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Insights

Essays, thoughts and other stuff (aka my “junk” drawer).

Essays

About 12 minutes

Can Someone Tell Me Where I Can Find a Real Magic Wand?

A specification described the cable rather than the drive, and the mistake led somewhere: memory and computation are roles a physical state plays, not kinds of object. What it costs when the name for a thing arrives before you have looked at the thing.

About 4 minutes

Delete with Extreme Prejudice

Deleting one feature meant understanding half the codebase. So I wrote down the rule I actually needed: architecture follows what is consumed, not what might be reused.

Operating documents

Redacted copies of documents the work actually runs on

  • 01

    Redacted · 25 min read, or under a second

    Working Agreement

    The contract every AI agent reads at the start of a session — what is immutable, what is open to judgment, and what each rule cost to learn.

  • 02

    Redacted · 6 min read, hours to learn

    What you wished were available

    What I wished we had already recorded when something broke at 3am. Every layer logged; the answer was still one log line away, and cost hours.

LinkedIn series

12 posts + an epilogue

  1. 01

    ACH · Part I

    Adoption of money systems is driven less by technical superiority and more by operational survivability

    If a money system can’t tolerate human error, it won’t be adopted — no matter how elegant it is.

  2. 02

    ACH · Part II

    ACH Isn’t Clunky. It’s Forgiving.

    ACH gets dragged a lot.

  3. 03

    ACH · Part III

    Speed Isn’t the Enemy. Irreversibility Is.

    There’s a common belief that legacy payment systems survive because institutions are slow to change.

  4. 04

    Execution

    Working hard doesn’t have to mean hard work.

    Most organizations say they reward outcomes. What they actually reward is visible effort.

  5. 05

    Questions

    When “Why” Shows Up Late

    When “why” shows up late, it shows up expensive.

  6. 06

    Learning by building

    The Porch Light Problem

    It all started with a DoorDash delivery one night…

  7. 07

    Mergers & acquisitions

    When the Math Is Right but the Deal Isn’t

    I’ve been in rooms where the model cleared but the deal didn’t.

  8. 08

    Preparedness

    Confidence, Indifference, or Preparedness?

    In high-stress rooms, calm gets interpreted in three different ways.

  9. 09

    Discovery

    Creativity didn’t disappear. It just stopped clearing the budget process.

    Markets and large organizations are shaped by business school logic for a reason.

  10. 10

    Incentives

    Fear and asymmetric incentives kill more upside than bad ideas ever will.

    If last week was about how the system filters ideas, this is about why people inside it behave the way they do.

  11. 11

    Ownership

    The Handoff

    One thing experience teaches you quickly:

  12. 12

    Wrap-up

    The Lessons That Stick

    Over the last 12 weeks, I’ve written about systems, incentives, handoffs, recoverability, and the messy reality of how work actually gets done.

  13. Epilogue

    Epilogue

    The Porch Light — Epilogue

    A funny irony about these last 12 weeks…