There's this whole wave of writers who are leaving their publications, and that's really good for writers. You can make more money, you have a lot more creative freedom, a lot more control over what you do. But there's a lot of downsides to that. So, one is it's like really lonely. Two is there's only a certain kind of writing you can do when you're by yourself because you have to produce a certain amount a week in order to just build your audience.
I feel like you're telling me why my job is bad right now.
Welcome to the General Podcast, the show where there's no host, no script, just the best builders talking about what they do and why they do it.
I have always, I've just been watching you from afar in a non-creepy way, and you just seem really talented and I've always wanted to get to know you. So, I sort of jumped at a chance to get to chat. For me, this is really cool because I remember talking to friends in media years and years ago, even pre-COVID, about wouldn't it be fun to do some sort of media collective, something like that. And so then we were sort of like, oh, Every is just that. But you've evolved since then, and now I follow you for how to use AI tools, kind of where the puck is going with AI and media. And sometimes I feel way out of my depth, but I feel like just following you and what you're building is like a cheat sheet for me about how far behind I am there. So this was a delightful opportunity for me to just learn from you for an hour.
That's amazing. I love to hear that because that's exactly like how we're trying to position the coverage that we do, and so that it's coming through means a lot.
Well, it is interesting. You know, we come from very different backgrounds. You obviously did a startup before this. I'd say you have more of that coder background whereas I really have a media and Indiana Jones attempted career background. So very different. Happy to explain that.
I would love to know what that means.
Yeah. Well, for me it was basically that in college I thought I should just create a major around being Indiana Jones until I realized that that person today would just go to jail immediately. And so not a great career option, but I did do Latin archaeology, medieval history, all the useful stuff for covering AI, you know.
Did you go on any adventures?
I dug up Harvard Yard, which was great because tourists would come and try to fall into this pit that we were digging to find the oldest knocked-down building at Harvard years ago, which we did, which was cool. And I also went to the Middle East, to Egypt and was trying to go to Syria right as the Arab Spring was starting. So, it was not a very safe time. And that was also part of my contribution to maybe I should career pivot. But yeah, very unusual background. So, I think get into AI. I'd say you come from much more that classical tech background.
How did your journey take you from like startups to a difficult area like media?
I've really always loved writing and I started out wanting to be a writer. So, when I was in third grade, I was like, I'm going to be a writer. I wrote a novel, 100-page novel.
I don't think it had a subject.
It's the best. It's very modern.
Yeah. My mom still has it, but I was very focused on having it be 100 pages. That was like the mark of a real book for me. And then I decided that I didn't have enough life experience to be a writer at that point. And so I needed to go out and have more experience before I could go back to writing. So in fifth grade, I read a Bill Gates biography and decided I wanted to start Microsoft or a Microsoft competitor. I was going to name it Megazoft. And that's how I started learning to code. And so like programming and business and tech and then writing have always been these sort of dual threads for me.
Were you like a super cool kid in high school?
I was extremely cool. Can't tell. Yeah.
So was I obviously, super popular.
And no, I felt kind of like I was always off to the side a little bit. So I channeled my not being cool enough into working really hard. And that was actually good. It required a lot of therapy to change that approach to things. But for the first like 15 years of my life from 10 to whatever 25, it was very useful.
And then when did you become an actual entrepreneur versus Bill Gates's next competitor?
So I started building like lots of little apps in high school. I was really into making BlackBerry apps. This is before the iPhone came out. So I was like, I was team BlackBerry.
Really? Did you have a BlackBerry Pearl?
Yeah. So, I was building stuff for BlackBerry Pearl. And that's basically how I paid for gas and food in high school is just like selling apps on the internet. And then in college I was a philosophy major. But I started this company called Firefly which ran that for a couple years, was all bootstrapped, and then sold it to this company called Pega. It's a big public enterprise software company right as I graduated. And so that was the first thing I did that turned into a real company. Had real customers, we had employees, all that kind of stuff.
That's cool. Meanwhile, in college, I was an arbitrage of a startup. I actually, I kind of blocked this out of my memory, and I forget that this happened a lot of times, but I actually did work for a startup in college, and it was a test prep company, kind of a multi-level marketing scheme.
The founder, who among us has not worked for multi-level markets. The thing is it actually got acquired and the founder did well and then later co-founded Thrive Market which is like a real venture-backed commerce startup but he got his start there. The arbitrage was they went to Ivy League college students and they convinced them to be like regional managers of this test prep company where the students would have to basically put together a curriculum, find a classroom, do all this work to do SAT tutoring and then take home maybe 10%. And the startup took the vast majority of the money. And so I worked on this for two summers and I thought I was making good money. And then later I realized how much of a margin we were creating and I was like, 'Huh, that's how that business got.' So wasn't an entrepreneur, but I learned the hard way about value capture.
Yeah. Yeah. That's interesting. And how did you get into journalism, get into writing? For me, it was that storytelling is something I've just always really loved to do. And thinking kind of practically, I was like, how can I get paid to do this thing that I think I'm good at and that I enjoy. And writing the great American novel, being a struggling novelist, was not really something I felt cut out to do. There's a line, I think, in the most recent season of White Lotus on HBO where she's like, you know, I'm not made to be poor or something. For me it wasn't quite that bad, but I definitely am like a slightly risk-averse person, which is funny that now I'm a founder taking on all the risk because I was sort of thinking very practically like where can I just make a living, get paid. I was living at home at first, making nothing. But so, magazines actually paid writers and so I got a job at Fortune magazine and then tech was an area that I just thought would be growing. I didn't want to do politics and I was like tech and politics seem like the areas where there will be a lot happening in the next 10 years and most tech reporters were in the west coast so sort of like oh I can cover New York startups so I was covering Foursquare, Blue Apron, General Assembly, Zocdoc, you know, all these companies. That's kind of how I cut my teeth.
That's really interesting. Yeah, I remember that era of New York tech because I was in college at that time and I was like shuttling into New York to like hang out and like check in on Foursquare and talk to all my friends that were like the mayor on was a big deal.
Then I kind of got to zoom out and cover startups more nationally. But I think finding a niche and really doing well in it was something I learned from that for sure.
Yeah. And what did you feel or what did you learn in that era of tech and like why did you decide to like double down on covering it?
That's a good question. I think you know the New York scene was very optimistic, kind of naive, and I think actually like a healthy way for startups. You know, one of the things I learned when I started covering venture capital was a lot of VCs would say, you know, we need a founder to almost have blinders on to not know how difficult and hard this will be. And sometimes, you know, you would talk to a founder who had sold an adtech company and they were like, I never want to work in adtech again because I know how difficult this area is, right? And so I think for me when I was meeting these founders like there was a naivete to the New York scene that I actually just found really wholesome and like everyone was supporting each other. I think now the New York scene is much more sophisticated. I do think there's a little bit more of that humble or collaborative vibe versus when I go to Silicon Valley and I feel like everyone's almost like too optimized and too transactional. So I'd say that was what I loved about the New York scene. There's definitely room for weirder stuff here. I think or weird in a different way than like I think there's a lot of amazing stuff going on in San Francisco obviously, but the shapes of the kind of businesses you run into, there's a lot more non-standard shapes here, which I like.
Well, speaking of weird, one of the most classically non-venture-backable businesses is a media company. So, how do you end up launching Every five years ago?
So basically like I sold my last company. I spent a while kind of just like figuring out what I wanted to do with my life. I traveled the world. I wrote a novel, another novel which I did not release.
But does your mom have that one as well?
Google Drive has that one. That one didn't make it to my mom.
I worked at an incubator. I did some more like angel investing, pre-seed investing, and eventually I was like, 'Fuck it.' Like I'm just going to start another company. I want to start another company. I've always been like a tools for thought, organizing what you know type of nerd and so I was like I want to build software to do that. And it was sort of like inspired by like Roam or Notion. And before I started I was like I want to do some customer interviews to understand how really smart people are like organizing themselves to do their work. How do they take notes? How do they do their to-do list? How do they do their emails? All that kind of stuff. So I can figure out how to build the thing I want to build. And I needed a hack to get interesting people to get on the phone with me because if you talk to someone smart and you're like, hey, I'm building a new product. Can I interview you about your day, they're like, why would I waste my time with you? So I was like, I'm going to start a newsletter. And I'm going to say, I'm interviewing people for my newsletter. It's going to be called Super Organizers. I'll actually write the interviews up because I really like writing and that'd be really fun, but I'll use what I learned to build software that I can then sell to the audience. And so I started doing that and it started growing and I was like, whoa. Like maybe I could just do a newsletter business. Like I love writing. That'd be super cool. It was at the very beginning of the creator economy, Substack wave, which I didn't know at the time. And so I started talking to my co-founder for Every, Nathan Baschez, who was the first employee at Substack, and we started working together. We were both writing our own newsletters, and then we decided to bundle them. And that was the sort of genesis for Every was there's this whole wave of writers who are leaving their publications, and that's really good for writers. You can make more money, you have a lot more creative freedom, a lot more control over what you do. But there's a lot of downsides to that. So one is it's like really lonely. Two is there's only a certain kind of writing you can do when you're by yourself because you have to produce a certain amount a week in order to just build your audience.
I feel like you're telling me why my job is bad right now.
I've lived it, man. Like you will feel emotionally drained.
Your name is Alex. You don't sleep enough. You can't take vacations.
But continue. Yeah. Yeah.
Put the nails in my coffin. And it's also in some ways not as good for readers because you have all these separate places you have to subscribe to. You have to pay multiple subscription prices. And so we were like what if we could build a publication or a bundle of publications that was a little bit more internet native. So we could figure out an economic scheme to get a bunch of writers together so that readers pay one price and they get access to all the writing that those writers make. But then we also figure out how to share revenue so that as you do better as a writer you make more. So it solves some of the problems with more traditional publications that led to a lot of writers wanting to leave. And so that was the original impetus for Every. So we've always had this writing and product thing going on where we're, I think a lot of the best writing about business and technology if you have your hands in the technology and you're building stuff with it lets you write from a particular perspective that I really like. And so we've always been building like little products and little things that we've launched to the audience alongside the writing. And that's sort of blossomed into the thing that we have today. And there was a lot of stuff in between there that did not work and was like completely bad that we've gotten rid of. But that was the idea.
Do you think of Every today more as a media company or a software business where media is, you know, one of the arms of the company?
I usually say media and software company. So the media comes first. Sometimes I say multimodal media company. So it's like software is one of the things we publish. We publish writing, we publish videos, we publish podcasts, and we publish software. Because I think that we're in this era where like what it means to be a writer and what it means to be a builder is sort of starting to merge a little bit. And I think to me the soul of what we do is always the media thing and everything comes out of that. So I think the media is the core.
Yeah. You know, obviously you got this awesome spread in the New York Times and I was like, you know, I mentioned to you I thought it was fascinating. You know, there you are in your glamour photo on the staircase, you know, looking up at all the possibilities. But I was thinking to myself, okay, you know, a great classic AI investor like Reid Hoffman, what makes him excited about Every? Is it the blend of the two things? Is it really the software tools that you guys will unlock over time? And if we check in years from now, will that mix look radically different than it does today? So, I was really curious to hear how you thought about that.
So, we raised in a sort of weird way where we raised up to 2 million, but we can pull down that money as we want. So, we've not pulled down all of it. And I wanted to do that for a very particular reason, which is it's much cheaper to build stuff now. And I care a lot about the kind of business that we build and I don't want to put pressure on Every to look like a certain kind of outcome. But I do want to have the money to explore. And so we were looking for investors that sort of had that same mindset or were okay with that. So Reid, for example, did not invest out of Greylock. He invested personally. And I think for him in the core of it is we're very philosophically aligned in the kind of world that we want to build. I think he's thinking a lot about AI and a lot about how to make AI better for humans, build a better human world with this new technology. And I think that that's the question that we ask ourselves and think about and try to answer every day at Every in the writing that we do and in the software that we make. And so I think for him, I'm sure he would be delighted if we like 100x'd his investment or whatever. But I think for him, he's more interested in the impact that we can make on a cultural, philosophical, ideas level, and the money is awesome, but not the main thing.
That's great. That's like an intellectual investment, not just a VC one. We know those are not always the same thing. Yeah, it's also interesting for me because when I was setting out to start Upstarts, a lot of VCs did reach out. Some wanted to just invest personally more like Reid in whatever I was doing. They didn't almost care what it was. And I do feel like this is also Silicon Valley where people can be a little transactional and it's sort of like I want to show my support for you and what you've done so far. So can I, you know, where do I wire the money? And you're like actually just subscribe and be part of the community for now.
Yeah, exactly. I don't want 20K. I want $500.
Which of course makes a lot of sense to a VC mind. It does not. But, the other interesting thing was a lot of VCs were like, 'Cool. So, how are you building the software tool here?' Like, great, Upstarts will be a media company and that's fantastic, but when do you start the recurring revenue building tools for other creators? And it was like they were immediately thinking that that must be the goal.
Yeah. Because if you want to build, if you're ambitious, you want to build a big company. If you want to build a big company, you need software. You need recurring revenue. And so for me to say, oh, for now, I actually don't want to do that. Was kind of like a weird conversation to have.
Yeah, I felt the same way. For many years everyone was like, so when are you going to like do something real and not just a newsletter? And yeah, because I think there is like one particular way of being ambitious that most people in tech think about. And I feel very ambitious but the shape of that ambition is different and the pace of it may be a bit different and I think over time Every has grown into this thing that has a shape that would be completely unintelligible if I was like I want to do this like it's a media company but we do software and we have a consulting arm and like it just doesn't make any sense. It's too weird, but it actually just works in this way that I think breaks the mold of a lot of typical tech narratives, but also there are a lot of other businesses that work this way. They're just more creator-run type businesses and I've learned over time that that has a particular shape and there's a certain type of person that understands that and wants to build that kind of company. So, you're in good company. I know exactly that feeling. How are you thinking about what you want to build and how to go about it?
Yeah, I think for me the inspirations that are most relevant from a business standpoint are more the bootstrap companies that I've spoken to. And some of these companies go 10 years bootstrapped and then they raise the huge round and so by the IPO maybe they look like a regular tech company but for 10 years they were building more modularly. I think for me my growth looks more linear and like direct correlation between time I put in and output I'm getting. I think you know so many startups are basically thinking either we're going for product-led growth and we're going to create that hockey stick with like minimal external effort. We're just focusing on our product. And then of course they're the startups like Figma where they spent a couple years tinkering, losing money, and had to basically be dragged to charging for their product in the first place. I obviously can't do that, right? Like I can't be two years without revenue. And I also think that when you're in media, when you are closer to that creator, and I do think independent journalists are a subset of creator, that is a surprisingly controversial take with some of my peers, but I do believe it. I think for us, we are the output in some ways. You know, we are closer to that tech-enabled services business than we are the pure software play. And so like Mailchimp, I wrote a big story about the Mailchimp CEO and there was a lot of the story actually went way more viral than I expected because maybe this was also like peak podcast and so Mailchimp was advertising on every podcast and people knew it that way. But I was like surprised that this guy Ben Chestnut in Atlanta got so much attention. I think it was though the way he'd built kind of that modular approach really resonated with a lot of folks. And so that to me is sort of my thinking is like do the startup things that don't scale but also be really close to how the business is performing. Like I get a push alert from Substack when I get a new paid sub.
It's a nice feeling and it also like if I go a couple days without any it's also a nice reminder too, you know.
Yeah. Yeah. Totally. No, that makes sense. I do think I have a slightly different take on the is media or is being an independent writer like a tech-enabled service type thing in the sense that there's a specific fixed cost that you have to pay in terms of your time to just make a newsletter that anyone wants to subscribe to but that does not change as you scale. So, like Ben Thompson, for example, is probably working the same hours as he did when he had 500 subscribers or maybe the same hours as you, but he makes like $7 million a year or whatever the number is, which I think is a really cool aspect of being a newsletter writer is if you can get that formula right, the same output has a much bigger impact in terms of your revenue or your growth when you're like 5 years in or 10 years in, it starts to compound.
And I totally hear that. I think Ben is probably the gold standard. I think Lenny's newsletter, Lenny Rachitsky would be another person. Gergely Orosz with The Pragmatic Engineer. These guys have all built huge audiences that way. I think for me, I'm a little bit trying to speedrun several different products. They're just not software products like maybe you have. So for me, the newsletter is the most important thing.
But I want to ship my own podcast in the fall. I've already been doing a bunch of events and that's where I think it can feel a little more servicey where I threw an event in New York recently, also in London and each time you throw an event, there's just a lot of crunchy stuff to deal with.
Could I hire to have someone manage that over time? Absolutely. But for now, I don't think it's repeatable and I'm so much the brand that like I just have to do those things.
That makes sense. That makes a lot of sense. How has it been going from having a job to being on your own? Are you saying I don't have a job anymore?
No, you don't have a job. No, I as someone who doesn't have a job either, you don't have a job.
I have five jobs. None of them pay me any salary right now. So, I got to figure that out. It's been an interesting adjustment. I'd say the most positive adjustment for me was to really embrace that sort of founder cliche that you are running your own race.
I think that, you know, when I was at Forbes, I am an extremely competitive person. I played hyper-competitive chess growing up until I realized I would not be an adult champion.
Yeah. Yeah. Chess is a lot like basketball where you just end up not tall enough compared to other people. In chess there was just the processing power where I could see five, six moves ahead and once my peers at the very top started to see 20 moves ahead I was like okay I'm not going to be a chess master. In journalism though, especially covering VC and startups, I felt like, you know what, actually I do have room to run to be the best. And I felt so competitive. And so I would be the person on Slack at 1:00 a.m. messaging my West Coast colleagues like, why aren't we on this story? Or like, how did we let Bloomberg get that story? You know, and the minute that I stepped away, it was sort of like that receded because I realized I'm writing eight stories a month. I am building a company. I have to like focus on all these other things. I just have to let all that go, right? And I can be successful building something new in a way that isn't taking away value from somebody else, you know? And so for me, that was the weirdest thing was like the actual positive sum mindset. I'm curious if you've always felt that too or positive sum like not like you're adding something versus taking share from some other.
It's a good question. I will say the push back I get to that is that everyone has limited attention.
