Episode Details

About Dean Mathews: Dean Mathews is the founder and CEO of OnTheClock, a time‑tracking and payroll platform serving over 18,000 businesses with tools for employee time tracking, scheduling, payroll, and PTO. A self‑taught developer who started by building custom software for local companies, Dean grew OnTheClock from a kitchen‑table side project into a scalable SMB solution known for being easy, reliable, and intuitive to use. Today, he leads a growing team focused on practical product design, strong culture, and helping small businesses run more efficiently while building happier, more productive teams.

In this episode, Gary and Dean Mathews discuss:

• Dean’s entrepreneurial and technical origin story
• The creation and growth of OnTheClock
• Product philosophy: usability, reliability, and UX
• Intuition, pattern recognition, and the emotional side of entrepreneurship

Key Takeaways:

• Some of the most valuable business lessons don’t come from classrooms or formal training. They come from making decisions without a safety net and owning the outcome.
• Responsibility and real consequences change how you think—and when the stakes are real, learning accelerates fast.
• Confidence grows through repetition, not perfection. Getting things wrong is often part of getting better.
• Leadership isn’t about having all the answers. It’s about being willing to learn, adapt, and move forward anyway.

"There's always a fear element…But fear isn't the thing, it's the courage that matters." — Dean Mathews

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