For years, I struggled with AI-assisted writing. I made every mistake. Here is my personal playbook, from hundreds of failures and a few massive wins, to help you find your own success.
The Counterintuitive Truth
In AI-assisted writing, the best practitioners often do less, not more.
The lesson: you need to move fast and break things. It sounds simple. It's incredibly hard to execute.
Why Most Approaches Fail
Many common approaches to AI-assisted writing are flawed at the root.
The root cause is usually one of three things:
Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
What I Tell Founders
Before deciding anything about AI-assisted writing, start with three questions:
What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around AI animation, AI music, AI storytelling, AI writing that I've been thinking about a lot lately.
What's Next
Best practice in AI-assisted writing is changing fast. What worked last year might not work next year. That's both the challenge and the opportunity.
My advice: stay curious, stay humble, and stay close to the people who are actually doing the work. Read less thought leadership and do more experiments. Talk to fewer consultants and more practitioners.
If you're building in this space, the best time to get AI-assisted writing right is before you need to. Don't wait for a crisis to force your hand.
I'll keep sharing what I learn. This stuff matters too much to keep to myself.
Frequently Asked Questions
Q:What would you do differently looking back?
I'd move faster on the things that were working and cut the things that weren't sooner. Most founders, myself included, hold onto failing strategies too long because of sunk cost. Speed of learning is everything.
Q:What was the biggest challenge in this case?
Almost always, the biggest challenge is people and alignment, not technology or strategy. Getting the right team focused on the right problem is harder than any technical challenge I've encountered.
Q:How long did it take to see results?
Most meaningful business results take 3-6 months to materialize. Anyone promising overnight success is selling something. The companies in my portfolio that grew fastest were the ones that stayed patient and consistent.
Q:Can these results be replicated?
The specific numbers will vary, but the underlying patterns and principles are transferable. The key is understanding the context behind the results, not just copying the tactics. Every company has unique constraints that shape what works.