What Scaling Squire Taught Me About Building Companies That Last

Squire didn't become a leading technology platform because we had a brilliant original idea. Plenty of people had the idea. We became what we are because we survived the moments that kill most companies — and learned the right lessons from each one.

Your First Market Is a Wedge, Not a Ceiling

When we started with barbershops, the instinct was to go broad immediately. But going deep in one vertical first gave us something going broad never would: genuine product-market fit. We understood barbershop workflows at a level no horizontal platform ever could. That depth created word-of-mouth growth no marketing budget could buy.

Go deep first. Go broad later. The depth is what makes the breadth possible.

Culture Is a Product Decision

At Squire, our early team included people who actually went to barbershops — who understood the culture, the conversation, the community. That wasn't an accident. It was a hiring decision that shaped every product decision downstream.

If your team doesn't look like your customers, your product will always feel like it was built by outsiders.

Revenue Is the Best Fundraising Strategy

The moments when Squire was strongest were always the moments when our revenue growth was speaking louder than our pitch deck. Nothing validates your business like customers trusting you with their money.

The Hard Conversations Are the Important Ones

Every week you delay a hard conversation, the problem compounds. I've never once had a hard conversation and wished I'd waited longer to have it.

Build for Decades, Execute in Quarters

A 20-year vision gives you conviction when quarters are tough. Quarterly execution prevents the vision from becoming fantasy. The founders who lose their way are usually the ones who get lost in the vision without execution, or trapped in execution without the vision.

Looking Forward

The convergence of AI, embedded finance, and vertical software is creating the biggest opportunity in small business technology I've seen in my career. The lessons from the last decade are the foundation. The next decade is where we build the cathedral.