Going Solo Should Be the Rule, Not the Exception | Flo Crivello, Lindy

19:58Lindy:so you know we released and everybody was going remote and everything was going well and we had like the windy hour back when everybody was going remote it was like the growth kills were really something and the engagement kills were really something and then when everybody returned to the office like the growth skills were really something again except in the other direction. And so and nothing we did moved to the needle. The market had just moved on. That was tragic. You have no idea. The pain you go through of like just banging your head against the wall and nothing works. I forgot who it is who told me if you think of it as a two by two where it's like things are hard or things are easy and you're like a persistent founder or a non-persistent founder the hardest quadrant to be in is a persistent founder when things are hard.

20:45Lindy:Because the moment things started being hard, we had like 20 competitors who gave up immediately. We stuck with it for like a good 12 months, which I think was a big mistake. But yeah, at some point it was just obvious of like, hey, we stuck with it. We tried everything we could. Nothing's worked. Nothing's moved the needle. Let's just call it guys. And it coincided with, so we were like a virtual office. We built a meeting recorder as part of the virtual office. And this coincided with the GPT-3 API coming out. And I had been following AI for a very long time. Like since, hey, I'm on the record since GPT-2 for saying, like this is the first step to LGGI, which at the time GPT-2 could do nothing.

21:29Lindy:And GPT-3 API comes out and I'm like, oh my God, this is awesome. Like, can we, okay, hey, like now everyone does this, but at the time, like it was very new. Like, hey, let's build like a thing that summarizes your meetings. And then salespeople come to me and are like, like, Flo, you have no idea. We spend so much time updating our Salesforce every day. Can you also make this thing update our Salesforce for us? And I'm like, yeah, probably. At the time, people would call it feature extraction. So we can extract. What do you update to Salesforce with? Like the next step, whether there's a champion, the number of seats they're going to buy.

21:59Lindy:So I guess we can extract that using the language model. Even then, it barely worked. The hallucination rate was off the charts. So we do that. And then they're like, ah, actually, we're doing a lot more fields. It'd be neat if you just give us an admin UI. so we do that. Ah, actually, you know, we're going to switch to HubSpot so now we need to like do that. And basically, little by little, we make this thing more and more general so it can update any fields on any CRM. And then at some point it clicked and it was before ChatGPT but it clicked around like October 2022 and we were like, oh my God, like LLMs can do stuff.

22:32Lindy:We're like, oh, why don't we just have the LLM make the entire API call for us? Like, and it worked. Like, oh my God, like this is not LLMs. At the time, I don't know if you recall, like now everyone's talking about agents. At the time, no one was talking about agents. People were talking about generative AI. People don't talk about generative AI anymore. And at the time, we were saying, look, generating text and generating images is fun and cute, but the GDP is not made of copywriters and illustrators. It's made of work. So agents are where it's at. And then Langchain came out, and I remember meeting Harrison very early.

23:02I made him, in hindsight, ridiculous,

23:04Lindy:like we hire you. I was like, hey, why don't you? He had not incorporated yet to my knowledge. He was like, oh, why don't you join us? We'll give you a bunch of money. He has like a signing bonus at Will Call and Equihire. I think he still was like at his previous job. And yeah, I mean, so comes Christmas, you know, I was like on that Christmas break and it was just obvious like the team was like sucked into this idea. We're very excited about it. And the TeamFlow thing was like obviously not working. And so we just decided to like pivot completely to Lindy.

23:32Flo Crivello:How many people were on the team when you made that transition from TeamFlow to that version of Lindy? About 45. two-thirds of which we let go of once we decided to make the transition. Got it. And I think that a lot of companies have to go through these types of moments to actually get to the thing that works. But I don't think that you actually hear that many people talk about what that actually entails and sort of the challenges around it and how to judge who's ready to make the transition and also how to make the transition from that, right? because that's a pretty big jump. It requires, you know, cutting a lot of headcount.

24:14Flo Crivello:Some people who might have been doing really great work at the last thing, but it doesn't make sense for them to be sort of the early days of a new company. This is effectively a new company. Can you share any sort of things that you've learned from that or things that maybe people should know about when they're in that situation? Like one thing I've heard and, you know, like I've experienced personally is that oftentimes people don't make enough, like a large enough of a cut. And that's like, that's extremely devastating for everybody involved. Yes. But I, so they end up usually having to do two rounds of it and that's like really bad.

24:48Flo Crivello:But I'm curious what other things like you've learned from it. So much.

24:53Lindy:By the way, I think this right here is like the right question and like, you know, how do you know when to make the move? And you're right, like a lot of startups do go through that extraordinarily painful chapter which kills companies all the time. And I think it's Marc Andreessen who said the essence of entrepreneurial judgment is the ability to tell the situation that's broken that work and iteration will see it through versus one that's broken and it requires a radical change. And I agree with that. I learned a bunch of lessons. Number one, make the change faster. You know and you feel it when it's going to work.

25:29Lindy:So make the change faster. Two, cut deep. we didn't get deep enough. You know, we went from 45 to like 12 or 15. And that's too big. Yeah. You know, I think the ultimate, like the great, the best team size when you're like zero to one is like three to five. You know, you just need a bunch of like really good builders. So both Elad Gill and Naval Ravikant give this advice. They put it in different terms. I like Naval's characterization of it. He says like building a startup is kind of like surveying a huge, like infinitely large because the search space is literally infinite, an infinitely dense jungle.

26:08Lindy:So you're surveying it from a helicopter. And at some point, you see a spot in the jungle that you like and you land and you start to clear off the brush and you see what's going on here. If you don't find something you like, you don't stay in the jungle. You climb back in the helicopter and you survey again. And the thing is only so many people fit in the helicopter. So it's really hard to climb back if there's like 50 of you lost in the jungle. Make a big change. don't overly incur on like whatever previous thing you were doing and i think we did that right like we moved from like a virtual office to like an ai agent completely different yeah i'd say those are

26:40Flo Crivello:the biggest lessons what was the uh if you if you you said uh mark andreessen had or um naval had that one about the jungle and the helicopter and then you also mentioned something from um it wasn't it wasn't mark andreessen a lot a lot of it is the same thing except he doesn't

26:57Lindy:said the jungle thing. It just says it. It's like a mega big change. I think another thing I learned actually, and I tweeted it at the time, is when I made that pivot, after like two years of chewing glass and staring at the abyss, I felt so burnt out. And like one factor that was weighing on my mind was like, I don't know if I can pivot right now. I need to chill out for like six months at least. I need to chill out. I can't do this. I had just been grinding really, really, really hard for more than two years. And it's the worst type of grinding where it's like it's Sisyphean. It's like you're just pushing a bulldog uphill and then nothing happens.

27:33Lindy:It's like you've got to do it all the time. And I was like, I see an opportunity, but I don't know if I have it in me to pursue it right now. And I was like, fuck it, I'll just give it another go. I can do it. And then the thing that took me by surprise is just how quickly my energy came back. And I tweeted that saying, which is the cure to burn out is not rest, it's momentum. It comes back immediately the moment you have momentum and the moment you're excited again about what you're working on. So insofar as that's a factor for any other founder out there, I would say you don't need as much rest as you think you do.

28:06Lindy:You just have momentum.

28:07Flo Crivello:I feel like we were talking about a lot there. One thing that I really liked from one of his blog posts a long time ago is this idea of startups and miracles. This idea that startups that require multiple miracles are usually bad startups, but startups that, you know, the best types of startups do require like one thing to go really well. Uh, I'm curious sort of how you've thought about, you know, as you've, as you've sort of evolved and like developed Lindy over time, um, how you've thought about things like that, or also another one that he has is like this idea of like no bank shots, essentially like you don't want to try and bounce off the side of the pool table.

28:46Flo Crivello:You just want to go straight to the hole. Um, I'm curious, like what models or like philosophies you've had, um, as you've developed kind of what Lindy is over time.

28:56Lindy:Yeah, I very much agree with these philosophies. Like one analogy I use increasingly to describe startup building is that of a gold rush and a gold-seeking expedition. And I think there's a lot of insights you can get from the analogies. It's sort of like the gift that keeps on giving. Namely, one, there are two very distinct phases in building a startup. And the first one is like you're looking for gold. The first one is like prospecting, like looking for gold, like the right ground. And the second one is like building and operating a mine. Have you seen the movie There Will Be Blood?

29:31Flo Crivello:Yeah, of course. You know, in the beginning

29:33Lindy:it's just him, right? It's just him like lust and like looking and at some point he sort of like miraculously stumbles upon like an ocean of oil and then he builds a business. It's like he builds a town.

29:41Flo Crivello:He nearly dies in the process. Yes.

29:44Lindy:And so he builds a business, he builds a town and all of that stuff. And so, and those are qualitatively distinct activities. And this is why I gave the advice earlier of like you've got to cut very deep because like you've got to be alone. Like looking for gold is not a 20-people job. It's a one-person job, really. It's a founder's job. No one else can do it but you. And the problem is like operating a mine is a full-time job. It's a lot of work to operate a business. And if you're busy operating the business all day, you have no time to prospect for gold. So I would actually say that's another piece of advice I would give is if you're in that situation where you're like, something feels really, really off.

30:22Lindy:And I think we're like digging the wrong ground, the wrong ground here. There's another way this analogy keeps on giving. It's like, if you're digging the wrong ground, if there is no gold here, it doesn't matter how good of a digger you are. You're wasting your time to not dig, you know? So if you're in that situation where you're like, hey, I think we're digging the wrong ground, but I have no time to prospect for other grounds because I'm busy managing this mine here. My advice, and it's so hard, but it's to neglect the mine. And it's so hard because of course, you can't neglect the mine. It's like there's all these people asking for your time, all these amazing things.

30:52Lindy:Like, well, it doesn't matter. You know, they're digging where there is no gold. So like, it actually doesn't matter. You've got to clear your calendar and you've got to neglect people. And then they're going to like twiddle their thumbs and be like, this company is so in Spanish, we literally have no idea what to do. And the founder is a stupid, incompetent guy and we have no idea what he's doing all day. And that's perfectly fine. That's you doing your job. The other things you can take from that gold-seeking expedition thing, Elad talks about this. He says like, when it works, it works quickly.

31:19Lindy:and that's not always the case. Sometimes you've got the open AI. There's always like a thousand counter examples, but like by and large, I think the story of segment here is telling, or like hugging face is telling. There's so many stories like that where it's like, hey, we work on this thing and we grind for like two or three years and nothing happens. And if you count progress in lines of code, which you shouldn't, but if you count it in lines of code, you're like, hey, we wrote like 50 ,000 lines of code on this thing and nothing happened. We wrote a thousand on this and it blew up. Like the segment guys, they released this library, like analytics.js, just as a weird little thing.

31:54Lindy:It's like, this can't work. This is a toy. Like, why would this work? Blew up on Hacker News, immediately became a thing. You know? There's so many examples of that. Like Slack worked really quickly. Hugging Face, I think they were working on like a mobile app, like an AI friend, AI girlfriend kind of thing. And then they're just like, oh, like how about GitHub for models? and like just CTO just coded it in the weekend and released it. And then the rest is history. It just immediately took off. So it just works quickly. And so I think it's the same. Like if you found ground that's got gold, it's like, or like that's got oil, like it's like seeping off the ground.

32:30Lindy:Like if you study like the gold seeking expeditions, like the gold rush in the 1850s in California, it's literally like you can basically see the gold nuggets on the floor. It doesn't take a genius, you know? I think those are some of the things I've learned about this.

32:43Flo Crivello:It's interesting the idea of having people essentially having to sit around and like twiddle their thumbs while the founder is trying to figure out what the business actually is. Because that's one of the biggest challenges, right? When you don't cut deeply enough before trying to get to that next place where you figure out what the new business is. Because then you have them just sort of sitting around and thinking the founder is incompetent when they're doing what the founder should be doing, which is figuring out what's next. And then you also sometimes have this pressure as the founder to not just figure out the thing, but also give answers to the people about what the thing is before you need to.

33:20Flo Crivello:And I think in some ways this is also true for co-founders. Like when co-founding goes poorly, you've got this situation where if you're sort of the, you know, it's not always this, but there's sometimes the person who's the sales sort of person and the person who's more of the product builder type. and even though they might both be technical, there's this aspect of like the sales type person needs to have an answer to the product type person sometimes. And it creates this weird dynamic where now you're kind of feeling this pressure not to just get the answer, but to try and appease the other person and answer the thing for the other person.

33:58Flo Crivello:And I think that that's probably the unhealthy form of time pressure. Like I think you should feel urgency as a founder to go and figure out what you're gonna be building, but that feels like the unhealthy form of it.

34:10Lindy:That I don't know. I've always felt on the fence about this, but my bias has always been thinking with your hands, and I've always liked to converge really quickly on the thing and then to figure that from there. And then if you need to climb back in a helicopter, you do that, but I think you'll make more progress by building than by thinking and talking and whiteboarding. So, but yes, I mean, these moments are actually the ones were actually the ones where I was, and that's actually counterintuitive, like most grateful for being a solo founder. Because like when we made the pivot from TeamFlow to Lindy, look, I'm telling the story in a very neat fashion, but obviously when you're in the midst of it, it's infinitely confusing.

34:51Lindy:There's so many options. It's a tough call to make. And I was like, God, I'm so happy I don't have to align with anyone to do it. I can just leave the room and tell guys who are doing this and also who are, you know, parting ways with two thirds of the company. I don't know what would have happened if there was another co-founder that I had to convince. And I've seen many teams just break up at that moment. Andy Grove talks about the valley of death. You know, when you're going through those huge transition periods. And it's like between two peaks, you have this valley of death, which is like so painful and so confusing.

35:28Lindy:He gives an advice, which is like at first you let a thousand flowers bloom and you let the chaos reign. You sort of embrace the chaos of that weird transition period. where there's a thousand ideas floating around and at some point you converge and you get everyone diving in the same direction. I would say actually to go back about the things I learned about this is I think there's a natural tendency as a founder and as a leader to think of yourself a little bit as a cheerleader. And it is a large part of your function as a leader. But the most important job you have as a leader is to win. And you can't win if you're not staring at a problem in the face.

36:03Lindy:And however ugly the problem, And I think a lot of founders, and it was my case, are afraid of saying something like, this is fucked, we're going to die if we don't solve it. I say it all the time now. Well, not all the time. When it's true, I say it. And I have found the fear as a founder when you say that is like, oh, people are going to leave me. And they do, in fact, leave you. But the people who leave you are probably not the people you want around anyway. Okay? Yeah. Plus, you probably do need to be shedding weight. If you're in the middle of saying something like that, maybe you should be shedding weight.

36:40Lindy:And the people who remain, they're made stronger by the experience. They're treated as owner. It actually builds trust because flow doesn't bullshit. When it says things are going really well, it's going really well. And when something's really bad, it's like, hey, we're going to die. And in a way, it sort of galvanizes them. It's like, hey, we got to solve this or we're dying. And I have found, again, it's hard enough to solve problems when you talk about them. it's impossible if you don't talk about them. So you sort of have to some extent, and obviously there's a way to do it and you can't do it with the entire team if you're 50, but you should have lieutenants, especially as a solo founder.

37:14Lindy:Everyone says, ah, solo founding, the downside is it's very lonely. Well, it doesn't have to be. You can just bring in your lieutenants with you. So you should have this small circle of two, three, four people who you completely open up to. And you have those four-hour long brainstorming sessions on a Sunday where you're like, hey, shit's fucked, what do we do? So I found this to be so, so, so important.

37:36Flo Crivello:Could you share a little bit more about that? Like from a practical perspective, obviously everybody's different. People do things like their own way. And I think that's one of the great things about companies, startups. They like successful startups. They always are, they're very different in a lot of ways in terms of how they operate. But what have you found that's been useful in terms of having like these lieutenants, these people that you can turn to and you can, you know, work in this way. And what have you seen there that's worked well for you?

38:02Lindy:There's multiple forms of thinking. I think thinking and writing is really important. I think the worst sort of thinking, I think Einstein who said, you can't do much carpentry with your bare hands and you can't do too much thinking with your bare brain. Like don't just sit around and think. So I think the hierarchy of thinking is like thinking and writing is probably the best and then thinking and sitting and doing nothing is probably the worst. And then in the middle, there's like thinking and talking it out with your team. And in some ways, this actually very often yields a type of insight that's qualitatively different from the one you get by just thinking in writing.

38:36Lindy:I think the SAT partnership can be very powerful. There's one of my ideals that I always have in the back of my mind for what the best type of working relationship looks like when you're in that room and you're talking about the hard problems with your lieutenants and you're in that trusting, vulnerable position because you're like, hey, this is ugly, we need to figure it out. There is this documentary about South Park that's called Six Days to Air. Have you seen it? Have you heard of it?

39:02Flo Crivello:I haven't, but I love the guys behind it. It's just like a remarkable story. I'm a huge fan.

39:07Lindy:Huge fan of the show, of the guys. The story is amazing. And it's a 15-minute documentary that South Park takes six days from like, let's start talking about an episode to the episode goes on air. It's remarkable. This is why like they're always so timely. Like if there's COVID, if there's an election, it's like the week after South Park is talking about it. and the way they do it is they want they just shoot the shit and you should watch the video I think it's at like 5 or 10 minutes it's on YouTube you can watch it for free at 5 or 10 minutes in the video you see them and these guys have been working together forever and they just have like they're total bros and they're like in that crappy room drinking crappy coffee and like literally throwing balls at each other and they're just like hey what's up what did you do this weekend like what did you see like what you know and so they just shoot the shit and it's kind of like they act and it's awesome and it's like they see what jokes land and what jokes don't land and it's just like Ed Catmull in Creativity Inc talks about this he calls it it's the brain trust you know so having that relationship with you you can just be totally open with people and if the joke doesn't land alright it's fine we just move on but like when the joke lands you write it down and then day two is like okay what the fuck is the episode about day three like we actually write the episode and one single person writes it, it's Matt Stone.

40:28Lindy:That's my ideal in my head of like, we should be able to just, if the right dynamic in this room is such that you should be able to tell the person, come on, let's boot it, you know. It's like, all right, fine. And then just move on, you know. And there should be no ego, there should be no friction, there should be no, you know, it should just flow very, very naturally. It should be a brain trust.

40:44Flo Crivello:How do you think about creating space for like the free flow structure versus unstructured? What have you learned about that? Because you're a great writer, right? I've enjoyed reading what you've written over the years. It seems like you've learned a lot of things around having these kinds of conversations with the brain trust. What have you learned about structure versus unstructure?

41:07Lindy:I think you just need both. I set aside Wednesdays as like my no meeting day, which means obviously I have a bunch of meetings on the day. I have like two hours, no more on Wednesdays. But then I make the time on Wednesdays to think in writing. and then every so often and this was actually the case literally yesterday so on Wednesdays it's like our optional work from home day and we have three optional work from home days like Wednesday Saturday and Sunday

41:37Lindy:and literally I was thinking and there's just like there's been like a strategic thing that's been around the companion that's been coming from like a different bunch of different angles and it's been coming to a head a little bit and I was thinking about that yesterday morning and then I was like, hey, and I just pinged like two of these folks in the company that I have this like relationship with. Like, hey, I think we should jam this afternoon. So I just biked to the office and we just had like a, I think, hour and a half, two hour long conversation. It was very unstructured and it's like there's a whiteboard over there.

42:10Lindy:We still haven't wiped it. And it's just like it's, and in the end, I still think we're like in the early phase of like clarifying our minds about this issue. There's this framework that designers talk about. Have you heard of like the double diamond? No. It's, you've got a diamond of the problem and a diamond of the solution. And so it's like you first open up the diamond of the problem, or it's like you discover. And it's like this is when things are most unclear. And then you close the diamond, and it's like when you clarify the problem you're solving really, really narrowly. It's like, okay, this is what we're solving, right?

42:40Lindy:And then you do the same for the solutions. Like, okay, how the hell can we open up? How the hell can we solve this solution? and it's just like 5 ,000 ideas on the board, and then you convert onto a solution. Interesting. That's a beautiful way of articulating.

42:53Flo Crivello:I've never heard that before.

42:54Lindy:And I think some people, one dynamic that can get in the way of that free flow of communication, collaboration, and information is some people feel bad when they're like, I want to jam about something, but I can't even put in words what I want to jam about. It's like that early and that murky right now in my head. And if anything, that's when it's most important to jam about it. You shouldn't come to the table like, hey, I don't really know what I want to jam about. You have some idea, but it's fine if it's very, very loose at first. And that's part of the process. It's a discovery system.

43:29Flo Crivello:Well, I know we're going to wrap up here in a second. Thank you so much for doing this. I would love to end with two questions. It's always really interesting to hear people's answers. The first question is sort of like, it's sort of the bear case for being a solo founder. the reasons that maybe you shouldn't. And then we follow it up with the case for solo founding. So maybe start with the bear case. We'll chop up on that for a minute here, and then we'll switch to the bull.

43:56Lindy:The bear case is, well, if you feel like you lack some critical skills that you need for your specific company, then you probably need to complement those skills with someone who's really good at them and who's going to be important enough for the company to be a co-founder. I think the loneliness is real. In particular, in tough times, I think you can mitigate it somehow, somewhat, by just having those trusting lieutenant relationships. But it's real and it's really painful. You have a lot on your shoulders. The bull case is that you can move so much faster and you don't deal with the bullshit.

44:35Lindy:That's amazing. All right. Well, thank you so much for doing this. This is great. Yeah. Thanks a lot for having me. It was fun.

44:40Flo Crivello:If you enjoyed this conversation, We would love it if you could share solo founders with everyone you know, particularly people who are considering starting companies solo or who are already doing it. You know, the entire goal of what we do is to normalize solo founding, encourage more people to solo found instead of end up with co-founders of convenience. If you'd like, and we'd really appreciate it, you can go leave a review on Apple. You can go give us a thumbs up. You can subscribe on the YouTube channel. Anything helps. And of course, if you are starting a company or considering starting a company, you should go look at the solo founders program.

45:10Flo Crivello:We work together with you in San Francisco alongside of a bunch of other solo founders. The idea is it's much better to be solo together than to be solo alone. I'll spend a lot of time helping you. And we also invest$100 ,000 in your company. So if you're excited to learn more about that, go check out solofounders.com slash program.