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

This Issue at a Glance

Sam Hinkie, former Houston Rockets executive, President and General Manager of the Philadelphia 76ers, now founder of venture capital firm Eighty-Seven Capital. The core thread of this issue: how to evaluate someone's growth trajectory by tracking the "digital breadcrumbs" (behavioral tracks, decision records) they leave behind, thereby filtering out people and investments truly worth long-term partnership. Sam Hinkie argues that in investing and talent selection, people mistakenly overvalue static PPTs (“points”) while severely undervaluing the growth path and cognitive depth revealed by historical behavioral tracks (“lines”)—because the former is a snapshot in time, while the latter is a real signal across a time series.

Thematic Sections

1. Digital Breadcrumbs: The Most Underrated Tool for Evaluating People

Sam Hinkie believes that the public behavioral traces a person has left behind (blogs, GitHub, Twitter, Medium likes, even YouTube videos) are more reliable evaluation material than any face-to-face conversation.

• Mechanism Breakdown: Sam divides his "digital breadcrumb" strategy into two categories—one is traces left unintentionally (e.g., forum posts from years ago), the other is what he actively solicits (e.g., "please send me the book that has influenced you the most"). He often reads founders' college theses, old blogs, and even Medium like records from years ago. He gives a specific example: for Shrey, founder of ScoutApp.ai, he watched videos of his parents talking about his life journey, read his Medium articles and like records over the years, and also looked at another founder's YouTube channel (updated consistently over the past 7-8 years) to judge their thinking evolution trajectory.
• Historical Context: Sam recalls how he discovered current Rockets Assistant General Manager Eli Whiteis through "breadcrumbs" in 2008. Eli initially published high-quality analysis under a pseudonym on the basketball analytics forum APBR metrics, and later started a blog. Sam says: "After the first blog post, 4-5 people forwarded it to me within a day... The second one, same thing... By the third, I had printed it out, walked into Daryl Morey's office and said, 'I want to hire this person today.'" The key judgment criterion was not what Eli said, but his ability to consistently produce high-quality analysis—this proved he had "a fast learning speed" and "extreme passion," two traits that cannot be directly verified in an interview.
• Reasoning & Signals: Sam believes the advantage of this method is seeing a "time series"—how a person's thinking evolved at ages 20, 25, and 30. He explicitly says: "This doesn't mean you agree with everything they thought in the past. No one would agree with everything I thought at 25. But you can see where they came from, and how they've grown."

2. Deep Interviews: Finding People Who Are "Bottomless"

Sam Hinkie believes the core of an interview is not to judge what the person knows, but to understand how they think—and the most effective test is to "pick a topic and keep drilling down to see if you can hit the bottom."

• Mechanism Breakdown: Sam's interview style is "off-script." He starts from a topic the other person is interested in and keeps asking "why" and "what else" until he reaches the boundary of their cognition. He particularly appreciates two types of people: those who can clearly say "I'm only at 70% in this area, not an expert" (self-awareness), and those you can never drill to the bottom of (extremely deep cognition).
• Data Chain: When asked how many people are worth the time to deeply understand, Sam gives a precise ratio: "If you're lucky, you'll meet 1-2 such people a year. You add them to your circle and walk through life together." He also stresses that he cherishes his chosen time extremely: "If I choose to spend 30 minutes with you, that is the best use of my time at that moment."
• Falsification Condition: Sam says the type he dislikes most is the "transactional" person—those who want to make an investment decision in 7-8 minutes. His counter-strategy is to "slow down"—"Slowing down drives transactional people crazy, which suits me just fine."

3. Talent Follows a Power Law: The Top 1% Can Change Everything

Sam Hinkie believes that in sports and investing, the best talent follows a power law—the best person can disproportionately change the fate of the entire system.

• Historical Context: Sam uses the NBA example to illustrate this point—LeBron James led his team to the Finals for 10 consecutive years (when healthy). But he also acknowledges that as a company grows larger, market choice becomes more important: "As the company scales, the market's choice is indeed as important as the founder." Yet he insists that early hires "propagate"—the person you hire influences the next person you hire, creating a self-reinforcing effect.
• Mechanism Breakdown: Sam believes the best leadership comes not from position but from the quality of relationships. He quotes an analogy: "When your child is 2, you are a benevolent dictator; when they are 25, your influence on them depends only on the quality of your relationship." He advises founders: "You are the CEO, but your CTO could leave, and your 7-person engineering team would collapse. You have no command authority over her, only influence. You need to invest in the quality of the relationship now."
• Specific Case: Sam recalls the first training session after James Harden was traded to the Rockets. After the coach blew the whistle, Harden said to the whole team, "Tuck your shirts in," and then tucked his own in first. All 14 players did it. Sam says: "At that moment, the new alpha arrived. The uncertainty lasted about 45 seconds, then the signal was sent—there is a new way of doing things."

4. Designing the Game: Letting Patience and Long-Term Thinking Be Rewarded

Sam Hinkie believes that the core guiding principle behind founding Eighty-Seven Capital is to design a "game" where patience, long-term thinking, and deep relationships are systematically rewarded, rather than penalized by short-term market pressures.

• Self-Design: Sam explicitly lists the three goals he designed: 1) Spend 80-90% of his time with "amazing colleagues"; 2) Leverage the foresight of "seeing around corners" (rather than doing short-term momentum trading); 3) Have a calm, stable temperament be rewarded. He says: "I am very stable, sometimes to the point of being annoying. I am hard to get fired up. I don't mind holding my own views in isolation for a long time."
• Mechanism Breakdown: Sam believes the "game" he designed is "thinking in decades"—"I am trying to compound wisdom and trust, trying to better understand life and business because I'm curious about them." He chooses to keep the fund size small (first fund $50 million, and he may keep it small long-term) because he believes a deep relationship network of "hundreds" is more valuable than a shallow network of "thousands."
• Falsification Condition: Sam acknowledges that his "long-termism" is not something everyone can agree with. He cites a self-deprecating example: his son was only 2 years old when he was already researching Texas regulations on "whether children should delay starting school by a year" and called the principal to ask. After listening, the principal said: "Sir, your son is only 2. He lives in this school district, with you, and you care about him—he'll be fine." Sam admits: "In that moment, I was humbled by my own relative lack of perspective."

5. Long-Term Thinking: Caro's "87 Votes" and the Game of Power

Sam Hinkie believes that Robert Caro's biographies are the best illustration of the "long game"—how a person can spend decades, sacrificing everything, to win a seemingly impossible race.

• Historical Context: Sam named his fund "87 Capital" after a story from Caro's The Path to Power series, volume two Means of Ascent: in 1948, a candidate (Lyndon B. Johnson) won a seemingly insignificant election by 87 votes, setting himself on the path to the presidency; the candidate who lost, however, "won back his life and his family." Sam says: "It reminds me that we are looking for winners, but winning doesn't just depend on who wins; it depends on what you are counting."
• Mechanism Breakdown: Sam believes Caro's core insight is "power reveals" rather than "power corrupts": "When you have a certain amount of power and wealth, it reveals your true nature—you can do the things you always wanted to do but were constrained from doing." The lesson he draws from this: if you want to win an extremely intense competition, you must assume someone will be willing to "sacrifice everything—time, money, relationships, morality." If you are not willing to pay that price, assume someone else will.
• Specific Case: Sam describes a scene from Caro's book: after JFK was assassinated, LBJ sat behind a curtain in a Dallas hospital for 90 minutes without speaking, thinking. When told the president was dead, he immediately issued a series of orders—reportedly a list of hundreds of items, in the correct order, covering the next 50 days of governance. Sam says: "Can you imagine a more stressful situation than that? And he designed a principle-based list, like a checklist, covering hundreds of items, in the right order, knowing which chaos to bypass and which were the key issues."

Mentioned Positions

Position	Guest Attitude	Key Data
ScoutApp.ai	Invested, positive	Founder Shrey's Medium and GitHub history deeply analyzed; another founder has 7-8 years of YouTube video history
Eli Whiteis (Rockets Assistant GM)	Former employee, highly regarded	Discovered via APBR metrics forum and blog; forwarded by 4-5 people on day one; ultimately worked at the Rockets for 12 years
James Harden	Positive case	Traded to the Rockets at age 23; demonstrated leadership in first training session ("tuck your shirts in"); subsequently delivered consecutive high-scoring performances
Stripe / Collison brothers	Positive assessment	Mentioned as typical example of "adding footnotes while thinking"
Marc Andreessen	Positive assessment	Mentioned as typical example of "thinking differently"
Naval Ravikant	Positive assessment	Mentioned as typical example of "having a large number of original cognitive modules"
Patrick McKenzie	Positive assessment	His blog described by Sam as a "diamond mine," requiring a decision on reading order
Notion / Airtable	Industry observation	Representative companies in the "no-code" trend, but seen as a threat by large companies like Microsoft
Twilio	Industry reference	Typical example of an API infrastructure company; recommended "don't build your own payment system, use Twilio"
Bottomless	Investment target	Position not explicitly stated, but Sam is an investor; its CEO's views quoted ("the internet is a space of infinite possible behaviors")

Judgments Worth Remembering

1. Sam Hinkie: People should invest in "lines" rather than "points"—invest in a person's growth trajectory, not a static PPT snapshot. Support: He evaluates a founder's growth trajectory by reading years of their Medium, GitHub, and YouTube history, rather than relying on a 20-minute presentation.

2. Sam Hinkie: You can "not value interviews" while still doing "the best interviews." Support: He believes interviews provide a weak signal, but if you do them, you should pick a topic and keep drilling down to see if the other person can find a "bottom"—if they can't, it means sufficient cognitive depth; if they hit bottom in a few sentences, it's just surface-level work.

3. Sam Hinkie: The most effective leadership comes from the quality of relationships, not hierarchical position. Support: Analogy to parenting—when your child is 2, you are a dictator; when they are 25, you can only influence them based on the quality of the relationship you built. A founder also has only "influence" over their CTO, not command authority.

4. Sam Hinkie: The best response to a "transactional" person is to "slow down." Support: If someone demands "you must decide by Friday," he says directly "I'm not playing." He believes long-term trust takes time to accumulate, and transactional people are incompatible with that value.

5. Sam Hinkie: Caro's "power reveals" rather than "power corrupts" is the core insight—meaning when a person has "F-you money," their true nature emerges. Support: He cites Caro's portrayal of LBJ and Robert Moses, both of whom sacrificed everything to win the game, and only after winning can you see what they truly wanted.

6. Sam Hinkie: The best approach is to "write it down"—make your thinking a searchable "breadcrumb" that others can discover. Support: As Stripe's Patrick Collison said, write it down for "employees not yet born." Writing is the way to "make humans readable by the internet," so the right people can find you.

7. Sam Hinkie: In a fiercely competitive game, if you are unwilling to pay the "price," assume someone else will. Support: The characters in Caro's books sacrificed time, money, relationships, and morality to win the presidency; if you are unwilling to pay, don't enter that game.

8. Sam Hinkie: In investing, focus on "1.5%" capital gains, not "15%" paper returns. Support: He cites the naming origin of Eighty-Seven Capital—LBJ won an election by 87 votes in 1948, changing his life forever; but the losing candidate won back his life and family—the key is "what you are counting."