Tarun Upadhyay.

Writing / Subject

AI and automation

Applying AI to operational work — what it removes, and what it only moves.

  • Pivot gates

    How founders can distinguish a slow strategy from a broken premise before sunk cost makes the decision for them.

    Mar 31, 2026 · Building Routespring

  • Routing optimization isn't a shortest-path problem

    The hard part of flight routing was never finding the cheapest itinerary. It's that 'cheapest' and 'best' are different questions, and one of them is a hard rule while the other is a matter of taste.

    Jan 19, 2026 · Thinking in Public

  • Build versus buy is really a question about who owns the interface

    The standard framing — compare the cost of building to the cost of buying — misses the question that actually decides it: does the vendor's product expose the interface you need, or just the outcome?

    Nov 17, 2025 · Operating Notes

  • Manual minutes per transaction is better than "AI adoption"

    "AI adoption" is one of the least useful metrics in software. Manual minutes per transaction is hard to fake, captures hidden labor, and separates adopting AI from actually improving operations.

    Oct 6, 2025 · Operating Notes

  • Knowing whether a workflow is actually automatable

    Every workflow looks automatable from a distance. Up close it's a sequence of judgments, not clicks. Five questions to ask before you automate anything — and why the process that works 80 percent of the time is the most dangerous kind.

    Sep 29, 2025 · Operating Notes

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