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.
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.
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.
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.