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The Pivot Chronicles • Part 10

Starting Over (Again): What Would Change With 10 Real Customers

Proof before perfection

Alistair Nicol
September 16, 2025
7 min read

If I had to start over tomorrow and get 10 paying customers in 30 days, almost everything I've built so far would be irrelevant.

Not because it wasn't good, but because it wasn't anchored.

I'd throw out 90% of the code, the architecture, the automation, the roadmap slides. All of it.

And I'd start with conversations.

Real ones.

What I'd Do Differently

I'd open my laptop and make a list of 50 people who might care, not ideal personas, just real operators I know.

Then I'd start reaching out.

Not to sell. To learn.

I'd ask questions like:

"What's the most annoying part of your day?"

"When does that problem show up?"

"What do you do about it now?"

"What have you already tried that didn't work?"

Then I'd shut up and listen.

I wouldn't talk about features, AI, or automation.

I'd look for patterns of pain.

And when I heard the same complaint three times, I'd build the smallest thing possible to fix it, then call those same people back the next day.

That would be version one.

The Realization

If I'm honest, the biggest mistake across every version of PeakOps and Extenure wasn't bad strategy. It was building before proving demand.

We were designing for scale before earning relevance.

We built automation before we built audience.

That's backwards.

If I had to do it again, I'd chase proof before perfection.

I'd care more about a single customer saying "this saved me time" than 100 saying "this looks cool."

The 30-Day Playbook

If I had 30 days and nothing else, it would look like this:

Week 1: Talk to 20 people. Identify 3 repeatable pain points.

Week 2: Build one low-tech solution: a form, a spreadsheet, a workflow. Deliver it manually.

Week 3: Charge for it. Adjust until at least 3 people pay.

Week 4: Automate the parts that hurt the most.

That's it.

No logo. No landing page. No features I can't demo over Zoom.

Just conversation → solution → payment → iteration.

What I Learned

Code doesn't create traction. Conversations do.

You don't need scale; you need proof.

Selling early feels uncomfortable, but it's the only shortcut that works.

If it's not worth paying for manually, it's not worth automating.

Starting over wouldn't mean rebuilding a product.

It would mean rebuilding discipline.

And if I can internalize that lesson, maybe the next version won't need another pivot.

More from The Pivot Chronicles

The Journey Continues

These lessons aren't theoretical. They're being applied right now. Join us as we figure out what actually works.