Dean Mathews: Building Scalable Financial Advice for the Mass Affluent

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 storyThe creation and growth of OnTheClockProduct philosophy: usability, reliability, and UXIntuition, pattern recognition, and the emotional side of entrepreneurshipKey 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 MathewsConnect with Dean Mathews:  Website: https://www.ontheclock.com/ LinedIn: http://linkedin.com/in/dean-mathews-yes | https://www.linkedin.com/company/ontheclock-com Facebook: https://www.facebook.com/ontheclocktimeclock YouTube: https://www.youtube.com/user/OnTheClockTimeClock To get in touch with Gary:Website: https://betterpathtraining.com/LinkedIn: https://www.linkedin.com/in/gsinderbrand/Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.