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INTERVIEW | Make Money by Learning Before You Earn with Dean Mathews
Dean Mathews is the founder and CEO of OnTheClock, a workforce management platform that helps small businesses simplify employee time tracking, scheduling, payroll, and HR. Serving more than 16,000 businesses and 160,000 employees, Dean has built a thriving SaaS company by combining technical expertise with relentless curiosity. In this episode, he shares how repairing lawnmowers as a teenager led to building a successful software company—and why learning from great business owners was the foundation of his entrepreneurial journey.
On this episode we talk about:
How Dean went from repairing lawnmowers as a teenager to building a successful SaaS business
Why working alongside experienced entrepreneurs can be more valuable than earning a degree
The "kitchen table" moment that inspired the creation of OnTheClock
How SEO, word-of-mouth referrals, and customer-first product development fueled long-term growth
Why every SaaS founder is rethinking the future of business in the age of AI
Top 3 Takeaways
Prioritize learning over earning early in your career by working closely with people who have already built what you aspire to create.
Great businesses often begin by solving a real customer problem that others consistently complain about.
Long-term success comes from building products customers genuinely love enough to recommend to others.
Notable Quotes
"The real education begins when you get on the street in business."
"Learn. Figure out how to serve people, how to serve customers, provide something of value."
"When your customers do it for you, that's invaluable."
Connect with Dean Mathews:
LinkedIn: https://www.linkedin.com/in/dean-mathews-yes/
Other: https://www.ontheclock.com/
A Word from Our Sponsors:
- Visit DrinkAG1.com/TMM to get a free AG1 Travel Case with 7 free AG1Travel Packs in your Welcome Kit with your first AG1 subscription order while supplies last.
- Go to Leesa.com for 25% OFF select mattresses (through July 26, 2026) PLUS get an extra $50 off with promo code TMM, exclusive for my listeners
- To learn more about Mode Mobile and its investor community, go tohttps://invest.modemobile.com/travismakesmoney
Learn more about your ad choices. Visit megaphone.fm/adchoices
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By Travis Chappell
4.3
384384 ratings
Dean Mathews is the founder and CEO of OnTheClock, a workforce management platform that helps small businesses simplify employee time tracking, scheduling, payroll, and HR. Serving more than 16,000 businesses and 160,000 employees, Dean has built a thriving SaaS company by combining technical expertise with relentless curiosity. In this episode, he shares how repairing lawnmowers as a teenager led to building a successful software company—and why learning from great business owners was the foundation of his entrepreneurial journey.
On this episode we talk about:
How Dean went from repairing lawnmowers as a teenager to building a successful SaaS business
Why working alongside experienced entrepreneurs can be more valuable than earning a degree
The "kitchen table" moment that inspired the creation of OnTheClock
How SEO, word-of-mouth referrals, and customer-first product development fueled long-term growth
Why every SaaS founder is rethinking the future of business in the age of AI
Top 3 Takeaways
Prioritize learning over earning early in your career by working closely with people who have already built what you aspire to create.
Great businesses often begin by solving a real customer problem that others consistently complain about.
Long-term success comes from building products customers genuinely love enough to recommend to others.
Notable Quotes
"The real education begins when you get on the street in business."
"Learn. Figure out how to serve people, how to serve customers, provide something of value."
"When your customers do it for you, that's invaluable."
Connect with Dean Mathews:
LinkedIn: https://www.linkedin.com/in/dean-mathews-yes/
Other: https://www.ontheclock.com/
A Word from Our Sponsors:
- Visit DrinkAG1.com/TMM to get a free AG1 Travel Case with 7 free AG1Travel Packs in your Welcome Kit with your first AG1 subscription order while supplies last.
- Go to Leesa.com for 25% OFF select mattresses (through July 26, 2026) PLUS get an extra $50 off with promo code TMM, exclusive for my listeners
- To learn more about Mode Mobile and its investor community, go tohttps://invest.modemobile.com/travismakesmoney
Learn more about your ad choices. Visit megaphone.fm/adchoices
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