Our Published Work

Insights

Process / Philosophy

October 15, 2026

Margin of Safety: The Principle That Separates Investing from Speculation

Uncertainty can’t be eliminated, but it can be prepared for. Part four of our Free Solo series explains why margin of safety is the only reliable way to manage risk, and why investing without one is really speculation.

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Process / Philosophy

September 15, 2026

Fear, Greed and the Investor Brain

Fear and greed are the two emotions that move markets — and the two most likely to derail sound investing. Part three of our Free Solo series looks at the cognitive biases, from loss aversion to the endowment effect, that distort how investors perceive risk.

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Process / Philosophy

August 15, 2026

You Can’t Manage What You Don’t Understand

Before you can manage risk, you must understand what it actually is. Part two of our Free Solo series looks at why volatility is the wrong proxy for risk — and offers a clearer, more useful definition.

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Process / Philosophy

July 15, 2026

What a Free Solo Climber Can Teach Us About Managing Investment Risk

Alex Honnold’s free solo ascent of El Capitan reveals a masterclass in risk management — the first post in our six-part series on DGI’s framework for managing investment risk.

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Updates

February 12, 2026

The Road to Albuquerque

Year-End 2025 Investment Update — examining what drove narrow momentum-led markets, why our process did not change, and why we remain constructively optimistic.

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Equity Markets

August 11, 2025

The Curious Case of Stock Price Drawdowns

Inspired by Sherlock Holmes — do large drawdowns reliably signal poor future returns, or are investors theorizing before examining the evidence?

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Process / Philosophy

May 7, 2025

The Financial Laws of Gravity

Just as Newton's apple always fell downward, there are irreducible investment truths that reliably pull stock prices toward intrinsic value — the four financial laws of gravity.

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Companies

June 30, 2024

Artificial Intelligence: Investing in Technology Transformations

AI is not one company or one moment — it is a technology transformation decades in the making. DGI separates durable investment opportunities from speculative noise.

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Milestone Piece

June 2023

Free Solo

What does it mean to commit fully to an idea with no rope? A look at conviction, preparation, and asymmetric risk in investing.

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Process / Philosophy

August 2021

Fishing With My Dad

A father’s decades-long fishing discipline — grounded in fundamentals, patience, and a proven process — turns out to be a remarkably powerful blueprint for long-term investment success.

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Process / Philosophy

December 2020

Three Questions

At the core of any sound investment process is a clear understanding of what investors can and cannot control. Three questions define the only levers we have for directly influencing our investing outcomes.

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Updates

April 2020

COVID-19

DGI’s real-time thinking on what the pandemic crisis meant for markets, for portfolio companies, and for long-term investors — written in the thick of it, April 2020.

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Updates

March 2020

A Dog Named Cisco

When a prospective client named her dog after Cisco Systems stock, it sparked a lifelong lesson in the great company/lousy stock syndrome — and why price always matters.

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Updates

February 2020

Year End Thoughts (2019)

Three clear investment messages from a year that spoke loudly — a portfolio with gas in the tank, the dangers of S&P 500 concentration, and the absurdity of negative bond yields.

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Process / Philosophy

September 2018

Risk & Return

Risk and return are the twins of investing. A deep look at actual vs. perceived risk, margin of safety, and why most investors get the balance fundamentally wrong.

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Updates

February 2019

1987 Redux?

The Q4 2018 selloff drew parallels to Black Monday — DGI examines the role of financial intermediaries, the rise of hedge funds and index funds, and why the selloff was an opportunity.

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