratch, but I’m going to be in good time. I have a lot to learn, maybe you can help me, I have a lot to learn in being a good interviewer, you have to be in person, I found with the book, but these interviews on Skype seem to work well, but I would never to an interview for founders at work unless I was with the person in the room. And with James Han, we had lunch together, that was a fabulous interview.
Andrew: Yeah, he said he felt the same way. I, you know, I keep hearing people complain that the iPad doesn’t have a camera in it the first version is without a camera…I’m talking to successful internet entrepreneurs with all the bandwidth in the world and we still have hiccups in with audio and the video and you want to take this technology that still doesn’t work perfectly with people who are experts in technology and cram it into the iPad that’s supposed to work with anybody? It doesn’t make sense, we’re still not there, but, as anyone who has now listened to this interview for a little over an hour can see, there’s still a lot of value in having conversations like this, with out without the tech issues. If you bring somebody on like you who has experience, who is willing to be open and share them, I know it is valuable even if every five seconds the technology crashes, or there’s random sounds. So all that’s to say, actually before I say good-bye, just gonna say thank you. What advice do you have for me? You know I’m constantly out the look-out for new ways to move to do better, what advice do you have? What can I do better?

Interviewee: Gosh, how can you do better? well I’ve seen some of your interviews and they all seem great, I think you have a good way of making people feel comfortable, like right now I feel like I’m just having a conversation with Andrew, I’m not nervous about all the people that are listening, and writing about it on Hackernews, I’m not even thinking about that and that is a real key in getting information, is to make people feel comfortable, trust you and share the information, so I think you do a really good job at that. I mean, Just try to elicit interesting information, I don’t know what else to tell you to improve. I don’t think your interviews are fluffy, i think you can learn important stuff from, easy questions, that seem easy like, ‘what surprised you the most?’ That seems like an easy question but you can learn really interesting stuff. So I don’t know what I’d tell you to do to improve, I don’t know if it would improve things to do face-to-face interviews, you’re in Buenos Aires right?

Andrew: For a few more months yeah

Interviewee: Okay, y’know, test it out maybe, try out one interview, if you ever come back to where there’re entrepreneurs, sit down with someone face-to-face and do a video interview, and see, test that out see, if it works better, I don’t know.

Andrew: I really would like to do that, especially weeks like this week where things just break apart, I don’t know if you noticed it, but as we were talking to the IT person here, in the office, came in to check the internet, I said ‘you GOT to make sure that Jessica Livingston’s interview has no problems at all and so I should go back and thank him. I’ll start though my thanking you, thank you very much for doing this interview, I’ve been a fan for a long time and I’m really glad I got to spend this time with you and learn directly.

Interviewee: Oh well thank you so much, it was a lot of fun Andrew.

Andrew: Thanks, and I hope to meet you in person

Interviewee: Absolutely, look us up when you’re ever in Silicon Valley

Andrew: Oh I will, thank you, and guys come back give me any feedback, let me know what you thought of this interview, I often ask my guests what can I do better, with a hidden goal of having somebody in the audience saying “you know what? Andrew really wants this feedback, I’ve got some idea in my head, I know he’s open to it, I’m gonna email him and give him that feedback,” and so if you’ve got a suggestion, come back to mixergy, give it to me, there’re tons of different ways to reach me and help me through here. All right, Jessica, thank you very much, and see you guys all in the comments.

Interviewee: Bye-bye.

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[This interview was suggested by the Mixergy community.]

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  • Fred Gantz

    “When I asked her co-founder at Y Combinator, Paul Graham, he said she has a “social radar.” “She is very rarely wrong,” he told me.”

    What else is a guy gonna say about his wife ?

  • David

    Andrew, you asked for suggestions. I think your show is great, by the way. Only one came to mind: What about reviewing the interview after the fact, and doing a short supplemental interview with questions that you come up with when you have more time to think, and perhaps what others suggest. Basically split in the interview into two sections.

  • JesseAldridge

    Well, if you really want feedback so badly: Maybe you could consider making a “highlight reel”. Pick your favorite 10% of the interview and cut the rest out. It would no doubt be an arduous process, but over an hour of footage is probably too much for a lot of people.

  • http://www.forouzani.com Moe

    Finally! I waited a long, long time for this interview… was visiting the frontpage every few hours just to see Jessica's interview, it took longer than normal, but it's great.

  • http://mixergy.com Andrew Warner

    Entrepreneurs they backed have told me the same thing.

  • http://mixergy.com Andrew Warner

    I hadn't thought of that. Thanks.

    A few guests have asked to come back for second interviews. I'll see if I
    can do that.

  • http://mixergy.com Andrew Warner

    Jesse, this is a great idea, but I can't do it now. It would take too long
    to do that much editing.

    But I often think that the short video you're suggesting would be more
    popular than the full interviews I publish now.

    Good idea.

  • http://mixergy.com Andrew Warner

    Thanks Moe.

    I've wanted to do this interview for a long time. I put it off because
    Jessica is such a good interviewer that I wanted to improve before having
    her on.

  • http://www.girlstartup.com Girl Startup

    Great interview. It was really nice to see a down-to-earth, “switched on” woman helping entrepreneurs to grow. She's very perceptive :)

    I see this really down-to-earth trait in a lot of entrepreneurs which is great and nice to see. Knowing that you can be “nice” and be successful at the same time is uplifting.

  • http://twitter.com/prachisahoo prachisahoo

    Hello Andrew

    I was quite inspired by this interview with Jessica and you did a great job. I have been a huge fan of hers since I read “Founders@work”. Liked the 1 hour version since I could listen to it when driving to my client location (60 miles from home) and while on treadmill. The long interview is helpful when anybody is trying to understand how that person (Jessica) is different and derive inspiration out of it.

    However, I do agree with Jesse that a “10 minute summary” is helpful when people are tied up and still dont want to miss the impotant advice. The summary does not have to be an excerpt. May be you can do just an audio (mp3) version and summarize important points. Thatways you wont need editing.

    My 2 cents.

  • http://mixergy.com Andrew Warner

    Thanks. I'm looking forward to meeting her in person.

  • http://mixergy.com Andrew Warner

    For now, it'll have to be 1-hour interviews, but in the future maybe I can
    create a tighter-edited version too.

  • http://www.Escapingthe9to5.com/ Maren Kate

    This absolutely rocked! Made me want to pack up and move to SV today :) truly inspirational interview Andrew, Jessica was amazing.

  • http://mixergy.com Andrew Warner

    Thanks Maren.

  • http://battledish.com tracy @ladyleet

    great interview, andrew! thank you for providing us with this knowledge. :)

  • http://mixergy.com Andrew Warner

    Thanks Tracy.

  • Alex Tveit

    Awesome interview. Wish I could have been there live, since it was one of the ones I was looking forward to the most. I really do think that there is somewhat of a movement of entrepreneurs helping entrepreneurs, and Jessica's comments and opinions definitely helps further that viewpoint.

    Thanks for a great interview from both of you!

  • http://twitter.com/Shanzzenith Shanz

    Great Interview! u finally got hold of her finally! I am reading her book, you can learn a lot from her interviews, she touches on right questions.

    P.S For some reason your voice is barely audible I had to stoop to my speakers , I put full volume on laptop and quick time. Could you amplify maybe next time :D

  • Tim

    Her voice is annoying as hell.

    Just being honest.

  • http://mixergy.com Andrew Warner

    Alex, we're live @ 11am Pacific Time on weekdays. If you come watch, say hi.

  • http://mixergy.com Andrew Warner

    Thanks Shanz.

    If anyone else is having trouble hearing my voice in this interview, please
    email me: http://mixergy.com/contact

    If I hear from more than 5 people in the next month, then I'll ask my editor
    to recut this interview for you.

  • http://asable.com/ Giang Biscan

    Thank you, Jessica, everyone has been asking for you for so long. This was a great interview. I really admire how Jessica comes across so friendly and down to earth.

    Andrew, thank you for mentioning about me. I can't express how proud I am to be a part of Mixergy, and how grateful I am to you for that.

  • http://mixergy.com Andrew Warner

    Thanks for everything you're doing to grow this site and community.

  • ianalexander

    Founders at Work is constant go-to for inspiration. Underlined. Sharpied and dogeared. Great interview with a smart lady.

  • pocketlint

    I am going to disagree with the degree of usefulness of this interview with nearly everyone who heaped praise on Ms. Livingston in this comments section.
    This interview has been the MOST LOW-ON-DETAIL in a long time on Mixergy and I've been around since the early days.
    The import of Ms. Livingston's insights rank somewhere near the finesse and detail of an episode of Rachel Ray's cooking shows to draw a parallel.
    A great deal of your interviews are superbly rich in deep insights, pivot-pertinent answers and other meaty specs that can only be possible when the host doesn't shy away from asking the probing questions.
    To put it bluntly, I'm sure your visitors and subscribers wouldn't keep coming back if you fed them scraps.

    This interview was just an anomaly, an errant diversion from your usual interviewing style.

    You are in your element when you rain on someone's parade – which was exquisitely epitomized in the 37 signals guy interview where you disagreed about the scope of one's success and how it would be garden variety for it to be on a small scale. That it would really be not success at all !

    Long story short, it is lame for someone at the helm of a major startup-funding farm to dish out such cherubic niceties and boiler-plate stuff.

    I challenge anyone to go through the transcript and point to a nugget of wisdom from this woman that they couldn't have arrived at themselves after a fair bit of storming.

    Too many motivational-coach grade answers, too few secret-sauce-revealing answers. Real blase.

    Funny how it took a bad interview to elicit a comment out of me ! This is my first comment ever !
    I liked the interview with that forum guy (Sanjay i think) not so long ago. pretty insightful stuff there.
    other fun but probing interviews :
    the crunchpad guy
    Matt Mullenweg
    tetris guy
    alex ohanian

    Good Luck with your future stuff.

  • http://mixergy.com Andrew Warner

    Glad you're commenting. Good to meet you.

    But I disagree with your take on this interview.

  • http://mixergy.com Andrew Warner

    Guy Kawasaki showed how marked up his copy of the book was. Sounds like your
    is the same.

  • http://mixergy.com Andrew Warner

    Glad you're commenting. Good to meet you.

    But I disagree with your take on this interview.

  • http://mixergy.com Andrew Warner

    Guy Kawasaki showed how marked up his copy of the book was. Sounds like your
    is the same.

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