Dan Shipper — I, Writer (EP.237)

“Ignoring what is obvious incurs a huge cost.

It requires you to go about your day numbing yourself to the reality of who you are and what you want—which is a waste of time for you and everyone around you.

By contrast, admitting what is obvious is freeing and motivating. But it’s terrifying to do it. Sometimes the most obvious truths about ourselves are hard to see because the consequences of those truths seem so dire.”

Those are the opening lines of one of my favourite essays I’ve read in the last year, written by this week’s guest on Infinite Loops - Dan Shipper.

Dan is the Co-founder and CEO of Every, a media company that wants to be an intellectual lighthouse amidst the tempest that is the Age of AI.

Every began life in 2020 as a bundle of digital newsletters (almost like a centralised version of Substack with more of an editorial flourish). These days, it’s blossomed into an ecosystem of colourful newsletters, podcasts, courses, and software products, all oriented around the unpacking of a single question - “What comes next?”

Every is already one of my go-to destinations for all things interesting. It’s less brain food than brain buffet (the kind of buffet that serves fresh blueberry pancakes with real maple syrup).

In our conversation, Dan shares his thoughts on everything from AI companions; his approach to erecting the Every ‘Pyramid’; his playbook for building new media companies; the idea of LLMs as mirrors for humanity; and using content to ‘find your people’.

What I love about him is how candidly and thoughtfully he talks about his journey to discover his own truth. His realisation that he didn’t need to hang up his boots as a writer in order to become a founder is something that particularly hit home for me.

Dan Shipper is also my underdog pick to eventually wrest the title of Infinite Loops Emperor from reigning clubhouse leader Alex Danco. By which I mean to say, this is most certainly not the last time Dan joins us on the show, so you may as well get to know him better.

For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

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