My Twenty-Dollar Assistant (AI in the workplace)

A year ago, I started thinking seriously about hiring what would essentially be a personal assistant. Someone in the buying department who could handle the growing pile of e-commerce work I was generating. There was how I was doing it and how I wanted to do it, and the gap between those two required more labor than I was willing to give.

For years I managed buying between customers at the counter, turning what should be one of the most important parts of owning a store into a nuisance task. I wouldn’t expand buying because I didn’t have the time. Looking back, that was probably one of my bigger mistakes. Now it's my primary job.

I first started using AI to build a new D&D campaign. Combined with a wiki, it was intoxicating. I had continents mapped, pantheons defined, and NPC relationships modeled to the point I could feel how they’d interact by modeling dialogue based on backgrounds, often generated with the help of AI.

In three months I created enough material to last twenty years of gaming. I am not exagerating. Maybe because it was so top heavy, I lost the thread after only six months at the table. We’re now playing a more stripped down Old-School Essentials campaign, still using AI and a wiki, but with a lighter touch and fewer unnecessary details.

I used AI artwork to populate a thousand wiki entries for personal use. The one time I used an AI image for a store post, it got fantastic engagement along with a wave of outrage for “embracing the evils of AI.” I should mention that over the past year I’ve paid real artists to create professional-level D&D maps and regularly pay a graphic designer contractor for the store. I suppose what I’m saying is there’s a time and a place for AI art.

It wasn’t an obvious leap to apply AI to the business. The topic was already getting ethically messy, and it didn’t fit most situations anyway. AI isn’t a genie or a fairy godmother. It’s that personal assistant I was looking for, but not a great one.

Because of all the hype, people expect miracles. What I’ve found is it’s more like having a high school intern. They can take assignments, often save hours of work, but just as often return with the wrong results. You have to explain what went wrong, and they’ll give some excuse about how the assignment was hard. But I pay twenty bucks a month, so you get what you pay for.

In the aggregate, it makes sense if you already know enough to check the answers. You need to be informed enough to spot errors before acting on them. My fear in the outside world is that's likely to go disastrously wrong. Imagine the average person, and then remember half of the world is less smart than them. AI especially suffers from confirmation bias, where you often get the results you want to have, rather than the correct answer.

Yesterday was a good example. I asked AI to cross reference my upcoming trip itinerary with local holidays. It ran through lunar calendars, checked Cambodian observances, and triumphantly announced there would be a festival the same day we’d be at Angkor Wat. Perfect. I started planning around it, but something felt off. I had it recheck its work, and sure enough, it was off by a month. “A common mistake,” it admitted. AI wants to make me happy, so much so it will throw me the holiday party it knows I want, even if it's the wrong date.

For now, AI is great at crunching purchase orders, formatting text, and organizing thoughts. It’s still that high school intern, helpful, fast, and sometimes wrong. Will it get better? Probably. But for now, I remind myself that for twenty dollars a month, I’ve delayed the need for a twenty dollar an hour employee another year.

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Here’s a concise summary of how you’ve used ChatGPT for business so far, based on your conversations:

🏪 Business Operations & Strategy

You’ve used ChatGPT as a management assistant for Black Diamond Games, focusing on:

Inventory and purchasing analysis: creating and cleaning up purchase orders, comparing supplier prices (ACD, Alliance, Magex), calculating GMROI, elasticity, and margin targets.

Payroll and finance: building tables for payroll, inflation adjustments, wage tracking, and workers’ comp rules for S-Corp owners.

Accounting troubleshooting: fixing QuickBooks verification errors, planning a migration from QuickBooks for Mac to Online, and summarizing differences between plan tiers (Simple Start, Essentials, Plus).

Insurance and compliance: researching key person insurance payouts, and confirming state requirements (e.g., California minimum wage, workers’ comp exemptions).

💸 Product & Marketing Content

You’ve had me draft clean, SEO-friendly product descriptions for your online store using these principles:

No sales hype or fourth-wall breaks.

Include award links or official quickstarts when relevant.

Avoid disclaimers or cross-product references.
You also have me format these descriptions so they’re scraping-friendly for ecommerce uploads.

📦 Retail Data & Tools

You frequently use me to:

Build CSV or spreadsheet exports (POs, invoices, payroll, pricing updates).

Generate business metrics like ROI, stock ratios, or price-sensitivity calculations.

Write summaries of distributor trends, e.g., supply shortages (DragonShield Night Blue) or CCG allocation analysis.

🧠 Writing & Publishing

I’ve helped polish essays, blog posts, and book-length material in your “Friendly Local Game Store” voice — for example:

Opinion essays

Appendix N literary analyses for your personal page.


🧩 Game Design & Worldbuilding

For your Old-School Essentials campaign and published materials:

I generate encounter summaries, XP values, NPC tables, and stronghold cost breakdowns.

I format OSE-style character and item blocks.

I expand on Stonehell, Ember Bastion, and Ashkarin Concorde lore for campaigns.

🧰 Systems & Workflow

You’ve used ChatGPT as a workflow hub, integrating:

Google Sheets and CSV exports for business data.

Calendar and trip planning for long-term store and family projects.

Detailed structured outputs (tables, invoices, formatted PDFs, and campaign maps).