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.
Decoding AI, Entrepreneurship, Business Growth, and Systems Thinking for modern builders and leaders.
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Every business carries operational dead weight it stopped questioning. The diagnostic is three questions. The results are usually uncomfortable.
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.
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.
Each week I share my learnings with you in an easy to consume format. I hope you find it useful.
- JW
I'm an entrepreneur, operator, investor, and writer.
By day I run businesses in travel; by night I build and test systems at the edge of what's changing, especially in AI and automation. I write and speak about building durable companies, turning messy execution into repeatable process, and using powerful new tools without fooling yourself -- so what you ship is reliable, measurable, and worth maintaining.
If you're building, leading teams, or trying to make sense of the shift, you're in the right place.
Every business carries operational dead weight it stopped questioning. The diagnostic is three questions. The results are usually uncomfortable.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.