Invest Like the Best with Patrick O'Shaughnessy
Invest Like the Best with Patrick O'Shaughnessy

Sam Hinkie – Find Your People - [Invest Like the Best, EP.204]

My guest today is Sam Hinkie. Sam worked for more than a decade in the NBA with the Houston Rockets and then as the President and GM of the Philadelphia 76ers. And now, after years of personal investing, he has launched his own venture capital firm, Eighty-Seven Capital. Every conversation I have wi

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Episode Summary

Executive Summary: Patrick O’Shaughnessy interviews Sam Hinke about how to evaluate people, build trust, and invest in founders. Hinke argues that great outcomes come from studying breadcrumbs—writing, digital traces, behavior under pressure, and long-term patterns—to find exceptional, evolving people and align with them early.

Main Topics: Interviewing as curiosity, not interrogation (Priority: 5/5): Hinke uses interviews to understand how people think, learn, and see limits—not to trap them. Breadcrumbs as predictive evidence (Priority: 5/5): He studies writing, blogs, code, and old posts to infer trajectory and character over time. People as power-law assets (Priority: 5/5): He believes a few exceptional people drive outsized results in teams, companies, and countries. Trust, alignment, and relationships (Priority: 5/5): Durable influence comes from compounding trust and matching roles to personal incentives. Lessons from basketball to venture capital (Priority: 4/5): Sports taught him to zoom out, value edge erosion, and bet on pointy talent that can evolve. APIs, no-code, and outsourcing complexity (Priority: 4/5): He sees software increasingly broken into specialized services and tools built for software. Writing as a breadcrumb for others (Priority: 4/5): Publishing clear thinking helps future colleagues and founders find and understand you.

Key Arguments: Interviews should match who someone is with where they want to go, not test trivia. Digital breadcrumbs reveal long-term thinking better than a single meeting or slide deck. Exceptional people are rare; he may add only one or two truly special people a year. Trust compounds when you act in the other person’s interest and tell hard truths. Great leaders influence through relationships, not just hierarchy or command-and-control. In venture, the main bet is on people who can learn fast and evolve as the game changes. APIs and no-code tools will keep replacing internal software work because specialization wins.

Data Points: Number of applicants for the hiring process: 500 - Patrick says the final job candidate pool came from 500 applicants. Final candidates interviewed: five or so - Patrick describes the last stage of the hiring process. Expert calls on Tegas: more than 10,000 calls - Tegas offers instant access to a large call library on many companies. Price per expert call on Tegas: $300 per call - Tegas advertises lower-cost expert calls than typical networks. Founder-friendly fund size: $50 million fund - Hinke says 87 Capital’s first fund is a $50 million fund. Time at Rockets / Eli Whiteus tenure: 12 years - Hinke notes Eli has been at the Rockets for 12 years. LeBron finals streak: 10 - Hinke estimates LeBron’s team had been to the finals 10 straight years when healthy. Typical annual addition of close people: one or two people a year - Hinke says truly resonant people are added very rarely. Phone size of his relationship network: hundreds, not thousands - He wants to compound trust with a small set of people over time. No-code market size proxy: 25 million developers on the planet and a billion spreadsheet users - Hinke uses this contrast to show the scale of no-code opportunity. First blog discovery example: 2008 - He says he discovered Eli Whiteus’s work around 2008.

Pivotal Quotes: "All interviewing should be a matchmaking game of who they are and how they see themselves and where they want to be." — Sam Hinke: Explaining his philosophy of interviews and hiring. "People are really a power law and the best ones can change everything." — Sam Hinke: Describing why he concentrates on exceptional individuals. "Write, write and put your thoughts out, particularly if you're proud of them, particularly if you want to make them better." — Sam Hinke: Advice on creating useful breadcrumbs for others.

Implications: For founders and investors, the edge is in patience, written proof of thinking, and choosing people whose trajectory compounds over years.

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