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• What You'll Wish You'd Known - mandatory reading for the under 18 crowd. ~10 years after reading this, if I was to make a list of the 5 webpages that have done the most to shape who I am as a person, this would likely be on the list.
• How To Disagree - this is the kinda thing SSC readers love right?
• Six Principles for Making New Things - Graham's most underrated essay IMO, and perhaps comes closer than any other essay to communicating the "Paul Graham way of viewing the world" (which, I'd argue, is a super useful set of goggles to have available)
• The Acceleration of Addictiveness
• General & Surprising
• The Risk of Discovery
• What You Can't Say
• How to Make Wealth
• Good & Bad Procrastination
• The Power of the Marginal
• Is It Worth Being Wise?
• How to Do Philosophy
• How to Do What You Love
• Why Nerds are Unpopular
• The Submarine
• Writing, Briefly if you're a writer
• The Word "Hacker"
• Why Nerds are Unpopular: http://www.paulgraham.com/nerds.html
• Keep Your Identity Small: http://www.paulgraham.com/identity.html
• How to do Philosophy: http://www.paulgraham.com/philosophy.html
• How to Start a Startup http://paulgraham.com/start.html
• Hiring is Obsolete (maybe his best) ttp://paulgraham.com/hiring.html
• The Hardest Lesson for Startups to Learn http://paulgraham.com/startuplessons.html
• The 18 Mistakes that Kill Startups http://paulgraham.com/startupmistakes.html
• Why To Not Not Start a Startup http://paulgraham.com/notnot.html
• Holding a Program in One's Head http://paulgraham.com/head.html
• Cities & Ambition (cited by Jeff) http://paulgraham.com/cities.html
• Relentlessly Resourcesful http://paulgraham.com/relres.html
• What Startups are Really Like (previously cited by Charlie)
• http://paulgraham.com/avg.html
• http://www.paulgraham.com/top.html
• Do Things that Don't Scale
• The 18 Mistakes That Kill Startups

On startups and their operation:

• Do Things that Don't Scale
• Startup = Growth
• Default Alive or Default Dead?
• Ramen Profitable
• The 18 Mistakes That Kill Startups

For founders:

• Before the Startup
• What We Look for in Founders
• A Word to the Resourceful

On startup funding:

• How to Fund a Startup
• How to Raise Money
• How to Convince Investors
• A Unified Theory of VC Suckage
• Subject: Airbnb

How to get startup ideas:

• How to Get Startup Ideas
• The Bus Ticket Theory of Genius
• Schlep Blindness
• Organic Startup Ideas
• Ideas for Startups