Screaming in the Cloud

Wayne Segar, Director of Global Field CTOs at Dynatrace, dives into the complexities of monitoring unpredictable AI workloads. He discusses the breakdown of traditional observability practices when applied to non-deterministic AI systems. The conversation highlights the importance of ‘human in the loop’ approaches and how AI Centers of Excellence help navigate compliance challenges. Wayne also touches on the benefits of consolidating observability tools and the innovative drive of startups compared to larger enterprises.

Join AWS experts Matt Berk and Bowen Wang as they share their insights on the challenges of presenting at major tech events like re:Invent. Matt, a Principal Technical Account Manager passionate about storytelling, and Bowen, a Principal Product Marketing Manager focused on cloud financial management, delve into using customer feedback for product development. They recount hilarious behind-the-scenes moments, like a tsunami warning before their talk, and discuss the importance of engaging storytelling and preparing effectively to connect with audiences.

Ido Neeman, CEO and co-founder of Firefly, is on a mission to tame cloud chaos with Infrastructure as Code. He shares insights from the State of IaC 2025 report, revealing that while IaC adoption is high, many organizations are still tethered to legacy systems. Ido discusses the rise of open-source projects like Open Tofu and highlights the importance of disaster recovery as code. The conversation delves into the challenges of managing multi-cloud environments and underscores the necessity for robust cloud governance amidst evolving tech complexities.

Malith Rajapakse, a DevOps engineer known for his innovative visualizations, discusses simplifying the complexities of AWS's Managed NAT Gateway. He shares the inspiration behind his acclaimed blog post, highlighting the importance of clarity in technical writing. Malith dives into his transition from front-end development to DevOps, revealing challenges with AWS documentation and the motivation to create engaging content. Their conversation also emphasizes the need for more user-friendly resources in the tech world, making complex subjects accessible to all.

Ann Johnson, Corporate Vice President and Deputy CISO at Microsoft, discusses her 40-year journey in cybersecurity. She emphasizes the importance of honest communication in leadership and the need to foster a collaborative security culture within Microsoft. The conversation touches on the complexities of technology, the role of AI, and its impact on creativity. Ann also highlights her commitment to STEM scholarships and the significance of blending humanities with technology to preserve artistry in an AI-driven world.

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 VenturesAbout Lili RogowskyLili 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.LinksAtypical Ventures: atypical.com Email Lili: lili@atypical.vc SponsorThe 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 DropshareAbout Timo JostenTimo Josten is the developer of Dropshare, the macOS and iOS app to upload anything anywhere.LinksTimo’s LinkedIn profile: https://www.linkedin.com/in/timo-josten-493962185/Timo’s personal website: https://josten.ioDropshare: https://dropshare.app/shitposting.pictures SponsorThe Duckbill Group: duckbillgroup.com 

Aditya Bhargava, a Staff Software Engineer at Etsy and author of Grokking Algorithms, shares his insights on effective learning methods. He contrasts 'just in case' vs. 'just in time' approaches, emphasizing that necessity drives better comprehension. Aditya discusses how concise, engaging resources can clarify complex subjects like AWS networking. He advocates for brevity in educational materials, highlighting frustrations with lengthy books. His unique blend of art and tech enhances his teaching, making algorithms accessible and fun!

Crystal Morin, a Cybersecurity Strategist at Sysdig with over 10 years in threat analysis, joins to explore the latest cloud security trends. They dive into the impact of AI-driven tools like Sysdig Sage and discuss the critical need for automated responses to cyber threats. The conversation also highlights the surge in machine identities and the challenges they present for cloud security management. Crystal emphasizes the necessity of quick detection and response in maintaining robust security amid evolving threats.

What’s the difference between marketing and BS? On this episode, Corey Quinn is joined by Jonathan Cowperthwait, Duckbill’s brand-new Head of Marketing. Jonathan's career path is a bit unconventional. After all, not everyone can say their professional journey was influenced by The West Wing. Even though he’s a marketer by trade, Jonathan still has the technical know-how needed to work in the often expensive world of cloud economics. Have you ever wanted to know what The Duckbill Group’s relationship with AWS is really like? How fun is it to sit on domains like “oldmanstartup?” Is there a similarity between clouds and butts? This interview is the inside scoop on The Duckbill Group that you never knew you needed. Show Highlights(0:00) Intro(1:11) Duckbill Group sponsor read(1:45) Acquiring the Duckbill Group office post-pandemic(2:52) Keeping your pants on during a pandemic so you can officiate your nanny's wedding(6:07) Jonathan's background prior to joining The Duckbill Group(11:29) What Duckbill was looking for when they hired Jonathan(14:54) When marketing begins to feel like spam(15:40) The fun of having disposable domains and email addresses(18:20) The importance of a good name for a product(19:38) Duckbill Group sponsor read(20:07) The Duckbill Group isn't just Corey Quinn(21:03) The "Cloud to Butt" extension(24:01) Corey's beef with Google's AI search engine(24:57) What can people expect from the Duckbill Group's new marketing effort(30:58) Where you can find more from JonathanAbout Jonathan CowperthwaitJonathan Cowperthwait does positioning, messaging, and go-to-market strategy to maximize awareness and revenue for technology brands of all sizes.He prides himself on being a slow runner, fast talker, and good writer.LinksJonathan on LinkedIn: https://www.linkedin.com/in/cowperthwait/Jonathan on Bluesky: https://web-cdn.bsky.app/profile/cowp.coEmail Jonathan: offmylawn@oldmanstartup.comEmail Corey: corey@shitposting.monsterSponsorThe Duckbill Group: duckbillgroup.com