Kingsway

Kingsway Financial Services, based in Chicago, Illinois, operates as a holding company that acquires and grows small businesses through a publicly traded search fund model, leveraging net operating losses for tax efficiency. Functioning as a merchant bank and search fund accelerator, the firm focuses on B2B services, vertical market software, and skilled trades, executing buy-and-build strategies, such as in the plumbing industry. With a market capitalization of nearly $400 million, Kingsway owns 15 businesses, generating revenue through their ownership and growth, including the November 2022 acquisition of CSuite Financial Partners for $8.5 million. Key figures include CEO JT Fitzgerald and investor Joseph Stilwell, with a notable portfolio exit being PWSC, a home warranty provider that yielded a 10x equity return in 4.5 years. Kingsway Financial Services was founded in 1989 by Neil G. West.