Pre-Mortem

The discipline of imagining failure before it happens — “dream the nightmare” — as a counterpart to the after-the-fact Post-Mortem. In The Founders it is embodied by David Sacks’s thought experiment at PayPal: “If I was running eBay Payments, what would I do to kill PayPal?” — Kyle tags this directly as a pre-mortem, the move of running the rival’s playbook against yourself to surface platform risk before it materializes.

Kyle’s own essay research formalizes the idea. What’s In a Post-Mortem - Research frames the pre-mortem as the “dream the nightmare” sibling of the post-mortem — laying out thesis plus worst cases up front so you can watch the failure points throughout, attributed to a “pre-parade”/“pre-mortem” memo structure popularized by Larry Summers and used at Index Ventures, and connected to Josh Wolfe’s “imagining failure.” The Death of a Venture Fund - Research operationalizes it as Kyle’s ~30 verbatim VC interviews built on a single pre-mortem prompt: “why do you think your firm will go out of business?” Across all three, the unifying premise is that the willingness to confront failure — a Spirit of Humility — is what makes the technique work.

Context: The “pre-mortem” was popularized by psychologist Gary Klein: before a project begins, the team imagines it has already failed and works backward to explain why, surfacing risks that optimism and groupthink would otherwise suppress.

Where this appears

• The Founders — David Sacks’s “if I were running eBay Payments, what would I do to kill PayPal?” as a pre-mortem on platform risk
• What’s In a Post-Mortem - Research — the “dream the nightmare” sibling of the post-mortem; the Summers/Index “pre-parade & pre-mortem” memo structure
• The Death of a Venture Fund - Research — ~30 VC interviews built on the pre-mortem prompt “why will your firm go out of business?”