Embracing Twilight Zones, Self-Exploration & Living with OCD with Dan Shipper

Jonny Miller (00:45.55)
All right, fine. Well, fuck it. Let's just dive in. Welcome to the Curious Humans podcast, Dan.

Dan Shipper (00:48.929)
Let's do it live.

Dan Shipper (00:54.123)
Thank you, I'm excited to be here.

Jonny Miller (00:56.424)
In three words, how are you feeling in this exact moment?

Dan Shipper (01:04.096)
Excited, a little anxious actually now that you mention it. And probably like a little tired. I'm having a very relaxed kind of like, dare I say downshifted kind of day. And so I think some of my like, I'm just feeling sleepy because of that.

Jonny Miller (01:27.372)
Hmm. But also there's like a sense of anxiousness there as well. What do you think that might be?

Dan Shipper (01:31.189)
Yeah, well, we're recording a podcast and you know, ever, you know, when you start a podcast, you kind of like get that little bolt burst of adrenaline or something, you know, so I probably I'm feeling that.

Jonny Miller (01:39.758)
Yeah, nice. It's true, me too. I've done hundreds at this point and I still feel the sense of like, it's like I've just taken a double shot of espresso or something. wow. Even though really looking forward to it, there's still this activation energy.

Dan Shipper (01:52.385)
you

Dan Shipper (01:56.033)
Yeah, natural. It's not natural Red Bull. You know, you don't need coffee. If you're a podcaster, you just just hit record.

Jonny Miller (02:02.702)
Great, well the question that I like to begin these conversations with is, Dan, do you think that you were an exceptionally curious child and if so could you remember a story about something you were curious about?

Dan Shipper (02:20.831)
Yes, mean lots of things. I loved the Titanic when I was growing up. Really like in elementary school, like kindergarten, first grade. And I was just like obsessed with it. And I actually remember I was so obsessed with it that I had this like big Titanic book and like, don't, this is kindergarten, like in first grade-ish. So like, don't know. These memories might be a little jumbled up.

I could read to some degree, but I probably wasn't like a great reader. But I remember like having this gigantic Titanic book and then being so obsessed with it that I wanted to, I wanted to retype it. think it was like from either as a, my birthday or for my mom's birthday or for some, for some reason I wanted to like create my own version of this book. And so I was just, my mom had a typewriter and I would just like sat with a typewriter, and was like retyping the book by hand because.

Jonny Miller (03:14.709)
Whoa.

Were you retyping the exact words in the same way that like I've heard writer advice of like, retype the words of Ernest Hemingway so that you can feel what it's like to be a good writer? Like that kind of thing? That's what it was?

Dan Shipper (03:24.287)
Yeah, I think I think I was. It was not to be a good writer. It was just because like I was just extremely obsessed with this for some weird reason. But I was not editing. I was just I don't even know if I could read it at that point. I was just just really, just really liked it. And then I remember we went on a on like a Caribbean cruise after that. And I was like terrified that we were going to hit an iceberg and die.

Jonny Miller (03:33.996)
Interesting. And you, you were, were you editing the words or was it just like, you just wanted to retight?

You

Jonny Miller (03:53.889)
In the Caribbean.

Dan Shipper (03:55.015)
Yeah. So smart, but so dumb is probably the summary of how I was what I was like as a child.

Jonny Miller (04:06.367)
Amazing. besides the Titanic, were there any other books or stories or like myths that you resonated with?

Dan Shipper (04:13.525)
Yeah. yeah. I mean, how much time do you have? I love, love, loved Stephen Hawking. And he like he had a couple of books about like the Big Bang and the universe. know, I absolutely was so into him and like really wanted to like study at Cambridge because he was there.

Jonny Miller (04:18.254)
90 minutes or so.

Jonny Miller (04:40.302)
you

Dan Shipper (04:41.161)
And then I was really into Bill Gates. That's how I started learning to code. I read a Bill Gates biography and I was like, whoa, amazing. And then Star Wars, huge, huge Star Wars fan. Love lightsabers and Jedis and all that kind of stuff as a short list of other curiosities.

Jonny Miller (04:46.798)
Hmm.

Hmm.

Jonny Miller (04:55.906)
Hmm.

Jonny Miller (05:02.958)
Nice. My high school maths teacher was actually Stephen Hawking's maths teacher and he always used to share anecdotes about how Stephen was like, he would rank us in our maths class of like, where we sat was like how smart we were at maths. And he was like, Stephen Hawking was always number three. And I remember I was like, between like three and four, I was like, secretly like, that makes, you know, increases the odds of me being this like genius when I'm older.

Dan Shipper (05:07.67)
No way.

Dan Shipper (05:26.773)
That's really cool. love that. Yeah, I was always terrible at math. I was just never going to have I was out of it last. So it's never gonna happen for me. But

Jonny Miller (05:39.377)
Fun. I'd love to give listeners some context as to like who Dan is. What was your arc from say reading Star Wars and the Titanic to founding every this media company? Like what was some of like the the inflection points?

Dan Shipper (06:03.225)
yeah, Bill Gates biography in fifth grade wanted to start a Microsoft competitor. I was going to name it Megasoft. and I wanted to build an operating system to compete with windows. And so I, I begged like my dad to buy me a programming book, which he did. And he was like, I'll buy this for you. If, fifth grade, I think that's like 12 or something or ish. Yeah.

Jonny Miller (06:21.016)
Wow. How old were you this time? What age were you? Wow. Yeah, ambitious. I love it.

Dan Shipper (06:30.689)
And he bought me the book and back then that's how only way you can learn how to code like you had to buy like a $40 book. It was it wasn't you couldn't just watch YouTube videos or whatever. And then.

I definitely found that I was not going to be building an operating system by myself, but I really liked coding because it's like the only way that I could make things that I could turn into like a business or turn into products because I was like 12. And I had, had some other like things that were more physical things that I was building, but those were like a lot harder to do. And I.

But I just, I just kept coding basically. and when I was in high school, I got really into apps. So I started building apps for Blackberry. this is before the iPhone came out. and I, built this thing. I kept losing my Blackberry in my house, but it would be on silent. So I couldn't find it. and I made this thing called find it that, you could basically make your Blackberry ring, even if it was on silent. and kind of iterated that into like, it had a web interface and you could track your Blackberry and lock it and.

make it call you and do all this stuff. This is before I my iPhone came out. And then the iPhone came out, so I started building iPhone apps and that was really fun. And basically that's how I paid for gas and food in high school. And then in college, I started doing a lot of startup stuff. I studied philosophy. So I was doing philosophy and then I was like just building lots of apps and stuff on the side with friends. College was amazing because it was like the first time.

I was around people that like also wanted to make stuff. I, when I was in high school, I was like, very, very far ahead of anyone else in terms of like just being into programming. No one else in my high school was into it. So I would like, just like sit with the computer science teacher and he, he would just like do something else. And I would have like a 45 minute or hour period to just like do my own project programming projects. Cause I was like way far ahead of him at the time. and,

Dan Shipper (08:40.705)
So in college was doing lots of startup stuff and I started this company called Firefly and that was like summer after sophomore year of college and Firefly we did co browsing and co browsing is kind of like screen sharing but instead of sharing a desktop you share what's on a web page and we applied it to customer service so if a customer is having a problem with the website and they call into support or they're chatting with an agent we let the agent see what they're doing on the website help them through the site in real time

and it all works without any downloads or installations. It's all JavaScript based. It was pretty cool. And that was in like 20, we started in 2012 ish and ran that for a few years. And then as I was coming out of college, I sold it to Pega, which is this big public enterprise software company. And I ran the business inside of Pega for a couple of years. So that was like a really big moment for me.

and the like sort of, guess, fulfillment of like a lot of things I had dreamed of for a really long time. Ran the business inside of Pega for a couple of years. Really at that point, like right after I sold it was when I first started to like, like I was always a pretty, I don't know if chill is the right word, but like I always just like could handle everything kind of person. And then right after that, I started having panic attacks for the first time and that started like just created this whole like.

Jonny Miller (10:04.023)
Mm-hmm.

Dan Shipper (10:06.049)
parallel mental health journey that I've been on for the last like, I guess, 10 years now, which I'm happy to talk about at some point. Yeah, I took a couple years off from there and like was basically just fun employed. I traveled and I like, I wrote a novel or wrote some drafts of a novel. I worked at an incubator, you know, did some venture investing like angel investing. And in 20...

19, 2020, I just got, I was like, okay, I think I'm gonna start another company. I wanna do that. And started what became Every, I'm happy to go into that story, but that's the overall arc of, or at least the arc from one perspective of my life so far.

Jonny Miller (10:55.382)
Yeah, wow, beautiful. A couple of things I'm curious about that. is, so I studied philosophy as well at college, university, and it was probably the one thing that I enjoyed studying in like my entire schooling career. And I'm curious, like, what was it about philosophy that you enjoyed? And do you feel like your philosophy background has actually been supportive in the work that you're now up to?

Dan Shipper (11:21.141)
I mean, definitely, because like my whole, like a lot of my job is like writing about philosophy stuff. So, I mean, maybe it's like on the surface by AI and like, whatever, but like a lot of it is just me kind of talking about philosophy in a, in a way that's hopefully more understandable than a lot of philosophy is. why did I do it? I mean, I basically got to college and I was like, the thing I want is to just read a lot, like be really well read by the time I leave.

Jonny Miller (11:37.709)
Mm-hmm.

Dan Shipper (11:50.585)
and I'll also just, there's something for me about just like,

figuring out like what it means to live well. And I was like, cool, I think philosophy is like the way to do that. And it turns out like, especially academic philosophy is like not actually that. But you do learn to think and which is one part of living well. And I think you also learn how easy it is to kind of like get suckered into like a particular like, like narrow way of thinking because like you go in

Jonny Miller (12:02.282)
Mm-hmm.

Mm.

Jonny Miller (12:09.974)
Yep. Yep. Totally.

Jonny Miller (12:17.517)
Yeah.

Jonny Miller (12:28.75)
Mm-hmm.

Dan Shipper (12:28.861)
on like the first day and they're like, okay, like Plato thought this and you're like, cool. Yeah, that's definitely how the world works. It's like all forms and like whatever. And then they're like, Aristotle next week, like totally not that. And you're like, wow, like Plato sucks, you know? And you're like, Aristotle's amazing, holy shit. And then you can just go through the history of philosophy and it's just like every generation and someone being like, this is what it is. And then someone else, and you're like, wow. And then the next week it's like, this is totally different. And you're like, okay, I guess I'm not gonna get, hopefully not gonna get.

Jonny Miller (12:37.101)
Yep.

Dan Shipper (12:58.465)
totally suckered anymore that there's like one system that is like totally the answer and just be a little bit more. I don't know if skeptical is the right word, but like hold things a little bit more loosely and then be able to play with ideas and all that kind of stuff. I love that. And for whatever reason, I don't know why, but

at the end of the law of a long day or at the beginning of a long day, just like sort of sitting down and reading something incredibly abstract and difficult to read is like very relaxing for me. And, and I, I just, I have a very like restless intellectual appetite, and I just love just exploring far and wide. And so I think philosophy is like the

the like core of something that just like goes into like lots of different fields like psychology and neuroscience and physics and like whatever all that kind of stuff just like or literature art whatever all that stuff I just I love it so I can't even remember the question you asked me at this point so I'm gonna just end my answer there

Jonny Miller (13:54.317)
Mm.

Jonny Miller (13:58.775)
Yeah, yeah,

Jonny Miller (14:09.22)
It's great. think this is going to happen. feel like this conversation is going to bounce around a ton of very random topics. But I love what you said there about like the question, like, what does it mean to live well? Because I think that that is part of the reason why.

Dan Shipper (14:14.912)
Hehehehe

Jonny Miller (14:22.282)
I love your writing so much and I feel this sense of like, like, like intellectual kinship around like wrestling with this question in many, different ways. And I think a lot of your writing around AI is for me, it's, the thrust of it is like, how can this help us live well or help us answer questions that help support that? and one, another jumping off point I want to just like,

I'm curious about as well is one of your recent posts was around the title was admitting what is obvious and it's basically about like your decision to commit to being a writer even potentially at the expense of like leaving money or productivity on the table like at least very like doing things differently. What like what led to that realization for you and

Maybe more importantly, how has it felt since you made that definitive shift about roughly a year ago?

Dan Shipper (15:16.287)
Yeah. I've always loved writing and I've always loved building things. I think, and writing was a part of my last company too. And, but I think for me, for a long time, like being a founder was like an easier thing to like hang my shingle on, you know? It was like the community of people that I resonated with and like, it's socially rewarded and like, there's a lot of like stuff.

Jonny Miller (15:41.837)
Mm-hmm.

Dan Shipper (15:46.337)
with being a founder. I mean, I did like after my last company, I spent some time like writing a novel and

Jonny Miller (15:48.27)
Mm-hmm.

Dan Shipper (15:56.511)
I didn't say I'm a writer, but I did say I'm writing a novel and it's interesting. It's interesting, like feeling the judgment that you often get from people being like, why are you doing that? Like you could be doing so much, so many other interesting things. I'm just, and so that, like I've had that a lot. and so that, that's kind of interesting. And I do think like, yeah, giving up the sort of founder identity and also not really feeling like there is a model of being a writer that exactly fit.

Jonny Miller (16:08.628)
Interesting.

Dan Shipper (16:25.661)
what I wanted to do and, and, and could, you know, help me pay the bills, you know, all that stuff was like, it's just felt hard to be like, yeah, I'm just going to be a writer. and so when I started every, I think in a lot of ways that was me, being like setting up a way for me to like be a writer, but still call myself a founder.

Jonny Miller (16:28.238)
Mm-hmm.

Jonny Miller (16:38.094)
Mm-hmm.

Dan Shipper (16:54.273)
because it's a media company and like we raised a little bit of money for it and like we had we had this like wrapping we had a like a lot of the trappings of trying to potentially be a technology business and We oddly like also have become one even more so after I made the decision to be a writer so there's a lot of interesting things there, but Basically like the first

Jonny Miller (16:56.781)
Mm-hmm.

Jonny Miller (17:13.516)
You

Dan Shipper (17:17.885)
era of every, the first year or so, like I was writing all the time and I loved it. We were growing super fast. And then we raised a little bit of money and me and my co-founder, Nathan, think decided like, you know, maybe, not maybe, we want to make this a real business. And so that means we have to run the business. can't write anymore. And so we both stopped writing and, I w I became more miserable and the business stopped growing. which sucked. and then we had this.

Jonny Miller (17:43.69)
You

Dan Shipper (17:47.073)
kind of big, you know, sort of decision point at some point where the business was doing fine. I had started writing a little bit again, Nathan had started writing a lot. And this is like several years in and he started building on the side a basically like a new word processor. Could we did a lot of writing internally and like we had a lot of opinions about like what would a new word processor should be like.

and so we launched it and it just like, it's called Lex and as in like one of the first real like AI powered word processors back when like chat GBT was just coming out and GBT three was just a thing and it just went super viral. and we ended up deciding to spin it out. So he now runs that company. and for me, that was like a real point of just like, okay, like, what am I doing here? what do I want? Like it's, it's.

almost a blank slate and I get to like reflect on like all of the things that like I've done over the last couple years and just like decide like what am I even doing this for, you know? And that was like a hard, it was a hard like moment, it was a sort of like a little bit existential, was like, you and I think I just...

Jonny Miller (18:56.652)
Mm-hmm.

Dan Shipper (19:13.949)
When I introspected on it, when I thought about it, that was like writing is just like the thing that is the thing for me for whatever reason. It's like, just feel this, deep connection to that act. And I feel like I have something to say and something that I want to like bring to the world and like, and what's really funny is I started to say that to myself, like, maybe I just, I think I just want to write like, fuck it. Like, I'm just going to write. And what I did was.

Jonny Miller (19:27.534)
Mm-hmm.

Dan Shipper (19:44.453)
as this was like happening, I just asked Chachi Buti, was like, Hey, are there any like writers who, have done kind of what I want to do? Cause I want to write, but like, don't want to like not do business, you know, I want to like do both, but I, but the core should be writing. Like I don't want it to be like this thing where I'm a founder and like, I have this cute side thing where I write, I want to be a writer and have businesses around my writing. And Chachi Buti was like, yeah, a lot of people have done that.

here, like, have you heard of Sam Harris? And I was like, yeah, of course Sam Harris does this. he's got the, you know, he writes books, he has a podcast, he's got a newsletter, he has the waking up app, which is doing quite well as far as I know. another one is, Bill Simmons, who, ran Grantland and the ringer, and sold it to Spotify for a couple hundred million bucks and was like the main podcaster at the ringer. and there, there are a lot of other, there are a lot of other examples actually, like when you actually start looking.

Jonny Miller (20:24.902)
Mm-hmm.

Dan Shipper (20:42.241)
It's quite a, it's not, wouldn't say common, but especially in the internet era, it's much more common. And especially now, I think a lot of people in our world are like sort of waking up to how this can work. Cause you know, media is really hard and it's really hard to monetize. And so if you can build businesses around the audience and attention and whatever that are not just content, it's like, it can be actually pretty powerful. So.

Jonny Miller (20:51.812)
Mm-hmm.

Mm-hmm.

Dan Shipper (21:07.701)
Then once I had a model, it's like, you know that thing with the four minute mile where it's like once one person runs a four minute mile, everyone does it? Once you know it's possible, you just do it. Once I knew it was possible, I was like, I'll just do that. so, because the core thing that makes it really hard to do is writing takes a lot of time and emotional space.

Jonny Miller (21:14.178)
Yeah, uh-huh, uh-huh. Yeah. Interesting.

Dan Shipper (21:33.345)
And businesses take a lot of time and emotional space and usually one or the other wins. And usually the business stuff wins because it's like on fire, you know, you have to like fix stuff all the time. Yeah, exactly. To you, to yourself, to everyone else. Like it's, hard to be like, yeah, this thing's broken in the, in the company. Like people are yelling at each other. Like, well, I have to write.

Jonny Miller (21:38.469)
Mm-hmm.

Jonny Miller (21:44.592)
Yeah, it's like easier to justify as well.

Dan Shipper (22:00.437)
But once I made that decision, the model that a lot of people follow that do this, there's a pretty clear model. you do, there's a couple different configurations, but the one that I decided to do is you hire a couple people, you bring a couple of people into the organization who are senior leaders who get what you're trying to do, understand the vision and also understand how to like...

operate and how to, you know, run things. And you let those people like run a lot of the day to day and have a lot of autonomy to like make decisions and all that kind of stuff. And obviously, you're like, you're around, you're there. But like, their job, to some degree is to like, keep your schedule clear, like more clear, so that you can do the creative work that makes the whole thing run.

Jonny Miller (22:53.964)
Mm-hmm. Mm-hmm.

Dan Shipper (22:57.481)
And so I brought on Kate who's our editor in chief and she runs the media side and she does a fantastic job. And about six to nine months ago, Brandon Gale joined who's who runs our studio and a couple other things for us. And both of those, both of those people have been like really fantastic. And there's just a whole team of people that are doing amazing stuff for us. And, and

Jonny Miller (23:22.406)
you

Mm-hmm.

Dan Shipper (23:28.057)
It has actually worked quite a bit better than I thought. still like, you know, I'm, I still am busy, but, but I've managed to write every week. And that is like really cool. And I've, know, I have like a long form piece that I'm working on that like, I'm hoping will come out in the next like couple of months that like requires a lot of like time and thought and whatever. so for whatever reason we've been able to like,

Jonny Miller (23:35.716)
Mm-hmm. Mm-hmm.

Dan Shipper (23:58.331)
managed to keep overall every stuff like the output really high quality and also just like ship a lot of stuff. And it's been it's so fun. It's such a fun crew of people. I feel very lucky to get to do it.

Jonny Miller (24:10.394)
Hmm. Hmm.

Jonny Miller (24:15.814)
That's amazing. It seems from the outside, at least, that you guys are having a lot of fun and it feels like that maybe like amount of fun founder is having is a pretty like good metric for like how well the business is doing as well. At least I would imagine. There's a couple of directions that I'd love to go in. One is like a deep dive into the kind of AI rabbit hole. I have just like so many questions for you about that that I want to get into.

Dan Shipper (24:41.249)
.

Jonny Miller (24:43.908)
But before we go there, want to kind of touch on, you mentioned like that the mental health journey has been like a parallel journey since you sold the first company. What was it? Do you think that that like selling the company created a kind of like existential?

Dan Shipper (24:52.199)
Mm-hmm. Yeah.

Jonny Miller (25:02.678)
space for these things to arise. like, I'm curious like what you think the connection was there and also what have you, yeah, I guess what have you learned about yourself and what has that journey been like to the degree that you're open to sharing?

Dan Shipper (25:15.647)
wow. I think we do a whole podcast on that. So we may have to do, we may have to do a AI round two or something, but I'll give you, I'll give you the, the, the cliff notes. And if you want to go deep over, can. Yeah. I mean, it's hard for me to say why, why that was the time when it all kind of like started to come out. think for sure, like selling a company is a serious discontinuity in your life.

Jonny Miller (25:28.186)
Good. OK.

Dan Shipper (25:43.817)
You have a set of goals and a set of people you're around and like an identity. And at that point I was in college and you go from that to like you're out of college, you're away from all the people that you kind of know and are comfortable with and you've lost your identity and you're also like you've sold a company. So you're kind of in this.

Jonny Miller (26:03.494)
Mm-hmm.

Dan Shipper (26:08.959)
financially and psychologically, like you're in a very different place from other people. So it's, it's amazing. Like don't I glad I did that, but also it's, can be lonely, which is I think a classic thing. So, and so for, for a lot of reasons, it is like actually quite stressful, once you're done, but in a different way. Cause I think, when you're running a company, the stress, it's like performance anxiety. And so you.

Jonny Miller (26:17.03)
Mm-hmm.

Jonny Miller (26:20.517)
Mm-hmm.

Jonny Miller (26:28.645)
Mm-hmm.

Dan Shipper (26:37.299)
you lose the performance anxiety because the performance is over, but then you just have existential dread. Basically, you're like, what am I even going to do today? And who am I? And yeah, it just like sort of, I started to just feel really like at Pega, just, I started to get like really worried about like, is this product even any good that they paid for and like,

Jonny Miller (26:41.988)
Hehehehehe

Dan Shipper (27:01.675)
What if it doesn't work and like, what if the business isn't good? And like, did I fool people like that kind of thing? You know, in like a very persistent way that like looking back, I, I know how like, sort of almost pathological that was. but at the time, like I didn't even have, I, was just like simmering in me and I didn't even talk to anyone about it. Cause I was just very used to kind of like going forward or whatever. anyway, so I started having panic attacks a lot, which really sucks.

Jonny Miller (27:06.946)
Mm-hmm.

Jonny Miller (27:25.484)
Mm-hmm. Mm-hmm.

Dan Shipper (27:31.519)
You know, do not recommend. and so I started going to therapy and, I was also at that time in a long-term relationship that like ended in 2016. So it was like a five-year relationship that ended. So that's another big like discontinuity where you're like, my God, wow. so companies over relationships over having panic attacks, feeling really anxious. and, and then I spent like four years being like, what do want to do with my life?

Jonny Miller (27:33.734)
Mm-hmm.

Jonny Miller (27:58.438)
Hmm.

Dan Shipper (28:00.201)
So that was a lot and I was in therapy and talk therapy and I felt like I was like learning some stuff, but it felt like the kind of thing where.

I knew some things intellectually and then it just like wasn't translating into like my emotions, you know, there's, there's like a golf there that like, you, kept like trying to bridge in different ways and I've just became such a huge nerd. Like I've read every therapy book, maybe not everyone, but like a lot, a lot, a lot, lot of therapy books. and of course I like went down the mindfulness path, which honestly has been helpful and is a really big part of my life still, but like, with the things I had to deal with, like,

Jonny Miller (28:16.812)
Mm-hmm. Yep, totally.

Jonny Miller (28:28.122)
Mm-hmm. Mm-hmm.

Dan Shipper (28:41.343)
I want to yeah, I went on like a 10 day Vipassana retreat and I did like I sat Zen for a long time and like I did all this stuff and it's like you're it's very hard to actually treat clinical grade problems with with meditation, unless you know what you're doing. If you know what you're doing, it can actually be quite helpful. But if not, it can make things worse. And so

Jonny Miller (28:55.215)
Mm-hmm.

Jonny Miller (29:03.344)
Totally, especially Vipassana. mean, that's like surgery for the mind in some ways. It can go both ways.

Dan Shipper (29:09.451)
my god, yeah, it's crazy. mean, it's funny, I've had some of my worst experiences in Zen retreats, Vipassana, like worst physically, definitely the worst physically I've ever felt because they like, you don't move for like three hours a day or what, it's like, it's fucking crazy. It's like 11 hours of sitting and you don't have a chair. It's, it's really nuts. But at the end, I felt like the Buddha, I was like, holy shit, I have laser beams coming out of my eyes.

Jonny Miller (29:18.598)
Mm-hmm.

Jonny Miller (29:28.26)
Yep.

Jonny Miller (29:32.01)
You

Dan Shipper (29:33.825)
Zen was more actually kind of some terrifying shit. anyway, eventually what happened is, and this is after three or four different therapists, I realized I had OCD, which is very common to not know that you have OCD and have it be misdiagnosed for a long time because it often presents as anxiety.

Jonny Miller (29:37.413)
you

Jonny Miller (29:41.729)
huh.

Jonny Miller (30:01.583)
Mm-hmm.

Dan Shipper (30:03.457)
And I just diagnosed myself. then once I realized that that's what I had, my dad was like, I have OCD. I was like, are you fucking kidding me? No. And so, so with the, the weird thing about OCD is, regular talk therapy actually makes it worse. and you, what you have to do first before you can do talk therapy is,

Jonny Miller (30:11.392)
He had a hoodie? Wow. Wild. Wild.

Jonny Miller (30:25.893)
Hmm.

Dan Shipper (30:31.809)
Exposure and response prevention. So and this now we're getting down the rabbit hole so you can you can pull me up if at any time if you want but basically in OCD you have obsessions and compulsions. So obsessions are like intrusive thoughts images emotions that kind of thing that like pop up all the time. So like a classic one is people have like contamination OCD and they're just like really worried that their like hands are dirty or have bacteria on them. And so that's the obsession. It's just like you get this like

Jonny Miller (30:57.535)
Mm-hmm. Mm-hmm.

Dan Shipper (31:00.689)
overwhelming sense of like dread that's like it's a thought but it's also like a big emotion and you're and you're dread and uncertainty and fear. You're like my god my hands are dirty. I don't this is not mine I have other stuff it's it comes in like themes but like this is an easy one to relate to I think. So you get that fear and then you go and wash your hands and that's the compulsion because the hand hand washing

makes it feel better for like five minutes and then it just like comes right back and you're like, my God, my hands are dirty. And then you're just like washing your hands like 50 times a day and your hands are raw and red. And like, you're like, I have a problem. Something's wrong. and, and for me, so OCD can be outward. so you have outward compulsions, but often it's inward. So all the stuff, like I just, for example, for me, like a compulsion is ruminating. I just like think about it all the time. and then you're just spending like hours a day thinking about whatever it is.

Jonny Miller (31:35.672)
Hmm

Jonny Miller (31:52.848)
Mm-hmm.

Dan Shipper (31:58.817)
So anyway, so you can imagine if your compulsion is rumination, then talk therapy can like really do a number on you. And you're like, I don't know why I'm not getting you at the bottom of this. And it's like, well, yeah. Yeah, it's not great. I do not recommend. So exposure and response prevention is basically

Jonny Miller (32:08.134)
I'm paying someone to ruminate more. Where is this working out? Like feeding the beast?

Dan Shipper (32:25.567)
Confront the willingly confront the things that most terrify you so like face the like really difficult thoughts feelings and emotions and do not compulse and There are different theories for how this actually works some theories are kind of like you basically Once you do this you sort of start to habituate to it. So they're not a scare anymore other theories are more like it's it's a little bit like

by not compulsing, you still have the terrifying thoughts and feelings, but you're not amplifying them. And if you don't amplify them by doing something about them, then they go away. So it's a little bit like, I don't know what a good analogy is, but you basically learn which activities of your mind serve to...

serve to churn the water up and make it even frothier and worse, and which activities of the mind serve to like, keep things sort of on an even keel. So you're not running away, you're kind of like either sort of staying where you are, like if you to some degree embracing it, know, accepting it, like all that kind of stuff. So it's a lot of that. And that started to really help.

once I, once I started to do that, but it still was not, honestly, still, it was still very hard. And so almost exactly a year ago, I started taking Zoloft and it fucking changed my life. That shit is like amazing. and it's. Yeah, it's so, I mean, it's, it's really for me, like everyone has different experiences.

Jonny Miller (34:03.972)
Wow. Wow. I wasn't expecting you to say that. Interesting.

Dan Shipper (34:15.137)
it took me like three or four times to get on because the experience of getting on was really hard and I can talk about that. but for me, for OCD, it, it has been definitely the single most important thing I've ever done. and, and having it has unlocked so much other stuff, like in therapy and other parts of my life that like were completely not accessible. Cause I was just like in 24 seven, like

you know, crazy mode basically. And, and, and this is coming from someone like I spent a lot of years like doing a lot of different things like everything I could possibly try. Like you, you name it. I've tried it basically. Because I think for me, like I was definitely one of those, like, I don't want to just like take meds. Like I want to deal with my issues type people. And I think that was actually a huge mistake for me. And I'm very, very

happy to be on SSRIs. They've been life-changing.

Jonny Miller (35:19.687)
Wow, have so many questions. So yeah, I do, I'm curious. When you mentioned that I think that was a great articulation of OCD, it sounded to me almost like that there was like, you know, a really intense protector part. And I'm imagining that you explored internal fighting systems to some degree. Did you find any...

Dan Shipper (35:25.569)
you

Jonny Miller (35:46.668)
IFS work or particularly kind of like a somatic exploration of the part or like identifying that part in your body and then kind of exploring that. Was that a trailhead that you you ventured down at all?

Dan Shipper (36:01.173)
Yeah, and I think...

Dan Shipper (36:10.751)
I think, what do I feel about this? All of those modalities are helpful. And like IFS for example.

It can be done in a really skillful way and it can be done in a way that like makes things a lot worse. And I have found that those things are more helpful points of view or ways of looking to experiment with now that the like temperature, yeah, is a lot lower.

Jonny Miller (36:31.995)
Mm-hmm.

Jonny Miller (36:48.602)
the intensity is kind of like dialed down a little bit. Yeah, totally.

Dan Shipper (36:52.139)
Cause when it's really high, you're like, yeah, talk to the protector. And you're like, I don't know what it's saying. Like it's fucking crazy. know? and so like, I'm, I like all that stuff, but also, and it depends, like all this stuff exists on a spectrum and whatever. But, the, the level of issue that I was dealing with was high enough and persistent enough that that was like not helpful or really available. and now I'm like, you, I can do, I'm doing regular talk therapy and it's

Jonny Miller (36:57.57)
Yeah, yeah. Totally. Yeah.

Jonny Miller (37:16.688)
Mm-hmm. Yep.

Dan Shipper (37:21.663)
Amazing, it's so good for me. And I'm into like Jungian stuff right now. And like, there's just a lot of like cool stuff that's like, that's opened up. And maybe I'll have a resurgence of IFS. But it was not the right thing for me when I did it, unfortunately. Yeah.

Jonny Miller (37:27.696)
Have

Yeah.

Yeah.

Jonny Miller (37:41.7)
Yeah, I think it's really helpful to kind of hear your story as a kind of very compelling counterexample for when and where SSRIs can be like life-changing, it sounds like. I think for me the kind of the broader theme that feels important is like whatever it takes to bring someone back into their window of tolerance.

whether that's like, I'm a big fan of bottom-up practices that help people to kind of really downshift, but there's many ways of doing that. And it's probably frankly much easier and more accessible to have medication than it is to do an NSDR every day or a certain breathwork practice or something like that.

Dan Shipper (38:21.353)
It depends. like, what's, you know, the thing about medication is it's not like this cure all where you just take it and you don't have to do anything like it. It's like, it's like taking creatine or whatever. Like if you take creatine and you work out, you're going to get jacked. But if you just take creatine, like maybe you'll like get a little puffier or something, you know? and, and so, like this stuff has helped me in the context of a lot of other.

Jonny Miller (38:42.284)
You

Dan Shipper (38:51.285)
work and it has just like made that work available where it's like, I was trying to run a marathon on like a broken leg and people were like, well, you just need to get grit through it and face your fears. And like, you gotta like talk to your protector. And I was like, okay. But like it wasn't working, you know? and so I think the thing that what I feel is,

Jonny Miller (38:54.99)
Mm-hmm.

Jonny Miller (39:03.27)
It's like...

Jonny Miller (39:08.099)
Yeah.

Dan Shipper (39:16.637)
What you're trying to do typically is get to a place where you're, you feel like you're growing and you have a sense of wellbeing and you have a sense of like, to some degree agency over your life and, and whatever, like there's some amount of like flourishing and forward movement that you want to be like getting to more or less. And there's lots of different ways to do that. Some of them are like psychological, some of them are physiological. Some of them are like.

pharmaceutical, some of them are going to be so social, like there's lots of different like levers and different people are going to respond to a different combination of lever levers. And I think the worst thing you can do is be like this lever works for everyone. And if it doesn't work for you, that's because you're not trying hard enough. Because I think that's the message that a lot of people get. And and the second worst, maybe maybe even worse than that is saying that lever is for losers. You can't use that lever because if you do, you're giving up.

Jonny Miller (40:00.516)
Yeah.

Jonny Miller (40:04.884)
Yep.

Jonny Miller (40:12.415)
Mmm. Mmm. Mmm.

Dan Shipper (40:14.797)
and I think basically like, giving people license to kind of like explore the richness of the different ways that they can like learn to grow and become themselves is like the most important thing. And, it's definitely not one thing for all people. It's like all people have, you know, there's so many different ways of looking at the world and so many different ways of like working on working with yourself. And I think.

people just need the space to do that.

Jonny Miller (40:46.715)
Yeah, I love that. I think from my perspective and honestly my journey as well, the principle of like self experimentation and not just blindly taking whatever culture or even, you know, well-intentioned therapists might say, but trying stuff for yourself and then reflecting of like, did that help? Was that supportive? Like, how do I feel? It feels like the path through regardless of whatever someone's exploring or dealing with.

Dan Shipper (41:08.085)
Yeah. Yeah.

Dan Shipper (41:15.669)
Definitely. I think that that is honestly, and most interestingly, like one of the big shifts that like growth creates. It's like, it's the thing that you need, but then it's also the thing that you need to like, I guess, figure out how to have before you have it, which is being pretty, like a lot more centered in how you feel and what you want and what works for you and taking a lot more ownership over like.

Jonny Miller (41:15.75)
Jonny Miller (41:33.183)
You

Jonny Miller (41:40.447)
Mm.

Jonny Miller (41:44.735)
Hmm.

Dan Shipper (41:44.873)
yourself and and whatever and that's always easier said than done, but Honestly, that's one of the like big things that Zoloft has done for me which I think is like really under discussed is

it's created much more of a, a barrier between me and other people in a, in a healthy way, like a, like a semi permeable membrane where before there was nothing. like an example would be like, I would be hanging out with you and like, or maybe we'd be on the podcast and I would like sense that maybe you were like a little bored or something. And, I would feel your motion.

Jonny Miller (42:06.557)
Hmm.

Jonny Miller (42:11.487)
Mm-hmm.

Dan Shipper (42:27.325)
in my body and I would feel it as myself. Like I would feel turn you judging me into me judging myself basically. And it was just very hard. everything was just so sensitive and vulnerable that like you have to have all these like defense mechanisms and all this stuff to like guard the like really you're living with your like heart outside your chest basically and and everybody else is in it all the time, you know.

Jonny Miller (42:31.241)
Mm-hmm.

Jonny Miller (42:47.965)
Ahem.

Jonny Miller (42:52.637)
Yeah,

Dan Shipper (42:58.011)
And getting a little bit of that space made it much easier for me to actually be like, no, this is how I actually feel. And like, if someone is upset at me, that's fine. I'm, interested in what they, what they're saying, but like, also it's not, I get to decide whether or not that's like, I think that's right. You know? and paradoxically that actually makes it much easier to deal with like.

Jonny Miller (43:06.399)
Hmm.

Jonny Miller (43:14.322)
Mm-hmm.

Dan Shipper (43:24.385)
deal empathetically with like difficult interpersonal situations. Cause like once you're threatened, it's a, it's over. And if you're not as threatened and your sense of self is not on the line in every interaction and it's more solid, then you get a lot of, you get a lot more mileage and it gets very confusing for people because you're like, well, shouldn't I annihilate myself? And shouldn't I like transcend the self or whatever? And I think that that gets,

Jonny Miller (43:28.301)
Totally, yeah. Yeah, yeah, yeah. The fence has come up.

Jonny Miller (43:36.018)
Mm-hmm.

Dan Shipper (43:52.135)
especially for like sort of people pleasery, which I put myself in that category, people pleasery type people, people with like a little bit who are very outwardly sensitive to other people and other other things. I think that that ends up getting misinterpreted. And you're like, yeah, I'll just do whatever I just go with the flow. I just do whatever other people want. And that's like

Jonny Miller (44:06.687)
Mm-hmm.

Dan Shipper (44:16.737)
because I don't have any ego, you know, like I've, it's ego death or whatever. And you're like, no, no, no, it's different. It's a different thing.

Jonny Miller (44:21.368)
It takes a special amount of ego to have that perspective. Yeah, that is a very refined form of egoism. Yeah, yeah, I'm actually, I'm glad we're going down this direction. I mean, my, so on the sensitivity piece, my former fiancee, Sophie, she...

had been diagnosed with bipolar and she was also very, very sensitive but also attuned. So part of why people loved her was she was so...

like creative and sensitive to the world. think that's the best way to put it. when she took SSRI, she really hated it because she felt like it kind of quashed some of that creative impulse and aliveness. And so what I'm seeing in you is that from the outside, at least, it looks like your creativity is still full steam ahead. You are churning out the creative output and still in touch with that aliveness.

So guess you're one of the first people that I've met actually who's both benefited from the, let's say, the sensitivity-reducing effects of SSRIs, but hasn't had the downside of losing that sense of aliveness and creative sensitivity.

Dan Shipper (45:36.819)
Yeah, there's a lot to say there. So first of all, with bipolar, it's a bit different because with bipolar, you're not just dealing with necessarily like a normal sense of creativity, you're dealing with like the manic high. And a lot of people who have that, they just like that high, like who wouldn't like it's an amazing feeling.

Jonny Miller (46:03.624)
Actually in her case I believe she had like type 2 bipolar which I don't think has the manic... it was more of just the depressive episodes and the anxiety.

Dan Shipper (46:06.878)
interesting.

Dan Shipper (46:11.111)
Interesting. and, and, so let's, let's just put that to a side for a second. Like I think also it's really important, like, different people react differently and certainly some people feel like it takes off the like high in a way that like, or the positive emotions in a way that like, they can't deal with. And I think like, there's probably, if I had to, if I'm being really honest, there's probably some.

slight level of like joy or ecstasy or something that like it's just harder a little harder to reach but it's taking off way more of the bottom than the top and like way more and what's interesting is like the alternative which is just being in emergency mode all the time like that's way worse that's way way way way worse and way worse for my sense of creativity and like fun and like enjoyment and all that kind of stuff like it's actually just inaccessible

Jonny Miller (47:07.209)
Mm-hmm.

Dan Shipper (47:09.053)
So yeah, think it has actually really deeply enriched things and enriched my experience. like another really good example is I can feel like jealous now, which I would not have been able to feel before, because like morally it would have felt so dangerous to feel jealous that it would have been like converted into something else. And I've been like, that's not.

Jonny Miller (47:31.553)
Mmm, yeah, yeah, yeah.

Yeah, interesting, interesting. Yeah.

Dan Shipper (47:36.961)
I don't have jealous. I'm there's something else. So like my my color palette of emotions is like way richer.

Jonny Miller (47:42.771)
And would you attribute that to having like an increased sense of embodied safety and like capacity and window of tolerance so that some of the more edgy emotions you feel, okay, I'm actually safe to explore this. Whereas before it would have just sent you off the rocker. Huh. That's really interesting. Yeah. I'm really, I'm appreciating this. Like this is very, it's like new territory for me.

Dan Shipper (47:53.653)
Basically. Yeah. Yeah.

Dan Shipper (48:06.497)
Sweet. I'm really glad. Yeah, I think that they're really under discussed now and misunderstood. And it's funny because they're so common. think there's so many people who are taking them that don't talk about it because it feels kind of bad. You're like, maybe I shouldn't, especially in our circles. And certainly, I think like...

it's much better to start with non-pharmacological interventions. But if you're stuck for a really long time and nothing's working, they can really help.

Jonny Miller (48:51.727)
Mm-hmm. Yeah.

Jonny Miller (48:56.947)
Hmm.

Jonny Miller (49:03.941)
Is there anything else on this kind of topic that you want to speak to or share? Because I also, do want to kind of, there's this like part of me that's like pulling me into the AI black hole. yeah, is there anything else kind of on this theme that feels maybe interesting or relevant or any questions or open questions that you have right now that you're kind of exploring?

Dan Shipper (49:35.915)
The big thing for me currently, there's a couple of things. One is in the same way that I think my sense of self was very tied to like kind of people around me. It was also quite tied to my work, my company. And if you're the kind of person who is like sensitive to people and feels a lot of responsibility for them and like feels their needs kind of like

taking over yours and your body, know. Starting a company can be really appealing because you're like, I'm going to get to be the one that makes the decisions, you know, like it's my company. And it's sort of like, I get to create my own world, you know, especially if you're like a nerd, because it's not just like my own world and I get to make decisions, but I'm also at the center. like, you know, people have to pay attention to me.

Jonny Miller (50:32.339)
Hmm.

Dan Shipper (50:33.685)
You know, and so if you're like, if you had a hard time in middle school, it's like, that's the dream, you know? and so your company becomes this like solution to this emotional problem. often, like what, ends up happening is all those same things still happen. You know, you still feel, even though you're, you're the CEO for me, even though I was a CEO, I still felt beholden to everybody else. And so it's like, I'm the CEO in name, but like,

Jonny Miller (50:45.533)
Hmm. Hmm.

Jonny Miller (51:03.336)
Mm-hmm.

Dan Shipper (51:03.979)
can't actually make decisions. And everyone else is, it's not their fault. Like they're expecting me to, I just like couldn't. And now there's a much, now that there's more separation, like opens up, it's just way more fun, but it just opens up a lot of range, like a much larger range of decisions that I could possibly make. And that has made me much more effective and it also has.

you know, it opens up like, okay, like what I want to do with this company and all that kind of stuff. Cause like, if it doesn't work, it's fine. I mean, it it would suck. would hate that, but it, it's not, it's not the same as when it was like completely the same thing as me. So that's one, like one big thing that I'm kind of exploring right now. And then the other one is,

Jonny Miller (51:43.367)
Yeah, right, right,

Dan Shipper (51:56.233)
I think OCD before it's treated is like you're living in a hell realm, basically. It sucks. OCD once it's treated is a little more like... It's a little bit more...

You still feel it, but it kind of comes in and out and it's like, it just doesn't bother you as much, but it's still kind of there sometimes. But that still kind of sucks. And especially if you have OCD and you're a little bit obsessive, you're a little bit perfectionist, you're a little bit perfectionistic. You're like, I want to get rid of it. Like let me get rid of it. And that obviously makes it worse. it's a whole, it's like, it's this sneaky motherfucker where...

Jonny Miller (52:36.221)
Mm-hmm. Mm-hmm.

Dan Shipper (52:44.243)
And it's the same thing as every other kind of emotional thing, where it's like, once you're like, I've definitely beat it, it's definitely gone. Like, it's actually that the thing that's saying that is the thing you're trying to get rid of. It just pops up behind you. Anyway, so I felt like I just needed some way to like.

Jonny Miller (52:57.905)
Yeah, totally, Yeah, yeah, yeah. Yeah. Yeah.

Dan Shipper (53:10.657)
Because I think there's a lot of aspirational models of living that are like, yeah, like, and I just now I just do John at practice all the time. And I'm just like fucking blissed out, you know, and like, I'm sure that that is like available to me, but like, also, it's not going to be available in like a 24 seven kind of way. Like, I'm just going to have injuries of thoughts like that sucks, you know? And so I've been looking for like, more aspirational models of like,

Jonny Miller (53:31.401)
Hmm. Hmm.

Dan Shipper (53:38.443)
how to live like this that don't feel like either I need to get rid of it or don't feel like I'm giving up or something like that. so one of the things that's just been really beautiful for me recently, like very opening is like the idea of Twilight and not the movie or the book, not vampires, like the time of day.

Jonny Miller (53:41.087)
Hmm.

Dan Shipper (54:03.617)
For any Twilight fans, I'm not necessarily harping on it, like I just haven't read it, it's just, you know...

Jonny Miller (54:03.948)
Thanks for clarifying. I've heard that there is a vampire community in New York City so I didn't want to rule that out.

Dan Shipper (54:18.433)
But yeah, it's sort of like the idea of Twilight, is the reason I like Twilight is it's this border between night and day. And it happens both at dawn and at dusk. It's like the time when the sun goes beneath the horizon or is still beneath the horizon. And but it's still light because it's still close enough to the horizon that it's shedding light, basically.

And so what's interesting to me about Twilight is it's a very It's it's at the border. It's a it's a liminal state. It's It's both it's both light and dark at the same time and what's really cool about Twilight to me is

Because the sun is below the horizon, the light is very diffuse. So it lights everything in this like very soft light and there are no shadows because it's coming from everywhere. And that feels like OCD to me or at least how to hold OCD in a way that like I resonate with. Like, I don't know what you would call like archetypally or mythologically or whatever.

Jonny Miller (55:19.188)
Hmm.

Dan Shipper (55:37.921)
Where it's it's you're on the borderline like there's amazing things happening. There's like darkness happening There's like all this stuff and you're like kind of learning to be the master of Twilight, you know and and the way to do that I think is like be able to hold it in in that sort of soft light where there are no shadows and being able to like be in that like there's this complicated in between and

Jonny Miller (55:47.743)
Mm-hmm.

Jonny Miller (55:58.995)
Hmm.

Dan Shipper (56:07.681)
So that's been really, I don't know, beautiful for me. And I think that actually just connects to a lot of other things in my life. Like I actually, I really like being at the borders of things. Like I like doing the like, the AI stuff and the creativity and the psychology and the philosophy and like all this like stuff. And I like people who do that. And I think at every, a lot of those people are, we have a lot of those people internally, people who play at the borders.

Jonny Miller (56:22.271)
Hmm.

Dan Shipper (56:37.241)
and, anyway, I could talk about this forever and there's, there's like deeper stuff here too, but, I've been blabbing and you probably want to talk about AI. So I'll leave it there.

Jonny Miller (56:38.035)
Mm-hmm.

Jonny Miller (56:47.496)
You

mean, is part of me wants to just say, it and just kind of keep going and maybe we'll do a round two at some point. But yeah, I mean, what comes up for me around what you just shared is, is that like for me, kind of my philosophy around what I've been calling nervous system mastery is essentially kind of around the question of like how...

might we or can we welcome the full spectrum of our kind of human experience and to be able to be on those borders, be on those edges without getting overwhelmed. in my experience, it's actually kind of, as you mentioned earlier about like trying to like trying to get rid of the OCD is actually the very thing itself. And it's like the way in which we resist the thing, it is the thing that causes the suffering. Right. And so for me, the interesting question is like,

Dan Shipper (57:33.003)
Yeah. Yeah.

Jonny Miller (57:45.852)
how might I, how can one create the conditions where it is possible to allow and surrender or even kind of like lean into and love the resistance and then the thing behind the resistance or the thing that it's guarding. And so it seems like we're kind of like exploring similar.

threads or questions. And for me, the juice, I guess, is that on the other side of that, there is often more aliveness and I can see like a richer texture of life, right? It's like the kind of the saturation is turned up. And I think that's why, I'm, you know, maybe prior to this conversation, I've been very hesitant to...

even look more deeply into SSRIs because I'd viewed that as like turning the dial in the other direction. But what you shared around like, you know, let's say support from pharmacological support to increase that sense of embodied safety so that you can then go and explore these richer territories, like I'm like, wow, that makes total sense. That resonates with me.

Dan Shipper (58:50.41)
Yeah. I love that. I love that. And yeah, I mean, I think, I think we're thinking about the same stuff and I think the Twilight stuff is it's an outgrowth of that or that feeling of like, okay, yeah, like part of the problem is that I'm resisting the thing here and like, learning to like, accept it or love it or embrace it or whatever is like, or be willing to have it or whatever. Like there's lots of different ways to say that, is I think part of the healing process.

And for me, it's easy to say, yeah, I'm just gonna accept it or I'm gonna love it or whatever. And it's really hard to do. one of the things that works, I think, is...

coming up with a story or a reason or like a an aspiration or like a myth or something that something that just like really resonates with you. It's like for whatever reason. I don't know. Twilight just resonates with me. Like I one of the things I love is I step out every day and it's there. And so it's this like constant reminder of like how I want to like live and how I want to hold what's going on and all that kind of stuff. And I think

Jonny Miller (59:57.443)
Hmm.

Dan Shipper (01:00:11.553)
I think it's great if someone else likes that too, but like the point is like you get to be the creative author of like what actually works for you and and I think learning to figure out how to tell yourself stories that work for you instead of like beating yourself up like man I forgot to gratitude journal today like damn it you know and it's like the point is not to like force yourself to like gratitude journal it's like actually like

this delicate process of finding things that have that resonant quality for you and then just lightly and loosely bringing them back and knowing that it's not gonna always feel good and whatever. But I think that that is a critical life skill that don't invest in because they...

I think that you basically, you look for other people's stories and then you just, you're like, why isn't it working for me? And sometimes it doesn't, sometimes it doesn't, but just knowing that you have the freedom to like figure out what resonates is like, think such a core little unlock for, it was for me and I think it probably is for a lot of other people.

Jonny Miller (01:01:28.152)
Mm.

Yeah, I've been, I can tell you've been diving into Jung. I was reading some of Robber Bear's soul-making, or rather listening to some of Robber Bear's soul-making Dharma, and I think the kind of like imaginal practices, which I think relate to what you've just been sharing, actually like... Nice, great. Yeah, and it feels, I mean, it feels very...

Dan Shipper (01:01:45.269)
Yeah. I'm, you know, deep into that shit.

Jonny Miller (01:01:57.912)
just under underrated and maybe just less talked about in the kind of ecosystems that we're both a part of. One thing that came to mind for me as you were saying that was during my kind of like grieving journey, this story came to me of, okay, like I had.

Sophie's ashes, she was my former fiance, we like poured them over this river and they kind of like went out to sea. And the story that came to mind that was deeply meaningful for me was like, taught me what it meant to love. And that now that like her atoms were like literally a part of the world, it was like this parting invitation for like, how can I fall in love with the world and you? And so that was kind of the question that I like,

walked around in. like literally like, was like okay, she's like quite literally like the her atoms like part of like how can I fall in love with with the world and that became it was like a lens through which I viewed and as you can imagine it was like a very generative kind of like poetry inducing perspective and I think there is an art to

those types of stories. And there's also a way in which I think those stories naturally arise from certain emotional states and ways of being. And so maybe there's kind of a chicken and egg type thing here of like, do you start with a story or do you start with a state that then naturally creates those types of stories?

Dan Shipper (01:03:26.379)
Yeah, that's so beautiful. Thank you for sharing that. And yeah, like I think paying attention to those things. Yeah, you don't have to necessarily invent it. Like you can just be like, yeah, that actually that moment just, it just hit me. like, I have a lot of stuff like that. another one that I'm really interested in is

Like I do a lot of writing that's sort of like at the intersection of like technology and how technology changes, how we see ourselves and how we think about the world and technology and philosophy and like creativity and psychology and all that kind of stuff. one of the things I love so much is I get to like, read all these people for like thousands of years that have like grappled with the same questions and have had different answers to them and like, and, have been around different technologies. And so have had different conceptions of like,

what the world was like and what they were. I love just like imagining being part of that conversation and being like having those people around me. You know, it's like so cool. And it feels so motivating to be like connected to those people through the thoughts that we think, you know, or the work that we do.

Jonny Miller (01:04:28.108)
Mm-hmm.

Jonny Miller (01:04:52.32)
Mm-hmm. Yep.

Dan Shipper (01:04:54.222)
like a sort of intellectual lineage and like finding people that

I can kind of tell they just have, I would have liked them, you know? Even if it was 500 years ago or whatever. Or I could have told they would have annoyed me, but I would have respected them or whatever. And being in communication with them in a way that's not, it's much richer than kind of like, yeah, I'm standing on the shoulders of giants. It's like you, like,

Jonny Miller (01:05:05.41)
Hmm.

Dan Shipper (01:05:28.597)
visualizing or imagining them around you or whatever and I think we have like a a little bit of like a aversion to that because you're like, I don't want to like go crazy or like, you know, I don't want to lie to myself is another big one. I feel silly all that kind of stuff and I think Just paying attention again to like what feels good and what feels growthful and generative and rich is like That's how you kind of get through that if that's what works for you different things work for different people and

Jonny Miller (01:05:52.833)
Mm-hmm.

Jonny Miller (01:05:56.856)
you

Dan Shipper (01:05:58.751)
Yeah, I love Robber Biz. mean, the problem with the imaginal stuff is like, it's so, it's pretty dense and there's no like, with seeing that freeze, like all the emptiness stuff, it's like laid out in like a system. And the imaginal stuff is much more like there's like 40 talks and like they all are self-referential and you're like, what the fuck is Eros? Like, I don't know. But,

Jonny Miller (01:06:12.182)
Mm-hmm.

Jonny Miller (01:06:18.331)
Yeah, yeah, I totally agree.

Dan Shipper (01:06:25.163)
But he has this series of talks that I've just been listening to on repeat for the last couple of months that are just, it's exactly like what I'm thinking about, what I'm writing about. think they're so appropriate for this moment. And it's actually very related. It's where Twilight came from, to be honest with you. So the first is, it's called Questioning Awakening. And then the next one is, it's like Buddhism after modernism. And then,

Jonny Miller (01:06:35.852)
Mm-hmm.

Dan Shipper (01:06:52.629)
The last one is in praise of restlessness. And the Twilight stuff comes from the, the in praise of restlessness talk because he talks a lot about different ways of seeing the world, you know, and, also different like archetypes that embody that way of seeing. like an archetype would be like an Apollonian way of seeing the world. Like the God Apollo is like very rational.

It's very systematic. Everything's in its place. Everything is very mathematical, analytical. Very, yeah, exactly. And then the Dionysian is a lot more ecstatic, maybe what you would imagine to be more woo or more artistic or creative or whatever. But the one that he resonates with, and it's why I like him because I think my personality is actually very similar, is

Jonny Miller (01:07:27.919)
Like a left hemispheric perspective basically.

Dan Shipper (01:07:52.235)
Hermes, who is the messenger god.

Jonny Miller (01:07:56.909)
winged messenger. story, my first company in university was called Winged Flip-Flop, inspired by Hermes. Yeah.

Dan Shipper (01:08:03.233)
No way. That's so funny. I love that. Hermes is like the messenger god, which I think is actually quite appropriate for writers. Because there's a way of writing where it feels like you're sort of tapping into something else. Like you're just sort of like the messenger.

Jonny Miller (01:08:19.781)
Also kind of the bridge between like the archetypal kind of god realm versus the human realm, right? It's the bridge builder.

Dan Shipper (01:08:25.481)
Exactly, he crosses borders. He goes from gods to humans, he leads people to the underworld. He's also the god of commerce, which I really like. He's a little bit of a trickster, so he's got some stuff where he might lead you astray a little bit. So watch out for me. But the core thing there, and I think that...

Jonny Miller (01:08:43.328)
Hehehehehe

Dan Shipper (01:08:55.097)
Rob Burbea kind of like vibes with that I also vibe with is that like, there isn't, one privileged perspective on the truth or one privileged way of seeing the world. And it doesn't mean that everything is relative and there's no truth or whatever, but there's not one privileged truth. and it's very useful to be able to look at things from different perspective and with different lenses. and that's the sort of like hermetic way of being, it's like a much more like restless like

searching without like a, without trying to find an answer, but like just searching. And the Twilight thing comes from that because, you know, Hermes is sort of the god of boundaries and Twilight is a sort of symbolic embodiment of boundaries between light and dark. So, and I think that this has a lot, a lot of overlaps with some of the stuff we were talking about earlier with like,

paying attention to what works for you and like, you know, try different things and just experiment. You know, it's like, that's why I love Rob is he's just so, figure out what works for you. Here's like 50 different things that you can try, you know, as opposed to like, my method that I invented is like the only thing that works, you know? Yeah. Yeah.

Jonny Miller (01:10:01.313)
Mm-hmm.

Jonny Miller (01:10:10.544)
Yeah, yeah, yeah. It's the three-step shipper method.

Jonny Miller (01:10:24.492)
Yeah, I really didn't anticipate this conversation going in this direction, but I love that. And I remember, you when I was doing philosophy, one of the things I appreciated about, I think it was Nietzsche when he talked about like, is no view from nowhere.

when it comes to that perspective, it's in some ways antithetical to the current culture, which is very much pedestling science as the of capital T truth, almost in the same way that former cultures had with certain religions. think that is kind of the way that we're seeing the world and something that I've, maybe this will tie back to AI. dear.

Dan Shipper (01:11:04.745)
I can tie back to AI. got you. I got you. But keep going.

Jonny Miller (01:11:08.884)
Yeah, what I wanted to like, one of the things that I haven't talked about much publicly, but I really, I got a lot of value from the kind of king warrior magician lover framework and how those four very different perspectives, which also map onto for me, like parts of the body, like magician is kind of like the mind, kind of like the Apollonian perspective. The lover is obviously the heart. And then the warrior is like the gut, like the one that sets boundaries, makes decisions, that follows through. And the king...

Dan Shipper (01:11:18.945)
Mm-hmm.

Jonny Miller (01:11:38.61)
for me is analogous to like the internal family systems like capital S self, the one that kind of like ensures that they're all in alignment and is like gets them to communicate and be like which perspective in this moment is most generative or most appropriate to the surroundings. And I think that being able to fluidly switch between these different modes of beings and I think that having like almost archetypal images is incredibly helpful because it helps us to like move fluidly between them.

is just a really under appreciated skill. also, I mean, maybe this will come back to AI as well, but there's a way in which I used to journal between these different parts. And you could probably have four different AI bots that represent those different archetypes. And you kind of simulate conversations or decisions between them. Anyhow, yeah.

Dan Shipper (01:12:30.485)
Yeah. No, 100%. And like, and yeah, I mean, I can, I think I can, I can get us back to AI here. Okay. I think I could do it in five minutes. It's something that I've been playing around with a lot because if you look at the history of the West, it's very rationalist. It's very like, okay, what is it to know something? Starting with Plato.

Jonny Miller (01:12:39.137)
We have like five minutes left.

Dan Shipper (01:13:00.457)
and Socrates, knowledge has to be explicit. has to be, you have to have a definition. have to be able to like define your terms. And if you can't define what you're doing, like, you don't know what you're doing. And the person who knows like, has that sort of explicit knowledge and you can see that, you know, like, sort of picked up again in the Enlightenment with like Descartes and Newton like really and Galileo like really like,

made this take off because Galileo used the telescope and is thinking about mathematics as the language of the universe. That analytical mathematical way of thinking is the way the world works. That's actually the truth is the math. Newton is like, same thing, calculus, it becomes such a powerful thing for us.

is finding these like scientific mathematical explanations of the world. And it's brought a lot to the West, like everything. We're doing this because of Galileo Newton and that whole like rationalist sort of worldview. But it's I think it it that way of seeing the world, it's like everything is sort of just like, you know, Adam's bouncing and like and it what it is to know something is is

Jonny Miller (01:14:04.375)
Mm-hmm.

Dan Shipper (01:14:29.661)
Knowledge is by definition like something Analytical it's theoretical. It's something that you can like write down and and and Expressing in an equation or prove scientifically Is is kind of limiting and it actually like It doesn't work in a lot of areas of the world unfortunately that especially in very very complicated areas of the world and we've been really hesitant to

look at that and look at how limiting scientific explanations or sort of this rationalist outlook is because we haven't really had any good replacements and they're very useful. Like they're very useful for making predictions about the world. What I think is quite interesting about AI stuff is it is a suddenly we have a tool where we can make predictions about

very complex areas of the world that we have no scientific explanations for. the way that like a language model or any kind of other deep learning model makes predictions is much more like, it's much more like human intuition than it is like a rational reasoner. And what's really interesting to me is because we're in the West, when they first tried to make AI starting in the 50s, like,

Jonny Miller (01:15:44.237)
Hmm.

Mm-hmm.

Dan Shipper (01:15:55.925)
They started by trying to make it a rational reasoner. Like they started by trying to make it be able to like logic its way step by step through problems. And what they found is it was like incredibly brittle. And the complexity of problem that I could handle was like so low that it was like, wasn't useful. as it started to get to a much higher degree of complexity problems, like the branching tree of possibilities for logical possibilities for it to reason through just became so enormous that it just like didn't work.

Jonny Miller (01:16:18.072)
Mm-hmm.

Dan Shipper (01:16:25.385)
you would need more competing power than you can get in the universe to like reason through like something that a toddler would do step by step. And

And and so and and things only started to work once we got rid of the kind of like underlying rationalist assumption and like move to this more Deep learning which is much more opaque. It's much less explainable. It's not rule-based and what looks much more like human intuition and so I Think like my hope is that

Jonny Miller (01:16:55.126)
Mm-hmm.

Dan Shipper (01:17:06.527)
Now that we have a tool that works in a way that like looks a lot more like intuition, it will kind of like make the invisible intuition that is like the bed of like all of our lives and from which rationality emerges like more visible to us and accord it a lot more respect. And also it like, when you can put intuition into a tool, you get a lot of the same properties as

Jonny Miller (01:17:22.552)
Hmm.

Dan Shipper (01:17:36.565)
you get with scientific explanation. like the reason why scientific explanations are cool is like, they're reproducible. I can write it down and give it to you and then you can use it. Human intuition, which is like incredibly fucking powerful. Like, you know, the intuition that you've built up for like working with people and working with their nerves and nervous systems is like, it's crazy powerful. Even if there aren't like, even if you don't have like the underlying, you know,

neuro neurological explanations for every little thing you're doing. Like you kind of just fucking know. and that's another way of knowing that's really important. and, the problem is it's all locked up in your head. So if I can't get time with Johnny, like that sucks. and maybe you can write it down, but that's a very like lossy way of doing it. It's like what you can write down is like, it's like the

Jonny Miller (01:18:07.384)
Mm.

Mm-hmm.

Jonny Miller (01:18:23.64)
you

Dan Shipper (01:18:27.007)
It's like a photocopy of a photocopy like 10,000 times and I can get like the outlines or whatever, but it's not the real thing. But what's cool about machine learning is you can just copy the weights. Like you could just put it on another computer and you get that intuition somewhere else. and so, I'm hoping that it will sort of start to shift the, the emphasis.

Jonny Miller (01:18:39.714)
Hmm. Hmm.

Dan Shipper (01:18:52.346)
or, or help us see the like invisible intuitions that are like, guiding how we run our lives and how we make things and how we see the world. and allow us to work with them in ways that like, we'll make things better for everybody. so yeah, we'll see.

Jonny Miller (01:19:07.126)
you

Jonny Miller (01:19:15.739)
Beautiful. I want to share one thing and then we'll wrap up with a few rapid-fire questions and maybe this will act as a teaser for a part two where we will purely focus on AI because there is... I probably have like, don't know, like 3,000 words of notes here that I was like...

Dan Shipper (01:19:32.065)
Great. Sorry to disappoint folks.

Jonny Miller (01:19:43.666)
But what you just shared kind of reminded me of, and this is something that I'd love to dig deeper at some point, is I finished reading this book called The Experience Machine by Andy Clark, and he basically has this model of the way that our brains work as basically as like prediction machines, and that they make predictions in order to minimize prediction errors, which seems like remarkably similar to...

chat GPT doing like next token prediction, right? And this is like, this is really interesting to me. And I'm like, so I recently interviewed this neuroscientist called Mike Johnson and he has a very compelling theory that's in early childhood, certain experiences get stored as like tension in specifically in the smooth muscle tissue via this like.

latch mechanism. And I've been thinking about this as almost like a set of like custom instructions that are kind of like programmed into these like biological LLMs that we're kind of running that we're running in. And I think you're right in terms of like as the as these artificial intelligences increase I think they will reflect back to us more than we might imagine about how how we're actually programmed for kind of lack of a better word and

Dan Shipper (01:20:44.309)
Yeah. Yeah.

Jonny Miller (01:21:05.741)
I'm really curious about using AI to create basically like latch maps in people because the latches correspond with blood flow around the body. So you'd essentially be able to like show someone a map of like where their trauma is stored in a way. And I think that, I mean, these are some of Mike's ideas as well, but it has a lot of implications for even the story of humanity.

Like he believes that these latches allowed us to buffer our emotional responses for a longer period of time and thereby kind of create abstract reasoning and thinking which gave humans an early advantage like back in the day so that there's like a whole rabbit hole to go down there, but I Do you want to say something?

Dan Shipper (01:21:48.001)
Yeah. I think that's really interesting. And I think the thing that is most interesting or where I think you're going and where I'm going with this too is like,

technology always becomes a metaphor for how we understand ourselves. like Plato, one of his metaphors for the mind was a wax tablet. That's how he thought that's how memories work because you can like write in the wax and it like is it's like saved, you know. And Freud is another really good one that I love. the reason why you have this like sort of model of

repressed emotions that then like blow up in other areas of your life or become neuroses is the steam engine. And it's like a very, it's a pneumatic metaphor for the mind. It doesn't mean it's wrong. It's just like you're highlighting, when you have something out in the world that you can look at, it like illuminates something else inside of you that you like couldn't see. And it's never gonna illuminate everything, but it...

Jonny Miller (01:22:57.519)
Hmm. Hmm.

Dan Shipper (01:23:00.161)
it brings forward certain things that might not have been visible before. I think language models are doing the same thing in the fact that you're saying, it's sort of like custom instructions or like people, it's like fine tuning or whatever. All of these things are becoming much more available because we have language models as metaphor. And I think that can be really good.

Jonny Miller (01:23:25.595)
Beautiful. Well, this has been an unexpected pleasure. I really enjoyed this conversation. And I feel like I've learned a ton as well. Where for listeners who would like to follow you, listen to your podcast, AI and I, which I'm just going to make a plug for is freaking fantastic. It's one of my favorite podcasts. feel like I've, the main reason I'm fascinated by AI right now, I think is...

specifically because of you and those conversations you've had. They've been so, good. Where might you direct listeners to to find out more about you and the work you're up to?

Dan Shipper (01:24:06.145)
Thank you so much, I really appreciate that. You can find me on every, every.to. So we write a long form newsletter, one essay a day on what comes next in tech. I write every Friday a column called Chain of Thought, which is about all the stuff we've been talking about, but with much more of an AI flavor. And I have a podcast, AI and I, can...

Find it anywhere you get your podcast Spotify YouTube Apple Apple podcasts And I am on X at Dan shipper And yeah, this has been Amazing. You're yeah, I've loved chatting with you. Thank you so much for having me on

Jonny Miller (01:24:49.433)
Also want to give a shout out to you have two little side projects that I've been playing with. One is called Spiral and the other is Sparkle, which has turned my desktop from a minefield of downloaded bullshit into a very clean and satisfying environment to be in. So thank you for making those.

Dan Shipper (01:25:03.073)
Thank

Dan Shipper (01:25:12.779)
course, yeah. And if anyone's interested in the products we make, it's all bundled into the Every subscription. it's just on Every.to, we have a link that says Products, and you can explore all the things we make. And we're always launching new things. Got a lot of cool stuff in store.

Jonny Miller (01:25:13.489)
you

Jonny Miller (01:25:27.725)
Well, I'll do my best to put all the links in the show notes below as well. I like to close these conversations with a line from Rilke. He said, to love the questions themselves and live them now. Perhaps you will then gradually, without noticing it, live your way into the answer. And with that in mind, what is the question that is most alive in your consciousness and what question might you leave our listeners with?

Dan Shipper (01:25:53.333)
Wow, that's a good question.

Dan Shipper (01:26:09.153)
I mean, I think we've touched on some of them. It's like, how do I do my work in a way where I'm fully engaged, but my sense of self is not tied into it in every single way? how do I...

How do I aspire to Twilight? honestly, another one is just...

right now is like I have this big thing that I'm writing that is a lot of the stuff I'm writing about is like in this long form piece of some of the stuff we've we've chatted about it's much easier to talk about it than it is to write it because it feels so heavy and like I feel like it's important but like that makes it feel like I want to avoid it and so I'm just like how do I make it fun and

Jonny Miller (01:26:59.768)
You

Jonny Miller (01:27:03.953)
Hmm.

Dan Shipper (01:27:08.415)
I think that's the big one is like, how do I make it fun?

Jonny Miller (01:27:11.441)
It's very hermetic question to end the tricks, way to end the podcast on. Thank you so much, Dan. It's been amazing. Yeah, let's wrap it with that.

Dan Shipper (01:27:14.027)
Yeah.

Dan Shipper (01:27:22.461)
Awesome. Thanks for having me.

Embracing Twilight Zones, Self-Exploration & Living with OCD with Dan Shipper
Broadcast by