How to AI

How to AI

AI & Agents
By
Ruben Hassid
The biggest AI newsletter on this list, and the one to send someone who keeps collecting prompts and finishing nothing.
SUBSCRIBERS
870,000+
HOW OFTEN
Weekly
ACCESS
Free, paid tier
WRITER
Ruben Hassid
Last updated
August 5, 2026

Preview

How to AI

What it is.

Ruben Hassid writes How to AI for 870,000+ subscribers, and it does one thing: follow the guide, with screenshots, and finish a task today.

Recent issues have covered Claude Cowork setup, which model to use for which job, and where the usage limits quietly bite.

It's free with a paid tier, and the audience is general, so a GTM reader takes the technique and leaves the rest.

What you get.

  • Step-by-step guides with screenshots at each stage
  • Model comparison written for someone choosing, not benchmarking
  • Setup walkthroughs for new tools as they land
  • Practical limits: where usage caps and settings cost you output
  • A free tier that carries the guides
OUR PICKS

Editions we'd start with.

How to set up Claude Cowork ↗

The setup guide, and a fair sample of how much hand-holding you get.

Fable 5 ↗

Which tasks deserve the expensive model and which don't. Useful for a team budget.

1,800 hours of Claude ↗

July 2026. Tips that come out of sustained use instead of a launch week.

ChatGPT shamelessly copied Claude ↗

His comparison of the two, written for someone picking one.

AI will fail ↗

The contrarian one, and worth reading against the rest of the archive.

Subscribe at the source.

Goes straight to Ruben Hassid.
Subscribe

Questions about How to AI

Will it cover B2B GTM?
Are the guides tested?

Questions about AI & Agents

Which AI model should a marketing team standardize on?
Are prompt libraries worth building?
How do you stop overpaying for AI?
Strengths
  • 870,000+ subscribers, so the guides get stress-tested by a huge audience.
  • Screenshots at every step, which makes the guides genuinely followable.
  • Covers model choice as a cost decision, not a benchmark race.
  • Free tier carries the practical material.
Limitations
  • General audience, so there's no B2B GTM context at all.
  • Headlines lean on hooks, which can oversell the content.
  • Tool-specific and fast-moving, so older guides go stale.
  • He sells courses, which the newsletter feeds.
Skip this if
  • Skip it if you already run the tools confidently and need no setup walkthroughs.
Ideal for
  • Marketers learning AI tools
  • Teams standardizing on Claude or ChatGPT
  • Anyone stuck collecting prompts
  • Stage: Any stage

Reading is the cheap part.

TripleDart runs organic, paid, and GTM engineering for 300+ B2B tech companies. Bring us the number you have to hit.