This dialogue was inspired by the recursive brilliance of Douglas Hofstadter and the whimsical logic of Lewis Carroll. It’s part satire, part philosophy, and, like the market, a little bit absurd.

There’s no shortage of articles and hot takes comparing Roth and Traditional retirement accounts. Most of them walk you through marginal tax rates, retirement income projections, and maybe offer a simple calculator to “optimize” your contributions. But here’s the thing: optimizing the unknowable is a fool’s errand.

Few concepts in economics are as routinely mischaracterized as a trade deficit. It is often portrayed as a measure of national decline, a scoreboard where exports represent wins and imports represent failure. This framing, although appealing, is both analytically weak and historically outdated.

Tariffs are often presented as instruments of national strength — tools to reclaim sovereignty, defend domestic workers, and reassert control over the disruptive forces of globalization. But when viewed through a wider lens — economic, institutional, and philosophical — that strength reveals itself as illusion.

Tariffs don’t just raise prices — they quietly corrode the systems that allow economies to thrive. They distort incentives, shrink global relationships, and dull the competitive edge that drives innovation, trust, and long-term prosperity.

In recent months, I’ve had a number of conversations about tariffs — some with clients, some with friends, many prompted by the current trade war. These conversations have been thoughtful, sometimes spirited, and always grounded in a genuine desire to understand what’s actually at stake.

In our common understanding, risk often appears as a single, dramatic event — a market crash, an economic recession, or a sharp correction. Yet this view misses the true nature of risk, which builds not through sudden breaks but through small, barely noticeable shifts beneath the surface of apparent stability. The real danger takes shape long before headlines announce it: the buildup of leverage, mounting deficits, overlooked correlations, and the quiet erosion of safety margins.

In an industry focused intensely on scale, I’ve chosen a different path: to stay small. Deliberately, strategically, and without apology. While many peers chase expansion, I’m pursuing something more elusive — a practice that serves my life rather than consumes it.

Marcus Aurelius did not write for fame or legacy nor to instruct future philosophers; his Meditations were private reflections, reminders to himself of virtue, resilience, and clarity amidst profound chaos. As Emperor of Rome, Marcus navigated relentless warfare, the devastating Antonine Plague, insurrection within his own ranks, and the profound grief of losing many of his children. His Stoic writings thus carry a unique credibility — tested and refined by the harshest realities of leadership and human suffering.

In the early 1980s, Intel was losing ground fast. Japanese competitors dominated the memory chip market, pushing Intel to the brink. Anxious boardroom discussions concerned a key question: clutch at the familiar or try something different? Andy Grove chose the latter. He pivoted Intel away from memory chips and redirected it into microprocessors — a gamble that ultimately saved the company.

In the summer of 216 BCE, the ancient Mediterranean world held its breath as two superpowers faced off in a battle for supremacy. The Roman Republic, desperate to end a string of humiliating defeats, staked everything on a single, massive confrontation. What followed was one of the most stunning tactical victories in military history. 

In The Art of Fugue, Bach’s final masterpiece, the music stops mid-phrase, a hauntingly unfinished conclusion that invites listeners to imagine what might have been. Here, Bach left no instructions for tempo or dynamics — just a structure, an intricate framework of interwoven melodies to be decoded, felt, and, with enough patience, understood. Bach’s compositions masterfully balance form and freedom, illustrating that a well-crafted investment portfolio, like his music, thrives on a similar balance between disciplined structure and agile adaptability.