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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this captivating episode, Patrick O'Shaughnessy sits down with Sam Hinkie, former NBA executive turned venture capitalist at 87 Capital. Hinkie reveals his unconventional approach to discovering exceptional talent through "digital breadcrumbs" (12:35) — the trail of insights, blog posts, and work people leave behind online. He shares how this strategy led him to hire a future Rockets assistant GM based purely on outstanding blog posts (19:42), and explains why slowing down the evaluation process drives away transactional people while attracting those ready for deeper partnerships (37:57). The conversation explores building trust through long-term relationships, the power law nature of talent, and how NBA lessons translate to venture investing—offering both investors and entrepreneurs a masterclass in identifying and nurturing exceptional people.
Former President and GM of the Philadelphia 76ers and current founder of 87 Capital, a venture capital firm. Previously spent over a decade in the NBA with the Houston Rockets, bringing data-driven investing principles to basketball operations. Known for his analytical approach to talent evaluation and long-term strategic thinking.
CEO of Positive Sum and host of Invest Like The Best podcast. Author and investor focused on backing founders transforming markets. The show has established itself as one of the leading podcasts for business strategy and investment insights.
Stop asking surface-level questions—find something the candidate cares about and drill relentlessly until you hit bottom. The best hires reveal intellectual humility about their knowledge limits while demonstrating genuine depth in their passion areas. (07:00) You're not just evaluating; you're learning from every person across from you, and that curiosity creates the most revealing interviews.
Follow the trail of someone's thinking across years—their GitHub repos, medium posts, highlighted articles, even YouTube videos from age 16. (12:35) One founder's parents' interviews and seven years of YouTube content revealed a pattern of systematic thinking that no traditional interview could uncover. The middle of that distribution across 30 years is who they really are.
PowerPoint decks are static snapshots—invest in trajectories instead. (16:09) The best operators get down learning curves quickly, often bringing beginner's minds to sleepy industries where incumbents believe "software will never disrupt us." Look for people who are wildly pointy in one dimension while being transparent about their weaknesses and treating them as solvable future problems.
Build relationships by consistently doing things in others' best interests, not your own. (53:03) Tell people hard truths that aren't transactionally beneficial to you. The harvest from decades of fewer, deeper relationships creates a network where your phone becomes a "treasure trove" of people sending breakthrough insights and asking for real guidance on big decisions.
Structure your environment so 70-90% of your time is spent with stunning colleagues you actively chose. (48:48) If you're naturally patient and think in decades, build systems where that temperament compounds into competitive advantage rather than fighting against momentum-driven cultures that reward short-term thinking.