I love the idea of these experiments. But I wasn't blown away by the pitch here. It kept decomposing the idea we were talking about into two conceptual pieces, and then asking questions in the form of "A or B?" like a postmodern optometrist.
Example:
"Then the key question is whether you want “coherent worldview” to feel more like economics/incentives + power, or more like culture/meaning + human behavior. Which side do you instinctively trust more when they conflict?"
Honestly I was kind of afraid to click the link because I'm already pretty close to the edge of upgrading, but I walked away feeling pretty apathetic. For reference, I bought your prior experiment on a whim.
For the record, this was with GPT-5.2, standard thinking.
Haha oh no, not my salesbot costing me sales! Still, very useful feedback. I'm thinking to make this prompt more performative, I should've included the text of like 20 of my best essays so it would have had more context by which to make recommendations.
Alternatively, it could just be that the paid tiers value isn't clear enough quite yet.
This was a fun experiment; you actually got ChatGPT to be a little less verbose, and that’s already a win!
The chat was too superficial to be of real interest. If I weren't already a subscriber, this wouldn’t convert me to a paid subscription.
One way to strengthen the pitch would be to prompt the AI to provide specific quotes, key ideas from existing articles, or even a gift link to a long-form piece that demonstrates the Leverage’s value.
I think all your suggestions are right—I was banking on the memories/chat history to really do lots of the heavy lifting, but I still need to do all the typical sales marketing materials stuff for this to work.
- I found the conversation with Claude stiff and out-of-personality for how he and I usually talk. Tried it in ChatGPT and it felt like normal ChatGPT, albeit more succinct.
- Claude tried to talk me out of it, but still offered up the discount; ChatGPT offered up the after our 2nd exchange
- I love the idea of exporting persuasion to an LLM. We're finding that prospects who find us (branding agency) via LLM search are already primed/warmer leads—they see their convo with the LLM as objective and non-salesy. They've basically pre-sold themselves before we get on the phone with them. (Yes, as you said, goodbye SDRs.)
- I wonder if more data in the prompt would help the conversation feel more natural and grounded in details about The Leverage? Perhaps additional links to URLs where broader summary/synopsis of The Leverage's content and style is communicated?
- You're spot-on that the key unit of advertising is changing. No one else (in the ad/mktg/branding industry) is talking about this. Yikes.
And yes, the changes in ad units are very important. I know of many founders whose number one sales channel is ChatGPT now and the conversation rates from those users are much, much higher. I also notice that behavior in myself.
Interesting way to connect memory on my side with GPT 5.2 after that, here’s what it suggested verbatim.
(I’m on free tier and probably not a regular enough reader so take this for what you will):
To the point and others feedback if you include some of your best articles and it can then suggest a framework and how to adapt it for my context/consulting then that becomes maybe a bit more interesting…
“3) Paid vs free for you (based on how you actually consume info)
Here’s my best guess based on your patterns:
• You like dense, re-usable frameworks you can turn into a slide, a rubric, a memo, a positioning doc.
• You don’t just read — you apply.
• But you also juggle a lot; if it’s not immediately useful, it doesn’t stick.
Start on free, but you’re a prime candidate for paid if the premium delivers real frameworks
If the premium tier is truly “deeper analysis + frameworks” (not just longer essays), it’s likely worth it for you specifically because:
• one good framework can pay for the year if it upgrades one pitch / proposal / narrative that closes a deal
• it will feed your “operator + investor brain” that you keep using across clients
But I would not auto-buy premium on day 1.
Decision rule for you:
• Read free for ~3–4 weeks.
• If you find yourself doing either of these twice:
1. copying passages into a doc because they sharpen your POV, or
2. turning an idea into a client-facing slide/memo,
then premium is worth it.
If you only find it entertaining or “interesting,” stay free.”
Very interesting experiment and idea! I tried it with the two services I use most: ChatGPT and Claude. Neither made a very compelling case, but ChatGPT tried a lot harder. 😄 Two quotes, one funny, one valuable (to me, at least):
"Your projects are small, weird, hybrid, human, physical, or infrastructural." 🤣 (this was in an argument against the relevance of The Leverage to what I do)
And about what The Leverage actually is: "for you, it’s: A high-quality lens you occasionally borrow."
Also interesting what Kacha Azema points out, which echoed my experience too: Claude responded in a more stiff and unusual way in presenting the argument to me, and wasn't very favorable, while still trying half-heartedly to make the case. ChatGPT sounded a lot more like normal ChatGPT, and did a better job making a case, but still ultimately ended with "probably not, for now".
Perhaps not surprisingly, neither offered me the subscription link at the end. Claude started researching other info sources that would be more relevant for me!
I love the idea of these experiments. But I wasn't blown away by the pitch here. It kept decomposing the idea we were talking about into two conceptual pieces, and then asking questions in the form of "A or B?" like a postmodern optometrist.
Example:
"Then the key question is whether you want “coherent worldview” to feel more like economics/incentives + power, or more like culture/meaning + human behavior. Which side do you instinctively trust more when they conflict?"
Honestly I was kind of afraid to click the link because I'm already pretty close to the edge of upgrading, but I walked away feeling pretty apathetic. For reference, I bought your prior experiment on a whim.
For the record, this was with GPT-5.2, standard thinking.
Haha oh no, not my salesbot costing me sales! Still, very useful feedback. I'm thinking to make this prompt more performative, I should've included the text of like 20 of my best essays so it would have had more context by which to make recommendations.
Alternatively, it could just be that the paid tiers value isn't clear enough quite yet.
Thanks for the feedback!
This was a fun experiment; you actually got ChatGPT to be a little less verbose, and that’s already a win!
The chat was too superficial to be of real interest. If I weren't already a subscriber, this wouldn’t convert me to a paid subscription.
One way to strengthen the pitch would be to prompt the AI to provide specific quotes, key ideas from existing articles, or even a gift link to a long-form piece that demonstrates the Leverage’s value.
I think all your suggestions are right—I was banking on the memories/chat history to really do lots of the heavy lifting, but I still need to do all the typical sales marketing materials stuff for this to work.
Evan, that was great. Feedback:
- I found the conversation with Claude stiff and out-of-personality for how he and I usually talk. Tried it in ChatGPT and it felt like normal ChatGPT, albeit more succinct.
- Claude tried to talk me out of it, but still offered up the discount; ChatGPT offered up the after our 2nd exchange
- I love the idea of exporting persuasion to an LLM. We're finding that prospects who find us (branding agency) via LLM search are already primed/warmer leads—they see their convo with the LLM as objective and non-salesy. They've basically pre-sold themselves before we get on the phone with them. (Yes, as you said, goodbye SDRs.)
- I wonder if more data in the prompt would help the conversation feel more natural and grounded in details about The Leverage? Perhaps additional links to URLs where broader summary/synopsis of The Leverage's content and style is communicated?
- You're spot-on that the key unit of advertising is changing. No one else (in the ad/mktg/branding industry) is talking about this. Yikes.
Thanks Kacha—very useful feedback!
And yes, the changes in ad units are very important. I know of many founders whose number one sales channel is ChatGPT now and the conversation rates from those users are much, much higher. I also notice that behavior in myself.
Interesting way to connect memory on my side with GPT 5.2 after that, here’s what it suggested verbatim.
(I’m on free tier and probably not a regular enough reader so take this for what you will):
To the point and others feedback if you include some of your best articles and it can then suggest a framework and how to adapt it for my context/consulting then that becomes maybe a bit more interesting…
“3) Paid vs free for you (based on how you actually consume info)
Here’s my best guess based on your patterns:
• You like dense, re-usable frameworks you can turn into a slide, a rubric, a memo, a positioning doc.
• You don’t just read — you apply.
• But you also juggle a lot; if it’s not immediately useful, it doesn’t stick.
Start on free, but you’re a prime candidate for paid if the premium delivers real frameworks
If the premium tier is truly “deeper analysis + frameworks” (not just longer essays), it’s likely worth it for you specifically because:
• one good framework can pay for the year if it upgrades one pitch / proposal / narrative that closes a deal
• it will feed your “operator + investor brain” that you keep using across clients
But I would not auto-buy premium on day 1.
Decision rule for you:
• Read free for ~3–4 weeks.
• If you find yourself doing either of these twice:
1. copying passages into a doc because they sharpen your POV, or
2. turning an idea into a client-facing slide/memo,
then premium is worth it.
If you only find it entertaining or “interesting,” stay free.”
Very interesting experiment and idea! I tried it with the two services I use most: ChatGPT and Claude. Neither made a very compelling case, but ChatGPT tried a lot harder. 😄 Two quotes, one funny, one valuable (to me, at least):
"Your projects are small, weird, hybrid, human, physical, or infrastructural." 🤣 (this was in an argument against the relevance of The Leverage to what I do)
And about what The Leverage actually is: "for you, it’s: A high-quality lens you occasionally borrow."
Also interesting what Kacha Azema points out, which echoed my experience too: Claude responded in a more stiff and unusual way in presenting the argument to me, and wasn't very favorable, while still trying half-heartedly to make the case. ChatGPT sounded a lot more like normal ChatGPT, and did a better job making a case, but still ultimately ended with "probably not, for now".
Perhaps not surprisingly, neither offered me the subscription link at the end. Claude started researching other info sources that would be more relevant for me!