The Digital Scavenger Hunt: Automating the Weekend with OKGarageSales.com

If SoonerClassifieds.com was a lesson in blunt-force trauma—me banging my head against CSS until the wall cracked—then OKGarageSales.com was supposed to be the refined follow-up. The jazz record to the previous punk rock album.

I decided to spin up a second project. The goal? A dedicated portal for garage sales in Oklahoma City. It’s a niche within a niche. It’s hyper-local, high-volume, and ephemeral. Garage sales pop up on Friday and vanish by Sunday. A static directory doesn’t work; it needs to be alive.

I went into this collaboration with the Machine (my AI counterpart) with the scars of the previous weeks fresh on my mind. I wasn’t going to make the same mistakes. I wasn’t going to beg for snippets. This time, I wanted to act less like a frantic construction worker and more like a Brand Manager and Systems Architect.

We focused on two main pillars: The Identity (Branding) and The Engine (Python Automation).

Part 1: The Identity Crisis (and Resolution)

Branding is usually a weeks-long process involving mood boards, creative directors, and billable hours that make you weep. I wanted a logo for OKGarageSales that felt nostalgic but clean. I wanted it to scream “Saturday Morning.”

This is where the collaboration became… weirdly telepathic.

In the past, I would have asked: “Make me a logo for a garage sale site.” The AI would have spit out generic clip art of a gavel or a price tag.

But I’ve learned. I’ve evolved.

The Prompt Evolution: Instead of a request, I gave it a persona. I told the AI to act as a “Minimalist Graphic Designer with a focus on Retro-Americana.” I fed it specific constraints:

• Palette: High contrast.
• Vibe: 1980s newspaper classifieds meet modern flat design.
• Constraint: No text inside the icon.

The “Win” here wasn’t getting it right on the first try. It was the speed of iteration. We played a game of visual ping-pong.

• Me: “Too busy. Simplify the roofline.”
• AI: “Here is Version 4.”
• Me: “Make the tag distinct. Use the orange from the OK state flag.”

[Insert Screenshot: The evolution of the OKGarageSales logo – distinct versions side by side]

We settled on a final design in about 45 minutes. A process that typically takes days. But the “Loss” here—if you can call it that—was the realization of my own lack of vocabulary. I found myself struggling to describe why a curve looked “cheap.” The machine forced me to learn the terminology of design (kerning, negative space, vector flatness) just to get what was in my head onto the screen. I had to become a better art director to get a better artist.

[Insert Screenshot: The Final OKGarageSales.com Logo/Brand Mark]

Part 2: The Python Trap

Once the site looked pretty, it needed a brain. I didn’t just want a manual submission form; I wanted to explore automation. I wanted to understand how to manipulate data.

I decided we needed a Python script.

Now, let’s be clear: I do not know Python. I know of Python. I know it’s a snake, and I know it runs the internet.

I asked the AI to help me build a script to organize potential listings. This was a massive risk. With CSS, if you break it, things just look ugly. With Python, if you break it, nothing happens. You stare at a terminal window that mocks you.

The “Loss”: The Black Box Effect Early in the session, I asked the AI to “write a script.” It did. I pasted it. It failed.

I got an error message that looked like hieroglyphics. My instinct was to blame the “stupid bot.” You wrote bad code!

But then I remembered the lesson from SoonerClassifieds: Garbage In, Garbage Out.

I realized I hadn’t told the AI where the script was running. I hadn’t told it I was on a Windows machine. I hadn’t told it I didn’t have the libraries installed. I was trying to drive a car without putting gas in it.

The “Win”: The Co-Pilot Shift I changed my approach. I stopped asking for the code and started asking for the manual.

“Treat me like I’ve never opened a terminal in my life. Walk me through setting up the environment first.”

This was the breakthrough. The AI shifted from “Developer” mode to “IT Support” mode. It walked me through installing dependencies. It explained what a virtual environment was.

[Insert Screenshot: The Python Script code block or the Terminal running the script]

When the script finally ran—when I saw white text cascading down the black screen, parsing data exactly as I had imagined—it was a rush. It was a different kind of win than seeing a pretty website. It was the feeling of holding a power tool I didn’t know how to use five minutes ago, and successfully drilling a hole.

The Collaboration Deconstructed

So, what is the difference between SoonerClassifieds and OKGarageSales?

With SoonerClassifieds, I was fighting the machine to fix mistakes. With OKGarageSales, I was guiding the machine to execute a vision.

The “Losses” in this project were mostly intellectual—the moments where I hit the limit of my own logic. The AI can write the loop, but it can’t tell you why you need the loop. It can build the trap, but you have to decide what you’re trying to catch.

I realized that as these tools get better, the “Tech Guy” isn’t the guy who knows the syntax. The “Tech Guy” is the one who knows what to ask for.

The “Antifragile” Workflow

I’m trying to build these projects using Nassim Taleb’s “Barbell Strategy” (a concept I’ve been obsessing over lately).

• The Floor (Safety): I use the AI to write robust, error-checked code. I force it to comment every line so I can understand it. This prevents the project from collapsing under its own weight.
• The Cap (Upside): I use the time saved on coding to take “creative risks”—weird branding choices, aggressive marketing angles, features that shouldn’t work but might.

OKGarageSales.com is the result of that strategy. It’s a low-stakes bet with high-upside potential, built by a guy who can’t code and a machine that can’t think.

[Insert Screenshot: The OKGarageSales Homepage or Landing Page]

Final Thoughts: The Centaur Architect

We are moving away from the era of “I built this.” We are entering the era of “We built this.”

The “We” is me and the model.

In this project, the machine was the hands, but I had to be the eyes. It was faster than SoonerClassifieds because I stopped treating the AI like a magic 8-ball and started treating it like a junior engineer who needs very, very specific instructions.

I learned that prompt engineering isn’t about vocabulary; it’s about empathy for the system. You have to understand how the model “thinks” (predicts) to get it to give you what you want. You have to feed it context, remind it of the goal, and occasionally, tell it to stop hallucinating and look at the file you just gave it.

OKGarageSales is live. The logo is retro-cool. The Python script works. And I’m still a 43-year-old sales guy from OKC. But now, I’m a sales guy with a very powerful, very strange digital intern.

And we’re just getting started.