Some entrepreneurs start businesses to make money.
Others start businesses because they want freedom.
For Dean Mathews, the motivation was something deeper.
From an early age, Dean had an entrepreneurial spirit. Whether he was repairing lawnmowers as a teenager or teaching himself software development, he always knew he wanted to create something meaningful. Looking back, he now realizes that the goal was never simply building a business. It was building something that would outlast him and positively impact the lives of others.
That mindset became the foundation for On The Clock.
From the Kitchen Table to 16,000 Customers
The story of On The Clock began in late 2003.
While reading accounting and small-business forums one evening, Dean noticed a recurring problem. Business owners and accountants were searching for a better way to track employee time for payroll.
Rather than waiting for someone else to solve it, he decided to build the solution himself.
Within a few months, the first version of On The Clock was launched.
At the time, it was only one of several projects Dean was running. For nearly a decade, the software remained a side business while he continued consulting and developing custom software for clients.
Over time, however, one thing became clear.
Customers kept asking for more.
The product kept growing.
And the opportunity became impossible to ignore.
Eventually Dean made the decision to focus entirely on On The Clock, setting the stage for the company’s future growth.
The Mindset Shift That Changed Everything
One of the most powerful moments in the conversation centered around a realization many entrepreneurs eventually face.
For years, Dean intentionally avoided building a team.
After experiencing several unhealthy workplace cultures while consulting, he convinced himself that managing employees simply was not worth the trouble.
That mindset worked for a while.
The business generated income and provided flexibility.
But it also created a ceiling.
Dean eventually realized he had built a lifestyle business rather than a scalable company.
Everything depended on him.
Customer support requests piled up. Growth slowed. Opportunities became harder to pursue.
That is when one quote changed everything:
“If you want to go fast, go alone. If you want to go far, go together.”
Once Dean embraced the idea that growth required people, everything accelerated.
The company hired its first employee.
Then another.
Today, On The Clock has a team of 28 people working together toward a shared vision.
Building Culture on Purpose
Many business owners talk about culture.
Far fewer build it intentionally.
Dean knew from the beginning that he wanted something different from the unhealthy environments he had witnessed earlier in his career.
Before building a team, he began documenting the characteristics he wanted the company to embody. Those ideas eventually evolved into the company’s core values.
Rather than treating values as marketing language, Dean uses them as hiring criteria and leadership standards.
Every new employee is evaluated against those values.
Every leader is expected to model them.
And every team member is regularly reviewed on how well they live them out.
One lesson stood out throughout the discussion:
Culture is not what is written on the wall.
Culture is what leaders consistently demonstrate.
If leaders fail to embody the values they promote, employees notice immediately.
The result is confusion, distrust, and inconsistency.
Strong cultures begin with leadership.
Why Delegation Creates Growth
As On The Clock expanded, Dean encountered another challenge common among founders.
Letting go.
For many entrepreneurs, success begins by doing everything themselves. Sales, operations, support, marketing, development, and finance all sit on the owner’s shoulders.
The problem is that what creates growth early often prevents growth later.
Dean shared how hiring experienced leaders transformed the business. Instead of trying to manage every function personally, he began bringing in experts who were better than him in specific areas.
Product management.
Operations.
Marketing.
Customer success.
The goal was simple.
Surround himself with people who could elevate the company beyond his individual capabilities.
That shift not only strengthened the business but also reduced risk. A company that depends entirely on its owner becomes difficult to scale and difficult to sell.
A company led by strong people becomes far more valuable.
AI, Innovation, and the Future
The conversation also explored artificial intelligence and its impact on software development.
Dean sees AI as a powerful productivity tool rather than a replacement for human expertise.
His team uses AI extensively to accelerate development, streamline workflows, and improve efficiency. At the same time, he cautions against blindly relying on technology without understanding the underlying systems.
Tools can accelerate execution.
They cannot replace critical thinking.
For entrepreneurs, Dean believes the biggest opportunity lies in remaining curious and adaptable as technology evolves.
The companies that learn fastest will gain the greatest advantage.
The Entrepreneur’s Blueprint
When asked what advice he would give a young entrepreneur starting today, Dean’s answer was remarkably simple.
Find a problem worth solving.
Validate that the problem actually exists.
Commit fully to solving it.
Most businesses fail because they either solve problems nobody has, or founders give up before momentum has time to develop.
Success rarely comes from short-term effort.
It comes from sustained commitment over years.
For Dean, that commitment turned a kitchen-table idea into a company serving thousands of businesses across the country.
Closing Reflection
One of the most inspiring themes from this conversation was the idea that meaningful growth never happens alone.
Whether building a company, developing leaders, or serving customers, long-term success requires people.
The entrepreneurs who create lasting businesses understand that their greatest asset is not the product they build.
It is the team they build alongside it.
As Dean’s journey demonstrates, the moment you stop trying to do everything yourself is often the moment your business begins reaching its true potential.
Thank you for joining us for this episode of The Exceptional Business Podcast. Stay tuned for more conversations that inspire growth, leadership, and exceptional business building.
AND MORE TOPICS COVERED IN THE FULL INTERVIEW!!! You can check that out and subscribe to YouTube.
If you want to know more about Dean Mathews, you may reach out to him at:
- Website: https://www.ontheclock.com/
- LinkedIn: https://www.linkedin.com/in/dean-mathews-yes
Connect with Chris Seegers:
- Website: https://exceptionalcos.com/
- Email: Ch***@************OS.com
Other Resources:
- Books: Selling Main Street by Chris Seegers
