Hillside Landscape, Inc.

Hillside Landscape has served Chicago's North Shore for 25 years, maintaining upper-end residential properties and a diverse commercial book of medical offices, apartments, retail, and condo associations, with niches in pond building and landscape lighting. Customer retention runs 93 percent, and the maintenance contracts were fully assignable, exactly what a buyer wants to see.

That was not an accident. Owner Gary Moderhock, a CPA by training who ran the company with his wife Corinne, spent the year before selling deliberately shifting the business from construction-heavy work toward recurring maintenance, specifically to make it more valuable and easier to hand off. His conditions in a sale were simple: the nine-person crew keeps their jobs, and he signs whatever non-compete the buyer needs.

Hillside connected with Joshua Lumbreras on Rejigg in February 2026 and reached an LOI in April. When conventional SBA financing proved a poor fit for the deal, buyer and seller built a structure together, seller financing alongside cash, and closed in June 2026 with the crew intact and the owner headed into retirement.

Joshua Lumbreras bought Hillside as an individual buyer committing nearly everything he had to ownership, with a seller willing to finance part of the deal to make the handoff work. He inherited assignable contracts, a 93 percent retention rate, and a crew the previous owner protected in the negotiation.