$100K. That's what I "owed" my boss after I burned six figures on a quoting tool that never launched.

It became a punchline. Every new idea: "What's this—another $100K masterpiece?" Every ask for help: "Nope. Work with what you've got. I'll knock it off your tab."

Six months rebuilding trust and asking myself one question: How the hell did I miss that?

The Mistake

One seamless quoting engine that connected all our systems. That was the idea.

It didn't. It couldn't. It was built for an operation we hadn't grown into yet. Our data was messy. Roles weren't clear. Decisions changed weekly. The inputs never settled long enough to be automated. But we still bought it. Still built it. Never launched.

Our internal teams said they could make it work. The vendor promised they'd done it before. I knew what the customer wanted. I assumed we'd pull it off.

That assumption cost me.

Had I mapped the whole thing—data in, logic, failure states, outputs—I would've seen it was doomed. I could've killed it before we signed the contract. Saved the money. Saved the hit to credibility. Saved myself from being the punchline in every meeting for six months.

But I didn't. So I learned.

Fast Forward: New Business, Same Pattern

Now I'm launching a franchise. And I'm back in the deep end eyes wide open.

Vendors everywhere—marketing platforms, CRMs, field ops software, payment tools. Each one owns a sliver of the customer journey and adds variables I don't control.

I've got 10+ phone numbers floating through the system. Three platforms sending texts. Owners handing out personal cells as the business line. It's chaos—right in front of the customer.

I keep trying to map the full journey, first click to final invoice, but it's foggy. Every vendor knows their part. No one can explain the full ride.

And again, that job falls to me.

The Purgatory Phase

This is the part I hate the most. I want to build. I want clean data and smart automation. But I don't understand it yet and I can't fake my way into clarity.

I reach out to other owners hoping for a roadmap. Instead, I get shoulder shrugs and tool stacks.

"We just use what they gave us." "I built my own CRM." "Steve's doing something—ask him." "I have a VA."

Okay—but why? What were you solving for? What wasn't working? What did you learn?

Nobody seems to want to talk about that part. And maybe I'm the weirdo for asking.

I Need to Understand

I've always been like this.

In college, I took automotive classes—not to become a mechanic, but because I hated not knowing how engines worked. I'd buy repair manuals and teardown videos just to make sense of the machine.

This feels the same. I'm surrounded by a machine I don't yet understand, and it's driving me nuts. I even started a Teams group to talk shop with other new owners… but I think I'm just stressing them out. One guy muted the chat.

Maybe I'm overthinking it. Maybe most people are fine just running the playbook and fixing the leaks later.

But I'm not. I want to scale this thing. I want to build something real. And I don't trust systems I can't explain.

Where I'm At

People keep telling me: "Just get in. Do every job for a month. You'll learn fast."

I believe them. But I also know how easily bad systems become permanent ones. So I'm trying to live in both worlds, doing the work and watching the machine.

I don't want to get fancy too early. But I don't want to ignore red flags either.

Once I understand this thing, front to back, I can finally:

But today? I can't explain it.

And if one person, you, can't explain the system end to end… you don't have a system. You have a mess. You just haven't found it yet.