A Field Guide to Startup Anti-Patterns: 80+ Ways Companies Sabotage Themselves

Simeon Simeonov (who first floated the idea in 2013) and Itamar Novick of Recursive Ventures are launching a series cataloging startup anti-patterns — habits, structures, or decisions that look like sensible responses to a problem but end up doing more harm than good. The premise is that success is idiosyncratic and hard to reverse-engineer, while failure tends to rhyme. Studying the repeatable ways startups blow themselves up is therefore more instructive than chasing the non-repeatable strategies behind any single win.

The post is really an index rather than an argument: it lays out a work-in-progress list of 80-plus named failure modes drawn from the authors’ experience across 100+ companies as founders and investors. The entries span strategy (elephant hunting, chasing blue oceans, death by pivot, boiling the ocean), execution and org dysfunction (design by committee, founderitis, groupthink, analysis paralysis, deathmarch), engineering traps (overengineering, premature optimization, premature scaling, bleeding on the edge, outsourcing your architecture), and fundraising or investor-facing pitfalls (lying to investors, designing for investors, spreadsheet bingo, weak board). Each is meant to be fleshed out later with concrete examples from portfolio founders.

The framing carries a useful caveat: no single anti-pattern is fatal, and the list isn’t ‘drawn to scale’ — some occur far more often or are far deadlier than others. The value is compounding risk awareness. For technical founders and operators, it functions as a checklist of self-inflicted wounds — particularly the engineering-side entries like overengineering and outsourcing architecture, which map directly onto how technical teams quietly erode a company’s ability to execute.