Letters to a Young Investor: Mike Maples, Jr.

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Friends,

At its core, “Introduction to Poetry” by Billy Collins is about the difference between the drive to define something and the drive to understand it. In a few sparse lines, Collins contrasts the way he wishes readers would appreciate poetry with the manner in which so many do so. Rather than appreciating its contours and marveling over its intricacies, most readers prefer to pummel a poem for information. Instead of holding it to the light “like a color slide” or “waterski[ing]” across its surface, they “begin beating it with a hose/to find out what it really means.” In their drive to define the work in front of them – to analyze and probe it – Collins’ readers neglect its beauty, and miss what really makes it tick.

Though Collins is talking about poetry, he could just as well have been describing any craft. No matter the discipline, there is always this tension between defining and understanding, controlling and observing, grasping and witnessing.

When it comes to the craft of venture capital, Mike Maples, Jr. is one of its great appreciators. Over the past two decades, the Floodgate co-founder has built a remarkable track record by attuning himself to the frequency of great entrepreneurs, observing their quirks, and seeking to understand. As Mike himself describes it, his praxis is not about thinking faster or exhaustively analyzing a market, but simply listening differently. That approach has allowed Mike to make many outlier investments long before they broke out, backing Twitter, Twitch, Okta, and Applied Intuition in their messy infancies.

As part of The Generalist’s “Letters to a Young Investor” series, we’ll explore the nuances of Mike’s craft. To learn how one of the best early-stage investors of the past twenty years spots the future and identifies anomalies, read on. To enjoy the full correspondence and the rest of The Generalist’s exclusive interviews, join as a premium member for just $22/month. For the price of a single business lunch, you’ll unlock the strategies of some of the world’s best investors, founders, and operators.

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