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