The Reasoning Show

The Reasoning Show AI moves fast. Thinking clearly matters more.

The Reasoning Show cuts through the hype to explore how the smartest people in enterprise AI actually make decisions — the strategy, the tradeoffs, and the hard lessons no press release mentions.

Every week, hosts Aaron Delp and Brian Gracely sit down with the founders building the tools, investors funding the shift, and operators running AI in the real world. Not hype. Not panic. Just clear-headed conversations with people who have to make actual decisions.

Because the AI revolution isn't just happening. It's being reasoned through.

New shows every Wednesday and Sunday.

Topics: Enterprise AI strategy · LLMs in production · AI leadership · Agentic AI · Digital Sovereignty · Machine Learning · AI startups · Cloud Computing

All Episodes

The Reasoning Show

The Future of Enterprise Software?

February 04, 2026 • Massive Studios

0:00 | 27:11

Are we ready to move into an era of wild predictions about where the future of Enterprise software is headed in 2026 and beyond?

SHOW: 999

SHOW TRANSCRIPT: The Cloudcast #999 Transcript

SHOW VIDEO: https://youtube.com/@TheCloudcastNET

CLOUD NEWS OF THE WEEK: http://bit.ly/cloudcast-cnotw

CHECK OUT OUR NEW PODCAST: "CLOUDCAST BASICS"

SHOW NOTES

WHAT HAPPENS TO ENTERPRISE SOFTWARE NEXT?

How much do enterprises want to write their own software?
How much do enterprises wish they could write more software?
How much do enterprises not understand the economics of owning their own software?
How much does “big SaaS” or just “big Enterprise software” actually help because people already know it?
Is it possible that this new Agentic-driven software could create a type of new software community?
Are “open” software communities prepared for the emerging economics of AI-created software?

FEEDBACK?