Caleb recently had Doug Ryan, owner of DRE Landscaping, on his podcast to discuss Doug's experience growing his lawn care business from a small neighborhood operation to servicing over 140 residential properties. Doug started mowing lawns as a kid in middle school and steadily took on more customers over the years.

By age 20, Doug decided to pursue landscaping full-time after seeing the money potential in the business. He now runs a three-man crew focused on mowing, seasonal maintenance, and some commercial snow removal accounts. Doug shared that efficient routing has allowed him to scale his residential mowing business significantly. He aims to hit 300 lawns serviced by next season.

One challenge Doug discussed was keeping customers happy, as even small mistakes can lead to complaints. He's also learned that while he enjoys doing the work, he can only scale the business by bringing on additional employees. Doug recently invested in a larger shop space and equipment like a skid...