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Reclaiming Stewardship Through Direct Investing
Jay Rogers
13 April 2026
A regular writer, financial industry veteran and business school lecturer writes here about direct investing – a familiar theme to readers of FWR – and gives a level of historical perspective to the topic. Direct investing is, in some ways, the oldest form that there is. With so much focus today on private market investing – both on the pros and cons side – this article is particularly timely. To comment on such material, please email tom.burroughes@wealthbriefing.com and amanda.cheesley@clearviewpublishing.com. The usual disclaimers apply to views of guest writers, and we thank Jay Rogers for his contribution to conversations on these topics. Rogers is also a guest lecturer at the USC Marshall School of Business. Entrusting capital to outsiders often resembles hiring a fox to guard the henhouse: fees mount, visibility fades, and exits arrive on someone else’s timetable. In my experience, families with operating history in a sector routinely outperform fund benchmarks by 300 to 500 basis points net of avoided fees. Direct structures afford board seats and the ability to steer toward values-aligned decisions, such as domestic manufacturing, rather than chasing ESG mandates imposed from afar. Unlike the scheming dynasties in Succession, where outsourced advisors fuel discord, conservative families thrive by keeping decisions in-house, much as the Corleone family insisted on handling "family business" personally.
In an age of market gyrations that can wipe out paper gains overnight and fund structures that extract fees with the quiet efficiency of a well-oiled machine, families of substantial means face a stark choice. Do they continue outsourcing their hard-earned capital to third-party managers who may prioritize their own incentives over long-term family objectives? Or do they reclaim direct control, leveraging the very expertise and history that built their wealth in the first place? Direct investing through family offices offers precisely this path, one rooted in prudence, self-reliance, and generational responsibility.
After more than 25 years advising ultra-high net worth families, I have seen time and again how this approach not only preserves capital but honors the conservative virtue of stewardship. It deserves attention now more than ever, as families navigate inflation pressures, regulatory shifts, and the imperative to pass intact legacies to the next generation.
The practice of dedicated family wealth management stretches back centuries, embodying timeless principles of household governance. In ancient Rome, the major-domo served as the principal steward of the household's affairs, entrusted with oversight of estates, finances, and daily operations to ensure continuity across generations. European landed gentry later refined this model through the management of vast holdings, where family retainers balanced agricultural yields and inheritance planning with a keen eye toward preservation rather than speculation. The modern family office crystallized in the crucible of America’s Gilded Age. John D Rockefeller’s experience stands as the archetype. By the late 1890s, his portfolio had become a disorganized collection of dubious holdings. Enter Frederick T Gates, who effectively became the first professional family office executive. By divesting the weak and orchestrating the pivotal Mesabi Range iron ore investment, Gates acted as a one-man investment bank with intimate family alignment.
Philosophically, this evolution aligns with conservative thought on ordered liberty and inheritance. Edmund Burke, the 18th century politician and writer, described society as a contract between the living, the dead, and the yet unborn, with the family as its foundational "little platoon." Aristotle’s concept of oikonomia, the art of household management, further underscores that true wealth stewardship begins at home, not in distant fund vehicles prone to agency conflicts.
From a scientific lens, behavioral economics illuminates the pitfalls of delegation. Principal-agent problems reveal how external managers often chase short-term performance at the expense of patient capital. Much like evolutionary biology highlights kin selection, where resources flow preferentially to bloodlines for survival, family capital is most naturally protected when kept within the family’s direct orbit.
Today, the shift toward direct investing has accelerated, driven by conservative instincts for control amid global uncertainty. According to Citi Private Bank’s 2025 Global Family Office Report, 70 per cent of family offices now engage in direct investments, with 40 per cent ramping up activity in the past year alone. Nearly two-thirds anticipate completing six or more direct deals in the coming 12 months, per BNY Mellon’s 2025 data.
This is no fleeting fad. The number of single-family offices has tripled since 2019, managing trillions in assets as families bypass the "2 and 20" fee structures emblematic of Wall Street excess. Why pay a manager 2 per cent annually plus 20 per cent of profits when your family possesses generational knowledge in real estate or energy?
High-profile examples lend weight to this movement. The Walton family, through Walton Enterprises, wields its Walmart-derived expertise to deploy capital directly into logistics, maintaining controlling stakes that align with core competencies. Similarly, the Koch family established 1888 Management to scout direct investments in sectors echoing their industrial roots. Even the Rockefeller legacy persists with descendants emphasizing thematic direct plays.
The solution is a return to first principles: integrate direct investing as a cornerstone of your family office. Begin with a formal expertise audit. Convene the family to map generational knowledge in specific sectors. This identifies high-conviction areas where history provides an edge, justifying direct deployment over blind fund commitments. Next, formalize governance by drafting an investment policy statement that mandates minimum holding periods and structure transactions through family limited partnerships or LLCs to facilitate valuation discounts for estate tax purposes while coordinating with generation-skipping trusts.
Engage specialized legal and tax counsel early, ideally those versed in Section 162 business expense treatment for family office operations, to maximize deductions on due diligence. Start modestly with co-investments alongside trusted sponsors in familiar industries to build internal capabilities. Target deals allowing meaningful influence, negotiating terms that align exit horizons with family liquidity needs. Monitor via quarterly family investment committee reviews, emphasizing metrics like cash-on-cash returns over the smoke and mirrors of IRR theater. In one family I advised, shifting 25 per cent of alternatives to direct energy assets eliminated $4 million in annual fees and enhanced after-tax compounding by an estimated 1.8 per cent annually.
Direct investing through family offices represents far more than a tactical allocation shift. It embodies a philosophical return to a time when families acted as true stewards rather than passive clients. In a world prone to fleeting financial fashions and reckless government spending, the enduring lesson remains: wealth built through disciplined enterprise deserves governance by those who understand its origins. As the 18th century politician and author Edmund Burke might remind us, true conservatism cherishes what works across generations. Will your family office lead this quiet revolution, or watch from the sidelines as others do? The choice, and the control, rests firmly in your hands.
Sources
-- Citi Private Bank. 2025 Global Family Office Report.
-- BNY Mellon. 2025 Investment Insights for Single Family Offices.
-- Compound Planning. A History of Family Offices.
-- Sadis & Goldberg LLP. Direct Investing by Family Offices.
-- PwC. Global Family Office Deals Study 2025.
-- UBS. Global Family Office Report 2025.
Historical accounts are drawn from Ron Chernow's Titan: The Life of John D Rockefeller, Sr and contemporary industry analyses from FINTRX and Preqin.