Screaming in the Cloud

• Finding Engineers with Empathy with Lili Rogowsky

  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.vc Email Lili: [email protected] SponsorThe Duckbill Group: duckbillgroup.com

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• Making Dropping and Sharing Easy with Timo Josten

  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 

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  30:31
• “Just in Case” vs. “Just in Time” with Aditya Bhargava

  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 AdityaAbout Aditya BhargavaAditya Bhargava is a Software Engineer with a dual background in Computer Science and Fine Arts. He blogs on programming at adit.io.LinksAditya’s blog: https://www.adit.io/Grokking Algorithms, Second Edition: https://www.manning.com/books/grokking-algorithms-second-editionDuckTyped: https://www.ducktyped.org/Last Skeet in AWS: https://lastskeetinaws.com/SponsorThe Duckbill Group: duckbillgroup.com 

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  32:51
• The Current State of Cloud Security with Crystal Morin

  Sysdig’s 2025 Cloud-Native and Security Usage Report is hot off the presses, and Corey has questions. On this episode, he’s joined by Crystal Morin, a Cybersecurity Strategist at Sysdig, to break down the trends of the past year. They discuss Sysdig’s approach to detecting and responding to security and the success the company has seen with the rollout of Sysdig Sage (an AI product that Corey thinks is actually useful). They also chat about what’s driving a spike in machine identities, practical hygiene in cloud environments, and the crucial importance of automated responses to maintain robust security in the face of increasingly sophisticated cyber threats.Show Highlights(0:00) Intro(0:39) Sysdig sponsor read(2:22) Explaining Sysdig's 5/5/5 Benchmark(4:06) What does Sysdig's work entail?(10:03) Cloud security trends that have changed over the last year(14:30) Sysdig sponsor read(15:16) How Sysdig is using AI in its security products(19:09) How many users are adopting AI tools like Sysdig Sage(25:51) The reality behind the recent spike of machine identities in security(29:24) Handling the scaling of machine identities(35:37) Where you can find Sysdig's 2025 Cloud-Native and Security Usage ReportAbout Crystal MorinCrystal Morin is a Cybersecurity Strategist with more than 10 years of experience in threat analysis and research. Crystal started her career as both a Cryptologic Language Analyst and Intelligence Analyst in the United States Air Force and as a contractor for Booz Allen Hamilton, where she helped develop and evolve their cyber threat intelligence community and threat-hunting capabilities. In 2022, Crystal joined Sysdig as a Threat Research Engineer on the Sysdig Threat Research Team, where she worked to discover and analyze cyber threat actors taking advantage of the cloud. Today, Crystal bridges the gap between business and security through cloud-focused content for leaders and practitioners alike. Crystal’s thought leadership has been foundational for pieces such as the “2024 Cloud-Native Security and Usage Report” and “Cloud vs. On-Premises: Unraveling the Mystery of the Dwell Time Disparity,” among others.LinksSysdig’s 2025 Cloud-Native and Security Usage Report: https://sysdig.com/2025-cloud-native-security-and-usage-report/Sysdig on LinkedIn: https://www.linkedin.com/company/sysdig/Crystal’s LinkedIn: https://www.linkedin.com/in/crystal-morin/SponsorSysdig: https://sysdig.com/

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  36:46
• The Difference Between Marketing and BS with Jonathan Cowperthwait

  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: [email protected] Corey: [email protected] Duckbill Group: duckbillgroup.com 

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