Chief WINK Investigates Reporter Chorus Nylander
•8/28/2026

NAPLES, Fla. (WINK) — After a private equity partnership collapsed into insolvency and left dozens of homeowners stranded, the founder of Southwest Florida’s 54-year-old Kelly Roofing has stepped out of retirement to buy back the company’s debt, clear vendor liens, and issue full refunds to impacted clients.
Former owner Ken Kelly reclaimed management of the Naples-based roofing company following weeks of disruption that had some customers receive deposit refund checks that bounced and triggered thousands of dollars in property liens for others that had unfinished work.
Kelly said the problems mounted after Kelly Roofing partnered with a private equity group to expand services across Florida. Market dips and financial strain at newly acquired regional entities led to missed loan payments and bank covenant defaults, he said. The resulting collapse left 153 active clients in limbo across four affiliated brands—spanning Collier County, Central Florida, Palm Beach, and Jacksonville.
"I was on a golf course and got a call from one of our employees who was literally crying," Kelly recalled. "I came in, stood right here in this room, talked to the team, and called the private equity team."
Upon learning the situation was in the hands of lenders, Kelly submitted an offer directly to the bank to purchase the debt for Kelly Roofing and its three affiliated regional branches. Five days later, the transaction closed.
Customer Restitution and Ongoing Claims
In total, 77 customers faced deposit-related disputes across the four brands. According to Kelly, every impacted customer has been made whole:
Completed Contracts: Most affected homeowners chose to resume work under the restructured firm.
Refunds Issued: Clients who opted out received full deposit returns. Those who initiated bank chargebacks were allowed to retain credit card processor credits.
Canceled Agreements: Thirteen customers withdrew due to emergency leak repairs or lost trust.
Naples resident Andrew Aste, who relies on Social Security income, was left stranded in July after paying a $5,000 deposit and receiving a bounced refund check. After contracting another firm, Aste received a full deposit refund this week. "It just shows he's a stand-up guy, and I wish him nothing but the best of luck," Aste said.
However, some property and financial issues remain unresolved. Kelly said 19 homeowners faced supplier liens after the collapse, including 16 from primary distributor ABC Supply Company. Kelly stated his team is actively coordinating with vendors to release all property encumbrances.
WINK Investigates also spoke with a woman that doesn’t want to be identified but says she was a contracted Chief Marketing Officer for the company and is owed around $25,000 for two months of unpaid work.
She told Chief WINK Investigates Reporter Chorus Nylander that Ken Kelly has “ghosted” her after attempts to collect the money.
Kelly told Chorus he has in fact stopped communicating with her.
“That individual has contacted an attorney and prevents me from speaking with her and we’ve been working through her attorney to get her resolved,” he said.
WINK Investigates also spoke with Debra and Gary Smith, who live in Ormond Beach, they paid over $3,000 for a deposit to Integrity Roofing and Gutters, one of the affiliated companies.
Kelly told WINK Investigates he has also taken over the obligations for customers with that entity but on Thursday said, “I'm not aware of this customer, but I will research the situation and find a resolution.”
Restructuring as an Employee-Owned Firm
Kelly plans to dissolve all out-of-market subsidiaries and concentrate operations exclusively on the core Kelly Roofing brand in Collier County.
Moving forward, the business is transitioning into a leaner, employee-owned enterprise alongside four key partners. "We're moving from a family legacy organization to employee-owned," Kelly said. "My next turn is going to be to make sure that the employees own the company and continue this for another 54 years."
Throughout our investigation the private equity firm, Monument MicroCap Partners, has not responded to request for comment.
The primary supplier that placed liens on customers homes, ABC Supply Company, has also not responded to requests for comment.
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