Milestone Capitalizes Specialty Insurance Holding Company

Milestone Partners announced that it formed specialty insurance holding company, Insure Homes Holdings, which invested in the recapitalization of Cypress Group Holdings and affiliated insurance service technology companies.The companies also agreed to obtain control of Cypress upon the sanction for the change of control by the domestic regulator of their insurance company subsidiary.

Cypress—a holding company that owns managing general agent and insurance carrier subsidiaries— have served homeowners throughout the Gulf Coast and Southeast since its founding in 1998.Cypress operates an asset light model with superior returns on equity, leveraging about 20 years of data to generate stable recurring revenues through more than 1000 independent agent partners and working with its reinsurance partners to limit retained risk. Cypress was purchased in 2014 by veteran reinsurance executives Joe King, Adrian Ryan  and Enda McDonnell, who partnered with Milestone in its 2020 recapitalization.

Insure Homes acquired four affiliated insurance service technology entities founded by King, McDonnell and Ryan being the IT implementation and administration software company as part of the transaction.This unique combination with Cypress establishes Insure Homes as a vertically integrated market leader, distinguished in its deep know-how throughout the value chain.

James Billmyer, Principal at Milestone, adds that “Joe, Enda, and Adrian have leveraged their deep expertise in reinsurance and the P&C sector broadly to create a true technology enabled platform, uniquely positioned to better serve its clients. We are excited to partner with an exceptional, entrepreneurial management team during this transformational period in the insurance and reinsurance marketplaces.”

“We could not be more pleased with a partner like Milestone supporting our strategic initiatives. Given their targeted sector focus on financial service and technology companies, we are looking forward to working with them in this next stage of growth of our enterprise,” said Joe King, Co-CEO of Insure Homes.