The Enterprise AI Show

The Enterprise AI Show explores the AI journey for Enterprise companies around the world. [formerly The Cloudcast]


As the AI revolution moves from experimentation to execution, The Enterprise AI Show provides the clarity needed to lead. Join Aaron Delp and Brian Gracely as they explore the intersection of generative AI, enterprise systems, and global business strategy. Each episode features clear-headed conversations with the people making actual decisions—founders, investors, and practitioners—focusing on the technical architectures and business models that drive real-world ROI.


New shows every Wednesday and Sunday.


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

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Does your CEO know what your group does?

Does your CEO know what your group does?

Does your boss’ boss know what your group does? How far up the org chart is it before your group is unknown? Let’s look at ways that your group can make sure it has visibility up the ranks of your man...

12 Tammi 202522min

Career Advice in 2025

Career Advice in 2025

As we start in 2025, we wanted to offer advice on job searching and evaluating roles. The market and the interviewing process have shifted; what do you need to know in 2025 if you seek a new opportuni...

8 Tammi 202540min

The Cloudcast #886 - Reflections, Resolutions and Beginning 2025

The Cloudcast #886 - Reflections, Resolutions and Beginning 2025

As a new year is upon us, let's make a checklist of the most important areas to focus upon to make Q1 successful and set up the rest of 2025 for success. SHOW: 886 SHOW TRANSCRIPT: The Cloudcast #886...

5 Tammi 202532min

Auth in the Age of AI Agents

Auth in the Age of AI Agents

Jake Moshenko (@jacobmoshenko, CEO of @AuthZed) talks about the challenges of securing AI interactions, as well as authentication best-practices for AI Agents and RAG patterns. SHOW: 885 SHOW TRANSC...

1 Tammi 202537min

2024 Year-End Review and 2025 Predictions

2024 Year-End Review and 2025 Predictions

It’s that time of the year again. Brian and Aaron wrap of the year in Cloud and AI, and make predictions for 2025. SHOW: 884 SHOW TRANSCRIPT: The Cloudcast #884 Transcript SHOW VIDEO: https://youtu...

25 Joulu 202446min

Evaluating Market Changing Trends

Evaluating Market Changing Trends

If AI is going to be the next big trend in tech and impact every aspect of society, how do you go about trying to evaluate where it is today and where it might be in a few years or a decade? SHOW: 8...

22 Joulu 202426min

2024 Year End Mailbag

2024 Year End Mailbag

It’s that time of the year… Aaron and Brian answer emails and questions for the second half of the year. SHOW: 882 SHOW TRANSCRIPT: The Cloudcast #882 Transcript SHOW VIDEO: https://youtube.com/@The...

18 Joulu 202448min

 Does the AI startup ecosystem need Yacht Rock infrastructure?

Does the AI startup ecosystem need Yacht Rock infrastructure?

In the late 70s and early 80s, a music revolution started because a bunch of talented musicians played on 100s of albums, behind the scenes. Would the AI startup community benefit from a similar infra...

15 Joulu 202417min

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