The Security Podcast of Silicon Valley

88. How Illumio Stops Hackers When the “Front Door” Fails (with Andrew Rubin)

The perimeter will fail. What matters is whether your business turns one incident into a disaster. Andrew Rubin, Founder and CEO of Illumio, explains how breach containment reduces blast radius, why category timing is “luck,” and what leaders must do as AI speeds up attackers and defenders. Listen for a founder-level playbook on building security that scales with growth.

Andrew: https://www.linkedin.com/in/andrewsrubin

Illumio: https://www.illumio.com

Jon: https://www.linkedin.com/in/jon-mclachlan

Sasha: https://www.linkedin.com/in/aliaksandr-sinkevich

YSecurity: https://www.ysecurity.io

87. Escape the Ticket Trap: How AI Agents Are Replacing Manual DevOps

AI won’t save your startup. Unless it can ship changes safely. Venkat Thiruvengadam breaks down why the real value isn’t the model, it’s the orchestration: guardrails, permissions, context, and human-in-the-loop workflows that let agents do more than “read-only.” Tune in for a practical conversation on scaling DevOps, security, and compliance without slowing the business.

Venkat: www.linkedin.com/in/venkat-thiruvengadam 

DuploCloud: www.duplocloud.com 

Jon: www.linkedin.com/in/jon-mclachlan 

Sasha: www.linkedin.com/in/aliaksandr-sinkevich 

YSecurity: www.ysecurity.io

86. Ex-FBI Agent: The Biggest Security Threat is the Human Behind the Keyboard

Trevor Hilligoss, Head of Security Research at SpyCloud  and former FBI agent, joins the show to discuss why humans remain the biggest security risk facing organizations today. From reused credentials to commoditized cybercrime tools, Trevor breaks down how attackers actually gain access — and why focusing on real-world human behavior is more effective than worrying about sophisticated nation-state threats.

Trevor: www.linkedin.com/in/thilligoss/

SpyCloud: spycloud.com

Jon: www.linkedin.com/in/jon-mclachlan

Sasha: www.linkedin.com/in/aliaksandr-sinkevich

YSecurity: www.ysecurity.io

85. How Companies Lose $197 Million in Seconds (with Channi Greenwall, Olympix)

What if 90% of “secured” smart contracts were still exploitable? That’s the reality Olympix founder and CEO Channi Greenwall is seeing on-chain today. She breaks down why traditional audits are failing Web3 teams, why the attack surface is bigger than most founders realize, and how automated security is starting to close the gap.

You’ll learn:

• Why Web3 security is closer to medical devices and aviation than typical SaaS risk
• How one exploit can wipe out years of startup effort in seconds
• The hidden overlap between Web2 and Web3 attack surfaces that founders underestimate
• What it actually looks like to automate 60–80% of what human auditors do today

Listen to the full episode on your favorite platform.

Channi: www.linkedin.com/in/channi-greenwall
Olympix: www.olympix.security/
Jon: www.linkedin.com/in/jon-mclachlan
Sasha: www.linkedin.com/in/aliaksandr-sinkevich
YSecurity: www.ysecurity.io

84. What gets missed when nobody reviews the code (with Jack Cable, Corridor)

Code ships faster than anyone can review it. Jack Cable, CEO and Co-Founder of Corridor, explains what actually gets missed when teams stop reviewing every pull request, why most security tools surface noise instead of risk, and how Corridor approaches secure-by-design when speed is non-negotiable.
Jack: https://www.linkedin.com/in/jackcable
Corridor: https://www.corridor.dev
Jon: https://www.linkedin.com/in/jon-mclachlan
Sasha: https://www.linkedin.com/in/aliaksandr-sinkevich
YSecurity: https://www.ysecurity.io

83. How small companies can make their security doable (with Phil Howie)

What if your first security hire wasn’t a person, but a simple, guided program that made sense to everyone in your company? In this conversation, Sidekick founder and CEO Phil Howie breaks down how SMBs can build a security and privacy practice from the ground up—long before they can afford a full internal team. We cover the reality of compliance vs real security, working with MSPs, the role of design in security tools, and how founders should think about AI, governance, and future regulation. If you’re a founder trying to grow in regulated markets, this one’s for you.

Phil: https://www.linkedin.com/in/philhowie

Sidekick: https://www.sidekick.co

Jon: https://www.linkedin.com/in/jon-mclachlan/ 

Sasha: https://www.linkedin.com/in/aliaksandr-sinkevich/ 

YSecurity: https://www.ysecurity.io/ 

82. Automating app security for modern dev teams (with Rejah Rehim)

Most companies still test security long after code is shipped. That delay creates blind spots.

In this episode, Rejah Rehim, Co-Founder & CEO of Beagle Security, explains how automated penetration testing gives teams a clearer picture of their real exposure—while keeping the process simple enough for developers to run themselves.

 

Rejah: https://www.linkedin.com/in/rejah/

Beagle Security: https://beaglesecurity.com/

Jon: https://www.linkedin.com/in/jon-mclachlan/ 

Sasha: https://www.linkedin.com/in/aliaksandr-sinkevich/ 

YSecurity: https://www.ysecurity.io/ 

How to put AI agents safely into production (with Eric Olden)

AI agents can burn through budgets and trust in minutes. Eric Olden, Co-Founder and CEO of Strata Identity, breaks down the control plane founders need: policy-driven guardrails, intent/context/outcome audit, and lifecycle governance—so you can move from sandbox to production with confidence.

Eric: https://www.linkedin.com/in/boughtnotsold

Strata Identity: https://www.strata.io

Jon: https://www.linkedin.com/in/jon-mclachlan

Sasha: https://www.linkedin.com/in/aliaksandr-sinkevich

YSecurity: https://www.ysecurity.io

Think Like a Hacker: Why Curiosity Drives Innovation and Security (with Ted Harrington)

Most people think hackers exploit systems. The best hackers improve them. In this episode, Ted Harrington explains how to unlock your “inner hacker”—the mindset that turns obstacles into innovation. From breaking outdated rules to building smarter, safer companies, this conversation reframes what it means to lead with curiosity.

Ted: https://www.linkedin.com/in/securityted/ 
Ted’s website: https://www.tedharrington.com/ 
Jon: https://www.linkedin.com/in/jon-mclachlan
Sasha: https://www.linkedin.com/in/aliaksandr-sinkevich
YSecurity: https://www.ysecurity.io

AI at Brinks Home: Lower costs, better customer support (with Veronica Moturi)

Cutting support costs usually tanks experience—unless you redesign the system. Veronica Moturi shares how Brinks built an AI “first line,” kept humans for nuance, and improved accuracy by unifying data, verification, and troubleshooting. If you’re scaling support, this is your roadmap to trust, speed, and measurable unit economics.

 

Veronica: www.linkedin.com/in/veronica-moturi

Brinks Home: brinkshome.com

Jon: www.linkedin.com/in/jon-mclachlan 


Sasha: www.linkedin.com/in/aliaksandr-sinkevich 

YSecurity: www.ysecurity.io