Dean Mathews of On The Clock: How He Bootstrapped from a Kitchen Table Startup to a $10M SaaS Powerhouse with 280K+ Users—Built a People-First Culture and a Self-Sustaining Business That Runs Without Him. (Episode 683 - Dean Mathews)

In this episode of Grow a Small Business, host Troy Trewin interviews Dean Mathews, the founder of On The Clock. Dean shares his evolution from a solo software developer in 2004 to leading a team of 23 professionals, supporting 170,000 to 280,000 active users. Originally launched as a time-tracking app, On The Clock has expanded to include employee scheduling and payroll services, with ambitious goals of reaching $10 million in revenue and one million monthly active users. Dean discusses the critical role of consistency, hiring the right talent, and leveraging tools like Asana for effective project management. He also emphasizes the importance of understanding customer needs and fostering a culture that prioritizes growth and team development. Other Resources:

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Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice.

And a snapshot of the final five Grow A Small Business Questions:

1. What do you think is the hardest thing in growing a small business? According to Dean Mathews, the hardest thing in growing a small business is shifting from doing everything yourself to empowering others by building systems and trusting your team. He highlights the importance of moving from working in the business to working on the business, emphasizing that true growth comes from hiring the right people, clearly defining roles, and creating an operating structure that allows others to thrive. You can't scale alone, and recognizing that earlier can make a significant difference.
2. What's your favorite business book that has helped you the most? Dean Mathews' favorite business book that has helped him the most is Scaling People by Claire Hughes Johnson. He found it especially valuable because it offers practical frameworks and structures for growing teams and building an internal operating system. The book resonated with him as it closely aligned with the challenges he faced while scaling OnTheClock, particularly around leadership, processes, and team development. He even conducted a book club at work based on it, applying its lessons to enhance how his company operates.
3. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Dean Mathews recommends several great podcasts and online learning resources to help grow a small business, especially in the SaaS space. His top pick is the SaaStr Podcast, which features insights from successful SaaS founders and is packed with growth strategies. He also expressed strong interest in exploring content by Alex Hormozi, particularly his books $100M Offers and $100M Leads, and his podcast focused on data-driven business scaling. Additionally, Built to Sell Radio by John Warrillow was recommended for its focus on recurring revenue and building sellable businesses, while Nathan Latka's Podcast was noted for its sharp focus on SaaS metrics like ARR, MRR, CAC, and churn—making it a valuable listen for any growth-minded founder.
4. What tool or resource would you recommend to grow a small business? Dean Mathews recommends using a project management tool like Asana to grow a small business, as it helps teams stay organized, track progress, and manage both projects and processes effectively. He believes every business boils down to three core elements—people, projects, and processes—and Asana helps align them in a structured way. Additionally, he highlights creating an internal operating system (built in tools like Google Slides), which outlines company values, goals, job roles, meeting structures, and key metrics. Together, these tools support scalable growth and team alignment.
5. What advice would you give yourself on day one of starting out in business? Dean Mathews' advice to himself on day one of starting out in business would be to "buckle in, you're in for a ride" and to understand early on that scaling a business is all about people. He emphasizes that success doesn't come from doing everything yourself, but from hiring the right people, trusting them, and building systems that empower them to thrive. He reflects that if he had learned earlier how to let go of control and focus on developing others, his business could have grown even faster. Surrounding yourself with people who are smarter than you in their areas is key to building something truly sustainable.

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Quotable quotes from our special Grow A Small Business podcast guest:

Trusting others with your vision is the first step to real growth — Dean Mathews A strong culture starts with clearly defined and lived values — Dean Mathews Leadership is less about control and more about enabling success — Dean Mathews