There Is No Single Playbook for Family-Office Direct Investing
Christian Cantalupo, Investment Director at KKCG US, recently spent several days in Laguna Beach for Institutional Investor’s 23rd Annual Family Office Wealth Conference. He had the opportunity to co-lead a discussion entitled “Are You Truly Built to Win in Direct Investing?” The conversation brought together a range of family offices to compare how they think about direct investing, what they are trying to accomplish, and the capabilities required to do it well.

What Does “Direct Investing” Actually Mean for a Family Office?
Direct investing is often discussed as though it were a single strategy. At the conference, it looked more like a set of choices. Some families pursue control of operating businesses. Others prefer co-investments, minority positions, or partnering with independent sponsors. Some concentrate on sectors they know intimately, while others are still deciding how much investing they want to do themselves.
The differences matter because the right approach to direct investing depends on what the family wants its capital to do. Is the goal to build and own businesses over decades? Generate income without taking operational control? Diversify wealth tied to an existing company or asset? Put the family’s industry experience and relationships to work? Those objectives point toward different investments, as well as different definitions of success.
When Does Taking Control Make Sense?
For families with deep operating experience, control can be a natural extension of what they already know and are comfortable with. This operational expertise often brings sector knowledge, industry relationships, and credibility with management teams. A family able to bring those strengths to a business may have both a competitive and value-creation advantage that goes beyond providing capital. The permanent nature of family capital can matter too. Without a fund’s fixed exit timetable, a family can choose to hold a strong business for the long term, which can be very compelling to founders looking for a partner.
But control is not the only way to invest directly. A co-investment or non-control position can give a family exposure to a business without requiring it to become the lead owner. For a family seeking a diversified portfolio, or one building experience before pursuing its own deals, that may be a better match for its goals and resources. The distinction is not between an ambitious strategy and a cautious one. It is between different roles a family can choose to play, and the different needs the investment strategy is designed to satisfy.
Can Direct Investing Make a Portfolio Simpler?
The panel also surfaced a less obvious motivation for going direct: simplicity. One example involved hundreds of fund positions that had become difficult to track, forecast for liquidity, and manage through successive commitments. Moving toward fewer, larger, longer-duration holdings was as much a portfolio-management choice as an investment choice. For another family, reducing fees was a more immediate reason to invest directly. Neither of those goals, on its own, determines what the family should invest in. However, both can materially influence what form of direct investing makes sense.
This is why comparing family offices by a single direct-investing template can be misleading. A control buyer, a sector specialist, and a family seeking returns through non-control positions may all be making sound decisions while building very different portfolios and internal investment functions. The more useful question is whether the approach reflects the family’s objectives and whether it has the capabilities, relationships, experience, or other advantages necessary to execute that approach well.
“Talent should follow strategy rather than define it.”
Talent is an important part of making that choice work, though talent should follow strategy rather than define it. Many family offices emphasized the value of “expert generalists” in building a direct investment function. One of the key advantages of permanent capital is flexibility, and investment professionals who can evaluate opportunities across industries, structures, and asset classes can help leverage that flexibility rather than inadvertently constrain it. Just as important is the ability to understand the family’s objectives and build an investment strategy around them, rather than arriving with a predetermined playbook. The investment function ultimately exists to serve the family’s broader objectives. Generating attractive returns is essential, but it is one part of a mandate that may also encompass liquidity, diversification, control, legacy, risk tolerance, and time horizon.
So Where Should a Family Office Start?
The lesson from the conference is not that every family office should invest directly, or that every direct-investing model will succeed. It is that direct investing is too broad a label to be useful on its own. The starting point for any direct-investing strategy is clarity around what the family wants its capital to achieve. That includes understanding what the family can genuinely contribute and how it will define success on its own terms. That clarity can then inform the direct-investing approach, including whether direct investing is the right strategy at all.
For more insights into investment strategies and decision-making, read Christian's previous article, The Best Ideas in the Room Were Built on Discipline.
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