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    News

    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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    Copyright: © 2024 Massive Studios

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    Latest Episodes:
    Migrating from Infrastructure as Code Mar 19, 2025
    Show notes

    Adam Jacob (@adamhjk, CEO/Founder @thesysteminit) talks about the evolution and intersection of DevOps 2.0, Infrastructure as Code (IaC), and what’s next

    SHOW: 907

    SHOW TRANSCRIPT: The Cloudcast #907 Transcript

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

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

    NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS"

    SHOW SPONSORS:

    • Try Postman AI Agent Builder Today
    • Cut Enterprise IT Support Costs by 30-50% with US Cloud

    SHOW NOTES:

    • System Initiative website
    • Adam on The Cloudcast #729

    Topic 1 - Welcome back to the show. We last spoke mid-2023. For those that missed that show, tell us about your background…

    Topic 2 - When we last spoke, we talked about DevOps 2.0. Give everyone an update on the state of the industry. DevOps 2.0, IaC, etc. Where are we at in that journey? For instance, what’s broken with IaC in the existing approaches and why a new approach?

    Topic 3 - One thing I’ve noticed in research for this topic is the move to visual and UI to conceptualize the environment and the corresponding actions. APIs and command lines will always have a place but what are your thoughts on this trend? I personally fall asleep every time someone gives a talk an industry conference and they pull up the command line for their demo. But, I’m also a visual learner.

    Topic 4 - When I’ve thought about both DevOps and IaC in the past, my mind immediately jumps to both complexity and dependencies. What do developers today have to consider and have we made any advances here?

    Topic 5 - Are there new metrics for success? With DevOps is was number of code commits, with IaC it was number of seamless deployments and actions. What do development teams look for today as the consider new platforms and tools?

    Topic 6 - I can see this being an area that could be impacted by AI in a few ways: 1. the summarization of large amounts of data 2. Digital Twins and simulations and 3. Agentic AI performing tasks based on conditions. What are your thoughts on AI here?

    Topic 7 - If anyone out there is interested, what’s the best way to get started?

    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Bluesky: @cloudcastpod.bsky.social
    • Twitter/X: @cloudcastpod
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Decoding Corporate Communications Mar 16, 2025
    Show notes

    How well does your company handle internal and external corporate communications? Are company town halls a nightmare? How should you engage with them and how can the company manage them better?

    SHOW: 906

    SHOW TRANSCRIPT: The Cloudcast #906 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 SPONSORS:

    • Try Postman AI Agent Builder Today
    • Cut Enterprise IT Support Costs by 30-50% with US Cloud


    SHOW NOTES:

    INTERNAL, EXTERNAL AND TEAM COMMUNICATIONS - COULD IT BE BETTER HANDLED?

    • Most internal corporate communications are bland—full of platitudes, at best boring, and at worst, demotivating. How can this be changed? Is any company doing this well?
    • What’s the best way to deliver internal communications? AI-generated emails? Short videos? Live all-hands webinars? Smaller in-person meetings? Does any of this actually work?
    • Southwest’s decision to end free checked bags is yet another example of corporate communication gone wrong.The CEO’s comments seem out of touch—maybe saying less is sometimes more? If you make an unpopular decision, should you avoid compounding the problem with excessive justification?
    • How do you personally process internal communications? Do you listen to all-hands meetings while walking the dog? Limit your consumption? Read summaries? Meditate afterward? What hacks or best practices work?
    • Are executive town halls doomed to fail? Leaders often seem to hold them out of obligation rather than genuine interest. Are we asking too much? Town halls aren’t great for deep discussions, but empty platitudes ring hollow. Is there a better way?

    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Twitter/X: @cloudcastpod
    • BlueSky: @cloudcastpod.bsky.social
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    AI Impacts Across Organizations & Startups Mar 12, 2025
    Show notes

    Jon Duren, Sr. Practice Manager, AI & Data @wwt_inc & Druce MacFarlane, Product @Infoblox talks about the intersection of AI, Startups, and Enterprise Trends.

    SHOW: 905

    SHOW TRANSCRIPT: The Cloudcast #905 Transcript

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

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

    NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS"

    SHOW SPONSORS:

    • Try Postman AI Agent Builder Today
    • Cut Enterprise IT Support Costs by 30-50% with US Cloud

    SHOW NOTES:

    • WWT website
    • WWT AI Proving Ground
    • Infoblox website
    • Startup Lantern Podcast

    Topic 1 - Jon and Druce welcome to the show. Give everyone a quick introduction…

    Topic 1a - You also have a podcast, tell everyone about that…

    Topic 2 - AI has thrown the world of cybersecurity a curveball.. Druce, how are you seeing AI impact the typical conversations you are involved in?

    Topic 3 - How is AI affecting start-up companies, thinking beyond all the AI-specific startups, how is AI going to impact the entrepreneur who’s trying to launch a non-AI company? What should they know and think about AI when starting a new company?

    Topic 4 - You both talk to a lot of customers about AI, especially to Enterprise customers. Let’s separate the hype from the practical. Where are organizations typically in their AI journey in early 2025? Have we moved beyond the chatbot yet

    Topic 5 - I see several organizations considering AI but struggling with ROI. What are you seeing, and how do you help organizations overcome this hurdle? How long is ROI measured with AI projects? It’s not 3-5 years anymore.

    Topic 6 - Is the industry moving too fast? Jon and I have had conversations in the past where organizations just can’t absorb the changes in hardware and models (just a few examples). How can an organization commit to a path that we know will change in 12 months

    Topic 7 - Tell everyone where they can find your podcast. Also, If anyone is interested, what’s the best way to get started on their AI journey?

    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Bluesky: @cloudcastpod.bsky.social
    • Twitter/X: @cloudcastpod
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Five Things I Did This Week Mar 09, 2025
    Show notes

    Does your management chain know what you’re doing to bring value to your company, your group or just your role? How do you communicate value for accountability, visibility, and promotability?

    SHOW: 904

    SHOW TRANSCRIPT: The Cloudcast #904 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 SPONSORS:

    • Try Postman AI Agent Builder Today
    • Cut Enterprise IT Support Costs by 30-50% with US Cloud


    SHOW NOTES:

    • Jeff Bezos’ API Mandate, and 5 Rules surrounding it
    • Jensen Huang’s NVIDIA “Top 5 Things” email


    DO YOU PROVIDE STATUS, ACCOUNTABILITY, OR DIRECTION ON YOUR WORK ACTIVITIES?

    • Lots of things could be perceived as negative, but how are you finding the positive?
    • How do you keep track of your work? How do you communicate your work? Are they well aligned to company goals?
    • In tough job markets, accountability is a valuable asset to have
    • How is your management chain communicating the group’s work upward and to other teams?
    • Do you ask what shouldn’t be done, where something else could occupy that time?
    • Does management use it as a way to educate others about functions of the business? (cross-team efforts)

    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Twitter/X: @cloudcastpod
    • BlueSky: @cloudcastpod.bsky.social
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Cloud & AI News Trends for February 2025 Mar 05, 2025
    Show notes

    Brian Gracely and Brandon Whichard discuss the top stories in Cloud and AI from February 2025 including NVIDIA’s earnings, Hashicorp, Intel’s CEO trio, Developer Co-Pilots, and RIP Skype.


    SHOW: 903
    SHOW TRANSCRIPT: The Cloudcast #903 Transcript
    SHOW VIDEO: https://youtube.com/@TheCloudcastNET
    CLOUD NEWS OF THE WEEK: http://bit.ly/cloudcast-cnotw
    NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS"
    SHOW SPONSORS:

    • Try Postman AI Agent Builder Today
    • Cut Enterprise IT Support Costs by 30-50% with US Cloud

    SHOW NOTES:

    • Link to February 2025 news and articles

    SEGMENTS COVERED IN THE SHOW:

    • Good Old Fashioned Cloud News
    • The AI Innovation Continues

    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Bluesky: @cloudcastpod.bsky.social
    • Twitter/X: @cloudcastpod
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Bathing in the Confusion around GenAI Mar 02, 2025
    Show notes

    Right now the news around GenAI seems scattered, all of the place, and confusing. Let’s dig into what’s working, what’s not, and where some future trends are heading.

    SHOW: 902

    SHOW TRANSCRIPT: The Cloudcast #902 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 SPONSORS:

    • Try Postman AI Agent Builder Today
    • Cut Enterprise IT Support Costs by 30-50% with US Cloud


    SHOW NOTES:

    • Most AI Investments Will Lose Money as Market Enters ‘Greed’ Cycle (Vinod Khasla, VC)
    • My LLM CodeGen workflow (Harper Reed)
    • "Gen AI: Too Much Spend, Too Little Benefit?" (Goldman Sachs)
    • Microsoft cancels leases on Data Centers for AI
    • NVIDIA announces Q4 earnings
    • An interview about AI unknowns (Stratechery)


    IF YOU’RE CONFUSED ABOUT AI, YOU’RE NOT ALONE.

    • There is a ton of AI out there, but it’s not always simple
    • There’s a ton of AI out there, but it’s not always affordable
    • There’s a ton of AI out there, and sometimes it blows our mind
    • There’s a ton of AI out there, and open source is starting to be disruptive (again)
    • There’s a ton of AI out there, and people are trying to forecast a future that changing too fast
    • There’s a ton of AI out there, and people are struggling with technology and politics overlapping so much


    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Twitter/X: @cloudcastpod
    • BlueSky: @cloudcastpod.bsky.social
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Developer Assistance with Coding Co-Pilots Feb 26, 2025
    Show notes

    Andrew Filev (@andrewsthoughts, Founder @zencoderai) talks about the state and future of developer coding co-pilots.

    SHOW: 901

    SHOW TRANSCRIPT: The Cloudcast #901 Transcript

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

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

    NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS"

    SHOW SPONSORS:

    • Try Postman AI Agent Builder Today
    • Cut Enterprise IT Support Costs by 30-50% with US Cloud

    SHOW NOTES:

    • ZenCoder website

    Topic 1 - Welcome to the show. Tell us about your background…

    Topic 2 - As someone who built and ran a large organization and continued to invest in other startups, what’s your take on startups and funding in today’s AI frenzy world? In your Wrike days did you ever foresee a time when funding rounds would be bigger than most valuations from years ago? Is this a sustainable investment model?

    Topic 3 - One of the leading use cases that came from GenAI and LLM’s is coding co-pilots. It might be the biggest and most profitable use case. What are your thoughts on Coding Co-pilots as whole and the state of the industry?

    Topic 4 - What makes a good coding co-pilot? Are their advantages to models trained specifically on coding How does that compare to the frontier LLM’s and their size and abilities?

    Topic 5 - We see lots of talk of coding co-pilots potentially hurting the industry. Lots of click bait headlines that coding is going away with agentic AI or Comp Sci degrees and junior employees might not be needed anymore. What are your thoughts on this?

    Topic 6 - Some argue that by having a co-pilot do the easy work, some developers might get lazy and the underlying fundamentals of development techniques might disappear. Others say this will elevate developers to new levels of productivity. What’s your view?

    Topic 7 - If anyone out there is interested, where can they go for more info or to contact you?

    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Bluesky: @cloudcastpod.bsky.social
    • Twitter/X: @cloudcastpod
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    What is your industry's DeepSeek moment? Feb 23, 2025
    Show notes

    We reached show #900!! We explore what happens when your industry experiences it’s DeepSeek moment, and how prepared you are across technology, organizational and economic changes.


    SHOW: 900

    SHOW TRANSCRIPT: The Cloudcast #900 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:

    • Cloud News of the Month - January 2025 - DeepSeek
    • Best 100 Technology Podcasts
    • Top Cloud Computing Podcasts
    • Top Software Engineering Podcasts
    • Top IT Podcasts


    WHAT EVENTS WOULD COMPLETELY CHANGE YOUR INDUSTRY? ARE YOU PREPARED?

    • It’s still playing out, but DeepSeek felt like a reset moment in this AI Journey the industry is having. It forced a lot of people to rethink a number of commonly held beliefs in the industry.
    • We’re not really talking about things like industry consolidation, wars, pandemics, but obviously that has ripple effects.
    • Interest rates obviously impact every industry, but they tend to change over quarters, not days.
    • We’ve seen things happen that impact industries temporarily, but don’t necessarily reshape the generally held rules - Oil/Energy, Hybrid/Electric Cars, IT/Cloud,
    • Internet “reimagined” a number of industries - Media, Advertising, Restaurants, etc.
    • Autonomous driving. Faster drug discovery. Discovery of new materials.
    • Financial crashes tend to happen about once a decade, when bubbles burst. Is the AI bubble next?
    • How much could you shift your IT budget in a year?
    • How much could you change/adjust/adapt your workforce in a year?
    • How much could you change the business model of your company in a year?
    • What law or regulation does your company fear the most?
    • What gov’t decision would most impact your company/industry?


    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Twitter/X: @cloudcastpod
    • BlueSky: @cloudcastpod.bsky.social
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    VMware Migrations Feb 19, 2025
    Show notes

    Madhura Maskasky (@madhuramaskasky, Chief Product Officer at @Platform9Sys) talks about the current state of the VMware virtualization market, thoughts on migrations, and factors to consider to speed migrations.

    SHOW: 899

    SHOW TRANSCRIPT: The Cloudcast #899 Transcript

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

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

    NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS"

    SPONSORS:

    • Take your personal data back with Incogni! Use code CLOUDCAST at the link below and get 60% off an annual plan: http://incogni.com/cloudcast

    SHOW NOTES:

    • Platform 9 (website)
    • Platform 9 Press Release on VMware Migrations
    • The Cloudcast #158 - Private Clouds with Platform 9
    • The Serverless Cast #1 - Project Fission


    Topic 1 - Welcome back to the show. For those that don’t know, you are a long time returning guest. It’s been about 7 years since the last time we spoke, and this is also the third time we’ve talked to you and the folks over at Platform9. Before we jump in, tell us about your background…

    Topic 2 - Our topic today is VMware Migrations. As we’ve documented many times on the podcast, VMware and its customers are in flux. Many are evaluating whether they should stay or they should go. When you speak to customers considering this, what should they consider?

    Topic 3 - In general we keep hearing things like VMWare ELA’s that are no only on 3 year renewal and a price hike of 3x, 5x, even 10x. What are you seeing? Is this a limited window of opportunity as customers make that decision to move off or lock in for another 3 years?

    Topic 4 - I see two sides to this: the business side and the tech side. I see this potentially being much harder on the technical side. While it might be possible to build a business case, the technical lock-in to the hypervisor technology tends to be a factor in conversions. Rebuilding years worth of virtual networking, storage links, etc. How do you advise customers on this today?

    Topic 5 - These migrations take time. Sometimes we are talking about installations in the tens of thousands of vms and and the migrations taking months to years to complete. Why would an organization go to the cost and the trouble to switch platforms?

    Topic 6 - Let’s say an organization decides to pull the trigger. My immediate thought goes to Day1+ actions and operations. New platforms, new tools, new constructs. VMware installs tend to be very sticky because careers have been built on their product portfolio and expertise around that. Some engineers carry a large number of certifications and have a lot of money and time invested. How do you talk customers through this and help them?

    Topic 7 - Let’s close out there. Where can our listeners go for more information?


    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Bluesky: @cloudcastpod.bsky.social
    • Twitter/X:

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    How will AI impact your IT budget? Feb 16, 2025
    Show notes

    As AI begins to make its way into the Enterprise, how will the experimentation, adoption and operations of AI impact 2025 and beyond IT budgets?


    SHOW: 898

    SHOW TRANSCRIPT: The Cloudcast #898 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:


    WHERE WILL IT BUDGETS MOST LIKELY BE IMPACTED BY AI IN 2025-2026?

    • Is your focus on human-augmented capabilities or human-replacement capabilities?
    • If you’re buying AI as part of SaaS services, will the pricing be seat-based (human-augmented) or usage-based (human-replacement), or some combination of both?
    • Are you directly paying for AI-capabilities, or is AI being positioned as “free”, but the other services are becoming more expensive?
    • Are you expanding your predictive AI projects (and data-science teams), or primarily focused on GenAI related projects?
    • Are you buying AI resources from the cloud providers, or from AI-specific hosting providers, or buying GPUs for private-cloud usage?
    • Are you planning to use standard AI tools, or do you plan to training/align your own models with your data?
    • Do you have a cost-control capability for your AI projects yet?
    • What are your success-criteria for POCs, Experiments, Trials?
    • Are you upskilling existing staff, or hiring AI-specific staff? Or using external consulting?


    FEEDBACK?

    • Email: show at the cloudcast dot net
    • Twitter/X: @cloudcastpod
    • BlueSky: @cloudcastpod.bsky.social
    • Instagram: @cloudcastpod
    • TikTok: @cloudcastpod


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

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