Kyle Harrison
person

Bill Gurley

Bill Gurley

General partner at Benchmark and one of the venture investors Kyle cites most across his essay research. He embodies Benchmark’s “anti-Softbank,” cottage-scale model — small fund, each partner making roughly one investment a year — which makes him the human face of the “Puritans of Venture Capital” archetype in Kyle’s notes. The Power Law — Venture Capital & the Making of the New Future supplies the lore: Gurley’s “grand-slam business” framing, his unicorn-governance critiques (Uber, WeWork, liquidation preferences), and his fifty-fifty conviction that coaching entrepreneurs matters as much as deal selection. With Uber he is remembered for “feeling like he was the only adult in the room” — his $12M check returning $5.8B. Before venturing, per The Everything Store, Gurley was a lead sell-side analyst who “presciently identified” Amazon early as one of the Internet’s “wave riders.”

Gurley’s writing is a primary source for Kyle. His 1999 essay “The Rising Importance of the Great Art of Storytelling” anchors The Storytelling of Investing - Research as the cautionary counterweight — the dangerous, hype kind of storytelling — and his work on Community-Adjusted EBITDA traces the lineage of misleading metrics back to Craig McCaw’s “homes passed” and “POPs” (“don’t look at this, look at that”). His online-marketplace framework appears in Kyle’s Investment Frameworks learning page. And his market-cycle warnings run through The Death of a Venture Fund - Research: his All-In line that “a vast majority of the reason venture outperforms… has to do with these tiny windows where you have a super frothy market” — strip those years out and “it’s actually not that interesting of an asset class” — plus his tweet that calling a deal “cheap relatively” is now meaningless. In The Renaissance of Rise and Grind - Research he is invoked in the Twitter-era hard-work debate, arguing that building startups requires hard work and that different roles demand different levels of commitment.

Context: Bill Gurley is a longtime general partner at Benchmark and author of the influential “Above the Crowd” blog. He led Benchmark’s investment in Uber and is widely known for his writing on marketplaces, unit economics, late-stage market excess, and venture-fund discipline.

Where this appears

  • The Power Law — Venture Capital & the Making of the New Future — Benchmark’s “anti-Softbank” model; “grand-slam business” framing and unicorn-governance critiques.
  • The Everything Store — as the analyst who early identified Amazon as an Internet “wave rider.”
  • Benchmark — the firm he anchors as the Puritan/cottage-scale archetype.
  • The Storytelling of Investing - Research — his 1999 “Storytelling” essay as the cautionary hype counterweight.
  • The Death of a Venture Fund - Research — his market-cycle warnings (“tiny frothy windows,” Uber’s $12M → $5.8B).
  • Community-Adjusted EBITDA — his lineage of misleading metrics back to McCaw’s “homes passed.”
  • The Renaissance of Rise and Grind - Research · Surviving The Death of Venture Capital - Research · The Puritans of Venture Capital - Research — recurring source on hard work, predatory pricing, and the cottage-fund model.
  • Investment Frameworks — his online-marketplace effectiveness framework.

Above the Crowd — Newsletter Bibliography

A year-by-year index of Gurley’s Above the Crowd archive, from the 1994 maiden issue forward — the PC-era Intel/Microsoft essays, the S-curve and switching-cost pieces that became standard vocabulary, and the “This Thing is Huge: The Internet Will Change the World” turn. Titles are listed as a bibliography rather than as links; the essays live at abovethecrowd.com.

  • 1994
    • The Maiden Issue: BM/Intel, PC Uncertainty Principle
    • Strategic Envy: We Can’t All Be Intel and Microsoft
    • Primum No Nocere: The Government Goes After Microsoft
    • Does History Repeat? PCs by Phone, the All-in-One Machine, & Video Conferencing
  • 1995
    • Disclosure: There Are Costs Associated with Limited Information
    • Remembering Moore’s Law: Big Brother ‘Saves’ the World from Microsoft
    • Leveraging Your Strengths: Gateway 2000 and Packard Bell
    • Nothing Lasts Forever: The Future of Intel and Microsoft
    • New Kid on the Block: HP Decides to Be a Player in PCs
    • Behold the Sigmoid: The Importance of the S Curve in High Tech Product Adoption
    • Perception vs. Reality: The Increasing Complexity of Measuring PC Demand
    • Lowering the Barriers to Entry: Intel Makes It Easy to Be a PC Company
    • Limiting Excess Profitability: A New Intel Motherboard Theory
    • The Good, the Bad, and the Ugly: Catching Up with Apple Computer
    • PC Feature Wars: Differentiation in a Commodity Market
    • Switching Costs as a Strategic Tool: How Hard Is It for Your Customers to Leave?
    • Breaking Up Is Hard to Do: Intel and Compaq Kiss and Make Up, for Now
    • The Next Wave in Consumer Electronics: Can Sony Save Apple?
    • This Thing is Huge: The Internet Will Change the World
    • Here We Go Again: Two New Intel Motherboard Theories
    • Understanding Internet Valuations: The Financial Markets Adapt to Increasing Returns
    • Profitless Prosperity in Home PCs: What About Gateway 2000?
    • Castles Made of Sand: MSN Melts into the Internet
    • The Next Great Killer App: Will the Internet Drive PC
    • The Strategic Business Unit: Questioning the Wisdom
    • I’m Not Dead Yet: Intel’s NSP Iniative is Alive and Well
    • Reality Bits: How Well Do Reported Numbers Represent True Economic Reality
    • The Internet Terminal: Our $0.02 on the $500.00 Box
    • Rich E-Mail: The Client Grows Up
  • 1996
  • The Trojan Horse: Apple Manages to its Software Books?
  • Predictions: Let Demand (Not Supply) Be Your Guide
  • Apple’s New CEO: What to Expect from Gil Amelio
  • Stunningly Obvious: The Secrets of Software Economics
  • Dialing for Dollars: A Look at Today’s Modem Market
  • An Oliver Stone Tribute: Three High Tech Conspiracy Theories
  • Internet Telephony: Don’t Call Me, I’ll Call You
  • Beyond the Romance: In Search of Wave Riders
  • Under the Hood: The Evolution of OLE
  • The E-mail Revolution: How the Internet will Change Electronic Messaging
  • The Second Wave: Internet Applications
  • Forget Technology: It’s All Marketing These Days
  • The Data Channel: Cable’s Ace in the Hole
  • Backhoes Don’t Obey Moore’s Law: A Story of Convergence
  • Usage Based Pricing: Not If, But When
  • Making Sense of MSN
  • It’s Time to Choose Sides
  • IWorld: Our View from the Road
  • Internet Economics: The FCC Chimes In
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  • 1997
  • Can it Work?: Considering the Free ISP
  • Online Transactions: Who Gets Paid?
  • Internet Evolution: Commercialization Continues
  • Revenge of the Nerds: The Stock Option Square Dance
  • Good News, Bad News: On-Line Commerce Takes Off
  • Considering the Alternative: Another Look at the NC
  • Say Hello to Capitalism: And Goodbye to the Net We Once Knew
  • Trophy Hunting: Finding Big Game In the High-Tech Investment World
  • New Media Update: A Tech Guy’s Perspective
  • Reed Hundt’s Last Stand: Did you Say Reform or Deform?
  • Sales Tax and The Internet: What’s Next with Nexus
  • DCOM and CORBA: Making Sense of the Object Wars
  • Caveat Venditor: Seller Beware!
  • Marketing Myopia: Is a Software Company a Software Company?
  • Data Broadcast: The New Frontier
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  • 1998
  • Don’t Look Now, But the Browser Already IS the Operating System
  • The Vertical Vortex: It’s Not About Technology, It’s About Context
  • A High-Tech Version of the Cold War
  • How to Succeed In Advertising
  • Standards: Open For Business
  • Taking Tolls on the Information Superhighway
  • The New World of Virtual Distribution
  • Internet Investors: Beware of the Proxy Valuation
  • A Dell For Every Industry
  • The Continued Evolution of Advertising or How to Succeed Part 2
  • If it’s a Good Idea… Think Twice…
  • How Low Can You Go?
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  • 1999
  • The New World of Big Fat Web Sites
  • The New Face of Internet Competition
  • Will you “Rent” Software in the Future?
  • The Battle of the Banks
  • Patent Here, Patent There, Patent, Patent Everywhere
  • The Rising Impact of Open Source
  • The Evolving World of E-tailing
  • The Next Big Thing
  • The Rising Importance of the Great Art of Storytelling
  • Browse, Shop… Get Paid
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  • 2000
  • Could the Portal Industry Be Commoditized?
  • The Most Powerful Internet Metric of All
  • BigCompany.com - Corporate America Embraces the Startup
  • Can Napster be Stopped? NO!
  • A Return to Demand-driven Capitalism
  • Like it or Not, Every Startup is Now Global
  • The End of CPM
  • Making Sense of the Wireless Internet
  • Music, Morality, and Moore’s Law
  • A Great Time for Building Great Companies
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  • 2001
  • What Now? Moving Past the Correction
  • The Next Big Thing: 802.11b?
  • The Good News is the Bad News When it Comes to High Tech Spending
  • The Smartest Price War Ever
  • Bye, Bye, Bluetooth
  • Tapping the Internet
  • When it Comes to Pricing Software, the Greener Grass is Hard to Find
  • Silicon Valley’s Need for Oblivion
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  • 2002
  • It’s Time to Put a Stop to Spam
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  • 2003
  • 802.11 & Cellular: Competitor or Complement?
  • Software in a Box: The Comeback of the Hardware Based Business Model
  • Pay Attention to BPM
  • Dot-com Double Take
  • In Search of the Perfect Business Model: Increasing Marginal Utility
  • The Comeback of the Mobile Internet
  • Much Ado About Options
  • Beware the Digital Hand
  • Cleaning Up After the Ninth Circuit in an Attempt to Save the Internet
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  • 2004
  • The Rise of Open Standard Radio: Why 802.11 is Under Hyped
  • All Things IP: The Future of Communications in America
  • Entrepreneurialism and Protectionism Don’t Mix
  • The Revolutionary Business of Multiplayer Gaming
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  • 2005
  • Slow the Proliferation of Broadband
  • Texas Refuses to Block Broadband
  • Texas Two Step-Backwards
  • Texas Sets Key Precedent
  • Pro-Broadband Issue Goes National
  • DVD Glut
  • Do VCs Help in Building Tech Platform
  • Wifi Nation
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  • 2006
  • Why SOX… Demise of US Markets
  • As Wifi Grows, So Do PR Attacks
  • MMOs Continue to Rock
  • Techdirt: Fake Broadband Price War
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  • 2008
  • Back to Blogging
  • Bleak VC Quarter? Why?
  • BAILOUT what?
  • Benchmark Capital: Open for Business
  • Do VCs Help in Building Tech Platform 2
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  • 2009
  • Google Stock Option Re-pricing
  • SlideRocket
  • Green Government Venture Fund
  • Green Government Venture Fund 2
  • Perfect Online Video Advertising Model
  • Looking For Work: Insurance Agent?
  • How To Monetize Social Network
  • Do Startups Need More Regulation?
  • Swine Flu: Overreaction
  • Second Life: Second Most Played PC Title
  • Online Video Market Snapshot
  • Will Apple Make an Actual TV?
  • Comments on the IPO Market
  • Education Company in Korea: Megastudy
  • Amazon’s AWS Strategy
  • Bill Gurley on “Free” Business Model
  • I Do Not Believe Zappos was Forced to Sell
  • Counter-Point to Calacanis
  • More IPO News, Ancestry.com Files S1
  • Rosetta Stone vs LiveMocha
  • What is Really Happening in VC?
  • Want to Know the Future of Internet TV?
  • Google Redefines Disruption
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  • 2010
  • Android or iPhone?
  • Virtual Goods, Accounting, “Rental” Model
  • For Tv: Affiliate Fees Make World Go Round
  • Googe Acquires ITA
  • On Google, Growth, Pricing Power, Valuation
  • Silicon Valley’s IPO Anxiety
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  • 2011
  • Freight Train That is Android
  • Keys to the 10X Revenue Club
  • If You Are Going to File, Make Sure to Price
  • Understanding Why Netflix Changed Pricing
  • Steve Job’s Remarkable Value Creation
  • You Don’t Have to Tweet to Twitter
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  • 2012
  • Thinking About Diets and Complex Matters
  • Why FB Clearly Belongs in 10X Revenue Club
  • Why Dropbox is a Major Disruption
  • Why Youth Has an Advantage in Innovation
  • My Life with Bing
  • Intuit to Acquire Demandforce
  • “Local” Will be the Biggest of the Three
  • Dangerous Seduction of LTV Formula
  • 10 Factors to Consider for Digital Marketplaces
  • DogVacay from Los Angeles
  • Favorite Longreads of 2012
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  • 2013
  • Optimal Platform Pricing Strategy
  • Grubhub and Seamless
  • Transitioning to a Mobile Centric World
  • Conversion: Most Important Metric (Revisted)
  • Stitch Fix: Reinventing Retail
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  • 2014
  • On Bubbles…
  • Deeper Look at Uber’s Dynamic Pricing Model
  • HackerOne: Solving Web Vulnerabilities
  • Disrupting Finance From Above: Wealthfront
  • Welcoming the Vessel team to Benchmark
  • Alternative Look at Uber’s Market Size
  • Meet Benchmark’s Eric Vishria
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  • 2015
  • Uber’s New BHAG: UberPool
  • Investors Beware: Late-stage Rounds NOT IPOs
  • … Be Like Dave
  • In Defense of the Deck
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  • 2016
  • On the Road to Recap
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  • 2017
  • Benchmark’s New GP Sarah Tavel
  • Thinking of Home: Dickinson, Texas
  • The Ezra Klein Show: Transforming Healthcare
  • “Customer First” Healthcare
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  • 2018
  • The Thing I Love Most About Uber
  • Benchmark’s New GP Chetan Puttagunta
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  • 2019
  • How Internet Marketplaces Unlock Wealth
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  • List of Books Mentioned
  • About Bill Gurley

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