Lessons from Building Squire

Building Squire has been the most challenging and rewarding experience of my life. From the earliest days of knocking on barbershop doors to today, leading a global technology company, the journey has taught me lessons that no business school ever could.

Start with the Problem, Not the Solution

When we started Squire, we didn't begin with a grand vision for a technology platform. We started by spending time in barbershops, talking to owners and barbers, understanding their daily frustrations. The technology came second — the empathy came first.

Too many founders fall in love with their solution before they truly understand the problem. The best products are built by people who are obsessed with the problem, not the technology.

Resilience Is Everything

There were moments in the early days when it felt like everything was working against us. Fundraising rejections. Product setbacks. Customers who didn't believe technology could help their business. And then, of course, a global pandemic that shut down every barbershop in the country overnight.

Each of those moments was a test of resilience. The pandemic, in particular, forced us to rethink our entire approach. We built new tools to help barbershops navigate health and safety requirements, manage capacity limits, and communicate with customers. We didn't just survive — we came out stronger.

Your Team Is Your Company

The single most important thing I've learned is that your team is everything. The right people will figure out the right strategy, build the right product, and solve the right problems. Hiring, culture, and leadership aren't HR functions — they're the core of building a company.

Stay Close to Your Customer

Even as Squire has grown, I make it a point to regularly visit barbershops, talk to owners, and use our own product. It's easy to get disconnected from your customer as a company scales. The founders who stay close to the ground truth build better products and make better decisions.

The Journey Is the Reward

Building a company is not a destination — it's a continuous journey. Every milestone reveals new challenges. Every success creates new responsibilities. The key is to find joy in the process of building, not just in the outcomes.