Advice for First-Time Founders

If I could go back and talk to myself on day one of starting Squire, here's what I'd say.

Pick a Market You're Willing to Obsess Over

You're going to spend years — maybe decades — working in this market. Make sure it's one you find genuinely fascinating. The founders who build the biggest companies are the ones who can't stop thinking about their customers' problems, even on weekends.

For me, the barbershop industry was that market. The culture, the community, the untapped potential — it captivated me from day one and still does today.

Revenue Solves Most Problems

In the early days, it's tempting to focus on building the perfect product, raising the perfect round, or hiring the perfect team. But nothing validates your business like revenue. Find a way to charge customers as early as possible. Real customers paying real money will teach you more than any advisor or investor ever could.

Fundraising Is a Means, Not an End

Raising venture capital is not a milestone — it's a tool. The goal is to build a great business, not to raise money. I've seen too many founders treat fundraising as validation. The real validation comes from customers who love your product and a business model that works.

Move Fast, but Don't Cut Corners

Speed matters in a startup. But there's a difference between moving fast and being sloppy. Build quickly, ship often, but maintain high standards for the things that matter most — customer experience, reliability, and trust.

Take Care of Yourself

Burnout is real, and it's the enemy of good decision-making. The best founders I know take their physical and mental health seriously. Exercise, sleep, relationships outside of work — these aren't luxuries, they're requirements.

Find Your People

Entrepreneurship is lonely. Find a community of founders who understand what you're going through. The best advice I've ever received has come from other founders who were a few steps ahead of me on the same path.