The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host)

27:12Absolutely. Okay. When Eddie and Darshan applied, they were not doing the sneaker company. They were doing this group sort of book a book a group dinner at a restaurant with people you don't know as a way to meet new people. And for some reason, I love the idea because I thought maybe it could be like a secret dating, like a Trojan horse for dating, sort of site. But I really loved the two founders. And one of the reasons that again, they had this passion about their idea. But they had worked, they had had like this cream puff company before that they had run. And they just told these stories about how hard it was.

27:54And they all this stuff. And I for some reason just thought, these are hustlers. These guys are scrappy. They're going to make this succeed. And they didn't make that company succeed. But they pivoted and made goat succeed. And it's doing really, really well. And I remember that one. I definitely had to convince. I mean, not that Paul Robert and Trevor didn't like them. But I think they really didn't think the idea was that great or just sort of where we have to fund them. I love sharing these stories. If you have more to share, please keep throwing them out there. So a few things I've noted so far, things that you look for.

28:31And I think it's important to note, this is very early stage evaluation where the founder and the team is incredibly important because the idea off of shifts. Oh, yeah. This is early as it gets, Lenny. Yeah. Oftentimes, just an idea, I imagine. Yes. So a few things. So so far, things that you found to be really valuable to look for. One is this idea of making just making should happen, showing signs of hustlers, just like getting shit done, abamos, things like that. And then I think along the same lines, just like passion for this for this idea and just like care almost charisma. Is that is that how you think about ours?

29:09Is it just like, I hate using the word charisma because I wouldn't there are a lot of charismatic people who are are full of baloney and are just doing a startup because it's a cool thing to do now. And I wouldn't want anyone to get fooled by charisma. There has to be some substance behind that charisma of course, we all love talking to more charismatic people than less. And I've certainly talked to my fair share of totally uncharismatic people, but sometimes they're really good founders too. You know, if they know what they're doing and care about the user and are fixing a problem that they, you know, have a deep connection to so I don't want to say someone who's charismatic, but it definitely helps because as you know, as a founder, you have to do a lot of sales and you have to recruit people and you have to convince investors to fund you and you have to convince users to use your product and all this stuff.

30:13So it does help. It does help being charismatic definitely. So okay, so there's being like super hustler making should happen domain expertise, something you've mentioned a few times just like having deep domain expertise in area. And I think that's probably where they probably don't pivot oftentimes where they've actually have experience in that specific problem. They might pivot a little bit. They might pivot a little in terms of the actual solution. They might be trying to solve a problem and the first attempt doesn't really work. I haven't mentioned earnestness though. Oh, do tell. earnestness is like one of the most important because earnest sort of to me is bucketed with authenticity and to be a successful startup founder, you have to care so much about the problem you're trying to solve.

31:04The users you're serving and being earnest about it is so key to success. I mean, there are so many wannabe founders, so many people doing it because it's cool or they think this idea is cool but they don't really deep down have what it takes. And I think we always try to fund earnest people. What does earnest look like in practice? How does that come across? I think it means being sort of humble about, you know, and if you get asked a question in the interview and you don't know the answer, they say, you know, I don't know the answer to that. I'd have to think about it. Or I don't know the answer.

31:50I've given it some thought and here's what I have come up with. And they're just honest about things. And they're not trying to sort of do whole smoke and mirrors thing, which we've definitely gotten people like that that like avoid the question or are doing it for the wrong reasons. I mean, yeah, I remember there just there was one group that were like 45 -year -old men and they were building an app for like teenage teenagers in fashion. And I remember just thinking, at word with us, why have you chosen teenagers in fashion? It was so clear that they thought they could make easy money. And it wasn't because they cared about fashion.

32:33It wasn't because, oh, I have, you know, a daughter who's really into fashion and I've seen this need. It was just like they made up the idea, you know. And I, that is not earnest. That is not authentic to me. You talked about it. So there's this earnestness you look for also not being defensive. Kind of on there's this also spectrum of confidence and people believing in what they're doing. Do you have any thoughts on just how to find that? Like, what does that look like when they're too defensive versus they're just confident and they know what they're talking about? Confidence is good. You definitely want confidence.

33:06I mean, it's hard to, I think you can see it when you experience it like someone you can someone who's confident in answering our questions, but isn't defensive. There's definitely a difference. And I don't know this is why I'm saying it's sort of hard to articulate these things. But confidence means you can say, I've thought about that and I don't know the answer. Like, that's confidence, you know, and they'll say, but here's what I do to try to figure it out. Here are my plans to do to address that. Yeah, confidence like is I should have put that up front because that's very important, especially when it comes to fundraising, you got to have you cannot go into an investor meeting lacking confidence.

33:50You can come into YC's interview lacking confidence, but we will then help you in the next three months to gain more confidence. And by the way, one of the things we do to help people gain more confidence is to make them believe that their their startup is a great investment to help them like create a startup that truly is possibly going to make money or at least worth being a good bet. That's the thing. Early stage, the best you can offer is like, I might not succeed, but I'm definitely a good bet. And you know, we help them with their product, we help them with their ideas and we help them that by demo day, they can get up on stage and legitimately say, we're a good bet.

34:37And here's why. Let me tell you about our idea. And so we definitely help with confidence. Awesome. A couple of other things you mentioned earlier just unpack a little bit. So being committed, something you look for and co -founders getting along in terms of committed, imagine these are like very practical things, right? Like how are they actually going to stick to this? Are they actually excited to work on this? Maybe talk about that a little bit. We all know how hard startups are, but I think you don't really know how hard it is until you actually do it. A lot of people would start a startup still having a job at Google or wherever.

35:11And they do it on the side because I do recommend if people are just getting started and don't want to raise money yet, you know, starting it on the side is a great way to get going. But at some point, you have to commit. You have to burn the boat because we found that founders who were still getting a paycheck and health insurance, once the going got tough, they did not quit their job. And you need that deterrently, like you sort of need that desperation. Like I have to make this startup succeed because that it's my job, you know, not like, oh, I'll just stay at Google. You need that. And we found that founders who weren't leaving their jobs, it was just not working out or like that co -founder would always wind up leaving the company because they didn't want to actually leave their job.

36:01And you know, that's fine. There are people that can't leave their jobs for financial reasons. That's fine. You just shouldn't be starting a startup if you're not going to be prepared to leave your job. So that's the leaving of the job thing. And the co -founders getting along, I mean, oh my. I spent a lot of my time at Y Combinator when I was there all the time, full time, you know, mediating co -founder disputes. And so many startups died or had near -death experiences because the co -founders didn't get along or broke up. It just happens all the time. And so that's why I think during interviews, I was desperately trying to search for any clues that the co -founders didn't get along or if they like blatantly contradicted each other.

36:52But you could also tell if they were answering, you know, finishing each other's sentences. You know, like I love co -founders that have a history together. Either they went to school together, they went to college together, worked together, maybe they're siblings. Because when you have a long -term relationship, you trust each other and you know each other's weaknesses and you have the same, you're usually on the same page, you know, with your aspirations and everything. It's really scary when two founders get together just to start the startup and don't have any history. That, that massive red flag.

37:31Sometimes it works out. Like in the case of Dropbox, Drew and Arash, you know, both went to MIT, but I think they didn't know each other before they started Dropbox and it worked out. But most of the time, it doesn't. So we've talked about co -founders getting along looking for defensiveness, domain expertise, the sign of making should happen, earnestness. Is there anything else that we miss that you look for in the founders that tell you maybe we should, maybe we shouldn't? Relentlessly resourceful. I mean, that's sort of Paul Rodehole essay on that. I mean, every founders different, I never try to say, oh, this person doesn't have this, I'm not going to fund them.

38:14You always have to, everyone's different. But I mean, you're an investor. I'm curious, do you, I mean, do any of these things surprise you or do you care about these things too? Absolutely, absolutely. I actually try to avoid precede and early, early stage because I'm not amazing at it. Maybe this is why I want to learn how to build my social rivers. Oh gosh, okay. Yeah, tough. It's so tough. It's like so few things actually work out. Well, it's because you don't have a lot of data. If someone is just applying with an idea, you have very little data. You can look at where they want to college, what have they built in the past?

38:53That's always a great predictor of their ability. And so on the on -wise these applications, we ask them what project have you worked on before or whatever. But it's really hard to tell when you're the first investor. This episode is brought to you by Vanta. When it comes to ensuring your company has top notch security practices, things get complicated fast. Now, you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27 ,000, and one, HIPAA, and more, with a single platform, Vanta. Vanta's market leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risks.

39:36Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1 ,000 off Vanta when you go to vanta .com slash Lenny. That's v -a -n -t -a .com slash Lenny. When did you first notice that you had this social radar -ish skill and you're better at this than other people? Paul used to always call me Detective Livingston. Before I was a social radar I was Detective Livingston. I cannot help myself. Noticing weird thing. Just dumb things. If Paul had on a yellow t -shirt and then an hour later came in with a blue t -shirt, I'd be like, why do you have a blue t -shirt?

40:29I have to understand what happened in that hour where that t -shirt is different. I just, or people's, their relationships would drive some. I was always like this, and I think it goes back to my childhood. I spent hours and hours on the phone with people with my girlfriends like dissecting situations and then all through high school and college. I mean the amount of time we wasted discussing social matters with people and boys and things like that. It was just frightening how much time I wasted, but I just was genuinely interested in it and what drives people and why did this happen? I don't know if I ever noticed I did this, but it was just my point is it's always been a part of me and I definitely notice and have an aversion to like phony people.

41:24I've never been one to fall for someone who's super phony and tried to have them as a friend or anything. I just can tell and I hate it. Do you feel like it was almost all genetic or do you think there's something in childhood that pushed you to be good at this? I don't know. I really don't know. I've w - so this is why I think I'm going to be a bad guess because I can't give practical - I can't give a practical understanding. I mean I don't really think it's - I don't - you know I can't say other people in my family are like that and I can't say that it was part of my upbringing. It's just - I just notice these things.

42:04I don't know. I mean I should be paying attention to other things, but I'm not. But I'm paying attention to this. Like I'll give you an example - please - so I looked up your bio to read a little bit about you and I loved the Dalton Caldwell podcast. I listened to that - fourth of the popular all time. Dalton's was? Yes. Oh, good Dalton. That's awesome. Yeah it was really good. I really like - I learned a lot from it. I love listening to Dalton. But like what I really want to know about you is on the release that you sent - or on the like instructions for this podcast you said there might be some edge cases where your podcast isn't good enough to go out.

42:50We just want to warn you. And like all I could think of is like what prompted that? Who? Who? Who? There has to be a story of what prompted that. No one else would be attaching that, but I'm just so curious. It's like it's so weird. I'm just a weird person like this. Yes. I did add that. There's a story basically is just an episode that was an amazing and we didn't have that caveat in the prep beforehand and it felt bad to tell the person. See, I knew it. I knew that that had happened. It's exactly right. Is there a kind of a way you've thought about honing this skill over time. Like once you kind of got a sense, say if people keep telling me I'm really good at this, is there something you've done to help strengthen it?

43:35No, but one of the things I do try to do is sort of reinforce like sometimes I'll have a feeling about someone. Maybe we fund them, maybe we don't. Sort of like to know what happens a few years later, I like to follow up. There definitely have been some situations where I haven't liked someone that we funded and it's taken five to 10 years before they failed. And in some cases, for a bad reason, where I'll say, oh, thank God, I was right about that. I did have this feeling. Or I knew they'd be successful and the goat guys who I was saying before there was definitely a period when grub with us their first startup wasn't doing well.

44:26And they were starting that maybe some people would have given up on them. And now I can say, I was right about them. That feeling was right. So I do try to sort of follow up with some of the really strong gut instincts that I had to see if I was right. Often when I have a gut instinct, it's like a negative thing. So we wind up not funding someone. So I really need to know if that person went on to be super successful. And I will answer your question right now. There's no one that I had a strong dislike for, that I sort of said, we should not fund them that has gone on to be a super success. Thank God.

45:10Wow. Interesting. I mean, it doesn't happen all the time that I really put my foot down. But sometimes I have. And is this feeling, is it like a visceral body thing for you? Or is it like intellectually, you're like, notice, hey, this guy's interrupting her and this person? More intellectual. But it does come from inside. I don't know how to hone it. I can't, it has to come naturally. You have to have a natural interest in sort of people. And so I'm sometimes not listening to all the words and I'm sort of just observing them. I don't know. Have you ever been tricked by someone where he didn't see something you should have seen?

45:50Is there anything there? Oh, yeah. For sure. I can't really talk about the times I've been tricked just because I don't want to say anything really negative about people. But there was, well, there was one example that I do feel comfortable sharing. Ilya Lichtenstein of mixed rank. Do you know the guy that like stole billions of dollars in Bitcoin from a crypto wallet? Do you not know this crazy, crazy story? Like I think he's in the joint now. He was definitely convicted of this and his wife and they stole like billions of dollars. Yeah. And I definitely don't remember thinking anything bad about him or thinking he could be that kind of person.

46:42So that definitely, there've been some, some duesies like that where did not see that one coming. Oh my god. I think what's extraordinary about the fact that that happens and rarely is that your interviews are 10 minutes long and so very little time to actually find all these things. Plus their actual product and idea and growth strategy and all these things. Well, you find a lot can come in reading the application. That's a lot of like work at the beginning. You read the application. But then the 10 minutes is kind of as long as you need in most cases because we found when they were longer like 20 minutes, you'd know in 10 minutes and be like twiddling your thumbs, trying to get through the interview for the next 10 minutes.

47:25So we kept them short so we could interview more people. But there have definitely been cases where we've issued people accepted them and then very soon afterward we're sort of like, like sort of crestfallen like, oh, these people are very limp. This what were we thinking? Definitely. We've been tricked in that respect all the time. Or, oh gosh, they seem so impressive in the interview and now they're just posters. You know, can't really do anything. Like definitely we're I'm tricked all the time in little ways. Or like I didn't notice two founders didn't get along and then one co -founder goes missing.

48:08You know, a week into the program or something crazy. There's all sorts of crazy stuff like that that happened. I think in the game you're playing, I would expect some things to slip through. You said that there's been kind of an operationalization of some of the things you used to look for in founders. Now that you're not actually in the process, is there like a Jessica as a service sort of thing? What kind of stuff have they built that looks for the sorts of things you used to look for in the interview process? No, it's all just stuff in the application that automatically like flags certain things.

48:44I actually don't remember all of them. But it's just all it is is a please pay attention to this reader of the application. It's not this disqualifies anyone. It's just please pay attention. And those are things like I mentioned, like a really crazy equity structure. Founders not quitting their job. Things like that. That it's important that someone is voting on them and then interviewing them knows because I would often some of the questions I'd ask at the end of the interview, I'd say it looks like you have 90 % of the stock and your co -founder only has one. Can you tell us why that's the case?

49:28And maybe they could make a case for it. You know, who knows? I you know, but at least I'd ask. So the flags just say pay attention to it. Amazing. So if we were to zoom out in early stage investing, the main thing you need to get right and value it as the founder, the social radar skill that you've had from childhood is such an incredible advantage in doing this well. And you could basically say YC is what it is because of this unfair advantage that you all had in the early days. I'm guessing many people listening to this are like, I want to we need a Jessica and our team. We need to build this skill ourselves.

50:08We need to figure out how to integrate social radar into our process. I know you're going to hit this question, but just give me advice for people that want to try to build this skill get better at this. Notice some of these things. I really think that our advantage was that my three co -founders were deeply technical people. And I think a lot of investors back then weren't a lot, you know, didn't have that background. And I think that that background really helped YC choose good founders. So I don't want it to make it sound like, you know, it was that big of a deal. But advice. Advice for how to hone.

50:52I mean, I think just try to pay attention to subtle cues. If you really feel like, gosh, I am so clueless about these things. Try to just tell yourself, okay, I'm going to go in. I'm going into evaluate these founders, evaluate this investment opportunity. I know I'm bad at these kind of judgments. I'm going to remember, like, do they seem like they get along? Because they're no like trick questions. I don't have any trick questions that you could ask. Or it's just paying attention. Like, have a conversation. Do they understand their product? Well, are they defensive? Like, maybe have your own little checklist that you think about.

51:33You don't have to have it written down, but you think about. And then afterward, you spend some time thinking like, were they defensive? Like, when I ask them, why this is better than the competitor, how did that go? Or ask them, maybe do have some questions. Like, if you don't know how long they've known each other, ask them that question. How did you two meet? How did have you ever worked together before? How's it going? You just be a little bit more conscious about asking these types of questions to reveal, like, some key information for your investment decision. That was an awesome summary of a lot of the stuff we talked about.

52:12If anyone ever doubts that you are very good at this, Paul tweeted this quiz, reading the mind in the ice quiz that I took. It's incredibly hard. You basically see a bunch of eyes and you're supposed to judge their motion. And it's really hard. And you got 36 out of 36, which are both my mind. I did, Dale. I do have to tell a funny story about this. So, Paul, sort of like late at night, and he emailed me because I had gone to bed, but I had my thing. And he emailed me, he's like, check out this quiz. I got 25 out of 36. What can you get? So I got my computer out because I was like, I have to beat Paul.

52:53And I did it. And it was really hard. Like, they'd only show the eyes. And then it would say, what is this person thinking? Are they happy, sad, but some of them were really hard to distinguish? Are they irritated or are they angry? Like, it's kind of hard to tell the difference between irritated and angry. And I remember, like, looking into these people, people's eyes saying, what are they trying to communicate to me? Are they irritated with me? Or they maddened me kind of thing. And as I went through, it would tell you if you got it correct. And as I almost got to the end, I was like, oh my god, this is going to be a near -perfect score.

53:32I have to nail this. And when I got 36 out of 36, I was like, yes, and I told Paul, he tweeted it. We then, like, a week later, had this YC event in London. And I swear to God, about 10 people came up to me to talk about this Iquiz and how they had not done well. And what was my secret? It was very amusing. I never thought that anyone would think it would. That interesting. I love that there's this thing that totally shows the skill you have that is better than everyone else. I took it. Every all my friends have taken it after that Sweden. The highest we've gotten is 31 of all the people I know.

54:11Really? Yeah. And I think when people take it, we'll link to it. They're going to be like, how can you get 36 out of 36? You have to look into their eyes and say, what are they trying to tell me? You're, I hope you're not trying to tell me like, you're full of shit with your eyes. I'm feeling despondent. They're just getting that's one of the options. I'm like, what does that even mean? I know. Well, that's the other thing. I told Paul, also the challenge is you really have to understand what each feeling, what that word means. He's like, oh, that didn't even occur to me because he's such a word person and knows the exact definition of every single word.

54:49But I thought some people will struggle understanding the complexities of the emotion. Yeah. I've put the words. I almost felt like I had to do what you did where just like, what does this word feel like when I'm reading it, despondent? That's if these eyes are despondent. I love that tricky shirt. So basically you looked at the eyes and you're like, what is this person trying to tell me? Yeah. That's the best I could do. Amazing. So we're going to link to that quiz. I'm curious what people, if you, if you take it, please leave your score in the comments. See if anyone can get anywhere near Jessica's score.

55:20Okay. So speaking of social radar, you have a podcast called the social radar. Yeah. Let's talk about it. Okay. Yes. First of all, just why did you decide to start a podcast? There's a lot of podcasts in the world. What made you decide to start one? Well, I'm really excited that you're asking that question because no one has ever asked me about the social radars. Yes. I mean, it's pretty new, but we launched last year. I decided to start the social radars because I live off in the English countryside, not really as connected as I'd like to be with Silicon Valley, partly by choice, but I do, I do miss it a lot.

55:54And I was finding that as I was catching up with YC alumni, you know, that would come visit, or I'd see, I just loved the conversations we were having. And I missed that. I missed that connection with these people and sort of sharing their stories of triumph and failure in some cases, but mostly triumph. At the same time, I became obsessed with this podcast called Smart Lists. Have you ever heard of it? I've heard of it. I've endless. Okay. So just for the listeners, it is a podcast hosted by three actors. Jason Bateman will Arnet and Sean Hayes. And they really, they invite Hollywood people, actors, directors, musicians, sometimes athletes on the show.

56:39And the thing is one person, one of the hosts invites the guests, the other two don't know. So there's no preparation. And it's the most fascinating thing. I love movies and I love television. And I can tell you like another weird eccentric sort of gift of mine is I remember every name in Hollywood and know all like their children and all this stuff because I've been reading people magazines since I was 13. So I loved like you'd learn so much about the actors as a people because they weren't talking from a script or their, you know, media messages for promoting a movie. It was like just genuine conversations.

57:18Most of the time these actors knew the people and more friends, and I just found it fascinating. I could not stop and and I thought there should be like a really informal conversation like this with startup founders so people could understand the people behind the startups. And it's not too scripted and not too maybe I don't want to say professional because I hope it's professional sounding, but it's, it's very conversational and authentic. And I was trying to mimic that a little bit. So I, I convinced my colleague and friend Carolyn Levy who of course has a full -time job being one of the amazing lawyers within YC and she's super busy.

58:01I convinced her to do it with me so I could have a partner and crime. And then we just started. And I said, we'll do a few episodes, see how it goes. And we'll keep going if it's fun. And I have had so much fun catching up with all the people I've interviewed. I mean, at this point, I forget how many podcasts I've even done, but maybe about 27ish. 27 that have launched yet. There's a few, and there's a few coming out season three. We're still in the middle of that. I'm still editing some and doing some, but it's been so much fun. And I love it. And I hope that people enjoy listening. I hope I'm not just working this really small corner of the room.

58:42I hope people enjoy sort of unstructured conversations. But people, people open up to me though because what I copied from smart list that I liked, you know, they'd say, hey, remember when we were at that Oscar's party and this happened? Like because they had that relationship with the people they're interviewing in a lot of cases, I feel like I've had that with a lot of people I'm interviewing. And I could say, hey, Brian, remember when you interviewed and brought the cereal boxes, you know, and he could tell, he shared that story. I don't think I knew it before then that they were on the 101.

59:17And the phone went out, you know, the reception went out before Paul said that they were accepted. So I learned a lot. And it's really just fascinating to me. Well, it's an awesome podcast. I've been listening. I'm going to just read some of the guests that you've had on just so people get a sense of who you're interviewing. So you actually just have Paul Graham on the podcast. He does a very few podcast episodes. So that's an unfair advantage. You have their Patrick and John call us in bright, Jessica. You mentioned bright arms strong image here. Tony's like epic people. Emmett Sheer by the way, the week after he was named open AI CEO for like 72 hours, that one launched.

59:55I was like, I could not have planned that timing better. Is there an episode you'd recommend people start with if they were to start to explore your podcast and get into it? Honestly, like I truly believe this. I'm not BSing you. I think they're all really, really good. And there's so many interesting takeaways from every single one. If I were coming to it for the first time, I'd probably choose, I'd look at the guests and say, who am I interesting? Have I stayed at an Airbnb and I want to learn more about that? Or do I use Reddit? Some just see who the guests are and start with someone you're kind of interested in.

1:00:30And I guarantee you'll learn more about this person. So across the podcast episode you've done, I hate when people ask me this question, but I'm going to ask you this question. Is there anything you've any big lessons you've learned, any stories that have stuck with you and you take away so far from interviewing all these incredibly successful founders and people? I love that question. I don't hate that question. Okay, I'm glad. I could talk for an hour just on. I want to learn from you as an expert podcaster because I'm still a noob here. What I've learned the hard way and you're probably will nod your head when I say this is that I'm, I talk way too much.

1:01:05I'm a huge windbag and I hate, I don't notice it now when I'm just talking to you and going off and talking, talking, talking, but when I'm editing the podcast and I'm listening to myself, ask a question in 20 sentences when I could ask it in two. So I've really had to train myself to keep saying short like you want, you want like regular short dialogue, you know, you know this, but you also have to interrupt guests if they're going off too much. So like the talking of the host should be frequent, but short, that's the lesson that I've learned. In terms of content, I mean, every, every single episode is a gem in its own right and there aren't like massive lessons because it's, they're all sort of specific to that person and I never know exactly which direction we're going to go in when we get into things, but it was interesting.

1:02:07There were definitely some themes with like Adora Chong and Tony Zhu of Door Dash where they said they really made a mistake early on scaling into different cities before they had nailed, you know, the original city and that, you know, that's an important lesson. There's lessons for everyone, I think, in addition to really getting to know these founders, their personal side of their personality, there's some great lessons that they all tell. I love these lessons. Is there anything else you've learned about interviewing? That's something I'm always trying to get better at. I love this point. You made a complete, I'd say the same things every podcast through you talk too much as a host.

1:02:46You should let the guest talk. Just ask the question, let them talk. Is there anything else that you've learned about just how to interview more effectively? Remember I've been interviewing people since YC started because I was working on founders at work when, when simultaneously, when we started YC and so that was a collection of interviews. And back then, I can't say I was that good at it. I've gotten much better. And then I've since gone, I used to do a lot of interviews at startup school on stage with people. And now the podcast, I think one thing that is that the guests trust me, they trust that I'm not going to try to like have a gotcha moment.

1:03:27I'm not trying to lure them into saying anything controversial. I mean, do I love it when they say something that hasn't been said before? Yes. But I'm not trying to trick them. And just like you, I tell them you will have a chance to review this before it goes public. And I think that disarms people. And they say, okay, I can open up because I know if I regret saying something, it's not like talking to a reporter who's going to publish it. Like I care about them, I care about making them look good. And I'd never want to betray their trust. And they know that. So that's part of it too. For me, with the podcast, I just, I have some questions that I do ahead of time just so I have something down.

1:04:11But I also just let the conversation go where it's going. And we get in, we get into some random tangents that I find are really fascinating. Is there a story that stands out to you just like that sticks with you from the interviews that just like, wow, that was such an incredible story. So I'm sure it would be worth less than her. The podcast that really sticks with me is the Parker Conrad episode of Rippling. But we spent a lot of time on Zenefits. Because if you didn't follow that story years ago, the press annihilated him. And in talking to him, I learned why there was a smear campaign, you know, paid for by someone still at Zenefits.

1:05:00There were legal threats made to force him to sign this, sign this legal document that would allow them to have a non -compete in California so that he couldn't start another company. Basically, making his life miserable, disparaging him, stories planted in the press. And I had him come on and I had him tell what really happened, you know. And I even I who have seen so much shit behind the scenes with startups in Silicon Valley over the years, like stuff you just couldn't believe, this was unbelievable. And the thing that really sticks with me is that like no reporter ever, like maybe no reporters listen to it, but no one said like, hey, I got that wrong years ago.

1:05:55I shouldn't have written that. That wasn't true. Let me set the record straight. So he doesn't care. I'm Parker's move dawn. He's successful with Rippling. He doesn't think about this stuff. But I do, I care about justice, you know, and it was a horrible thing that was done to him. And like it, it affected his health. It affected his life, you know. And I just I'm glad to have sort of been a conduit to set the record straight. That's an awesome episode maybe for people to start with if they want to check out the podcast. And then generally I just love this rise of ways for tech people to share their story without this drive to like create clicks and create gotcha moments and things like that.

1:06:38Just this I think people call it techno optimism. This idea of just like tech is great technology is doing great things for us. Let's just tell these stories in a really positive way versus like all the harm that causing technology slow it down. I just and I just want to have conversations that I personally find interesting. I'm very selfish about it Lenny as long as I have an interesting conversation. I tell Carol and this all the time. Like as long as we have like 20 listeners, that's all I need. 20 like really interested listeners. I will keep doing it. I love that attitude. I wish I had that same feeling.

1:07:12What I look for is is a growing. That's the thing. I'm like is it growing at least if it's growing. No matter what is I'm feeling good. I need to be more like that. I don't know any of my statistics. What should I what statistic you tell me as a experienced podcaster? What statistics should I be like have taped up to my mirror every day and track? There's like the correct one and there's like there's a simple one that I look at which is just downloads of the episode. It's like the most basic one used to everywhere. And downloads is a weird one because they might download it and not listen to it.

1:07:44But that's just the one that podcasts platforms tell you how many people have downloaded it. And that's the one that just tells you kind of generally are people listening or people continuing to listen to they cut that they removed from their phone. Like in theory, you should be looking at retention. Like how many people are finishing the podcast episode? Can you tell that though? I thought platforms don't share that with you. Some do. Some do Spotify. It gives you some of that Apple gives you there's there's a worse part about podcasting is analytics are extremely bad and inconsistent. But there's some of those stats.

1:08:18The other one. Okay, here's one to pay attention to is a number of subscribers on the different platforms. People that follow you. That actually is a really important metric to watch. Number of subscribers. Okay. One thing I also this is just my personality. I can't bring myself to do what I want to is ask people if you like the social radars like please subscribe and leave a rating and a review like I would do anything to have people leave rating and reviews. Okay, if you're listening and you either check out the podcasts or you're already listening or please leave a rating and a review and subscribe and follow.

1:08:54Thank you. Can I ask you a question about podcasting really quickly? Let's do it. When you do a podcast after you hang up with a person, can you tell do you have a gut instinct like oh that was a really great one. It's interesting is the ones that I sometimes think holy moly that was incredible don't do as well as I would think and sometimes ones I don't I think didn't go amazing actually do a lot better than I think and I think there's like a difference between the energy and the fun of it versus like the content and the interesting value of the actual conversation. And so sometimes you feel like that was so fun so good I loved it but people are like man and learn anything.

1:09:34So those are interesting that's something I've learned. Okay, yeah because people come to yours expecting to learn things. It's right now I'm getting it now I'm a little nervous I'm going to get asked because I'm not teaching them anything valuable. You're so modest. This was incredible. I think we've taught people a lot of really important and really actionable things and I know you don't think you did but you did and with that we've covered a ton of ground we've talked to every single thing that I was hoping we talked to. Is there anything else you wanted to share or maybe leave listeners with before we get to our very exciting lightning round.

1:10:07No, I mean honestly I can't think of I think I win bagged enough. This was incredible. You talked exactly the right amount of time. With that we've reached our very exciting lightning round. I've got six questions for you. Are you ready? Ready as I'll ever be. Okay, first question. What are two or three books that you recommended most to other people? Well, I definitely would recommend like my first, second and third books would all be PG Woodhouse books. Do you know him as an author asked Jeaves? Okay, so he was an old old school author and he wrote the asked Jeaves books about the you know Butler and not the search engine.

1:10:53And they're so funny. They're just fabulously written. Like his use of words makes me laugh so hard. And so I would specifically recommend like the starter books that I wrote he wrote tons of books and he lived till he was like a hundred. He start with like very good Jeaves or write hoe Jeaves, carry on Jeaves. Those three are really good good books. And then I tend to read so Paul's the big reader in the family. He reads you know riveting books like on Roman grains and anything that has to do with medieval history. I tend to read biographies of people. And so I just especially musicians, especially English musicians strangely.

1:11:46And so I've recommended to a lot of people if you really want a good autobiography because I sometimes hate autobiographies because I feel like people hold back and don't really share everything. Keith Richards, his autobiography called Life is really good if you're a fan of the Rolling Stones at all. That was really good. And then I recently read Barbara Streisens biography called I think it's called my name is Barbara something. And I kept thinking as I was reading this like every female founder should read this book. And you're looking at me like that's so random. But it's because she was such a success within this totally male dominated like world of Hollywood and just treated like garbage and dismissed and you know called the diva when she was very particular about something whereas a man would be called you know a great director and she was called the diva.

1:12:45And I felt like every woman should just read this to inspire them. It was such a great book long but very good. Incredible recommendations. Next question. Do you have a favorite recent movie or TV show? I don't tend to watch recent movies. I watch old school movies like from the 50s through the 90s and stuff. My favorite new TV show just up to the top of my head right now is Clarkson's farm. Have you heard of that on Amazon? No Jeremy Clarkson is in a show called Top Gear. I don't watch that but he lives out in in the English countryside. He has a farm and he decided that he'd farm it and the whole show is about him getting into this business that he knows nothing about.

1:13:31Everything goes wrong but it is hysterical and heartbreaking at the same time. I've learned so much about England and about where I live and the crops that are grown and how hard it is for farmers. He's really shown a light on the difficulty of being a farmer these days and it's fabulous. Clarkson's farm. It has some bad language in it but I do recommend that kids watch it because it's just a good show to watch as a family. If you can deal with a little foul language, foul language, the Brits say drop a lot of F -bombs. Do you have a favorite life motto that you often come back to share with people find useful and work or in life?

1:14:17So boring but I always try to treat people the way I'd like to be treated myself really is fundamental life lesson. It's boring but so powerful and important so I try to live that same way and I think it's a good reminder for people sometimes the most I think there's Michael Paul and I said that clichés are clichés because they're so true they're like so true we're tired of hearing it sometimes that's important to be reminded of them. Who's most influenced you in your career? Who do you think open your life? This person's really had the most influence on me. In my career I definitely have to say my husband Paul Graham I've just learned so much from him over the years and he's such he's such a good person and I don't I think people who know him all know that he is it's just he has such a big online personality either through Twitter or through his essays and so he has a lot of people that don't like him because he also speaks what he believes and he is not afraid to say anything if he believes it's true and needs to be said whereas I'm the exact opposite I'm like oh I'm not going near that I'm not touching that with a 10 foot pole I don't even want to get in someone's crosshairs or fight with someone and I admire that so much like there's so much that he's done with Y Combinator and just in our personal life that is just so admirable and I just I've really learned learned a lot from him it's such a boring thing to like learn from your husband but at the same time I'm gonna extend this I'm gonna win bag a little bit longer I have learned so much from the founders that we funded I mean some of them are just incredible people and and have been through so much and survived so much and built these amazing companies that I couldn't have even imagined when we funded them that these companies would be as successful as they are and they're all you know so many of them are just great people and they now teach me things honestly like Brian Tesske teaches me things the the student has become the master he knows so much more about me and running a business and I often like we'll go to him for advice and so I'm really lucky to be surrounded by so many smart people in the startup world because as a startup nerd I mean I could talk about startups you know and think about them all the time and it's so great to have all these people around sort of lifting lifting me up would you believe that serial experience led to a 90 to billion dollar business today I just looked at how big it got honestly I wouldn't and it's I wish I could say oh I knew they'd be this big yeah but the truth is with all of the super successful startups yeah you can remember feeling very positively about them and certainly feeling like as they went along in the first few years like they're doing really well they're really determined they're doing a great job but you just never really think they don't they themselves probably didn't realize that they'd ever be that big let's face it that's just the way startups are okay here's the actual final question is there a fun story of early days yc whether it's with Airbnb founders or Paul or anything that comes to mind is just like wow what a what a different time that was or what a surprising thing that happened that's funny us because actually one of my ideas I've had lately is that I want to start thinking about writing sort of a yc biography kind of book I don't know when the time is but the point is I have to remember things because it's hard when it's been 20 years to go way back you have to remember specific things that happened I mean yc I just remember the early days being so magical and so pure when we started like no one knew about us no one was bothering us we just did what we were doing with no distractions we were helping albeit a very small group of founders you know eight in that first summer um we were just doing what we love doing and growing organically and no one was scrutinizing us or blaming us for things or you know writing negative news stories about us I mean the negative stories in the press because I'm a people person and I'm very sensitive like Paul's not as sensitive as me and so he doesn't care if there's a negative story in the press that's not true like I do it really like affected me and I hated when we got big enough that you know people would lie about us and say bad things so I look back fondly when we first started of it was the most fun time of my life the most productive time of my life didn't have kids then and I could just help the founders and like learn about all these exciting things that happened in the startup world because it was new to me then the startup world was new when we started why commentator so I had a lot of learning to do and I met all these cool people it was just very authentic like no one was doing it to be cool okay well let me let me ask maybe one other question was there a moment when you felt like YC was working when it felt like wow maybe this is gonna make it there were sort of two moments that I remember I felt like YC was working because remember we started Y Combinator as 100 % like an experiment could we fund younger founders with small amounts of money that was it then that summer we created this batch investment idea and then that became the idea of funding them in batches and that was the first aha moment was after that first summer when we invited people to participate in the summer founders program which is what it was called and remember that first summer had Sam Altman Emmett Sheeran Justin Con Alexis and Steve of Reddit you know those weren't they were in the first batch and the batch thing worked really well because they all became friends we could have dinner every week and bring guest speakers and then introduce them to investors at Demo Day and that that whole batch investing thing was an aha moment and we said oh my gosh let's keep doing this this really works and so we said that was a moment where we knew we were on to something and that's when we then did it in California in the winter but the second big moment was probably it was I remember it was like a year later and no no reporter would write about us investors really didn't you know think that much of us but I remember when Reddit got bought by Condé Nast in 2006 it was that and then at the same time I think it was like Charles River Ventures or one of these Boston maybe wasn't even Boston but it was a VC firm did like the seed program where they invested maybe a hundred K in startups and the press like loved that they like wrote all about this one hundred thousand dollar investment and they'd sort of mention why commentator as doing small investments and then that coupled with the Reddit press sort of made us feel like oh my gosh we are sort of legitimate in the eyes of outsiders became sort of aware of who we were and I sort of felt like we've arrived we've been in the news you know we've been in the press like people are finally being in tension that's amazing and it's funny that right it just one public it's kind of the other side of that that coin I know pretty impressive I mean definitely didn't didn't necessarily think that was going to be happening I know you have to run but I can't help but ask around the city which you just talked about where you decided to invest in batches you wrote this really interesting point that none of us had any experience angel investing and that's where the idea of funding startups and batches came from we decided to fund a bunch of startups of one starting the summer so that we could learn how to invest and I love that you're inexperience in doing it created the structure like that unique weakness less strength is like what led to the way vice operates and I think that's really interesting yeah yeah we definitely didn't wanted to learn more about how to be investors so that's when we decided to do this you know summer founders program where we could invest in a whole bunch at once and then the plan was to go to asynchronous investing like normal investors but we realized that there was something magical about this batch thing so sometimes I always say we love domain experts but sometimes maybe ignorance is sort of bliss and you just discover new things Jessica this was everything I hope it would be we covered so much ground I think people are gonna love it no matter what you think oh good good good good two final questions working folks check out the social radars and anything else you want people to know about and how can listeners be useful to you well you check out the social radars and all the you know podcast platforms apples Spotify Amazon all those and then there's a website but social radars dot com and they can be helpful by just listening to it and spreading the world word because I don't do any marketing for it besides like posting on Twitter just because I'm I'm uh you know you know it's expensive doing a podcast and stuff so I don't do any marketing so if it resonates with you if you find an episode interesting please spread the word and write a review and and rating I was just gonna add that I'm glad you threw that in there Jessica thank you so much for being here thank you so much Lenny it was a lot of fun thank you for me bye everyone bye thank you so much for listening if you found this valuable you can subscribe to the show on Apple podcasts Spotify or your favorite podcast app also please consider giving us a rating or leaving a review as that really helps other listeners find the podcast you can find all past episodes or learn more about the show at Lenny's podcast dot com see you in the next episode