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When selecting new GPs to back, Brian Singerman uses a powerful heuristic: could this person, playing their own unique game, have beaten him at his peak as a VC? This test cuts through superficial metrics to identify raw, world-class talent, irrespective of their specific investment strategy.

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Investor Viktor Orlovsky reveals his mental model for evaluating founders: he compares new prospects to his "role models" of obsession and leadership. This method of pattern-matching against successful archetypes from his portfolio helps him decide who to back.

In a world of highly skilled money managers, absolute skill becomes table stakes and luck plays a larger role in outcomes. According to Michael Mauboussin's "paradox of skill," an allocator's job is to identify managers whose *relative* skill—a specific, durable edge—still dominates results.

Singerman dismisses standard VC practices like reserve calculations and ownership targets as "nonsense." He argues that to truly beat the market, a firm must abandon these rules and concentrate as much capital as possible into its highest-conviction companies, creating extreme, fund-defining outcomes.

Brian Singerman's venture strategy was almost entirely focused on founder assessment, making up over 98% of his decision. He famously doesn't read financial reports or use spreadsheets, instead concentrating all his effort on one question: is this founder the best in the world at something novel?

A powerful, often overlooked, due diligence signal for a fund is the quality of its junior team. Great managers attract, retain, and effectively communicate their vision to top young talent. By networking with peers, investors can gauge if a firm is a talent magnet, which strongly indicates the quality of its leadership and future prospects.

Ben Horowitz argues that waiting a decade for fund outcomes is too slow. Instead, a16z judges investors "at the point of attack"—how good they are at finding and winning deals with exceptional founders. This focuses on decision quality in the present, not lagging indicators.

Swell VC's Rusty Ralston shares that the most insightful LPs probe a GP's character, values, and personal history. For multi-decade investment relationships, understanding the person is foundational to establishing the trust, character, and integrity required for long-term success, surpassing the importance of typical fund metrics.

Instead of focusing on process, allocators should first ask managers fundamental questions like "What do you believe?" and "Why does this work?" to uncover their core investment philosophy. This simple test filters out the majority of firms that lack a deeply held, clearly articulated conviction about their edge.

Relying on an established VC's past performance creates a false sense of security. The critical diligence question for any manager, emerging or established, is whether they are positioned to win *now*. Factors like increased fund size, team changes, and evolving market dynamics mean a great track record from 5-10 years ago has limited predictive power today.

An effective manager evaluation technique is to recognize that everyone presents their polished "best self" initially. An allocator's primary job during due diligence is to actively investigate beyond this facade to uncover the manager's "true self"—how they operate under pressure and handle failure—before committing capital.

Evaluate Emerging Fund Managers By Asking: "Could They Have Beaten Me In My Prime?" | RiffOn