Ruben Hassid

Things Ruben Says on Podcasts

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Where to Find Them

Ruben Hassid writes How to AI , writes https://ruben.substack.com , writes ROBOTS ATE MY HOMEWORK , writes Sacred Business Flow , writes Blockbuster Blueprint , writes Slow AI , writes Wander Wealth and writes Build to Thrive . They have also been a guest on Agency Intelligence: The Insurance Podcast Network and Marketing Against The Grain .

Recently: “How a Top AI Expert Actually Uses Claude” on Marketing Against The Grain (October 2026); “Who writes this?” on How to AI (October 2026); “One Claude.” on How to AI (October 2026); “Ruben Hassid On Mastering AI Before It Masters You” on Agency Intelligence: The Insurance Podcast Network (October 2026); “Claude for Legal.” on How to AI (October 2026); “777” on How to AI (October 2026).

What They Said

“Writing is kind of like flirting. So, if everyone is using the same pickup lines, then … even if you have like the most effective pickup line, it becomes boring. The second problem is writing is thinking, and you can tell if someone wrote about something and they never really experienced it, they didn't go through it.” β€” Ruben Hassid, Marketing Against The Grain

The hosts noted that they and Hassid, an AI educator, now write every word of their newsletters themselves. Asked why not just build an AI writing-style skill, Hassid says it locks you into one predictable voice, while real writing should change as the writer does.

Marketing Against The Grain Β· 2026-10-27 Permalink β†’ Listen β†’
Marketing Against The Grain Around 01:20 into the episode
Ruben Hassid

That's the least ambitious introduction I've ever received, right? Like, hey,

Speaker 3

…Kieran. How, when it comes to writing, that we're all going completely away from AI, and that Ruben's writing every word of his newsletter, you're writing every word of your newsletter. We're all using AI far or less in our writing, which is, I think, very interesting, just as an aside.

Ruben Hassid

Yeah, writing is kind of like flirting. So, if everyone is using the same pickup lines, then once again, I mean, even if you have like the most effective pickup line, it becomes boring. The second problem is writing is thinking, and you can tell if someone wrote about something and they never really experienced it, they didn't go through it. So,

Kieran Flanagan

let's break this down a little bit for our audience, Ruben. So, I started with AI, and most of the content I created for external people was how to use it for creating content. And back when the models were, especially Claude, back when Claude came out with, I can't remember the model,

Speaker 3

3.5, I think.

Kieran Flanagan

I was having incredible results using AI for write-in, and that was like what I did for a year. And I'm similar to you now, I try not to use it at all. But let's try to break this down. So, if I'm listening to you, and I'm like, well, why can't I just build a writing style, right? And then AI can…

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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