The Ultimate Landscape CEO - Jeffrey Scott Four Million in Four Years with Matthew Woolley
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Oct 30, 2025 Matthew Woolley, founder of Woolley Outdoors, skyrocketed his landscaping business to nearly $4 million in just four years. He shares invaluable lessons on leadership and the importance of a people-first approach. Matthew discusses transitioning from manual processes to digital systems and the significance of building an overhead team. He also emphasizes the balance between rapid growth and personal well-being, the role of peer groups in shaping his strategies, and the impact of effective delegation. His journey inspires aspiring entrepreneurs to grow with purpose.
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Grinding Through Night Shifts
- Matthew worked full days as a carpenter and mowed lawns every evening until he quit his job the following year.
- He even switched to night shifts to keep both jobs going while building his business.
From $90K To $1.8M In Three Years
- Matthew recounted revenue growth from $90K in 2021 to $1.8M in 2024 across staged crew expansions.
- He personally handled sales, scheduling, and admin while operating mostly on pen and paper in 2024.
Pick Software You Can Implement
- Implement software that you can actually operationalize and staff to manage growth.
- Matthew moved from paper to Jobber this year, and plans to implement Aspire for deeper analytics.