What CompuServe Taught Me About Platform Death
CompuServe had first-mover advantage, loyal users, and great technology. They still lost to AOL....
The SaaS Pricing Lie: Why Per-Seat Doesn't Scale
Per-seat pricing is a legacy model from when humans were the unit of work. AI is exposing the lie: vendors want seats, not efficiency. Here's what's replacing it....
The Outsourcing Boomerang
The outsourcing boomerang: every company that outsourced its core engineering eventually had to bring it back in, at higher cost and worse quality....
When to Kill Your Company
Knowing when to shut down is harder than knowing when to start. The sunk cost fallacy kills more founders than failure....
Meetings Are Bugs in Your Organization
Unproductive meetings cost $37 billion annually. They're not collaboration - they're organizational bugs. Here's how to diagnose the root cause and fix the process....
The Exit Planning Gap
48% of founders planning to sell have no exit strategy. M&A accounts for 85%+ of VC-backed exits. The founders who get the best outcomes planned for them....
AI Sovereignty: The Expensive Illusion Every Nation Is Chasing
Every nation wants AI sovereignty. Only the US and China have anything close to it....
Open Source Isn't Free
Open source software has a price tag of $0 and a total cost of ownership that can dwarf commercial alternatives....
Why a Priced Round is "Safer" Than a SAFE
Despite the comforting acronym, a SAFE is often anything but safe for a founder. Learn why priced rounds offer better protection for your cap table....
Why Bootstrapped Companies Win
VC funding creates misaligned incentives. Bootstrapped companies often build better products and more sustainable businesses....
The 10 Architecture Decisions That Kill Startups
The architecture mistakes that kill startups: premature microservices, wrong database choices, god objects, missing observability, and more....
The Technical Due Diligence Checklist
A comprehensive checklist for evaluating startup technology: architecture, code quality, infrastructure, team, and security....
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