The Profitable Pivot (So Far)

Back in 2019, I started a technical documentation agency called DocumentWrite. At that point, I had been working in tech for nearly a decade, and one thing was clear: every team I encountered was woefully behind on documentation. It didn’t matter if they were early-stage startups or scaling companies- nobody wanted to touch the docs. So I did. For the first year, it was just me, running everything.

Growing and Expanding

I’ve never been the most organized person, so about a year in, I hired an assistant on Upwork. I had just finished Copyhackers (shoutout to Joanna Wiebe), and one piece of advice stuck: hire help before you feel ready. It took me six months to figure out how to delegate properly, but that experience taught me something critical. Even though we were delivering SOPs and documentation to our clients, my own company was starving for internal structure.

That same year, I hired my first writer. At first, I worked alongside them. I didn’t want to hand over client work until I trusted my own process. Eventually, I grew more confident and started shifting more work their way so I could focus on marketing and running the business.

Most of our clients were newly funded startups- teams that had just raised a round and were building something technical, usually for an engineering audience. The challenge? Their users didn’t know how anything worked outside of the dev team. We solved that.

As we grew, I found more writers through Twitter Spaces I hosted weekly. By year three, DocumentWrite was generating over $20K a month. I had contractors handling writing and admin, and I was working maybe 20 hours a week. It was magnificent.

The Change

Then 2023 hit. The climate shifted. Interest rates rose. Tech teams got leaner, and documentation was one of the first things to get pulled in-house. ChatGPT didn’t help. With AI tools reducing the blank page problem, many companies felt they could handle their docs internally.

Demand dropped hard. Clients no longer wanted to pay our $5K+ pricing, and they were right to ask for clearer ROI. Developer education was still important, but expectations had changed. I let go of my team. In early 2024, I quietly shut the lights off for DocumentWrite.

The Pivot

I live in North Carolina, and I started spending more time at local business events and tech meetups. Week after week, I kept hearing the same thing: local businesses felt like they should be using AI, but they were overwhelmed. Meanwhile, AI startups were pushing products that their target customers weren’t ready for.

There was a gap- a missing step between "I don’t understand AI" and "Here’s a powerful tool that automates half your workflow."

So I used my background to build that missing bridge. I started helping AI companies create simple educational courses around their core product. Here's the flow:

We build an email list

We give away a free course demystifying AI

We upsell the full course, designed to lead naturally into product adoption

The result? Across the board, course subscribers are significantly more likely to convert than cold leads. Subscribers who go through the course are 30% more likely to purchase the AI company’s core product.

It’s still early days, but it’s working. So far we’ve worked with 3 companies, and one of them made an extra $18K after launching their course. I'm still refining the playbook, but initial results are promising.

This post is already long, so I’ll stop here. If you're curious about the process or want to see what it looks like under the hood, let me know. I'm happy to write that out in a future post.