Read the Reconciliation, Not the Metric
A company-invented profit metric is only as honest as its bridge to GAAP. The We Company's 2019 S-1 reconciliation, re-added line by line, and a reading rule I tried to break....
Key Knowledge
The Technical Due Diligence Checklist
A comprehensive checklist for evaluating startup technology: architecture, code quality, infrastructure, team, and security.
Brex's 58% Haircut: The Fintech Reckoning Arrives
Capital One acquires Brex for $5.15 billion, 58% below peak valuation....
The Fintech Winter Thaw: Who Survived and Why
The fintech funding winter wasn't death - it was a reset. Capital is flowing to companies with real traction and clear unit economics. The 2021 playbook is dead....
Bootstrap vs VC in 2026: The Math Changed
Down-rounds hit 15.9% in 2025. AI startups took 61% of all global venture funding. The 2026 math favors bootstrap more than any time since ZIRP ended....
Why Most AI Startups Will Fail by 2027
Why a wave of AI startups will collapse in 2027: unsustainable unit economics, model commoditization, and the venture math that no longer works....
The Pivot That Kills
Most pivots destroy more value than they create. Knowing when to iterate versus pivot is a survival skill....
The MVP Excuse: When 'Minimum' Became an Excuse for Garbage
MVP was meant to be a discipline for validated learning, not permission to ship half-finished software....
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....
The Exit Planning Gap
Most 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....
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....
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