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/

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/

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

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 From breaking outdated rules to building smarter, safer companies, this conversation reframes what it means to lead with curiosity.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

Deepak Dutt, founder of Zighra, reveals how continuous behavioral authentication is changing the game—from stopping $200M fraud schemes to securing military operations. Deepak: https://www.linkedin.com/in/deepakdutt/ Zighra: https://zighra.com/ Jon: https://www.linkedin.com/in/jon-mclachlan Sasha: https://www.linkedin.com/in/aliaksandr-sinkevich YSecurity: https://www.ysecurity.io

What if your first lines of code determined your startup’s ability to scale? Dirk Meister, founding engineer at Augment Code, walks us through the intentional security architecture decisions they made on day one—and why trust isn't something you can bolt on later.

Dirk Meister: https://www.linkedin.com/in/meisterdirk/

Augment Code: https://www.augmentcode.com/

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

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

YSecurity: https://www.ysecurity.io/

Michael Nov, Co-Founder and CEO of Prime Security, reveals how ignoring the design stage creates costly security gaps later. He shares hard-won lessons from building at OwnBackup and launching a startup during crisis.

Michael: https://www.linkedin.com/in/michael-nov Prime Security: https://www.primesec.ai Jon: https://www.linkedin.com/in/jon-mclachlan Sasha: https://www.linkedin.com/in/aliaksandr-sinkevich YSecurity: https://www.ysecurity.io