Writing Whale Bait Live with Ai (38 minutes)

In this 38‑minute live workshop, host JK demonstrates the AI writing assistant "WhaleBait Kashi" (also referred to as Cachey) and uses it to generate marketing copy for various coaching offers. The session centers on Brandon’s high‑ticket one‑on‑one coaching service aimed at affluent men (ages 40‑60) who are transitioning from a career‑focused "war" phase to a post‑war identity crisis. Brandon describes his clients as "wearing armor in peacetime" and needing an "anchor" rather than mere accountability. JK shows how Kashi can ingest client data, remember context, and instantly produce newsletters, subject lines, social posts, and offer copy that reflects this "armor" metaphor. Technical hiccups (API‑key mix‑up) are resolved, and participants experiment with prompts for different audiences, including a gym‑friend story (Speaker C) and a mindset‑first coaching narrative (Speaker D). Throughout, the group iterates on tone, angle, and calls‑to‑action, illustrating how the AI can shift from generic templates to highly personalized, identity‑focused messaging. The workshop ends with concrete copy drafts, quick‑action prompts, and a discussion of how the tool can serve both niche (high‑net‑worth) and broader markets.
Chapters
A few weeks ago, I ran kind of this private thing where I released Whalebait Kashi. And Whalebait Kashi is basically virtual me, but rides Whalebait for people. And this is a video of her doing the thing. So enjoy.
Okay, JK, I'll go.
Let's go. So let's roll. What happened this week, month, or year that we're talking about, and what are you working on right now?
I have a couple different projects going on at the same time.
Okay.
And I'm going to be launching a, a rebrand of my one-on-one coaching service, going for high-dollar value people. It's interesting because even without trying, I'm starting to get some of those clients already, so I'm doing something right. But I'll be honest with you, I don't know what it is. So that being said, a lot of the basis of my one-on-one coaching is around the idea of reinvention, right? And so Because of the messaging that I use, it tends to be— the demographic tends to be men 40 to 60, tends to be the demographic. High dollar value, busy. I mean, I have a couple clients where I'll actually go 1 month, 2 months, almost 3 months without hearing from them, even though I'll check in, even though I'll ping them and say, hey, how are you? Busy to the point where I'm almost on call, right? But not very often. And I find that interesting. So, um, I want to get more specific about what the messaging looks like. Like, what am I doing right? What am I doing wrong? And thank you, by the way. Nice to be on this call. I appreciate you.
Thank you for being here. So when those guys go silent for 1 to 3 months, did they come back apologizing or did they just pick up where they left off like it's business as usual?
Yeah, a little bit of both, to be honest. It depends on, uh, depends on the client. Everybody, uh, everybody usually apologizes upfront, but the conversations pick right back up where we left off. So there's a comfort, there's a familiarity, um, there's the relationship. It hasn't changed. At all.
What's the specific moment that drives them to you? Is it a crisis? Here she's getting specific. See, divorce, health, or just boredom?
Yeah, the, the core messaging of the website is, is that something has happened, right? Like, are you at the end of something big in your life That's the kind of the, the masthead of the, uh, of the pitch, right? Many times these endings mean that you can no longer be the person you were in the past. You are forced to reinvent yourself, to create a new you. But the process of personal reinvention is something that's eluded people for centuries. Where do you start? How do you pick up the pieces? What does progress look like? When we have the right process, the right guide, and the right accountability, swift reinvention is possible. And that's like the core masthead messaging of, uh, of that, right?
I'm just gonna send— I'm just gonna send what you sent me. So the sentence tells me they're looking for accountability, they're looking for an anchor. When you say end of something big, is that usually a victory lap? So the company retired, or a loss? The worst empty nest.
Yeah, it's almost always a lost chick.
You're acting less like a coach and more like an architect. They need a cheerleader, they need blueprints. That's why the silence is fine, because they're off building. They come back when they need the next set of plans. When they start picking pieces for this new identity, what are they actually picking? Are we talking habits, wardrobes, beliefs, or something bigger?
Yeah, it's, it's almost always habits. And a lot of it has to do with mindset and beliefs. Hanging on to, hang on to, to mindsets from their old lives or from their past lives that aren't appropriate anymore.
I made a typo, but Cachey understands. Okay, while she thinks, you can see all your assets here. This is new. So you— Clash Royale newsletter. I wrote a newsletter on Clash Royale. Great game, by the way. So you can see all the things you've created here, and you can just export it like that. And when you go to offer Cachey, if you click on the same thing, it's going to show you all the offers that you've printed. Some interesting thing that you can do is if you go to settings— actually, we'll do that after. The habits they're holding on to aren't just bad habits, they're survival mechanisms from a war that is already over. They're wearing armor in peacetime. They don't need you to tell them to drink water. They need you to tell them it's okay to take the armor off so they can actually move on. About right?
Yeah, that's right about 50% of the time. It's right about 50% of the time. You know, um, I have found that with a lot of the clients that show up on my doorstep that, um, the storm is over for them. They just don't know what's next. They don't know how to begin that reinvention process. Right. And so it's, it's interesting.
Cool. Back where we left off. I'm gonna, I'm gonna go back to this. But memory is here. So right now, she knows everything about me. So it takes shorter for me than it takes for you. This will not happen to you like in a week because she'll know. So something interesting that you can do is go to any AI thing you currently use. Be it OpenAI, Claude, Gemini, whatever, and ask it, give me a list of everything you know about me and my business. And then it'll spit out a bunch of items and then copy this here. So for example, JK launched WhaleBait Hashi on December 22nd and is printing WhaleBait live, right? So I can add it and then it's stored. So for example, next time I tell her, let's make an offer about whale bait cashy, she won't say, what the fuck is that? She'll say, oh, same thing. Do you have that transcript from the other day that maybe we can use today? That kind of thing. So your clients aren't suffering from failure. They're suffering from the vacuum that comes after the war ends. They spent 40 years optimizing for the fight. Now that the fight is gone and they're standing there in full armor with no enemy to kill. They need a coach to tell them to hustle. They need an architect to help them build a life where they don't have to fight anymore. About right?
Yeah, yeah, yeah, that's it.
That's it. So guys, I found where the mistake was. Brandon, it's because I just I just went over my data. I just, I just used a different API key, literally just copy and pasting something else, and that was it. You, because your key is new, this won't happen to you. I've just been abusing this too much because I've been testing a lot.
So are you saying, JK, that, that we're gonna, that we won't, we won't run into that problem? That is, this was just for you because you've been grinding on it?
Yeah, I've sent maybe 500 messages in the last 2 days. Okay. Okay.
All right. Yeah, that explains it.
Yeah, it's because she wasn't doing one thing that I really wanted her to do, man. But now it's over. Now she can do it.
So, okay.
So let me, let me ask a question while I got you here. Um, I have a, a group cohort. I have a cohort starting in mid-February. Um, I hadn't really thought about the idea of, uh, kind of turning it into whale bait. It's more for a general population, right? Um, will Cashy kind of help me narrow it down, or is it all going to be skewed towards high-value individuals?
You can— it's a, it's a different thing. So I need to explain what she'll do. It's the option is A. She won't do it only for high-value individuals unless you ask for it. She can do both, but she'll give you by default A, because it is my belief that we shouldn't filter through this is for this people or this for that people are at this level. I think we should think of ourselves more as we just create assets and tools. So when I promoted Whalebit Cashy, I didn't say this is for the coach or consultant who has clients and posts on social media, right? Because what if there's an agency owner? What if somebody wants to do it as a ghostwriter? Like, it wouldn't apply, but they would still get value from it. So Cashy is designed to not show your stuff as this is who it's for. But just this is what it does. An example of this is let's say you have your phone and it's running out of battery. What is the first thing you think about? You don't think I need somebody who can lend me a charger, but they need to be for coaches who help people find their way after this and high value. Like you don't think about that. You just need, you just think I need a charger. I need something. So Cashly is designed to just show what the tool does, and then the market finds itself. That's why you say you don't choose your niche, the niche chooses you depending on the tools that you create.
Thanks, that helps.
Yeah. So let's read it. Armor in peacetime. I have a strange relationship with my best clients. They're men between 40 and 60, successful, high net worth, and they ghost me. Sometimes for a month, sometimes for 3, then they pop back up. Sorry, I went dark, I was handling X. And we pick up exactly where we left off. At first, I thought it was a flaw in my retention. Then I realized it was just a feature of their character. These men aren't looking for a cheerleader, they don't need accountability, they need an anchor. They spent the last 30 years fighting a war. And if you know anything about men, they like it when you say that they've been locked in in the trenches in a war. Building the company, securing the state, raising the family. They've optimized every habit, belief, and every waking hour for survival and conquest. But now the war is over. The company's sold, the kids are gone, the marriage ended or shifted, and the noise just stopped. And they're suffering from the vacuum. They're standing in the middle of a peaceful field wearing 100 pounds of armor. The habits that saved them during the war are the same habits suffocating them in the peace. They try to reinvent themselves by adding more, more discipline, grinding, more doing, but you can't build a new life when you're defending the old one. My work isn't about adding new habits. It's about identifying which pieces of the armor they can finally take off. It's architectural. We look at the empty lot where the war used to be and ask, what do we want to build here? The silence isn't disinterest, it's construction. They go away to build what we discuss. They come back when they need the next set of blueprints. It's a specific way of working and requires high trust and low maintenance. And I'm opening a few spots for this specific type of reinvention work. If you're standing in the quiet and don't know what to do with your hands anymore, reply armor and I'll send the details.
Oh man. Oh, that would have taken me a week to come up with, bro.
See, I told you, when she works, she works, man. But the fucking API key wasn't working. But now—
oh my God, yeah, I'm so glad I signed up, man. I signed up a couple hours ago. I was like, I can't not do this. Like, I just, I just hired a publicist and I'm doing a couple different rebrands and I'm like, dude, this is like having JK in my pocket. Yeah, it's brilliant, man. Thanks, thanks for the— thanks for taking this. And where do I find that, bro? How do I cut and paste that? It's so hot.
I, I can send it to you. I don't know. I'll send it on the chat so you can have it.
Thanks, man. I appreciate you taking the time this morning.
Yeah, no problem. I'm happy she can, she can serve you like that. All right. Well, that's a little bit casual, folks. What happened this week, month, or year that's worth talking about? Or what are you working on right now? And what offer are you looking to promote at the end?
So I go to the gym every day around the same time, 2 PM, and I always saw this guy and we would kind of like nod at each other, but we wouldn't talk. And about 3 days ago, I thought, why not just talk to him? So I went up to him and was like, what are you training? And then 3 days later, so yesterday, Sunday, we trained legs and we were in the gym for just 4 hours just talking and pushing each other. And we both ended up hitting a PR on the squat.
Cool. What are we promoting?
The offer is one-to-one coaching for identity transformation.
Okay, we're going for another intangible one. Let's see what happens. So the score didn't change because of a new technique. It changed because you were no longer the only person in the room holding this standard. Does that sound about right?
Yes. I would also say the main thing that led to the growth was having the confidence to talk to someone new and making that connection. And then that led to increase in strength in the lift as well as a new friend.
The weight didn't get lighter, just became the person who asks for more. The connection was the catalyst, but the confidence was the cause. Is that about right? When you're working on identity transformation, is the goal to make this shift feel like accident or a deliberate choice?
An accident almost, because you become the type of person who is social and wants to meet new people. And then naturally you have opportunities that come from that, whether that's financial opportunities or just friendships or romantic interests.
She's not designed to follow, um, uh, a template. Like, I literally told her no templates, we don't do that shit. She's designed to follow energy. So wherever you're going, she like kind of reflects it. If you're being a dick to her, she'll be a dick to you back. If you're being kind, then she'll be like, what can we do? The accident is leadership without the ego. You change the identity, so the world changes the outcomes it allowed. Before you spoke to them, what was the story you told yourself to justify the silence?
Typically, back in the day, it would probably be, he's too busy, I don't want to distract him. People only come to the gym to train, which is also a belief that I've shifted in my mind.
The too busy story was a fence. It protected the ego from the unknown. The PR wasn't a gym win, it was a result of removing the labels that kept your world quiet. Does that sound about right?
100%. Yeah, bro, this is so crazy. It's almost like you're writing it for me and I get to learn off of that, the knowledge that you have.
That was a goal. Well, I'm happy, I'm happy she leaves that impression on you. So let's see, let's see. It only works if it works. So it sounds like you've moved from being a spectator in your own life to being the protagonist. The squat bar didn't get lighter, your willingness to carry it changed because you were no longer in the room by yourself. And then it's like, yes, I nodded to the same, uh, the squat PR accident. I nodded to the same guy at the gym for months. We shared the same 2 PM slot. Both of us were in our own heads. I told myself he was busy to talk, told myself I wouldn't— I shouldn't distract him because only people come to— because people only come to the gym to train. 3 days ago, I broke the silence. We were 4 hours deep into a leg session and we both hit a PR in the squat. The strength didn't come from a new program or a better supplement. It came from a shift in identity. When I stopped being the guy who protects his ego with silence, I became the guy who asks for more. I stopped looking for reasons to stay quiet and started looking for ways to connect. Identity transformation makes these opportunities look like accidents. It turns a nod into a new friend and 50 pounds on your bar. You become the type of person who is social and meeting people leads to friendships, business, or romance naturally. I'm working with one-on-one clients to shift the labels that keep their world small. We don't do check-ins or accountability. We do identity shifts. People buy coaches, not coaching. I help people lead themselves so the world can follow. If the timing works, reply identity and I'll send the details of how we can work together.
Yeah, made the intangible tangible.
Yeah, yeah, you want to do that with a lot of intangible things. For example, you want to shift, right? So for example, This is why she asked you what else can happen from this. Because if we are just like identity, like you get it, your clients get it. But the thing is you need somebody else on a different angle of the picture to get it.
Yeah, they don't desire an identity change, they desire the result of that.
Yeah, or at least not yet. They need to work with you in order to get it. So that's a newsletter which sells an offer. This is what sells the idea. Weight on the bar is often a reflection of the weight in your head. Facts, bro. Nobody talks about this. I watched the guy at the gym for months without saying a word, told myself he didn't want to get distracted. But the truth is that they didn't want to be rejected. And I broke that label 3 days ago. Today we hit squat PRs together after a 4-hour session. The accident of hitting a new record was the result of a deliberate identity shift. Opportunities in business and romance follow the same logic. When you become a person who connects, the world starts offering you things you didn't even ask for. You don't need a better social strategy, you need to be a bigger person. Again, it's you don't need me, You could use me. Strength is a side effect of who you are. So, tweets and stories. The squat PR was a side effect of breaking the silence that had lasted a month. Stories like this person is too busy are just tall fences for a quiet ego that wants to stay safe. Identity transformation isn't about learning a trick. It's about deciding the silent version of you is no longer in charge. And those are like little mic drops you drop into stories, right? It's like with a nature picture in the background, your coffee, and so we'll put that in.
This is fire.
And there's some plugs. So quick actions. What do you want to do?
Um, that seems perfect, to be honest. I mean, we could try a different angle, I guess.
For the sake of a different angle. Let's, let's, let's be a little mean to her.
Yeah.
What about the angle isn't landing? So come up with something. Too abrasive, too cringe, too broad, too broad. The not is a low-status placeholder for a conversation. Do you want to focus on the months of wasted potential in that silence, or the specific moment the 4-hour session became your new normal? Which part of the story feels like the most like the work you do with clients?
I'd like to dig into the pain of, I suppose, being lonely and not and never going outside of your own shell and outside of your comfort zone and never starting new conversations.
There you go. Now you're talking. Now you're talking, um, specifics. Like, it's hard to say mindset angle. It's, it's hard to say you have an identity— not crisis, but trough. But you could say you're not starting new conversations. How many strangers did you talk to in the last 30 days, and then it's black and white. The nod isn't a greeting, it's a compromise. You're trading the possibility of a 4-hour breakthrough for the safety of a quiet, predictable session. So here's a different angle. Let's say you didn't like the original. Here's something new. I shared a gym floor and a nod with the same guy for months. I like that. We're both there at 2 PM every day. I stayed behind a fence of my own making, told myself he was too busy and I shouldn't distract him. The truth is that the silence is a tax. I was paying it every day in the form of a stand-in workout and a predictable life. Safety feels good in the moment, but it is a slow poison for the soul. 3 days ago, I refused to pay the tax. I started a conversation, and 4— and 3 days later, we were 4 hours deep into a leg session. We both hit a PR. The strength didn't come from a new program. It came from the space I created when I stopped hiding in my comfort zone. Loneliness isn't just a lack of people. It is the weight of the conversations you never start. Identity transformation makes these shifts look like accidents, turns a polite nod into a new friend and a record lift. When you become the type of person who is social, the world starts offering you opportunities naturally. I'm working one-on-one with clients to remove the labels that keep their lives quiet. We don't do check-ins, we do identity shifts. If the timing works, reply identity, and I'll send you the Google Doc that, by the way, Cassie can also make. Boom. And you send it.
Makes me want to buy my own stuff for sure.
Well, this is just an example. Thank you, man.
No worries. Thank you.
All right, who wants to go again?
I want to go.
Let's go. Um, all right, let's start. So let's go with you. What happened this week, month, or year that's worth talking about? What are you working on right now?
Well, so I stood up to my boss when he tried to intimidate me and tell me that I did things wrong. But I said to him that it's not my actions that triggered him, but his own mindset. No. Okay, that's a difficult process to fire me. So, um, like 2 years ago, I couldn't do that. I would be offended. Some more years ago, I would probably cry. Um, but now I'm firm in my beliefs that I did everything right, even though his boss was not that pleasant with the thing I did.
So what are we promoting at the end of this, and what's a short description of it?
Say again?
What's this? What are we looking to promote today? What's your offer?
Uh, the offer is, uh, Mindset First. Well, it's like coaching with the people who are stuck in their development, um, probably because of their self-perception.
So I just, I try to give, I try to give Kashi everything you told me without changing much.
I've been talking to Kashi for a day now. It's like having a couch.
It's what?
It's like having a couch.
Oh, cool. So standing up to a boss is high-stakes demonstration of sovereignty. 2 years ago you would have cried, now you're the one diagnosing his triggers. What was the specific phrase he used to try to intimidate you, and how did your internal reaction differ from the old version of yourself?
Let me remember. He told me, he asked me, why didn't you inform me of your actions? Why did you skip me and file this document on your own? My old version of myself would would have asked for permission to do that.
Look at the face.
He would hesitate a lot. But now I feel powerful in my beliefs, and how do I say that, I have confidence.
All right, this is going to be a good trial. I'm curious on what catch is going to give her because this is not as objective as, for example, a fitness guy is, which is like get a six-pack, or money guys are, which is make money, right? This is different. So let's see. So the moment you stop asking for permission is the moment you become a threat to somebody else's fragile sense of order. Your boss wasn't reacting to the dog, he was reacting to the fact that you no longer need him to tell you you're right. Does that sound about right?
Sure.
Okay. Ready for me to write? If so, one line or two breaks? She asks this. Frankly, I just did this for myself because if for some reason if I do two breaks in my own email provider, which is ConvertKit, it just completely messes it up. So I just did this for myself. But usually if you want like two enters, You press 2.
I actually do like to enter.
Yeah. All right. Let's see what she gave you. This is new, by the way, and you can see that it's impossible for me to have planned this for better or worse because the fucking app crashed in my demo, but we can keep going. So newsletter version subject line, the document incident. "Why'd you skip me?" My boss was looming and the air was thick with the usual intimidation. He wanted to know why I filed the document on my own. 2 years ago, I would have apologized. I might have hesitated and looked for a green light. Might have even cried. But I've stopped being a permission seeker. I realized that my previous version needed someone else to tell me my work was valid. This time was different because I didn't inform him. I didn't need to. The document was filed and the work was finished. His anger wasn't about my actions. It was a reflection of my own mindset. He realized his sense of order was built on my willingness to be small. When the hesitation left, his power went with it. I lead myself now. Even his boss isn't pleased with the shift. This is a mindset-first existence. If you find yourself stuck in your development, it is rarely a lack of skill. It is a self-perception issue. I help people shift that perception to regain their momentum. If you're ready to stop asking for permission, reply mindset and we'll talk private.
Nice.
What do you think?
It's powerful. You know, there is a word. I forgot the word. It resonates. On a deeper level.
I'm glad.
It's like I'm really talking to myself through my writing.
Happy to hear that. A few things that Will Bake Hashi did, because the prompt is actually, we measured it, 31,252 characters. So there's a lot of things that, it was hard to create Will Bake Hashi in the sense that, you know how, for example, if you're a runner, you can tell when something feels off. but explaining it is hard. Uh, that was what was hard about WillBeCashy because I had to explain everything that I think through things and why is it wrong or why is it right? So there's an example here of this, this, if you find yourself stuck in your development, it's rarely a lack of skill. It's a self-perception issue. So what is this? WillBeCashy is programmed to never tell your prospects that they're wrong. They should never tell them that they are missing you or that the only reason why they failed is because they don't have you. Why? Because of course you're going to say that. Of course I'm going to tell people if you're not making the money you should be making, it's because you're not working with me. And that's, that's pushing. That's not elegant persuasion. That's lazy. A better way to frame whatever service you're doing is telling them, you're probably doing the right things, you're probably 90% there, but consider doing this other 10% because that is what worked for me. And you end it there. What happens then? It's no longer, of course you're saying that, Mike, you dick. But now it's like, it's an invitation. Like, you already have something going on, let's put something at the end of it. So that's just one of the things that's happening now. We're gonna work through a few later. Here's a post version. So it's gonna give you a newsletter first because I believe emails, um, is the best. Post then comes after. Now the post is designed not to sell your offer because if you keep promoting on socials, you will get really old. The post is designed to sell people on an idea. Because if they buy into your ideas, in my case, it'd be like the offer show, Whale Bank, Value vs. Insight, likes and cash, then the likelihood that they join the newsletter and buy is much more likely. So post version: intimidation only works if you agree to be small. My boss asked why I didn't inform him of my actions. He wanted to know why I filed a doc on my own. I didn't answer with an excuse, but I just told him the truth. His reaction was a reflection of his mindset, not my actions. 2 years ago, I was a different person. I was looking for a safety net in his approval. Now I am the leader of my own work. Confidence isn't about knowing you're right. It's about not needing anyone else to confirm it before you move. So we're not selling an offer. It's just, this is my idea. This is who I am. This is what I believe in, which makes you more persuasive when you actually make an offer. So that's why there's two things. There's a newsletter and there's a post. Right after that, it gives you 5 or so tweets or stories. So these are things you can put as individual. You can put it in the story because, you know, you can spam stories and people don't care. Sovereignty is terrifying to people used to being asked for permission. If your growth is stalled, check who you are still asking for a green light.
I like that one.
Intimidation is just a mindset problem projected into a person who won't flinch. The difference between a permission seeker and a leader is one difficult conversation. So at the end, it's going to give you also email plugs. I recommend you post one of these a day under a tweet or as a standalone story. What happens when you stop being nice and start being assertive? The right people start to respect you. And then it's not picking up now because we're not on the main cache, but it's going to ask you something like, I share insights like this inside of my newsletter, which you can join. It's one free, leave anytime. And it's going to give you a link. Eventually she's going to remember what the link is, so you can just copy and paste it straight from here. So, Mike, last question, quick actions. Do you want a different angle? Does it not sound like you? Did they not pick some details right? Something feels off, but you can't put your finger on it, or are we done?
I'd say we're done.
And we're done. So yeah, that was one example of what, uh, Cachey can do. Uh, Welby Cachey can do. She sends you a heart. Anybody else want to go?










