Why I Haven’t Posted on Medium in 4 Months
And why the wall I hit pointed me in the right direction.
I almost shut WisePilot AI down.
Not because I ran out of money. Not because I lost interest. But because in the span of a single announcement, the direction I had been building toward became a dead end overnight.
Let me back up.
What I Was Building
For most of 2025, WisePilot AI was a collection of custom GPTs designed specifically for small business owners.
Not the generic, “ask it anything” kind of AI tools. These were promptless AI tools, meaning the small business owner didn’t need to know how to write a prompt. They just answered a few guided questions and got a useful output. Review responses, social media content, email subject lines, product listings for resellers. Practical stuff for the people running the kinds of businesses where there’s no marketing department, just the owner and maybe a part-time employee.
A few of those tools, including WiseBlog and WiseFAQ, I actually built to use in my own work. In October of 2024 I had been introduced to something called Answer Engine Optimization (AEO), and I became obsessed with it immediately.
AEO is about structuring content so AI systems like ChatGPT, Gemini, and Perplexity can extract it, understand it, and use it as a direct answer. Not just ranking in Google. Actually being referenced inside AI-generated responses.
I introduced it to my company and started practicing it in my day job. And by March of 2025 I was implementing AEO on actual small business websites for real clients.
WiseBlog and WiseFAQ were tools I built to help me do that work faster. And I had started to see that nobody else was filling the gap when it came to AEO for marketers (like me) or small business owners. There were plenty of tools for social media, email, review management. But AEO tools built specifically for the marketers or the small business owner trying to stay visible as search shifted toward AI? Nobody.
So I was building. I was excited. I even claimed “AEO Tools” as a category for WisePilot AI.
And then OpenAI made an announcement.
The Moment Everything Changed
At the end of 2025, OpenAI announced custom apps within ChatGPT.
I saw it and immediately understood what it meant. Custom GPTs, the format I had built my entire product line around, was effectively being commoditized by the very platform it ran on. What I had built could be replicated by anyone inside ChatGPT itself. The moat I thought I had wasn’t a moat at all.
I had just launched WiseBlog and WiseFAQ as custom GPTs. I had just claimed AEO tools as a category. Through my day job I had proof of concept that these tools work. I had momentum.
And now I suddenly found myself staring at a dead end.
Get WisePilot AI’s stories in your inbox
Join Medium for free to get updates from this writer.
The Lowest Point
I am going to be honest about what that felt like, because I think founders who sugarcoat the hard moments do a disservice to everyone else going through them.
It was seriously depressing.
I had made a promise to my wife. She had been supportive of WisePilot AI through all of it, and I had told her that if things went the way I believed they could, she would be able to leave her job in the summer of 2026. Sitting with the idea of shutting everything down, I felt like I had let her down, like I had failed her. I felt absolutely defeated.
I spent some real time in prayer during that stretch. Not looking for a sign, just trying to get clear.
And what came back to me was the thing I had been doing for a year that nobody had told me to do. Practicing AEO. On real websites. For real small business owners. Seeing it work.
I had already built the tools I needed. I had already identified the gap in the market. I had already been doing the work professionally.
The pivot wasn’t a gamble. It was the obvious next step. I just needed to stop mourning the direction I was leaving and start building the one that was already in front of me.
The Pivot
In January of 2026, I restructured everything.
I moved WiseBlog and WiseFAQ out of custom GPTs and into a proper production environment. I rebuilt the website around AEO as the core category. I started building the full WisePilot AEO Toolkit, bringing each tool into a stable, shareable format that didn’t depend on any single platform.
Within weeks, the toolkit was live. WiseFAQ, WiseBlog, WiseStitch, WiseSchema. A complete production system for small businesses and solo marketers who want to build structured, AI-readable content without needing a developer or an agency.
The toolkit is built around one idea: most small businesses are invisible to AI search not because they have bad content, but because their content isn’t structured for answer extraction. AEO tools fix that. That is what WisePilot AI is now built to do.
Why I’m Telling You This
Because if you are a founder who hit a wall recently, I want you to know that the wall is sometimes pointing you somewhere. Don’t give up. Look to see where it is pointing, and go in that direction.
I was down. I was genuinely considering walking away from something I had poured real time, energy, and passion into. And what came out of that low point ended up being the clearest, most focused version of WisePilot AI I have ever had.
The silence on here for the last four months wasn’t inactivity. It was a rebuild.
And I am more excited about what we are building now than I have been at any point since I started.
If you are curious about what WisePilot AI does now, the best place to start is the AEO tools page. It explains the category, how these tools work, and who they are built for.
I will be posting more regularly from here on out. Not to fill a content calendar, but when there is something real worth sharing.
This felt like one of those times.
