Evan DiLeonardi Bought a $2M Ohio Cleaning Business, Then Pivoted to 20% Stakes

The Setup Evan DiLeonardi was 28, a former healthcare and management consulting analyst, and a self-described workaholic who wanted lifestyle flexibility more than he wanted a W-2. He stacked Airbnb income, joined Ben Kelly's Acquisition Ace community in October 2023, and started hunting. The target that cleared diligence was Quality Cleaning Service of Northwest Ohio: a commercial janitorial and floor-care operator roughly an hour outside Toledo, doing about $2M in revenue and $500K in SDE at 25% margins. The attraction was textbook self-funded search: recurring B2B contracts, fragmented competition, low capex, SBA-fundable, and a seller who wanted to retire. The flag that would later matter: the GM was the seller's step-grandfather, and several family members worked in the business. The Deal - Purchase price: $1.6M (3.2x SDE) - 90% SBA 7(a) - 5% seller note, 2-year standby then 8-year term - 5% buyer cash equity - No real estate - Annual debt service: ~$220K Closing dragged six months because the seller had unresolved tax issues. During the delay the seller mentally checked out, service quality slipped, and a few accounts walked before Evan ever got the keys. He closed in September 2024 anyway. First 100 Days The honeymoon was short. Inside the first quarter post-close, Evan found that the GM and family members had been inflating hours, hiding customer complaints, and functionally skimming the business. He made the call fast. - Fired the GM and multiple family members within 3-4 months - Absorbed an age-discrimination lawsuit from the fired GM (later settled) - Lost another operations manager to an out-of-state move - Ran the business in survival mode: 40-50 hour weeks, thinned to two ops managers, actively losing accounts - Promoted the strongest lead supervisor into the GM seat He calls the period "a scary J-curve," not a turnaround. The distinction matters: the contracts and the brand were healthy; the people layer was rotten. Operating Moves With the new GM installed, Evan rebuilt the operating stack for remote control. - Software for remote monitoring of crews, completion, and quality - Bonus structures tied to account retention and new-account close - Marketing engine: Google Ads, SEO, outbound lead-gen tests - Recruiting pipeline to backfill cleaning staff and build bench - Weekly cadence with GM; in-person visits a few days per quarter He draws a hard line between remote and absentee. He runs the business from Tulum and elsewhere, but he is on the phone daily and the incentive system is designed so the GM's payout only lands when Evan's numbers land. Operating Lessons - Price family-run SMBs with a specific risk premium. Hidden nepotism and soft embezzlement are a repeat pattern under $1M SDE, not a freak event. - Six-month closing delays cost real EBITDA. Negotiate a price adjustment mechanic if the seller's issues push the timeline. - Fire the embedded family fast and all at once. Staggered terminations give the network time to coordinate retaliation (lawsuits, account poaching, staff walkouts). - Internal promotions beat external GM hires during a crisis....