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How to Build a Business That Doesn't Depend on You | Dean Mathews
Most entrepreneurs start their business doing everything themselves.
Sales.
Customer service.
Accounting.
Marketing.
Operations.
But eventually that becomes the very thing holding the business back.
In this episode of Small Business Pivots, Michael D. Morrison sits down with entrepreneur, software founder, and CEO Dean Mathews, creator of OnTheClock, to discuss the leadership shifts required to grow beyond yourself and build a business that can thrive without depending on the owner every day.
Dean shares lessons learned from building a software company serving over 16,000 businesses while growing a team of nearly 30 employees. He explains why hiring too late is one of the biggest mistakes entrepreneurs make, how to build a positive company culture, why leaders must stop micromanaging, and how empowering employees creates stronger businesses.
They also discuss leadership development, delegation, company culture, payroll, employee management, hiring strategies, autonomy, business systems, and why humility may be one of the greatest leadership traits an entrepreneur can develop.
In this episode you'll discover:
• Why doing everything yourself limits business growth
• When it's time to hire your first employee
• How to stop becoming the bottleneck
• The importance of clear roles and job descriptions
• Why autonomy creates stronger employees
• The "Hire Slow, Fire Fast" philosophy
• Building company culture intentionally
• Leadership lessons from growing a software company
• How payroll, scheduling, and HR systems improve operations
• Why humility makes stronger leaders
If you're a business owner trying to scale your company, develop better leaders, build stronger systems, or simply get your life back, this episode is packed with practical advice you can implement immediately.
About Dean Mathews
Dean Mathews is the founder and CEO of OnTheClock, a workforce management platform helping thousands of businesses simplify employee time tracking, scheduling, payroll, and HR management. A lifelong entrepreneur and software developer, Dean is passionate about leadership, business systems, and helping small businesses build companies that scale.
About Small Business Pivots
Hosted by Michael D. Morrison, Small Business Pivots features entrepreneurs, business leaders, authors, and experts sharing the pivots, systems, and strategies that help business owners get unstuck and grow.
🏆 Ranked among the Top 10% of podcasts globally by Listen Notes.
Support the show
1. Want professional business coaching with the podcast host, Michael D. Morrison?
https://www.michaeldmorrison.com
2. Want to set up a FREE business consultation with the podcast host, Michael D. Morrison?
https://www.michaeldmorrison.com/consultation
Connect and follow the podcast host, Michael D. Morrison to learn how to grow a successful business :
- LinkedIn: https://www.linkedin.com/in/michaeldmorrisonokc/
- YouTube: https://www.youtube.com/@michaeldmorrisonokc
- Facebook: https://www.facebook.com/MichaelDMorrisonOKC
- Instagram: https://www.instagram.com/michaeldmorrisonokc/
- TikTok: https://www.tiktok.com/@michaeldmorrisonokc
Email the podcast host, Michael D. Morrison: [email protected]
View all episodes
By Michael D. MorrisonMost entrepreneurs start their business doing everything themselves.
Sales.
Customer service.
Accounting.
Marketing.
Operations.
But eventually that becomes the very thing holding the business back.
In this episode of Small Business Pivots, Michael D. Morrison sits down with entrepreneur, software founder, and CEO Dean Mathews, creator of OnTheClock, to discuss the leadership shifts required to grow beyond yourself and build a business that can thrive without depending on the owner every day.
Dean shares lessons learned from building a software company serving over 16,000 businesses while growing a team of nearly 30 employees. He explains why hiring too late is one of the biggest mistakes entrepreneurs make, how to build a positive company culture, why leaders must stop micromanaging, and how empowering employees creates stronger businesses.
They also discuss leadership development, delegation, company culture, payroll, employee management, hiring strategies, autonomy, business systems, and why humility may be one of the greatest leadership traits an entrepreneur can develop.
In this episode you'll discover:
• Why doing everything yourself limits business growth
• When it's time to hire your first employee
• How to stop becoming the bottleneck
• The importance of clear roles and job descriptions
• Why autonomy creates stronger employees
• The "Hire Slow, Fire Fast" philosophy
• Building company culture intentionally
• Leadership lessons from growing a software company
• How payroll, scheduling, and HR systems improve operations
• Why humility makes stronger leaders
If you're a business owner trying to scale your company, develop better leaders, build stronger systems, or simply get your life back, this episode is packed with practical advice you can implement immediately.
About Dean Mathews
Dean Mathews is the founder and CEO of OnTheClock, a workforce management platform helping thousands of businesses simplify employee time tracking, scheduling, payroll, and HR management. A lifelong entrepreneur and software developer, Dean is passionate about leadership, business systems, and helping small businesses build companies that scale.
About Small Business Pivots
Hosted by Michael D. Morrison, Small Business Pivots features entrepreneurs, business leaders, authors, and experts sharing the pivots, systems, and strategies that help business owners get unstuck and grow.
🏆 Ranked among the Top 10% of podcasts globally by Listen Notes.
Support the show
1. Want professional business coaching with the podcast host, Michael D. Morrison?
https://www.michaeldmorrison.com
2. Want to set up a FREE business consultation with the podcast host, Michael D. Morrison?
https://www.michaeldmorrison.com/consultation
Connect and follow the podcast host, Michael D. Morrison to learn how to grow a successful business :
- LinkedIn: https://www.linkedin.com/in/michaeldmorrisonokc/
- YouTube: https://www.youtube.com/@michaeldmorrisonokc
- Facebook: https://www.facebook.com/MichaelDMorrisonOKC
- Instagram: https://www.instagram.com/michaeldmorrisonokc/
- TikTok: https://www.tiktok.com/@michaeldmorrisonokc
Email the podcast host, Michael D. Morrison: [email protected]