114: Scaling EarthScapes – Growing a Family Side Hustle into an $8M Landscaping Business

Podcast cover for The Corporate Dropout, Episode 114. The title reads: Scaling Earthscapes – Growing a Family Side Hustle into an $8M Landscaping Business. Featured guests are Josh Eldredge and Matt Eldredge. The design has teal and lavender abstract shapes with a circular photo of Josh and Matt smiling, both wearing baseball caps and casual shirts, inside a bus or train setting.
 
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What does it really take to grow a family business into an $8 million landscaping company while keeping quality, culture, and family at the center?

On this episode of The Corporate Dropout, Rachael sits down with twin brothers Josh and Matt Eldredge, co-owners of EarthScapes in Virginia Beach. What started as mowing lawns for neighbors in high school has grown into a multi-million dollar landscaping and outdoor living business. With certifications in landscape design, horticulture, and pest management, Josh and Matt bring decades of expertise and a people-first approach to every project.

The brothers share how they transformed EarthScapes from their dad’s summer side hustle into a regional leader in landscaping, pools, and outdoor living spaces. They open up about lessons in leadership, building systems that support growth, and dividing responsibilities to avoid burnout while running a family business. Josh and Matt share how they tackled hiring challenges, scaled through partnerships, and built a business grounded in grit and strategy.

In today’s episode you will learn:

  • How EarthScapes grew from a small lawn service into an $8M landscaping company
  • The systems and processes that made scaling possible
  • Why leadership, culture, and communication are critical in service-based businesses
  • How Josh and Matt balance business ownership with family life
  • The role of partnerships in expanding into pools and outdoor living design
  • Their best advice for entrepreneurs ready to grow a business with integrity

& SO MUCH MORE!

 

About Josh Eldredge

Josh Eldredge has been working for EarthScapes since the first mower manicured a yard in 1996. A high school job turned into a passion for horticulture and more than 20 years of experience in the landscaping industry. Josh continued his education by obtaining an Associates Degree in Landscape Design & Maintenance from Tidewater Community College in 2004. He also has his Class A Contractors License as well as Commercial Applicators license for Ornamental Pest Control. In 2011, he and twin brother Matt, purchased EarthScapes from their father. Josh likes to work closely with property managers and our production manager to ensure our high quality and attention to detail stays consistent throughout all of our maintenance crews. When Josh isn’t busy in the office or the field, you can find him on the golf course, fishing or hanging on the beach with family and friends. In 2023, Josh and his wife, Michelle, became certified foster parents welcoming two children in their home. They are currently in the adoption process with their daughter, which should be finalized this fall. Josh and his family reside in Virginia Beach.

About Matt Eldredge

When the doors to EarthScapes opened in 1996, Matt Eldredge was pushing mowers at the young age of 14. Along with twin brother, Josh, Matt continued his education by obtaining an Associates Degree in Landscape Design & Maintenance from Tidewater Community College in 2004. He also has his Commercial Applicators license in Turfgrass and Ornamental Pest as well as holding a Chesapeake Bay Landscape Professional 2 certificate. After marrying his high school sweetheart in 2008, he relocated to northern Virginia. While in Manassas, Matt served as an Operations Manager for a multi-million dollar landscape company for the next 3 years. In 2011, Matt returned home and became co-owner of EarthScapes. Matt has a passion for landscape design and loves to work closely with clients to make their dreams a reality. When Matt isn’t busy designing or on a project site, you can find him hitting golf balls with his twin or hanging on the beach with family and friends. Matt and his wife, Stephanie, have 3 kids and reside in Virginia Beach.

 

Resources

Calling All Corporate Dropouts!

Have you or someone you admire ditched your 9 to 5? We want to hear from you! Send us an email [email protected] to be considered as a guest.

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