Substacks recommended by James Kaplan

Recommended by James Kaplan

Insights and tips for aspiring, current and experienced Engineering Leaders drawn from more than 15 years operating at this capacity

The 10 commandments of a good CTO are worth the sub. Principle-centered technology leadership focused on intellectual integrity, transparency and sustainable design.

- James Kaplan

The Modern Enterprise Unpacked

By Modern Enterprise

Insights and strategy for enterprise leaders navigating AI, innovation, and transformation. Stories that explain, challenge, and connect.

Focuses on how big organizations are actually adopting AI, modernizing tech stacks, and reshaping operating models. Focuses on "buy-side" issues like AI readiness and whether how enterprises should think about neo cloud services.

- James Kaplan

What's Hot 🔥 in Enterprise IT/VC

By Ed Sim

Ed Sim's (@boldstartvc) weekly readings and notes on enterprise VC, software, and scaling startups

Ed is one of my favorite people in VC because he emphasizes speed, creativity and authenticity!

- James Kaplan

Not Boring by Packy McCormick

Tech strategy, analysis, and philosophy, but not boring.

I love the optimism about technology and how it can shape tomorrow's world.

- James Kaplan

Prosaic Times

Recommended by James Kaplan