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Dan Shipper: belief

17 Jul 2025 Lenny's Podcast The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every)

“What it really is, is there's a huge tax to doing something every day that you don't quite like that much, or you're not quite a fit for, and by sort of giving into those secret desires, you end up finding a shape for the work that you do and the business that you build that is good for you, and that's always going to be a somewhat unique shape from other businesses that have been built. It's always going to rhyme with other things, but I think finding that unique shape, instead of just kind of cargo culting, like what you think a company should look like is definitely a much better way to be successful, and it's also a much better way to live.”

— Dan Shipper

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Everything needed to verify it.

Speaker
Dan Shipper
Attribution
Verified speaker
Claim type
belief
Recorded
17 Jul 2025
Publisher
Lenny's Podcast

Transcript context

…I think generally, when you're building a company, even if you do it the way that I do it or did it, which is you don't raise a lot of money and you try to stay in control, there's a big temptation to try to run the company in the way you think you should. And I have this weird thing where I'm like, "I really love writing, but I also really love business," and there were not a lot of models for me of people who had successful businesses that were also writers. It turns out there are, but I didn't know about that for a while. And so early on at Every, it was growing really well, because I was writing a lot, and Nathan was writing a lot. And when I stopped writing, the business didn't work as well because media businesses don't follow the same pattern as tech startups, because if you're a media business and you are a founder who then hires people to make the product, which is right, if you have product market fit before, you lose it, and maybe you hire people that are good writers, but that's hard. It's total opposite pattern for startups. So you build the first version of the product, and then you hire people to build the rest of it, and so that's what I did. And I also really struggled with, "Okay, what are the implications for that and for my career," and I think it was hard for me to admit, like I actually want to write because I just didn't have any examples of someone being the kind of writer that I wanted to be. And what's really interesting is three years into the business ... The business has been pretty flat. I was pretty miserable because I was not doing the thing that I really wanted to do, and I asked ChatGPT, I was like, "Are there any examples of writers that have built businesses?" And it was like, "Yeah, Joel Spolsky, who built Trello and Stack Overflow. There's Jason Fried who I've known for a long time, and I've always looked up to, but I forgot about in this context. There is Sam Harris who's got a great podcast, and he's got a gigantic meditation app. There is Bill Simmons, who's incredible podcaster and also built The Ringer, sold to Spotify for a couple hundred million bucks. There's a lot of these people, and there are patterns that they use to build companies that are pretty well-understood. They're just not typical Silicon Valley patterns. And so I was like, "Cool. I just want to be a writer. I think it'll be really fun." And so I sort of flipped. I still have the builder, entrepreneur, founder part of my identity, but I sort of flipped it to be like writing is at the center, and I'm unapologetic about it, and that's actually good for the business. It's good for me and it's good for the business. And the more I've leaned into that, doing the thing that ... If you told anyone that you're starting a business, where it's like, "Well, we're going to be a newsletter, and we're going to incubate all these apps, and we're going to do consulting and whatever," they would be like, "You're nuts." "Everyone wants to do that. like, "Well, we're going to be a newsletter, and we're going to incubate all these apps, and we're going to do consulting and whatever," they would be like, "You're nuts." "Everyone wants to do that. Of course, Every founder wants to do that, but you have to focus. You can't write, whatever." But every time I've kind of just leaned into something that feels like the most, the ultimate luxury of my hidden secret desire, it's actually worked a lot better, and I think you end up ... What it really is, is there's a huge tax to doing something every day that you don't quite like that much, or you're not quite a fit for, and by sort of giving into those secret desires, you end up finding a shape for the work that you do and the business that you build that is good for you, and that's always going to be a somewhat unique shape from other businesses that have been built. It's always going to rhyme with other things, but I think finding that unique shape, instead of just kind of cargo culting, like what you think a company should look like is definitely a much better way to be successful, and it's also a much better way to live. I think this is going to hit hard with a lot of people who are listening, who are maybe founders or want to be founders, and this resonates with a lot of people that have been on this podcast sharing similar lessons. Dan, this was incredible. Two final questions. Where can folks check out Every, find you online, and how can listeners be useful to you?…

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