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Keep an Eye on These Two Brothers. They’re Hungry, They’re Growing, and They’re Just Getting Started.

Published on: September 25, 2026

Author: The Better Contractor

Avery and Owen are brothers who played football together at McKendree before turning a college side hustle into VIP Outdoors, a real lawn care and hardscaping company built around a model most people in the industry have never tried.

Instead of billing customers differently every month based on what’s actually happening outside (mowing in the summer, leaf cleanup in the fall, snow removal in the winter), VIP Outdoors charges one flat rate, every single month, all year long. Mowing, landscaping, snow removal, all of it, wrapped into one predictable payment so customers never have to think about it. No surprise bills, no seasonal price swings, just one number they can count on twelve months a year.

In this episode of The Better Contractor, Brent sits down with Avery and Owen to talk about what it actually took to go from printing flyers in college to running a legitimate, scaling business, including the story of how one of their own customers, David St. John, became a mentor and eventually a co-owner.

In this episode:

  • How two brothers went from playing football together at McKendree to starting a company together
  • The moment they realized VIP Outdoors could be a real business, not just beer money
  • How a customer became a mentor, then a business partner
  • Why they built a flat rate, year round subscription model covering mowing, landscaping, and snow removal, and how customers actually reacted
  • What building a business with your brother really costs you
  • Balancing marriage, a new baby, and a growing company
  • Why they want to build something bigger than themselves
  • Their 5, 10, and 20 year goals for VIP Outdoors, and how big they actually want it to get

If you’re a contractor thinking about recurring revenue, scaling past being “just a lawn guy,” or building a business with family, this one’s for you.

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