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