This podcast features three experts on people, life, and investing. Sam Hinkie (ex-NBA exec) says to judge someone by their 'digital breadcrumbs'—old blogs, papers, GitHub—not just interviews. Boyd Varty (South African wilderness guide) compares life to tracking animals: don't wait for the full path, just find the first footprint and follow your gut. Charlie Songhurst (ex-Microsoft, 483 investments) found that scaling from 10 to 100 people, good companies see only 15% drop in per-person output, bad ones drop over 90%. He advises avoiding 'fun and complex' areas (like space) and investing in 'boring and complex' ones (like audit software) where there's less competition.
This episode of Invest Like the Best features curated highlights from three guests. Sam Hinkie emphasizes using "digital breadcrumbs" to deeply understand others, avoiding transactional relationships, and optimizing one's career from an investment perspective. Boyd Varty draws parallels between trac
This edition of Invest Like the Best features curated dialogues with three distinguished guests: former NBA executive Sam Hinkie (now founder of 87 Capital) on using "digital breadcrumbs" to deeply assess character and avoid transactional relationships; South African wilderness guide Boyd Varty, who draws parallels between tracking wildlife and life and investing, introducing the concept of "cleaning up chaos for others"; and former Microsoft strategy head Charlie Songhurst, who distills a phased filter for startup success and failure based on experience with 483 companies. The most impactful insight in the episode comes from Charlie Songhurst: when a startup scales from 10 to 100 employees, unit output at strong companies drops only 15%, while at poor companies it declines by over 90% — the ability to manage scaling is the most critical filter separating success from failure.
Sam Hinkie believes that finding and retaining top talent is the highest-return activity in both investing and life, and that "digital breadcrumbs" are the most underrated strategy for identifying such individuals.
Hinkie's core conviction is that "people also follow a power-law distribution" — top talent attracts more top talent, compounding over time. His original intent in designing 87 Capital was to ask, "Can I create a world where I spend almost all my time with exceptional people?" He pursues "fewer but deeper relationships," aiming not to manage thousands but to build long-term compound trust with 10–50 core individuals.
The Digital Breadcrumb Strategy: Hinkie actively seeks out the historical traces a person leaves behind — college papers, blogs, Medium highlights, GitHub repositories, YouTube videos. He believes this is far more efficient than interviews: "If you had someone evaluate me every year from age 12 to 42, the distribution in the middle is who I am." He cites the example of Eli Whiteus, an assistant general manager for the Rockets: Eli published high-quality analysis under a pseudonym on the APBRmetrics forum, later started a blog, and Hinkie tracked it via RSS. He found that Eli's analysis — such as pricing errors in shot location data and defensive evaluation methods — far exceeded the industry standard at the time. Hinkie decided, before ever meeting him, "I want to hire this person." Hinkie emphasizes: "He doesn't need to say he learns fast — his work already proves it."
How to Avoid Transactional Relationships: Hinkie's approach is to "slow down." "This drives transactional people crazy — which is exactly what I want." He suggests testing whether someone is willing to invest time in building a deep relationship by "reading a book together." He cites Mark Andreessen's observation that the best 700 million people can only produce so much content, so it's worth checking your phone; but Hinkie adds that he values messages from his carefully curated inner circle more — these are people who are the result of his years of investment (lowercase "i"), and they come to him with truly important questions.
Writing as a Beacon: Hinkie encourages people to write publicly, especially about content they are proud of. "The returns on writing are enormous." He quotes Stripe's practice of "writing for unborn employees" and argues that writing is the best way to let like-minded people in the future find you.
Boyd Varty argues that everyone has a “wild self” within, which signals through bodily sensations (expansion, joy, calm); while the social self is filled with “shoulds” and “musts.” The art of tracking lies in learning to recognize and follow the trail of the wild self.
Core principles of tracking: Varty learned from master trackers in the South African wilderness as a child. He observed that the best trackers possess a “paradoxical openness” — they are intensely driven to find the target (e.g., a leopard), yet must let go of attachment to the outcome and fully accept the clues present in the moment (tracks, bird calls, wind direction). This is highly analogous to investing and life decisions: “Anyone who tries to operate by a script or preset rules will fail.” He quotes Emerson: “Imitation is suicide.”
A tracker’s day from dawn to dusk as a metaphor for life:
1. Waking up: People are naturally “asleep” in their own lives, operating on autopilot. The first step is deciding to wake up.
2. Waiting for the call: Tuning in through silence; attention brings magic — when you say “I am ready to listen,” something always appears on your path.
3. The first track: Don’t seek to “know the entire path”; just find the “first small move” — “Most people want to wait until they know the full plan before acting, but you need to break the goal down into a series of smaller moves.”
4. Developing trajectory awareness: Train the body to sense when you are “on track” — when you encounter a sense of expansion, or meet people who inspire you, that is your trajectory.
5. Following: The trajectory will take you to places a car cannot reach — those “places without roads.” Varty emphasizes: “Culture presents us with the broad road we should take, but the tracker walks a different path.”
“Cleaning up chaos for others”: Varty believes that true value creation lies in helping others find order from chaos. This connects to the concept of the “strange Venn diagram” — finding the intersection of what you are naturally good at and what you love. “The wild self will not pull you toward areas where you have no talent — that’s what the social self does.”
Response to skeptics: Varty no longer tries to convince cynics. “If you are happy, you won’t be searching; if you are unhappy and still complaining, that is your own choice.” He acknowledges that money is a common obstacle, but the more fundamental barrier is that “people want to know all the answers before they act” — while the essence of tracking is the willingness to enter the unknown.
Most memorable tracking experience: Varty recounts an experience tracking a pride of lions with the top tracker Reneas — from identifying the marks of a lion rolling in cow dung to prepare for a hunt, to Reneas observing the flight direction of flies and sniffing the air for the smell of meat to locate a carcass, to the tense standoff when they unexpectedly discovered cubs in a riverbed. The entire process demonstrates how a tracker uses all senses (sight, smell, hearing) and knowledge of the terrain to weave scattered clues into a complete narrative.
Drawing on 483 investment experiences, Charlie Songhurst argues that startup failure has a dominant cause at each stage, and that the ability to manage scaling is the key differentiator between great and mediocre companies.
Stage-Based Failure Filter:
1. Pre-Seed: Failure to achieve labor productivity — the team cannot coalesce and produce high-quality work.
2. Seed to Series A: Failure to find product-market fit — this is the stage with the highest luck factor, akin to the California Gold Rush: "The smartest prospectors sometimes just can't find gold, while someone falls asleep with a pan in the stream and gold comes out."
3. Post-Series A: Can the manager scale? — This is the "Fermi Paradox-style great filter." Songhurst notes that early founders think they are managing the team, but in reality, the team is "managing up" to them. When the team expands from 10 to 30-90 people, personal relationships break down, and a shift to formal management techniques is necessary. "For great companies, per capita output drops 15% when scaling from 10 to 100 people; for bad companies, it drops over 90% — sometimes a 100-person company produces less than a 10-person one."
4. Post-Series B: Institution building — It becomes necessary to establish "boring but essential" departments like finance, legal, and HR. Founders often excel at early-stage flexibility and energy but dislike repetitive processes and institutional development.
"Study Failure Rather Than Success": Songhurst advocates for reverse thinking — rather than studying great companies, study the common mistakes of failed ones. He observes several common "original sins":
The "Power, Money, Fame" Three-Vice Ranking: Songhurst uses this framework to evaluate founders. Those who prefer power tend to be strong executors but have low capital efficiency and over-expand; those who prefer money are capital-efficient but may be overly cautious and not aggressive enough; he personally tends to avoid founders who prefer fame. This ranking helps him understand where a founder might need assistance.
The Mathematics of Hiring: Songhurst believes hiring is severely underestimated. "Early employees replicate themselves — you can get an upward-iterating excellent culture, or a downward-iterating one." He criticizes founders for hiring in "pulses" aligned with fundraising cycles (hiring heavily after a raise, barely hiring before it), arguing this reduces the probability of finding top talent. He recommends evenly distributing the hiring cadence to assess new hires' synergy after understanding the existing team.
Best Investment Quadrant: Highly Boring + Highly Complex: Songhurst argues that on the two dimensions of "boring vs. interesting" and "simple vs. complex," the best investment zone is "highly boring and highly complex" — because such areas (e.g., audit software, accounting software) lack entrepreneurial supply (no one wants to brag about doing this at a dinner party), leading to less competition and higher returns. Conversely, "interesting and complex" areas (e.g., space technology) attract a flood of talented entrepreneurs, resulting in fierce competition.
This section contains a general discussion of the three guests' methodologies and life philosophies, without involving specific investable companies or position moves. Hinkie mentioned ScoutApp.ai as a recent investment, but no specific data or directional stance was provided.
1. Sam Hinkie: Digital breadcrumbs are the most underrated strategy for identifying top talent. By reading a person's historical body of work (blogs, papers, GitHub, YouTube), you can observe the evolution of their thinking over years, which is far more convincing than any interview. The case of Eli Whiteus proves this: his early blog posts directly made him the "top seed" for the Houston Rockets' hiring.
2. Sam Hinkie: The best way to avoid transactional relationships is to "slow down." Propose a "read a book together" test — if the other party has no time, it means you are not suited for building a deep relationship. This will frustrate transactional people, but that is exactly what you want.
3. Boyd Varty: Humans are naturally prone to "falling asleep" in their own lives; waking up is the first step of tracking. Most people operate in "autopilot mode" and need to actively decide, "I want to wake up in my own life," before they can hear the true calling.
4. Boyd Varty: Do not seek to know the entire path; just find the "first footprint." "Most people want to wait until they have a complete plan before acting, but you need to break down the goal into a series of smaller moves." Each small action opens up the next possibility.
5. Charlie Songhurst: When startups grow from 10 to 100 people, output per person at good companies drops by 15%, while at bad companies it drops by over 90%. The ability to manage scaling is the core filter that separates great companies from mediocre ones, and it can be taught — but usually is not.
6. Charlie Songhurst: Study failure rather than success. "Don't study greatness; study failure, and then figure out how not to become that." Avoid catastrophic mistakes and survive long enough; experience will naturally make you better.
7. Charlie Songhurst: The best investments lie in areas that are "highly boring and highly complex." Because there is a lack of entrepreneurial supply (no one wants to brag about building audit software at dinner parties), competition is low and returns are high. Conversely, "interesting and complex" areas (such as space technology) attract too many talented people, leading to fierce competition.
8. Charlie Songhurst: Hiring should be done at a steady pace, not in "pulses" after fundraising. Early employees will replicate themselves, and their quality determines the iterative direction of the company's culture. Spending 100 hours to hire one person is reasonable — if that person accounts for 10% of the company's output over the next decade.