Fair Weather Strategies

Craig Drill makes all investment decisions. He is the principal and sole decision-maker, having previously spent over two decades at Goldman Sachs, where he became a partner in the equities division. The firm has no investment committee and no outside influence on portfolio construction.

The firm runs a highly concentrated, long-only public equity portfolio. Holdings are typically held for ten to twenty years or longer, with positions rarely numbering more than fifteen names. The approach relies on deep fundamental research, an emphasis on durable compounding businesses, and the structural advantage of permanent capital that never faces redemptions.

No. Fair Weather Strategies is a single-family office managing exclusively the Drill family's capital. It has never marketed to outside investors, does not operate as a registered investment adviser to unaffiliated clients, and maintains its low profile specifically to avoid the reporting and behavioral constraints that come with third-party capital.

Public filings show a long-standing preference for financial services, consumer staples, and insurance-like compounders. Confirmed positions have included Berkshire Hathaway, Markel Corporation, and Diageo. The firm avoids sectors dependent on rapid technological obsolescence or frequent capital-market refinancing, favoring businesses with multi-decade demand visibility.

Drill spent his Goldman career in institutional equities and capital markets, developing a network that provides direct access to management teams and a practitioner's understanding of market structure. This background supports the firm's ability to size positions during dislocations — such as adding to Diageo in early 2020 — when benchmark-driven sellers create price disconnects from long-term intrinsic value.

Yes, Drill Capital Management was the predecessor entity Craig Drill founded after leaving Goldman Sachs in the early 1990s. Over time, activities were consolidated under the Fair Weather Strategies name as the single-family office vehicle, though regulatory filings occasionally reference both. The investment philosophy has remained consistent across both structures.

The succession structure is not publicly disclosed. As a concentrated single-family office with all investment decisions resting with Craig Drill personally, institutional allocators have noted key-person risk as the defining governance question. No formal announcement of a next-generation principal or external succession hire has been made.