Venture & Gain

Not your typical financial clickbait. Insights on wealth, investing, behavioral finance, markets, & more.

Hannibal’s Cannae Playbook: Ancient Lessons for Modern Investors
James W. Vermillion III James W. Vermillion III

Hannibal’s Cannae Playbook: Ancient Lessons for Modern Investors

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. 

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Counterpoint and Capital: Investing Lessons from Bach
James W. Vermillion III James W. Vermillion III

Counterpoint and Capital: Investing Lessons from Bach

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.

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The Fattening of the Pig: Loose Monetary Policy, Fiscal Stimulus, and the Investor's Dilemma
James W. Vermillion III James W. Vermillion III

The Fattening of the Pig: Loose Monetary Policy, Fiscal Stimulus, and the Investor's Dilemma

A pen of swine grumbles as they gorge at troughs overflowing with food. Their bellies swell, and their steps grow sluggish, but none pause to wonder why the feast is so plentiful. The hand that fills their trough is not one of kindness—it belongs to the augur, who knows that this momentary abundance is merely a prelude to sacrifice.

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Inflation Is Theft, But We Don't Have to Be Victims
James W. Vermillion III James W. Vermillion III

Inflation Is Theft, But We Don't Have to Be Victims

Inflation is theft. The loot isn’t just the lost dollar in your wallet or the rising price of your daily bread. It’s worse than that. By eroding the value of money, inflation also erodes our ability to plan for a better tomorrow. And while many try to complicate the causes of inflation, the reality is simple: it’s the result of reckless government policies — unchecked deficit spending and the endless expansion of the money supply.

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Returns to the Power of Time :  Morgan Housel on Compounding
James W. Vermillion III James W. Vermillion III

Returns to the Power of Time :  Morgan Housel on Compounding

Morgan Housel is one of the best financial storytellers of our time. His book, The Psychology of Money, stands out as a classic in a category flooded with subpar books, bad advice, and worse writing. In it, Housel explores the intersection of psychology and finance, offering invaluable insights into how our emotions and biases shape our financial decisions.

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How Karl Popper's Philosophy Transformed My Investing Mindset
James W. Vermillion III James W. Vermillion III

How Karl Popper's Philosophy Transformed My Investing Mindset

What if I told you the key to investing lies not in what we know but in embracing what we don't know and can never know with certainty? This paradoxical understanding is at the heart of Karl Popper's philosophy and has shaped my thinking about investing.

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Mythology: What Icarus Can Teach Us About Investing in Soaring Markets
James W. Vermillion III James W. Vermillion III

Mythology: What Icarus Can Teach Us About Investing in Soaring Markets

In Greek mythology, Icarus and his inventive father, Daedalus, attempted to escape from captivity on Crete by constructing wings of feathers and wax. Daedalus warned Icarus not to fly too close to the sun, as the heat would melt the wax. But Icarus, swept up in the rush of flight, disregarded his father's warning. Higher and higher, he soared, drunk on daring, until the sun melted the wax, and the wings disintegrated.

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Time Arbitrage: Fractal Markets and Financial Chaos
James W. Vermillion III James W. Vermillion III

Time Arbitrage: Fractal Markets and Financial Chaos

I like to periodically reset my thinking and get back to basics — whether simplifying my exercise regimen or rehashing philosophical principles. Recently, I felt the call to strip down investing and revisit fundamentals — to forget about valuation metrics, alpha, beta, and Monte Carlo simulations and think about investing from the ground up. What is investing? Why has it worked for so long? Will it continue to work in the future?

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Seeds of Bad Times: Ford’s Insights into Prosperity Traps
James W. Vermillion III James W. Vermillion III

Seeds of Bad Times: Ford’s Insights into Prosperity Traps

During the Great Depression, as the nation grappled with economic despair and uncertainty, Henry Ford stood at odds with President Roosevelt's New Deal, opposing initiatives like the 'Blue Eagle' campaign. His words prompt us to examine the mindset governing our investment decisions. It compels us to ask: How does prosperity cultivate the very conditions that precipitate future losses and crises?

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Retirement Reality Check: From Identity Death to Rebirth
James W. Vermillion III James W. Vermillion III

Retirement Reality Check: From Identity Death to Rebirth

Retirement is a flawed goal - or at least an incomplete one, often romanticized yet misunderstood in its complexity. Let's look at retirement not through statistics or theories but through the experience of a fictional retiree from Creative Edge Marketing Firm. These diary entries, a mix of imagination and real insights, reveal the surprising emotional landscape of post-work life.

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The Art of Economics: The Limits of Models in Human Market Dynamic
James W. Vermillion III James W. Vermillion III

The Art of Economics: The Limits of Models in Human Market Dynamic

During a recent visit to Paris, I decided to bypass the mobbed halls of the Louve, where the Mona Lisa resides, and head instead to the Rodin Museum. My visit was inspired by my desire to see Rodin's iconic sculpture - The Thinker. This masterpiece symbolizes the deep, often conflicting emotions of intense thought, embodying both the struggle and the bliss of contemplation.

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Change vs. Status Quo: Are We Hardwired for Caution?
Mindset James W. Vermillion III Mindset James W. Vermillion III

Change vs. Status Quo: Are We Hardwired for Caution?

We face major crossroads throughout our lives that shape our well-being and satisfaction - whether to quit a job, pursue more education, end a relationship, or change health habits like smoking or dieting. Yet, assessing whether we make optimal choices at these junctures is remarkably difficult.

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The Facebook Phenomenon: Fueled By Network Effects
Investing James W. Vermillion III Investing James W. Vermillion III

The Facebook Phenomenon: Fueled By Network Effects

In 2004 a website emerged that would change the fabric of online interaction. It was called "TheFacebook."

But the real growth began when Facebook opened its virtual doors to high school students. This move propelled Facebook's user base to new heights, unleashing a phenomenon known as "network effects."

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Occam’s Razor: Cutting Through Complexity in Finance
Mindset James W. Vermillion III Mindset James W. Vermillion III

Occam’s Razor: Cutting Through Complexity in Finance

We overcomplicate things. Even simple concepts are twisted and tangled into complicated webs of ideas. This is not simply a matter of personal observation; it is a cognitive bias known as complexity bias. My favorite tool to combat our tendency to overcomplicate matters is Occam’s Razor.

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From Carriage to Car: The Transformative Power of Creative Destruction
Investing James W. Vermillion III Investing James W. Vermillion III

From Carriage to Car: The Transformative Power of Creative Destruction

The term “creative destruction” was coined by economist Joseph Schumpeter (1883–1950), capturing the seemingly paradoxical nature of progress. It encapsulates the chaotic and unpredictable essence of the free market, where established industries crumble, fresh ones emerge, and agile startups seize opportunities while established giants falter.

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The Map is Not the Territory: Understanding the Model to Reality Gap
Mindset James W. Vermillion III Mindset James W. Vermillion III

The Map is Not the Territory: Understanding the Model to Reality Gap

Maps are abstractions of reality - a reduction of what they represent. This reduction is necessary but inherently flawed. Even the most precise maps do not fully and accurately depict the territory they represent. This is true, too, of the mental maps we've charted through our experiences and beliefs that help us simplify an intricate reality into something comprehensible.

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Can a Flutter Spark a Storm? The Butterfly Effect and Financial Markets
Mindset James W. Vermillion III Mindset James W. Vermillion III

Can a Flutter Spark a Storm? The Butterfly Effect and Financial Markets

Can a butterfly flapping its wings in Brazil trigger a tornado in Texas?

In 1961, Edward Lorenz, an American mathematician and meteorologist, studied weather patterns and developed computer models to forecast weather conditions. During his research, he made a remarkable discovery. He observed that even the slightest changes in the input parameters of his model resulted in significantly different outcomes. He coined this phenomenon “sensitive dependence on initial conditions," meaning that minor variations in the initial conditions could lead to significant differences in forecasted weather patterns.

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Beyond the Bell Curve: The Black Swan's Impact on Investing
Investing James W. Vermillion III Investing James W. Vermillion III

Beyond the Bell Curve: The Black Swan's Impact on Investing

During the 17th century, courageous adventurers set sail across uncharted waters in pursuit of the unknown. Among these daring souls was Willem de Vlamingh, a Dutch explorer whose remarkable journey took an unexpected turn upon reaching the distant shores of present-day Western Australia.

On the 10th of January in 1697, de Vlamingh and his crew found themselves captivated by a scene that defied everything they thought they knew. As they embarked on an excursion up a mysterious river, little did they know that what awaited them would shatter their preconceived notions and send shockwaves through the annals of natural history.

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Second-Order Thinking: The Path To Better Investing Decisions
Investing James W. Vermillion III Investing James W. Vermillion III

Second-Order Thinking: The Path To Better Investing Decisions

The process of thinking is often equated to a reflex. Just as our hearts beat without our direction, we shiver uncontrollably when our body temperature drops and our eyes blink 15–20 times per minute to lubricate our eyeballs and keep debris at bay, so too does our mind seem to operate on its own accord. We may not be aware of the specific neural pathways activated when we think, but we experience the thoughts as if they were happening to us. This seemingly effortless mental operation corresponds to what is termed first-order thinking.

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From SpaceX to Portfolios: Harnessing First-Principles Thinking for Investment Success
Investing James W. Vermillion III Investing James W. Vermillion III

From SpaceX to Portfolios: Harnessing First-Principles Thinking for Investment Success

The intricacies of the human mind, coupled with the complexities of our surroundings, present difficulties in making sense of the world around us. As a result, we have devised mental frameworks that serve as invaluable tools for enhancing decision-making in investing and the broader scope of life. One of these frameworks is first-principles thinking.

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