Follow Jack, a successful plumber, as he navigates the world of AI phone systems and accounting software. This is what happens when a real small business owner tries to automate his life – spoiler alert: it's messier than a burst pipe.

Jack's Tech Torture Chamber: Episode 1

A Real Plumber's Journey Through the AI Wilderness

SECTION 1: THE SETUP (Or How I Got Roped Into This Mess)

Second Week of January: When My Headache Finally Went Away

Look, I'm Jack. I'm 37, I own a plumbing company, and until last week, I thought "AI" stood for "Aggravating Idiots" – which, coincidentally, is what I call half my customers when they try to explain what's wrong with their toilet over the phone.

Let me back up. Twelve years ago, when I was a cocky 25-year-old with a journeyman's license and more ambition than sense, I started Jack's Plumbing. Not "Jack T.'s Premium Plumbing Solutions" or some other fancy crap – just Jack's Plumbing. Because when your toilet's backing up at 2 AM, you don't want premium solutions, you want Jack.

Fast forward to today: I've got 12 employees (13 if you count me, which I do because I sign the checks), 9 vehicles that break down in perfect rotation to keep me humble, and a shop I built with my own two hands and a construction loan that still gives me nightmares. I run six 2-man crews, and I float between them like some kind of plumbing superhero – except instead of a cape, I wear Carhartt pants with suspicious stains.

Here's the thing nobody tells you about being successful: the more money you make, the less actual plumbing you do. I pay my guys 33% more than the average plumber around here – not because I'm generous (okay, maybe a little), but because it means I can trust them to handle jobs without me babysitting. This frees me up to do the "fun" stuff: scheduling, payroll, bookkeeping, ordering parts, answering phones, and questioning every life decision that led me to own a business instead of just showing up, fixing pipes, and going home.

Which brings me to my neighbor Bert.

Bert runs some kind of business efficiency consulting company. Honestly, I'm still not 100% sure what he actually does, but he wears khakis to work and uses words like "synergy" and "optimization" without irony, so I assume he's doing okay. We've been neighbors for six years, and we've got that perfect friendship where we drink beer in his driveway every Friday and solve the world's problems without actually doing anything about them.

Three Fridays ago – right before New Year's – I was complaining (shocking, I know) about how I spend half my day answering the phone. "Jack, I got a clogged drain." "Jack, my water heater's making a noise." "Jack, I flushed my kid's toy dinosaur and now the toilet sounds like Jurassic Park."

Bert, three beers deep and feeling helpful, says: "Man, you need an AI phone answering service. I've got like fifteen free trials sitting in my email right now. Companies send them to me all the time hoping I'll recommend them to clients."

"AI can answer phones?" I asked, genuinely confused.

"Dude, AI can do everything now. It's 2025. We're basically living in the future, except we still can't get flying cars because everyone's too busy teaching robots to write poetry."

And that's how I got roped into this. Bert offered to let me test-drive all these software trials he gets, and I figured, why not? Worst case scenario, I waste some time. Best case scenario, I get my life back and stop dreaming about phones ringing.

We agreed I'd start the first week of January. Fresh year, fresh start, all that motivational poster garbage.

Except the first week of January, I had the mother of all headaches. Not a hangover (okay, maybe partially a hangover from New Year's), but one of those tension headaches that makes you wonder if this is it, if this is how you go out – death by small business ownership and too much screen time.

So I pushed it to the second week. Bert understood. He gets migraines. We're both falling apart in our late thirties, just in different ways.

Monday, January 8th: The Day I Turned On Two Robots At Once (Because I'm An Idiot)

Here's where I made my first mistake. Bert had set me up with two trials: the AI phone answering service AND QuickBooks Online with all their fancy AI features. His plan was for me to test them one at a time, like a rational human being.

But it's January. It's slow. Post-holiday, everyone's broke, and nobody wants to think about their plumbing until something actually breaks. I figured, "How hard can it be to test two things at once?"

Narrator voice: It was harder than he thought.

7:00 AM - AI Receptionist Goes Live:

The service Bert set me up with is called AI Receptionist (not the real name, but close enough – they all have names like this). According to their website, it's got a 4.2 out of 5-star rating, which sounds great until you realize that's like saying "only 16% of the time does it completely fail at its one job."

Setup was supposed to take "10 minutes." It took 47. Not because it was complicated, but because I had to teach this AI what a "sump pump" was. Apparently, the default vocabulary includes "meeting," "appointment," and "conference call," but not "my basement's flooding and I'm standing in three inches of water."

The system works like this: Customer calls, AI answers with a voice that sounds like a very polite robot who's had exactly one cup of coffee. It asks what they need, tries to understand them, and either schedules an appointment or takes a message. In theory.

8:30 AM - QuickBooks Gets Access to My Life:

While I'm waiting for the first call to test the AI receptionist, I'm setting up QuickBooks. This is the part where it wants to connect to my bank account. This makes me nervous. I've seen enough movies to know that connecting things to other things is how Skynet starts.

But I do it. And then something magical happens: It imports three months of transactions automatically. Every purchase, every deposit, every time I bought coffee at 6 AM because I'm not a morning person and caffeine is the only thing between me and a workplace incident.

Background on my current bookkeeping system:

I have a filing cabinet. In that cabinet are folders labeled by month. In those folders are receipts, invoices, and various papers that may or may not be important. Once a month, I spend an entire Saturday entering everything into a spreadsheet that I then email to my accountant, who probably drinks heavily after dealing with me.

This system has worked for 12 years. It's terrible, but it's MY terrible system, and I understand it.

But now QuickBooks is asking me to "categorize" everything. There are like 50 categories. "Meals & Entertainment." "Auto & Truck Expenses." "Office Supplies." "Existential Dread" (okay, I made that last one up, but it should be an option).

I'm about to give up when I notice a button that says "Let AI Categorize."

I click it.

And I watch, in real-time, as this robot goes through 300 transactions and sorts them into categories. It puts gas station purchases under "Fuel." It puts Home Depot runs under "Materials." It even catches that my "subscription" to a trade magazine should be "Professional Development" and not "Office Supplies."

It gets about 85% of them right. The other 15% are weird – it thought my payment to "AAA Plumbing Supply" was "Advertising" instead of "Materials," probably because of the "AAA" part. But still. 85% right means I only have to fix 45 transactions instead of 300.

I'm starting to feel things. Positive things. About software.

9:47 AM - First Call:

I'm still fixing QuickBooks categories when my phone buzzes. It's the monitoring app for the AI receptionist. Someone's calling.

I stop what I'm doing and listen like a nervous parent on their kid's first day of school.

AI: "Thank you for calling Jack's Plumbing. How can I help you today?"

Customer: "Yeah, my toilet's running."

AI: "I understand you need assistance with a running toilet. Would you like to schedule an appointment?"

Customer: "Yeah, how soon can you get here?"

AI: "I have availability today at 10 AM, 1 PM, or 3 PM. Which works best for you?"

Customer: "10 AM."

AI: "Perfect. I've scheduled you for 10 AM today. Can I have your name and address?"

Holy crap. It worked. It actually worked. I didn't have to stop what I was doing, answer the phone, and have the same conversation I've had 10,000 times.

I go back to QuickBooks feeling like I'm living in the future.

Tuesday, January 9th: When Things Start Getting Weird

Morning:

I wake up to an email from QuickBooks. Subject line: "Your Daily Business Snapshot."

I open it expecting some generic "you spent money yesterday" message, but instead I get this:

"Good morning, Jack. Yesterday you had 3 transactions totaling $847.32. Your fuel expenses are tracking 18% higher than last month. You have $12,450 in outstanding invoices. Two invoices are overdue by more than 30 days."

Wait. What?

I have overdue invoices? I mean, I knew I had invoices out there, but I didn't know they were OVERDUE overdue. I usually just... wait for people to pay me and hope for the best.

I click through to QuickBooks and sure enough, there they are. Two invoices from December that I completely forgot about. One for $850, one for $1,200.

The AI has a button that says "Send Reminder." I click it. It generates a polite email automatically: "Hi [Customer Name], just a friendly reminder that invoice #[whatever] is now 34 days past due. Please let me know if you have any questions!"

I send both. Within an hour, one customer replies apologizing and pays immediately. The other one I have to call, but still – that's $2,050 I didn't even know I was missing.

This robot just made me two grand before lunch.

Afternoon - The AI Receptionist Has Its First Crisis:

Call comes in at 2:15 PM. I'm at a job site helping one of my crews with a tricky shower valve replacement.

AI: "Thank you for calling Jack's Plumbing. How can I help you today?"

Customer: "My water heater's leaking everywhere and it's making a hissing sound like an angry snake."

AI: "I understand you're experiencing a water heater issue. Would you like to schedule—"

Customer: "No, I need someone NOW. Like right now. There's water everywhere!"

AI: "I have availability today at—"

Customer: "ARE YOU EVEN LISTENING TO ME?"

AI: "I apologize for any confusion. Let me connect you with someone who can help."

And then it transfers the call to me. Which would be fine, except I'm currently elbow-deep in a shower wall, and my phone is in my truck. By the time I get to it, the customer has hung up and probably called my competitor.

Mental note: Need to program emergency keywords better.

Wednesday, January 10th: I Spend Three Hours Teaching Robots

I'm supposed to be bidding a commercial job today, but instead I'm at my desk programming the AI receptionist with "emergency keywords."

Words like "flooding," "burst," "emergency," "NOW," and "angry snake hissing sound" are now supposed to trigger an immediate transfer to my cell phone.

While I'm doing this, QuickBooks pops up another message:

"You've categorized 45 transactions this week. Based on your patterns, I've automatically categorized 12 new transactions. Would you like to review them?"

I click through. It got 11 out of 12 right. The one it got wrong was a $200 charge to "Johnson Supply" that it marked as "Materials" but was actually a personal purchase I accidentally put on the business card (a new drill for my home workshop – don't tell my accountant).

I fix it, and QuickBooks says: "Got it. I'll remember that Johnson Supply purchases should be reviewed before auto-categorizing."

The robot is learning. This is either really cool or the beginning of a sci-fi horror movie.

Evening:

I test the emergency keyword system by having Bert call and say "my basement is flooding."

It works! Transfers immediately to my cell.

Then I have him call and say "I'd like to schedule something for now or maybe next week."

It also transfers to my cell because of the word "now."

Back to programming.

Thursday, January 11th: The Plot Thickens

Stay tuned for Episode 2, where Jack discovers that AI can also screw up in ways he never imagined possible, and QuickBooks starts giving him business advice that's either brilliant or completely insane...

The Bottom Line (So Far)

Three days in, and I'm already questioning everything I thought I knew about running a business. These robots are making me money, saving me time, and occasionally driving me completely insane.

If you're a small business owner thinking about dipping your toes into the AI waters, just remember: it's not magic, it's not perfect, and it definitely doesn't understand plumbing emergencies right out of the box.

But it might just change your life anyway.

Next episode: What happens when the AI receptionist meets its first truly angry customer, and QuickBooks decides to give Jack unsolicited business advice at 6 AM.