Here’s some that I go back to often:
Startup Metrics for Pirates by Dave McClure of 500 Startups is a classic because it quantifies successful product design.
The One Cost Engineers and Product Managers Don’t Consider, derived from a talk by Kris Gale, VP Engineering at Yammer. Probably the most level-headed argument for saying “no” more often, where most people simply assume it must be true because Steve Jobs said so.
How Design Thinking Transformed Airbnb from a Failing Startup to a Billion Dollar Business, derived from a talk by Joe Gebbia. Most people are familiar with the “do things that don’t scale” myth of AirBnB, but the “Let people be pirates” part is arguably more valuable.
We don’t sell saddles here by Stewart Butterfield, founder of Slack.
The Law of Shitty Clickthroughs by Andrew Chen articulates why first-mover advantage applies to marketing, not product. Read alongside Marc Andreessen’s statements on product-market fit and this breakdown of how product-market fit is distributed across competitors.
And read all of Paul Graham’s essays. Some aren’t great, but most are worth it.