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Invest Like the Best with Patrick O'Shaughnessy
Invest Like the Best with Patrick O'Shaughnessy•September 9, 2025

Sam Hinkie - Find Your People - [Invest Like the Best, REPLAY]

Sam Hinkie discusses the importance of finding and nurturing relationships with exceptional people, emphasizing how tracking someone's digital breadcrumbs and understanding their thinking can help identify talent with high potential. He shares insights from his experiences in sports and venture capital, highlighting the value of intellectual curiosity, long-term perspective, and building trust through genuine interest in others.
Solo Entrepreneurs
Corporate Strategy
Startup Founders
Venture Capital
Patrick O'Shaughnessy
Sam Hinkie
James Harden
Eli Witus

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Compelling StoriesPremium
  • Strategies & FrameworksPremium
  • Thought-Provoking QuotesPremium
  • Statistics & Facts
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Similar StrategiesPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
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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.

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Podcast Summary

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.

Speakers

Sam Hinkie

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.

Patrick O'Shaughnessy (Host)

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.

Key Takeaways

Drill Down to the Learning Core

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.

Hunt Digital Breadcrumbs Like a Detective

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.

Hire Arrows, Not Dots

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.

Compound Trust Through Unconditional Investment

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.

Design Systems That Reward Your Natural Temperament

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.

Compelling Stories

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Statistics & Facts

  1. 75% of the world's top hedge funds trust AlphaSense as their market intelligence platform, which provides access to over 500 million premium sources including company filings, broker research, and news. (01:02)
  2. AlphaSense's recent acquisition of Tigus includes the world's largest library of expert interview transcripts, with over 200,000 calls covering more than 24,000 public and private companies. (01:14)
  3. In the API and no-code movement, there are approximately 25 million developers on the planet compared to 1 billion spreadsheet users, highlighting the massive potential for democratizing development tools. (55:34)

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Similar Strategies

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

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