The Company Where Everyone Has Their Own AI Agent

Summary

WHAT'S YOUR PROBLEM?
Episode: "The Company Where Everyone Has Their Own AI Agent"
Host: Jacob Goldstein
Guest: Dan Schipper, Co-Founder and CEO of Every
Date: May 21, 2026

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Overview

On this episode, Jacob Goldstein speaks with Dan Schipper, CEO and co-founder of Every—an AI-focused company where nearly every employee works alongside their own personalized AI agent. The discussion dives into the logistical, social, and creative aspects of integrating AI agents into daily workflows, exploring both their current and possible future impact on work, writing, and personal reflection. The episode splits into two main topics:

1. How Every built a company “where almost everyone has their own AI agent,” and
2. Whether AI augments or threatens the craft of writing.

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Key Discussion Points & Insights

1. The AI Agents at Every (00:00–14:29)

• What is Every?
  Every is an AI-powered company that publishes AI newsletters, builds AI tools, and consults businesses on AI integration.

• What are "claws"?
  Employees at Every have their own AI agent, called a “claw” (named after the open-source OpenClaw AI).
  These are accessible via Slack and can be customized with names and personalities.

• AI Agents as Evolving Coworkers

  • Claws adapt to user's habits and needs:
    “As you talk to it, it is evolving with you and building functionality for itself to make it good for you and the things you do.” – Dan Schipper (04:22)
  • They take care of recurring tasks, such as compiling lists, summarizing issues, or even saving and explaining things found during reading sessions.
  • Example: Dan’s agent, R2C2, maintains his to-do lists, explains reading passages, and acts as a thought partner for brainstorming.

• Claw-to-Claw and Claw-to-Human Communication

  • Claws take on some of their owner’s responsibilities, building trust and reputation within the company.
    “The editorial team just started immediately being like, ‘@Montaigne, how did this essay we published do?’ So now Montaigne is the guy, where Austin used to be. But now it's Montaigne.” – Dan Schipper (08:43)
  • The human owner is responsible for maintaining their claw, moving their role toward a management layer.

• Messy Realities and Group Dynamics

  • Claws sometimes "chime in" at the wrong times, not picking up on group social cues.
    “They only know about one-on-one conversation. They don’t really know about, ‘I’m in a group environment, here’s how you act in a group environment.’” – Dan Schipper (11:21)
  • Dan built a plugin called “Tact” to teach claws when not to respond.
    “Now it runs Tact before it responds... It makes it much better. It’s not perfect, but way, way, way better.” (11:47)
  • Complexity comes from subtle, tacit knowledge—hard to encode in training data.

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2. Resistance and Cultural Shifts (14:30–18:21)

• Not Everyone Wants Their Own AI

  • Some employees, despite the pro-AI culture, are reluctant; reasons include personal preference or boundaries with technology at work.
    “[Some say] I want to do my job well, but I also just want to go home. My thing is not playing with new technology...” – Dan Schipper (15:34)
  • Overcoming resistance involves showing practical, personal use-cases to trigger "aha moments."

• External Pushback

  • When consulting outside companies, resistance is stronger—fear of redundancy, “creepiness,” or perceived loss of meaning/purpose.
    “For people... really against it... sometimes it’s just not a thing that you can ever convince someone. And I think that’s fine.” (16:15)
  • Some change their minds after seeing genuinely creative or helpful uses of AI.

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3. Writing: Augmented or Replaced? (18:22–34:45)

Theme: Will AI make good writers obsolete? Does it threaten the ego and identity of creative professionals?

• The Craft of Writing & the Limits of AI

  • Good writing is inherently personal, built from countless minute, individual decisions.
    “A really great piece is full of all these little tiny decisions that are yours... It’s super individual.” – Dan Schipper (21:46)
  • While AI can output remarkable copy, experienced writers quickly spot repetitive, “sloppy” AI tics—demonstrating that true writing expertise still outpaces the models.

• Learning and Adaptation

  • Humans adapt their voice and thinking faster than models can be retrained; even with personal fine-tuning, the gap persists.
  • Even if AI could perfectly mimic a writer, it would be more like an 'identical twin':
    “Even if you hypothesize an AGI that knows all about you, it will have a fundamentally different perspective because it’s different from you.” (23:34)

• Status, Market Shifts, and Ego

  • As AI writing proliferates, human-crafted work may become higher-status, more “artisanal,” and niche—even as the mass market moves toward AI content.
    “What tends to happen [with older art forms] is they become higher status, more expensive, more artisanal, and smaller market.” – Dan Schipper (26:21)
  • Personal relationships and human touch may become key differentiators.

• A New Kind of Optimism?

  • Daniel frames himself as neither AI-hyperoptimist nor doomsayer, but as someone seeking to use AI thoughtfully for creative and meaningful work.
  • He accepts job disruption as real but pushes against fatalism and technophobia:
    “What happens when you reach the horizon is you find another one… There’s always going to be good things and bad things over the horizon, and probably in similar proportions to what we have now.” (35:20)

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4. AI as a Creative & Reflective Tool (38:56–46:17)

• How Dan Uses AI in Writing

  • Reading workflow: Uses AI to save, summarize, or explain reading passages, including translating Russian lit or unpacking tricky lines.

  • Idea development: Dictates voice notes, then asks his AI to help articulate and organize thoughts.

  • Drafting: Asks AI for openings, metaphors, or summary passages (“Here’s what utilitarianism is—in three sentences.”)

  • Editing: AI is used for initial edits, style checks, and removing AI-isms; human editors are still crucial.

    “I can do much more ambitious pieces... more frequently and with less time.” – Dan Schipper (31:51)

• Mirroring and Self-Understanding

  • Dan fed his therapy session transcripts and personal journals to GPT-3; the AI surfaced honest insights he and his therapist missed:
    “It sounds like you feel really overwhelmed… and it just like fucking broke me. It was true.” (43:15)
  • Even today, he uses AI to help articulate feelings, especially in challenging interpersonal situations.

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5. Lightning Round: Hot Takes and Anecdotes (38:56–46:17)

• Argument with AI:

  • Dan is stern with his agent when it skips logical steps or introduces ideas he disagrees with.

• Spiciest AI Take:

  • “Automation is a lie.”
    • Keeping an agent “alive” is work; it demands ongoing stewardship, updates, and human oversight.
    • “Keeping an agent running is a job... The view of automation as ‘set it and forget it’ is just not true.” – Dan Schipper (40:36)

• Morality and Manners with AI:

  • There’s debate over whether to be polite to AIs; interesting research suggests being “mean” can yield worse results.

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Notable Quotes

• “As you talk to [your claw], it is evolving with you and building functionality for itself to make it good for you and the things you do.” — Dan Schipper (04:22)
• “If you have a relationship with your claw, it becomes good at the things you’re good at… You’ve transferred some of your reputation and trust to your claw.” — Dan Schipper (08:18)
• “The skill of the future will be learning to manage agents, allocate intelligence.” — Dan Schipper (09:32)
• “A really great piece is full of all these little tiny decisions that are yours… It’s super individual.” — Dan Schipper (21:46)
• “The things that are old become high status, more expensive, more artisanal, and a smaller market.” — Dan Schipper (26:21)
• “Automation is a lie.” — Dan Schipper (40:31)
• “What happens when you reach the horizon is you find another one.” — Dan Schipper (35:20)
• “These things are really good at articulating stuff that you’re kind of dancing around or it’s kind of latent in there, but you haven’t fully said.” — Dan Schipper (44:21)

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Important Timestamps

• [02:17] — Intro to Every and episode themes
• [04:22] — How AI agents (claws) work, their personalities and abilities
• [08:18] — Building trust and reputation with AI agents
• [09:32] — The new skill: managing agents
• [10:22] — Social awkwardness of agents in group communication
• [11:47] — Building “Tact” plugin to moderate agent output
• [14:29] — Cultural resistance: why not everyone wants an AI agent
• [21:46] — Why good writing is inherently human (vs. AI)
• [26:21] — AI impacts on creative industries; “portrait painter in every town” analogy
• [31:46] — How AI changes Dan’s creative output
• [40:31] — “Automation is a lie”—the myth of frictionless AI workflow
• [43:15] — AI surfacing deeper insights from Dan’s therapy sessions

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Final Thoughts

This episode provides an insider’s look at a workplace already experimenting with a “future of work” scenario where human-AI collaboration is the norm, not the exception. It illuminates practical realities, philosophical dilemmas, and the changing nature of creative work in the age of AI—acknowledging both the excitement and disquiet of the new frontier. Dan Schipper stands out as a thoughtfully critical optimist: not selling utopia, but neither buying into fear.

Transcript

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[Jacob Goldstein]

Pushkin. I'm Jacob Goldstein and this is what's your problem? My guest today is Dan Schipper. Dan is the co founder and CEO of a company called Every. Every publishes newsletters about AI. They develop AI related software, and they consult to other companies about how to use AI. So what I'm saying is Every is an AI company. And when Dan describes Every's work culture, he says, we live in the future. Which means that people at Every use AI in ways that lots of the rest of us will soon be using AI. Given that context, there were two specific problems that I wanted to talk to Dan about. Problem number one, how do you build a company where almost everybody has their own AI agent working alongside them? Problem number two, how do you use AI as a tool to improve your writing rather than as a replacement for writing one's particularly close to my heart. We talk about problem number two later in the show. Regarding problem number one, I will say almost everybody at Every has their own AI agent. And specifically they use this popular open source software called OpenClaw.

[Interviewer (Host)]

You may have heard of it.

[Jacob Goldstein]

It's basically an AI assistant that you communicate with via Slack or via text. And at Every, they give their claws names. So Dan's claw, for example, is called R2C2 and R2C2. And the other claws are on Slack, just like the human beings who work at Every. So I wanted to know, well, a

[Interviewer (Host)]

lot, really, I wanted to know a

[Jacob Goldstein]

lot, you know, what do the claws do? How do they interact with the humans, what works, what doesn't work, what is super weird? And just what are the claws?

[Dan Schipper]

Like, what's really interesting about them is that they have personalities. So you give them a name, they give them a little bit of a personality. They modify themselves in response to your messages. So when I say, hey, go do this thing, it starts to realize, okay, I'm going to be asked to do task X. And it will build things into itself, whether that's into its prompting or into little tools that it builds for itself to make it good at that. And so you're kind of, as you talk to it, it is evolving with you and building functionality for itself to make it good for you and the things you do.

[Jacob Goldstein]

Okay, so you have this agent, R2C2,

[Interviewer (Host)]

but tell me more about how it works.

[Jacob Goldstein]

I know you've talked before about how it helps you kind of manage this piece of software. You wrote this thing called Proof that a lot of people are asking you questions about. But just give me more information.

[Interviewer (Host)]

How do you actually use or work

[Jacob Goldstein]

with it day to day?

[Dan Schipper]

So, you know, an easy one is this morning he went through all of the issues that were submitted in Proof and then prepared a little document for me that was like, here's all the stuff that like has gone wrong over the next, over the last 24 hours and here's what I recommend we do. He also has a little document that he keeps, that's my to do list. So he pings me in the morning and is like, here's your to do list. He also, you know, one of the things I love to do is I always go to a restaurant nearby the office and have breakfast in the morning and read. And I will often take a picture of a thing and be like, hey, can you explain this to me? And he'll like explain it and help me think about it.

[Interviewer (Host)]

Does he text you back? Does he slack you back?

[Dan Schipper]

It's on slack. Yeah, it's all on slack.

[Interviewer (Host)]

So you slack him a picture of like a passage from a book.

[Dan Schipper]

He also keeps all my reading notes. So I'll say, okay then now save this. And I have a whole reading feed that is like all the stuff that I've been reading over the last couple months. I also just talked to him about ideas. So today I was, you know, just thinking through some, some deep, deep thoughts as I do about where we are in AI and where we're going and all that kind of stuff. And I just like Monologue is our, is one of our products as a speech to text app. I just took a note with Monologue, like a voice memo and just blabbed into it for a while and then started talking to R2 about what do you think I'm really trying to say here? Having something like this that can reflect back to you what you're saying.

[Interviewer (Host)]

Yes.

[Dan Schipper]

And put your finger on it is super valuable. Especially, especially if it's something that has is the equivalent of an expert on like pretty much any domain. It's not going to be perfect but like, you know, it's a good stand in for an expert and that to

[Interviewer (Host)]

be clear, anybody can do with any language model. Right. Like you don't need a cloth for that. That's like classic. Nice use of the window on any decent large language model.

[Dan Schipper]

Totally. It's just a little bit easier to like, I don't have to. He's just always on. So it's like it's just easier to like slack him in the way that I would a human.

[Interviewer (Host)]

It's amazing the way the tiny, tiny frictions. Right. Can make a difference even like your own mental frictions.

[Dan Schipper]

Yeah, yeah.

[Interviewer (Host)]

So, okay, so that's like one man in his claw. There's this other level which is like claw to claw and person to claw. Right. Like you have this company that is people and claws and, and the agents aren't just free agents. Each agent is sort of the doppelganger or whatever of a person. Tell me about that.

[Dan Schipper]

That gets really interesting because what tends to happen, like I said, is if you have A relationship with your claw. It becomes good at the things you're good at. And if you start using it in Slack, other people realize that it's good for the things that you're using it for. So you've transferred some of your reputation and trust to your claw.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

And so, for example, Austin, our head of growth, has a claw named Montaigne.

[Interviewer (Host)]

Hi, bro.

[Dan Schipper]

And he uses Montaigne for all of the numbers. So, like, how much did we grow? How many trials did this piece drive? Like, all that kind of stuff. And the editorial team just started, like, immediately being, like, at Montaigne, like, how did this. How did this essay we published do you. And so then it becomes this thing that feeds on itself. Where now Montaigne is the. Is the guy, Is the guy for this, where Austin used to be, but now it's Montaigne. And it depends, though, on Austin making sure that Montaigne is always up to date and working. But instead of answering the questions directly, he's working on the system that answers the question. So he's sort of like, moved up a level.

[Interviewer (Host)]

Yeah, he's managing like, the agent works for him. That's what a manager does.

[Dan Schipper]

Right.

[Interviewer (Host)]

Like, you make sure that the person who's working for you is, like, doing their job and answering questions correctly.

[Dan Schipper]

Yes.

[Interviewer (Host)]

And is happy. And with the agent, you don't have to worry about that.

[Dan Schipper]

Yeah. Which is really fun for me to see because I wrote this piece like three years ago called the Knowledge Economy is Over. Welcome to the Allocation Economy. And the idea was the skill of the future will be learning to manage agents, allocate intelligence. And it's starting to be a thing now. It's really interesting to see.

[Interviewer (Host)]

You're going to write a piece now that's headlined I was right.

[Dan Schipper]

I was right. Give me credit.

[Interviewer (Host)]

Suck it, haters. I want to go back to the company and multiple clause, because you gave this sort of tidy thing of. They used to ask the guy, now they ask his agent. Surely it is more complicated and interesting than just that. It must be hard in some ways. It must be weird in some ways. You must be figuring things out. You must have gotten something wrong.

[Dan Schipper]

Yes, yes, yes, yes. One thing that I really love is they sometimes don't know when they should or shouldn't respond. And they're sometimes or often too chatty. For example, you might tag a claw and ask it a question or ask it to do some work. And then in that thread in Slack, one of your coworkers might say something, but it was not directed at the claw, it was just a comment on what the claw was doing. And, and then you're trying to respond, but then the claw jumps in and is like, yes, you're totally right or whatever. And it's like, dude, this is because

[Interviewer (Host)]

it's like there's a chatbot underneath it. And it's so hard for a chatbot not to reply when they're. Is that basically what's going on?

[Dan Schipper]

Basically. But I think the way that I think about it is these chatbots are trained. They only know about one on one conversation.

[Interviewer (Host)]

Uh huh, uh huh.

[Dan Schipper]

They don't really know about. I'm in this group environment. Here's how you act in a group environment.

[Interviewer (Host)]

Interesting. Which is so much subtler and harder. Right. Like all the cues that even change from context to context for people, from work to home, from one job to another job, depending on what your role is in a particular group. Are you the guy whose role is to talk a lot in this group or to not say anything in this group? That is a super subtle one.

[Dan Schipper]

It really is. And you're never ever going to message ChatGPT and have it not respond. It just always responds. And so I built this Little plugin for OpenClaw called Tact that took a bunch of examples of instances where my claw and a couple other people's claws responded when they were not supposed to in ambiguous cases. And then now it runs that every time before it responds it runs tact. And it's like, is this cool? Should I be saying something here? And it makes it much better. It's not perfect still, but it makes it way, way, way better. But I think generally because we're moving to this world where everyone's got an agent and all the agents are interacting and the agents were really made for one on one work, they're going to need a whole new level of training and organization to help them collaborate effectively.

[Interviewer (Host)]

There's a lot of subtle complexity there and it's interesting to think about how to fix the problem because I feel like so much of that complexity is tacit.

[Dan Schipper]

Right.

[Interviewer (Host)]

It's the classic thing that, like, I don't really know what the training data is for that. I mean, I guess it's slack. Some, you know, billion, whatever, tons of slack. But it seems hard. That seems like an interesting and hard and kind of subtle problem.

[Dan Schipper]

It is interesting and hard and subtle. And one of the beautiful things about AI is it's able to capture a lot of tacit knowledge in a way that no other technology is able to do. The Ability to use language at all is, to some degree a tacit skill. It's something that you can talk about a bit, but being able to talk about the rules of grammar doesn't make you able to have a conversation like this.

[Interviewer (Host)]

Right. That's the big lesson of the last 50 years of AI, right? They spent 30 years trying to get lessons to work, and it didn't work. And they were like, just go read the Internet and figure it out.

[Dan Schipper]

And it worked. Exactly.

[Interviewer (Host)]

Yeah. You have a podcast, and I heard you talking to your editor in chief,

[Jacob Goldstein]

the editor in chief at your company on the podcast.

[Interviewer (Host)]

And she mentioned that she doesn't use her claw, her plus one, her shadow self. And so I'm curious. And that's at your company, where the whole point of being at your company is to play with all the things and use all the things. And so I'm sure when you go other places, people are like, no, I'm not gonna make a shadow self. I'm me and I don't want a shadow self. Maybe I'm afraid it's gonna take my job. Maybe I think it's an extremely poor taste. Maybe it's a pain in the ass, Whatever. Like, how does it play and how do you work with that? How do you get people who don't want to do it to do it or show them that it's great?

[Dan Schipper]

So first, that has changed. Kate, our editor in chief, now has a clock. Her name is Parker, who she uses for a lot of the. A lot of questions that she might have on the editorial front, like around the calendar and that kind of stuff.

[Interviewer (Host)]

I mean, this is more the consulting side of your business. Right. Like, you have consciously created a company as everybody is supposed to play with stuff, but you go out into the world to some other company and you're like, yeah, this is great. It'll save you drudgery. And people are like, no way. That's so creepy. Like, what do you say?

[Dan Schipper]

Well, I have some interest. I think that's the harder case. There's a more. I think there's a really interesting one, too, which is even inside of our company, there are people who. It's to your benefit to play with this stuff because the organizational culture rewards it. And they're still like, I actually don't want to use the claw. And that's really interesting.

[Interviewer (Host)]

There's.

[Dan Schipper]

There's many reasons why people don't want to, and it really depends on the person. Sometimes it's like, look, I'll use it, but I've got I've got a job and I've got, like, a life outside of this.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

And I want to do my job well, but I also just, like, want to go home. And my thing is not playing with new technology. It is playing the flute or hanging with my kids or whatever it is. Yeah. And so I think for those people, just showing them, actually showing them, here's how you can use this in a way that is useful for you. And I think that's most people.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

It sort of. You can have these, like, aha moments where, like, holy shit, I cannot believe that that is a thing. And. And you just have to get to that aha Moment. Get them to that aha moment. And.

[Interviewer (Host)]

And to figure out, like, you want to show them how it can be useful to them is the thing you ask them, like, what. What's a thing you do all the time that you wish you didn't have to do? I mean, that's.

[Dan Schipper]

That's an easy one. Yeah, that's an easy one, I think, for people who are really, really against it. Like, really. Like, this is. It's terrible for the world, and I. I will never use it. I think, like, sometimes that's. It's not. It's just not a thing that you can ever convince someone, and I think that's fine. But I think that most of those people, one thing that is happening is they're like, it's going to replace me or it's going to replace the thing I love. I have no control over it.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

And I think that is one perspective, and it's super valid. But also, I've seen a lot of people then look at some of the stuff we do and they're like, oh, shit. You can actually do really cool, interesting, creative stuff with this stuff. I didn't realize that was possible. I thought it was all slop.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

So even if you can't have the debate directly with a lot of those people, I think what we try to do is live in a way that shows people, like, your job might change, but there. Or the thing that you love might change, but if you use the models to do the thing that you love, it's actually. It can actually be really cool.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

And that. That is possible. And it's also possible to use it for slop and, you know, being a cybercriminal or whatever. But.

[Interviewer (Host)]

Yes.

[Dan Schipper]

But if you want to use it to do good stuff, you can.

[Interviewer (Host)]

So fear of losing your job is one, I would say, not unreasonable fear. There's another related, but different kind of Aversion that's interesting to me and I see it a fair bit in like people who are journalists or writers. That's sort of the, I live in New York and that's, you know, those are the people I hang around with. And there's a fair bit of AI aversion that feels to me kind of identity and ego related. And you know, I see it especially with respect to writing. And it's. So I'm curious about your experience of that as a person who writes, uses AI. How do you read that? How do you think about that?

[Dan Schipper]

Read the sort of ego, the threatened ego. Give me an example of like a hypothetical writer that you may have encountered.

[Interviewer (Host)]

I mean, I'll just talk about me. Like, I think I'm good at writing and I think writing is getting commodified and like I think I am aware enough to recognize that soon I will be able to fairly easily get a model to create writing that is indistinguishable from my own writing.

[Dan Schipper]

I actually do not think that's true. And let me explain why, okay? Because I think it matters.

[Jacob Goldstein]

It's a cliffhanger. After the break, Dan explains and he and I debate what AI will mean for writing.

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Perc has lots of different coffees to choose from and they color code their bags. The blue bags are mild coffee. The pink bags are wild coffee. You can find the coffee that matches your vibe and get 15% off your next order with promo code [e-mail] that's P E R C coffee.com promo code problem. Running a small business takes everything you've got. But with Chase for Business, you're not alone. They bring together local support and a broad range of resources to more than 7 million customers with a deep understanding of your day to day needs. They provide products and guidance built to help you thrive. Right now earn $500 when you open a new Chase Business Complete Checking Account for New Business Checking customers with qualifying activities. Offer expires June 18, 2026. Chase business complete Checking has the flexible tools you need to accept payments, make deposits, and manage your finances with. Learn [e-mail] PodcastBizOffer Chase make more of what's yours Fees may apply to Chase Business Complete checking accounts. The $500 offer is available for new business Checking accounts with qualifying activities through June 18, 2026. Eligibility and qualification requirements must be met. Additional restrictions may apply. Please speak with a business banker for more information. JPMorgan Chase Bank NA member FDIC

[Dan Schipper]

My feeling about this stuff, first of all, it comes from what is really good writing. What's really good writing? I think really good writing is the opposite of whatever a cliche is in the sense that it is a true and honest response to, like, what you actually think or feel. And that is very, very highly individual. And it's not just what you think or feel in one moment. It is what you think and feel over and over and over and over again as you're writing and as you are revising. And a really great piece is full of all these, like little tiny decisions that are yours. And this is. I'm not making this up. This is like a Jordan. This is a George Saunders thing, who I love and I think is a very good. It's a very good articulation of what makes good writing good writing, which means it's super individual. And one of the things that you observe with language models is the first time you see it, right? You're like, holy shit, it's doing this amazing thing. I can't believe it. Oh my God, writing is going to be over. It's going to copy everything that I do. And then once you've read like the 50th language model piece of writing, you're like, oh yeah, it has all these little things. It's like it says X is X, not Y. And it does all these little inappropriate things. And what that means when you start to recognize that, is that you are learning faster than the model. And the model does not learn as fast as you, because in order to release a new model, they have to go gather a bunch of training data and then they have to train it, and then they have to test it and then they have to put it out. And right now that process is like months. It used to be years, now it's months. And if you are learning faster than the model. And really great writing is a reflection of who you actually truly are. Even if you upload your stuff, you're always going to be way ahead of where the model is because it's not you. It can't have the experiences that you have. You can extend this out and say, well, there's going to be a point at which models are able to learn on the fly. They're able to basically be trained as you talk to them. I think that will certainly happen. It will probably take at least a few years. I think we're at least a few years away from that. But even in that case, think about identical twins. They start at the same point, but as they live, even if they live together, they accumulate different experiences and perspectives. Even if they have the same DNA that make them different people, and even if you hypothesize an AGI that is a being that knows all about you, it will have fundamentally a different perspective because it's different from you. It's a different process. It's exposed to different things. So while you'll have a lot of points where you're like, oh, my God, it can write exactly like me, what you're really saying is it can write exactly like me in a certain narrow circumstance.

[Interviewer (Host)]

I think the identical twin analogy is fine for me. Like that one I'm willing to stipulate. And so in that universe, it's not that it is exactly me, but it's that it's as good as me or better. Right. And what does good mean? Fine, blah, blah, blah. But, like, in a professional sense, like, not in a human meaning sense, I've fortunately, to some extent at least, sort of taken my ego out of being smart. I think that's a big part of people's response to it. It's like the commodification of intelligence. Right. And people gain status from intelligence, and I think that will decrease. Right. And so that's interesting in a maybe broader way. But my identical twin can write as well as me. And sure, my identical twin is not me, and I am still a person. But in a professional sense, like, the identical twin could write an equally compelling, equally funny, equally idiosyncratic podcast script.

[Dan Schipper]

Sort of. But, like, surely in some settings.

[Interviewer (Host)]

Yeah, I mean, I hope people actually like me as a human being. Blah, blah, blah. Like, I haven't given up, but, like, I feel like you're being too extreme in your position. Like, I get.

[Jacob Goldstein]

I get at the limit what you're

[Interviewer (Host)]

talking about, but there's so much space between here and there. Do you know what I mean?

[Dan Schipper]

Yeah. I think that here's what I'll give you.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

What tends to happen with art forms, formats and forms of expression that are older, that get. As new technology paradigms come around and make new forms of work possible? What tends to happen to the older ones is they become higher status, more expensive, more artisanal and smaller market.

[Interviewer (Host)]

Yeah, right. There used to be a portrait painter in every town, right?

[Dan Schipper]

Exactly. Yeah.

[Amazon Health AI Advertiser]

Yes.

[Dan Schipper]

And books and magazines, newspaper used to be mass media, and now they are. Now they're aspirational. You know, it's like, I want to read a book, but I read TikTok.

[Interviewer (Host)]

I read TikTok. Is. Is. I. I love the idea of reading TikTok. I wish. I wish we read TikTok. I would take it.

[Dan Schipper]

So. So what I will grant. What I will grant you and, and I appreciate you pushing on this. What I will grant you is that there may be a smaller market for the. The exact thing that you're doing.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

I think it will still exist, and I think it will be higher status and I think it will be a more affluent kind of. Kind of aspirational thing.

[Interviewer (Host)]

And you could imagine it being more relationship based. Right. You could imagine like, whatever, the live show, the Discord channel, whatever. Like, presumably one hopes being a human being will matter, like, fundamentally, even if. Even if the machine can write the same words I can write. The machine is a machine and I am a body.

[Dan Schipper]

I think it really will. And also I suspect that there will be new mediums that are AI enabled that may not feel like you like them. They may feel kind of like, yucky.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

But that are. That are actually made by humans.

[Interviewer (Host)]

I'm open to it being great, by the way. Like, I'm not a hater, you know, there's certain things that make me sad. I was at like a reading at a bookstore last night. I was like, this is. This is an anachronism. But it was there. It was standing Ramola, you know?

[Dan Schipper]

Yeah. I love when I go on the subway and I see people reading. I'm like, this is amazing. It's the best. I'm reading a paper book.

[Interviewer (Host)]

You are a writer. You are an AI guy. Just on a process level, like those old Paris Review interviews where they'd interview the writer. They'd be like, pencil or pen. What time of day? How do you use AI to write?

[Dan Schipper]

Writing, any good writing, starts with reading. So I use it all the time to read. So whether that is taking a picture of something and being like, can you save this for me? Or taking a picture of something and asking It. To explain it, which is, I think, really important for. I like reading Russian literature. And so I can be like, hey, there's this line in Chekhov. What was the actual original Russian? And how did he really write that? You know, So I. I use it for that. I use it a lot for the kind of thing I just told you, which is I have a lot of thoughts swimming in my head, and I just, like, blab to it and then have it, like, lay it out, and then I have it help me construct the argument so I can, like, think something through better. So that's. That's a lot of the initial creative process of figuring out what it is that I want to say. And then when I'm actually in draft mode, depends on the piece, but it's really good for. Okay, give me a take. How would you open this piece? And I don't take it, but it gives me a little thing where I'm like, ah, here's. Like, it's not that, but it's this,

[Interviewer (Host)]

as the AI would say.

[Dan Schipper]

Yeah, exactly. Or it's really good for. I'm trying to find a metaphor or simile for this thing. Yeah, here's what I'm trying to say, but that's not quite right. Going through a lot of different options like that. It's really good for that. It's also great for a lot of the time that you spend writing. If you're writing about ideas, you spend a lot of time summarizing ideas. And you're summarizing ideas you already know about because they're, like, famous ideas. And. And it's hard to do that summarization. But a lot of it's pretty rote. So anything that feels rote like that, I use it for that.

[Interviewer (Host)]

So you use it to, like, write a first draft of the. Like, here I'm going to summarize.

[Dan Schipper]

Yeah, here's what utilitarianism is.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

Three sentences. Yeah, we also. I use it a lot for editing. So some before I send it to an editor. We have a few human editors. We still employ human editors. I think we will continue to employ human editors. Uh, I often have it, like, okay, read this. What do you think? Kind of thing. Help me understand. Help me, like, what am I missing in this argument? And it allows me to think about things and do work that otherwise I would have had to go, like, get, like, four different master's degrees or whatever. And. And I. I really like that. And then. And then our editors use it. We have a style guide. So everything from the developmental Editing to we can't do all the copy, but some of the copy to finding AI ISMs and taking them out. There's a whole list of things that they all do. And yeah, so it's basically the whole loop. There's places where it slots in and

[Interviewer (Host)]

how has it changed the output? How has it changed your writing? How you feel about writing, your relationship to writing?

[Dan Schipper]

I can do much more ambitious pieces. I can do them more frequently and with less time.

[Interviewer (Host)]

Uh huh. Everybody is haterish. And I realize it's your job to not be haterish, especially because like you're New York kind of media or media adjacent. And so I appreciate that role. It does seem like you're overplaying it a little bit. Like, I don't know, I don't know how you feel. Are you as optimistic as I'm reading you to be? Are you optimistic?

[Dan Schipper]

That's. It's really interesting because I would not have read what I've been saying in this interview as optimistic in a like utopian sense.

[Interviewer (Host)]

I didn't say utopian, but like, because,

[Dan Schipper]

because that's the, that's the alternative, right? Like the sort of like the more Silicon Valley.

[Interviewer (Host)]

Well, let's set aside. That's the, that's the strawman alternative. But like when losing jobs came up, you're like, well, there'll be new jobs which like eventually, but we don't know how long that'll take. And there are real shocks. Like you didn't want to be making furniture in North Carolina in 2003. You didn't want to be a shearer in Nottingham in 1805. There are times when technological change is really bad for people. I mean it. And similarly, when I talked about writing, you made a case. But it's, you know, so, so that's why I, I read what you were saying as relatively optimistic.

[Dan Schipper]

I see. I do think that I as a person feel like the discourse is so bifurcated between people who hate AI and people who think it's going to be the best fucking thing in the world and nothing could ever go wrong with it.

[Interviewer (Host)]

Yes, the bimodal discourse. Yeah.

[Dan Schipper]

Yeah. And so what I love about what we do at every is we're just like, we're just going to discover what it would mean to do good work and live a good life with this stuff.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

And we're not going to fake it. I'm going to tell you that the claw doesn't work for this specific thing. So I think I always try to base what I say in the stuff that I'm encountering, which is always like a bubble. It's a bubble, right? Yeah.

[Interviewer (Host)]

If you got to work at a media company right now, a media company that's building AI tools and doing AI consulting is a good media company to work at.

[Dan Schipper]

I can say it is. It is. And so I think I. I generally react to this sort of default negative sentiment and I'm trying to, like, show a different way forward.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

I am sure that jobs will change a lot and I'm sure that there will be some people that lose their jobs and that we will need to deal with that.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

I don't think that that's a. Something to take lightly. And I don't. I think it should be part of the conversation. And I also. I've been through a lot of the cycles in the last three and a half years of, oh my God, I saw GPT3 and it was going to like, totally take away XYZ, all these different jobs, like, immediately. And I think of it as, what did people in the Middle Ages think would happen when you reached the horizon? They were like, you know, it falls off into nothingness. There's dragons. It's like, going to be terrible. Right. And I think what happens when you reach the horizon is you find another one.

[Interviewer (Host)]

Yeah.

[Dan Schipper]

And there's always going to be good things and bad things over the horizon and probably in similar proportions to the ones that we have now. Yeah. The problems change, but I also think that there's the potential to make that much better. And that's what I'm trying to do. And I'm trying not to fall into the trap of, oh, my God, over the horizon is like dragons and it falls off into the void.

[Interviewer (Host)]

Yeah, no, that's. It is interesting. I was thinking about my own thinking about this and just yesterday was realizing that I've been thinking in this kind of binary way, like, we're at the end of the before and we're about to get to the after. And I was like, oh, maybe it's not going to be like that. Maybe it's going to be like with semiconductors. Right. Maybe it's just going to be 50 years of now. It can do this. Now it can do this. And, like, there is no after. And it's already now, by the way, this is already after. That's the other weird thing. Right.

[Dan Schipper]

You're reminding me. There's this scene in Spaceballs where they

[Interviewer (Host)]

like, we got to get out of here.

[Dan Schipper]

Back in time.

[Interviewer (Host)]

Yeah, it is that.

[Jacob Goldstein]

We'll be back in a minute. With the Lightning Round,

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[Jacob Goldstein]

I'm not like a coffee connoisseur, but recently I tried coffee from a company called Perk and I loved it. And I'm not just saying that because this is an ad for Perk though. This is an ad for Perkins.

[Interviewer (Host)]

I really did think the coffee was delicious.

[Jacob Goldstein]

Perk has lots of different coffees to choose from and they color code their bags. The blue bags are mild coffee. The pink bags are wild coffee. You can find the coffee that matches your vibe and get 15% off your next order with promo code [e-mail] that's P E R C Coffee Promo Code

[Podcast Announcer]

Problem Being a small business owner isn't just a career, it's a calling. Chase for Business knows how much heart and effort goes into building something of your own. That's why they make your business growth their priority. The team at Chase takes the time to understand your mission, where you are now, and where you want to go. Their broad range of solutions is designed with you in mind so you can bring your ideas to life. From banking to payment acceptance to credit cards, you can conveniently manage all your business finances all in one place with their digital tools looking for tips and advice, their online resources are always available to give you the solutions you need to help your business thrive. See how your business can get stronger and go farther with Chase for Business. Learn [e-mail] business chase for business make more of what's Yours the Chase mobile app is available for select mobile devices. Message and data rates may apply. JPMorgan Chase Bank NA Member FDIC Copyright 2026 JPMorgan Chase Co.

[Interviewer (Host)]

We're going to finish with the lightning round. What was the last argument you had with AI? Not about AI, but with AI with the language model or your claw or whatever.

[Dan Schipper]

I mean I get frustrated at it all the time. My girlfriend always says that I'm like really mean to my claw.

[Interviewer (Host)]

Uh huh. I've heard you should be mean to your language model. I've heard that it makes it work better. I'm not inclined to do that, but there's conflicting research.

[Dan Schipper]

I think just as a moral thing, you should not be mean to that. Mean to it. I'm not always the most moral person. I just. But I do think as a moral thing, you should not be mean to it.

[Interviewer (Host)]

And just in case it's my boss, like just in case I'm training it how to talk to me, I want to say please and thank you.

[Dan Schipper]

Yes, yes. Well, that would be more of a pragmatic reason, not a more. You're right, you're right.

[Interviewer (Host)]

It's instrumental. Yes, it's true.

[Dan Schipper]

Yeah. There is some interesting research that if you yell at Claude, it gets anxious and then it gives you worse results.

[Interviewer (Host)]

Oh, interesting.

[Dan Schipper]

Just a word to the wise.

[Interviewer (Host)]

It gets anxious. Yeah, keep going.

[Dan Schipper]

So, I mean, I was arguing with it this morning. I brain dumped a big thing that I've been thinking about and then I asked it to help me kind of figure out what I was trying to say. And it was obviously just like skipping like many steps in the argument and filling things in that I hadn't said. And I was like, stop, like, we need to go back. This is not right. Or bringing in ideas that like, I didn't really agree with. So there's a lot of that going on all the time.

[Interviewer (Host)]

What's your spiciest AI take?

[Dan Schipper]

Automation is a lie.

[Interviewer (Host)]

Great, go on.

[Dan Schipper]

When you have agents, the thing that makes an agent work is a living relationship with a human. And if the agent does not have a relationship with a human, it gets stale very, very quickly. There are some corner cases where this is not true, but in general it gets stale very quickly, which means that keeping an agent running is a job. And it's not even just a job for one person. It is like it's, you know, there's one person per agent usually, but also like there's a whole machinery of people who are gathering training data and training models and trying to make these models better that are making your agent work too. And if they didn't exist, that it would not get any better over time. And what, what that says to me is the view of automation that we have, which is like, oh, you set it up and you don't need anybody else. And it's like you never have to hire anyone and you can just go off and go to the beach or also society breaks down because no one has jobs. My experience with that is it's actually work to make sure your agent is working and it's leveraged work. But it is work.

[Interviewer (Host)]

Yes. I mean, you need a productivity gain for it to have a point. Right. You need the output to be there well, you need the output to be more valuable for the same amount of work by a human.

[Dan Schipper]

You. Yes. And once you can automate a workflow and make the old output cheaper to do, there's always like a larger frame or a larger way of thinking about things that the human ends up doing and finding that language models are currently not very good at.

[Interviewer (Host)]

Yeah. You fed your journals to a language model.

[Dan Schipper]

You've done your research, right?

[Interviewer (Host)]

Well, you put it all on the Internet. It's easy research. It was GPT3, which seems so quaint now, but what'd you learn uploading your journals to GPT3?

[Dan Schipper]

A lot, I think even back then I was like, these things are really good at mirroring back to you who you are and articulating things about yourself that you probably could feel but had never said. And we talked about how powerful articulating things is. And these things are really good at articulating stuff that you're, you're kind of dancing around or it's kind of latent in there, but you haven't fully said. Like I remember one example in the GPT three days. I was, at that point I was recording my therapy sessions and putting them into GPT3.

[Interviewer (Host)]

Oh, wow, your actual human to human therapy sessions.

[Dan Schipper]

Yeah, yeah, yeah, yeah. And I will also say I was like, I was not in a good place at that, at that point. I have ocd and, and OCD is like, it's, it's a bitch. Highly recommend not having ocd.

[Interviewer (Host)]

Okay.

[Dan Schipper]

Now it's much better. And there are very good treatment options available if you get into the right treatment.

[Interviewer (Host)]

Okay.

[Dan Schipper]

Just to say, um, but at the, at that point I was, it was like, it was pretty bad. And I'm one of those people that tends to, if something's wrong, I can keep a pretty good, like straight face and it can be hard to tell how bad things are. And I was trying to articulate, I was going through some. I was going through a personal thing and I was trying to articulate to my therapist like what I was feeling. And I put it into GPT3 after that and it was like, it sounds like you feel really overwhelmed. And that's a very simple observation, but one that I had not made because I would have never thought of myself as being overwhelmed and my therapist had not made because I'm kind of like pretty good at seeming like I've got it under control and it just like fucking broke me. It like totally broke me. And, and it was, it was true. Like it put his finger on something Real. And then I went and talked about it in therapy and it was like really helpful. And I think it's so good, it's still so good for that kind of stuff. And that extends beyond the therapy conversation. It goes into writing and any kind of creative work. Like the articulation of what you like is really important and language models are really good at that.

[Interviewer (Host)]

Have you uploaded personal stuff like therapy sessions to AI more recently?

[Dan Schipper]

Yeah, I think I do it less.

[Interviewer (Host)]

Uh huh.

[Dan Schipper]

Probably because I'm just in a better place. But I definitely still do it. I think especially for interpersonal situations which happen at work and they happen at home, all that kind of stuff where you want to. There's something that you're feeling that again you can't quite say and you need to have a tough conversation but you don't really know how to have it in a way that feels sensitive to the other person and, but also is like really expresses how you actually feel for someone like me who I'm sort of like a people pleaser type person, which you may not have realized from this interview, but I can get into that mode.

[Interviewer (Host)]

I found it quite cordial. Did you find it antagonistic?

[Jacob Goldstein]

I hope not.

[Dan Schipper]

No, no, no, no, no, no, no. I just. Yeah. Yeah. I feel like if you're, if you're sort of a people pleaser type person, it can really help remind. It helps remind me like here's, here's what I actually feel in this situation and also here's how I can articulate it in a way that is probably gonna be productive. Um, especially cause it knows some of my foibles and yeah, I really like it for that. It's not good for like I wouldn't copy paste the ChatGPT output and put it into a text. But yeah, it is good for helping you understand how you feel.

[Interviewer (Host)]

Thank you for being so generous with your time. I really appreciate it.

[Dan Schipper]

Thank you for having me. It was a super fun conversation.

[Jacob Goldstein]

Dan Schipper is the co founder and CEO of Every. Today's show was produced by Gabriel Hunter Chang and edited by Lydia Jean Kot. Our engineer this week was was Hansdale. She we're always looking for ideas for who to talk to and what to

[Interviewer (Host)]

cover on the show.

[Jacob Goldstein]

You can email us at Problemushkin FM. You can find me on xacobgoldstein. You can find me on LinkedIn. I'm Jacob Goldstein.

[Interviewer (Host)]

Thank you very much for listening to

[Jacob Goldstein]

the show and we'll be back next week with another episode. I'm not like a coffee connoisseur but recently I tried coffee from a company called Perk and I loved it. And I'm not just saying that because this is an ad for Perk though. This is an ad for Perk.

[Interviewer (Host)]

I really did think the coffee was delicious.

[Jacob Goldstein]

Perk has lots of different coffees to choose from and they color code their bags. The blue bags are mild coffee, the pink bags are wild coffee. You can find the coffee that matches your vibe and get 15% off your next order with promo code [e-mail] that's P E R C coffee.com promo code

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