Building an AI Media and Software Empire - Ep. 31 with Brandon Gell

[00:00] Honestly, before even getting into like where every started, I feel like nobody actually really knows who Dan Shipper is. You're like this technical prodigy and like are actually like I don't even know if people know that you're really technical and like build stuff, let alone sold a company at like whatever, 14. Well, I can also go back. And first of all, that's very, very generous of you. I love being gassed up like that. I'm going to have to gas you up a little bit later. But I think technical prodigy is maybe like stretching it a little bit. [00:30] of questioning is like when I started getting into tech stuff in general, which is when I was in middle school, I read a Bill Gates biography and I was enamored. I was like, I want to be Bill Gates. I wanted to start a Microsoft competitor and I was going to name it Megasoft. [00:56] Brandon, welcome to the show. Thanks, Dan. Thanks for having me. So for people who don't know, you are Every's very first entrepreneur in residence. You're also a really talented entrepreneur. You started an insurance technology company called Clyde about, I think, seven or eight years ago. You raised like 50 million bucks. You got 100 employees. You sold it. You [01:18] I think in like March, right? [01:20] Yeah, March 14th. You sold it in March, and then you joined Every, and it's been a kind of amazing, amazing ride since you've joined. I feel like we've really, really accelerated everything we're doing. So I'm just psyched to have you on, psyched to talk about what you're doing with us, talk about Every generally, talk about our relationship, because there's a lot of cool stuff going on.

[01:44] Yeah, we surprisingly go... [01:47] pretty far back actually. [01:48] Um, [01:50] But yeah, this has been kind of a dream come true for me, honestly. I've watched... [01:56] you go from super organizers to whatever he is today. And, um, [02:01] just having this creative playground has been an amazing... [02:05] opportunity. [02:07] I love it. I love it. So I think the way we'll structure this is a little bit of a non-traditional AI and AI interview because we're going to, we'll do some AI use cases, but it'll be specifically around some of the products we've been building together inside of Every. But to get things kicked off, I thought we would sort of turn the tables a little bit and have you actually ask me a few questions so that I can kind of like lay out every, what it is, like what the background, how we got to where we are today. And then I'll turn the tables back to you. [02:37] talk about some of the some of the product work we've been we've been doing and demo some of the things we've built yeah honestly before even getting into like the uh [02:45] I... [02:46] wherever he started, I feel like nobody actually really knows who Dan Shipper is. And the fact that you're like this technical prodigy, [02:56] And like are actually high. Like, I don't even know if people know that you're really technical and like build stuff. [03:01] let alone sold a company at like whatever, 14. [03:05] Um, [03:06] So I feel like you should just give... [03:09] Me that I don't even know the full story. [03:12] But like, I know you started a company in college. So maybe we start there.

[03:15] Well, I can also go back. And first of all, that's very, very generous of you. I love being gassed up like that. I'm going to have to gas you up a little bit later. But I think technical prodigy is maybe stretching it a little bit. But why don't I go back? I think usually where I start on this kind of line of questioning is when I started getting into tech stuff in general, which is when I was in middle school. [03:45] and I was enamored. I was like, I want to be Bill Gates. I wanted to start a Microsoft competitor and I was going to name it Megasoft. Great name, I know. And I actually still have the notebooks from that time period. And I had a whole plan for how I was going to start this company. And the plan was step one, write soft. I didn't even finish software, just write soft. Step two, [04:15] write soft. Like this was just, you wrote that in the notebook and it was just write soft. Yeah. Write soft. Cause I was going to build a windows, an alternative to windows. That was my, my goal. So I was got it. Sure. Easy. [04:27] Yeah, I was doing the like the plan. So write soft and then burn it to CDs. [04:34] because it was, I don't know if you remember, do you remember the days when AOL, in every grocery store, you could get a little AOL disk, and then you would install it? Yeah, definitely. So I wanted to do that. And then the third step was distribute to mailboxes.

[04:49] Um, and then, which, you know, makes sense. You're following a set game plan here. That's been success was really successful until it wasn't. Yeah. [04:58] Um, distribute to mailboxes. And then, um, and then the last step was wait. Um, and that was my whole, my whole strategy. Um, nice. Yeah. But that's, that's basically why I learned to code. Cause I was like, I wanted to like build this Microsoft competitor. Um, and I like made my dad go out and buy me a book on basic, the programming language. And, um, I was sort of off to the races from there. I quickly like realized that, um, I was not going to build a Microsoft competitor, [05:28] doing it because [05:30] I was always interested in building businesses and being technical at that point. Like, um, it was the only way that I could build a business where the only cost was my time. [05:40] Um, so I was a middle schooler, like empowered me to like build businesses where I could actually make money. And that was like, I was, I thought that was the coolest thing ever. [05:47] Yeah. I mean, I think that's amazing as a middle schooler that you were so obsessed with this. I was certainly not. I don't even think I knew what coding was. [05:56] Um, [05:57] I don't even know what I was doing. I was like, yeah, what were you doing? I was tossing a Frisbee somewhere. I was like very sporty, you know, kid. Yeah. See, I was like, I was not athletic at all, which may be like, you know, helped helped me get into being technical because otherwise I would have been outside with friends. Yeah. Yeah. I don't know about friends, but I was playing sports. And also it should be, I think it's important for everybody to know that you are. I mean, I don't know if you're actually still obsessed with Bill Gates,

[06:27] at every called Think Week once a quarter. And I know that [06:31] I actually didn't know when I started here that that is what Bill Gates used to call his like... [06:38] when you would run away to a cabin. Yeah. Um, so, you know, there's still, there's still that through line still inspiring stuff here. Yeah. Still Gates inspired, uh, have not, have not unseated windows yet, but there's still time. Totally. Yeah. Our next, our next incubation. Yeah. I think the next like, um, kind of stop on the trajectory is, um, um, [07:01] I was programming for a while. I built a bunch of little dinky stuff that didn't really matter. And then when I was in late middle school, early high school, [07:09] I started noticing that, um, [07:13] smartphones were becoming a thing. So like Nokia smartphones and BlackBerrys and that you could actually start to build software for those phones, like third-party apps. And I remembered from my Bill Gates days that new hardware platforms are often really good opportunities to build interesting software businesses. And so I got really obsessed with building software for phones. And this is before the iPhone came out. So there was no word app. [07:43] first piece of software that I built. [07:45] was called Find It. And basically, I kept losing my BlackBerry in my house, and it would be on silent, and I couldn't make it ring. So Find It was a little app that sat on your phone, and it listened for emails to come in with a special string in the subject line saying, like, I'm lost, please help.

[08:04] And if you sent that email, your BlackBerry would ring, even if it was on silent, which I thought was like the coolest thing ever. [08:12] And I eventually sort of like iterated that, like it had a full fledged web interface. You could like track your phone on a map. You could lock it. You could back it up. You could make it call you, which is kind of cool feature. And, and, and yeah, it just, I had like a bunch of customers. It wasn't like a huge business or anything, but it's how I paid for gas and food in high school. [08:42] or 20 bucks forever instead of being SaaS because Stripe didn't exist. So like it was way too hard to build subscription software. Um, and yeah, I w I would have had a lot more money if Stripe had existed when I was in high school. So. Although that's, that's, that's coming back, that form of paying for software. So maybe you were just like really, really early to that trend. Um, [09:04] Well, I think that's like one thing. One thing that's been really cool working with you is I just think that being able to identify problems is actually really hard. [09:18] Not because there's [09:20] not infinite numbers of problems that exist, but because it's actually a muscle to recognize that something that you are experiencing is even a problem versus just your experience, your lived experience. And I feel like that's something that,

[09:34] that I know that you're really good at and it turns out you've been like [09:39] It's a muscle and you've just been like... [09:42] working on that muscle for, [09:44] a very long time. It's certainly a muscle that like, I, I'm still pretty early stage. And I sort of feel like a lot of the ideas that I have, I sort of fall into versus, um, [09:55] I feel like you have a bit of like a practiced, refined experience. [09:59] muscle of [10:01] Even identifying, okay, this, you know, a phone is a new platform that people will need to be able to build stuff on. It's a new interface. And yeah, it's pretty, pretty cool that you've been doing that for so long. Thank you. I really appreciate that. That means a lot. I've not really thought about the, like the problem identification muscle, but it definitely is a muscle. I mean, maybe it's sort of like partly like my Jewish neuroticism, you know, I'm just like constantly complaining about things. So I can see the problems. [10:31] But yeah, it's, it's, it's been something that I've been doing for a while. And, and I actually just love, I love looking at the world in that way. Cause it makes me sort of, I think there's a way to look for problems in a way that's like, oh, this sucks. And like the world sucks or whatever. And then there's a way to look at like the world and see problems and be like, but we're empowered to like fix them. And that always makes me like really excited. Cause I'm like, Ooh, there's something new to do. Like I have a new project to do, you know?

[11:01] Like, [11:01] So it's, it's, it's like easier, obviously to problem solve something once you're put into a box, but it's really hard to identify what that box is sometimes. And like, [11:13] So I studied architecture in college and what, [11:17] I got really good at was being put into a box. It's like, Hey, here's, here's like a building that we need to like renovate, or here's a space that we need to put a building on. And here's the box. And now we can like think about all of these interesting ways to, to like solve the problem within the box. But we never really were like, [11:35] Hey, go out and try to figure out what the box even is. [11:38] Because then you're just like looking at the whole world and it's sort of infinite possibilities. And it's really... [11:43] quite hard to like define a box. I think you're totally right. And I think that that's like, in general, one of the kind of things that school doesn't give you. And I'm kind of like happy that I did spend a lot of time doing side projects and stuff as a kid, because I had to define the box, because like at that point, there were no like, you couldn't even take a computer science class, there were no real business classes for kids, like there's nothing on the internet. So it was just me kind of like, being like, how can I do something that would actually work? And so I think [12:13] That's another skill. That's, yeah, that's really interesting that, that you feel that way about the, about architecture. One of the things that I think is really cool about, uh, [12:20] architecture programs and people who have studied architecture is it's a very like multidisciplinary thing. Like it's sort of halfway between art and engineering. And I feel like you kind of you kind of incorporate that in the way that you think in the way that you build products and stuff like that. Has that like how is that sort of affected affected the way you look at the world?

[12:39] I think the biggest thing that I learned through architecture is just being iterative. [12:45] and not getting stuck on [12:48] a solution. [12:50] And like, I was the type of kid growing up that would like, [12:55] If I had to write a paper, I'm writing it one time and I'm not even editing it. I'm just writing it and submitting it. And that's how I did homework. And then I went to college and I studied architecture. And I was like, oh, I'm not going to get to the best solution. [13:12] If that's how I operate, like my first design is going to be the worst. [13:17] or the best, I won't know until I like throw a bunch of stuff at the wall. [13:21] And it would be a big mistake to try to get caught. [13:25] or to get stuck on what my first solution is. So just being comfortable like, [13:33] iterating, I think, a lot is... [13:37] Probably the best thing I got from architecture. And then being able to take critiques... [13:42] A lot of critiques in architecture. I bet. Isn't it like architecture was like really intense. Like they're like yelling at you a lot and there's late nights and stuff. Right. Or am I right? Yeah. There's a lot of studio time. I also went to like Middlebury liberal arts architecture school, which was like. [13:58] kind of like a bit of a janky version of architect. I wanted to be an industrial designer. Um, so I just like, it was like sort of a path to do that. Um, [14:06] But yeah, it was still pretty hard. And, uh,

[14:09] A lot of feedback, definitely. [14:11] So in the kind of like iteration, like the thing I'm kind of keying on and the thing I'm interested in on the iteration front is like, how are you taught to do that? Are they just telling you like you have to do a lot of these things or like what is the process by which you learn to iterate? [14:31] It's like all sketching. It's just a lot of sketching. And like, I really like computers. And I was like, from a very young age teaching myself. [14:40] video editing software and, um, [14:43] all types of like, [14:45] video effects software and a ton of 3d software rendering software. And then I was like, great, I'll go to architecture school and like be able to use that. And that'll be so much fun. So like, [14:58] Freshman year, we had a project and it immediately brought open my computer and was like, great, I'm going to start rendering something. And, you know. [15:07] And my teacher was just like, this is not what we do. Like, you're going to spend the next quarter just sketching and drawing. And I sucked at drawing. [15:16] So it's just building the muscle of constantly learning, [15:20] Looking at the world eyes wide open, [15:22] And, [15:23] being able to see interesting things like, like, [15:26] process those interesting things, draw them, take pictures of them, sort of store them away, and then keep going forward. [15:34] and not getting stuck on them. Because like any sort of innovation that you have in architecture, or even what we do, is sort of going to be the amalgamation of a bunch of different things

[15:46] inspirations that you've sort of pushed together. And when you get stuck in, [15:52] on something, it's impossible to come up with something new. You're just going to end up coming up with like a derivative of that thing that you're stuck on. So for me, it was just a ton of, it was a ton of drawing and building the muscle of being able to like, [16:08] Let stuff go flip the page, go for a walk, try to think about the next, the next thing. I love that. I think it, I think it really, uh, also that connects back to the thing you were talking about for me, like seeing the problems to solve, like it helps you look at the world in a certain way. And I think that that's always the like first start to doing really great creative work. [16:27] Yeah. [16:28] Um, [16:29] And you're actually really good at that. Like a lot of times I'll see you like go for a walk and you've, you've told that story of like just talking to chat GPT and, [16:37] using it as like a recording device, but one that gives you feedback and, um, [16:42] That's like pretty amazing. [16:44] way to [16:46] let stuff go and then process through stuff. I do want to go back to the fact that you, um, [16:52] started a company in college. [16:55] And talk a little bit about that. And maybe you could go off on that. [16:58] or what that was like. Totally. So basically by the time I got to college, um, you know, I, I had, I had built this first company. It was called, I mean, it wasn't a company, but it was like, it was, you know, a little business called convenience software and I had all these different apps or whatever. And then when I got to college, um, I,

[17:18] That's when I was in 2010 is when I got to college and that was, um, [17:25] Right around that time was when Facebook started to really take off and the idea of web apps and software as a service apps and all that kind of stuff started to really take off. Stripe. [17:37] like had just started. Um, I actually had John Collison, the, uh, one of Stripe's co-founders. He, um, he needed to get a visa to stay in the U S and so he needed to do speaking engagements to like [17:51] show that he was like legit enough to stay. And so he came to Penn and like, I brought him to Penn and he came in, like spoke to us and we wanted to dinner with him and all that kind of stuff. It was really, that's awesome. Why has he not been on the podcast? You like, I honestly like made Stripe possible, basically. John, if you're listening, um, no, I mean like he used to try to actually, like we, we kept in touch. He, he asked me to join Stripe a couple of times, which I said no to, which was the, probably one of the biggest mistakes of my career. Now that he's a billionaire, [18:21] else. So, um, John, if you're listening, like, I love you, like come back into my life. We'll have you on. Uh, would love to learn how you use chat GPT. You owe, I mean, he owes, he owes you. He does. Basically. Yeah. I should frame it that way. Yeah, he does. Anyway, he's a good guy. He's a good guy. Yes. Um, so, uh, so anyway, uh, I did a, I just did a bunch of projects. I was working with a couple of different friends doing a lot of different things. Um, and,

[18:49] But the, in my sophomore year, I decided I really wanted to focus on building B2B software. Cause I was like, I want to build, I want to learn how to build a real business. Like I want to learn how to build something that makes money from day one that I can grow like from school that I can mostly bootstrap, um, all that kind of stuff. And yeah. [19:10] I was on the phone with my dad and he was complaining to me. So you complaining, it's a, it's a, you know, it's a thing. Um, a good way to find good way to find startup ideas. He was complaining to me about, so he runs this, um, [19:23] He has a cemetery and funeral home company. And so he spends a lot of time, he's an entrepreneur himself, and he spends a lot of time on the phone talking about architectural diagrams and layouts of cemeteries and stuff like that. And he really wanted something where if he was on the phone, he was talking about [19:42] a diagram that he had he had up on his computer and the person on the other end was also had the diagram up. [19:48] He wanted like a grid to come down from the top of his computer screen. [19:53] sort of like battleship and be able to say like, okay, like look at cell E5 or whatever. Um, and he was like, can you build that for me? And I was like, dad, that's dumb. That's a stupid idea. Um, and that's how most great ideas start. I feel like, um, but I told that to my, uh, who, the people who ended up being my two co-founders, Firefly, which is the company that I started in college. Um,

[20:23] apps. [20:25] We were working together on another SaaS product at the time. [20:29] And they sort of took the weekend to build that. And at the hackathon, a company came up to them and was like, we want to use this for our customer service. We want to integrate it so that if people have problems with our website, we can help them through the site. And so they came back and we were all talking about it. And we were like, okay, do we do this or the other one, which was the other one was email signature marketing. [20:55] and [20:56] companies would have their employees put it in and advertise their, their, you know, all their products or whatever. Um, and we're like, I don't know, like it's hard to sell email signature marketing products. Like, why don't we just like try this one? Right. You got a buyer. Exactly. Like, you know, that's, that's like the, that's the first thing where you're like, Oh wow, this is really cool. What's funny is like, they just let us on for like six months and never actually bought it. Yeah. It's classic SAS B2B buyer. Yeah. I had a lot, I had a lot to [21:26] And so – [21:28] So we took a summer, just like rented a little apartment in Philly, and we worked on this product. And by the end of the summer, we had like a really well-functioning product. The technology we built is called co-browsing. And co-browsing is sort of like screen sharing, but instead of sharing a browser, sorry, instead of sharing what's on a desktop, you share what's on a web page. And it doesn't require any downloads or installations.

[21:58] based, um, and it's cross platform. So you could be on a PC or a Mac or an iPad or whatever. Um, and we applied the technology to customer service. So if the customer is having a problem with the website, we allow the agent to basically, um, whoever they're talking to on the phone or over chat to basically look over their shoulder, see what they're doing on the, on the website in real time and help them through the site in real time. Um, and it was, it was like a very, very cool technology. Um, [22:24] And, uh, but it was incredibly hard to build. It's very, very just difficult to like make it work cross, cross platform and cross browser and with any kind of update or whatever. And it had to work back to IE8. So I can't even tell you the like, the like late nights that I spent, uh, with my co-founders, like trying to fix some, like a random bug in like IE8 and on like [22:54] Um, but basically ran that, ran that business for a couple of years. Um, got a, got a bunch of customers, got a bunch of traction, especially for where we, where we were because we were, um, [23:02] We didn't take any money. We raised $20K in total from the Dorm Room Fund, which is first-round capitals. We were the first investment of Dorm Room Fund. And then we sold the company to Pega, which is a big public enterprise software company. And they have a big CRM that they sell to banks and insurance companies.

[23:32] And they wanted a cloud solution that they could sort of sell as a tip of the spear into those companies. And how old are you when they approach you and say, we want to buy this? I was 22 when they approached me, and I was 23 when we sold it. I flew from my college graduation to Boston to finish negotiating the deal. [23:56] And like to put us in that room, you're like 22, you like know nothing. Basically, I mean, I started my company at 22 and I knew nothing. So like you knew a little bit more than me, but relatively nothing. [24:09] And so like you're in that room, there's, yeah, I see me at a lawyer. [24:14] I mean, we definitely had a lawyer during the negotiations. [24:19] I'm thinking about like... [24:22] Yeah, I mean, honestly, I haven't thought about this in a long time, but... [24:26] It was basically like the way that the way it all happened is is part of the way we got traction for the business is we sold this co-browsing tool to companies that had big platforms like chat platforms or CRM platforms. They would integrate it into their platform and then sell it to their customers. So we were kind of like an OEM into other big platforms. [24:56] uh, like working with a couple of partners and one of them was like, Hey, like, why don't we just buy you? Cause like, we want this as part of the, as part of the platform, um, instead of like integrating and why don't we just buy the company outright. And that was like a really big, um, live chat customer service company.

[25:12] And, um, [25:15] And we kind of like went through the diligence process with them, which was like freaking, it was wild. Like I remember. You're in college at this point. Yeah. Like going through finals and stuff. Yeah. Did you even care about schoolwork or is it like this is, you know, nothing compared to I'm selling a company right now. This is crazy. I did. I like school. I majored in philosophy and like I wanted to be really well read. And so. [25:42] the like really fun part of majoring in philosophy is, [25:45] You just read tons of books. And I actually thought there was a lot of overlap between philosophy stuff and philosophy. [25:52] entrepreneurship stuff because, um, [25:55] Like at the time, the big... [25:57] methodology for starting companies was like the lean startup, which is like a startup is like science. And a lot of, for example, some of the things that I was like really into in college, philosophy wise was philosophy of science, which is like, what is science actually? And so if you want to do a lean startup and you're like hypothesis testing or whatever, then you're like, oh, wait, but like, how does science actually work? Like that's, but we should take that metaphor really seriously. And then you're like, well, [26:20] then you're just reading. Just for the listeners out there, Dan reads like the hardest books to understand that like, [26:27] are simultaneously super interesting. It's so boring. [26:31] And he just loves them. [26:33] I do. It's like, it's my happy place to read like extremely boring, extremely fancy books for some reason. Um, um, [26:41] This is like my nightmare. I know.

[26:45] If I'm not reading a three-body problem style book, it's like... [26:51] Look, I'm just taking one for the team. I read it so other people don't have to. Yeah, definitely. Someone's got to read them. [26:58] So back to that live chat company, they were very, very serious. I went in to negotiate that deal, again, still in college. And we were in their lawyer's offices with the glass that it's electrified. [27:15] it gets frosted automatically when you go in and then it unfrosts itself. So I was in one of those. And they're... [27:23] They're like head of biz dev guy comes in and he's just like a really like intimidating, intense Israeli dude. [27:30] And who like like rides a Harley and he he like plugs his laptop in. [27:40] And I'm trying to remember the exact words, but he had his Evernote up by accident and [27:45] I can't remember the exact words, but it was like, um, something like be aggressive, like let them know that we have other options. Um, like it was something like that. Like, like tell them, tell them that they suck and that we have other options. Yeah. [27:59] Right. Yeah. Bully the college kid that you're trying to buy the company from. [28:06] Actually, looking back on that, he was probably in his 30s or 40s, and yeah, we were 22. That's pretty fucked up. Yeah, that's kind of... Anyway, so you didn't get acquired by them. Well, basically, we were in the process of getting acquired by them. So we were going through the diligence...

[28:24] even though like, you know, he was kind of a dick a little bit, um, or, you know, they were, they were really pressing us. We're going through the diligence and, um, [28:33] While that was happening, it was taking a while. While that was happening, someone from Pega reached out and they were like, hey, we want to partner with you. We want to integrate this in our platform. And we were like, hey, we would love that, but we may not be around to partner with, wink, wink or whatever. [28:49] And they were like, ooh, well, maybe we would buy you. And so then we got a little bit of an auction going. And so we went through the process with Pega. And everyone there was really, really nice. And they took us really seriously, even though we were super young, which I, looking back, deeply, deeply appreciate. And they kept all their promises, which was really great. [29:19] We were negotiating with Pega, and we got into a range, a number that we thought was like, [29:24] reasonable with them. And so we went back to this other company and we were like, [29:29] we were like, [29:30] And then we were like, the price just tripled, you know, just to like see if we could like just get a lot of money for it. [29:37] And basically they were like, no. And so we ended up getting acquired by Pega, but it was it was a fun it was a fun. What an amazing experience at 22. I mean. [29:48] I went through a similar experience at 2018. [29:51] eight and it's [29:54] I mean, I've really, really, it's selling a company is a very hard, doesn't matter how good your company is. It's really, really hard to do.

[30:04] And to do it at 22... [30:06] is pretty wild. [30:08] Thank you. [30:09] to go through that. [30:10] Yeah, it's it's hard. It's distracting. Like it's just so emotional. It takes such an emotional investment to like do that. Like it's just hard to like focus on your work. [30:21] Yeah. I mean, I have an anecdote from when I sold my company, my, my, um, good friend, uh, I was so wrapped up in, in Clyde and like what we were building and making sure that it was trying to be successful. And it was like, wow. [30:33] became who I was. [30:35] Um, [30:37] for better, for worse, kind of necessary to like make it successful. Um, but also, [30:44] Not great. And I remember my friend Thomas threw a dinner for me. It was a surprise dinner like two weeks later. And I. [30:55] My sister was there. My wife was there, like a bunch of people. And I stood up to like give a toast to them for like being supportive. And I just started bawling. I like couldn't I couldn't get it out. And then I was like, all right, I'll take a breather and I'll try it again in 20 minutes. Stood up again to make the toast. Just started bawling again. I couldn't do it. And I. [31:18] And yeah, I mean, I was like... [31:20] I... [31:22] 28 and... [31:24] had more life experience than you had at 22. And I don't think it gets easier. [31:30] I think if you're really building something, you get really, really caught up in it. [31:34] And it's hard no matter what.

[31:36] to say goodbye to it. It's like a part of where you are. [31:39] It's really hard and it's actually one of those things where once it was done, that's when I had my first panic attack. [31:46] I was holding my feet together and then I started having panic attacks after I was done. Oh, I think so. A week after I sold Clyde, I got extremely sick. [31:59] And I was like, oh, I guess it's possible to like just get sick from like stress or something. Yeah, yeah, yeah. [32:04] But yeah, I mean, another sort of, [32:06] I, I'm like, just not, I, well, I wasn't like a stressed or anxious person. I just was able to sort of manage that super well. And I went for a walk with, [32:17] Lydia, my wife, at one point during Clyde and I, [32:22] I was just like, I don't know how I feel really weird right now. And like, I, I, I'm uncomfortable and I can't turn my brain off. And like, what is, I don't know what's happening to me. And she like stopped walking and like put her hands on my shoulders and we're like, this is called anxiety. And I was, it was like such an eyeopening moment for me. I was like, shit. [32:44] I guess I do feel that. It's really hard. [32:49] No, I think people should know for context that your wife is a therapist. True. Yeah. [32:57] Yeah. But I don't think it was hard to tell. Yeah. I just couldn't tell. [33:02] I had that too. I mean, I didn't know any, like, I didn't know about any of this stuff until I like literally stopped being able to breathe.

[33:09] because I was having panic attacks. That was the moment where I was like, oh, I guess I'm stressed. I guess I'm anxious. Because you get very used to just... [33:19] if you're a founder, like kind of running toward the pain or like running towards the stress or whatever. And like it, I mean, to some degree it's like, it's exciting to be, have so much going on and have so much pressure and all that kind of stuff. And then if you take it too far, it, it gets like, it gets to be too much. Actually, I think this is a very good segue to, um, [33:39] Every. [33:40] And like how every started, why you wanted to build what was originally super organizers. I think both like what was it? And then also, why did you want to build it? Yeah, good. Really, really, really good. Good question. I spent like so basically I ran the business, the Firefly business inside of Pega for a couple of years. And then I left in 2016 ish. And I spent probably like four, almost four years, like just wandering the desert proverbially. [34:10] Um, so I was, I, you know, I wrote a novel. I like did some angel investing. I worked at an incubator [34:17] um, called prehype. And, um, basically in 2019 ish, I was like, okay, I think I just want to start another company. Like I've tried a lot of other things and, um, [34:30] I really like starting companies. I'm going to do that. And I wanted to start a... [34:35] like a tools for thought kind of business, like a Rome notion, like note-taking kind of like company. And I was like, how am I going to do that? Because I had a bunch of ideas for how to do it.

[34:47] Um, and, um, what I, what I wanted to start with was like, instead of starting with my ideas, I wanted to like, um, interview, like do customer interviews with people to like try to understand how they were taking notes, especially like really interesting people. Um, and, and then try to build a product like around that. [35:05] And so I was like, oh, what I'll do is I'll start a newsletter and, [35:10] And I'll tell people that I'm interviewing them for the newsletter so that they'll tell me about their note-taking system and their productivity system and how they do their email and their to-do list and all that kind of stuff. [35:20] And then I'll take what I learn. I'll write the newsletter because I love writing. [35:26] And [35:27] And then I'll just build a software business and sell it to the audience when I've built something that I think is good. And what I tell people is for a long time, I just got stuck on building the newsletter. It turned out I just really liked it. And it kind of combined this... [35:49] um, love of writing that I've had for forever and my sort of like love of business and building stuff. And, [35:55] And I got really interested in, at the time, building business newsletters and the idea that people would pay a subscription fee for them because it was at the very beginning of the substack creator economy wave. And so... [36:10] I started working with my co-founder, Nathan, who we'd been friends for a really long time. He was the first employee at Substack. And we sort of together sort of came up with this idea to...

[36:19] build a media company for this like new internet age this new sort of sub stacky creator economy age where what we saw is a there's like this this like movement of people like unbundling from traditional publications and starting their own sub stacks um but b um like that had a lot of drawbacks so they're sort of trading like they're getting a lot of upside so if you if you make it you can like [36:47] you can make a lot of money. You have a really good business. Like Ben Thompson probably makes like 3 million a year, like cash or something like that. Like it's crazy. Um, and it's all profit. Um, and, um, but what you trade is you kind of like lose a lot of the camaraderie. Um, you lose a lot of the like, um, editorial support. Um, like you're running a business by yourself. Like that's a lot. Um, it's lonely and also creative business. Exactly. Exactly. And it's, [37:17] break. You have to write every week. There's no vacations. So... [37:22] That's actually really hard and very few people can actually do that. And also for readers, it's not as good because there's only a certain kind of content that you can write if you have to write every week or every couple of days. You can't write really big long corn pieces or whatever. [37:40] And then for all also for readers, they have to pay individually for each writer. So that's just like not as economical as like just paying for a publication that has a lot of writers inside of it. And so we were like, what if we built like a bundle of business newsletters?

[37:59] And we tried to create like a single subscription that readers would be able to get access to a bunch of business writers, business and technology writers that were kind of like the ones that we liked. And then we tried to create a system to compensate bundle writers that had a lot of the benefits of being on your own. So like we had this whole system for like calculating how much bundle revenue you would get. So you could if you attracted more readers, you would make more upside. [38:29] Um, [38:30] Uh, but we also had like a lot of the benefits of building together. So, you know, we had a discord and we were, you know, we, we edited, we had an editor and we were all kind of like working together to make each other better. And, um, so that was like the original impetus for every, and we started bundling in writers. We were like a collective type. Exactly. So we called it a writer, a writer collective. Um, yeah. [38:54] And so, and to the like... [38:56] To kind of tie it back to my previous experiences, I had just gone through this thing with my previous company where – [39:03] Um, [39:04] I loved building that business and I learned a lot from it, but I also wasn't passionate about it. It didn't matter that. Co-browsing is cool, but it's not my life's work or whatever. [39:16] And what I really wanted to try to find was something like a business to run or to start that... [39:22] Thank you. [39:23] Had that kind of like upside to it, but also, um, just, I just loved, like, it just kind of like pulled at my heart a little bit. And I felt that way about this. And I still, I still feel that way. Um, it like you, you talked earlier about like the creative playground and I think that's what every is. And it's like, that is the best. It's so fun to like wake up every day and do that. Um, and it's just, it's a different feeling than like, um, the B2B SaaS stuff, which is cool,

[39:53] To me, the core... [39:56] of every field. It feels different. It's warmer. [40:00] Yeah. And then where did that go wrong? Like the collective idea? So the problem that we found was... [40:11] There are very few writers that can actually make it on the internet. [40:17] Thank you. [40:18] And there are even fewer business writers. [40:21] because in order to be a really good... [40:25] A business writer, you have to know what you're talking about. You have to be able to write. [40:31] You have to be able to do it [40:32] all the time, every week or more, at least weekly, maybe more. And you have to want to. [40:39] And those four things are very, very, very rare. So especially in the business world, one of the reasons why there's a lack of really good business and technology writers is because if you really know what you're doing business-wise, you can make way more money just working as an executive or starting a company or whatever. The upside is way higher for anything other than writing. So there are plenty of people who probably could be business writers who... [41:06] Don't because it's just like, well, I'd rather I'd rather have a like make money, which makes sense. And so and so what we found is like basically we started the company. We were the main writers when we started. Everything was growing. We're like, cool. We'll just go like hire.

[41:26] Now we raise money. It's like a real business. Now, instead of being the writers, we're going to go hire writers. And as soon as we started to do that, the business just stopped working because the weird, hard thing about media is if you have product market fit with a particular writer and then you change the writer... [41:44] You lose product market fit. And writers are the rarest thing. Good writers are the rarest thing. And so the business started going like this. And we were just sort of following the playbook that we had learned running our previous companies. But that's one of the key differences between media and software. In software, it's the best practice for the founder to be technical and build the first version of the product. And then you hire people to build the rest of it. And in media, that doesn't work at all. [42:13] Um, uh, for the, for the reason I just talked about. So for a while, the business was like sort of stagnating, even though we were, we had other writers doing it. Um, and then through that whole period, we like found one writer who was like good enough to like really sort of be part of it and help carry the, um, the publication or what became the publication. Um, and, um, [42:35] His name is Evan, and he writes napkin math for every... But over time, what we've found is like... [42:41] um, the idea of, of having this like scalable collective of like all these different writers, like just didn't work because the, the supply constraints of writers were like really hard to work out. And then also just like figuring out the bundle economics was really hard. Bundle economics are just, just, it's just like, it's like a mess basically. Um, and everyone like there's the system gets complicated and everyone's unhappy and whatever. So it's like, it's very hard to do. A lot of people do it because it's like, it's a great business if you can make it work,

[43:11] so [43:13] Um, so anyway, so eventually we kind of like realized, yeah, what we're really doing is we're not building like, [43:22] all these different newsletters. Cause like only a couple of them, only a couple of the writers are really working. We're really building, like we should really just build one or two, one newsletter and like have the, have all the writers that are working in one place. Um, and then we can have the other ones that aren't working as well. Like we can have them contribute, but we should just like be focusing all our effort on like the winner or winners basically. And also like around that time, [43:52] that I wanted to write more. Um, and that also like helped a lot. Cause, um, that's like, I love it. That's the thing I'm, I, I, I love doing and I'm pretty good at it. So I kind of like made the decision instead of like, um, [44:06] doing the typical CEO thing and like, um, hiring other people to do like a lot of the on the ground work. Um, [44:13] that I would also like be a or the main writer. [44:19] I think that is actually a really important point and also kind of like, [44:24] part of why I wanted to join every two, which is like... [44:28] You... [44:29] felt like the need to [44:32] not right because you're supposed to like scale the company, even though it's what you're good at and it's what you like to do, which is like just to, [44:40] It's what you're good at and what you like to do, yet you're supposed to not do that. And I think that one thing that I've just loved being here at Every is – I don't know if I can say this on the podcast, but like that. You should just do the thing that you're really good at and you like to do, and you can just –

[44:59] It just feels like such an unlock to be able to... [45:03] with confidence do that. I feel like a lot of my first company building experience was like, oh, I'm supposed to manage my board like this. And I'm supposed to hire in this way. And we're supposed to build product with three engineers and one designer, 1 PM per pod. And I'm going [45:20] And it's Brian Chesky actually has a great talk about like designing your company. [45:27] And, um, [45:30] I feel like that's exactly what we're doing here. And it's just, it's very, it's a better business and it's more fun. Yeah, totally. I think you're, I think you're spot on. It's, and it's, it's sort of like, that's, that's what I do with my first company too, in a lot of ways. And like, it's, I think it's part of maybe being like a younger entrepreneur and then, and, but some people never grow out of it. And I think what we're trying to do at every is like, yeah, [45:56] actually look at what do we want to do and who are we and how can we make this thing a reflection of that instead of being like, what are we supposed to do? And for me, that has been a journey because I feel like I'm constantly fighting that tendency in myself to – [46:14] pick up other people's expectations and then like, [46:17] try to fulfill them regardless of what I want. And it's, it's taken a while to like, [46:22] figure out how to do that. I'm still, I still failed it, um, often, but like, I think it's, it's becoming more like that, which is really great. Um, yeah.

[46:30] So, okay. So, so, uh, every now this or like one newsletter, actually, if you're in every subscriber, you can actually like see the legacy, you know, all of the columns still on through the account creation part of the, uh, the, the website. Um, so this changed to be like sort of one newsletter and then, [46:54] I mean, now it's evolving a lot. In the past four months, I feel like there's been... [46:59] You know, sort of unbeknownst to a lot of listeners and readers, there's been a ton of [47:04] transitioned and evolution that was announced in the every master plan, uh, article that you wrote. But like, maybe you could talk about that a little bit. Yeah. I'd love to talk about it. I will also say like in that kind of like all that sort of the messy middle period, um, [47:19] my co-founder Nathan built this app called Lex. And we were kind of, we spent a lot of time in, in Google docs, like, you know, editing, writing and all that kind of stuff. And he was like, very kind of like, maybe there would be a better Google docs. And it always been kind of like in our mind to like build little products, like, cause that's, [47:38] sort of where the original idea for every came from. And we'd done that along the way. And so he started, he started building what became Lex. And it was right around the time where GPT three was like starting to take off. ChatGPT had not been released yet. We were like, it'd be kind of cool if you just like put that into the, into that word processor you're making. So he, he built Lex, we launched it and it just like went super, super, super, super viral.

[48:05] and we spun it out as his own business. So he now runs that. It's still part of the bundle that we offer to our subscribers, but it's a separate business. [48:16] And I think that was another accelerant for me to be like, well, what do I really want? Like my co-founder's gone. Like this is – every business has a bunch of different like reinvention moments. And I think that was like a – that was a reinvention moment to be like, okay, like what do I want and what do I want this to be and like who am I and all that kind of stuff. So I've written a lot about that and that was part of the process of me being like – I think at the core, like I'm like a writer, you know. [48:40] Yeah. [48:40] And I think actually what I'd love to do is like – because there's this kind of like every master plan. But before I wrote that article, like we had you – like you joined. And I think it would be nice to like – [48:54] Talk a little bit about that and that process. And like, I don't want to, I don't want to swerve the whole thing. But like, one of the things I'm like, I'm wondering, because we got to talk about my origin story. And I don't think I even know your origin story. Like, [49:09] Obviously, we've been friends for a while. You came on to every after your last business. How did you start getting the entrepreneurship thing? What were the origins for you? Yeah. Well, earliest days, it was sort of classic... [49:26] taking stuff apart, you know, building stuff with Legos in my earliest days. Um, and, [49:34] I can't, I've always loved making stuff, but it was always with my hands. Um, but I was never good at math.

[49:43] Um, [49:44] End. [49:45] I, I, [49:47] So I ended up going to... [49:51] um, a liberal arts college called Middlebury in Vermont. And, um, I, [49:57] Pretty much the only reason I chose to go there was because they were a part of a competition called the Solar Decathlon that the Department of Energy was putting on. [50:07] And the challenge was basically... [50:11] Build a house that's entirely solar powered. [50:15] Um, [50:17] You have to fly it, train it, drive it to... [50:22] Irvine, California, build it in seven days. There's a competition about like the aesthetics of the building, how well it performs, like a whole bunch of different things. And then you have to take it back to, you know, do something with it. [50:35] Um, [50:37] And like we were typical participants are like team China. [50:42] entire countries are like huge universities. And then somehow Middlebury, which is like a 2,400-person university, [50:50] liberal arts school with like [50:52] not really an architecture program and certainly not like a construction program or anything. They applied, got accepted, and then got the school give this team $1.5 million of funding. [51:06] And I somehow learned about this and was just like, this is the coolest thing ever.

[51:13] Um, [51:15] And I... [51:17] I mean, I toured Middlebury on like a crazy, crazy snowstorm and was like, this is, I love it here. [51:24] Like, and I think it was in part because it's a decathlon. I landed on campus freshman year and just like that became my world. And I taught myself AutoCAD and I sort of became like our strategy for building this, this, we wanted to make it like a really, really efficient house. And that included how we were going to get it to California. [51:44] And if you fly a house to California, that's like a lot of gas burned. If you drive it, that's a lot of gas burned. But if you train it, [51:52] it's really, really efficient to put stuff on trains. So the challenge for us building this house, aside from making it efficient and beautiful, was... [52:02] it had to be panels that were like no wider than seven feet. Nothing could be wider than seven feet. So that heavily influenced the design. And then I sort of, [52:12] freshman year, no experience with AutoCAD or architecture. It was like, [52:16] I'll teach myself AutoCAD and I'll sort of be the guy who makes like all the schematics. So I made... [52:24] Essentially, the blueprint for every single panel is, [52:27] became sort of a really, really core member of this team, which was, you know, primarily had seniors. And then there was like the 120 pound. [52:36] freshman Brandon um who like knew nothing and was like super young and um [52:43] I...

[52:45] Yeah, I stayed there that summer. We literally built the whole house, and I was a very core member of the team. At Middlebury, you didn't have to pick your major until sophomore year, and I was basically like, I love architecture. I love building things. I did a lot of building, built a bunch of furniture. I got really close with a bunch of... [53:05] people in town that were like metal workers and, you know, woodworkers that helped us build the house. So had access to all of their studios and go to their, their shops and build furniture. Um, [53:18] Thank you. [53:19] And then my senior year, I did two projects that were really, really influential, what I went on to do next. One of them was I had gotten close with this girl who wanted to build a bus. She wanted to, like, renovate a school bus, like a 52-foot bus. [53:39] yellow school bus, but had no construction experience and, [53:45] I basically came on board and the two of us, [53:49] bought a school bus, gutted it over the course of like two weeks, and then completely renovated it into like this beautiful school. [53:57] We turned it into a mobile school that taught entrepreneurship. She went on and like toured the country in this bus and had an amazing experience. [54:05] So that was like another really hands-on thing. But at the same time, I sort of started to get drawn to graphic design. And then me and a really good friend, Sharif, who you've met, went on and another friend of ours, David, went on to build a photo printing app called Photon.

[54:23] And the idea was that, [54:26] We all take a lot of photos. We never look at them. Like, wouldn't it be great to very easily print them? [54:31] Um, [54:32] I think if we had done like a second of market research, we would have known that like Shutterfly existed, but we were like, we're going to do it on our phones and it'll be really easy and easy. [54:43] you know, super low barrier to entry for people to print photos. [54:47] Amen. [54:50] Yeah, that didn't really work. Like my aunt printed a ton of photos. Um, but it was an incredible experience. We learned a lot. And, uh, [54:58] And that's sort of where it all started. And then I became a VFA fellow and went to go work. [55:04] for a startup out of Columbus, Ohio. Yeah, I think there's, I mean, there's so much in there. I mean, one that like sticks out to me is obviously just like the feeling that you love building, which is such a core like part of... [55:19] being an entrepreneur is like like loving building things but the other thing that you said that that really stuck out to me is like um [55:27] I was just freshman, everyone else was seniors. And I just taught myself AutoCAD, even though I didn't know it. And I think that is such a core entrepreneurial trait that you're so good at. It's just like, I don't know how to do this, but I'll figure it out. It'll be fine. Yeah, I think everybody who's built needs to be down for that. Yeah. [55:46] Yeah. It's kind of a weird, totally unwarnted level of confidence that you shouldn't have, but I don't know. It's just, yeah, you have it too. You have to. Yeah. You kind of have to. Um, and, um,

[56:01] And it's surprisingly, it's surprisingly like, I mean, maybe not, maybe not surprisingly, but it's rare. It's rare to be like, there are no, there's no manual, there's no instructions. And like, I'm pretty behind and I need to like figure this out. And that is actually appealing to me instead of like being so overwhelming and stressful that I don't want to do it. [56:18] Um, [56:19] And I've just, I mean, I've watched you do that like over and over in the work that we've done so far. And it's like, yeah, it's very impressive. [56:28] I think, yeah, just being curious is like such a core part of, I think, being an entrepreneur and, um, [56:37] And, uh, it's hard to be that without, it's hard to be an entrepreneur without having that curiosity because there's just endless problems. Yeah. You have the love problems. Yeah. You can't be intimidated by them. You have to be energized by them. Yeah. Okay. And so you did, so, so you did, you did the photo app. What was the impetus for that? Like, cause that was the first thing that you mentioned that like looks like purely like a business, um, yeah. [57:04] I think... [57:06] I was just sort of like getting, I know that I had like... [57:09] downloaded like a bootleg version of sketch. [57:13] Um, [57:15] And was like, cool, I actually really like graphic design, specifically mobile design. And I had gotten close with it. [57:24] Sharif and Davin, who are both really talented engineers and back then were like Kofsci majors.

[57:32] Thank you. [57:32] And we just were like, we want to do something. And then I think I literally was like, what I like photography, like let's print photos. And that was it. And then we did it. [57:45] Uh, not a lot of thought went into it, but it was, uh, I mean, there's, there's big photo printing apps now. So I think if we stuck with it and knew what we were doing, you know, could have gone somewhere. Honestly, I think like sometimes less thought is better, especially at the beginning. Cause like, it's so easy to just like psych yourself out and convince yourself it's a bad idea and then never do anything. And like the whole point of, at that early stage of doing stuff is not because it's going to be like a huge thing off the bat. [58:15] It's just learning how to like make any kind of business. Like the fact that your aunt used it means that you shipped something, which is like the important thing. Right. We shipped. And that is pretty much exactly how I started Clyde as well. Although I knew at that point that was going to be like a bigger opportunity. Yeah. But yeah, it is important just to be like... [58:34] Thank you. [58:35] Whatever. Let's do it. I have a feeling. Okay. So, and then, so after that, you did, then you did VFA. [58:44] And what was that like? I did VSA, RIP, just shut down actually. I saw that. Yeah. [58:51] Uh, so yeah, I did VFA played a bunch of basketball with Andrew Yang actually, which was like a fun fact. Yeah. He's a really, really good basketball player. [59:00] Um,

[59:02] And yes, I went to go work for this really cool startup out of Columbus called Knockout Concepts. And they were designing and building a 3D scanner. We were a four person team. I think I literally like chose to go work there because they had a really cool office. It's like in a warehouse, they had a ping pong table. And I was like, this technology is cool too. And I really like 3D design. So this is perfect. [59:25] Um, [59:26] And yeah, I was like trying to figure out how to bring this product to market and I [59:32] That meant... [59:33] Shopify, like very basic stuff. We were going to launch it on Shopify. We needed, it was expensive. So we needed like some financing. So we launched a firm. It had a software component that like people needed to pay for. So we integrated with Stripe. And all of this stuff is like on a whiteboard. And we're just like, I'm sort of crossing them off. And then there's an insurance offering. Because we had this idea that like it's a $3,000 product. People will like, they're taking it into like, [1:00:00] underground, you know, [1:00:03] piping gas companies were using it to like skin pipes. We're like, they're going to break it. And we like have no money. So we can't really afford to like replace it. So let's get, you know, offer insurance. Yeah. [1:00:14] And Shopify, Affirm, and Stripe are like these amazing, really simple experiences. And I expected... [1:00:21] an insurance offering to look like that and like did a bunch of Googling, [1:00:25] Didn't, you know, find that. And this is where that like sort of acknowledging problems part of me wasn't yet really built out because I didn't sort of recognize immediately.

[1:00:39] What I just recognized is this is annoying. Now I need to go talk to an insurance company. [1:00:43] Six months later, I sort of got there and was like, these insurance companies are awful. The people there are like... [1:00:50] Not really that enjoyable to work with right now. The experience that they want to give my customers is not going to be good. [1:00:57] There's zero technology when I'm asking them for like API docs or anything. They don't even know what those are. [1:01:02] And that was sort of the beginning of... [1:01:05] There's an affirm version of this. [1:01:09] product. And then the naivete of a 22-year-old that doesn't know much to be like, [1:01:17] And I'm going to solve it and I'm going to build an insurance company. [1:01:21] That's, you know, super privileged to be able to do that and like have the backing of my parents. And I live with my grandma for, you know, a year while building the first version. So very, very lucky to be able to do that. [1:01:33] that. But yeah, it took a while to figure it out. And so, yeah, like what was the like, [1:01:40] Yeah, just give us the high-level elevator pitch of Clyde. Yeah, so Clyde made it possible for any business to launch their own extended warranty program. So if you think about AppleCare, Apple generates an incredible amount of revenue from that. Their customers really appreciate it. They're big. They can convince an insurance company to back the insurance policies that they sell, which they actually do. They don't take on any of the risk.

[1:02:10] you [1:02:12] Now, if your knockout concepts, which was pre-revenue, it's really hard to go to an insurance company and say, hey, you should put in all of this work to back my products. There's no data about the quality of the products and there's no guarantee that that insurance company is going to make any money from it. [1:02:29] What I didn't know at that point was that even like a Dyson, [1:02:33] wouldn't be able to go to an insurance company. Because an insurance company is like, I can launch five programs a year. [1:02:41] Um, [1:02:42] because it takes an army of people at my at the insurance company to launch these programs. So the [1:02:49] Value. [1:02:51] of each program needs to be super, super high. [1:02:54] So what we essentially realized was like, well, why don't we just make it super easy to be able to launch this like a Shopify app or like a couple lines of code? And why don't we build this marketplace of software? [1:03:07] ensures that we can very, very quickly match policies that they've built to products. [1:03:16] So the logic client, it took, you know, it could take 30 seconds if you're like a Shopify app or if you're Dyson. [1:03:24] Unfortunately, it could take a very, very long time, but not because of the development work, just because of bureaucracy. [1:03:32] And it was around the time where you were like building the first version and raising the first money for this that we met. I think you came into Prehype, which is the incubator I was working at. And I was at that point doing some angel investing. And...

[1:03:49] I remember seeing the pitch... [1:03:52] and really liking it. I don't remember, I didn't end up investing, but I don't remember why [1:03:56] Because like my only memory of – [1:04:00] of like the pitch and the aftermath is like, I was really impressed by you. And I was really impressed by the like updates I was getting from you. And I, it was in the category of deals where I was like, [1:04:13] the one that got away or something. I think I just took too long to respond to an email or something. Like you were raising around, it was like closed and you were, and it was like, I kind of just missed it. And then I just felt bad about it. But like, what I remember is, I'm like, [1:04:25] I see a lot of pitches and I, [1:04:28] I think you had this really, really special combination of you were super ambitious. There's a big vision for what you were doing. [1:04:37] I felt like the business was actually like... [1:04:40] really like intellectually like rigorous, like you had really thought through the, the, like the landscape of like why there was a problem here and like how to solve it and stuff like that. But you were also very, um, [1:04:51] Just like straightforward. Like I believed you, you know, like I didn't feel like you were like fucking around in any way. Which is very rare, like to have that combination of like... [1:05:05] Um, yeah, [1:05:06] I'm ambitious and really motivated, but also I'm like pretty straightforward and like, I'm not like... [1:05:13] you know, I'm not putting on airs or whatever, or trying to be something I'm not like, I'm just, am, am, [1:05:18] This is this is what you see is what you get, more or less. And I really liked that.

[1:05:22] Yeah, I mean, when I look back at that time, I just – [1:05:27] It was very, very focused. [1:05:30] It was like, this is the only thing that... [1:05:33] matters right now and like going on dates because I just moved to New York. Um, and I was really excited about that too. Which tell people about your, your dating strategy just really quick. Which one of the, uh, you told me that you would go on like, uh, I think early, early morning dates. Oh yeah. Yeah. I was like, I was very focused on like, if somebody wanted to like get a drink after work, which like I wasn't super into, I'd be like, how about a 7am coffee? And some people [1:06:03] And then my other go-to, which I didn't tell you, was like, sometimes I'd be like, I really want to go to this bathhouse. And do you want to come to this bathhouse? Which I think you've been to. I have. I mean, which one? The one that you still have? Spidey. Oh, Spidey. I've never been to that one. Only one person was down, and it was a really good date. It was super long. [1:06:23] I think that's the spa that either Huberman or Lex Friedman likes. But I've never tried it. Yeah. Okay. [1:06:32] So, yeah, I just remember looking back at the time and being like, it was just so focused on making it work. And it was really complicated because we weren't just building a software product. We also had like these. [1:06:44] pretty big insurance deals that we [1:06:47] needed to close to like launch the business. And I remember being really focused on, um,

[1:06:54] signing, [1:06:56] I, I, [1:06:58] deals that were, um, [1:07:02] What's the word I'm thinking of? I didn't want them to be exclusives. [1:07:07] So like we got a couple offers from these insurance companies that were like, [1:07:11] oh, we're just going to bully this startup and just tell them it's exclusive. And we had to turn them down. And it created all of these unknowns of like, are we going to be able to find a partner? [1:07:22] And I think it's important when you're building, like we had a vision for like a marketplace and we were like, this is going to be better for consumers because it'll just be cheaper and cheaper. And at the time we were kind of like, fuck these insurance companies. Like, [1:07:34] They should be making as little money as possible, which in hindsight, like, doesn't really make sense because they need to make some money. [1:07:43] But we did that and I'm so happy that we did because that became like a core part of our offering and a competitive edge. But it was really, really kind of in those early days need to like. [1:07:54] be able to say no, even though if it potentially jeopardizes what you're building. Yeah, totally. [1:08:01] Why do you think you had the confidence to do that at 23 or 22? To say no to those deals? It just sort of felt like it wouldn't be worth it otherwise, I think. [1:08:15] like we would sort of be stuck [1:08:18] And there, I mean, there were definitely were days when we were considering taking it just cause we needed to go. And, you know, I was making 18 grand a year living with my grandma, um, um, um, um, um,

[1:08:32] And... [1:08:33] And that was after not making anything for a long time. [1:08:38] So, yeah. [1:08:41] I think it was just like, what's the point? Like, this is going to be so hard anyway. We should just try to do it right. [1:08:45] Makes sense. And I guess like, so tell us a story of, of the business. Cause we're, we're starting, yeah, we're starting to get into like the meat. You spent seven years running that business. So you were trying to get into the meat of it. What's, what's the, what's the story? How did it go? [1:09:00] The story of the business. Well, I think it's like actually a bit of a cautionary tale. So we, in, when I was 22, we raised 3 million. [1:09:11] got an office, [1:09:13] Hired like... [1:09:14] maybe we got to 12 people. And we had like, [1:09:19] the product that it was making money and we were growing. And I think that we thought that we had product market fit, but I don't think we understood at the time that, [1:09:30] the litany of challenges that this type of company and this type of product [1:09:35] we're going to encounter, namely [1:09:39] Competition, which didn't exist when we raised, but like existed soon after. Time to value, which is when you close a deal, how quickly like will that business start generating money for you? Because we had a product that people needed to implement. [1:09:58] And then last one is, [1:10:00] Spending money is very...

[1:10:05] It can be dangerous. Like we had money to spend and therefore we spent it and we were encouraged to spend it. So what happened soon after is like we didn't really know all of the dynamics about how the business worked yet we were like finding success with growing our clients. [1:10:23] and growing the number of clients. But soon we needed to raise again. So we raised 14 million. [1:10:30] Um, [1:10:33] And it's this sort of pattern just kept continuing. We raised, we had more money. So we spent the money, we grew our clients, but we, you know, now there was a new dynamic in place, which is like the economy was changing a lot. [1:10:45] Um, [1:10:46] Thank you. [1:10:47] And then same thing happened. We had to raise again. We raised the B and then the economy started tanking. [1:10:58] because the pandemic had just hit. But then everybody got $2,000. [1:11:03] So even though the economy was like kind of not doing well, people were taking that $2,000 and [1:11:11] spending it like crazy. [1:11:13] So we saw our business just totally skyrocket. [1:11:17] Even though what we, I'd say the core problem with our business is, [1:11:24] wasn't changing. And that problem is, [1:11:27] If you close a big deal, it takes a long time to launch that deal. [1:11:31] which is, I think, like a cautionary tale for any B2B business that requires implementation.

[1:11:37] And why is that such a problem? What causes that to make it hard to make the business work? [1:11:43] I'd say there's two different challenges. So the first one is, at a lot of these big retailers, the right hand's not really talking to the left hand. [1:11:52] So you've got... [1:11:54] So these business people that are out like trying to drive revenue or probably compensated on driving revenue, but then you have the technical team that needs to implement. [1:12:03] what the business people have decided to do. And [1:12:07] What we found would happen pretty often is like, [1:12:10] A business person would be psyched about launching Clyde because they were going to make really high... [1:12:15] uh, margin revenue from it. We'd sign the deal. [1:12:19] And then the technical people would be like, who's Clyde? [1:12:24] We're not ready for this. We've got like a bunch of other stuff that we need to work on. [1:12:28] So we'd have to resell again. And there were things that we did in our sales process to try to like, [1:12:33] stop that from happening. [1:12:37] like including technical people in the deal. [1:12:40] or in the sales process. [1:12:45] And then the other challenge is like, I think, especially in retail is it's just a freaking mess. [1:12:51] Like people use different ERPs. These ERPs are really legacy. So like no one there really knows how they work. They're using different, you know, headless software and different e-commerce platforms. And, um, [1:13:04] I think one thing I learned is like, if we had just decided to be the best version of this company only for Shopify, we would have been a more successful business than if we tried to go after every single thing.

[1:13:18] And that, I mean, that's just like a very hard lesson to learn about focus. [1:13:22] Yeah. Like boiling the ocean, like maybe the market size, total market size is bigger, but it's sort of like it's a little deceptive because the divided effort means you don't get as far, even if the TAM is higher. Yeah. And then eventually we we were like, we either need to fundraise or we need to sell. [1:13:42] And we had a bunch of buyers that had come to us and expressed interest. So we ran a sales process, found a buyer, great company called cover genius. It was a competitor out of Australia that was like trying to break into the U S but was kind of struggling, super aggressive sale. And they didn't really have that muscle. And we did. And, [1:14:02] There's a great fit. [1:14:05] And yeah, March 14th, I'll never forget, signed the deal. It was like a couple of weeks after SVB shut down. [1:14:12] Oh my God. Which was a whole other, oh my God, this was like a crazy four weeks. [1:14:18] of selling this business. And what was it like, like, [1:14:21] you know, the moment you signed it? Cause I remember, I remember selling, selling Firefly. I remember that moment. Like, what was it like for you? I mean, I remember signing it and like we were working out of cover genius's office doing, going through diligence and just, it was really collaborative. They were amazing to work with. Um, um, [1:14:39] And I remember sort of like I had our CFO and an accountant there, kind of the guy who would like, [1:14:45] really go through a lot of our data and make sure everything's clean while we were building out the data room. And,

[1:14:51] We... [1:14:53] All hugged. [1:14:55] And and then I went for a walk alone and was just sort of I don't know, I'm like emotional even thinking about it is sort of like this. [1:15:05] I remember that walk feeling simultaneously really freeing of like I had done it. [1:15:11] Thank you. [1:15:12] And also really, um, [1:15:15] Kind of just like, but now, now what? Like, who am I? [1:15:19] And I know that I have, I know that I have like this challenge ahead of me and, um, [1:15:24] Um... [1:15:26] Yeah, it's really emotional. Yeah, I felt that too. And it's such a weird thing because you also feel like you should feel great, you know? Yeah. And there's not really like a playbook for it. Like, I think for a lot of life moments, it's like you graduate high school. Okay, now I'm going to college. You graduate college. It's like, now I get a job. But I think that one of the interesting things about the entrepreneurial path, which is sort of like, [1:15:54] by design, very unstructured is that [1:15:57] when you sell, like there's not that next thing for people. And you just sort of, you can like fall into this like black hole of like, I just lost my identity. I lost the thing I do every day. And like, what now? And there's a, I mean, it is sort of like a cliche thing, but it's also just like, actually just totally real. Like it's very hard. [1:16:15] Oh, I mean, it's like such champagne problems. Like you just sold a company and now you're like, but who am I? And that was also really hard because like what ends up happening is everybody congratulates you and everybody asks what you're building next. And I was like, the way that I described it to this feeling to my friends and to my family was like, I can't hear the music.

[1:16:37] anymore. And like the first thing that I'm going to do is go to try to like hear the music again. [1:16:43] Um, [1:16:45] Yeah. Now I can hear the music though. So, so, but it's been, it's been a journey. [1:16:50] Yeah. So it sounds like you're, um, like a little shell shocked or something like just, you know, a lot of, um, [1:16:57] like going through, like the image I have in my head is like you, someone put you in a, in a dryer on like the, you know, the perm press cycle or whatever. And you were just like tumbling around for a while. And then, [1:17:11] Someone took you out and were like, okay, you're done. Now what? Everything got calm. So Clyde was not a calm business. And then everything all of a sudden got really calm. [1:17:22] And that was an incredible feeling, but it also was like... [1:17:27] It took a solid like three weeks of just decompressing from that state. [1:17:34] where I cried a bunch, I got super sick, like, you know, all these things, it like, I needed to process it. Um, but I totally do it again. I mean, it was like so cool. And I met amazing people and like, I mean, we are doing it again. So that's a really, that's a really good transition into, um, like how you came to every, so you, you'd sold Clyde, you're kind of like trying to list, trying to, um, trying to hear the music again. Um, take us through like how we started working together. [1:18:04] Yeah, so I was... [1:18:06] very similar to you, sort of like,

[1:18:08] stumbling through the desert trying to figure out what I wanted to do next. Um, and, um, [1:18:14] My wife and I did sort of like, I feel like the classic thing that like maybe exited founders do, which is like we moved to Nicaragua and I did a bunch of surfing, which is a really weird saying, but it's true. And it was amazing. [1:18:30] She was working and I was, I sort of like wrapped up my time at Cover Genius and was working. [1:18:38] Thank you. [1:18:39] experimenting with a bunch of new ideas. So I was working again with like Sharif who I built Photon with and [1:18:46] We were... [1:18:47] trying to find problems, which was really... [1:18:52] I [1:18:53] in hindsight, like not a good idea. I just feel like when you're trying to find love, like that's not when you find love. And I think it's the same thing with problems, I guess. But we didn't know that at the time. But one thing that we were really good at and we loved doing was like, [1:19:10] having an idea and then building it super fast. So like, [1:19:13] Figuring out if people were going to use it, trying to get a version in their hands. I got banned from Reddit like 10 times during this period to try to talk to people. [1:19:26] And, uh, [1:19:28] That was like, I just loved that. We didn't come across any idea. And then like his life took him in a different direction. He needed to move somewhere and we just didn't end up.

[1:19:40] This time around didn't end up working out for the two of us. And again, I was sort of like back to the desert, trying to figure out what I wanted to do. And then I got, I've been in every subscriber for a long time. [1:19:54] And I got a article in my inbox. [1:19:59] It was... [1:20:01] Yeah. [1:20:02] It was called Be Sincere, Not Serious. What was it called? Oh, yeah. Well, so that's actually, that was actually something that I got a while ago. I got Be Sincere, Not Serious when I was still running Clyde and that like changed my whole mentality. This was about the billion dollar solopreneur. So like it was a napkin math column about is the billion dollar solopreneur actually even possible? And this was when like Sam Altman and all his poker friends were like [1:20:32] Like, is it actually possible? And Evan basically netted out to like, no, it's not possible. Um... [1:20:39] And, you know, [1:20:41] It sort of was a light bulb moment for me of like, [1:20:44] What about building? I really have liked this sort of like studio aspect of what I've been doing, where I get to like experiment with different ideas and move really quickly. And, um, uh, [1:20:56] I realized two things. One, [1:20:59] Okay. [1:21:00] That doesn't matter if you can build stuff, if you can't get it in people's hands, which I was really, really struggling to do to get people's feedback and then to like get users.

[1:21:10] And every sort of had this unlocked moment of, well, every has that. They already have distribution. [1:21:16] Um, and then I had this other thought of like, [1:21:19] Well, maybe we could get people to build a... [1:21:23] a billion dollar business solo if they just had the right tools. And like, maybe there should be a whole product studio that exists to like, just build those tools to enable the billion dollar solopreneur. I think that's what I wrote in an email to you. You did. So I was like, what's up, Dan? It's been a while. Let's pull up the email. Let's pull up the email. Yeah. [1:21:45] I remember being so psyched to hear back from you and just being like, [1:21:49] I really had this feeling when you responded of like, this might be my future. [1:21:57] Seriously. All right. I've got the email. So what I like about this already is like that subject line, long time, no talk considering my next move. It's like. [1:22:09] I have to open that. Like, come on. Like, who's not going to open that? Yeah. [1:22:16] All right. Hey, Dan, it's been a minute. I just read the one person billion dollar company was inspired to reach out. When we last hang out, we got a drink at Spring Lounge and you were telling me how everyone was just beginning to take off that you needed to take it off Substack and then you went on a few dates with someone and were psyched about them. I can't remember where I was at with Clyde, but it's all blur. [1:22:33] I remember getting drinks at Spring Lounge. That was fun. [1:22:36] Yeah, you were like, you were gushing about this girl. You were like this. I found him. This is amazing.

[1:22:43] Spoiler alert. And I think at the time you were in like peak Clyde stress. You were just like, oh, my God. Oh, really? Yeah. I literally was all a blur. Yeah. [1:22:57] I sold Clyde in March of 23, wrapped up my urn out. [1:23:06] style studio, building smaller profit-driven internet products that could send on their own. It was super fun. And we were off to the races. [1:23:14] Um, but unfortunately he had a big life shift. I'm picking my head up to talk to people from my past that are working on products I love and use regularly. I thought I'd reach out to see what your plans are with every and how I might be able to plug in. I've seen that you're actively building small tools here and there, and I'm wondering what your plans are with them with building more products. For what I can tell, every seems like an amazing platform from which to build out a studio or fund. I'm sure you've thought about this already, but I'm, I'm curious here to hear your take, which I was, I got that email. I was like, fuck yeah, I've been thinking [1:23:44] Uh... [1:23:46] I said, "Very interested in incubating new products at Every, and I have a ton of ideas. I would love to hang." So that was the beginning of it. You had this brainwave. You told me that you were in Nicaragua when you sent this email, right? Yeah. I was in Nicaragua. So I sent that email. [1:24:04] You responded and I was like, this is going to be so much fun if it could work out. And then what I did was I went for a walk on the beach.

[1:24:13] And [1:24:15] That's where I laid out like, [1:24:18] Aye. [1:24:19] these three pillars of... [1:24:22] every that like I thought could exist. And I thought maybe I'd be a good person to run them and like why I would enjoy doing it. Um, I don't know if we want to talk about those. Let's do it. Yeah. Bring them, bring them out. So the first one was like consulting. It just sort of [1:24:39] was like felt obvious to me that a lot of people really respect every and [1:24:45] The business is so knowledgeable on AI and led by you, who has a lot of experience, you know, building companies and being entrepreneurial. And with this sort of addition to me, there's two of those people and that could be pretty powerful. So like maybe we could do consulting. There's this other sort of core idea, which is, well, we should just build more products. We should like build a product studio and maybe the theme could be. [1:25:12] apps software to enable the billion dollar solopreneur um we didn't really land on that but like [1:25:20] The idea was to build a studio and like a profit driven studio. And then the last one, which like we're furthest from, but I'm still think would be amazing. It's like, we should invest in companies because VCs are, [1:25:34] Not all of them are great. [1:25:36] And... [1:25:37] We're two people that have a lot of experience. We understand the journey, the founder journey, I think most importantly. And every just has like clout. So like, I just felt like we could get into any deal that we wanted to get into.

[1:25:51] Um, [1:25:52] So these were the three pillars. I wrote them down in a notion doc. I can't find it. It'll take too long. But I wrote it down and I sort of wrote down why I thought each one would work. [1:26:05] And it kind of is going down exactly like I wrote it, basically. It's going to plan. Which rarely happens. So it's pretty sweet. It's pretty sweet. Honestly, it has felt so... So basically, when we first started talking, there was a little period of like, okay, what's the deal? How are we going to work together? One big thing was like, how are we going to fund this? And we decided like, okay, why don't we just start with some consulting? We'll do some consulting, and then we can use that to fund the studio. [1:26:35] which is like a, it's a risky thing. Like it's hard to start two businesses at once. And that has just ended up working really well. We've been able to do some really awesome consulting work, helping big companies train their, train their people on AI. And also just like know which AI products to buy and, and work with and implement and all that kind of stuff. And it's been, it's been amazing. [1:26:56] And the studio stuff has been incredible. Um, so we've launched, um, two products spiral, um, which helps, uh, helps people automate 80% of their creative work, um, by, uh, basically it's a sort of like a powerful prompt builder. So you can, you make a spiral for me. I use it all the time for this podcast actually to, uh, convert my podcast transcripts into, uh, into tweets, um, and LinkedIn posts. Um, but it's used,

[1:27:24] all over the world by all types of different people. We've got about 4,000 users for that. And then we just yesterday launched Sparkle. [1:27:32] which is an AI file cleaner. So it uses AI to make sure your desktop downloads and documents folders are clean. And that launch was amazing. And it's just been kind of like, I honestly feel like, you know, in Star Wars where like the Millennium Falcon, like they do the like jump to hyperspace and all the like stuff. [1:27:54] the stars like start blurring. Like that's what it has felt like since, since you joined. It's been like really incredible. Like you've just like totally like, [1:28:01] just raised the level of our execution and our pace like dramatically it's been super fun [1:28:07] I mean, I think that like one of the best parts of, you know, [1:28:12] Being here is a quality of person that we have at every is just so high. [1:28:20] So the quality of people that were already here, [1:28:23] Um, and then the quality of people that it seems like we're able to recruit fairly easily is, is such a competitive advantage. And, um, um, [1:28:33] And then also the mentality of the business is build calm businesses. [1:28:39] And if we're I mean, I feel so passionately about this, like if we're not having fun, then what's the point? [1:28:45] And we've so far been able to maintain that. It has only been four months, but it feels like we've done the work of like a couple of years, honestly, which is so exciting. And yeah, it's working.

[1:29:15] sort of turned into is this... [1:29:19] You know, every started as this place where we wanted to make great business writing. And I think we've business and really business and technology writing. And I think we've. [1:29:30] grown and changed a lot in like how we think about doing that. Cause running a media business is like, it's just really hard. It's just really hard to make a good business. And, um, I, what I care most about and I think what everyone at every cares most about is like that create, making that creative playground place where people come to do their best work, um, and building a, building an institution for the kind of writing that we love, um, and, and extending that into podcasts and courses and software and all that kind of stuff. And, um, [1:30:01] What we've kind of figured out as a model for doing this well and doing it sustainably and doing it in a way that, you know, it doesn't end up being like all these media companies that like raise tons of money and then blow up or whatever is... [1:30:16] You can think of it like a pyramid or what we talk about. It's sort of like this pyramid. It's not a pyramid scheme, hopefully, but it's a pyramid. And at the bottom of the pyramid is basically all the writing and the podcasts that we do, the things that we do, the high quality things that we do that are free that get people in the door and get people acquainted with everything. [1:30:39] And then a level above that is the every paid subscription. So that's the $20 a month subscription that we've had since the beginning where we bundle things together. So right now, the every paid subscription subscription,

[1:30:54] incorporates, um, all the writing that we do, um, access to sort of behind the scenes stuff from, from the pod, this podcast, um, discounts on the courses that we run, um, you know, and, and then also access to all the software we build. So there's access to spiral sparkle and Lex, um, and with more coming. [1:31:14] Um, and the idea is like maybe like hundreds of thousands or millions of people interact with our free content and then maybe tens of thousands or hundreds of thousands of people end up, you know, subscribing to the every subscription. [1:31:26] And then a layer above that, we do training, consulting, training. [1:31:32] and courses and, and, [1:31:34] Far fewer people do that, but you pay far more. And then above that is like speaking or advising or other kinds of things which are even more expensive. And even fewer people do that. And that seems to be like a really nice – and we can sort of take the cash from the top of the pyramid and funnel it down into making more writing or building more products or whatever – [1:31:59] And that seems to be like a structure for... [1:32:03] a media company that's really focused on making really high quality stuff that works. And I think it's actually quite counter to what you learn when you're building like a more Silicon Valley style tech business where... [1:32:15] Um, [1:32:18] you know, the recommendation or the thing you're supposed to do is like, focus on a business model and just like, just make that crank that, just make that work. Right. And I think,

[1:32:30] What media companies need to do is you have the core asset you have is sort of like the audience and their relationship with you and the affinity for you and all that kind of stuff. And different members of the audience want different things and can pay different amounts. And you need to have different products for those different people. And what we're trying to do is build a structure that allows us to build different products for the different people that are part of this audience. [1:33:00] It's a big bet. It's a bit different, but it honestly seems like it's working in a way that's like... [1:33:09] I, you know, things almost never work this easily. So I'm almost suspicious, but it's really working. It's pretty great. [1:33:16] Well, I think there's a lot of things that have already been set in motion that are now playing off of each other. And it does all come back to the sort of foundation of this pyramid, which is like every has really high quality content that a lot of people... [1:33:34] read and listen to. And that is the engine behind the whole rest of the business. It just doesn't work without that. And, um, yeah, [1:33:45] And that's also why like to the very first thing that we spoke about, it's like you should be writing and you should be talking and like that's what you're good at and that's what you like to do. And if you didn't do it, like the rest of the business just wouldn't work. [1:33:59] And this is like a model that...

[1:34:02] I feel like it's like very big on Twitter and people are now beginning to realize like, oh, distribution, when intelligence costs zero dollars, basically, like it's distribution that's important. And this is like this new thing that a lot of people are talking about. [1:34:17] We are in a very unique position. [1:34:20] I think where, um, [1:34:22] Bye. [1:34:24] we're actually leveraging that. [1:34:27] And thankfully had every sort of built up before this model became like, [1:34:31] a real concept and we're just sort of cranking it. [1:34:35] Um, [1:34:36] and trying to move really fast on it. It's sort of like... [1:34:40] I mean, you know, the New York, I don't want to compare to the New York Times, but like the New York Times sort of like went backwards into this. They realized that their media business kind of sucks. And then they're like, let's build a bunch of apps. [1:34:52] uh, to like that people really want to interact with and that's bundled it all together. Um, [1:34:58] But they are sort of like a really good... [1:35:03] And a lot of their content isn't free, but some of it is. And they're a really good sort of model model. [1:35:11] I think to base off of. And another thing that they do that's just like, I think a model for us is, [1:35:18] not that we really talk about the New York times ever is their level of quality is just so high. And I think that's really important for both of us is just everything that we put out. We want it to look really good. [1:35:30] work really well and actually have

[1:35:34] Value we're not going to put it out if it's like some bullshit. [1:35:37] Um, which hopefully we can maintain. That would probably be the hardest thing to do. I think so. Yeah. I mean, I think, I think that that's a risk. I think also the risk is like all these different levels of the pyramid, like to some degree have different incentives. And so keeping everything aligned. [1:35:54] um, and supporting each other as things go on is, is also going to be like a really interesting challenge. Um, [1:36:01] But I think one of the things that I really like about Every is – [1:36:06] We haven't raised a lot of money, so... [1:36:09] There's not a lot of external pressure. [1:36:12] And I just love everyone that we work with. I love everyone on the team. It's such a good-feeling team. There's some little magic thing happening right now. [1:36:23] And I just want to keep that going. And I think if we can keep that core group of people together and not... I think we push to move really, really fast. But what we're not doing is... [1:36:37] you know, going and raising a bunch of money or like hiring like 15, 15 people in a week or whatever, like that, that kind of stuff. Um, you know, you talked about, [1:36:45] sort of being calm. And I think like when you're launching as many products as, as we launch, like some, there's definitely some, some stress involved, but like the, there's that sort of like core thing where it's like, [1:36:58] partly we're doing that because it's fun and we do get to set the pace. And, um, and what I don't want to lose is the kind of creative playground. Like we're doing really high quality stuff. Like that's the point of all of this. And, um, I, I think we've got, I think we've got a shot to do it. Cause I think we have a,

[1:37:18] We figured out a structure that works to support it. And I'm psyched about it. Yeah. Speaking of which, if you're a technical founder or you're a technical person that wants to build stuff, you should reach out to Brandon at every.to. Do that. Yeah, we're looking for more entrepreneurs in residence to work with us on some of this stuff. So we're getting close to the end here, but I think we should, obviously in this show, [1:37:48] how people work with AI. Um, but maybe we can show the audience, um, some of the stuff we've been building. Um, I think it'd be really fun. You know, we, we talk a lot about different tools people can use, but one of the things I just have never talked about on the show is like the tools that we build, um, which have come out of problems that we've had. Um, so it's, yeah, I think it's a good, um, I think it'd be great to great to demo it. You want to, you want to demo a spiral? [1:38:18] Uh, and, uh, [1:38:21] I'm looking right now at our team spirals. So is there like the spirals that our team has made and shared with each other? [1:38:28] And so this is one of the spirals to turn a podcast transcript. So like literally a raw transcript into a tweet, which you've used this successfully. [1:38:39] I use it every week. Yeah. Yeah. So, like, I mean, we've created some, like, pretty serious, um, [1:38:46] Yes. [1:38:47] uh, viral tweets. I just know that I I've like tested it with this before. So I know that I just have this, like this, this Google doc, uh, with a pretty good transcript. And this is the episode that I did, uh, with Kevin Roos in the New York times on, um, AI friends. And, and so this is a, this is a workflow that I do every week is I take a transcript and I paste it in there like that.

[1:39:11] Yeah, literally just copy and pasted the entire thing. And now we're going to run it. [1:39:18] Whew. [1:39:19] So it's going to take a second now to like... [1:39:22] basically take this super prompt that we've built and, [1:39:25] with the input, the output, and a bunch of examples that we've trained the spiral on. [1:39:31] Send it to cloud. [1:39:33] And it just returned the output, which is tweet. So, yeah. [1:39:37] On. [1:39:38] Kevin might be the first person to have 18 AI friends. He's a columnist in the New York times, hosted a hard fork part podcast and author of future proof, which by the way, I don't, [1:39:47] One thing that's really cool about Spiral is this actually may not be in the... [1:39:54] transcript, but it uses Claude and it actually knows who Kevin Roos is and like can pull in that information. [1:40:01] Um, [1:40:04] Yeah, his experience was both compelling and repelling. He created AI friends for parenting advice, after checks and was even an even tea time gossip. We dive into I mean, this is just like, it's just really, really concise. It's compelling. [1:40:20] It like captures your attention. [1:40:22] and [1:40:24] It's tight. [1:40:26] And yeah, I mean, the thing is like – [1:40:29] This is also how I write my tweets for my podcast. Like it is... [1:40:32] It is exactly like you. And it's the format that I use. And this is sort of like how it came about too, is like, I, I,

[1:40:41] every week have to do a tweet. And the tweet is like, to some degree, it's like the most important part of the podcast because it's like the thing that most people are going to see. It's how I get distribution. [1:40:53] And that process is like really, um, [1:40:59] It's really boring, but it also requires a lot of skill. [1:41:04] even though it's repetitive. And sometime in like May, I realized that Claude was like good enough at writing to actually do this for me. [1:41:16] Um, but the, the prompt was like super long and like, [1:41:22] Hmm. [1:41:23] you know, just hard for me to do. And I knew no one else was going to do it. Um, but I thought it could be really like helpful for like, not just me, but like anyone on the team. Cause I, [1:41:32] Well, a lot of what you do as a media business is like, and businesses in general do this, is like you're taking creative work or some sort of work in one form and you're like translating into another form. So like we do this as a media company, but like lots of, lots of companies like a B2B SaaS company might take a webinar and turn it into like a LinkedIn post. And that is another thing. It requires a lot of skill, but it's repetitive. [1:41:55] And so I realized Claude could do this. And it was actually on what we mentioned earlier on a think week, which is every quarter we take a think week. We don't do our regular meetings. We don't publish new articles. And it's just a time to let our brains run free and sort of reflect.

[1:42:15] on the last quarter and plan for the next quarter. And I just, in two days, I just like went into a fugue state and like was coding with Claude and like built the, like the first simple version of this, where it was like, you could build a spiral and sort of train it on your own. Uh, for me, it was like training on exam, previous examples of my own writing. Um, [1:42:34] And it like worked after two days and we were looking at it and just like using it internally in the [1:42:41] the writers on our team liked it. And we were like, wow, that could be like, [1:42:45] That could be cool. That could be a product. Yeah. And I think that this is actually a really good time to shout out the – [1:42:52] article that you wrote about Excel. Because, like, you basically did the same exact thing, but, like, instead of Excel, it was Claude. And it was, like, this thing that you kept using Claude for. And you can... I mean, this is what the definition of an AI wrapper is. It's, like... [1:43:06] It's just we're going to add all of this functionality on top of something that you could probably use Claude for, but you just won't. [1:43:13] And there's so many opportunities like that. [1:43:17] I mean, we have another one. It's Sparkle. It's like... [1:43:20] Basically the same thing, that same concept. [1:43:27] So like how long do you think it would take you to write this? [1:43:32] An hour. Because what I'd have to do is like I'd have to rewatch the whole podcast. [1:43:38] and load it into my brain and take notes. And then once I had that, then I could go write the tweet. So it'd take an hour.

[1:43:45] Yeah. [1:43:47] versus what? I don't know. That was like... [1:43:49] Five seconds. And to sort of like explain a little bit more the point you just made about the article I wrote, like – [1:43:59] The thing that I've been seeing and that I think we're kind of keying on for a lot of the products we build is like – [1:44:07] Um, [1:44:08] Excel is this really general purpose tool that taught a lot of... [1:44:15] the world how to use computers. It was like the first killer app for computers is the reason why business people started taking computers seriously. And it's this general purpose tool that [1:44:26] Um, it's really simple to start. Anyone can just type into us into a cell, but it's like, [1:44:32] You can do enormously complex things with it, but its complexity and its power is progressively revealed as you get deeper and deeper into it. And it started off being a tool for obviously doing financial planning, basically, or forecasts or whatever for businesses. Yeah. [1:44:51] Over time, because it's so general, it just got adopted by lots and lots of different businesses to do lots and lots of different things that it was never maybe really intended for. People were using it as a CRM or a to-do list or keeping track of business processes and all this kind of stuff. [1:45:09] And I think Excel really created the sort of B2B SaaS wave because once people were

[1:45:17] trained on using Excel as a tool and the idea that they could use computers to do all these tasks, they created workflows inside of Excel that were like, [1:45:26] really custom for their like specific, um, [1:45:30] specific use case that Excel just wasn't that good at covering. [1:45:37] And, and I'm not the first person to say this, like this is, uh, I'm, I'm taking this from this guy, Tom Tungus, who's a, uh, I think he used to be an investor at Redpoint and I think he's at another fund now, but he's super, super smart, really great writer. And, um, yeah. [1:45:51] So Excel progressively got unbundled over the next 20 years into – [1:45:56] all these different SAS products. Um, and it's still around, obviously Excel is super, you know, a super important tool that is one of the most widely used pieces of software ever. Um, but it also got fragmented and all these other purpose specific tools. And I think chat GPT and Claude are the same basically like, and I, and I, the same for a new generation of computer users. Um, there are, uh, incredibly powerful tools. That's really easy to get started. They're incredibly, um, [1:46:22] uh, general purpose. And I think, um, [1:46:26] They are training people to learn what AI is useful for and how to use it. And as those people get more and more used to it, they will find more and more problems that would be better solved by a specific tool rather than a general purpose tool. And I think Spiral is a really good example of that where...

[1:46:48] I think Spiral only works as a product because people are used to using AI enough or the people who use it are used to using AI enough. They realize that, yeah, I can like prompt people. [1:47:01] Claude to do this, but like it's a pain in the ass. And and so they immediately sort of recognize like, oh, having a purpose specific tool for this is really good. And there's this like expanding horizon of people who are starting to get used to AI enough that they want a tool for something like this. I actually I actually wonder. So I have a bit of a different take. [1:47:25] And I wonder if it actually unlocks... [1:47:28] the power of AI for all of these people that actually wouldn't go to Claude to do that. Because now they have, like, one of the problems with Claude and Chai GPT is, like, [1:47:41] It's like the way that you interact with it is it is literally just like a chat function. [1:47:46] And it's sort of that same issue that we described earlier, which is if you're not in a box, you don't really know how to use the thing or like how to be creative. And like, that is the definition of like, not in a box. You could like do literally anything with it. So I almost wonder like, [1:48:01] It's this purpose-driven thing that's supposed to do... [1:48:05] really one thing for you? And does that make it more accessible to all the people that actually wouldn't go to? Yeah. [1:48:13] And maybe that's not the case right now. Maybe a lot of our early users are fans of every site. They are using AI anyway, but I actually think that it's the...

[1:48:24] It's sort of the unlock for all of those people that don't use AI. [1:48:28] to start using it. I think you're totally right in the sense that it is... [1:48:33] Um, it's, it's easy enough to use that people who don't use AI can use it and, and will get a lot of value out of it. But I think that those people are typically not searching for this tool because they don't know it's even possible or that it exists. And I think the people who are like looking for this as a solution are the people who like know it's possible, but know it's hard. And those are people who have already adopted these tools, but like are not, um, um, [1:49:00] uh, who, who already adopt these tools, but are not satisfied with the quality level that they're getting or the ease of use that they're getting or the power they're getting from the general purpose tools. And I think those people become the early adopters of products like this. And then yes, once they've adopted it, then they can spread it to their colleagues, for example, who like would never even like think to search for something like this. And maybe their colleagues skip from like, they don't even have a phase where they're using cloud. They're just using something like this. And maybe this is the gateway for them to be like, Whoa, maybe I should use [1:49:30] I could use it for lots of other things too, in addition to this specific thing. So I agree. I think it's a little bit more complicated than that, but the early adopters are the people who know that there's a problem because they've been using... [1:49:42] Claude for this and are like, I think there's something better to be had here. [1:49:46] Um, [1:49:47] I think that's right. And I think you definitely actually see that with Sparkle. [1:49:53] Because so sparkle is a product that we launched yesterday. It cleans your computer for you or organizes your computer for you. And I think that what we're describing right now is definitely the case for that because, um,

[1:50:04] The risk that you take with signing up for Spiral is that you've just created a new account for something, and that's very low risk. The risk for Sparkle is that you're allowing AI to organize your computer, which means moving files around, and that's scary. [1:50:24] And I think you can actually see that. We both thought Sparkle was going to be a bigger launch than Spiral. It turned out to be a smaller launch than Spiral, but I don't think that we realized just like... [1:50:37] how invasive actually of a product is. [1:50:40] It really is. [1:50:42] It's not actually because it can't delete your files. It's super easy to undo it. But... [1:50:49] Mentally, that's very real. Yeah. Well, let's see your desktop. Here's my desktop. That's pretty clean, man. It's pretty clean. Doesn't it feel like a breath of fresh air? Every time I look at it. [1:51:03] And that's Sparkle. So go back to your desktop for a sec. Show us the organization scheme that you have. [1:51:11] All right, so I've got Recents, which is obviously a lot of screenshots and some data. So anything that I downloaded or anything that I added to my desktop today gets put into Recents, and it stays here for three days. So any file that you recently add to a folder stays there for three days, stays in Recents.

[1:51:36] Um, [1:51:37] The manual library is like this place that you can use to, if you don't want Sparkle to organize your computer, organize these folders. So if I'm like, all right, my taxes are really important and I do a good job of organizing them. I'm going to create a folder in manual library and then just organize a [1:51:55] my taxes manually. [1:51:57] And the other thing that Sparkle does is if you already have a bunch of folders on your computer, we'll automatically put them in a manual library so we don't mess with those. And then AI library is like this magical place where... [1:52:13] I have had thousands of files on my desktop, and now they're just magically organized. [1:52:19] in my AI library. So I've, you know, been dogfooding, uh, uh, sparkle for months and I've had countless experiences of needing to find something that's like really obscure opening up my library and, uh, being able to find it super quickly. Um, [1:52:39] So I was pretty sick. [1:52:42] It's definitely, I mean, I find it super effective for desktop and especially for downloads. [1:52:47] Um, [1:52:50] Thank you. [1:52:51] Yeah, it's pretty amazing. It's great. And yeah, I'm one of those people where it's just like, [1:52:56] that [1:52:58] So everything's a mess for me. And that's one of the things I've been so... I mean, that's why... One of the reasons I got into productivity originally is I'm just bad at organizing stuff. And so that's why I started Super Organizers because I was like, I want to learn how to do this. It's like sometimes you turn your weakest trait into a skill or a thing that you're obsessed with because you're bad at it.

[1:53:22] Um, and I actually, like I built the first version of, of sparkle like four years ago. Um, and, [1:53:29] for that, for that purpose, but it was all manual. Um, and, uh, uh, and I used Tiago Fortes. He has this system called para. I use para to like, as the, as the base organizational system, which by the way, he uses sparkle now, which I feel like is the ultimate vote of confidence. Like he is the, he is the organization guy and now he uses sparkle to organize. He, he at least tweeted it. I'm not sure. I'm not sure whether he uses it. He might or might not, [1:53:59] That's true. I'll say that. That's true. Yeah. [1:54:02] And, um, [1:54:04] And when all the AI stuff started happening, I was kind of like, well, maybe it would be cool to... [1:54:10] like just redo it with AI organization. And that was the first project we decided to work on together. And you sort of took it and ran with it. And I mean, I think you guys rebuilt it from the ground up. You've been working with Javi, one of the developers we work with. And I mean, it's one of those products where... [1:54:31] Um, once you install it, you don't have to think about it ever again, but you feel it every day that when you use your computer. And I love that. It's such a good feeling. [1:54:39] Yeah, I mean, that is a special type of product that you don't actually need to engage with it for it to deliver value to you. And that is like, I think something that we will continue to do. [1:54:51] try to search for in the products that we build.

[1:54:54] So this has been an incredible episode. I'm so glad that we did this. Um, [1:54:59] So we're getting close to time, but I think we'll definitely keep doing this regularly. We want to keep people updated on what we're building and how we're doing. We're kind of like discovering a new model as we go. And so you'll definitely be back. And thanks so much for coming on. Like, this is honestly, this is so much fun. I feel very, very lucky to get to get to do this with you. [1:55:20] Yeah, likewise. It's bringing me back to my radio days of college. You're good at it, man. I can tell you're a radio guy. Yeah. Thank you for having me here. This is cool. Of course. [1:55:32] All right. See ya. [1:55:34] See ya. [1:56:04] that will leave you on the edge of your seat. [1:56:06] craving for more it's not just a show it's a journey into the future with dan shipper as the captain of the spaceship [1:56:14] So do yourself a favor. Hit like, smash subscribe and strap in for the ride of your life. [1:56:19] And now, without any further ado, let me just say, Dan, I'm absolutely hopelessly in love with you.