YouSaid · the spoken record

Dalton Caldwell

lines on the record
98
first
2024-04-18
most recent
2024-04-18
sittings or episodes
1
sources
podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

  1. “Yeah. And again, it depends on the idea space you're working on, some are more, some are less. So, yeah, I just, it should be a fair amount of time and nothing substitutes for an actual conversation versus just staring at analytics dashboards.”

    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. “Yeah, I don't know if I know a good number. I think it's look at your calendar and there should be, you know, 20 or 30% of your time that the calendar says something like customer. Meeting customer call, like meeting with Foo, meeting with this person. And when the calendar is not that or it's all, you know, again, what you're actually doing is just buying ads to try to validate your idea. I don't think that's talking to customers. I think that's something else.”

    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. “And I think you just gotta get past that. You know, you just got to start doing it until it doesn't feel bad anymore. Think about how stupid the Airbnb fatters must have felt they were like, hey, you should rent out your house and I'm gonna come and sleep in your house. And here's an hairbed. Like the whole thing is a little awkward, right? So you got power through the awkwardness of talking to people. And once you start doing it, it's actually kind of fun. And so once you get used to overcoming this awkwardness, I think people do much better at talking to customers.”

    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. “Up to go out in the physical world, get people to meet with you, get them to take you seriously, show them a product you're building. And so again, it'd be very tactical here. You can do a self-assessment. In the past month, how many in-person physical meetings have I had with potential customers? Maybe you've done a lot. I don't know, listener, maybe you have, but it's shocking how many companies I talk to, they're like, well. Focused on raising our precede round before we talk to customers, like things like that. And again, I think the core core thing going on is just social anxiety. And like looking stupid”

    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, I think when I talk to aspiring fanners about this a lot, they're like, yeah, yeah, I talk to customers. We get it. Cool. And they're like, cool, whoa, how many customers have you talked to? And they're like, well, and they get really quiet. And so I think this is one of those things like, hey, you should have a healthy diet and exercise every day or whatever where people know it. And that doesn't mean they do it. And so I think to start with, you have to get out in the world and talk to people in person. And you can't just hide behind your keyboard and call that talking to customers, right? And I think a lot of folks, their inclinations are to like, you know, build a landing page and buy some Instagram ads and try to get people to sign up for something. And again, maybe that's something, but I think a lot of the reason people do that is they're just shy and they don't want to put themselves out there because it's a little awkward to go talk to people. And you kind of have to set yourself.”

    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. “I would argue that We define it. Is the company had a near death experience where it was going poorly and the founders seriously wondered if it was all going to be over 100% of the time people go through that? You know, where the founders like, yeah, I guess we're done. I guess we should pack it in. And at least you feel that way at some point in your startup journey. I mean, everyone goes through that. And again, there's gradiations. People that actually truly got down to very, very hard situations, it's still a high percentage, like maybe 50%. I mean, you can ask founders. There's a lot of founders that Come this close to it albeit over and through sheer will kind of just keep it going, 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

  7. “You're out of ideas. You're like, I'm just done. Like, if you know in your heart that you're done, you don't have to keep going through the motions. No one benefits from”

    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. “And as long as you don't accept that that's going to happen, there's usually a lot more moves you can try to save the company. Maybe it's to get profitable. Maybe it's to do some other zany thing. Maybe it's, you know, to launch a new product. And so it's pretty rare, I would argue, that the cause of death is that they had lots of firepower and they were feeling really positive and they just ran out of money. That's actually more rare than founders think. It's much more common that they still have some money left. I'm not saying a lot, but some money. And they're just like, yeah, I'm done. I'm out of ideas. I don't want to do this anymore. And again, fair enough, you know. But you get what I'm saying? I think founders are afraid that they're going to run out of money and that's why they're going to shut down. And it's way more common that they like their idea doesn't work and they have a big fight with their co-founder and then they can't agree on what to work on. And then they just like are like, I don't want to do this anymore. And they shut down. That is the most common cause of death is something that sounds 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

  9. “Completely agree with what Gustav said, but to look at this from a different frame, I think as it the founders lose hope And when you and your heart is like, yeah, we're failing. Like once I can see it when I'm meeting with the founder when they've resigned themselves that they're failing versus when like we got one more move in us. We got one more try. Like you can see in their eyes when they feel like there's more ideas or there's some blast itch Hail Mary thing. It doesn't always work, but it's almost like you have to not accept that you're going to.”

    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. “Think if you just care a lot about your customers and you care a lot about the product, your instincts are pretty good on what to spend time on. And so, for example, spending tons and tons of time like. Hanging out with investors and networking is probably not the thing that I would be cutting. You know what I'm saying? It's what we talked about earlier. If you really love what you're doing, no one needs to tell you how to reprioritize your time. Your intuition will be correct on what you should be spending all your time on, which is being obsessed with 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

  11. “You raise all this money, you got to spend it. You got to show you're serious about growth and building a world class organization, whatever, stuff like that. And so you end up with super nice people with super shiny resumes from big tech companies. Oh, wow, they did this amazing thing at Google. And then you hire them and then you wake up one day and you're like, oh, wow, everything went wrong. Really, anyone's fault? It's just that you took your eye off the ball, and this is what happens First time founder”

    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. “I don't remember the specific office hours, but I understand the question, and of course, remember Lenny. I think that the advice that he's referencing here is just how important it is to not over-delegate and for the founders to stay close to things, as well as watch out for the trap of hiring super senior people with fancy resumes really early in a startup. I think that's what he's referencing there. And again, this is definitely one of those very basic things that we find ourselves repeating a lot where they're like, yeah, yeah, I get it. Like, don't over-delegate. We get it, Adults. And then like two years later, they're like, wow, we over-delegated. We need to go clean that up. So that is probably the best product advice. And the folks that are really great at product, the founders that are always deeply in the weeds on product and still care a lot and are still talking to customers no matter how late stage it gets again i'm sure you experienced this in airbnb culture but you know you can't delegate”

    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. “Yeah, or you're asking them to believe a crazy leap of faith that, again, they could say, well, it's theoretically possible you'll be able to sell more than Funko Pops. And I understand that that is your pitch. But I have other opportunities that are less risky. You know what I'm saying? Like it's not because a lot of founders make the argument that the TAM is big and you can say, wow, that's a really interesting argument. And I have no, I'm not going to argue with you about it, but no, I'm not going to about it. And so again, it's hard to get someone to engage in a debate about TAM, even if you have. Know, even if you have some proof points, ultimately, a lot of investors just don't like that risk. Fair enough.”

    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. “And I'm not saying it's not important. I just, it's not, and the things I'm worried about is like, hey, how do you get users? Hey, how do you grow? Things like that. Like, are you making something people want? Those are the things I'm really worried about as opposed to, ooh, I ran an Excel model and I'm worried this might not be a big enough TAM. That's not at the top of my list.”

    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. “Not saying that having a large market someday doesn't matter. Of course it does eventually, but trying to be super pedantic about market size when it's like a preseed company. Is not, you know, it's just not something I put a lot of thought in. Again, whatnot, oh, what's the TAM of the collectible Funko Pop industry? I don't know. I don't think it's that big, man. I don't know if you do that house. That's when you invested, but things are pretty small, but I wasn't worried about it. That was like the last thing I was worried 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

  16. “Think it really depends on what stage you're investing at. And it's absolutely critical the later stage you get, right? If you're going to invest in a very cligh valuation, it is really important. The earlier you go, the less it matters. And some of the most phenomenally good startups, if you were really panantic about it, the TAM would be like tiny. Like the TAM of Uber would be like nothing, right? The TAM of Airbnb would have been nothing. The TAM of, I funded RazorPay, which is, I think, the largest payment processor in India. And the TAM of that was tiny because no one was using credit cards in 2015 in India. So you had to believe that the size of the credit card industry in India was like 100x. Well, guess what happened? What I'm saying? And so”

    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. “Yeah, because again, and if you ask someone, well, put yourself in investor shoes, wouldn't you be making decisions the same way? Usually founders are like, yeah. If you do that exercise, a lot of this starts to make way more sense.”

    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. “And that's actually why they're saying no versus this you did, you know, oh, you had a bad Zoom setup or something, you know, oh, we didn't like what color your shirt was. We said no. I don't think that's how this actually 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

  19. “And I often think that founders think that there's some secret truth that's being held from them on why someone says no or like they're, you know, like they want more feedback. I need feedback. It's like, wow, the feedback is we didn't want to invest. And it really is just that. And so I think if you put yourself in the shoes of an investor of like, hey, I only can do a few of these a year. I have very limited budget. They're really just trying to pick the things that they're either personally most excited about or things that they think can be truly phenomenally big in some way. Or, you know, again, I know you do investments too. So it's. It's that you only get so many shots as an investor. And so anything that doesn't seem like this is the one, this is the one I want to do is a no.”

    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. “Been my best advice here is for founders to put themselves in the shoes of investors and just imagine what their life is like and how if you are in their shoes you would make decisions. And so given this framework, a lot of investors just don't make that many investments. And as for what we talked about earlier, life is short. And so there's lots of things that an investor in their hearts thinks is like pretty good. And they're like, oh, like, I like this person and I like their pitch. I only am going to do a few investments. And so even though I really like a lot of Malthus, I'm going to say no.”

    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. “Yeah. And all the Foursquare clones, if they didn't pivot out of doing what they're doing, wouldn't have worked. So anyway, that type heart bit is just something that's super appealing and a lot of people do it. And you can kind of get validation. And that's why is it Tarput is it draws you land and you get stuck because it seems like it's like a good idea and you get all this positive feedback.”

    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. “And so you can validate it. Like, part of being a true tarpit is that you can get good initial validation Do you get what I mean? And so, anyway, and honestly, I worked on TARP and ideas myself as a founder, which was a music discovery. This is something I did in my first startup. Music startups are hard. And trying to be like, oh, we're going to fix music discovery was classic things where you could get lots of positive feedback and even get users to work on those things. But there are aspects of it that make it a very hard idea. So does that make sense?”

    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. “you have a really good set of arguments that it's a really good startup idea and that's different than a bad startup idea you get what i'm trying to say a bad startup idea is like i don't know something that is obviously bad or something where you just can't get any positive uh feedback on but some of the the most common tarpit would be something like building um like an app to coordinate with your friends to decide where to go out at night or where to meet up with people which is it which is a really it's coming from a good place like it's a good idea if you ask your friends hey would you like an app for us to coordinate to hang out more so we can be friends that are like yeah i would love that like you'll you'll get you'll get all this positive feedback from the world and man people have been starting that startup since like the 90s”

    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. “People that are familiar with this terminology, for most, sometimes they get defensive and don't get what we were saying. So let me, by definition, it is only a tar pit if it seems like it's not. If it's just a regular idea that is hard, that is not a tar pit. The weird aspect of what we call a tarpit idea is an idea that a lot of people come up with and then it seems like an unsolved problem and you get lots of positive feedback for, 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

  25. “Try to mix up what your information diet is or what areas of expertise you have and mine that well versus just having all the same thoughts and everybody else. And so again, let me give you one more example. A few years ago, Startups around trucking were super new and fresh because no one was doing them and they worked really well. And then it became completely conventional wisdom to do like trucking related startups. You'll see things that become fashionable really quickly because someone found success in this unfashionable space and then it becomes fashionable.”

    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. “Does it seem surprising then that you would all end up with similar startup ideas or similar philosophies on what makes a good startup idea? Of course you are. So this is the metaphor on cities, is that if you just are following the same principles and have the same information flow into your brain, you're going to come up with the same ideas as everybody else. And so the prompt here is to try to go more off the beaten path, either from your personal experience, like in the case of Brex and Retool or whatnot. There was no one else trying to build marketplaces for Funko Pops. Go deeper in your own personal interest or experience to find something that just Your exact peer wouldn't come up with exactly this. Wonky procurement software. That was not an idea that we saw much of. And so, again, the prompt to people”

    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. “Yeah, I think maybe this curtains into what we see from applications and interviews, which is. From where I sit, seeing everything people apply to YC with and what they interview with and whatnot, people all kind of have the same idea. Like basically, imagine this. Imagine your information consumption where you're listening to the same podcast, wink, wink, you're reading the same people on Twitter, you're reading the same blog post. Basically, you have the same information diet of all these other founders and you're friends with all the same people.”

    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. “Course, like, sorry, yeah, we got to give Lou the shout out. Lou did an amazing job. I just didn't know Lou as well before he did YC, but you're right. We got to give Lou the credit.”

    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. “Yeah, I mean, I can't promise that works for everyone, but again, in the very bespoke situation with Rajul, it worked really well because he actually knew exactly once he locked in on that prompt, oh, man, he ran a masterclass. You know, like they did it. They did an A plus job. It was really good”

    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. “Had a lot of confidence in his competence on running a business and executing fast and just having great instincts. Like he really knows the fundamentals. And the problem was they weren't as clear on what market to go into is still with me. And so I actually suggested to do something in their casing, and this is very bespoke. But my suggestion was to start by looking at what companies are publicly traded and or owned by private equity that are large and that also are hated by their customers. And to try to intentionally find where there's a knowable big market with an incumbent combined with the software is horrible. And they kind of did that. Like they basically found out about all this procurement software and what the state of the art was. And that was the prompt. Again, maybe he told you this. That was basically the process.”

    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. “Yeah, I think in the example of the Zip founders, they were both such great experts. And, you know, I knew Rajul really well. He actually worked with me at YC as a visiting partner. And so I was really close to Rajul and he done this marketplace called Flight Car when he was younger, which was raise a series B. It didn't work out, but it was a really cool 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

  32. “Inventions, like they had a bunch of zany ideas on growth and they didn't run out of them. And so I think when you're still gas in the tank on an idea, that might be a reason to state the course. And when literally the founder is like, yeah, I don't know. I guess. Maybe we should pay influencers or something. When that's the kind of ideas they're coming up with, that might be a better scientific pivot.”

    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. “Again, this is one of those where I like to get very bespoke, nuanced advice on a case-by-case basis to the folks in YC. But again, just to give you a preview of how I would think about it, I would look at how many more ideas the founder has on how to make it grow. Like if it's not going well. You're out of ideas, that is usually a good time to pivot. But when there's a, you know, you have like half a dozen or a dozen really good growth ideas that you haven't tried yet, try them. Like, hey, give it a shot. Again, in the Airbnb story, right? They tried all sorts of stuff, including cereal and.”

    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. “Know anything about how analytics worked, but because they were grinding for multiple years and became experts on these things is a side effect of their earlier ideas, they ended up with really good unique insights.”

    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. “In the example of segment, which is obviously a really big successful company, they started with something to tell your professor you were confused in class. It was like software that they sold at universities. And then they ended up pivoting to something kind of like a mixed panel competitor after like two years. And it's because they didn't, they learned about how analytics works running their first idea. And then no one wanted to adopt their mixed panel competitor. And so they were like, we should make this JavaScript thing that you embed on your website that can send events to multiple endpoints at the same time so that way people would be willing to try our mix panel competitor side by side with mixed panel to show that it's better and then they were like oh yeah no one actually wants that they just want this javascript to send events to different locations and so there's no way those founders could have started with the final idea you get what i mean there was no universe where they would have made up the idea for segment because they should”

    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. “In the case of post hog pivoting into their idea, they knew a lot about analytics and had strong opinions about it. And so it was much closer than what the original idea is. In the case of zip, Rajul knows a lot about a lot of things. He knew a lot about the crazy procurement process at Airbnb because he worked there. And so it was kind of like, I couldn't pivot as like going home, you know? It's warmer. It's closer to something that you, and it never occurred to you that this thing you know all about would be a good idea. Or maybe you consciously, you're like, I don't want to work on this because I'm burnt out on it. Like sometimes you have to. Someone someone has to get over this barrier they have on why they don't want to work on a certain idea.”

    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. “Usually A successful pivot gets warmer instead of colder from what you're an expert at and somehow builds on what you learned on the prior idea. And so in the case of Brexit, it was let's work on a fintech company in Brazil when they were younger. And so I'm like, you need to work more on the thing you know all about and not the thing you know nothing about. And that was what worked for them. In the case of Ritual, it was the same thing. They built similar internal tools, both at their internships as well as for cashew. They had all these dashboards they built to operate their Venmo competitor. And so they knew a lot 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

  38. “That was really high tech. They wanted to do a really high tech startup. And so they're like, we're going to build a new VR headset. And they were good programmers, but they just didn't know anything about optics or the things you might want to be an expert in to build a headset.”

    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. “Called cashew, which was this P2P for the P2P Venmo in the UK, and it was going really poorly also and not growing. And so if you just took the snapshot in time in the middle of the batch of like, who is definitely not doing well, it would clearly have been this Beyond Company and this cashew company. And so to catch the chase, Beyond changed their idea and got really excited about it and renamed to Brex. And this was Brex, which is like a deca corn. And Cashew changed their idea and renamed to something called Retool. And so out of my 35 companies, the ones that objectively seem the worst in terms of like, everything is going bad were by far in retrospect the most successful companies in that group.”

    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. “Give up basically. And if you would have asked people in the batch. What the worst company was. I think they would have said this one. Yeah, not because like they were like bad people, but it was just like the founders themselves seemed like despondent about how it was going. And then funnily enough, this isn't the story too. There was another startup also in my group”

    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. “That definitely happened. And I think the story is the story of the winter 17 badge. And in the winter 17 batch, I funded something like, I don't know, 35, 40 companies in my group. So we subset them into groups. So it wasn't like a lot of companies. And I knew all of them really well. And founders can't help but compare themselves with other founders all the time about who's doing well and who's not doing well. And there was this one company in my group this batch was called Beyond. That was their name at the time. And it was like a VR headset thing from these Stanford dropouts. And they basically showed up to group office hours and were just ashamed. And they're like, our idea is horrible. You know, we might want to shut our company down. This is like really embarrassing. I had to like beg them to not.”

    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. “It's really going poorly, if you're having a really bad time, it's no big deal. No one will remember that you shut down your company probably in 10 years or 20 years. Like time, as long as you have integrity, as long as you're an honest person, as long as you handle yourself well through good times and bad, people will remember you fondly. And it's better. We have such a short life. There's only so many years we get to have our careers doing something that makes you miserable. And the only reason you're doing it is to avoid losing face. And you know when your heart is not going to work, I don't know. That seems like a pretty big opportunity cost on literally 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

  43. “And they liked working with each other and they liked the first hosts that they met. And they knew all their names. You know what I'm saying? Like they were actually, they loved their startup, even though it was going bad. And so that's kind of to me a signal to keep going is that you really, really love what you're doing and the people you're doing it with and you love your customers and you love the problem versus where you're just like, yeah, I could care less about any of those things. I'm just having a bad time. Harder to be encouraging in that situation, you know. And this is a fixable situation. You can make it more like the thing you love, can't 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

  44. “Think this is a nuanced question, and it's hard for me to say something on a podcast that will actually be useful to people, but here's a couple of thoughts. One, are you still having fun? Do you still enjoy doing what you're doing? Do you enjoy spending time with your co-founders? Is this actually a fun thing you're doing? And if the answer is yes, I would tend to lean on the keep going. And then if it's more of, wow, this is actually profoundly affecting me in negative way and my relationships with people in my life and my team, you know, I don't really want to work with my co-founder anymore and things like that, then I would lean on the probably don't do it anymore. Something that a lot of the folks that turn it around have in common is they actually do love their customers and they love their product. And again, in the Airbnb story, again, you know it really well, but they really liked Airbnb.”

    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. “You know, intention to keep going, even when the world tells you it's not working and you feel completely defeated. And you likely have to go through this many times and have these near-death experiences. And then you get lucky and then you look like an overnight success. right and so that's that's that is the theme that is a summary and i provide you know lots of data lots of stories there but this is one of those things that the the longer i had this job the more i really really believe this is true”

    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. “Way to summarize that is if you look at all the startup stories that we have at YC and all the companies we funded over all the years. The underlying theme. That rationally, the founder should have given up at some point. And so, again, let's talk about Airbnb. Obviously, something you know a lot about, they probably should have shut down like three or four times before they got into YC. It objectively wasn't working. They were basically ruining their lives. They were disappointing their parents. Everything was wrong. And it was a purely irrational act for the founders of Airbnb to keep working on their goofy story. And so, and again, that's just one story. If you Across the portfolio of YC and non YC companies, there has to be this irrational.”

    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. “Even if you're the best in the world, being coached and being reminded of the fundamentals and basics is what puts you in the right mindset. And that you already know everything, right? You're at the top of your game if you make it to the elite levels of being a startup founder or basically doing anything that's really hard psychologically. And so, yeah. One of my mantras is just don't die Just keep your startup going Just keep going. And I say that over and over again. And honestly, that is often what people tell me is the most impactful thing I say. It's not that I said some ninja 5D chess move that they never would have thought of before. It's just the constant affirmation. Continuing to keep going and doing high quality reps is the game”

    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. “Ever seen Like NBA basketball or college basketball where they have the coach mic up and it shows what they're actually saving in the huddle. Listen to what they actually are saying? They're like, okay, we need to really focus and get the ball and win this game. Like if you actually listen to what the greatest, smartest, most successful athletes are talking about, like if you listen to what Tiger Woods is saying to his caddy, All sounds like pretty mundane stuff. They're not, it's not like what Tiger Woods is talking about with his caddy is some, you know, impossible to decipher jargon. And so like, yeah, you really need to keep your head down on this one. Like that. And I think the reason. Is true is 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