Considered thinking
for considered wealth

Every generation of investors encounters a moment when the market seems to have lost its mind. Prices detach from fundamentals. Narratives replace analysis. Fear or greed — or some volatile mixture of both — drives decisions that participants will later struggle to explain. In these moments, the most valuable quality an investor can possess is not intelligence, not information, not even conviction. It is patience.

Patience in investing is not passivity. It is not the absence of action, but the discipline to act only when the evidence warrants it and the terms are favourable. It means holding a position through a drawdown not because you are indifferent to the loss, but because you have done the work to understand that the underlying value remains intact. It means declining to chase a rally not because you fear success, but because the price has exceeded what a sober analysis can justify.

Consider the historical record. The investors who have generated the greatest long-term wealth are not those who traded most frequently or reacted most quickly. They are those who identified quality, purchased it at reasonable prices, and then had the fortitude to hold it through the inevitable periods of doubt. Warren Buffett's returns are not the product of brilliant timing. They are the product of decades of disciplined compounding, punctuated by occasional bold action during periods of market distress.

At Oakwood, we counsel our clients to view volatility not as a threat but as a feature of functioning markets — one that, over time, creates opportunity for those who are prepared and patient enough to seize it. The next correction will come. It always does. And when it arrives, we will be ready — not with panic, but with a carefully maintained list of exceptional businesses we would like to own at better prices.

The American family has changed profoundly over the past fifty years. Blended families, international marriages, non-traditional structures, and the growing prevalence of family businesses that span continents — these realities demand an estate planning approach that is as nuanced and individual as the families themselves.

Too often, estate planning is treated as a legal exercise — a matter of documents and structures and tax-optimized transfers. These technical elements are essential, of course. But they are not sufficient. The most carefully drafted trust is worthless if it fails to account for the human dynamics of the family it serves. A succession plan that optimizes for tax efficiency but ignores sibling rivalry or generational differences in values is a plan that will ultimately fail.

In our practice, we begin every estate engagement not with documents but with conversation. We want to understand the family's values, their aspirations for future generations, their concerns about wealth's effect on character and ambition. We explore questions that many families find uncomfortable but essential: How much is enough for each heir? What role should philanthropy play? How do we prepare the next generation for the responsibility of wealth without burdening them with obligation?

Only after we understand the human dimensions do we turn to the structures. And even then, we prefer simplicity. The most elegant estate plan is not the most complex one — it is the one that accomplishes the family's objectives with the fewest moving parts, the greatest transparency, and the highest likelihood of being understood and honoured by the generations that will inherit it.

Every few years, a new investment theme captures the imagination of the financial world. Cryptocurrencies. SPACs. Meme stocks. Artificial intelligence. Each arrives with breathless enthusiasm, a compelling narrative, and the implicit suggestion that anyone who fails to participate is hopelessly behind the times.

We have seen this pattern repeat throughout our firm's history. In the late 1990s, it was internet stocks. In the mid-2000s, it was structured credit products. In each case, the underlying innovation was real and significant. But the investment frenzy that accompanied it was something different entirely — a collective suspension of the analytical discipline that separates investing from speculation.

Our refusal to chase trends is not a rejection of innovation. We hold meaningful positions in technology companies, in healthcare innovators, in firms that are reshaping their industries. But we invest in these companies because we understand their businesses, can value their cash flows, and believe the price we pay offers a reasonable margin of safety. We do not invest in narratives. We do not invest in momentum. And we certainly do not invest in the fear of missing out.

This discipline has occasionally meant underperforming during the euphoric phase of a cycle. It has always meant outperforming during the correction that follows. Over the full cycle — and our clients invest over many cycles — the math favours the patient and the disciplined. It always has.