First Topic - Podcast Content Plans for 2026
Every year, I like to sit down and consider what the podcast should be focusing on. Not doing so ensures every single episode will be about AI and nobody wants that. Least of all, me. If I have one more all-AI episode, my head is going to explode.
With that said, most of what we talk about in this segment is AI (picard face palm.png). I think 2026 will be THE defining year for GenAI. Three years after the release of ChatGPT, I think we've hit peak GenAI hype and folks are ready for it to put up or shut up. We'll see winners grow and get acquired and losers pivot to something else. More than anything, I want to interview folks who have actually seen it work at scale, rather than just in a cool demo in a vendor sandbox.
Also on the agenda for this year:
- The battle against infostealers and session hijacking: we didn't have a good answer in 2025. When is it coming? Will it include Macs, despite them not having a traditional TPM?
- The state of trust in outsourcing and third party use (Cloud, MSSPs, SaaS, contractors): 2025 was not a good year for third parties. Lots of them got breached and caused their customers a lot of pain. Also, there's the state of balkanization between the US and... the rest of the entire world. Everyone outside the US seems to be trying to derisk their companies and systems from the Cloud Act right now.
- Vulnerability management market disruption: there are half a dozen startups already plotting to disrupt the market, likely to come out of stealth in 2026
- Future of the SOC: if it's not AI, what is it?
- What else???
What am I missing? What would you like to see us discuss? Please drop me a line and let me know: [email protected]
Topic 2: The state of cybersecurity hiring
This topic has been in the works for a while! Ayman had a whole podcast and book focused on all the paths people take to get into security. Jackie worked with WiSys on outlining pathways into a cybersecurity career.
Whether you're already in cyber or looking for a way in, this segment crams a lot of great advice into just 15-20 minutes.
Segment resources:
- Ayman's personal guide for getting into security
- https://www.wicys.org/wp-content/uploads/2025/10/WiCyS-Pathways-in-Cyber-PDF-9.24.25.pdf
News
Finally, in the enterprise security news,
- Fundings and acquisitions still strong in 2026!
- Santa might be done delivering gifts, but not protecting Macs!
- ClickFix attacks
- Weaponized Raspberry Pis
- MongoDB incidents for Christmas
- Top 10 Cyber attacks of 2025
- US gets tough on nation state hackers?
- Brute force attacks on Banks
- An AI Vending Machine
All that and more, on this episode of Enterprise Security Weekly.
Security Weekly listeners save $100 on their RSAC 2026 All Access Pass! RSAC 2026 Conference will take place March 23rd to March 26th in San Francisco. To register using our discount code, please visit securityweekly.com/rsac26 and use the code 56U5SECWEEKLY! We hope to see you there!
Adrian Sanabria
- FUNDING and M&A, courtesy of the Security, Funded newsletter, issue #225 – New Year, Same Money Printer
Vibe Check
Q: What cybersecurity trend peaks in 2026? A: AI agent hype cycle (top answer by a mile)
Other answers:
- Exposure management replacing vulnerability management
- GenAI governance platforms
- Platform consolidation
Funding
- Cyera, a United States-based data security posture management platform, raised $400.0M in Private Equity from Blackstone Group.
- Vega, an Israel-based security operations and automation platform, raised a $120.0M Series B from Accel.
- Exein, an Italy-based firmware and Internet of Things (IoT) security platform, raised $117.7M Venture Round from Blue Cloud Ventures and undisclosed Debt Financing from JP Morgan.
- Adaptive Security, a United States-based security awareness training platform for AI-enabled social engineering and deepfake attacks, raised a $81.0M Series B from Bain Capital Ventures.
- Act Security, an Israel-based identity governance for AI agents and applications, raised a $40.0M Series A from Notable Capital.
- Echo, an Israel-based secure container image infrastructure platform, raised a $35.0M Series A from N47.
- Armadin Security, a United States-based automated red-teaming and AI threat hunting platform, raised a $24.0M Seed from Ballistic Ventures.
- Dux Security, a United States-based threat and risk prioritization platform based on exploitability analysis, raised a $9.0M Seed from Maple Capital, Redpoint, and TLV Partners.
Acquisitions
- Armis, a United States-based agentless IoT security platform, was acquired by ServiceNow for $7.8B. Armis had previously raised $1.2B in funding.
- FREE TOOLS: GitHub – 0x4D31/santamon: Lightweight macOS detection agent built on Santa’s Endpoint Security telemetry.
- DETECTION ENGINEERING: What are Composite Detections?
- TRENDS: The Industrialization of “ClickFix”: Inside ErrTraffic
- BREACHES: Raspberry Pi used in attempt to take over ferry
"A Raspberry Pi wakeup call: Why enterprises must rethink physical security"
- BREACHES: Top 10 Cyber-Attacks of 2025
- VULNERABILITIES: Merry Christmas Day! Have a MongoDB security incident.
What timing, sheesh. Has impacted at least a handful of very large companies.
- CYBERCRIME: Money Laundering and Sanction Fines Fall 61% Amid US Deregulation
- CYBERWAR: Washington Wants to Get Tough on Nation-State Hackers. Are Infrastructure Operators Ready?
- STORYTELLING: Matt Blaze vs Master-keyed locks
Probably unsurprising for those of us that have been around for a while and have seen companies and industries react angrily when their security flaws are publicly exposed.
- SQUIRREL: Thieves use large drill to break into bank vault, steal over $35 million
This takes B&E to the extreme!
Ayman Elsawah
Sean Metcalf
- TRENDS: We Put an AI Vending Machine in Our Office. It Gave Away Everything.
ADRIAN'S NOTES: WSJ, particularly Joanna Stern, is just hitting it out of the park with consumer testing and advice. While this was a fun and somewhat goofy experiment, it highlights how far AI is away from being functionally autonomous, even for tasks that seem simple.
Alignment was a key issue in this case, though understanding context, memory, and sycophancy were also issues. Issues that all agentic experiments are running into, including cybersecurity.
Salesforce went from enough confidence in LLMs a year ago to lay off 4,000 employees. Now, they're pivoting away from it for automation use cases.
For WSJ subscribers, the written version of this story is here.