Ruben Hassid spent his childhood computer time writing blog posts about video game optimization instead of playing the game. His brother thought he was nuts. Twenty years later, that pattern, test things repeatedly, figure out what worked, teach it simply, built a 700K LinkedIn following and 230K+ on Substack.
This week he shared what happened. Turns out his ChatGPT success in December 2022 came after a music label at 18, seven years of curation, and a ghostwriting gig in Berlin. The viral post was in many ways the result of a decade of practice.
Show Notes
[00:00] - Why He Keeps His Personal Brand Impersonal
His siblings don’t know what he does. He doesn’t find backstory relevant to daily content. This conversation is an exception.
[04:35] - Video Games to Content Creation
At nine, Ruben got obsessed with Guild Wars character builds. He wrote French blogs, realized the English forum had more readers, taught himself the language through Arctic Monkeys and comedy clips. The pattern: experiment, figure out what works, teach.
[09:00] - The ChatGPT Post
November 30, 2022. Berlin coworking space. He tested ChatGPT, spent a week reading academic papers, translated jargon like “few-shot prompting” into plain language, posted on LinkedIn. One million views in one post. 100K followers in three months. Then he went full-time.
[14:30] - The “Go All In” Myth
If you can’t build something while employed, you probably can’t build it without a paycheck either. Financial pressure makes you desperate. He overlapped a fintech job, ghostwriting, and personal content before making the leap.
[20:45] - What “Master AI Before It Masters You” Means
Not fear-mongering about replacement. The real problem: average output is now free and instant. A $1,000 article from 2021 looks like “just some words” today. The only path forward is taste so specific it can’t be replicated for free.
[26:00] - Engineers Are Breaking Down
Since Claude Code’s Opus 4.5 release, thousands of engineers are posting on Twitter asking what they’re even for. They can build anything in hours. Problem: they don’t know what to build. The excuse is gone. What remains: do you have taste?
[30:00] - Play Like a Kid
Every cover on his newsletter features a child. Pick one task. Use one AI. Don’t obsess over tools. Get small wins first. We’re monkeys who need rewards.
[34:00] - AI Forces Us to Be More Human
When Excel files and basic writing become automated, we go deeper. In the 1900s, 90% of Americans worked in food production. They couldn’t conceive of refrigeration, let alone the internet. Freed from survival labor, humans built things nobody predicted. Same pattern now.
[40:00] - “I Am Just a Text File”
He spent two hours answering Claude’s questions about his opinions, boundaries, writing style. Result: a markdown file, 1,000 lines, that captures his taste. Upload it anywhere, and AI writes like him. His grandchildren could talk to digital grandpa.
[43:00] - Animating His Grandmother
His mom lost her mother at 12. A handful of black-and-white photos. Ruben colorized them, created two-second animations. Sent one. His mom called crying. Her mother was moving.
[49:00] - Substack Must Stay Protected
On LinkedIn, maybe half his comments are AI-generated now. He compares giving everyone AI tools to handing a rifle to a monkey. Paid access and ID verification are coming. He’s not against it.
Two Quotes
“The more you forget about making money, the more money you make. Real traction doesn’t happen when you focus on the money.”
“Master AI before it masters you really means master it before you’re just average. Not because you’ll be replaced, but because why should anyone pay for your skill if average is free?”
What You Can Do Today
1. Build your taste file. Spend an hour answering questions about your opinions, boundaries, what you’d never say, how you’d phrase things. Save it as a document. Upload it to your AI projects.
2. Pick one AI task and play. Not the perfect tool. Not comprehensive mastery. One thing. Approach it like a nine-year-old with a video game.
Resources Mentioned
Steve Jobs’ Stanford Commencement Speech (Ruben watches it yearly)
Cursor ($20B AI coding company)
Where to Find Ruben
Substack newsletter, twice weekly, Wednesday and Sunday. 100 breakdowns per year. Most is free.
One Thing I’m Still Thinking About
Ruben said his grandchildren could have real conversations with digital grandpa someday. Then he paused and said he doesn’t know how to feel about it.
Neither do I.
What about you?
How This Was Made
This recap was built by uploading the show transcript as well as rambling my own thoughts via Wisprflow into a Claude custom project, containing our voice guidelines, then edited through four rounds: structure, skeptic audit, linguistic cleanup, and open-ending. The conversation took 56 minutes. The recap took longer. Thanks to Sam Illingworth for the tips on skepticism, and liguistics :)
Ruben’s right. Taste takes time even when AI does the typing.
