Still Figuring Positioning, Already Finding Time-Taxes

I'm building an inventory system on top of Square for a pet shop owner.

Last week, I built a resume analyzer for a problem the YMCA is having.

Two completely different problems. Two completely different businesses. Both small businesses who have heard of "AI automation" but had no idea how it could help.

And now I'm staring at the classic entrepreneur's dilemma. What the hell am I actually selling?

I didn't have to battle that with my past business. It was clear that we sold catering services. Sure we had to find what packages worked and what not, but that wasn't too difficult.

Now I'm like am I an ai automation agency? A one time system set up guy? A monthly partner who partners with with businesses to build systems? A consultant who gives opinions and disappears?

On top of that I'm thinking about a niche within those. I just want to help small business owners save time and I know I have the ability to do that. But how do I position myself to let them know that?

I don't know yet. And that's driving me crazy.

After I finish the inventory system build do I go around trying to sell "solving your inventory time-suck" or do I say "hey, we automate business processes to save you time. Here's an example of this inventory system that we built to save this Pet Shop 10 hours per week"

What Business Owners Actually Care About

But here's what I'm learning from talking to actual entrepreneurs:

They wont care about my positioning crisis. They care about their problems.

The pet store guy didn't wake up thinking "I need AI automation." He woke up thinking "This weekly inventory count is killing me." Halfway through our conversation, he realized how much time he was hemorrhaging on manual stock management.

These business owners are too busy fighting fires to think about the systems causing the fires (that was the thesis behind the start of this business)

My thinking is many small business owners ($500K to $10M revenue) are trapped in operational quicksand. They're growing fast enough that manual processes are breaking, but not big enough to hire dedicated system optimizers.

My Own Time-Tax Story

They're doing what I used to do when running Tuckedito. I made this whole custom excel report for inventory and ordering. I was running the report weekly. It took me about over an hour to run. About a year in I realized I could make it much more efficient, but I waited for an entire year. Because I "didn't have time" to fix it.

Finally I adjusted it and post adjustment it took 10 minutes for me to run.

Lets do the math on that:

52 weeks × 1 hour = 52 hours of waste Time to fix it = 5 hours

Net savings = 47 hours at $50/hour = $2,350 per year

And that's just one broken process.

The Real Pattern Emerges

So here's how I'm thinking about positioning now:

Forget the business model for a minute, and focus on the pattern.

I'm not the "inventory guy" or the "resume guy." I'm the person who helps entrepreneurs spot the expensive time-sucks that they have normalized. The processes they've accepted as "just how things work." Then fix those problems.

The positioning writes itself: I find the hidden time-tax in your business and eliminate it.

Whether that becomes productized software, monthly automation-as-a-service, or project-based consulting, honestly, I guess I'll let the market decide. Right now I'm building proof-of-concepts for free because each one teaches me something about what people actually value.

The resume analyzer? Pure time-savings system.

The inventory system? Time-savings + accuracy plus + enablement.

Different tools, same core value: Getting hours of your life back.

The Pattern Reveals Itself

But I think there's something deeper happening here. I'm realizing that positioning isn't just about how customers see you, it's about what problems you're naturally drawn to solve. I keep gravitating toward the pain points that business owners don't even realize they have.

Another conversation this week reinforced the pattern. An appraiser told me about their biggest project ever, 5,000 items, 2,000 pickup trucks. "We have dudes writing up the same thing for every pickup truck every time," he said. "Ford F-150, XLT, CrewCab, pickup truck, bed, tires, diesel engine."

He could rattle off equipment descriptions from memory. But they still had people typing the same information over and over, sending it to data entry, fixing errors, reformatting everything to match their "old school way."

"I stare at hundreds of pieces of paper," he said. "And I would like to stare at less paper."

The pattern is everywhere.

Small businesses need dedicated systems people. They can't afford dedicated systems people. So they normalize the inefficiencies until someone like me shows up and says "What if you didn't have to do that manually anymore?"

I just need to figure out away to get the conversations. I feel like (and this is just a feeling) that most people think initially “no I don’t need any help”, but if you could serve them up something immediately they would pay for it.

So I battle, should I be ignoring those people and only looking for small business owners actively looking to solve their problem? And If so, how do I find these ones.

I know the pet store owner doesn't need AI automation. He needs his weekly inventory nightmare to disappear. The appraiser doesn't need technology, he needs to stop retyping the same truck specs. They'll pay for the solution, not the technology, but the technology is what gets the solution.

Maybe the positioning question is backwards.

Instead of asking "How should I position myself?" maybe I should ask "What expensive position am I replacing?"

I'm not building software. I'm not selling automation. I'm selling the peace of mind that comes from knowing your business systems actually work for you instead of against you.

The positioning is somewhere. I just need to get a way to articulate that clearly.

Thanks for reading,

James