How I'd Run It

A series where I pick a real operational problem at a company I find interesting, build a working prototype, and lay out how I'd run the first 90 days.

  1. Stripeacquisition risk

    Keeping OpenRouter fast after Stripe buys it

    A 90-day post-acquisition plan for keeping OpenRouter's speed and neutrality alive inside Stripe, with a working velocity-divergence monitor prototype.

  2. Datadogdocumentation risk

    Keeping 1,200 people fluent after Datadog's DASH

    A 90-day program design for keeping 1,200 customer-facing people accurate after a 100+ feature launch, with a working freshness tracker prototype.