Whether you’re pitching ideas internally, selling your vision to a founder, or trying to get someone to care about what you say on social media, writing well matters.

And it’s hardly a new skill. Some of the most timeless marketing advice dates back over 100 years to the early days of copywriting. The ability to turn words into attention, engagement, and ultimately action.

AI promised to be an incredible tool for creators. Do more. Create more. Grow more. I’ve created many tutorials to help you do that. That’s why it’s likely quite jarring for me to say - I’m not going to use AI to write anymore, and I don’t think you should either.

The hard truth about AI is that just because you can do more doesn’t mean you should.

How to build a personal audience with AI?

I’m not a creator. In fact, I struggle to find time in my week to create content.

Still, my audience size would let me call myself a B2B creator: +116k on LinkedIn, +100k on YouTube, 17k on Substack (12 months old), and +20k on X.

My ambition is to reach +100k on each platform, which is very doable. The only limitation is time.

I spend most of my time on LinkedIn & YouTube, so it’s no surprise they’re above target. I’m currently increasing my investment in Substack and X.

This made AI a great unlock for me. Someone who’s good at crafting content, ambitious to grow a personal audience, and whose core limitation is time.

For context, when Claude’s first Sonnet model dropped in March 2024, my LinkedIn and YouTube numbers were likely half of what they are now; I had no Substack and had given up on X. I just didn’t have enough time.

I was an early adopter of AI for content. I built a personal writing app that used a context layer long before people started talking about it as a competitive advantage. And it really worked. The content AI created was good. If you gave it a great idea, subtext, instructions on what you wanted, and how to format it, it usually produced a great post. Because very few people were using AI to create content the right way, it was a real competitive advantage.

It was like having a superpower: a way to turn ideas into crafted content, mapped to your style, in a short amount of time, like having a dedicated content team on staff, helping you build a true publishing engine.

Then, like a true builder, you make the content systems more sophisticated. You layer on more.

A context engine that can build a variety of writing styles, mapped to individual platforms. Skills that enrich content with modules tailored to specific posts on specific platforms. The ability for AI to continually ingest your data and auto-update skills based on what content is performing and not performing, so you can stay ahead of the curve, e.g., what content formats are working on each platform. You start to obsess over the perfectly formatted YouTube transcript, the exact timings of the hook, the promise, the payoff. You grade your guests: what they did well, what they didn’t, and you find more guests who map to winning patterns.

You build, you automate, you make a better, more complex, more sophisticated system that impresses more people; you set up an entire MCP server to make your content system available in any model so you can compare and contrast content quality, picking the best model output for the best idea, mixing and matching where it makes sense.

Then you realize something ….

What the fuck am I even doing?

I started using AI because I didn’t have enough time to create content. Now I’m spending more time building systems to create content than actually creating it.

And the more sophisticated the systems became, the further I got from the thing I actually enjoyed. Coming up with ideas, writing about them, putting them into the world. You know, just creating shit.

I’d turned creativity into an engineering problem.

One post that really resonated with me was Varun’s, founder of Clay, on their internal policy about writing. To summarise some of their key points:

1. You must stand behind every idea and sentence

2. Writing is thinking

3. More time should be spent writing a document than consuming it

4. Longer is not better

This was one of the truest posts I’d read on AI.

I’d already started to see AI making people lazy in how they used it internally. Especially with the documents they were shipping. Memos, presentations, any strategic doc. Any writing task felt like admin. Something AI should do.

I started calling them “TED Talks.”

Everything is exceptionally worded, professionally structured, pitch-perfect, and substance-free. AI creates more noise because the barrier to entry is now a single prompt.

If you remove thinking from the documents you create, then your work is merely a prompt to an LLM engine.

And I think the same thing is happening with creativity.

Creativity is earned. It can’t be manufactured. It can’t be outsourced to a model.

And much like outsourcing your thinking to AI, outsourcing your creativity to AI dulls that spark. Every page looks blanker. Starting anything without first asking AI to draft something for you is harder. Eventually, it just loses the magic that once made you fall in love with it. You’ve reduced it to a workflow.

This happened to us with Marketing Against the Grain. When you’re deep into AI, everything looks like an AI problem to solve. We created an AI workflow, a team of agents with skills that could go from trend to a perfectly formatted transcript in a short time. And the content, on the surface, was good. It just didn’t perform well, and eventually we just wanted to quit. It felt inauthentic, like my brain was rejecting someone else telling me what was good. Maybe the content was great, but part of YouTube is showing up excited to present it. And we were not excited. The channel stalled. Showing up to do an episode was a grind. Kipp and I only care about winning. We debated what to do. Until we eventually came up with a clear and concise strategy:

“Let’s just do shit we enjoy”

And that was it. If we did an episode we didn’t enjoy. Bin it. Don’t put it live. Everything we put out now is just things we jam about on our personal WhatsApp. And that one change helped us surpass 100k subscribers. Only 0.3% of channels make it that far.

I’m not advocating giving up on AI for content. I’d give up outsourcing the parts of content creation that make it worth doing.

That’s an important distinction.

Because there are still parts of the content creation process where AI can prove useful. Just not the parts that make the content yours.

The writing stack and what to automate

When you think about writing, there is a simple loop:

AI works so well for writing because it’s such a clear loop, where each part feeds the next. It’s not hard to automate. The temptation is to automate it all.

And that’s exactly the trap most people fall into.

My argument now is to automate none of the actual writing. The parts that make you, you.

You might look at this graphic and say, “Wait, he’s using a lot of AI still.” And I am. But there’s an important distinction between having AI help with the process and having it do the creative work for you. And even in those places where it assists, it’s still done with guardrails.

1. Research - Until recently, I felt AI might still be good for researching trends, giving me ideas. Maybe a couple of months ago, the above flow would be Research → Ideas. I created a system, which I shared here, where AI could research trends and turn them into content ideas perfectly mapped to my audience. And when building the last iteration of my content system, I realized a couple of things:

• I rarely, if ever, used these ideas. Nearly all my content comes from the process I described above. Ideas come to me because I’ve spent so many years creating content. I couldn’t stick to someone else’s, even a model spoon-feeding me ideas.

• The ones I did use underperformed the ones that came from my brain as a subconscious thought. Why. The same reason YouTube stalled. I wasn’t excited by them. They weren’t mine.

I think it’s because AI drags you to the center. Those ideas don’t feel authentic because I didn’t spot them, experience them, or think of them in a quiet moment, so they didn’t feel like mine.

Obviously, AI is a great research tool, in the same way great writers might use a researcher for fact-checking, retrieving statistics, or finding examples. But that’s more like a better version of a traditional search engine, using AI to craft exceptional content.

2. Drafting - I recently wrote a US bestseller with my good friend Kipp called Loop. It turns out writing a book is hard. It’s not the writing. It’s making sure some threads build over the course of each chapter. Your story develops. Your worldview gradually expands, sucks in the audience, and exits with each loose end tightly closed, leaving nothing unsaid.

With AI, the temptation- and what I know a lot of people do- is to give it a half-drafted piece of content and ask it to ‘edit’, e.g., finish. I don’t allow AI to change my words. What I ask it for is:

Everything is a suggestion; I make any edits by hand. I don’t want AI touching my words. I don’t want to be a TED Talk. I want my content to be imperfect. My content is imperfect. So am I.

Obviously this is only relevant for long-form content.

Analyzing performance is self-explanatory. Have AI pull your content performance each month and give you a readout of what’s going well and what’s not going well.

My approach might not match yours.

I don’t use AI for any social content, e.g., X, LinkedIn, YouTube. Zero. Not for ideation, research, edits, anything. For short-form content (X, LinkedIn), the process is simple: have an idea, write, publish it, don’t overthink it. AI makes you overthink because you can analyze and iterate on everything so quickly. For YouTube, very similar. I obviously use AI for the show-and-tells we do; e.g., we literally showcase AI workflows.

For Substack, here’s the process I’m doing now. I write out the entire post, I edit it myself, e.g I actually re-read it a bunch of times, I think people forget this is the most important part of writing

And within the draft I’ll put instructions for my AI editor, e.g.

{I’d like to turn this framework into a graphic that fits with my Substack style}

{Please add the date this book was published.}

Basically, instructions for it to fill in the blanks or create imagery. Once those are added, I’ll use the editor prompt above and read the suggested changes, mostly on the beats of the post, never the words or the style; I’ll make any I feel make the post more valuable, but nothing that alters the content. And publish.

With Substack, I’m making specific choices to keep posts authentic, all me, and high-quality by publishing twice a month.

I’m also going to hire a real human editor to work with me, because humans > AI when it comes to all things content :)

I’ve realized that some of this is what you’re willing to sacrifice to be authentic.

Realistically, I didn’t have time to write a Substack post this week. I had Norovirus for most of the week, and I’m so swamped with work projects that it’s tempting to give AI my idea and have it spit back a perfectly worded, structured post.

But fuck that.

I’d rather have an imperfect, authentically me post. I’d rather put more creative coins in the bank by doing the work, building more repetitions, than outsource to a model.

Until Net Time,

Happy AI’fying

Kieran

A lot of the job descriptions I’ve used would need rewriting today.

Look at who Ramp brought into a marketing brainstorm: someone who had spent four years leading social for MrBeast. They ended up putting Brian Baumgartner, Kevin from The Office, in a glass box in New York doing expense reports.

ClickUp pays comedians and outside creators to join its writers’ rooms and improve its scripts.

These are software companies recruiting people who understand entertainment.

In 2021, I led HubSpot’s acquisition of The Hustle because we saw this trend. Make relevant content, not just educational.

Now, AI has commoditized so much of what we used to do. It can produce an infinite number of articles, videos, and campaigns. Your competitors have access to the same tools—the same models. You don’t even need to be a great prompter to get AI to produce pretty good results.

AI is commoditizing the consideration phase. And that changes where I’d spend my hiring budget.

I’d want people who can make our product interesting enough to watch. People who understand what our customers send to their friends. People who can convince creators with great audiences to build something with us.

When marketing moved to digital, everything became more professional. Optimized to the very last metric. It lost its edge, soul, and personality.

The battle is now in the awareness stage. To win, I’d make these three roles a critical part of my team.

Quick note: I’m going to be posting every two weeks for the rest of this year. I took on some new things. Became a best selling author. And finally reached 100k subs on YouTube. In doing all that, I need to fix my workload and I want to ensure quality is very high.

1. Viral Producer

What is it?

Someone who runs experiments that get us known. That help us win the stage above consideration → Awareness.

They take a problem our product solves and turn it into something people want to watch, participate in, or talk about. They own getting the idea made, getting it distributed, and deciding whether it deserves another investment.

Why now?

In PLG businesses, we built strong experimentation teams around sign-ups, activation, and conversion. I want that same discipline applied earlier, to awareness.

As buyers do more of their research inside AI assistants, I think being familiar before they start comparing products becomes more critical.

At the same time, AI makes parts of creative production cheaper. We can test more concepts before committing to a big production. That creates room for someone who combines a growth operator’s appetite for experiments with a producer’s ability to make things people care about.

Example

Ramp sells finance software. They put Kevin from The Office in a glass box in New York and made him process receipts by hand while a tracker compared him with Ramp.

[Brian video here]

Then came a partnership with Kumar, a retired-accountant character whose finance videos look like thriller trailers. And a Broadway musical about paying bills, starring Billy Porter.

This is the range of work I mean by a Viral Producer.

How it works

Ramp has a dedicated Creative Experimentation team reporting into growth marketing. Its current roster includes:

• Kendall Tucker, Director of Creative Experimentation.

• Three senior creative producers: Amber Layne, Mads Montana and Nolan Lunsford. Their backgrounds include acting, comedy, dance and YouTube entertainment.

• Dallas Thompson, Influencer Manager.

• Robert Lipman, Visibility Engineer.

• A rotating group of freelance producers, directors, comedians and other talent.

The team owns the idea, execution and clips, and measures views, shares and downstream impact.

2. Internet Comedian

What is it?

Someone who makes your brand something customers send to their friends.

That could mean memes, short sketches, recurring characters, or an AI remix of a trend. They understand internet culture.

Why now?

Social is the new SEO

In the inbound era, you scaled via keywords and content. Now, you scale through memes and shit posting.

Basically, you have to be relevant online. The early-stage founders I speak with, pre-seed, seed, and series A, are more marketing than engineering. And they understand you need to do things differently online.

Check out this from a company called Monid.ai, whose co-founder Shengkun I met earlier this week. Their product is great. Their marketing is also great.

AI gives that person more ways to execute. They can mock up a character, edit a clip, or try several versions quickly. The valuable skill is having taste and judgment to know what would be funny in the first place.

And we’ve done this before. In 1957, Jim Henson was making puppet commercials for Wilkins Coffee. In one, a puppet refuses the coffee and gets shot with a cannon. Watch it here.

Imagine getting that through your brand review today. We’ve lost our edge.

We have better production tools than ever, and so much B2B marketing still sounds like a corporate induction.

Example

Look at how Alexandr Wang promoted Muse.

Meta’s chief AI officer turned its fluffy mascot into material for memes, pop-culture references and jokes about competitors. Business Insider counted more than 300 posts on X between Muse’s launch on September 8 and its September 23 report. Source

When someone complimented his social team, Wang said he was posting himself:

“I don’t let the corposlops near my tweet cannon.” Source

That’s the instinct you need in an Internet Comedian. Someone who sees what people are already laughing about and knows how to put our product into the joke. Obviously Alex Wang is much more than an internet comedian lol

ClickUp has built a more formal process around this. It pays comedians and outside creators to join writers’ rooms, bring ideas, and improve scripts.

How it works

This is simple: you either can do this content or you can’t. You either have this skill in-house, or you don’t.

Hire a comedic script writer. Do a contract to try it out. Look for young, out-of-college grads who understand how to create content people share.

Pay a comedy writer or creator to turn those observations into five premises. Produce a few simple versions before commissioning anything expensive.

3. Creator Deal Maker

What is it?

Someone who makes the creators your customers follow want to work with you.

They find the right talent, understand what those creators want to build and put together an offer worth accepting.

Why now?

If a creator is a good fit for your company, they’re probably a good fit for several others.

You need a reason for them to choose you and stay. That might include money, production support, access, distribution or a project they couldn’t easily make alone.

This takes commercial judgement and relationship skills. A standard sponsorship email only gets you so far.

Example

At HubSpot, one of the things we did in our creator programme was cross-promote the creators.

Being part of the programme helped them grow their own audiences. We had something valuable to offer beyond the sponsorship fee, and a reason for them to keep participating.

We also bought half their ad inventory for 2 years, locking them into long-term deals meant they had predictability on their revenue, and we got the upside on their audience growth as we had locked in the CPM cost. For example, one of our creators grew their audience 5x during those 2 years, and that was all free visibility for us.

That’s the kind of deal I’d want this person to figure out: what can we offer that becomes more valuable the longer we work together?

How it works

First, check who actually engages with the creator. Look at relevant job roles, markets and the quality of the conversations.

I built a creator grader to help with this. In one case, roughly 80% of the engaging profiles I examined had no connections and looked newly created. That was a reason to investigate before paying. A big engagement number can hide a poor audience.

Then ask what the creator wants to build. Match that ambition with something your company can genuinely provide.

Start with a paid three-part pilot. Agree the fee, creative control, usage rights and what would justify continuing.

I’d look for someone who can explain both sides of the deal: why it works for our business, and why the creator would choose it over another offer.

Before opening your next marketing role, put a small budget behind one of these experiments.

Commission an entertaining product concept. Bring a comedian into a writing session. Build an offer for a creator you’d love to work with.

You’ll learn far more about the skills your team is missing by making something together than by rewriting the same job description you used last year.

Until Next Time,

Happy AI;fying

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