Building Technology for Underserved Markets

When we started Squire, people asked why barbershops. Venture investors who hadn't been to a barbershop in years would look at us sideways. "How big is the TAM?" they'd ask, thinking about barbershops as a niche rather than a window into the entire service economy.

Here's what they missed: the best technology markets aren't the ones where incumbents are fighting over sophisticated users. They're the ones where millions of business owners are using pen, paper, and sheer willpower to run their operations.

The Blank Slate Advantage

In a crowded market, you need to be 10x better than the existing solution to get adoption. In an underserved market, you need to be 2x better than nothing. The physics of competition are fundamentally different.

The Cultural Dimension

When we built Squire, we didn't just build scheduling software. We built for the culture of barbershops — where the relationship between barber and client is personal, where cash has been king for generations, where trust is earned face-to-face.

Building for an underserved market isn't just about shipping features. It's about earning the right to serve that community by demonstrating that you understand it.

The Expansion Playbook

Barbershops share DNA with salons, which share DNA with spas, which share DNA with fitness studios, which share DNA with every service business in America. When you build a great operating system for one vertical, the expansion into adjacent verticals is natural.

The TAM question isn't "how many barbershops are there?" It's "how many service businesses exist that are underserved by technology?" The answer is: most of them.

The AI Multiplier

AI makes the underserved market opportunity even larger. Previously, you needed a big team to build and maintain software for each vertical. Now, AI agents can handle the customization. The cost of serving a new vertical drops dramatically.

The opportunity has never been bigger. The technology has never been more capable. And the markets have never been more ready.