The PowerShell Podcast Stop Trying So Hard and Start Automating Smarter with Jake Hildreth

Principal Security Consultant and community favorite Jake Hildreth returns to The PowerShell Podcast to talk about building smarter automation, leveling up through community, and creating tools that solve real problems. Andrew shares his “stop trying so hard” theme for the year, how working smarter applies directly to scripting and security, and why getting involved with others is one of the fastest ways to grow in your career.

The conversation dives into Jake’s recent projects including Deck, a Markdown-to-terminal presentation tool built on Spectre.Console, and Stepper, a resumable scripting framework designed for long-running workflows that can’t be fully automated end-to-end. They also explore presentation skills, avoiding “death by PowerPoint,” and why security work requires constantly re-checking assumptions as threats evolve.

The PowerShell Podcast PSStucco, Accessibility, and the Power of Templating in PowerShell with Gilbert Sanchez & Jake Hildreth

In this high-energy episode, returning guests Gilbert Sanchez and Jake Hildreth join Andrew for a deep dive into:

• Module templating with PSStucco

• Building for accessibility in PowerShell

• Creating open source GitHub orgs like PSInclusive

• How PowerShell can lead to learning modern dev workflows like GitHub Actions and CI/CD

What begins with a conversation about a live demo gone hilariously sideways turns into an insightful exploration of how PowerShell acts as a launchpad into bigger ecosystems like GitHub, YAML, JSON, and continuous integration pipelines.Bios &

The PowerShell Podcast Building Secure PowerShell Solutions with Jake Hildreth

In this episode of the PowerShell Podcast, we welcome back security-focused PowerShell expert Jake Hildreth for an insightful conversation about PowerShell, security tools, and his continued journey in the PowerShell community. Jake shares updates on Locksmith v2, his work with PowerPUG, and his experience learning new PowerShell techniques to refine and improve his tools.

Bio: I’m a husband, a dad, and a recovering sysadmin. I’ve worked in technology since the year 2000, when I got my first tech job as Tier 1 support for cable modem companies. After that, I transitioned into systems & network administration, always with a security focus. In the last three years, I pivoted into security, focusing on Active Directory. When I’m not working, I enjoy cooking, drinking whiskey, lifting weights, traveling, reading… and writing code. Coding is like creating and solving little puzzles for yourself! So soothing.