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More Money More Problems

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Teams hit four recurring technical inflection points as growth brings more customers and more problems: legacy systems require rewrites and designers should build for deprecation so migrations stay incremental; stop inventing every commodity and play to core strengths or buy expertise; accept failures will happen and invest in detection plus automated mitigation like “red buttons”; and measure developer experience — aim for 2x with half the people by automating toil and track simple metrics (for 100 people keep ≤3 metrics, split work ~50–60% features, 15–25% ops, 10–20% investing).

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  1. 0:00Introduction
  2. 2:09More money more problems
  3. 4:41Team/company growth phases
  4. 9:13Technical challenges
  5. 9:55Systems needing rewrites
  6. 14:29Core strengths and leverage
  7. 19:26Preparing for bad things
  8. 24:01Scaling with automation
  9. 25:29Developer experience
  10. 28:43Key takeaways
  11. 37:37Q&A
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