I was at an investor meeting the other day. It wasn’t for my own company, but I got to watch a lot of founders proudly talking about their businesses. It reminded me of all the posts you see on LinkedIn where people brag about raising $10 million from a venture capitalist like it’s the ultimate achievement.

When Jack Dorsey announced on February 26, 2026, that Block (the parent of Square and Cash App) was cutting more than 4,000 jobs—nearly half its workforce from over 10,000 to under 6,000—the markets responded enthusiastically. Shares surged 20–25% in after-hours trading, and Block raised its 2026 gross profit guidance to ~$12.2 billion after strong 2025 results.