Blog
Retrospective reflections written in 2026 on operating roles from 2000 onward.
When Alignment Is the Real Bottleneck
We blame speed, resources, and competition. But most companies stall because the people in the room cannot agree on what they are building.
Architecture Decisions That Outlive Teams
The code you write today will be maintained by people you will never meet. The org chart you draw will outlast everyone in the room. Choose accordingly.
9/11 and Leading Through Uncertainty
Twenty-five years ago, the world changed overnight. I was at Nike, building something unproven, when uncertainty became the only constant.
Building Commerce in a Post–Dot-Com World
In 2000, the internet had just been humbled. The dot-com crash reset expectations across every boardroom. Capital retreated. Public markets corrected sharply. Digital initiatives that had been treated as inevitable were suddenly treated as speculative.