- Platform: meet
- Source: Read.ai 01KRBRDKNYPPY0HXAB1EPNTHFZ (via Ben Ornstein’s account, imported 2026-08-06)
Transcript
Ben Ornstein: I’ll go away for a few days up to Cape Cod in Massachusetts. So it’s going to be nice. Nice. Jacob Shipley: Hold on. Ben Ornstein: Yeah, we’re excited. Michael Houck: What’s up, guys? Sorry, I got a protein bar in my mouth. Ben Ornstein: All good. Hmm. Michael Houck: What’s going on? Ben Ornstein: Not too much. Just I was telling Jacob’s gonna be a big week. I’m gonna be making sure we’re all prepped. I’m probably gonna be working late every day. Just make sure everything’s good as clean as possible. Before I’m gone. Michael Houck: I appreciate that you’re out on you’re out on Friday this week. Correct. Ben Ornstein: And then yes, so Thursday night, I’ll clean everything up. And then I’ll be off for like the entire week until like, Monday, the I’m off from May 15, through like May 22, like back over the weekend, but like officially on like, the 25th Memorial Day. Yeah, well, I guess maybe I don’t know. Michael Houck: Yeah, so officially the 26th. Okay. Yeah, sounds good. Um, yeah, I if I send you slack messages, just ignore them. Like delete the app on your phone. I’ll probably just send things to get back. Ben Ornstein: So just yeah, I don’t know what I’m gonna have to do. I don’t know if I’m gonna like turn off slack notification, but it’s gonna be it’s gonna be weird for the first time. Like I’m literally not even gonna look so good. Michael Houck: Good. Okay, well, let’s, let’s dive into this. I think Ben, you can run the show here. Just want to Jacob get your thoughts on a little deeper on what we talked about a little bit over slack, but just kind of hear from you. Ben has some questions. I’ll probably have some questions too, but just want to understand how you’ve been using it and how it’s been beneficial. So Ben, you can take it away. Ben Ornstein: Yeah, just to start, I have a few questions down about process, but just overall, I’d love to hear how your experience with Casper and the agents has been just as a start Yeah, overall, it’s been good. Jacob Shipley: I think it has its pros and cons for sure. It’s, it has like the brand, and the voice and the tone, but there are some like nuances of like, how I would write things sometimes that it doesn’t like, I don’t know, just like some formatting things of like, it’s not this, it’s that or like things that are feel like give me the vibe of like this was AI written, but it’s hard to put my finger on what it is. It’s just kind of like, I kind of, you know, it just feels like, I don’t know how much of that is like, just, I know that it’s AI written. So I’m like looking forward to being hyper vigilant. But overall it’s been good. I think like with a client like Pierce, I’m not using it because he’s so like keen on like making sure nothing feels AI written. And so I just, I’ve been writing that myself. So I don’t know, before Casper, I’d been using just a Claude deal that I’ve kind of built over time of just kind of feed it top performing posts and training it on like how I would talk and how I would write. And I use that as a base. And then I go back and edit on top of that to try to make it, you know, not AI detectable. So overall, I feel like it definitely I don’t love how long it takes sometimes. Like it seems like it thinks forever, which I know that’s just probably part of it doing a good job. So, but overall it’s been good. Ben Ornstein: When you say it takes forever to, when it’s thinking, like when you send it like a query, like it just takes, like if you ask it to just create a post, like it just takes. Jacob Shipley: Sometimes it’s quick. Sometimes I feel like it takes a long time. It just kind of depends. I feel like it’s inconsistent. And how long it takes. Ben Ornstein: Interesting. Okay. Yeah. It’s the way it’s set up. There’s like different workflows that it runs. It shouldn’t take like an extreme amount of time. Jacob Shipley: Extreme. I mean, I’m talking like getting the like three minutes, maybe sometimes it’s like on the longer side. Ben Ornstein: Okay. That’s still longer than I expect. Next time that happens, can you flag it? Like tag me and be like, or not even tag in the thread, maybe just link it to me, like, hey Ben, just let you know, like this took three minutes. Just so I can like look and see what’s going on. But that’s good feedback. Yet Eddie’s like entire job is to edit and like humanize. So like when he lets em dashes, for example, come through as like a final post half the time. And I don’t exactly know why, because that like that should not happen. And I’ve tried to flag that to him. I ask him what’s like going on in his infrastructure, things you don’t need to, I don’t need to really mention here. But I don’t know why he does that sometimes, because that’s like literally his entire job. But what are the things that bother you the most? Like when you’re trying to get a post created? Jacob Shipley: Let’s see. Ben Ornstein: These damn emojis that they keep sending. I want to punch them both in the face. Michael Houck: I love it. It’s so funny. Ben Ornstein: I’ve tried to like tell them like, do not ever send emoji Slack reactions ever. I’ve looked in the infra and I’ve made it very clear. They’re still doing it. I don’t know. I don’t know what to do. Jacob Shipley: Luckily it doesn’t break anything, but it’s just annoying. The emojis like went like reacts to your previous message. Yeah. Ben Ornstein: And then he changes the reactions. It’s the dumbest thing ever. I have no clue why it does that. Michael Houck: But it’s weird. It’s like male technologists are like yawning. Yeah. Ben Ornstein: Yeah. It’s like the yawn, the yawn one. Michael Houck: I’m like, it’s like, Oh, I always feel insulted when I get the yawn one. Ben Ornstein: I don’t like the yawn one either, but yeah, I’m still, I’m still working on that one guy. Sorry. Jacob Shipley: Um, I think it’s hard to like put my finger on it, but it’s like, sometimes it’ll just like write a post. It’s like, I know in my head, there are three other directions that it could have gone that are better. And it’s like hard. So I don’t know how to train that of like the, the post they delivered was fine. It’s just like, Oh, I would have said it like this or that. And it’s almost like, it’s not worth the time to go through like actually go this direction. Like today, example, like maybe I can share my screen. So I said, write a post. Can you guys see my screen? UNKNOWN_SPEAKER: Yeah. Jacob Shipley: Write a post for Tim Draper, decade in review, talking about like these companies. And like, I never mentioned Bitcoin in this prompt, but it started talking about Bitcoin And then like this again, maybe it just doesn’t know, but most people thought I was eccentric at best. Like, I just know Tim would not like that. He’d say like, we don’t say what we’re not, or, you know, just, we don’t have any negative bias. So he wouldn’t like that. A decade later, the same, pattern has played out across every bet I’ve made. Well, that’s not true. Like, you know, that’s the whole thing with venture capital is like, it’s most of your bets don’t work out. And then he mentioned SpaceX, Tesla, for 40 years, I said a decade in review. So just like it kind of, and then he started talking about his grandfather. And I was like, that’s just like, not exactly the direction I would have gone. So then I just kind of started started over. And I just did some manual stuff. And I just looked through like, what are these companies that I mentioned that James pulled up and I just did. It was just quicker than, I felt like it was quicker for me to just like knock it out than to go through and like turn this version into something I actually wanted, if that makes sense. Michael Houck: Jacob, what about a scenario, because I’ve seen some of your conversations with it and I feel like, like my own feedback would be that I think sometimes you will prompt it in like very like ways that it allows it make it to different angles. And so it’s going to do what I would say, like, because I don’t want you to have to write out a super long prompt either. Right. But maybe voice notes, maybe like just like ramble to it about what you want the post to be about an extra level of detail. I don’t know if that’ll make it more directed and better. But I’ve noticed that in Slack, like that’s something I would I would try. Ben Ornstein: Yeah, that was that was going to be part of my feedback as well. And like the the best way for them to learn, it’s two ways, giving them actual successful posts, which is what I’ve done to initially train them on each client. And then the second thing is correcting them with feedback that is very explicit, that they can apply in various scenarios. Some of the things you said right there, you were like, this is something Tim would never say, he never framed something negatively. Like I’ve trained, you know, them specifically on something like that. But if you say something like that and see it like, hey, we never say, Tim never says anything negatively. Make sure to like include this to make this never happen again. You’ve seen how rude I am to them. Like you can be rude to them. I swear they learn better when you are. But that’s that’s a perfect scenario where you could do something like that. Jacob Shipley: Okay. Michael Houck: Yeah, Palmer Lucky says that he gets the best results from ChatGPT when he tells it he has kidnapped its family and is going to kill them. Ben Ornstein: I remember Greg Eisenberg said like, if you threaten to switch to another model, that works too. It’s like, it’s very interesting. But yeah. For like a specific question, in terms of like, Right now, if you generalize every client that you’ve used Casper and Eddie for, in a percentage basis of like, it’s 100% ready to send to internal review to Blake, where are we right now? Jacob Shipley: It’s not bad. It’s not bad at all. A little bit of time to go back through and then get it up to par. Some of them are much quicker than that. Some of them are much, like this one I’d say was like probably, you know, 0%, the one I just showed. But some of them are 80%, you know, some of them are much closer. It just kind of depends. Ben Ornstein: Yeah, for sure. That makes sense. Do, in general, do the agents let you just create content faster? Without sacrificing quality? Like I know in a sense that’s not perfectly answerable, but in general. Jacob Shipley: Generally, yes. Sometimes no, sometimes like 100% yes. So I’d say generally it leans towards yes. It just kind of depends on like, interestingly, like with Maurice, it didn’t, Doctors, it didn’t really have any, a lot of context. It just had like the kickoff call reporting questions, I feel like it did a really good job for that. Whereas this one with Draper, it should have way more data. And it just pissed me off. It wasn’t doing it very well. But sometimes it seems like with less information, it can do an even better job, which I thought was interesting. Ben Ornstein: That’s interesting. Yeah, I’m trying to think what I seeded Maurice’s thing with. It was definitely the kick. For every new client, I’m doing the kick. I’m doing the intake form. And then if they have posts, I’m putting posts in. Jacob Shipley: Yeah, it’s been doing a great job for him. That’s good. UNKNOWN_SPEAKER: Yeah. Ben Ornstein: His bar might also be lower just cause like he’s not a content guy or like he hasn’t written much content. So that could be a factor as well. Like he’s just approving them just cause like he doesn’t. Right. Jacob Shipley: I don’t know. That does make a huge difference to like James Draper has been very, very specific. Like his voice is so unique and so different that it’s like very. It’s so infused with his personality that’s like, We can write how you would write, but even like with the onboarding call. He would say things and I would put word for word a phrase he said. And he said, I wouldn’t write this way. I was like, well, that’s difficult because I see what you said. And he said, I know I said it, but I would never say it in a post. I was like, well, I have no way to know what you say on a call with me versus what you would say on a post. I’m not a mind reader. I want to get better. And also, he makes jokes. I’ll make a joke. He’s like, I wouldn’t make that joke. But then he’ll make a joke about, what did he say? Um, he said, I didn’t get into venture capital to wear the makeup, but it’s a nice perk. I was like, well, I would never write that for you. I don’t want to like risk, like, you know what I mean? But like, I would say, and there was one time too, I said, like, I wrote a hook that I thought was very funny. And he said, great hook. I love it. And then he changed his mind and said, actually, I don’t want to have like hooky hooks. Okay. Well, like, that’s fair. Like you can change your mind, but anyway, like that’s not a scenario where Casper is doing wonderful job because even me as a person that has had multiple conversations with them, I’m really struggling to figure out like what do you actually want. So you’re right like with Maurice like he just wants to get posting and so the the bar is lower and so that’s a very good use case. I think he’s been doing a good job with Tim like but Tim also generally unless you say something that really irks him he generally just approves So that one’s fine. I’d say, I don’t want to say there are, there’s no such thing as a bad client, but there are easier clients and easier clients, Casper’s, it gets an 80% of the way draft there that I can get up to par and then push it out. One thing I’ve wondered about is like, cause I, like I said, I’ve used Claude a ton for getting like drafts ready and sometimes, before Casper, and sometimes it gets it very, very close. Sometimes it’s not, and so I have to edit it a lot. But I’ve wondered, too, of the stuff Casper’s writing and stuff Claude’s writing, if they were to copy and paste it and put it in an AI detector, would it set off alarms, like this was AI written, and do we care about that? And that’s one thing I thought about, too. Michael Houck: So we’ve tested that. We put it through, I put it through Grok a bunch, but I’m sure you put it through Claude, too. I don’t know that, but I put it through Grok bunch and most of the time it comes out as like this is highly likely to have been written by a human. Obviously there’s some like sometimes where it does the formats, Jacob, like you’re and it catches that in those cases but you know that’s also I think part of Eddie’s job too. So it makes sense that it would pass in most cases like an additional check level. Ben Ornstein: Eddie is supposed to humanize recognize any draft that Casper sets. That’s like a huge part of his like exact job. And he still misses it sometimes. And I can’t, I can’t figure out why sometimes he does and sometimes he doesn’t. Michael Houck: Jacob, you said that Casper gets 80% of the way there, like, you know, some percentage of the time, right? Michael Houck: What is the Like, how would you articulate I don’t know how I would articulate it. Jacob Shipley: I don’t know if it’s a formatting thing or a stylistic thing. Tone thing, but it’s just like, I guess it varies. Sometimes it is one of those formulas of it’s not this, it’s that. Sometimes it’s that. Sometimes it’s, I do like a line break here to make it a little more punchy. Sometimes it’s, I’ve had a conversation with a client before and they told me this story that I remember and I want to put a line in about that. Sometimes it’s, I thought of a better hook in my head of be more intriguing to start with this line. So it’s not like it gets the same thing wrong. It’s not even getting anything wrong. It’s just that I have an idea or I have context from writing every day on LinkedIn. I just feel, I don’t want to say it’s vibes, but it’s like, there’s like, I know I can make it 10% better if I give it a pass over You know what I mean? Like, there’s just like, it’s not the same thing every time it’s there’s something almost every time there’s at least one thing I would personally do a little bit different. Sometimes it’s 10 things I do different. Sometimes it’s zero. But usually there’s like one or two things I’m like, I just want to tweak that a little bit. And how that makes me being anal about it. I don’t know. Michael Houck: No, I think it’s unlikely that it gets percent, like being able to do that without any level of human check. But I think that’s fine, right? Because if it’s also speeding up how quickly we can get stuff done, it’s going to allow us to do more, right? Either higher volume of posts for the same number of clients, or, or just more clients without having to, you know, go out and build a more complex team structure or something like that. I think there’s benefits to but I have another question. How has it changed your workflow so far? And like, how do you like interacting with it? Jacob Shipley: Yes, I like interacting with it. I don’t, I guess one thing I’m unfamiliar with is if I have a conversation with it about a client, does it remember all of that? Ben Ornstein: Yeah. Yeah. It’s, it’s actively adding things to like its own memory. So I’ve made that very, where it’s like, it should remember things from one session to the next. Maybe not like the exact details, but it will, it is configuring knowledge about the client. So in general, I would say yes, but it’s not gonna get it perfect. Jacob Shipley: If you think about it. Jacob Shipley: Yeah, generally, I like working with it. Let’s see. Yeah, I don’t, I mean, it’s changed the workflow of like, instead of going to cloud I’ll put the draft, I’ll just go to the channel and I’ll say, you know, draft a post about this. The only thing that I haven’t done that I’d be curious to see how it did is like one thing is like, how can you record a call with Tim? I’ll take the transcript and I’ll put it in Claude. And I’ll say, give me as many post ideas as you can about this. And then I’ll like kind of batch, go work through that. Okay, like flesh that out. And then I’ll kind of edit that one, flesh that out. I’ll edit that one. I haven’t done that with Casper yet. So I think that’s the only like use case I haven’t tried is like, I’ve used it a bunch for write this post. I haven’t said, here’s a transcript, write seven posts I post about this, this, and this. So I’d be curious how it holds up with that. Ben Ornstein: He’s pretty good with that when you give him transcripts and just learning from it in terms of like building out the voice bibles and stuff like that. I would imagine it would be good. So yeah, if you give him like a TXT file or an RTF file, that should work. I’d be curious to hear what the output of that is. Okay. But it should work in general, like, he should be able to create posts from that. No problem. Jacob Shipley: And I could have them do like, come up, come up with post ideas based on this transcript, and then one by one and go through. Ben Ornstein: It’s, it’s like what they say with any like prompt into an LLM, like the more context you give, the better output you’re going to get. Yes, they’re trained on clients, they’re trained on the best way to create posts, but yeah. Michael Houck: I just want to move as far as we only have a couple minutes left. Jacob, I noticed that, you know, it was interesting to me to see you tell Casper that you wanted to review the post before it was sent to Eddie rather than after Eddie, but pre-Blake. Why did you prefer that? Jacob Shipley: I guess I wanted to make sure I liked the direction of it because there were some times where it was like, I want to really see it directionally. Is it correct before we, because it was doing this thing where it would just send to Eddie and send to Blake. I’ve never even seen anything. And I was, I know like we change it to where it goes to backlog instead of internal review. But there were a couple of times where it was showing up in Blake’s like get notifying Blake before I even saw where it was directionally heading. And so I was just trying to get as early as possible. Can I just see like, you know, if I was talking talking to you, I’d be like, what are you thinking about for a post? And just make sure like, is that the right, is it directionally correct before it just, I was just trying to stop it as early as possible just to make sure it was, I guess like technically if it wants to go to Eddie first, maybe it was just a patience thing of like, I don’t know how long it takes for Eddie to review. And I’m just like, I just want to see something right now to see where it’s going. That was kind of my thought process. Michael Houck: Do you have a preference between like, again, in a couple of scenarios. Scenario one, you give a prompt to Casper. Casper responds with a couple angles for the post. You pick one out and then it sends it to Eddie and writes it and sends it to Eddie for review, right? Number two is you send the prompt. You still get to review the angles and pick the angle, but you get to review the draft of the post that Casper writes before it gets sent to Eddie. In both of these scenarios, assume you can see it after Eddie as well, but do you want that extra step of reviewing the post before it gets sent to Eddie for review? Jacob Shipley: Not necessarily. I think if it, I like the idea of it giving me directions of like, do you want me to do this angle or this angle or that angle? And I say like, do a combination of angles one and three, like that would be interesting. I’d like that. But it’s almost like, I don’t, I don’t care if, it’s almost like it just annoying to me to be like, I’m going to send to Eddie now. It’s like, you’re not a real person. You know, like just, I just want to see a post. You know what I mean? Like, just let me see if you want to send it to Eddie and get humanized first. Great. And then let me see it. But it’s like, I just was like, it felt like a needless extra step. That was like, I want to see something when in reality it’s like, yeah, I don’t care if I want to send it to Eddie first and then get humanized and then show me a draft. Perfect. That’s, that’s great. I just like, Yeah. It just felt like, it’s almost like the writer doesn’t need to know whether it’s with Casper or Eddie. Cause it’s like, it’s all just, you know, just let me see it when it, when it’s ready for internal review or ready for the backlog, let me know. And then I can look at it. UNKNOWN_SPEAKER: Okay. Yeah. Jacob Shipley: Ben, I think that in, in Slack, because it was like, I don’t want it to be like, cause it would for a while there, it was being like, send it to Eddie and then we’ll go to internal review and then it showed up in Slack. And so then I had, or in, so then I had to go over to Notion to review it. It’s like, just show me the draft in Slack, and then I can say, actually do this, do this, do this, and then send to Eddie, or then send the backlog or internal review or whatever, so that I’m not having to jump back and forth between Slack and Notion. Ben Ornstein: Yeah. Part of these processes were like things I’d built in originally, and they had been changed, but only parts of it had changed. This makes total sense. I can change it. So it’s angles, first so you can confirm the angle, and then it doesn’t really matter from there. There’s a lot of confusion here, but I’m not going to. Michael Houck: It’s funny that we’re landing on this, because if you go through, so I have a thread with them where I’ve had them write a couple YouTube scripts for me. And I do this. I ask them, hey, before you write a whole YouTube script, give me a couple angles for this video. Because I don’t have YouTube, right? So it’s funny that the same thing is sort of playing out here. It does sound like a best practice. So, okay. I have one more, Ben, do you have any that are like, you want to get across to? Ben Ornstein: I’m good. Michael Houck: Okay. So Jacob, we were also, I guess, let me phrase the question in like a user researchy way. How much time do you spend sourcing topics for clients right now? And do you think that an AI system, like not Casper or Eddie, but like someone else, another agent could take that job on effectively for you? Jacob Shipley: Yeah, I’d say the number one thing is when I have a call with a client, I’ll feed that transcript and I’ll say, generate posts based on this. And then I’ll, my followup is always, are there any angles you didn’t cover? And then if they say there’s three, then I’ll say, okay, now turn those into posts just to make sure I milk that for all. Cause it never seemed to get them in the first pass, all of them. So I milk that. Then like with Draper, they stuff will pop up in the press channel. And so I’ll do that. Sometimes I’ll just Google the client’s name and see like, has there been anything interesting that’s popped up lately or the company? Or I’ll just say like, you know, I’ll depends on the client. Like with Noel, I would be like, send me a photo from your camera roll. Like what’s something you’ve this, that you’ve taken a picture of lately. And I’ll write a post on that. So that, yeah, that definitely is like, there aren’t any clients right now where it’s like, I don’t know what I’m going to write about. Maybe Will from Flash Pass is like, we’re getting to the point where like, I need to hop on another call with him now because I’m out of, you know, we’re essentially out. And so I need to write something there. So I don’t know if there’s a way to automate. There’s a way to automate parts of it. But essentially, like at some point, you get to a point where it’s like, everything we’ve ever talked were kind of milked. And so unless I start like repeating ideas, it’s probably good to hop on another call, which I know, I guess it’s interesting, because there’s really there’s two angles. Michael Houck: One is sort of what you’re getting at here, which is like the personal stories, the unique details about this person’s journey that we can make the content sound like them, right. But then there’s also the other angle, which is like, you know, you can’t spend your whole day scouring social media for like every trending topic in the Ohio politics niche for Will, right? But an AI could. Would that be doable? Jacob Shipley: Just a list of bullet points of like, phrase it as give me three questions to send to Will for him to record a voice memo on. So it’s like this, I don’t know, Vivek Ramaswamy is doing XYZ, what are your thoughts on this? Or Elon Musk said this about AI and workforce development, what do you think about it? So like, yeah, if it could give me questions to ask Will, because we would still need Will’s unique take on it, that I wouldn’t want to just take like Elon Musk said this, now respond as Will. I would probably, I mean, we could do that actually. And that’s essentially what I do. I’ll ask Will a question, Will won’t answer, and then I’ll write it and give my best guess at what he would say. So that’s probably like what I would have AI do, say like, okay, give me three questions. I ask Will, Will does an answer, and then I say, okay, using your best judgment, respond as Will, and write a post on that. So yeah, I like that idea. Michael Houck: Cool. Okay, that’s coming very soon then. So we’ll take that into account. That’s all I have. Ben, do you have anything else we should go through? Ben Ornstein: Yeah, no, that was the last thing I was gonna bring up, that kind of workflow and what would be helpful there. So, no, this has been awesome. I’m definitely gonna apply specifically the angles one, like that part of the process, because that makes complete sense. You should be able to choose. So let me build that in. Jacob Shipley: Cool. And then, Ben, are you going to join the call with me and James. Ben Ornstein: So I have a call with HALC right now. Ben Ornstein: We’re going to discuss. Michael Houck: And we can we can do that another time. Ben Ornstein: That’s that’s That’s So we could do like half an hour. Michael Houck: Okay, let’s do half an hour. Ben Ornstein: Okay, then I’ll, I’ll be there, Jacob. Okay, cool. Michael Houck: Okay. See you guys. Thanks, Jacob. UNKNOWN_SPEAKER: See ya.