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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Evolutions in Security Monitoring

Evolutions in Security Monitoring

Huxlee Barbee (@huxley_barbee, Head Security Prod Mktg @DataDogHQ) talks about the challenging odds of preventing security attacks, managing configuration mistakes, scaling security through monitoring...

6 Loka 202135min

Innovator's Dilemma Part 1

Innovator's Dilemma Part 1

Part 1 (of 2) looking at a recent example of how The Innovator’s Dilemma is playing out between the biggest clouds and the challenging upstarts. SHOW: 554 CLOUD NEWS OF THE WEEK - http://bit.ly/clou...

3 Loka 202123min

The State of Cloud Security

The State of Cloud Security

Josh Stella (@joshstella, Founder/CEO of @FugueHQ) talks about the differences between cloud security and data center security, the value businesses place on security implementations, and enabling gov...

29 Syys 202141min

Developing New Habits in COVID

Developing New Habits in COVID

COVID has changed the world over the past two years. But how many of the technology changes we’ve made will remain, and which ones may revert back to pre-COVID standards? SHOW: 552 CLOUD NEWS OF THE ...

26 Syys 202121min

Managing Tech Burnout

Managing Tech Burnout

Michael Cucchi (VP of Product @PagerDuty) talks about the challenges of increased hours, more frequent incident responses and overall tech burnout as a result of the 2020-21 pandemic. SHOW: 551 CLO...

22 Syys 202137min

The Evolution of MongoDB

The Evolution of MongoDB

The transition of @MongoDB from an open source project to commercially successful public company to cloud provider has been an interesting transition. One that many other software companies are lookin...

19 Syys 202126min

Remotely Managing All The Things

Remotely Managing All The Things

Ev Kontsevoy (@kontsevoy, Cofounder/CEO @GoTeleport) talks about the state of the art in remote management, especially for Kubernetes environments, and how Teleport simplifies security for remote acce...

15 Syys 202138min

Cloud Jobs - Stay, Leave or Quit

Cloud Jobs - Stay, Leave or Quit

There’s been quite a bit of debate recently on whether or not to stay in a role, look around for something new, or just quit tech all together. What’s the right choice? Let’s explore some options and ...

12 Syys 202125min

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