AV Academy VC 101 - Class 6 - Mike’s 100 Venture Capital Greatest Hits
A sharper map for learning venture investing — books, essays, memos, letters, and company stories selected to build judgment, not just reading volume.
You asked for it. This is my venture reading list — the books, essays, letters, memos, and company stories I keep returning to, organized as a practical learning path rather than a “best-of” pile. The Starter Dozen forms the operating system around it: habits, focus, money psychology, decision quality, power, and the long game. The other ninety build the rest.
100
entries
6
core chapters
12
must-reads
30
years of investor practice
This is not a finishing list. The goal is not to check off 100 titles. The goal is to think more clearly about founders, markets, timing, incentives, and risk. Read what interests you. Pair what you read with a live deal. Argue with the author. Then bring the lesson back to the next meeting.
THE CANON: AT A GLANCE
Six Chapters That Build Investor Judgment, Layer by Layer
- Home
Venture Fundamentals
The base layer. Disruption, lean, ops, and the modern startup vocabulary - Home
Founder Craft & VC Mechanics
How founders build day-to-day and how venture actually works - Home
Stories, Strategy, & Markets
Company stories that teach taste, timing, and competitive advantage - Home
Scaling, Culture, & Judgment
The messy middle — leadership, ethics, and judgment under uncertainty - Home
Memos, Models, & Operating Systems
Primary-source documents that reveal how great operators actually thought - Home
Platforms, Ecosystems, & Future Shifts
How technology waves and culture shifts reshape markets
"The goal is not to finish the list. The goal is to think more clearly about founders, markets, timing, incentives, and risk."
The Starter Dozen
If you only read twelve, read these. Eight are widely shared canon and four are personal must-reads. Together they give you a working vocabulary for founder quality, market timing, operating discipline, investor behavior, and decisions under uncertainty.
Unconventional Additions
These won’t appear on most venture lists, but each shaped how I think. They cover the parts of investing that don’t get written about in venture textbooks — personal compounding, money psychology, loyalty and power, the long game.
Chapter 4
Scaling, Culture & Judgment
The messy middle. Leadership, people, ethics, marketplaces, and the kinds of investor judgment that separate “saw it coming” from hindsight.
"Culture and ethics aren't soft stuff. They show up in diligence whether you measure for them or not."
41. Competitive Strategy
Michael Porter | 1980
The classic toolkit for industry structure and positioning.
42. Blue Ocean Shift
Kim & Mauborgne | 2017
A practical process for moving to new demand.
43. The Lean Startup Movement
Eric Ries | 2008–10
The early essays that built the lean startup community.
44. The Netflix Culture Deck
Hastings & McCord | 2009
Freedom, responsibility, and high performance.
45. How to Start a Startup
Sam Altman et al. | 2014
A free startup curriculum from top SV operators.
46. Angel Investing: The Gust Guide
David S. Rose | 2014
Angel investing from the investor’s side.
47. Amazon’s 1997 Shareholder Letter
Jeff Bezos | 1998
Customer obsession and reinvestment as a company creed.
49. The PayPal Mafia
Fortune | 2007
How one company seeded major founders and investors.
51. The Mythical Man-Month
Frederick P. Brooks Jr. | 1975
Why adding people to late projects makes them later.
52. The Giving Tree of Founders
First Round Review | 2015
The emotional cost of founder leadership.
53. 7 Habits of Highly Effective People
Stephen R. Covey | 1989
A durable system for personal effectiveness.
54. The Manager’s Path
Camille Fournier | 2017
Tech leaders growing from mentor to executive.
55. The Cathedral and the Bazaar
Eric S. Raymond | 1999
Open source as a different production model.
56. Lean Analytics
Croll & Yoskovitz | 2013
Metrics by stage — and the One Metric That Matters.
57. Traction
Weinberg & Mares | 2014
A systematic way to find the right growth channel.
58. The Customer-Funded Business
John Mullins | 2014
Revenue, not just VC, can finance a company.
59. Definitive Guide to Raising From Angels
Bill Payne | 2014
Angel fundraising, valuation, and expectations.
60. Effectuation
Saras Sarasvathy | 2001
Entrepreneurs co-create the future from the means at hand.
61. Capitalism, Socialism & Democracy
Joseph A. Schumpeter | 1942
The source text for creative destruction.
62. Pirate Metrics
Dave McClure | 2007
Acquisition, activation, retention, referral, revenue.
63. State of Startups Reports
First Round Capital | 2015–present
Tech leaders growing from mentor to executive.
64. The Single Biggest Reason Startups Succeed
Bill Gross | 2015
A short, data-driven argument that timing matters most.
65. High Growth Handbook
Elad Gil | 2018
A scaling field guide for life after product-market fit.
Chapter 5
Memos, Models & Operating Systems
Primary-source memos, founder letters, frameworks, and internal documents that reveal how the best operators actually thought when the stakes were highest.
"Great investors love primary source documents because they reveal how builders actually thought."
66. Google “Don’t Be Evil” IPO Letter
Page & Brin | 2004
A mission-forward declaration for long-term tech builders.
67. The Making of Silicon Valley
Tom Wolfe | 1983
Robert Noyce, Fairchild, and the Valley’s origin story.
68. The Other Side of Innovation
Govindarajan & Trimble | 2010
How large organizations actually execute innovation.
69. Open Innovation
Henry Chesbrough | 2003
Why companies should use external ideas and partners.
70. The Startup Way
Eric Ries | 2017
Mature organizations using startup-style innovation systems.
71. Exponential Organizations
Salim Ismail | 2014
Patterns for companies that scale with community and algorithms.
72. Makers: The New Industrial Revolution
Chris Anderson | 2012
Hardware, 3D printing, and the maker movement.
73. The Atlassian Team Playbook
Atlassian | 2017
Team exercises for alignment, roles, and collaboration.
74. No Rules Rules
Hastings & Meyer | 2020
Netflix’s high-talent, low-control culture, in depth.
75. The E-Myth Revisited
Michael E. Gerber | 1995
Build systems so the business scales beyond the founder.
76. Principles
Ray Dalio | 2017
Radical transparency and explicit operating principles.
77. YC Demo Day Videos & Decks
Y Combinator | 2005–present
The standard format for crisp early-stage storytelling.
78. The Lean Canvas
Ash Maurya | 2010
A one-page model: problem, solution, metrics, advantage.
79. Famous Founder Letters
Chesky, Hsieh, et al. | Various
Culture, values, and mission written by founders themselves.
80. MuleSoft Startup Venture Memo
Ross Mason | 2006
A founder vision document for a large enterprise opportunity
81. Snowflake’s Secret IPO Memo
Frank Slootman | 2020
Blunt leadership during a high-profile IPO.
82. Software Engineering at Google
Google | 2000s–present
Practices for scaling code, teams, testing, and reliability.
83. We Don’t Sell Saddles Here
Stewart Butterfield | 2013
Sell the better way of working, not the tool.
84. IDEO’s Shopping Cart Project
ABC Nightline | 1999
Design thinking and rapid prototyping made visible.
85. The Cluetrain Manifesto
Levine, Locke, Searls, Weinberger |1999
Markets are conversations — companies need a human voice.
Chapter 6
Scaling, Culture & Judgment
The messy middle. Leadership, people, ethics, marketplaces, and the kinds of investor judgment that separate “saw it coming” from hindsight.
"Culture and ethics aren't soft stuff. They show up in diligence whether you measure for them or not."
86. Lean In
Sheryl Sandberg | 2013
A major catalyst for conversations about women in tech leadership.
87. Brotopia
Emily Chang | 2018
A hard look at exclusion and accountability in Silicon Valley.
88. The Agile Manifesto
Beck, Sutherland, et al. | 2001
The values that reshaped software around iteration and users.
89. Toyota Production System / The Goal
Ohno · Goldratt | 1978/1984
Lean operations and bottlenecks behind startup methods.
90. Startup Communities
Brad Feld | 2012
The Boulder Thesis and the long game of building ecosystems.
91. The SAFE
Y Combinator | 2013
A simple instrument that changed seed fundraising norms.
92. VentureHacks Blog
Nivi & Naval | 2007–2010
Plain-English funding mechanics before AngelList.
93. The Acqui-hire & Talent Auctions
Tech press | c. 2010
How talent-driven exits changed founder expectations.
94. Marc Andreessen’s Tweetstorms
Marc Andreessen | 2014
A new direct format for investors to publish theses.
95. Hustle: The Cure for Those Who Complain
Gary Vaynerchuk et al. | 2016–19
Hustle culture and the backlash it triggered
96. The Financial Crisis for Startups Post
Sequoia / TechCrunch | 2008
Public circulation of downturn advice that shaped behavior
97. Product Hunt
Ryan Hoover | 2013
A daily launch ritual and discovery engine for new products.
98. Mobile Is Eating the World
Benedict Evans | 2014
A chart-rich thesis deck that shaped mobile-era strategy.
99. SaaStr Blog & Annual Conference
Jason Lemkin |2012–present
Tactical SaaS scaling advice made public and repeatable.
100. AngelList
Naval Ravikant & Babak Nivi | 2010
Online startup fundraising, syndicates, and education.