I'm probably going to get some heat for this, but the AI writing space is a mess. I've been in it for 9 years, and it's time for some real talk.
I’m not a journalist or a professional writer. I’m an entrepreneur. I’ve built and sold two companies, RemoteTeam and MovieLaLa. I’ve invested in over 200 startups, including some of the biggest names in AI like Anthropic, OpenAI, Scale AI, and Hugging Face. I’ve seen the AI revolution from the inside, from the boardrooms to the code repositories. And I’m telling you, the way most people are using AI for writing is just plain wrong.
For years, I’ve been chasing the dream of the perfect AI writing assistant. A tool that could take my jumbled thoughts and turn them into polished, insightful articles. I’ve tried everything. I mean everything. From the earliest days of GPT-2 to the latest and greatest models, I’ve been a beta tester, an early adopter, and a paying customer. I’ve spent, what feels like, a small fortune on subscriptions and API credits.
And for a long time, I was getting nowhere. The content was generic. It was soulless. It sounded like a corporate press release written by a committee of robots. It was the kind of writing that makes you want to close the tab and go do something else. Anything else.
I almost gave up. I was convinced that AI-assisted writing was a dead end, at least for anyone who wanted to create something with a real voice and a real personality. I was ready to go back to the old way of doing things: just me, a blank page, and a lot of coffee.
But then, I had a breakthrough. It wasn’t a new tool or a new model. It was a simple, counterintuitive shift in my strategy. A shift that changed everything.
The Problem with AI Writing Tools
Before I tell you what I discovered, let’s talk about the problem. The market is flooded with AI writing tools that promise to do everything for you. They’ll write your blog posts, your social media updates, your emails, your ad copy. They’ll even write your novel, if you let them.
But here’s the dirty secret: they’re all using the same underlying technology. They’re all putting a pretty user interface on top of a large language model, like GPT-4. And while these models are incredibly powerful, they’re not magic. They’re pattern-matching machines. They’ve been trained on a massive dataset of text from the internet, and they’re very good at predicting the next word in a sequence.
But they don’t understand what they’re writing. They don’t have experiences. They don’t have opinions. They don’t have a soul. And it shows.
The result is a sea of generic, formulaic content that all sounds the same. It’s the "seven tips for..." and the "ultimate guide to..." and the "why you should..." articles that are polluting the internet. It’s the kind of content that’s written for search engines, not for humans.
I saw this firsthand with one of my portfolio companies. They were using an AI writing tool to generate blog posts for their content marketing. The articles were grammatically correct. They were well-structured. They were even optimized for SEO. But they were also incredibly boring. They had no personality. No spark. No reason for anyone to read them, let alone share them.
I told the founder, "You’re a brilliant guy. You have a unique perspective on this industry. Why are you letting a robot write your content for you?" He didn’t have a good answer. He was just following the herd. He was doing what all the marketing gurus were telling him to do.
The "Almost Gave Up" Moment
My own "almost gave up" moment came when I was trying to write a chapter for my book, "Becoming Top 1%". I was struggling with a section on the importance of building a personal brand. I knew what I wanted to say, but I couldn’t find the right words.
So, I did what any good tech bro would do. I turned to my AI writing assistant. I fed it my outline, my notes, and a few bullet points. I hit "generate". And I waited.
What came back was… fine. It was a perfectly competent, perfectly mediocre piece of writing. It had an introduction, a few body paragraphs, and a conclusion. It had some good points. But it wasn’t me. It didn’t have my voice. It didn’t have my stories. It didn’t have my passion.
I tried again. I tweaked the prompt. I gave it more context. I tried a different tool. I spent hours trying to coax a decent piece of writing out of the machine. But it was no use. The more I tried, the more frustrated I became.
I was ready to throw in the towel. I was convinced that I had wasted my time and money on a technology that was fundamentally flawed. I was about to delete all my AI writing apps and go back to the drawing board.
The Counterintuitive Shift
And then, I had an idea. It was a crazy idea, but I was desperate. I thought to myself, "What if I’m using this tool all wrong? What if, instead of trying to get the AI to be a writer, I should be treating it like an intern?"
Think about it. You wouldn’t ask an intern to write a whole chapter of your book. But you might ask them to do some research. Or to find some interesting stats. Or to come up with a few different ways to phrase a sentence. You would give them small, specific, well-defined tasks.
So, that’s what I did. I stopped trying to get the AI to write for me. Instead, I started using it for a series of micro-tasks. I would write a sentence, and then I would ask the AI to give me five different ways to say the same thing. I would write a paragraph, and then I would ask the AI to suggest a good analogy to illustrate my point. I would write a section, and then I would ask the AI to find a relevant quote from a famous entrepreneur.
And that’s when the magic happened. By breaking down the writing process into a series of small, manageable tasks, I was able to use the AI as a creative partner, not a crutch. It was like having a brainstorming buddy who was available 24/7 and never got tired.
This is the secret sauce. This is the counterintuitive shift that changed everything for me. Stop thinking of AI as a writer. Start thinking of it as a research assistant, a brainstorming partner, and a thesaurus on steroids.
Real-World Examples
Let me give you a few real-world examples of how I use this new strategy in my own writing.
When I’m writing a blog post, I’ll start by writing a rough draft myself. I’ll just get all my ideas down on paper, without worrying about grammar or style. Then, I’ll go back and use the AI to help me polish it. I’ll highlight a sentence and ask the AI to make it more concise. I’ll highlight a paragraph and ask the AI to make it more engaging. I’ll highlight a section and ask the AI to add a surprising statistic.
When I’m writing an email, I’ll use the AI to help me with the subject line. I’ll give it the body of the email and ask it to generate ten different subject lines. Then, I’ll pick the one that I like the best.
When I’m writing a social media post, I’ll use the AI to help me with the hook. I’ll give it the main point of the post and ask it to come up with a few different ways to grab the reader’s attention.
I’ve even used this strategy to help me with my angel investing. When I’m evaluating a startup, I’ll use the AI to help me with my due diligence. I’ll feed it the company’s pitch deck and ask it to identify the potential risks and opportunities. I’ll ask it to find articles and research papers on the market they’re in. It’s like having a team of analysts at my fingertips.
The Truth
The truth is that AI is not a magic bullet. It’s not going to turn you into a great writer overnight. But it can be an incredibly powerful tool, if you know how to use it.
The key is to stay in the driver’s seat. You’re the one with the ideas, the experiences, and the voice. The AI is just there to help you express them more effectively. It’s a tool for thought, not a replacement for thought.
So, stop waiting for the perfect AI writer. It’s not coming. The power is in how you, the human, use the imperfect tools we have today. The power is in your creativity, your curiosity, and your willingness to experiment.
Now, go write something that sounds like you, not like a robot. I, for one, am excited to read it.
Frequently Asked Questions
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.