Jason Block - JW Block

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.

Stone castle on a calm moat beside a scattering windstorm of numbers and charts, contrasting durability against momentum

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?

Massive concrete dam holding back turbulent dark water with golden light leaking through cracks

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.

Retro-futurist illustration of a person holding up a massive machine versus an autonomous machine running on its own

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.

Film reel dissolving into code streams, representing AI transition from consumer video to enterprise

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.

Retro-futuristic illustration of a vault-like server room with its door left open, symbolizing Anthropic's data leak

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.

Retro-futurist cutaway of an organizational machine revealing hidden informal pathways beneath clean gears

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.