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Casey Winters Dives Deep Into Prioritization, Second Product Mishaps, Meta & Square

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Many roadmaps follow a flawed pattern:

  • Q1-Q2: Obvious, incremental improvements.
  • Q3-Q4: Vague, ambitious projects (e.g., "magic AI," personalization). This creates a cycle where innovative projects are perpetually delayed.

IF you plan to do something innovative later THEN start building the foundational framework/smaller innovations now to support that bigger vision. This will turn crazy into doable.

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