The Room Where It Happens
You got the invite. The calendar hold. The seat at the long table. Access without influence is a participation trophy for adults.
Latest
The Smartest Money in the Room Just Bet Against Software
Apollo just called private equity's software concentration a systemic failure of risk management. Their HALO thesis tells founders what AI actually makes more valuable.
Your Prices Are a Time Capsule and Nobody Has Opened It
Most small businesses set their prices once and never revisit them. Here's a three-question diagnostic for founders who suspect the number no longer matches the business.
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.
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.
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.
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.
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.
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.
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.
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 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.
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.
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.
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.
Investment
The Test That Separates a Moat From a Tailwind
When I evaluate a business for the family office, I run one test before anything else. If the wind reversed tomorrow, does the company still exist?
Investment
OpenAI's Retail Investor Play Isn't Democratization, It's a Price Floor
When I evaluate pre-IPO retail access from the family office side, I run a simple test. I ask: who benefits more from this transaction, the buyer or the seller? If the company is engineering broad ownership before a public listing, the answer is almost always the seller.
Entrepreneurship
The Owner-Reliance Discount
Every system you build is equity. Every process only you understand is a liability on the balance sheet.
AI & Tech
Slack Just Turned Slackbot Into the Agent You Actually Wanted
Slack announced more than 30 new capabilities for Slackbot today, transforming it from a simple chatbot into a full-spectrum enterprise agent powered by Anthropic's Claude and connected via MCP.
AI & Tech
OpenAI Kills Sora and the Era of AI Companies That Do Everything
OpenAI is shutting down Sora, the AI video platform it launched to enormous fanfare in late 2025. The consumer app, the API, and the website are all going dark. The billion-dollar Disney deal? Dead.
AI & Tech
Anthropic's Biggest Vulnerability Was a Checkbox
The most safety-conscious AI lab on the planet just leaked its most dangerous model through a misconfigured content management system.
AI & Tech
The AI That Tells the Emperor He's Naked
Interloom just raised $16.5M to map how companies actually operate. The product is compelling, but the real opportunity is much bigger than one startup's context graph.
Systems Thinking
Feedback Loops Are Eating Your Margin
Most operators think about margin as an output. Revenue minus cost equals profit. Margin erosion almost never shows up as a single line item you can point to and fix. It shows up as a pattern, a reinforcing cycle where one problem feeds another.
AI & Tech
Anthropic "Accidentally" Released a New Model. Sure They Did.
Anthropic released a new Claude model this week that wasn't supposed to be public. They called it an accident. The model appeared briefly, got pulled, and the story spread everywhere.