How to train AI to write like you

👋 Hi friends -

Welcome to The Newsletter Growth Memo. Twice a month, I share short reflections with my newsletter clients + other operators.

Zero formality, ads, or affiliate links - just a guy sharing learnings from working with media operators doing $25k-$2M+ / month with newsletters.

New reader highlights: Mike, Senior Director Insights & Analytics @Morning Brew | Preston, Group President @Firecrown | Brian, Senior Revenue Lead @beehiiv | Margy, CMO @ The Conversation

Everyone's timeline the past two weeks has been Claude agents and complicated MCP servers.

A lot of that stuff is real. We're doing cool things with it internally.

But the simple stuff is the highest-leverage.

Your writing is the #1 skill you need to apply AI to, and you need apply it fast.

It extends to sales emails, sales pages, newsletters, and social content.

Most of the things you need to generate attention and convert it into paying customers.

Many of you think AI writing is slop, and you’re wrong:

AI-drafted content, when trained appropriately, is excellent.

Ruben was kind enough to open up his AI writing process to folks in my newsletter accelerator in January.

He screen shared his Claude projects, pulled up the actual markdown file he uses to train AI on his voice, and drafted a newsletter in front of everybody.

You can read exactly how he trains AI on his voice here (his newsletter is excellent)

I’ll give you the TLDR below and how I use AI in my own writing.

AI is making it really easy to build products.

But AI does not have your taste!

The problem is neither you nor I are articulate about our taste in enough detail to train AI to write like us.

So Ruben built what he calls a "taste interview."

It's a prompt that asks you 100 questions to fully understand your style, contrarian takes, weaknesses, and expertise.

During my accelerator, Ruben pulled up WisprFlow, which transcribes his voice in real time, and talked through his answers.

I’ve taken the interview - it was pretty amazing for two reasons:

The whole thing saves as a single text file.

He uploaded it to Claude right in front of us and the difference was obvious.

Same AI, completely different output.

Sometimes our taste is bad!

You don’t want the blind leading the blind.

So you should give Claude (my preferred writing tool) context on skills AND on taste (I call this brand/voice context).

You might not realize it, but this is implicitly what you do when you train a new employee:

Back in 2022, I was a new, starry-eyed associate at The Boston Consulting Group.

My first manager drilled me on making great PowerPoint slides.

Be answer-first, always use a graph to articulate data, etc. etc.

These are universal slide principles. Skill-context. Everyone should know it.

But, some managers loved DENSE slides with big executive summaries (our private equity practice).

Our People & Org practice was much more ‘big idea’ and framework-y.

That’s brand/voice context.

For Skill context:

I upload newsletters I think are best-in-class into Claude, including editions from Justin Welsh and Ruben.

Both of these writers are informal, deeply tactical, and share great frameworks.

For brand/voice context:

Then I describe my own voice.

I try to write things you genuinely cannot just go Google.

I gave Claude both of those things plus Ruben’s interview output.

From there I think about writing more like sculpting.

AI gives me a decent clay shape and I mold it into my final email.

This newsletter is one of the highest leverage things I’ve done.

And this process has 4x’d that leverage (8 hours → 2-3 for writing).

Appreciate ya reading (these words were AI-drafted FYI), hope it helps.

That’s the letter.

- Nathan