Transcript: ‘Building an AI Media and Software Empire’

The transcript of AI & I with Brandon Gell is below.

Timestamps

1. Introduction: 00:00:56
2. Dan’s childhood dream—to build a Microsoft competitor: 00:03:36
3. The first app Dan built in middle school: 00:07:07
4. The story of Dan’s first company that he sold in college: 00:18:52
5. How Every came to be: 00:33:56
6. The start of Brandon’s journey as a builder: 00:49:15
7. Brandon’s first software app—and why you should launch first, and iterate later: 00:57:05
8. Everything Brandon learned from running a B2B business for seven years: 01:08:49
9. What brought Brandon to Every—and the email he sent Dan before joining: 01:18:00
10. Every’s master plan to be a successful creator-run business: 01:29:15 
11. Live demo of Spiral, the app that automates 80 percent of repetitive creative work: 01:38:11
12. Brandon and Dan’s take on how AI startups can find a valuable niche: 01:44:00
13. Live demo of Sparkle, the app that organizes your files for you: 01:50:52

Transcript

Dan Shipper (00:00:57)

Brandon, welcome to the show. 

Brandon Gell (00:00:58)

Thanks, Dan. Thanks for having me.

Dan Shipper (00:01:00)

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 tech technology company called Clyde about seven or eight years ago—you raised about $50 million. You had 100 employees. You sold it in March, right?

Brandon Gell (00:01:21)

Yeah. March 14.

Dan Shipper (00:01:22)

You sold it in March and then you joined Every and it’s been kind of an 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 everybody generally, talk about our relationship, because there’s just a lot of cool stuff going on.

Brandon Gell (00:01:45)

Yeah, we surprisingly go pretty far back, actually. But, yeah, this has been kind of a dream come true for me, honestly. I’ve watched you go from Superorganizers to whatEver is today. And just having this creative playground has been an amazing opportunity.

Dan Shipper (00:02:08)

I love it. I love it. So, I think the way we’ll structure this— This a little bit of a nontraditional AI & I interview because 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 lay out Every, what it is, the background is, how we got to where we are today, and then I’ll turn the tables back to you and you’ll talk about some of the product work we’ve been doing, and demo some of the things we built.

Brandon Gell (00:02:42)

Yeah. Honestly, before even getting into where Every started, I feel like nobody actually really knows who Dan Shipper is, and the fact that you’re this technical prodigy. And actually I don’t even know if people know that you’re really technical and build stuff, let alone sold a company at—whatever—14. So I feel like you should just give me the— I don’t even know the full story, but I know you started a company in college, so maybe we start there.

Dan Shipper (00:03:16)

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 gonna 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. 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. 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 1. Write softly.” I didn’t even finish software. Just write soft. Step 2.—

Brandon Gell (00:04:15)

“Write soft.” This was just— You wrote that in the notebook and it was just “write soft.”

Dan Shipper (00:04:19)

Yeah “Write soft.” Because I was going to build an alternative to Windows. That was my goal. So I was doing the plan. So write soft and then “Burn it to CDs,” because it was— I don’t know if you remember— Do you remember the days when, in every grocery store, you could get a little AOL disc and then you would install it. So, I wanted to do that. And then the third step was “Distribute mailboxes.” Which makes sense. 

Brandon Gell (00:04:54)

Sure. You’re following a set game plan here that’s been successful. It was really successful until it wasn’t.

Dan Shipper (00:04:59)

Yeah. “Distribute to mailboxes,” and then the last step was “Wait.” And that was my whole strategy. But that’s basically why I learned to code. Because I wanted to build this Microsoft competitor. And I made my dad go out and buy me a book on BASIC, the programming language. And I was sort of off to the races from there. I quickly realized that I was not going to build a Microsoft competitor, but I kept doing it because I was always interested in building businesses and being technical. At that point, it was the only way that I could build a business where the only cost was my time. So, as a middle schooler, it empowered me to build businesses where I could actually make money. And I thought that was the coolest thing ever.

Brandon Gell (00:05:45)

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. I don’t even know what I was doing. I was like—

Dan Shipper (00:05:59)

Yeah, what were you doing in middle school?

Brandon Gell (00:06:00)

I was tossing a Frisbee somewhere. I was a very sporty kid.

Dan Shipper (00:06:07)

Yeah. See, I was not athletic at all, which may have helped me get into being technical because otherwise I would have been outside with friends.

Brandon Gell (00:06:16)

Yeah. I don’t know about friends, but I was playing sports. And also 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, but we do do something at Every called “Think Week” once a quarter and I know that— And, I mean, I actually didn’t know when I started here that that’s what Bill Gates used to call it when he would run away to a cabin. So, there’s still that through line. He’s still inspiring some stuff here.

Dan Shipper (00:06:48)

Yeah. Still Gates-inspired. Have not unseated Windows yet, but there’s still time.

Brandon Gell (00:06:54)

Totally. Yeah. Our next incubation.

Dan Shipper (00:06:54)

I think the next kind of stop on the trajectory is: 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, I started noticing that smartphones were becoming a thing. So, 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 was before the iPhone came out, so there was no word app. It was just like BlackBerry software. And so, the first piece of software that I built was called FindIt. And basically I kept losing my BlackBerry in my house and it would be on silent and I couldn’t make it ring. So, FindIt 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. And if you sent that email, your BlackBerry would ring, even if it was on silent, which I thought was the coolest thing ever. And I eventually sort of iterated that—it had a full-fledged web interface, you could track your phone on a map, you could lock it, you could back it up, you could make it call you, which was kind of a cool feature. And I had like a bunch of customers. It wasn’t a huge business or anything, but it’s how I paid for gas and food in high school. And I think what’s really funny about that story is it was a one-time purchase. So, it was like $10 or $20 bucks forever instead of being SaaS because Stripe didn’t exist. So, it was way-too-hard to build subscription software. And yeah, I would have had a lot more money if Stripe had existed when I was in high school.

Brandon Gell (00:08:56)

That’s coming back, that form of paying for software, so maybe you were just really, really early to that trend. Well, I think that’s— One thing that’s been really cool working with you is I just think that being able to identify problems is actually really hard. Not because there’s 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 vs. just your experience—your lived experience. And I feel like that’s something that I know that you’re really good at, and it turns out you’ve been— It’s a muscle and you’ve just been working on that muscle for a very long time. It’s certainly a muscle that I’m still pretty early-stage and I sort of feel like a lot of the ideas that I sort of fall into vs. I feel like you have a bit of a practiced refined muscle of even identifying, okay, this 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.

Dan Shipper (00:10:15)

Thank you. I really appreciate that. That means a lot. I’ve not really thought about the problem identifying muscle, but it definitely is a muscle. I mean, maybe it’s partly my Jewish neuroticism. I’m just constantly complaining about things so I can see the problems. But yeah, it’s been something that I’ve been doing for a while. And I actually just love looking at the world in that way. Because it makes me sort of 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 the world and see problems and be, but we’re empowered to fix them. And that always makes me really excited. Because I’m like, ooh, there’s something new to do. I have a new project to do, you know?

Brandon Gell (00:11:03)

Right. There’s also a difference between– So it’s 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 so, I studied architecture in college and what I got really good at was being put into a box. It’s like, hey, here’s a building that we need to renovate or here’s a space that we need to put a building on. And here’s the box. And now we can think about all of these interesting ways to solve the problem within the box. But we never really were like, hey, go out and try to figure out what the box even is, because then you’re just looking at the whole world and its sort of infinite possibilities. And it’s really quite hard to define a box.

Dan Shipper (00:11:47)

I think you’re totally right. And I think that’s, in general, one of the things that school doesn’t give you. And I’m kind of happy that I didn’t spend a lot of time doing side projects and stuff as a kid because I had to define the box because at that point there were no there— You couldn’t even take a computer science class. There are no real business classes for kids, 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 that’s another skill— That’s really interesting that you feel that way about architecture. One of the things that I think is really cool about architecture programs and people who have studied architecture is it’s a very multidisciplinary thing. It’s sort of halfway between art and engineering. And I feel like you kind of incorporate that in the way that you think in the way that you build products and stuff like that. How has that sort of affected the way you look at the world?

Brandon Gell (00:12:39)

I think the biggest thing that I learned through architecture is just being iterative and not getting stuck on a solution. And, I was the type of kid growing up that would— If I had to write a paper, I’m writing one at a time and I’m not even editing it. I just wrote it and submitted 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 if that’s how I operate. My first design is going to be the worst—or the best. I won’t know until I throw a bunch of stuff at the wall. And it would be a big mistake to try to get caught—or to get stuck—on what my first solution is. So just being comfortable, iterating a lot is probably the best thing I got from architecture and then being able to take critiques—a lot of criticism in architecture.

Dan Shipper (00:13:44)

Isn’t architecture school really intense? They’re yelling at you a lot and there’s late nights and stuff, right? Or am I wrong?

Brandon Gell (00:13:55)

Yeah, there’s a lot of studio time. I also went to Middlebury, a liberal arts architecture school, which was kind of a bit of a janky version of architecture. I wanted to be an industrial designer, so it was sort of a path to do that. But yeah, it was still pretty hard. And a lot of feedback—definitely.

Dan Shipper (00:14:15)

So the thing I’m kind of keying on, and the thing I’m interested in on the iteration front is: How are you taught to do that? Are they just telling you you have to do a lot—a lot of these things—or, what is the process by which you just learn to iterate?

Brandon Gell (00:14:32)

It’s all sketching. It’s just a lot of sketching. And, I really like computers and I was, from a very young age teaching myself video editing software and all types of video effects software and a ton of 3-D software and rendering software. And then I was like, great, I’ll go to architecture school and be able to use that. And that’ll be so much fun. So, freshman year, we had a project and it was immediately brought up on my computer and was like, great. I’m going to start rendering something and my teacher was just like, this is not what we do. You’re going to spend the next quarter just sketching and drawing and I sucked at drawing. So it’s just building muscle constantly. Looking at the world eyes wide open and being able to see interesting things, process those interesting things, draw them, take pictures of them, sort of store them away and then keep going forward. And not getting stuck on them because 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 inspirations that you’ve sort of pushed together. And when you get stuck on something, it’s impossible to come up with something new. You’re just going to end up coming up with a derivative of that thing that you’re stuck on. So for me, it was just a ton of drawing and building the muscle of being able to let stuff go, flip the page, go for a walk, try to think about the next thing.

Dan Shipper (00:15:15)

I love that. I think it really also connects back to the thing you were talking about. For me, seeing the problems to solve, it helps you look at the world in a certain way. And I think that that’s always the start to doing really great creative work.

Brandon Gell (00:16:32)

Yeah. And you’re actually really good at that. A lot of times I’ll see you go for a walk— And you’ve told that story of just talking to ChatGPT and using it as a recording device, but one that gives you feedback and that’s a pretty amazing way to let stuff go and then process through your stuff. I do want to go back to the fact that you started a company in college and talk a little bit about that. And maybe you could go off on what that was like.

Dan Shipper (00:17:00)

Totally. So basically, by the time I got to college I had built this first company. It was called— I mean, it wasn’t a company, but it was a little business called Convenience Software and I had all these different apps or whatever. And then when I got to college that’s when it was— In 2010 is when I got to college. And that was 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 had just started. I actually had John Collison, the one of Stripe’s co-founders, who needed to get a visa to stay in the U.S. and so he needed to do speaking engagements to show that he was legit enough to stay. And so he came to Penn, and I brought him to Penn, and he came and spoke to us and we went to dinner with him and all that kind of stuff. It was really awesome.

Brandon Gell (00:18:02)

Why has he not been on the podcast? You made Stripe possible, basically.

Dan Shipper (00:18:06)

John, if you’re listening— No, I mean he used to try to— Actually we kept in touch. He asked me to join Stripe a couple of times, which I said no to, which was probably one of the biggest mistakes of my career. Now that he’s a billionaire, he doesn’t return my emails. So John, if you’re listening, I love you, come back into my life. We’ll have you on. I would love to learn how you use ChatGPT.

Brandon Gell (00:18:32)

I mean, he owes you. Basically.

Dan Shipper (00:18:34)

He does. Yeah. I should frame it that way.

Brandon Gell (00:18:36)

Yeah, he does. Anyway, he’s a good guy.

Dan Shipper (00:18:42)

He’s a good guy. Yes, So anyway, I just did a bunch of projects. I was working with a couple of different friends doing a lot of different things. But then, in my sophomore year, I decided I really wanted to focus on building B2B software. Because I was like, I want to learn how to build a real business. I want to learn how to build something that makes money from day one that I can grow from school that I can mostly bootstrap—all that kind of stuff. And I was on the phone with my dad and he was complaining to me. So, when you complain, it’s a good way to find startup ideas. He was complaining to me about— So, he runs 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—cemeteries and stuff like that. And he really wanted something where if he was on the phone, he was talking about a diagram that he had up on his computer and the person on the other end also had the diagram up. He wanted a grid to come down from the top of his computer screen, sort of like a battleship and be able to say, okay, look at cell E5, or whatever. And he was like, can you build that for me? And I was like, dad, that’s dumb. That’s a stupid idea. And–

Brandon Gell (00:20:07)

That’s how most great ideas start, I feel like.

Dan Shipper (00:20:10)

But I told that to the people who ended up being my two co-founders at Firefly, which is the company that I started in college. And they actually built the first version of that at a hackathon at PennApps. We were working together on another SaaS product at the time. 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. So it was like, you could put like a banner ad in your email and companies would have their employees put it in and advertise their products or whatever. And we’re like, I don’t know, it’s hard to sell email signature marketing products. Why don’t we just like to try this one?

Brandon Gell (00:21:08)

Right. You got a buyer.

Dan Shipper (00:21:10)

Exactly. That’s the first thing where you’re like, oh wow, this is really cool. What’s funny is they just let us on for six months and never actually bought it.

Brandon Gell (00:21:20)

Classic SaaS B2B buyer.

Dan Shipper (00:21:28)

Yeah. I had a lot to learn. And so we took a summer just renting a little apartment in Philly. And we worked on this product. And by the end of the summer, we had a really well functioning product. The product, that technology we built, is called co-browsing and co-browsing is sort of like screen-sharing, but 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. It’s all JavaScript based. And it’s cross-platform. So you could be on a PC or a Mac or an iPad or whatever. And we’ve applied the technology to customer service. So if a customer is having a problem with the website, we allow the agent to— Basically whoever they’re talking to on the phone or over chat to basically look over their shoulder, see what they’re doing on the website in real time and help them through the site in real time. And it was a very, very cool technology. And it was incredibly hard to build. It’s very, very difficult to make it work cross-platform and cross-browser and with any kind of update or whatever. And it had to work back to Internet Explorer 8. So I can’t even tell you the late nights that I spent with my co-founders, trying to fix some random bug in IE8 and on some customer’s website. Truly traumatic. But we basically ran that business for a couple of years, got a bunch of customers, got a bunch of traction, especially for where we were. Because we didn’t take any money. We raised $20,000 in total from the Dorm Room Fund, which is a first round capitals— We were the first investment of the 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 and they wanted— But it’s a five- or 10-year sales process for them that takes it to a $10 or $50 million sale. And they wanted a cloud solution that they could sort of sell as a tip of the spear into those companies.

Brandon Gell (00:23:42)

And how old are you when, when they approach you and say, we want to buy this?

Dan Shipper (00:23:46)

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.

Brandon Gell (00:23:57)

And put us in that room. You’re 22, you know nothing, basically. I mean, I started my company at 22 and I knew nothing. So, you knew a little bit more than me, but relatively nothing. And so, you’re in that room. I assume you had a lawyer.

Dan Shipper (00:24:15)

I mean, we definitely had a lawyer during the negotiations. I’m thinking about, yeah, I mean, honestly, I haven’t thought about this in a long time. But it was basically the way it all happened is part of the way we got traction for the business. 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 an OEM into other big platforms. And basically what had happened is we were working with a couple of partners and one of them was like, hey why don’t we just buy you? Because, we want this as part of the platform. Instead of integrating, I wanted to just buy the company outright. And that was a really big live chat customer service company. And we kind of went through the diligence process with them, which was like, freaking— It was wild. I remember—

Brandon Gell (00:25:25)

You’re in college at this point, going through finals and stuff. Did you even care about schoolwork? Or is it nothing compared to, I’m selling a company right now. This is crazy.

Dan Shipper (00:25:36)

I did. I like school. I majored in philosophy. And I wanted to be really well read. And so the really fun part of majoring in philosophy is you just read tons of books. And I actually thought there was a lot of overlap between philosophy stuff and entrepreneurship stuff. Because at the time, the big methodology for starting companies was the lean startup, which is a startup is like science. And, for example, some of the things that I was 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 hypothesis testing or whatever, then you’re like, oh wait, but how does science actually work? We should take that metaphor really seriously. And then you’re like, well, then you’re just reading—

Brandon Gell (00:26:21)

For the listeners out there, Dan reads the hardest books to understand that are simultaneously super interesting and so boring and he just loves them.

Dan Shipper (00:26:35)

I do. It’s my happy place to read extremely boring, extremely fancy books for some reason.

Brandon Gell (00:26:39)

This is my nightmare.

Dan Shipper (00:26:44)

I know.

Brandon Gell (00:26:48)

If I’m not reading a Three Body Problem-style book, it’s like—

Dan Shipper (00:26:52)

Look, I’m just taking one for the team, you know. I read it so other people don’t have to.

Brandon Gell (00:26:55)

Yeah, definitely. Someone’s got to read them.

Dan Shipper (00:26:57)

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, you know, the glass that’s electrified, so it gets frosted automatically when you go in and then it defrosts itself. So I was in one of those and the head of a biz dev guy came in and he’s just a really intimidating, intense Israeli dude who rides a Harley and he plugs his laptop in and I’m trying to remember the exact words, but he had his Evernote up by accident. And I can’t remember the exact words, but it was like something like “be aggressive, letting them know that we have other options.” It was something like that. Tell them that they suck and that we have other options.

Brandon Gell (00:28:04)

Right. Yeah. Bully the college kid that you’re trying to buy the company from.

Dan Shipper (00:28:08)

Actually, looking back on that, he was probably in his 30s or 40s and yeah, we were 22. That’s pretty fucked up.

Brandon Gell (00:28:15)

Yeah. That’s kind of, I mean— Anyway, you didn’t get acquired by them.

Dan Shipper (00:28:23)

Well, basically we were in the process of getting acquired by them. So we were going through the diligence, even though he was kind of a dick a little bit. They were really pressing us. We were going through diligence. And 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. And they were like, oh well, maybe we would buy you. And so then we have a little bit of an auction going. And so we went through the process with Pega and they were on it. They were just so— Everyone there was really, really nice. And they took us really seriously, even though we were super young, which, looking back, I deeply, deeply appreciate. And they kept all their promises, which were really great. And so what that allowed us to do is we were negotiating with Pega and we got into a range, like a number that we thought was reasonable with them. And so we went back to this other company and we were like, the price just tripled—just to see if we could get a lot of money for it. And basically they were like, no. And so we ended up getting acquired by Pega, but it was a fun ride.

Brandon Gell (00:29:46)

What an amazing experience at 22. I mean, I went through a similar experience at 28 and I mean, I’ve really, really— Selling a company is very hard, it doesn’t matter how good your company is. It’s really, really hard to do and to do it at 22 is pretty wild to go through that.

Dan Shipper (00:30:08)

Thank you. Yeah, it’s hard. It’s distracting. It’s just so emotional. It takes such an emotional investment to do that. It’s just hard to focus on your work.

Brandon Gell (00:30:22)

Yeah. I mean, I have an anecdote from when I sold my company. My good friend— I was so wrapped up in Clyde and what we were building and making sure that it was trying to be successful. And it was like, I became who I was for better, for worse—kind of necessary to make it successful. But also not great. And I remember my friend Thomas threw dinner for me. It was a surprise dinner, two weeks later. And my sister was there. My wife was there, a bunch of people. And I stood up to give a toast to them for being supportive. And I just started bawling. I couldn’t get it out. And then I was like, alright, I’ll like to take a breather and I’ll try it again in 20 minutes. Stood up again to make the toast, and just started bawling again. I couldn’t do it. And yeah, I mean, I was like, 28 and had more life experience than you had at 22. And I don’t think it gets easier. You know, I think if you’re really building something, you get really, really caught up in it. And it’s hard no matter what to say goodbye to, it’s like a part of who you are.

Dan Shipper (00:31:40)

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. I was holding my shit together and then I started having panic attacks after it was done.

Brandon Gell (00:31:54)

Oh, so a week after I sold Clyde, I got extremely sick and I was like, oh, I guess it’s possible to just get sick from stress or something. But yeah, I mean, another sort of— 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 Lydia, my wife at one point during Clyde, and I was just like, I don’t know how— I feel really weird right now. And, I’m uncomfortable and I can’t turn my brain off and I don’t know what’s happening to me. And she stopped walking and put her hands on my shoulders and was like, this is called anxiety. And it was such an eye opening moment for me. I was like, shit, I guess I do feel that—it’s really hard.

Dan Shipper (00:32:51)

I think people should know for context that your wife is a therapist.

Brandon Gell (00:33:00)

True. Yeah. But I don’t think it was hard to tell. I just couldn’t tell.

Dan Shipper (00:33:02)

I had that too. I mean, I didn’t know about any of this stuff until I literally stopped being able to breathe 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, if you’re a founder, kind of running toward the pain or running towards the stress or whatever. And, I mean, to some degree it’s exciting to 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 gets to be too much.

Brandon Gell (00:33:35)

Actually, I think this is a very good segue to Every and how Every started, why you wanted to build what was originally Superorganizers. I think both what it was, and then also why did you want to build it?

Dan Shipper (00:33:56)

Yeah. Really, really, really good question. So basically I ran the Firefly business inside of Pega for a couple of years. And then I left in 2016-ish. And I spent almost four years just wandering the desert, proverbially. So, I wrote a novel. I did some angel investing. I worked at an incubator called Prehype. And basically in 2019-ish, I was like, okay, I think I just want to start another company. I’ve tried a lot of other things and I really like starting companies. I’m going to do that. And I wanted to start a tools-for-thought kind of business, like Roam or Notion, a note-taking kind of a company. And I was like, how am I going to do that? Because I had a bunch of ideas for how to do it. And what I wanted to start with was instead of starting with my ideas, I wanted to do customer interviews with people to try to understand how they were taking notes, especially really interesting people. And then try to build a product around that. And so I was like, oh, what I’ll do is I’ll start a newsletter. 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. And then I’ll take what I learn, I’ll write the newsletter because I love writing, 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 love of writing that I’ve had for forever and my sort of love of business and building stuff. And I got really interested at the time in building business newsletters and the idea that people would pay a subscription fee for them. Because it was like at the very beginning of the Substack-creator economy wave. And so I started working with my co-founder, Nathan, who—We’d been friends with for a really long time. He was the first employee at Substack and we sort of together came up with this idea to build a media company for this new internet age, this new sort of Substack-y creator economy age, where what we saw is a.) There is this movement of people unbundling from traditional publications and starting their own Substacks. But b.) that had a lot of drawbacks. So they’re sort of trading— They’re getting a lot of upside, so if you make it, you can make a lot of money, you have a really good business. Ben Thompson probably makes $3 million a year cash or something like that. It’s crazy. And it’s all profit. And but what you trade is you kind of lose a lot of the camaraderie. You lose a lot of the editorial support. You’re running a business by yourself. That’s a lot. And it’s lonely.

Brandon Gell (00:37:13)

Especially for a creative business.

Dan Shipper (00:37:15)

Exactly. And you can’t take a break. You have to write every week. There’s no vacation. So that’s actually really hard. And very few people can actually do that. And also the 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 that really big longform piece or whatever. And then for all readers, they have to pay individually for each writer. So that’s just not as economical as just paying for a publication that has a lot of writers inside of it. And so we were like, what if we built a bundle of business newsletters and we tried to create 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 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, we had this whole system for calculating how much bundle revenue you would get. So if you attracted more readers you would make more upside. But we also had a lot of the benefits of building together. So we had a Discord and we had an editor and we were all kind of working together to make each other better. And so that was like the original impetus for Every and we started bundling in writers.

Brandon Gell (00:38:50)

Like a collective-y type.

Dan Shipper (00:38:52)

Exactly. So we called it a writer collective. And so, to kind of tie it back to my previous experiences, I had just gone through this thing with my previous company where 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, it’s not my life’s work or whatever. And what I really wanted to try to find was something like a business to run or to start that had that kind of upside to it, but also I just loved it just, pulled at my heart a little bit. And I felt that way about this and I still feel that way. It’s like you talked earlier about the creative playground and I think that’s what Every is. And that is the best. It’s so fun to wake up every day and do that. And it’s just a different feeling than the B2B SaaS stuff, which is cool, but the core of Every feels different. It’s warmer.

Brandon Gell (00:40:00)

Yeah. And so, where did that go wrong? The collective idea.

Dan Shipper (00:40:10)

So the problem that we found was there are very few writers that can actually make it on the internet and there are even fewer business writers because in order to be a really good business writer, you have to know what you’re talking about. You have to be able to write, you have to be able to do it all the time, every week, or more—at least, at least weekly, maybe more. And you have to want to 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 would just rather make money, which makes sense. And so and so what we found is basically we started the company, we were the main writers when we started, Every was growing. We were like, cool, we’ll just go hire. Now we raise money. It’s 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 a product-market fit with a particular writer and then you change the writer, 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 the media that doesn’t work at all for the reason I just talked about. 

So for a while, the business was sort of stagnating, even though we had other writers doing it. And then through that whole period, we found one writer who was good enough to really sort of be part of it and help carry the publication or what became the publication. His name is Evan Armstrong and he writes Napkin Math for Every. But over time, what we found is the idea of having this scalable collective of all these different writers, it just didn’t work. Because the supply constraints of writers were really hard to work out. And then also just like figuring out the bundle economics was really hard bundle economics. It’s a mess basically. The system gets complicated and everyone’s unhappy and whatever. So it’s very hard to do. A lot of people do it because it’s a great business if you can make it work, but it’s hard. So anyway, so eventually we kind of realized, yeah, what we’re really doing is we’re not building all these different newsletters, because only a couple of the writers are really working. We should really just build one or two newsletters and have all the writers that are working in one place. And then we can have the other ones that aren’t working as well. We can have them contribute, but we should just focus all our effort on the winner or winners basically. And also, around that time, I kind of made a decision that I wanted to write more. And that also helped a lot because that’s like— I love it. It’s a thing I love doing and I’m pretty good at it. So I kind of like made the decision instead of doing the typical CEO thing and hiring other people to do a lot of the on the ground work that I would also be a—or the—main writer.

Brandon Gell (00:44:19)

I think that is actually a really important point and also kind of part of why I wanted to join Every too, which is you felt the need to not write because you’re supposed to scale the company, even though it’s what you’re good at. It’s what you like to do, which is like just to reiterate, it’s what you’re good at that you like to do. You’re supposed to not do that. And I think that, one thing that I just love being here at Every is—I don’t know if I could say this on the podcast, but [bleep] that—you should just do the thing that you’re really good at and you like to do. And, it just feels like such an unlock to be able to, 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 be hired in this way. And we’re supposed to build a product with three engineers and one designer, one PM per pod. And Brian Chesky actually has a great talk about designing your company. And I feel like that’s exactly what we’re doing here. And it’s just a better business and it’s more fun.

Dan Shipper (00:45:40)

Totally. I think you’re spot on. It’s sort of what I did with my first company too, in a lot of ways. And I think it’s part of maybe being a younger entrepreneur, but some people never grow out of it. And I think what we’re trying to do at Every is actually like look at what we want to do and who we are, and how we can 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 pick up other people’s expectations and then try to fulfill them regardless of what I want. And it’s taken a while to figure out how to do that. I still fail often, but I think it’s becoming more like that, which is really great.

Brandon Gell (00:46:35)

So, okay. So Every now— Actually, if you’re an Every subscriber, you can actually see the legacy, all of the columns still on through the account creation part of the website. So it’s changed to be sort of one newsletter. And then, I mean, now it’s evolving a lot in the past four months. I feel like there’s been sort of—unbeknownst to a lot of listeners and readers—there’s been a ton of transitions and evolution that was announced in Every Master Plan article that you wrote, but maybe you could talk about that a little bit.

Dan Shipper (00:47:12)

Yeah. I’d love to talk about it. I also say like in that all that sort of the messy middle period my co-founder Nathan built this app called Lex. And we spent a lot of time in Google docs editing, writing, and all that kind of stuff. And he likes it, maybe there’d be better Google docs. And it’s always been kind of like in our mind to build little products cause that’s sort of where the original idea for Every came from. And we’d done that along the way. And so he started building what became Lex. And it was right around the time when GPT-3 was starting to take off. ChatGPT has not been released yet. And we were like, it’d be kind of cool if you just like to put that into the word processor you’re making. So he built Lex, we launched it and it just went super, super, super, super viral. 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. And I think that was another accelerant for me to be, well, what do I really want? My co-founder is gone. This is because every business has a bunch of different reinvention moments. And I think that was a reinvention moment to be, okay what do I want? And what do I want this to be? And, 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, I think, at the core I’m a writer and I think actually what I’d love to do is because there’s this kind of Every Master Plan, but before I wrote that article, you joined. And I think it would be nice to talk a little bit about that, and that process. And I don’t want to swerve the whole thing, but one of the things that I’m wondering, because we got to talk about my origin story and I don’t think I even know your origin story. Obviously we’ve been friends for a while, you sort of came onto Every after your last business, but how did you end up, how did you start, how did you start getting the entrepreneurship thing? What were the origins for you?

Brandon Gell (00:49:20)

Yeah. Well, the earliest days, it was sort of classic taking stuff apart. You know, building stuff with Legos. And in my earliest days I couldn’t— I’ve always loved making stuff, but it was always with my hands, but I was never good at math. And so I ended up going to Middlebury in Vermont and 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. And the challenge was basically to build a house that’s entirely solar powered. You have to fly it, train it, drive it to Irvine, California, build it in seven days. There’s a competition about the aesthetics of the building, how well it performs, a whole bunch of different things. And then you have to take it back to do something with it. And typical participants are Team China, Team entire countries, huge universities, and then somehow Middlebury, which is a 2,400 person liberal arts school with not really an architecture program. It’s certainly not a construction program or anything—they applied, got accepted and then the school gave this team $1.5 million of funding. And I somehow learned about this and was just like, this is the coolest thing ever. And I mean, I toured Middlebury on a crazy, crazy snow storm and was like, I love it here. And I think it was in part because of the Solar Decathlon. I landed on campus freshman year and that became my world and I taught myself AutoCAD and I sort of became— Our strategy for building this, we wanted to make it a really, really efficient house. And that included how we were going to get it to California. And if you fly a house to California, that’s a lot of gas burned. If you drive it, that’s a lot of gas burned. But if you train it—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 it had to be panels that were no wider than 7 ft.. Nothing could be wider than 7 ft.. So that heavily influenced the design. And then, freshman year, no experience with AutoCAD or architecture, it was like, I’ll teach myself AutoCAD and I’ll sort of be the guy who makes all the schematics. So I essentially made the blueprint for every single panel and became, sort of a really, really core member of this team, which primarily had seniors and then there was the 120 lb. freshman Brandon who knew nothing and was super young and I just stayed there that summer. 

We literally built the whole house and I was a very core member of the team and that was sort of You didn’t 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 and built a bunch of furniture I like and got really close with a bunch of people in town that were metal workers and woodworkers that helped us build the house. So I had access to all of their studios and went to their shops and built furniture. And then my senior year I did two projects that were really, really influential on what I went on to do next. 

One of them was that I had gotten close with this girl who wanted to build a bus. She wanted to renovate a school bus, a 52 ft. yellow school bus, but had no construction experience. And I basically came on board and the two of us bought a school bus, gutted it over the course of two weeks and then completely renovated it into this beautiful school. We turned it into a mobile school that taught entrepreneurship. She went on and toured the country in this bus and had an amazing experience. So that was 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, Dave, and went on to build a photo-printing app called Photon. And the idea was we all take a lot of photos. We never look at them. I think if we had done a second of market research, we would have known that Shutterfly existed, but we were like, we’re going to do it on our phones and it’ll be a really easy and super low barrier to entry for people to print photos. And that didn’t really work like my aunt printed a ton of photos but it was an incredible experience. We learned a lot. And that’s sort of where it all started. And then I became a VFA fellow and went to work for a startup out of Columbus, Ohio.

Dan Shipper (00:55:08)

Yeah, there’s so much in there. I mean, one that sticks out to me is obviously just the feeling that you love building, which is such a core part of being an entrepreneur is living building things. But the other thing that you said that really stuck out to me is like I was just a 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.

Brandon Gell (00:55:50)

Yeah. I think everybody who’s built needs to be down for that. It’s kind of a weird, totally unwarranted level of confidence that you shouldn’t have, but I don’t know. It’s just, yeah, you have it too. You have to.

Dan Shipper (00:55:57)

Yeah, you kind of have to. And it’s surprising. I mean, maybe not surprising, but it’s rare. It’s rare—there’s no manual, there’s no instructions. And I’m pretty behind and I need to figure this out. And that is actually appealing to me instead of being so overwhelming and stressful that I don’t want to do it. And I’ve just watched you do that over and over in the work that we’ve done so far and it’s very impressive.

Brandon Gell (00:56:29)

I think, yeah, just being curious is such a core part of being an entrepreneur and it’s hard to be that without having that curiosity because there’s just endless problems.

Dan Shipper (00:56:46)

Yeah. You have 5 love problems.

Brandon Gell (00:56:50)

Yeah. You can’t be intimidated by them. You have to be energized by them.

Dan Shipper (00:56:52)

Yeah. Okay. And so you did the photo app. What was the impetus for that? Because that was the first thing that you mentioned that looks purely like a business.

Brandon Gell (00:57:05)

Yeah, I think I just sort of liked getting it. I know that I had downloaded a bootleg version of Sketch and it was like, cool, I actually really like graphic design, specifically mobile design. And I had gotten close with Sharif and Davin, who are both really talented engineers and back then were comp sci majors and, yeah, we just were like, we want to do something. And then I think I literally was like, I like photography? Let’s print photos. And that was it. And then we did it. Not a lot of thought went into it, but it was, I mean, there’s big photo printing apps now. So I think if we stuck with it and knew what we were doing, it could have gone somewhere.

Dan Shipper (00:57:57)

Honestly, I think sometimes less thought is better, especially at the beginning because it’s so easy to just psych yourself out and convince yourself it’s a bad idea and then never do anything. And the whole point of that early stage of doing stuff is not because it’s going to be a huge thing off the bat, which would be nice if it was, but it’s just learning how to like make any kind of business, the fact that your aunt used it means that you ship something, which is the important thing.

Brandon Gell (00:58:22)

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 a bigger opportunity. But yeah, it was important just to be—whatever, let’s do it. I have a feeling. 

Dan Shipper (00:58:38)

[Bleep] it. Okay. So, after that you did VFA. What was that like?

Brandon Gell (00:58:45)

I did VFA. RIP. Just shut down, actually.

Dan Shipper (00:58:49)

I saw that.

Brandon Gell (00:58:50)

So yeah, I did VFA and played a bunch of basketball with Andrew Yang, actually, which was a fun fact. He’s a really, really good basketball player. And yeah, so I went to work for this really cool startup out of Columbus called Knockout Concepts and they were designing and building a 3-D scanner. We were a four-person team. I think I literally chose to go work there because they had a really cool office in a warehouse with a ping pong table. And I was like, this technology is cool too. And I really like 3-D design. So this is perfect. And yeah, I was trying to figure out how to bring this product to market. And that meant Shopify—a very basic shop. We’re going to launch it on Shopify. We needed it, it was expensive, so we needed some financing. So we launched a firm and had a software component that 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’s like a $3,000 product, people will like— They’re taking it into like— Underground piping gas companies were using it to like skin pipes. And we’re like, they’re going to break it. And we like to have no money, so we can’t really afford to replace it. So let’s offer insurance and Shopify, Affirm, and Stripe are like these amazing, really simple experiences. And I expected an insurance offering to look like that. I did a bunch of Googling and didn’t find that. And this is where that sort of acknowledging problems part of me wasn’t yet really built out because I didn’t sort of recognize immediately. What I just recognized is this is annoying, now I need to go talk to an insurance company six months later, I sort of got there. And I was like, these insurance companies are awful. The people there are not really that enjoyable to work with right now. The experience that they want to give my customers is not going to be good. There’s zero technology when I’m asking them for API docs or anything. They don’t even know what those are. And that was sort of the beginning of. There’s and there’s an Affirm version of this product and then the naivete of a 22-year-old that doesn’t know much to be like, and I’m going to solve it and I’m going to build an insurance company. That’s super privileged to be able to do that and had the backing of my parents and I lived with my grandma for a year while building the first version. So very, very lucky to be able to do that. But, yeah, it took a while to figure it out.

Dan Shipper (01:01:42)

And so, yeah. Just kind of give us the high-level elevator pitch of Clyde.

Brandon Gell (01:01:48)

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, policies that they sell, which they actually do. They don’t take on any of the risks. They work with an insurance company. Now, if you’re Knockout Concepts, which is 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 the insurance company is going to make any money from it. What I didn’t know at that point was that even a Dyson wouldn’t be able to go to an insurance company because an insurance company is like I can launch five programs a year because it takes an army of people at my insurance company to launch these programs. So the value of each program needs to be super, super high. So what we essentially realized was like, well, why don’t we just make it super easy to be able to launch a Shopify app or a couple lines of code, and why don’t we build this marketplace of insurers that we can like very, very quickly match policies that they’ve built to products. So at the launch of Clyde, it could take 30 seconds if you’re a Shopify app or if you’re a Dyson. Unfortunately it could take a very, very long time, but not because of the development work, just because of bureaucracy.

Dan Shipper (01:03:32)

Yeah, and it was around the time where you were 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 I remember seeing the pitch and really liking it. I don’t remember. I didn’t end up investing, but I don’t remember why. Because my only memory of the pitch and the aftermath is I was really impressed by you. And I was really impressed by the updates I was getting from you. And it was in the category of deals where I was like, that 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 I kind of just missed it. And then I just felt bad about it. But, what I remember is I saw a lot of pitches and I think you had this really, really special combination of you were super ambitious and there was a big vision for what you were doing. I felt like the business was actually really intellectually rigorous, like you had really thought through the landscape of why there was a problem here and how to solve it and stuff like that, but you were also very just straightforward. I believed you, you know, like I didn’t feel like you were fucking around in any way, which it’s very rare to have that combination of I’m ambitious and really motivated, but also I’m like pretty straightforward and I’m not putting on airs or whatever, or trying to be something I’m not, I just am. What you see is what you get more or less. And I really liked that.

Brandon Gell (01:05:27)

Yeah. I mean, when I look back at that time, it was very, very focused. It was like, this is the only thing that matters right now. And going on dates cause I just moved to New York, and I was really excited about that too.

Dan Shipper (01:05:40)

Tell people about your dating strategy just really quick.

Brandon Gell (01:05:42)

Which one?

Dan Shipper (01:05:44)

You told me that you would go on I think early morning dates.

Brandon Gell (01:05:49)

Oh, yeah. I was very focused on— If somebody wanted to get a drink after work, which I wasn’t super into, I’d be like, how about a 7 a.m. coffee? And some people were really down and others were not, and they weren’t good fits. 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.

Dan Shipper (01:06:13)

I have. Well, I mean, which one? The one at East Village?

Brandon Gell (01:06:14)

Spa 88. 

Dan Shipper (01:06:16)

Oh. Spa 88. I’ve never been to that one.

Brandon Gell (01:06:18)

Only one person was down and it was a really good date. It was super fun.

Dan Shipper (01:06:20)

I think that’s the spa that either Huberman or Lex Friedman likes, but I’ve never tried it.

Brandon Gell (01:06:36)

Oh, really? So yeah, I just remember looking back at the time of being like, he 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 these pretty big insurance deals that we needed to close to launch the business. And I remember being really focused on signing deals. What’s the word I’m thinking of? I didn’t want them to be exclusives. So we got a couple offers from these insurance companies. Oh, we’re just going to bully this startup and just tell them it’s exclusive. And we had to turn it down. And it created all of these unknowns of, are we going to be able to find a partner? And I think it’s important when you’re building, we had a vision for 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. They should be making as little money as possible, which in hindsight doesn’t really make sense because they need to make some money. But we did that and I’m so happy that we did because that became a core part of our offering, and a competitive edge. But it was really, really— You kind of in those early days need to be able to say no, even though if it potentially jeopardizes what you’re building.

Dan Shipper (01:08:00)

Yeah, totally. Why do you think you had the confidence to do that at 22?

Brandon Gell (01:08:09)

No to those deals? It just sort of felt like it wouldn’t be worth it. Otherwise, I think we would sort of be stuck there. I mean, there were definitely days when we were considering taking it just because we needed to go. And I was making $18,000 a year, living with my grandma. And that was after not making anything for a long time. So, I think it was just like, what’s the point? This is going to be so hard anyway. We should just try to do it right.

Dan Shipper (01:08:50)

That makes sense. And, so tell us a story of the business because we’re starting to get into the meat—that you spent seven years running that business. So you were trying to get into the meat of it. What’s the story? How did it go?

Brandon Gell (01:09:00)

The story of the business? Well, I think it’s actually a bit of a cautionary tale. So when I was 22, I raised $3 million, got an office, hired maybe 12 people, and we made the product and 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 the litany of challenges that this type of company and this type of product we’re going to encounter—namely, competition, which didn’t exist when we raised, but existed soon after. Time to value, which is when you close a deal, how quickly we’ll let that business start generating money for you because we had a product that people needed to implement. And then the last one is spending money. It can be dangerous. We had money to spend and therefore we spent it and we were encouraged to spend it. So what happened soon after is we didn’t really know all of the dynamics about how the business worked yet. We were finding success with growing our clients and growing the number of clients, but soon we needed to raise again. So we raised $14 million. And it’s this sort of pattern that just keeps continuing. We raised, we had more money, we spent the money, we grew our clients, but we now there was a new dynamic in place, which is the economy was changing a lot. And then the same thing happened. We had to raise again. We raised the B and then the economy started tanking. Because the pandemic had just hit, then everybody got $2,000. So even though the economy was kind of not doing well, people were taking that $2,000 and spending it like crazy. So we saw our business just totally skyrocket even though, I’d say the core problem with our business wasn’t changing. And that problem is if you close a big deal it takes a long time to launch that deal, which is, I think, a cautionary tale for any B2B business that requires implementation.

Dan Shipper (01:11:38)

And why is that such a problem? What causes that to make it hard to make the business work?

Brandon Gell (01:11:44)

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. So you’ve got sort of these business people that are out, trying to drive revenue or probably compensated on driving revenue, but then you have the technical team that needs to implement what the business people have decided to do. And what we found would happen pretty often is a business person would be psyched about launching Clyde because they were going to make really high-margin revenue from it. We’d sign the deal and then the technical people would be, whose Clyde? We’re not ready for this. We’ve got a bunch of other stuff that we need to work on. So we’d have to resell again. And there were things that we did in our sales process to try to stop that from happening, including technical people in the deal or in the sales process. And then the other challenge is, I think, especially in retail, it’s just a freaking mess. People use different ERPs, these ERPs are really legacy. So no one there really knows how they work. They’re using different headless software and different e-commerce platforms. And I think one thing I learned is, 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. And that, I mean, that’s just like a very hard lesson to learn about focus.

Dan Shipper (01:13:24)

Yeah, boiling the ocean, maybe the market size—total market size—is bigger, but it’s sort of a little deceptive because the divided effort means you don’t get as far, even if the TAM is higher.

Brandon Gell (01:13:37)

Yeah. And then eventually we were like, we either need to fundraise or we need to sell. And we had a bunch of buyers that had come to us and expressed interest. So we ran a sales process, found a buyer—a great company called Cover Genius, was a competitor out of Australia that was trying to break into the U.S., but was kind of struggling with super aggressive sales. And they didn’t really have that muscle. And we did. And. There’s a great fit. And yeah, March 14, I’ll never forget. Signed the deal. It was like a couple of weeks after Silicon Valley Bank shut down, which was a whole, whole other—oh my god. This was a crazy four weeks of selling this business.

Dan Shipper (01:14:20)

And what was it like? You know, the moment you signed it, because I remember selling Firefly. I remember that moment. What was it like for you?

Brandon Gell (01:14:28)

I mean, I remember signing it and we were working out of Cover Genius’ office workers, going through diligence and just—it was really collaborative. They were amazing to work with. And I remember I had our CFO and an accountant there, kind of the guy who could really go through a lot of our data and make sure everything was clean while we were building out the data room. And we all hugged and then I went for a walk alone and was just sort of—I don’t know—I’m emotional even thinking about it. It’s sort of like this— I remember that walk feeling simultaneously really freeing of like, I had done it. And also really kind of just like, but now what? Who am I? And I know that I have this challenge ahead of me. And, yeah, it was really emotional.

Dan Shipper (01:15:32)

I’ve felt that too. And it’s such a weird thing because you also feel like you should feel great. And there’s not really a playbook for it. I think for a lot of life moments—you graduate high school, okay, now I’m going to college. You graduate college, now I get a job. But I think one of the interesting things about the entrepreneurial path, which is very unstructured, is that. When you sell, there’s not that next thing for people and you just sort of can fall into this black hole of like, I just lost my identity. I lost the thing I do every day. And what now? And there’s, I mean, it is sort of a cliche thing, but it’s also just actually just totally real. It’s very hard.

Brandon Gell (01:16:16)

Oh, I mean, it’s such a champagne problem. You just sold a company and now you’re like, but who am I? And that was also really hard because, what ends up happening is everybody congratulates you, congratulates you, and everybody asks what you’re building next. And I was like, the way that I described this feeling to my friends and to my family was like, I can’t hear the music anymore. And, the first thing that I’m going to do is go to try to hear the music again. Now I can hear the music though. So, it’s been a journey.

Dan Shipper (01:16:50)

That’s hard. Yeah. So it sounds like you’re a little shell-shocked or something, just a lot of going through— The image I have in my head is someone put you in a dryer on the perm press cycle or whatever. And you were just tumbling around for a while and then someone took you out and we’re like, okay, you’re done now.

Brandon Gell (01:17:17)

Everything calmed down. So Clyde was not a calm business and then everything all of a sudden got really calm. And that was an incredible feeling, but it also took a solid three weeks of just decompressing from that state, where I cried a bunch, I got super sick, all these things. I needed to process it. But I’d totally do it again. I mean, it was so cool. And I met amazing people and, I mean, we are doing it again.

Dan Shipper (01:17:49)

So that’s a really good transition into how you came to Every, so you sell Clyde, you’re kind of trying to hear the music again. Take us through how we started working together.

Brandon Gell (01:18:05)

Yeah. So I was very similar to you, sort of stumbling through the desert, trying to figure out what I wanted to do next. My wife and I did sort of the classic thing that excited founders do, which is 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. She was working. And I had to sort of wrap up my time at Cover Genius and was experimenting with a bunch of new ideas. So, I was working again with Sharif who I built Photon with and we were trying to find problems, which was really, in hindsight, not a good idea. I just feel like when you’re trying to find love, that’s 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 love doing was having an idea and then building it super fast. So figuring out if people were going to use it, trying to get a version in their hands. I got banned from Reddit 10 times during this period trying to talk to people. And that was like, I just loved that we didn’t come across any idea and then his life took him in a different direction. He needed to move somewhere and we just didn’t end up this time around, and it didn’t end up working out for the two of us. And again, I was sort of back to the desert trying to figure out what I wanted to do. 

And then, I’ve been an Every subscriber for a long time. And I got an article in my inbox. It was called— Oh yeah. Well, so that’s actually something that I got a while ago. I got, “Be Sincere, Not Serious” when I was still running Clyde and that changed my whole mentality. This was, “The One-person Billion-dollar Company.” It was a Napkin Math column about, is solopreneur actually even possible. And this was when Sam Altman and all his poker friends were betting on, is it possible? And it was all over Twitter. So you guys did a column about, is it actually possible? And Evan basically netted out to like, no, it’s not possible. And it sort of was a light bulb moment for me like, what about building? I really have liked the sort of studio aspect of what I’ve been doing, where I get to experiment with different ideas and move really quickly. 

And I realized two things. One, 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 get users and every sort of had this unlock moment of, well, Every has that, they already have distribution. And then I had this other thought of, well, maybe we could get people to build a billion-dollar business solo if they just had the right tools and maybe there should be a whole product studio that exists to just build those tools to enable the billion-dollar solopreneur. I think that’s what I wrote in an email to you.

Dan Shipper (01:21:37)

You did.

Brandon Gell (01:21:39)

So I was like, “What’s up, Dan? It’s been a while.”

Dan Shipper (01:21:42)

Let’s pull up the email.

Brandon Gell (01:21:44)

Let’s pull up the email. Yeah. I remember being so psyched to hear back from you and just being like, I really had this feeling when you responded this might be my future.

Dan Shipper (01:21:58)

Seriously. Alright, I’ve got the email. So, what I like about this already is that subject line, “Long time no talk—considering my next move.” It’s like, I have to open that. Come on. Who’s not going to open that? “Hey Dan, it’s been a minute. I just read that one-person, billion-dollar company. I was inspired to reach out. When we last hung out, we got a drink at the Spring Lounge and you were telling me how Every was just beginning to take off and that you needed to take it off the Substack. And then you went on a few dates with someone and were psyched about them. I can’t remember where I was with Clyde, but it’s all a blur.” I remember getting drinks at Spring Lounge. That was fun.

Brandon Gell (01:22:40)

Yeah. You were gushing about this girl. You were like, I found them. This is amazing.

Dan Shipper (01:22:44)

Spoiler alert. It didn’t work out. And I think at the time you were in peak Clyde stress. You were just like, oh my god.

Brandon Gell (01:22:57)

It literally was all a blur.

Dan Shipper (01:22:58)

“I sold Clyde in March of ‘23. Wrapped up my earnings. I took a bit of time off, but quickly got it to work with a buddy of mine from Middlebury on building out a tiny style studio, building smaller profit-driven internet products that week that could send on their own. It was super fun and we were off to the races, 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 to 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. From 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 curious to hear your take.” I got that email. I was like, fuck yeah. I’ve been thinking about this for forever. This is amazing. And, I said, “Very interested in incubating new products for Every and I have a ton of ideas I would love to hang on to.” So that was the beginning of it. You had this brainwave. You told me that, I think you were in Nicaragua when you sent this email, right?

Brandon Gell (01:24:02)

Yeah. I was in Nicaragua. And then, so I sent that email, 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. And that’s where I laid out these three pillars of Every that I thought could exist. And I thought maybe I’d be a good person to run one and why do I enjoy doing it? I don’t know if we want to talk about those.

Dan Shipper (01:24:34)

Let’s do it. Bring them out

Brandon Gell (01:24:38)

So the first one was consulting. It just sort of felt obvious to me that a lot of people really respect everyone. The business is so knowledgeable on AI and led by you, who has a lot of experience building companies and being entrepreneurial. And with this sort of addition of me, there’s two of those people. And that could be pretty powerful. So maybe we could do consulting. There’s this other sort of core idea, which is, well, we should just build more products. We would like to build a product studio and maybe the theme could be apps or software to enable the billion-dollar solopreneur. We didn’t really land on that, but like the idea was to build a studio and a profit-driven studio. And then the last one, which like we’re furthest from, but I’m still thinking would be amazing is we should invest in companies because VCs, not all of them are great. And 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 clout. So, I just felt like we could get into any deal that we wanted to get into. So, these were the three pillars. I wrote them down in a Notion doc. I probably can’t find it now. It’ll take too long, but I wrote it down and. I sort of wrote down why I thought each one would work and it kind of we’re going down exactly like I wrote it basically.

Dan Shipper (01:26:17)

It’s going to plan, which rarely happens. So it’s pretty sweet. It’s pretty sweet. It honestly has felt— So basically when we first started talking, there was a little period of, okay, what’s the deal? How are we going to work together? One big thing was, how are we going to fund this? And we decided, 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, which is like a risky thing. 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 people on AI and also just knowing which AI products to buy and work with and implement all that kind of stuff. And it’s been amazing. And the studio stuff has been incredible. So we’ve launched two products—Spiral, which helps people automate 80 percent of their creative work. Basically, it’s sort of like a powerful prompt builder. So you can make a Spiral for me. I use it all the time for this podcast, actually, to convert my podcast transcripts into tweets and LinkedIn posts. But it’s used 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, 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 in Star Wars where the Millennium Falcon, they do the jump to hyperspace and all the stars start blurring. That’s what it has felt like since you joined, it’s been really incredible. You’ve just totally just raised the level of our execution and our pace dramatically. It’s been super fun.

Brandon Gell (01:28:08)

I mean, I think that one of the best parts of being here is that the quality of people that we have at Every is just so high. So the quality of people that were already here and then the quality of people that it seems like we’re able to recruit fairly easily is such a competitive advantage. And then also the mentality of the business is to build calm businesses. I mean, I feel so passionately about this, if we’re not having fun, then what’s the point. And we’ve so far been able to maintain that. It hasn’t really been four months, but it feels like we’ve done the work for a couple years, honestly which is so exciting and yeah, it’s working.

Dan Shipper (01:29:00)

It’s working. And I think that’s sort of, I think, a good time to kind of bring up that master plan thing that we swerved off of, I don’t know, an hour ago or something like that. But basically, what it has sort of turned into is Every started as this place where we wanted to make great business writing—really, great business and technology writing. And I think we’ve grown and changed a lot in how we think about doing that because running a media business is just really hard. It’s just really hard to make a good business. And what I care most about, and I think what everyone at Every cares most about is making that creative playground where people come to do their best work and building an institution for the kind of writing that we love and extending that into podcasts and courses and software and all that kind of stuff. And 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 it doesn’t end up being like all these media companies that like to raise tons of money and then blow up or whatever. You can think of it like a pyramid or what we talk about it as 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 high-quality things that we do that are free, that get people in the door and get people acquainted with Every. 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, every Every paid subscription incorporates all the writing that we do access to sort of behind the scenes stuff from the pod, this podcast discounts on the courses that we run, and then also access to all the software we build. So there’s access to Spiral, Sparkle, and Lex, and with more coming. And the idea is, maybe 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 subscribing to the Every subscription. And then a layer above that we do training and consulting. And courses and far few, far fewer people do that. But you pay far more. And then above that is speaking or advising or other, other kinds of things, which are even more expensive. And even fewer people do that. And that seems to be 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. And that seems to be a structure for 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 a more Silicon Valley-style tech business where the recommendation or the thing you’re supposed to do is focus on a business model and just make that crank that just makes that work. And I think what media companies need to do if you have the core asset you have is sort of 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. It’s a pretty big bet. It’s a bit different. But it really, honestly seems like it’s working in a way, I think it almost never works this easily. So I’m almost suspicious, but it’s really working. It’s pretty great.

Brandon Gell (01:33:17)

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 Every has really high-quality content that a lot of people read and listen to. And that is the engine behind the whole rest of the business. It just doesn’t work without that. And that’s also why the very first thing that we spoke about, you should be writing and you should be talking and that’s what you’re good at. And that’s what you like to do. And if you didn’t do it, the rest of the business just wouldn’t work. And this is a model that I feel like is very big on Twitter and people are now beginning to realize like, oh, distribution. When intelligence costs zero, basically, its distribution that’s important. And this is like this new thing that a lot of people are talking about. We are in a very unique position, I think, where we’re actually leveraging that. And thankfully everything had been built up before this model became a real concept and we’re just sort of cranking it and trying to move really fast on it. It’s sort of the new— I don’t want to compare it to the New York Times, but the New York Times sort of 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 to like that people really want to interact with and that’s bundled all together. But they are sort of really good. And a lot of their content isn’t free, but some of it is and there are really good sort of models I think to base off of. And another thing that they do, that’s just, I think, a model for us, 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, work really well, and actually have value. We’re not going to put it out if it’s some bullshit which hopefully we can maintain, that’ll probably be the hardest thing to do.

Dan Shipper (01:35:44)

I think so. Yeah. I mean, I think that that’s a risk. I think also the risk is all these different levels of the pyramid, to some degree, have different incentives. And so keeping everything aligned. And supporting each other as things go on is also going to be a really interesting challenge. But I think one of the things that I really like about Every is we haven’t raised a lot of money. So there’s not a lot of external pressure. And I just love everyone that we work with. I love everyone on the team. It’s such a good team feeling. There’s some little magic thing happening right now. And I just want to keep that going. And I think if we can keep that core group of people together and not what I think we push to move really, really fast, but what we’re not doing is going and raising a bunch of money or hiring 15 people in a week or whatever, that kind of stuff. You talked about sort of being calm and I think when you’re launching as many products as we launched, there’s definitely some stress involved, but there’s that sort of the core thing where it’s like, partly we’re doing that because it’s fun and we do get to set the pace and what I don’t want to lose is the kind of creative playground, we’re doing really high-quality stuff. That’s the point of all of this. And I think we’ve got a shot to do it because I think we have figured out a structure that works to support it. And I’m just psyched about it.

Brandon Gell (01:37:27)

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 [email protected].

Dan Shipper (01:37:37)

Do that. Yeah, we’re looking, looking for entrepreneurs in residence—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 be— In the show, we tend to look at how people work with AI but maybe we can show some people some of the stuff we’ve been building. I think it’d be really fun. You know, 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 tools that we build which have come out of problems that we’ve had. So I think it’d be great to demo it. You want to demo Spiral?

Brandon Gell (01:38:15)

Yeah, let’s do it. So okay. So yeah, this is Spiral. And I’m looking right now at our team Spirals. So are there the Spirals that our team has made and shared with each other. And so this is one of the Spirals to turn a podcast transcript—so literally a raw transcript into a tweet—which you’ve used successfully. I use it for a week. So, I mean, we’ve created some pretty serious viral tweets. I just know that I ‘ve like tested it with this before. So I know that I just have this Google doc with a pretty good transcript.

Dan Shipper (01:39:01)

And this is the episode that I did with Kevin Roose of the New York Times on AI friends. And so this is a workflow that I do every week is I take a transcript and I paste it in there like that.

Brandon Gell (01:39:12)

Yeah. Literally just copy and paste the entire thing. And now we’re going to run it. So it’s going to take a second now to basically take this super prompt that we’ve built with the input, the output, and a bunch of examples that we’ve trained the Spiral on, send it to Claude and it just returns the output, which is tweet. So, “Kevin might be the first person to have 18 AI friends. He’s a columnist in the New York Times, host of the Hard Fork podcasts and author of Futureproof,” which by the way, I don’t— One thing that’s really cool about Spiral is this actually may not be in the transcript, but it uses Claude and it actually knows who Kevin Roose is and can pull in that information. Yeah, “His experience was both compelling and repelling. He created AI friends for parenting advice, outfit checks, and was even tea time gossip. We dive into”— I mean, this is just like, it’s just really, really concise. It’s compelling. It captures your attention and it’s tight.

Dan Shipper (01:40:26)

And yeah, I mean, the thing is this is also how I write my tweets for my podcast. It is exactly like you. And it’s the format that I use. And this is sort of like how it came about too. I have to tweet every week and the tweet is, to some degree, the most important part of the podcast. Because it’s the thing that most people are going to see—it’s how I get distribution. And that process is really boring. But it also requires a lot of skill. Even though it’s repetitive. And sometime in May, I realized that Claude was good enough at writing to actually do this for me. but the prompt was super long and hard for me to do. And I knew no one else was going to do it. But I thought it could be really helpful for, not just me, but anyone on the team, because well, a lot of what you do as a media business and businesses in general do this is, you’re taking creative work or some sort of work in one form and you’re translating into another form. So, we do this as a media company, but lots and 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. And so I realized Claude could do this and it was actually on what we mentioned earlier on, on a Think Week which every quarter we take a Think Week. We don’t do things like our regular meetings. We don’t publish new articles and it’s just like a time to let our brains run free and sort of reflect on the last quarter and plan for the next quarter. And in just two days, I just went into a fugue state and was coding with Claude and built the first simple version of this, where it was like, you could build a Spiral and sort of train it on your own. For me, it was training previous examples of my own writing. And it worked after two days and we were looking at it and just using it internally and that the writers on our team liked it. And we were like, wow, that could be cool. That could be a product.

Brandon Gell (01:43:48)

And I think that this is actually a really good time to shout out the article that you wrote about Excel because you basically did the same exact thing, but instead of Excel, it was Claude, and it was this thing that you kept using Claude for. And you can, I mean, this is what the definition of an AI wrapper is. 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. And there’s so many opportunities like that. I mean, we have another one—it’s Sparkle. It’s basically the same thing—that same concept. So, how long do you think it would take you to write this?

Dan Shipper (01:43:35)

An hour. Because what I’d have to do is I’d have to rewatch the whole podcast. 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.

Brandon Gell (01:43:50)

Yeah vs. what?

Dan Shipper (01:43:52)

Five seconds? And to sort of explain a little bit more of the point you just made about the article I wrote, the thing that I’ve been seeing and then I think we’re kind of keying on for a lot of the products we build is, Excel is this really general purpose tool that taught a lot of 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 it’s really simple to start. Anyone can just type into a cell, but you can do enormously complex things with it. The 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. And 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 like business processes and all this kind of stuff. And I think Excel really created the the sort of B2B SaaS wave because once people were 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 really custom for their specific use case that Excel just wasn’t that good at. 

And I’m not the first person to say this—I’m taking this from this guy, Tom Tunguz. I think he used to be an investor at Redpoint and I think he’s at another fund now, but he’s a super, super smart, really great writer. And so Excel progressively got unbundled over the next 20 years into All these different SaaS products and it’s still around. Obviously, Excel is a super important tool that is one of the most widely used pieces of software ever. But it also got fragmented and all these other purpose specific tools. And I think ChatGPT and Claude are basically the same for a new generation of computer users. There are incredibly powerful tools. That’s really easy to get started. They’re incredibly general purpose. And I think 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 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 prompt Claude to do this, but it’s a pain in the ass. And so they immediately sort of recognize, oh, having a purpose specific tool for this is really good. And there’s this expanding horizon of people who are starting to get used to AI enough that they want a tool for something like this.

Brandon Gell (01:47:23)

I actually wonder. So I have a bit of a different take and I wonder if it actually unlocks the power of AI for all of these people that actually wouldn’t go to Claude to do that because now they have— One of the problems with Claude and ChatGPT is the way that you interact with it is it is literally just a chat function. 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 how to be creative. And, that is the definition of not in a box. You would like to do literally anything with it. So I almost wonder it’s this purpose-driven thing that’s supposed to do really one thing for you, and does that make it more accessible to all the people that actually wouldn’t go to—? 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 it’s sort of the unlock for all of those people that don’t use AI to start using it.

Dan Shipper (01:48:30)

I think you’re totally right in the sense that it is easy enough to use that people who don’t use AI can use it 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 looking for this as a solution are the people who know it’s possible, but know it’s hard. And those are people who have already adopted 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 would never even like it. Think about searching for something like this. And maybe their colleagues skip from like, they don’t even have a phase where they’re using Claude. They’re just using something like this. And maybe this is the gateway for them to be like, whoa, maybe I should use Claude because 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 the early adopters are the people who know that there’s a problem because they’ve been using Claude for this and are I think there’s something better to be had here.

Brandon Gell (01:49:46)

I think that’s right. And I think you definitely actually see that with Sparkle because 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 the sort of 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. And I think you can actually see that, we both thought Sparkle was going to be a bigger launch than Spiral turned out to be a smaller launch than Spiral, but I don’t think that we realize just how invasive of a product it really is. It’s not actually because it can’t delete your files. It’s super easy to undo it. But mentally that’s very real.

Dan Shipper (01:50:52)

Yeah. Well, let’s see your desktop.

Brandon Gell (01:50:54)

Here’s my desktop.

Dan Shipper (01:50:55)

That’s pretty clean, man. Doesn’t it feel like a breath of fresh air?

Brandon Gell (01:51:01)

Every time I look at it.

Dan Shipper (01:51:04)

And that’s Sparkle. So, go back to your desktop for a sec, show us the organization scheme that you have.

Brandon Gell (01:51:11)

Alright. 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 like recently added to a folder stays there for three days. The manual library is like this place that you can use if you don’t want Sparkle to organize your folders. So if I’m like, if my taxes are really important and I do a good job of organizing them, I’m going to create a folder in the manual library and then just organize my taxes manually. And the other thing that Sparkle does is if you already have a bunch of folders on your computer, it will automatically put them in a manual library. So we don’t mess with those. And then the AI library is like this magical place where I have had thousands of files on my desktop and now they’re just magically organized in my AI library. So I’ve been dogfooding Sparkle for months and I’ve had countless experiences of needing to find something that’s really obscure, opening up my AI library and being able to find it super quickly. So, I mean, it’s pretty sick. It’s definitely, I mean, I find it super effective for desktop and especially for downloads.

Dan Shipper (01:52:39)

Yeah, it’s pretty amazing. It’s great. And yeah, I’m one of those people where it’s just that 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, I’m just bad at organizing stuff. And so that’s why I started Superorganizers because I was like, I want to learn how to do this. You know, sometimes you turn your weakest trait into a skill or a thing that you’re obsessed with because you’re bad at it. And I actually built the first version of Sparkle four years ago for that purpose, but it was all manual. And I used Tiago Forte’s— He has this system called Para. I use Para to as the base organizational system.

Brandon Gell (01:53:40)

Which by the way, he uses Sparkle now, which I feel like is the ultimate vote of confidence. He is the organization guy. And now he uses Sparkle to organize.

Dan Shipper (01:53:53)

He at least tweeted it. I’m not sure whether he uses it. He might or might not, but at least he’s a Sparkle supporter. I’ll say that. And when all the AI stuff started happening, I was kind of like, well, maybe it’d be cool to just redo it with an 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 built it and 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 once you install it, you don’t have to think about it ever again, but you feel it every day when you use your computer, and I love that. It’s such a good feeling.

Brandon Gell (01:54:39)

I mean, that is a special type of product that you don’t actually need to engage with for it to deliver value to you. And that is, I think, something that we will continue to try to search for in the products that we build.

Dan Shipper (01:54:55)

So this has been an incredible episode. I’m so glad that we did this. 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. Honestly, this is so much fun. I feel very, very lucky to get to do this with you.

Brandon Gell (01:55:20)

Yeah. Likewise, it’s bringing me back to my radio days of college.

Dan Shipper (01:55:26)

 

You’re good at it, man. I can tell you’re a radio guy.

Brandon Gell (01:55:29)

Yeah. Thank you for having me here. This is cool.

Dan Shipper (01:55:32)

Of course. Alright. See ya.

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Thanks to Scott Nover for editorial support.

Dan Shipper is the cofounder and CEO of Every, where he writes the Chain of Thought column and hosts the podcast AI & I. You can follow him on X at @danshipper and on LinkedIn, and Every on X at @every and on LinkedIn.