Greenhaven Road Capital, an investment management company, released its second-quarter 2026 investor letter. A copy of the letter can be downloaded here. The fund achieved an approximate 11% net return in the second quarter, indicating progress from the first quarter.
Key changes to the portfolio will include lower concentration and increased investments with near-term catalysts, alongside a proactive stance on profit-taking. The focus will remain on owning strong businesses and conducting research that challenges consensus views, as several major investments are poised for significant events within the year. Despite declines in market multiples, underlying businesses continue to grow, suggesting a favorable positioning for returns.
Additionally, reviewing the Fund's top five holdings could help identify its best picks for 2026. In its Q2 2026 investor letter, Greenhaven Road Capital highlighted Kingsway Corporation (NYSE:KWY). Kingsway Financial Services Inc. changed its name to Kingsway Corporation (NYSE:KWY) in May 2026.
Kingsway Corporation (NYSE:KWY) is a Chicago-based holding company that operates in extended warranty and business services. On August 14, 2026, Kingsway Corporation (NYSE:KWY) closed at $9.94 per share, reflecting a market capitalization of $284.54 million. Kingsway Corporation (NYSE:KWY) posted a one‑month return of 4.85%, while its shares lost 29.50% over the past 52 weeks.
Greenhaven Road Capital stated the following regarding Kingsway Corporation (NYSE:KWY) in its Q2 2026 investor letter: "With no sell-side coverage and roughly 60% insider ownership, Kingsway Corporation (NYSE:KWY) is effectively ignored by the market. The free float is small, and the business is genuinely hard to analyze. It is transforming from a messy conglomerate into an N of 1 public company built around the search model.
A legacy warranty business still has to be sold, but the signs of progress are tangible: management has assembled a portfolio of nine companies. In the first two years after an acquisition, earnings are typically depressed while capital goes into professionalizing the business and building out sales. Even so, the ramp in quarterly EBITDA for the KSX (Search) segment is already visible.
Extract — continue reading at the source.
