Jason Block - JW Block

Blueprint schematic of a bureaucratic approval machine with disconnected sections

Systems Thinking

The Audit Nobody Wants to Run

Every business carries operational dead weight it stopped questioning. The diagnostic is three questions. The results are usually uncomfortable.

Wes Anderson style pastel diorama of a miniature fortress wall made of airline tickets with a crack and a tiny AI robot walking through the gap

AI & Tech

MCP Just Handed Every Travel Nerd a Loaded Weapon

The travel technology stack has always been a fortress. Decades of proprietary protocols, arcane fare-filing formats, and GDS middleware that requires a PhD in EDIFACT to navigate. That barrier just got a lot lower.

Wes Anderson style pastel diorama of three parallel miniature assembly stations converging at a central merge point with a tiny completed car

Systems Thinking

Stop Building in Single File

Ford's Long Beach skunkworks revealed a manufacturing heresy: stop doing things in order. The mental model underneath — sequential vs. parallel process architecture — applies to every business that's ever wondered why everything takes so long.

Wes Anderson pastel diorama of a miniature office desk with an untouched rubber stamp on papers, overflowing powder-blue inbox tray and empty mint-green outbox tray

Systems Thinking

I'm Going to Stop Tracking Productivity and Start Tracking How Long Decisions Take

I've been watching decisions idle for weeks while every productivity metric looks fine. Here's the experiment I'm running to find out if decision speed is what actually matters.

Miniature desk with oversized gold coins tipping onto a calculator showing a negative number

Business Growth

Three Numbers That Expose Whether Your Business Is Growing or Just Getting Bigger

I track three numbers across my businesses that have been more predictive of real health than any revenue chart on a quarterly slide deck. They cut through the noise that top-line growth creates.

Wes Anderson style pastel diorama of a miniature boxing ring with two office chairs, one knocked sideways, and a crumpled memo on the canvas

ai

The AI Gave You Bad Advice Because You Didn't Fight It

Most people use AI the way they used to use Google. Type a question, take the first answer, move on. The result is predictable: safe, generic, convergent mush that could apply to any company in any industry.

Entrepreneurship

Your Price Is Your First Pitch

Low fees don't communicate accessibility. They communicate doubt. The professional who charges $500 for complex work is losing to the one who charges $5,000. Not on quality. On positioning.

Wes Anderson pastel diorama with miniature televisions and a piggy bank on a mint countertop

Entrepreneurship

The $69 Ceiling Is Real and Your Subscription Product Will Hit It

The average American household spends $69 a month on streaming subscriptions. That number has barely moved in a year. Not because people stopped caring about content. Because they got disciplined.

Two diverging roads leading to dead ends with a third middle path opening toward a balanced regulatory gateway

AI & Tech

Two Roads for AI Regulation and Why Both Are Dead Ends

The AI regulation debate has collapsed into two camps, and I think they're both wrong. The answer might be hiding in the last place I expected.

Abstract retro-futuristic scale tilting under structural pressure, navy and amber tones

AI & Tech

The SaaSpocalypse Is Real. The Diagnosis Is Wrong.

A trillion dollars in SaaS market cap vanished in a few weeks. Wall Street looked at a few impressive AI demos and concluded that enterprise software is dead. It isn't.

Retro-futuristic factory scoreboard with meaningless achievement badges and machines producing nothing

AI & Tech

The Fastest Way to Win Meta's AI Contest Is Also the Dumbest

If you want to understand why so many companies are spending fortunes on AI and getting nothing back, look no further than Meta's internal leaderboard for token consumption.

Three diverging pathways representing build, buy, and borrow decisions in a blueprint style

Systems Thinking

Build It, Buy It, or Borrow It

I have a graveyard of SaaS subscriptions I paid for instead of building and custom tools I built instead of buying. After enough mistakes, a pattern emerged in what made some decisions right and others wrong.