Rob Casper: From Marine to PE to Public Company Leadership

Kingsway Financial, a decades-old public company once focused on insurance and warranty, has reinvented itself as a small business compounder with permanent capital. Through its Kingsway Search Accelerator (KSX), the company brings on 3-4 Operators-in-Residence each year, equipping them to find, acquire, and run lower-middle market businesses. KSX has backed 7-8 searchers who have completed acquisitions to-date. Kingsway's annual revenue stands at ~$118 million, with ~$17 million coming from the plumbing platform that Rob leads.

The ambition mirrors the playbooks of companies like Judges Scientific and Heico, long-term compounders that redeploy capital into enduring, cash-generating niches. True compounders focus on owning excellent small businesses indefinitely, where time and operating excellence are the key drivers of wealth.

Rob is a Marine Corps veteran and approaches leadership through service. "Serve your people first and the numbers will follow," he says, which reflects his business philosophy and a bottom-up approach learned through years of people management. The plumbers and technicians on his teams are the value creators, and Rob sees his role as equipping them to succeed.

Home services, and plumbing (and HVAC) in particular, are in the later innings of industry consolidation. Private equity is everywhere, multiples are high, and the easy wins are gone. Rob and KSX believe the way to win now is through operational excellence and people-first leadership.