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Fair Weather Strategies
Craig Drill runs Fair Weather Strategies, a concentrated long-only family office in New York holding equities for decades, not quarters.
Fair Weather Strategies
Fair Weather Strategies was established as the private investment office for Craig Drill, a former Goldman Sachs partner whose career in institutional equities and capital markets provided the foundational wealth. The firm operates from New York and manages the Drill family's capital with a deliberately low profile, rarely appearing in public transactions or media coverage. The investment approach centers on concentrated, long-only public equity positions held over multi-decade horizons. The portfolio typically contains fewer than 15 names, with holdings confirmed through 13F filings over the years including Berkshire Hathaway, Markel Corporation, and Diageo. Drill does not pursue venture capital, private equity funds, or real assets as primary allocation sleeves; the firm's edge comes from deep fundamental research and a willingness to remain invested through full market cycles without redemption pressure. The geographic focus remains North America and developed Europe. Craig Drill spent over two decades at Goldman Sachs, rising to partner before leaving in the early 1990s to found Drill Capital Management and later consolidate family activities under Fair Weather Strategies. The office runs lean — likely fewer than five investment professionals — and does not maintain satellite offices. In 2020, regulatory filings showed the firm expanding a position in a global spirits company during the pandemic-driven market dislocation, consistent with its countercyclical posture. The structural differentiator is temporal advantage: the absence of limited partners, quarterly reporting demands, or a mandated investment committee cycle allows Fair Weather Strategies to act on conviction during moments when institutional managers face redemptions or benchmark-driven constraints. This architecture places it closer to a personal holding company than a modern multi-strategy family office, with investment decisions resting solely with the principal.
General information
Firm type
Single Family Office
Year founded
—
AUM
Undisclosed
Location
Region
North America
Country
United States
City
New York
Corporate office
New York, NY, United States
Principals
Craig Drill
Principal
Sector focus
Frequently asked questions
Who runs investment decisions at 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.
What is the investment strategy?
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.
Does Fair Weather Strategies take outside capital?
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.
Which sectors does Fair Weather Strategies favor?
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.
How does Craig Drill's Goldman Sachs background shape the portfolio?
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.
Is Fair Weather Strategies related to Drill Capital Management?
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.
What is the firm's succession plan?
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.
Profile maintained by Altss using OSINT (open-source intelligence), regulatory filings, licensed data partners, and verified direct submissions. Read the methodology. Last updated: . Continuous refresh with full update cycles at least every 30 days.
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