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/
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34:47
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34:47
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/
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25:49
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25:49
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
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35:37
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35:37
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
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35:59
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35:59
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
The Security Podcast of Silicon Valley invites founders, engineers, and security leaders to share how they tackle compliance, growth, and real-world security challenges—turning obstacles into strategic advantages. Brought to you by YSecurity.
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