What happens when you try to monitor something fundamentally unpredictable? In this featured guest episode, Wayne Segar from Dynatrace joins Corey Quinn to tackle the messy reality of observing AI workloads in enterprise environments. They explore why traditional monitoring breaks down with non-deterministic AI systems, how AI Centers of Excellence are helping overcome compliance roadblocks, and why “human in the loop” beats full automation in most real-world scenarios.

From Cursor’s AI-driven customer service fail to why enterprises are consolidating from 15+ observability vendors, this conversation dives into the gap between AI hype and operational reality, and why the companies not shouting the loudest about AI might be the ones actually using it best.

Show Highlights

(00:00) - Cold Open
(00:48) – Introductions and what Dynatrace actually does

(03:28) – Who Dynatrace serves

(04:55) – Why AI isn't prominently featured on Dynatrace's homepage

(05:41) – How Dynatrace built AI into its platform 10 years ago

(07:32) – Observability for GenAI workloads and their complexity

(08:00) – Why AI workloads are "non-deterministic" and what that means for monitoring

(12:00) – When AI goes wrong

(13:35) – “Human in the loop”: Why the smartest companies keep people in control

(16:00) – How AI Centers of Excellence are solving the compliance bottleneck

(18:00) – Are enterprises too paranoid about their data?

(21:00) – Why startups can innovate faster than enterprises

(26:00) – The "multi-function printer problem" plaguing observability platforms

(29:00) – Why you rarely hear customers complain about Dynatrace

(31:28) – Free trials and playground environments

About Wayne Segar

Wayne Segar is Director of Global Field CTOs at Dynatrace and part of the Global Center of Excellence where he focuses on cutting-edge cloud technologies and enabling the adoption of Dynatrace at large enterprise customers. Prior to joining Dynatrace, Wayne was a Dynatrace customer where he was responsible for performance and customer experience at a large financial institution.

Links

Dynatrace website: https://dynatrace.com

Dynatrace free trial: https://dynatrace.com/trial

Dynatrace AI observability: https://dynatrace.com/platform/artificial-intelligence/

Wayne Segar on LinkedIn: https://www.linkedin.com/in/wayne-segar/

Sponsor

Dynatrace: http://www.dynatrace.com

How do you wrangle the chaos of AWS cost tools and live presentations? In this episode of Screaming in the Cloud, Corey Quinn is joined by AWS’s Bowen Wang and Matt Berk to break down their re:Invent talk and everything that almost went off the rails. From surprise tsunami alerts to last-minute feature changes, they explore the anxiety and art behind presenting at scale. They also look at how power user feedback shapes tools like the AWS Pricing Calculator, why storytelling matters more than specs, and what it’s like co-presenting with notes that say “make the rabbit joke.” They also discuss AWS’s internal planning process, how customers can get involved in talks, and where to catch them next.

Show Highlights

(0:00) Intro

(1:38) The Duckbill Group sponsor read

(2:35) The importance of collecting feedback before launching a product

(4:52) The difference between the intended use of a product and how it’s actually used

(8:52) How Bowen and Matt were able to be so prepared for their presentation

(13:01) What many people don’t realize goes into practicing for a presentation

(17:14) How having a storyline helped Bowen and Matt facilitate better breakout sessions

(18:26) The Duckbill Group sponsor read

(21:02) The importance of being able to go with the flow during presentations

(22:42) Why knowing your audience is essential for having a good presentation

(24:32) Choosing between breadth and depth when giving presentations

(25:05) Bowen and Matt’s advice for people who want to have their opportunity to give a talk with an AWS service team

(34:22) How to keep up with Matt and Bowen

About Matt Berk

Matt Berk is an AWS Principal Technical Account Manager at based in Brooklyn who's passionate about storytelling, cloud technologies, and FinOps. When he's not solving customer issues, Matt can be either be found in nature with his dog Ollie, at popular NYC restaurants, or at home planning his next trip to a theme park.

About Bowen Wang

Bowen Wang is a Principal Product Marketing Manager for AWS Billing and Cost Management Services, where she focuses on enabling finance and business leaders to better understand the value of the cloud and ways to optimize their cloud financial management. In her previous career, she helped a tech start-up enter the Chinese market. When she's not helping customers optimize their cloud costs, you can find her cheering for F1 races with her husband or juggling life as a mom to an energetic toddler and a playful poodle.

Links

• AWS Cloud Financial Management Blog Channel: https://aws.amazon.com/blogs/aws-cloud-financial-management/
• AWS Twitch Channel: https://www.twitch.tv/aws
• AWS Tech Tales: https://community.aws/livestreams/aws-tech-tales
• The authenticated AWS Pricing Calculator is now generally available: https://aws.amazon.com/blogs/aws-cloud-financial-management/the-authenticated-aws-pricing-calculator-is-now-generally-available/

What’s going on with Infrastructure as Code? On this episode, Corey is joined by Firefly CEO and Co-Founder Ido Neeman to discuss the findings of the State of IaC 2025 report. Throughout their chat, Corey and Ido discuss the evolution of IaC adoption in enterprises, the challenges of managing multi-cloud and multi-IaC environments, and the importance of disaster recovery as code. The conversation also touches on the rise of open-source projects like Open Tofu and the significant role of automation in cloud cost optimization. This episode not only reflects on recent trends, but highlights the importance of robust cloud governance and the continuous need for innovation amidst increasing cloud complexity.

Show Highlights

(0:00) Intro

(0:59) Firefly sponsor read

(1:29) Firefly's semi-pivot to AI

(2:54) The findings of the State of IaC 2025 survey

(5:40) How are people working in multi-cloud environments

(8:14) Is there a responsible way to use Helm charts?

(11:21) The currrent state of Pulumi

(12:46) Problems that can be encountered with large enterprises

(18:07) The continuum between innovation and optimization

(21:51) Firefly sponsor read

(22:31) Are companies actually adopting infrastructure as code?

(28:49) The most interesting ways that Ido has seen enterprises use IaC in production

(33:40) What's stopping companies from fully leveraging IaC?

(41:06) Where you can find more from Ido and Firefly

About Ido Neeman

Ido Neeman is CEO and co-founder of Firefly, and the former CEO and co-founder of Nuweba, the fast and secure serverless platform. To the diversity of roles he has held, he brings more than a decade's experience in the elite Israeli intelligence corps, and later led the technology portfolio at a hedge fund. Today, he is focusing on helping organizations tackle cloud chaos through Infrastructure as Code.

Links

• Firefly’s website: https://www.firefly.ai/
• The State of IaC 2025: https://www.firefly.ai/state-of-iac-2025
• Ido on Twitter: https://x.com/idoneeman?lang=en
• Ido on LinkedIn: https://www.linkedin.com/in/ido-neeman/?originalSubdomain=il

Sponsor

Firefly: https://www.firefly.ai/

How does one manage to simplify the complexities of the NAT Gateway? In this episode of "Screaming in the Cloud," Corey Quinn interviews Malith Rajapakse, a DevOps engineer who has recently received acclaim for his blog post discussing the Managed NAT Gateway. Where AWS lacks in its documentation, Malith is a NATural at breaking things down. He’s so great at it that Corey had to invite him on the show! Malith shares the story behind his popular post, his creative process, and his use of interactive diagrams and engaging content. He and Corey also discuss the challenges of documentation and making technical subjects more appealing. Thankfully, Malith has already done that in written form, so enjoy this episode as he speaks it into the world!

Show Highlights

(0:00) Intro

(1:24) The Duckbill Group sponsor read

(1:58) Malith's background before his blog post

(4:21) Why Malith wrote about the Managed NAT Gateway

(5:38) Corey's problems with Managed NAT Gateway and why Malith's blog post impressed him

(10:05) The interactive elements of Malith's blog post and how they were made

(12:21) Maltih's front-end experience

(14:47) Transitioning from front-end to DevOps through JavaScript

(16:20) The juxtaposition of Malith's blog post vs. AWS's official documentation

(18:05) How AWS's documentation of the managed NAT gateway isn't user-friendly

(22:27) Why Malith went all out for his first blog post

(23:17) Corey's constructive feedback for Malith

(26:05) Where you can find more from Malith

About Malith Rajapakse

Malith is a Devops engineer creating visualisations at https://malithr.com/.

Links

• Malith’s blog: https://malithr.com/
• Interactive AWS NAT Gateway: https://malithr.com/aws/natgateway/
• LinkedIn: https://www.linkedin.com/in/malith-rajapakse/
• Bluesky: https://bsky.app/profile/malithr.com
• Twitter: https://x.com/malithraj
• Reddit: https://www.reddit.com/user/mdilraj/
• Sam Rose’s blog: https://samwho.dev/
• Benjamin Dicken’s blog post on IO devices and latency: https://planetscale.com/blog/io-devices-and-latency
• Josh W Comeau’s blog: https://www.joshwcomeau.com/
• Killed By Google: https://killedbygoogle.com/

Sponsor

The Duckbill Group: duckbillgroup.com

Microsoft has its fingers in a lot of pots, but just how secure are said pots? On this episode, Corey is joined by Ann Johnson, Corporate Vice President and Deputy CISO of Microsoft's Customer Security Management Office. Ann talks about her 40-year professional journey and how it's culminated in her current role. Corey is known to “punch up” at the big guys in the tech industry, but he and Ann talk about the challenges of corporate leadership and being a public face in such a prominent company. Since it’s 2025, of course, they’re going to talk about AI’s pros and cons (and why it shouldn’t be used to make art).

Show Highlights
(0:00) Intro
(0:51) The Duckbill Group sponsor read
(1:25) What Ann's been up to since she and Corey last spoke 
(2:29) The makeup of Microsoft Security
(4:28) The unique company culture at Microsoft
(8:42) What's going on with Microsoft Azure
(10:31) How Ann handles the immense pressure of working in Microsoft Security
(14:13) The toxic nature of online criticism
(19:57) The Duckbill Group sponsor read
(20:24) The value of telling your leaders the truth
(23:31) Ann's thoughts on the current state of AI
(28:44) Properly defining what AI can and can't do
(30:54) Why Ann helps fund multiple STEM scholarships
(32:16) The need for the humanities alongside tech
(33:38)  Where you can find more from Ann Johnson

About Ann Johnson
Ann Johnson is Corporate Vice President and Deputy CISO at Microsoft. In this role, Ann drives all external engagement for the Microsoft Office of the CISO. She is a long-tenured, recognized thought leader on cybersecurity, published author, and a sought-after global speaker and digital author specializing in cyber resilience, online fraud, cyberattacks, compliance, and security. 

Ann challenges traditional schools of thought and cyber-norms–from the way the tech industry tackles cyber threats to the language it uses to communicate–and encourages the industry to get outside its comfort zones and expand how it addresses the evolving threat landscape with the power of technology and people. As a global cybersecurity leader and strategist, she is looking ahead at how today’s cybersecurity investments will impact tomorrow’s cybersecurity reality.  

Ann currently serves on the Board of Directors of N-Able, Human Security, Datavant, and is Member of the Board of Advisors for Cybersecurity Center of Excellence, WA and the Signal Cyber Museum Society. Ann is also an Executive Sponsor of the Microsoft Women in Cybersecurity Group.

Links

• Ann Johnson’s LinkedIn: https://www.linkedin.com/in/ann-johnsons/
• Microsoft Security: https://www.microsoft.com/en-us/security
• Afternoon Cyber Tea: afternooncybertea.com
  
  

Sponsor

The Duckbill Group: duckbillgroup.com

If you believed, they put a data center on the moon. No, for real, they did, and it’s partially thanks to Lili Rogowsky, partner at Atypical Ventures. Lili joins Corey to discuss her unconventional leap from law to venture capital. Although she made a sharp turn career-wise, Lili remains grounded in the often heartless world of venture capital—highlighting the importance of empathy and technical prowess in founding successful enterprises. Out of all resources, time carries the heftiest price tag, and this half-hour episode is a low-risk, high-yield investment.

Show Highlights

(0:00) Intro

(1:12) The Duckbill Group sponsor read

(1:46) How Corey (kinda) met Lili

(3:38) What attracted Corey to Atypical Ventures

(5:58) How Atypical helped put a data center on the moon

(8:34) VC “done right”

(9:59) What led Lili to run a VC firm

(13:43) Quitting jobs until you find something you like

(16:28) The Duckbill Group sponsor read

(16:54) The value of sharing your time

(21:44) Risk assessment, well-dressed horses, and punching up in comedy

(24:44) The importance of humility in life and business

(29:15) Where you can find more from Lili and Atypical Ventures

About Lili Rogowsky

Lili is a dynamic investor, attorney, advisor, and entrepreneur. She is a partner at Atypical Ventures, an early-stage fund that identifies and invests in “engineers with empathy” working on plausible science fiction.

A voracious reader driven by her curiosity and love of type 2 fun, Lili’s experience includes (in no particular order) mountaineering, visual arts, marine science, founding a law firm, cave/ shark diving (not necessarily at the same time), data privacy/ security, gardening, recruiting, battling NYC rats that eat her car, and interplanetary internet.

Links

• Atypical Ventures: atypical.com
• Email Lili: lili@atypical.vc

Sponsor

The Duckbill Group: duckbillgroup.com

Dropping and sharing files should be easy. What a novel idea. On this episode, Corey speaks with Timo Josten, the sole developer behind Dropshare. We bring up the fact that he’s the only guy working on it because the tool is quite impressive! Corey loves it and so does an entire community of folks on Github! Together, they discuss the evolution and functionality of Dropshare. Timo also shares how he balance of enhancing Dropshare, emphasizing user feedback, and customization options, all while offering feature updates and maintaining sustainability.

Show Highlights

(0:00) Intro

(1:06) The Duckbill Group sponsor read

(1:39) What does Dropshare do?

(6:10) Dropshare's impressive flexibility and dedicated community

(10:27) How Timo landed on Dropshare's business model

(12:38) What's new in Dropshare 6?

(16:09) The Duckbill Group sponsor read

(16:36) Determining what should be an update or part of the next version of Dropshare

(18:30) Dropshare’s iOS app

(21:04) The perks of being able to configure deletion in Dropshare

(25:45) Dropshare's thriving GitHub community

(29:26) Where you can find more from Timo and Dropshare

About Timo Josten

Timo Josten is the developer of Dropshare, the macOS and iOS app to upload anything anywhere.

Links

• Timo’s LinkedIn profile: https://www.linkedin.com/in/timo-josten-493962185/
• Timo’s personal website: https://josten.io
• Dropshare: https://dropshare.app/
• shitposting.pictures

Sponsor

The Duckbill Group: duckbillgroup.com

How you learn is important. Corey Quinn is joined by Aditya Bhargava, a Staff Software Engineer at Etsy and the author of Grokking Algorithms. They talk about the nuances of technical learning and the contrasting philosophies of "just in time" versus "just in case" learning. In this episode, Aditya emphasizes the importance of effective teaching methods and the value of incorporating fun things like drawings into technical explanations. This approach also bleeds into his illustrated Substack, DuckTypes. As Corey and Aditya discuss, a good, informative book doesn’t need to drag on, and this quick, insightful, 30-minute conversation is no different.

Show Highlights

(0:00) Intro

(1:24) The Duckbill Group sponsor read

(1:58) Corey's admiration for Aditya's writing

(5:40) How Aditya clearly explains AWS networking

(8:06) “Just in case” vs. “just in time”

(10:15) Why business books don't need to be hundreds of pages long

(14:19) Reading for pleasure vs. reading for work

(16:57) The Duckbill Group sponsor read

(17:24) Explaining Aditya's book on algorithms

(20:07) The great editor behind Aditya's book

(22:20) DuckTyped and how Aditya got into AWS networking

(25:16) Where networking folks fall in the era of the cloud

(28:12) The importance of staying up-to-date in your field

(31:46) Where you can find more from Aditya

About Aditya Bhargava

Aditya Bhargava is a Software Engineer with a dual background in Computer Science and Fine Arts. He blogs on programming at adit.io.

Links

• Aditya’s blog: https://www.adit.io/
• Grokking Algorithms, Second Edition: https://www.manning.com/books/grokking-algorithms-second-edition
• DuckTyped: https://www.ducktyped.org/
• Last Skeet in AWS: https://lastskeetinaws.com/

Sponsor

The Duckbill Group: duckbillgroup.com