Conversions happen in conversations

Today, I’ll do two things:

  1. Explain a basic belief that helps you sell more.

  2. Give you an advanced way to use it that I have never seen anyone else do.

Sounds cool?

Let’s go.

“Conversions happen in conversations.”


People will buy an ungodly amount more if you actually talk to them.

Logical? Yes.

Common sense? No.

And you can realistically 50X the volume of conversations you have every single day. 50 outbound messages. 50 calls. 50 emails. For most of you that would be 50 times more. (If not… you cool 😎)

While sheer volume is a fantastic way to start a business…


  • a marketer + engineer

  • a magician + game designer

  • lazy


What if there was a way to automate conversations?

(there is)
*but not completely

To find that, we need to “find” the difference between any DM and any newsletter.

That is: Newsletters are the same for everyone. Even if I write them conversationally, you subconsciously know there are 100s of people on my list reading the same words.

Newsletters do not feel like a conversation.

Pro tip: that doesn’t apply to replies 💁‍♂️

But DMs?

DMs are different. Every response is based on what was said previously.

DMs feel like a conversation.

So, to automate a conversation, you need your responses to be based on what the other person said.


Automating conversations with AI is stupid.

At least the way most people use AI. (there’s a very technical way to use AI effectively, but you won’t know it unless you’re an engineer).

And AI’s current capabilities are simply not powerful enough.

So, how do you do it?

Like you’d do it in a game.

There are hundreds of story-driven titles that have pre-coded dialogues that give players a different (but still limited) set of responses.

The Curse of Monkey Island did that brilliantly in 1997.

You can do the same thing in your website.


  1. Ask questions.

  2. Give people a few possible replies.

Most quiz apps do this wonderfully. I like using Tally for how fast making quizzes in there is.

But where can you add those automated conversations?


New customer surveys. Newsletter signsup. Contact forms.

I even wrote an article about contact forms today (with a few extra juicy examples):

I hope you learned something,
— Jordan