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