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Azure DevOps Podcast

Message from Jeffrey Palermo: Howdy.  Welcome to my podcast.  I hope it helps you ship software more quickly and more reliably. Through the topics and guests, I hope your life is made easier. Let me know what topics would be helpful for you.

Podcast sponsor: Clear Measure We are a software architecture company that empowers our client's development teams to be self-sufficient: moving fast, delivering quality, and running their systems with confidence.

Aug 30, 2021

This week, Rob Reynolds, the founder and CEO of Chocolatey Software, is joining the podcast!


Rob is a developer-turned-founder who has been involved with several highly successful open source projects related to automation in the Windows ecosystem. He has over 10 years of experience in infrastructure automation, modern automation approaches, and agile methodologies. Most of all, Rob strives for simplicity and automation with low-maintenance solutions that solve customer needs.


In this episode, Rob is speaking all about Chocolatey Software, his solution for a universal package manager for Windows. Chocolatey makes complex tasks simple by easily handling all aspects of package management within the Windows software management ecosystem and works with all existing software installation technologies like MSI, NSIS, InnoSetup, etc. Chocolatey also integrates with all existing infrastructure management and RMM tools and is trusted by hundreds of organizations to manage software across their servers and desktops.


Rob shares about the current benefits of using Chocolatey, the origin story of Chocolatey, the next version of the software, his experience moving from Chief Architect to CEO, tips and advice for leadership growth and development, and much more!


Topics of Discussion:

[:14] About The Azure DevOps Podcast, Clear Measure, and Jeffrey’s offer to speak at virtual user groups.

[1:22] Jeffrey is looking to hire an apprentice! If you, or anyone you know, loves to code and wants to pursue software engineering, apply today!

[2:09] Be sure to check out the new video podcast, Architect Tips.

[2:17] About today’s episode with  Rob Reynolds.

[2:27] Jeffrey welcomes Rob to the podcast.

[4:09] An overview of Chocolatey: what it does, its origin story, and why you may want to give it a try!

[8:02] How many community packages are in the Chocolatey catalog?

[10:25] Rob shares some examples of how people are using Chocolatey packages and offshoot projects that have branched off of Chocolatey.

[13:53] All about the system admin side of Chocolatey and why system admins might want to check it out!

[21:45] A word from The Azure DevOps Podcast’s sponsor: Clear Measure.

[22:15] How Chocolatey makes everything easier.

[24:27] Why was the old-style Runbook process originally put into place? How and why have things become automated since?

[27:45] About RoundhousE, the professional database chance and versioning management tool that Rob authored.

[31:45] What led Rob to make the shift from Chief Architect to CEO? What was the experience like?

[39:40] The current open job positions that are available at Chocolatey.

[40:48] Rob reflects on his career journey and growth from Chief Architect to CEO.

[41:09] About one of Chocolatey’s core values (growth) and Rob’s recommendations for personal and professional growth.

[43:02] What’s coming in the next version of Chocolatey!

[48:40] Jeffrey thanks Rob for joining the podcast.


Mentioned in this Episode:

Architect Tips — New video podcast!

Azure DevOps

Clear Measure (Sponsor)

.NET DevOps for Azure: A Developer's Guide to DevOps Architecture the Right Way, by Jeffrey Palermo — Available on Amazon! — Click here to download the .NET DevOps for Azure ebook!

Jeffrey Palermo’s Youtube

Jeffrey Palermo’s Twitter Follow to stay informed about future events!

Chocolatey Software


Windows Remix

Azure Pipelines





The Chuck Norris Framework (Uppercut, Dropkick, etc.)

Ruby | Puppet


The Craig Groeschel Leadership Podcast

The Andy Stanley Leadership Podcast


Want to Learn More?

Visit AzureDevOps.Show for show notes and additional episodes.