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Dalton Caldwell

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2024-04-18
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2024-04-18
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  1. “I'm exactly the same as effectively they're like, wow, you're just that guy from the videos I've been watching. And it's so cool that you're just exactly like you see him in the videos. And so basically, yeah, if people like what I have to say and they like the videos and apply, do I see, I would love to fund their companies.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “I am on Twitter slash X.com Dalton C is my username. And also, my LinkedIn is pretty good. It's pretty popular. I don't know. Just search for my name on LinkedIn. And yeah, I'd love to see you all there. And then how can folks be helpful? I mean, honestly, it's just great when folks want to apply to YC and do a startup. And so feel free to dive into our other videos and apply to YC. And I'm something that's really special about my job is I get the privilege of getting to fund companies that they already know me from videos and they're shocked.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Yeah, yeah, I think that was pretty popular. So, what I'd be looking for is diagnose, am I a current founder and I have founder problems or am I just looking for general Philosophy type questions. And I really like those philosophy ones. We have one for high school students, and it's aimed, the audience is, here's advice for high school students that are interested in startups. Here's some tips that you should be thinking about. Again, pretty narrow target audience, but I love that episode because we're really trying to speak directly to that audience. And I think it's pretty good advice.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “It depends. Some of the episodes are more for folks that already have a startup and they're dealing with problems. I don't know, some of the episodes about investors or things like that. It's very clear that the audience for those is current startup founders. And there's a lot that are just more life advice how to make decisions and think about. And that is those have strangely become very popular and got a lot of views with non-startup founders, which just a pleasant surprise. And so I'd recommend those for folks in the audience that are not currently startup founders. I don't know. Life tips from top founders, I think, is the billionaires.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “Yeah, embitting to yourself. Yeah, I'm not really enjoying this. And then trying to be like, well, how can I fix it? Having that conversation with you.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Just check in with yourself that you're having fun. And that you enjoy what you're doing. And if you don't, you should probably make a change. Whenever that is. And again, if you're a founder, you're in control, right? You can change your own company. But I think a lot of people go through life and they don't ask themselves this question, like, am I having fun? Am I enjoying, do I value when I'm spending my time on? And I think that you just can go back to this over and over and over again as a good prompt on how to decide what to do with your life.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “It's this little tiny needle, it doesn't hurt at all. And it just takes a few drops of blood, and you do it at home, email it in, and then it has all these blood tests. It's actually really cool. Yeah. And I just discovered that it was one of those cases where I saw. Saw it, and then I later was like, oh, wait, that's a YC company. Like basically, I became a customer and was pleasantly surprised that it's a YC company.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “Like my aura ring and my Apple Watch and all that good stuff, I've been a fan. There's a YSQ lending called SciFox S-I-P-H-O-X I just signed it for and they do kind of home blood testing. And basically I'm trying to sync that at home blood testing thing into all my other devices. I think, I don't know, I really enjoy. The stuff that Apple and other startups are working on and YC companies are working on around personal health. And so, yeah, those are products I'm into.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “I think evidence that they actually have thought about it. Like, as per I said earlier, that they've done research, that they have opinions, that they care about it, right? Sometimes when people answer questions, they're like, you can just tell that it's really superficial and they haven't put much care or soul into their answers, you know?”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “I don't really believe in trick questions, and I think I just start with, hey, so tell me about what you're working on or what have you learned since you started, none of these are trick questions, but I think you can get the most honest and interesting answers by asking the most straightforward basic things and having that be like a blank slate for their answers to draw on. Know what I'm saying? So I like the most simple prompts and let them take the conversation where they want to go.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Well, again, I guess I'm not trying to give you an answer where I sound super clever. I'm actually telling you the wrong answer.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “May be warping what you're asking for, but I like to watch old shows a lot, and so I keep re watching the sopranos and the wire, and it always is different to me every time. And things like that. I think here's a silly answer. I've been really enjoying watching old episodes of Colombo, which was a television show from the 70s and 80s. I don't know why. I don't even know if this is instructive, but it is. For some reason, I'm really into that right now. It's very old episodes of”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “I think a lot of founders are afraid of doing sales and they don't know how to do sales and they think they need these really experienced sales coaches and they need all this training and I'll be like, well, go on to Amazon and find the most popular sales books like getting to yes that everyone reads and just read those. And that'll give you 80% of the way there. You know what I'm saying? Like they want to hire someone for millions of dollars to give them sales coaching. I'm like, well, have you read these really basic sales books? And they're like, no. And so I think as a low cost way to go on Amazon getting to yes, and a few other of the top sellers, I forget the names, and just read those. And that is your crash course on how to be great at sales.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “Depends on basically. Bildta, once you have some conviction, they're like, oh, I think I would have a customer, I think I had at least one person would use this thing I want to build. At least one.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “Yeah, I guess the final thought is, you know, if someone wants to do a startup and doesn't know where to start, just to give you permission to talk to potential customers and try to pre-sell something before you write code and have those conversations. I think somebody folks don't know where to begin on starting a startup. And my tactical advice is start doing customer validation. First, first is building a PowerPoint deck versus trying to raise money versus like all these other things. I think a lot of people don't use that strategy. And basically, if you find people that are really excited and you do line up customers, that is a great green light that it is time to do a startup, right? That can get you down the path. Yeah, I think that's my final advice”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “In my life, a lot of optimism and energy and use that energy and motor to keep me going. And it served me really well, right? Even if lots of stuff I tried didn't work and continue to not work. Again, obvious stuff I know, but yeah, that doesn't mean it's not true, even though it's obvious.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “I failed at tons of stuff. As an investor, I make lots of bad investments as well as good ones. I think in my startups, Hypoted a lot and a lot of things I did did didn't work out. And so again, I just gave you a specific story with Picleys, right? You just heard a specific story there. I guess what I learned is that you just can't let it get to you too much and you got to keep going. And that if you keep going, no one really remembers those as much. And it doesn't really define you. And it shouldn't, you know, fear of failure shouldn't dominate all of your thoughts. And instead, you should use your energy and positivity to keep trying to do good work, right? Because back in the day, if I would be like, well, you know, I guess started trying for me. I guess tech isn't for me. I wouldn't have had a career doing any of this stuff. I wouldn't be working in YC. I wouldn't be advising companies, right? So I always had to have.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “They effectively knew they needed to focus on buyers and on the buy side and build momentum on the buy side. They really understood marketplaces. And so for consumer, I think it's having a sophisticated view of how you get the consumer company off the ground. I think if you look at the Facebook story, them getting 100% penetration on the Harvard campus first instead of launching overall. Again, good strategy would recommend that strategy. So again, the way to extrapolate that is know what your comps are of what companies your archetype is and then look at what they did on the zero to one and ignore what they do today. Don't pay attention to what Facebook does today if you're a brand new startup founder. Pay attention to Facebook when they were getting their first thousand users. What were those tactics?”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “I think it depends on the idea. I think in the case of whatnot, they obviously, it was consumer app and they needed to get users, but they were very intellectually honest on the metrics for how you get a marketplace off the ground. And they didn't just go dump all their money into Instagram ads.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “Again, I'm not saying you're doing anything wrong, but imagine if the OG Airbnb founders took all of your current advice and applied it when they had like four users and they knew their names.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “Happens if you worked in big tech where your product already has scale, and so if you work at Facebook, your job is to launch new little features. Yeah, of course you should make heavy use of analytics and AB testing and split testing in feature flags. Like, yeah, yeah, yeah, it makes sense. But when you have no users, what are you doing? So, do you think that's contrary? What do you think? I'm just trying to argue this advice applied to a startup that's too early is actively not helpful.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “One of the weird things about having lots of startup advice on the internet again, this is one of the reasons we started making videos at YC is a lot of the advice was catered towards later stage companies like, oh, here's how you set up your board and here's how you motivate your sales team. It was all aimed at series A, series B founders, and not for seed stage founders. The problem was seed stage founders would consume all the later stage advice and get really confused. And so the anti-pattern I see is there are lots of founders that are very familiar with your awesome work, which again, I really recommend. I like it. But when you have no customers and you're reading Lenny's guides on how to set up split testing and how you did growth at Airbnb, oh man, that is so dumb. That is so not helpful. And so you see this inclination away from getting a first customer, getting one customer, and talking to that person. And instead, they have like all this really complex growth hacking theory. I think it's all.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “Yeah, I think for contradiction corner, I know where I would start, and I think it's relevant. Your listener, like, I think this is relevant to this. And so, again, maybe, and you could argue this isn't contrary, but here's what I think. I think growth and growth hacking and doing all this analytics, A-B testing stuff is a total waste of time for very early startups.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “I don't actually think they care. I don't think they held it against me because what did I do wrong? I started a company. Like, you know what I'm saying? Obviously, there was some frustration, but I was like, I was a guy who had a company that they invested in. I don't know. I didn't feel like I didn't feel much higher for them. I think this is just how life works.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “This became like a big source of like Silicon Valley gossip, which was like, wow, I can't believe this happened. And so it was just a really weird experience for me as a founder to. To be right in the middle of somebody that became culturally so important.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “Into what was pretty similar to my thing. Again, fair enough, I just have this works. And they did something smart. Again, this is just me talking. I don't know what their version of the story is, but what I think they did that was smart is if you looked on the paid app store charts, the number one app was hipstomatic. And hipstomatic cost money. And what do we know about what people want? They want things that are free that cost money, right? And so they basically built a pretty legitimate knockoff of the hipstomatic filters combining it with the social graph and they launched it and it pretty quickly took off. So of course this is Instagram, right? And so it took off really quickly and like, again, that was like a wild experience for me to be like, oh, this seems familiar. And basically because Andrea Horowitz had like invested in my company was on the board, even though they were investors in Instagram that was like a conflict and they didn't do the deal. And then for whatever reason.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “No, no, he was long gone. Seriously, I know you're kidding, but no, like, literally, I don't know who was left at that point. Tom is long gone. So I was like, well, I should just do a new startup and I should work on something like when I was thinking about. And I ended up starting the company and quickly was able to raise an angel around because people remembered my company from the first one. And the major investor we had was Andreasen Orwitz. This is one of their first board seat investments. Like Mark Andrewson was on my board. And, you know, again, my own set of stories about that, but it was interesting experience. And we launched it. And I think we got half a million or a million users. Like you can go find Tech French articles about it. And it was, we launched an Android and iOS and it was mobile photo sharing and actually was growing pretty well. And then what happened is there was another portfolio company called Bourbon, which was originally a Foursware clone that was built by these two guys. And they decided to pivot out of that.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “Because the person that acquired my company got fired. And there was like, I think the whole work chart got fired. So I don't even know. I didn't even know who to talk to. It was really great. It was a great experience. You know what I'm saying? I wasn't really sure who my point of contact was at that point. I don't think they knew either. It was just a mess. Just Tom.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “Got the juice. He wants me to fix it. Like, we're going to do it. So come up with some ideas. And kind of the best idea that I could come up with at the time was doing something around mobile photo sharing, something kind of like Twitter, but for photos. And I figured with MySpace's user base, that would work pretty well. This was like in 2010. So it was right as the App Store was getting big. And I had a lot of success in the App Store with iMeme. It was one of the top music, top downloaded music apps. And so I was like, wow, the app store was really good. And I was really into apps being the thing. And at this time, Facebook was a little early on. They were trying to do cross-platform mobile apps, if you recall. And their apps were not great. This was, again, ancient history. And so that was sort of like my plan. And then immediately, Hoen Van Nada was fired. And so I didn't even really get onboarded. And so I just like left. I think I worked in my space for like a month.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  30. “Well, it's kind of the same story. Okay, and the way that it's the same story is my separate company, basically I sold my first company into MySpace. It was the music company that I worked on. And they recruited a new CEO who was formerly the COO of Facebook called Owen Van Nada. So again, hilariously part of the same little circle of people. And Owen was like, okay, we need to fix MySpace. You know, Rupert Murdoch's.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  31. “A bunch of nerds that really like the internet and computers kind of doing things that they were interested in. And we're just obsessed with this. Like there was no, they weren't like, gee, should I move to New York? Oh, gee, should I, maybe I should go to law school. Like it was people that were very bought in to stain working on internet companies. And so you'll see these folks just reinvent themselves multiple eras, right? Okay, like Reed Hoffman, right? He was a worked at PayPal, right? And then he did LinkedIn. And then he was like a VC and like, like he's kind of had like all these different eras where it's the same person, but it's almost like a different figure, right?”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  32. “Anyway, it's pretty funny. So, yeah, that's the real story. And then, yeah, I remember I was in downtown Palo Alto at the time. Some of the folks I was friends with were friends with Sean Parker. And this was actually before Sean Parker went to Facebook. He was part of Napster. And so one of my friends was like, oh, we need to get my friend arrived at the airport. And so I ended up giving Sean Parker a ride to the Oakland Airport. And again, what was he like? I don't know. He just basically sat in the backseat on the phone the whole time. But again, my point is I wasn't like, wow, these are going to be really big, successful people that one day will be important in the world. It just felt like.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  33. “Find people around you to hang out with. Interesting theme here, huh? He was cool. He was this really young guy. And he just kind of did that. It wasn't huge. And then he got into other stuff and ended up working at YC, ended up getting involved in hard tech and is now kind of like reinvented himself as. The big mind behind AI, which is again awesome. But if I think about who he was back in the day, he was like a 23-year-old working on a thing for feature phones to find friends in your neighborhood. Their customer was Boost Mobile. I bet you could go find the commercials for loops that Boost Mobile put out on YouTube. Those are actually pretty funny. Have you seen that's commercials?”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  34. “He was just like a guy, and everyone else that was doing, I guess you could call it social networking. That was sort of the people that I knew. There was a few conferences you would go to and there'd be like 30 people there. It reminds me of stories about the homebrewer computer club. I'm not saying this is as cool, but when I read stories about what it was like when the homebrew computer club existed, you have some very small number of people that all knew each other that were real weirdo outsiders that were into this stuff. Okay. And so that's what in the post.com boom Bay Area startup scene, that's legitimately what it felt like. And so I didn't think a lot about the personality traits of these people. They were all, again, they were all pretty different people. But what they had in common is the folks that are now the really big names just had a lot of stay in power, right? So when I met Sam, he had dropped out of Stanford to work on Loot, which is hilariously a way too.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  35. “Back in 2003, being in Silicon Valley and being interested in startups, they're just, it was a really small space. There just weren't that many people that were into this stuff. And so I remember I cold emailed Reed Hoffman when LinkedIn was like 12 employees and he just responded. And he's like, oh, let's have lunch.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  36. “The software to connect all these business systems is usually pretty brittle and janky, and there's been lots of good startups founded to solve this problem. I think there's still a lot more room for improvement and likely LLMs will improve, like we'll probably be able to create better and better blue. So all sorts of software systems can talk to each other. And so again, very broad idea. But yeah, I think we'll see a lot of very successful companies where that's the kernel of the idea they start with.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  37. “Totally have, right? So these aren't like, oh, we've never invested in these before. It's more of like, hey, it'd be cool if we saw more applications along these lines. It would be nice because it currently feels a little bit under. There could be more startups working on this”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  38. “If more people applied to YC with open source ideas, I think we'd be pretty excited about that. And that might maybe fatters didn't realize that would be something we want to fund. Same with space companies. Yeah, we've had a lot of success with space companies. Several of the folks that are actually going to space right now that aren't SpaceX are YC companies. And so I think sometimes founders feel like those ideas are too bold and ambitious. But no, I love if more people applied with space companies. And so think about it that way where we're just trying to put out, we're trying to plant seeds of idea spaces that perhaps someone subconsciously filtered out as what might be a good startup idea. And, you know. Hopefully that creates a new set of startup ideation for the person.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  39. “Yeah, and so we put out the request for startups just to inspire people to maybe apply with ideas that aren't the ones that we always see. It's not like prescriptive, like we will only fund ideas on those lists. It is not that at all. It's just sort of, remember what I talked about earlier with information diet? We're trying to mix up some of the information diet about what kind of ideas people might be contemplating they are currently. And so a couple of the ones that we put out there, one of them I made one about ERPs, which is enterprise resource planning software. And I did that because I get so few applications on that. And they're usually pretty good. And I just would love to see more people look at that and learn about.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  40. “But what usually happens is you pivot to a good idea or you start with a good idea that you care about and customers you care about and you launch it and the better the product does, the more obsessed you get with your own company. Like I think in the case of Stripe, I don't want to tell Patrick's story for him, but I recall him saying at some point, he wasn't as sure that Stripe was going to work until they were like a year or two in. And then once it started working, then he really believed in it. But it wasn't like he woke up one day and like, Stripe is the thing. It's going to be. I think you build conviction and you have this network effect virtual cycle where you get more conviction. The more customers reflect back to you and data reflects back to you that you're on the right track”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  41. “Well, I think it's internally they're convinced. I'm not sure it's external, but and this is the big but, no one has this at the early stages when they don't have a good idea and they don't have customers and like it's objectively not working. And so again, I know a lot of founders are like, well, I don't feel that way. Oh no, maybe I'm an imposter and I shouldn't do a startup. Well, of course you don't feel that way if you haven't talked to any customers and haven't built a product.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  42. “Even though objectively there's all this data coming in, this isn't working, this is bad. My employees want to quit, my executives want to quit, you know, whatever it is, somewhere deep down in there, like, oh yeah, I'm going to make this work. This company is going to be big. And they just believe. And it's almost like that internal gravitational force inside of them is so large. It kind of warps the world to bend to that will. And people start to believe it because they believe it so much and they convince their employees to believe it and they convince everyone around them that this is going to happen for them. And so again, this is not a personality trait. I'm arguing this is like, um... Core belief”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  43. “The thing that I would argue folks that build really big companies have in common is they just really want it and they really believe in themselves and they really believe they can make it work. And they're somehow deep in their internal psyche. There's something that's like, I'm the one. And I won't accept this not working.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  44. “I don't think personality types matter as much. I've seen very quiet people, very extroverted people, very, you know, you name it. I've seen all sorts of personality types. So for me personally, I don't think that there's a right, or I don't think there's a personality type that people should copy and be like, I need to be like this person. I need to be like Steve Jobs. I need to be like Elon. I don't really believe in that because there's just so much variation. Like Tony from DoorDash is so different. Than a lot of folks, and Rajel, who is so different, and grant from whatnot, these are all very, very different people. Patrick is a different kind of person. Ryan from Flexport, like these are just very different personality types.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  45. “Oh, surely not. It's just you got to do it. Like, if you want your startup to work, this is just what you got to do, you know, comes with the territory.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  46. “Yeah, I was an early stripe customer at my startup. And yeah, Patrick would like, we used Google Talk at the time. Patrick would be sending me messages on a weekly basis, just like checking in. And so it's funny how successful these folks get. But yeah, Patrick was very hands-on with all of his customers and it was extremely available. Like I can say that because I was one of them. Yeah.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  47. “Smiling, being like charming guys. And then we're like, oh, that's cool. Okay, well, like, can we roll out the website now? And they basically would kind of not go away until you finish the implementation of Stripe. And like, again, it was actually helpful because they were doing all this White Glove service to get it implemented. That was very effective. And I think the takeaway from that story is even when you get a yes, you're not actually done with sales. You have to finish the last mile to get the thing implemented. And they weren't very good at that.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  48. “The Calls and Install is what often happens with customers is that they say, yes, I want to buy your product. And then they do not implement it. They just go quiet. They're like, there's no implementation. And this is very bad if you're selling software to someone. If they never implement it, they're going to churn and you're not, you know, you basically failed on the one yard line. And so they kind of developed this tactic to be like, oh, well, you know, I'm at the neighborhood, you know, I'll drop by your office to help you implement Stripe and kind of just like create, again, it was a little awkward like we talked about earlier, but you would be like, yeah, I'm in the neighborhood. Like, how about I drive by? And then they would show up and they'd be like, cool, cool. Can you like pull up your text editor? Oh, yeah, cool. All right. Hey, can I drive? Can I have the keyboard? And they would just sort of like install Stripe into their customer's website, you know.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  49. “Their calendars are filled with people that were trying to implement the first open source version of Postdog or so excited about it and people on Hacker News were excited about it. And they had this huge influx of people that were excited that Post Hog exists and had lots of feedback and web reports. Like it wasn't always positive, but they never lacked for people that wanted to talk to them once they launched that, which was very helpful.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source

  50. “Well, again, some of the companies we talked about, I mean, for Brex, we're just talking to other people in their batch, and that worked extremely well. Same with Retool is they just sold it inside of the YC network. I think with Zip, they were just beasts at getting companies on calls with them to ask them about procurement. And I think they had way more than 20% of their time. Like when you looked at their calendars, oh man. They were doing, they were talking to customers a lot to build their first product and kind of pre selling it before they built it. Same with postdoc. I guess that's a different go-to-market. They launched this open source thing to start with. And it was.”

    2024-04-18 · Lenny's Podcast · Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · IDENTIFIED FROM THE TRANSCRIPT · source