ARTIFICIAL INTELLIGENCE

“There are people in this world who view everything as a zero sum game and they will elbow you out the first chance they can get. And so those shouldn’t be your peers.” – Bill Gurley – GP at Benchmark

This incisive observation comes from Bill Gurley, a General Partner at Benchmark Capital, shared during his appearance on Tim Ferriss’s podcast in late 2025. In the discussion titled ‘Bill Gurley – Investing in the AI Era, 10 Days in China, and Important Life Lessons,’ Gurley outlines two key tests for selecting peers and collaborators: trust and a shared interest in learning. He warns against those with a zero-sum mentality-individuals who see success as limited, leading them to undermine others for personal gain. Instead, he advocates pushing such people aside to foster environments of mutual support and growth.^3,6

The quote resonates deeply in careers, entrepreneurship, and high-stakes fields like venture capital, where collaboration can amplify success. Gurley, drawing from decades in tech investing, emphasises that true progress thrives in positive-sum dynamics, where celebrating peers’ wins benefits all.^1,3

Bill Gurley’s Backstory

Bill Gurley is a towering figure in Silicon Valley, renowned for his prescient investments and analytical rigour. A General Partner at Benchmark Capital since 1999, he has backed transformative companies including Uber, Airbnb, Zillow, and Grubhub, generating billions in returns. His early career included roles at Morgan Stanley and as an executive at Compaq Computers, followed by an MBA from the University of Texas and a Harvard undergraduate degree.^1,2

Gurley’s philosophy rejects rigid rules in favour of asymmetric upside-focusing on ‘what could go right’ rather than minimising losses. He famously critiques macroeconomics as a ‘silly waste of time’ for investors and champions products that are ‘bought, not sold,’ with high-quality, recurring revenue.^1,2 An avid sports fan and athlete, he weaves analogies like ‘muscle memory’ into his insights, reminding entrepreneurs of past downturns like 1999 to build resilience.² Beyond investing, Gurley blogs prolifically on ‘Above the Crowd,’ dissecting marketplaces, network effects, and economic myths, such as the fallacy of zero-sum thinking in microeconomics.⁵

Context of Zero-Sum Thinking in Careers and Investing

Gurley’s advice counters the pervasive zero-sum worldview, where one person’s gain is another’s loss. He argues life and business are not zero-sum: ‘Don’t worry about proprietary advantage. It is not a zero-sum game.’¹ Celebrate peers’ accomplishments to build collaborative networks that propel collective success.¹ This mindset aligns with his investment strategy, prioritising demand aggregation and true network effects over cut-throat competition.^1,2

In the Tim Ferriss interview, Gurley ties this to team-building, invoking sports leaders like Sam Hinkie for disciplined, curiosity-driven cultures. He contrasts this with zero-sum actors who erode trust, essential for long-term performance across domains.³

Leading Theorists on Zero-Sum vs Positive-Sum Games

John Nash (1928-2015), the Nobel-winning mathematician behind Nash Equilibrium, revolutionised game theory. His work shows scenarios need not be zero-sum; equilibria emerge where players cooperate for mutual benefit, influencing economics, evolution, and AI strategy.

Robert Wright, in Nonzero: The Logic of Human Destiny (2000), posits history evolves towards positive-sum complexity. Trade, technology, and information sharing create interdependence, countering zero-sum tribalism-echoing Gurley’s peer advice.

Yuval Noah Harari, author of Sapiens, explores how shared myths enable large-scale cooperation, turning potential zero-sum conflicts into positive-sum societies through trust and collective fictions.

Elinor Ostrom (1933-2012), Nobel economist, demonstrated via empirical studies that communities self-govern common resources without zero-sum tragedy, through trust-based rules-validating Gurley’s emphasis on reliable peers.

These theorists underpin Gurley’s practical wisdom: reject zero-sum peers to unlock positive-sum opportunities in careers and ventures.^1,3,5

Related Insights from Bill Gurley

• “It’s called asymmetric returns. If you invest in something that doesn’t work, you lose one times your money. If you miss Google, you lose 10,000 times your money.”^1,2
• “Everybody has the will to win. People don’t have the will to practice.” (Favourite from Bobby Knight)¹
• “Truly great products are bought, not sold.”¹
• “Life is a use or lose it proposition.” (From partner Kevin Harvey)¹