Apr 12, 2024, 11:00 AM ETInterview

Kyle Harrison, GP at Contrary on Techno-Optimism, Talent Vortexes, & Writing “Investing 101”

Former film major turned venture capitalist with a "stumble" career path starting with a janky video production marketplace sold after four years.
Invested in companies including Ramp, Retool, Anduril, and Armada across diverse fund styles.
Career history includes a 4-year tenure at TCV (private equity style), 2 years at Coatue (hedge fund/arbitrage), and 2 years as a partner at Index (classic venture).
Joined Contrary to apply a "holistic framework" for supporting talent from undergrad through company exit, rather than just funding deals.

Founded by Eric Terezinski based on the thesis that identifying the "smartest people" early and supporting them relentlessly creates an unfair advantage.
Firm model shifted from early-stage investing to also building "talent vortexes," where prior employees from Contrary-backed companies (e.g., 5 of Ramp's first 50 employees) serve as a talent pipeline for new ventures.
Investment scope expanded to pre-seed through Series B+, focusing on being a "first check" partner or plugging into the Contrary talent community for later-stage deals.
Firm acts as a "product" for career stages, offering services like job introductions, co-founder matching, and investor evaluation for high-performing individuals.

Research arm was productized in response to repeated requests from top 1% talent to evaluate private job offers and understand market dynamics.
Research reports are open-sourced to allow external feedback and to establish Contrary as an objective authority rather than a content marketing vehicle.
Content strategy explicitly avoids exclusive coverage of portfolio companies to maintain a "pragmatically optimistic" and balanced perspective.
Current deep-dive projects include a historical analysis of defense/military tech (covering companies like Anduril) and a framework on crystallizing societal and technological trends.

Maintains a "generalist" approach necessitated by the core thesis of backing talent regardless of industry vertical (FinTech, AI, or physical manufacturing).
Leverages community insights to identify compelling opportunities in sectors like defense, aerospace, and manufacturing driven by deglobalization and geopolitical conflict.
Uses a "prepared mind" to rapidly evaluate new categories, supported by extensive research into markets where active investment is currently low.

Newsletter "Investing 101" has over 17,000 subscribers and operates on a "write once a week, never miss" discipline rather than a metric-driven business model.
Key philosophical pieces include: "The Black Stone of Innovation" (big capital agglomerators), "The Institutionalized Belief in the Greater Fool" (bag holding), and "The Puritans of Venture Capital" (contrasting small vs. large firms).
Personal favorite underperforming pieces include "Historical Futurism" (fiction as a guide for reality) and "The Renaissance of Rise and Grind" (debating the virtue of hard work vs. exploitation).

Harrison has evolved from believing "reality wins" to the conviction that "stories shape reality," arguing that what people believe actively constructs their experience of the world.
Identifies increasing polarization in tech and media, where groups view reality through siloed narratives (e.g., hard work vs. work-life balance) rather than nuance.
Critiques the WEF's identification of misinformation/disinformation as the top global risk, attributing it to short-form content algorithms and political cycles.
Suggests that "truth" often hides within jokes and pranks (referencing April Fool's Day), as compelling fiction requires a kernel of reality to function.

Moved from the Bay Area to Utah to be closer to family, noting the "existential quandary" of affordability for families in Silicon Valley forces migration eastward.
Observes that moving away from the SF hub provides clarity on "in-group beliefs," noting that most people use group identity as a proxy for their own independent thought.
Maintains a nuanced view that while good companies can be built outside the Bay, statistically, the majority of high-impact companies remain concentrated there due to specific playbooks and heuristics.

Forecasts an "age of acquisition" where "large + large" and "small + small" deals increase as a mechanism for recycling capital and human talent after failed standalone experiments.
Views company failure as a healthy "natural selection" process for iteration, which was suppressed during the 2021 capital abundance but is returning as a necessary market corrective.
Advocates for understanding "hype inflation and deflation" cycles, noting that while hype attracts hucksters, periodic deflation flushes out bad actors and stabilizes the ecosystem.
Cites Anduril's founder Palmer Luckey as an example of founders who persist through hype cycles regardless of whether their specific industry (defense/AI) is currently fashionable.