Four Million In Four Years With Matthew Woolley The Ultimate Landscape CEO

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Four Million in Four Years with Matthew Woolley

1d ago 46:18

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In this episode, 24-year-old entrepreneur Matthew Woolley, founder of Woolley Outdoors in Lancaster, Pennsylvania, shares his journey from mowing lawns after work to building a company that now generates nearly $4 million in annual revenue. In just four and a half years, Matthew’s success has been driven by his relentless work ethic, willingness to learn, and focus on people. He opens up about his early challenges, key leadership lessons, hiring strategies, and how he manages rapid growth while maintaining balance in his personal life. His story offers practical insights and inspiration for anyone looking to grow their business with purpose and clarity.

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Key Takeaways:

From side hustle to $4M business in under five years through focus, grit, and vision.

Building systems early and learning to delegate are key to sustainable growth.

Leadership begins with people—respect, communication, and understanding what motivates them.

Transitioning from manual processes to digital systems like Jobber and Aspire to improve efficiency.

The value of joining peer groups for benchmarking, learning, and strategic development.

Managing rapid expansion while maintaining profitability and financial discipline.

Balancing business goals with marriage, relationships, and personal well-being.
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