LongKWYSeptember 2, 2026

Greenhaven Road Investment Management, LP on Kingsway Corporation

Thesis

Kingsway is evolving from a neglected conglomerate into a public-market version of the search-fund model. Insider ownership is high, sell-side coverage is absent and Greenhaven believes the company's collection of acquired businesses is increasingly demonstrating attractive organic and acquisition-driven economics. Quarterly EBITDA in the search-fund segment has risen materially, and the fund sees a credible path to more than $6 million per quarter. Continued acquisitions around five times EBITDA, combined with organic growth and tax advantages from existing net operating losses, could eventually turn Kingsway into a self-funding compounder. A successful transition to a cleaner pure-play structure could also support a higher valuation multiple.

Investors want to own 'compounders,' and I believe Kingsway is an emerging one.
Greenhaven Road Investment Management, LP — July 2026 Investor Letter

Key risks

  • Acquired businesses may fail to deliver expected organic growth
  • Future acquisitions may be completed at less attractive valuations
  • Execution risk remains in simplifying the legacy corporate structure