How G2’s Josh Goldberg Beat the Odds and Built a Winning Investment Process
Adapted from Stock Market Maestros: The winning habits, strategies, and mindsets of the world’s best investors, published by Harriman House in March 2026 (Order now).
By Lee Freeman-Shor and Clare Flynn Levy
Lee Freeman-Shor is the author of the international bestseller, The Art of Execution: How the world’s best investors get it wrong and still make millions, named by Investing By The Books as one of the “Top 20 Investment Books Ever.” Before becoming a writer, the Citywire 1000 report recognized Lee as one of the world’s top fund managers. His flagship fund received a Gold rating from S&P Capital IQ and the top (AAA) rating by Citywire.
Clare Flynn Levy is CEO & Founder of Essentia Analytics. Prior to setting up Essentia, she spent ten years as a fund manager, in both active equity (running over $1B of pension funds for Deutsche Asset Management), and hedge (as founder and CIO of Avocet Capital Management, a specialist tech fund manager).
What does a “mission impossible” look like in the investment world?
For hedge fund manager Josh Goldberg, it has taken more than one form.
The first came in 2009, when Goldberg launched his firm, G2 Investment Partners, with less than $10 million under management. He was told that the odds of a hedge fund like his reaching $100 million were less than one in 500.
The second came a few years later, when he was diagnosed with stage-four colon cancer and given only a two percent chance of survival.
In Stock Market Maestros, we profile twelve investors who don’t just pick good stocks, they also know how to run their winners and cut their losers before they spiral out of control. Order now.
Against those odds, Goldberg did much more than just survive. Through grit, hard work and discipline, he eventually beat cancer — and his fund produced performance strong enough to rank among the best in its peer group.
Goldberg is one of the twelve investors profiled in Stock Market Maestros, selected through Essentia Analytics’ Behavioral AlphaⓇ analysis for demonstrating exceptional investment decision-making skill. In the chapter devoted to Goldberg, titled Mission(s) Impossible — 009 (Lives), we examine the philosophy and execution discipline behind his approach to investing.
At the heart of Goldberg’s strategy are two clear ideas: Focus on companies that are surprising the market, and know when to exit them, whether winning or losing.
Goldberg and his team concentrate on identifying companies whose earnings results begin to diverge from analyst expectations. Rather than trying to get ahead of the first surprise, Goldberg waits until it has already occurred. Only then does the team begin its deeper research, asking whether the market has fully adjusted its expectations — or whether further surprises may still lie ahead.
The strategy reflects a behavioral insight. Analysts and investors often anchor to existing forecasts and revise them only gradually when new information emerges. That adjustment process can unfold over several quarters. The key is to be invested during that period, while the gap between reality and expectations persists – but not too long, or you run the risk of round-tripping big winners. To that end, Josh has a golden rule that dictates how long he should hold a winning stock — a rule that means he has won big while buy-and-hold investors would have round-tripped and given back all the gains they had made in the same stock.
Much of this work takes place in small-cap companies, where coverage is limited and market inefficiencies can be more pronounced. Goldberg and his research team spend significant time meeting with management teams, analyzing operating trends, and forming what he calls a “variant perception” — a view about the company that differs from the market consensus.
At the same time, Goldberg applies strict rules to managing losers. One of the most important is that no single investment should cost the fund more than one percent of capital if it fails. That discipline forces the team to cut losing positions before they become destructive to overall performance.
Essentia’s Behavioral Alpha analysis highlights the results of that discipline. Goldberg’s Behavioral Alpha Score of 55.5 reflects consistently skilled decision-making across picking, sizing, and timing decisions. His hit rate of 55 percent shows that he gets more ideas right than wrong, while his payoff ratio of 171 percent demonstrates that his successful investments tend to generate significantly more value than his losing ones subtract.
Taken together, those statistics point to a manager who combines strong idea generation with careful control of risk and position management.
Stock Market Maestros explores Goldberg’s approach in greater detail, walking through the investment decisions, rules, and behavioral insights that shape his process.
Goldberg’s story — both personal and professional — is dramatic, but the lesson is practical. In markets that constantly test conviction and discipline, a clear, faithfully-executed process can make the difference between surviving a challenging environment and thriving within it.
Stock Market Maestros: The winning habits, strategies, and mindsets of the world’s best investors is published by Harriman House. Get your copy now!
About Essentia Analytics
Essentia Analytics is the leading provider of behavioral data analytics services to professional investors and allocators of capital. Led by a team of experts in investment management, technology and behavioral science, Essentia combines next-generation decision attribution analytics technology with human coaching to help both equity fund managers and allocators identify investment skill and bias — and capture performance that was previously being lost to decision-making deficiencies.
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