The heart of this talk is about making it easier for new developers to get started with Plone. For more than 3 years David has been conducting ad-hoc experiments related to developer onboarding. During that period he explored ideas such as Plone Drills, a Diazo Snippets Library and Chrome Plugin, cloud based installations of Plone development environments, and a Plone Newbie Developer Toolkit (Plone 4 only); he contributed to Alex Clark's Plock Plone Installer project; and he spent a lot of time on a theming approach for Plone which "extends" Diazo called Gloss. He also created a short video series related to using Gloss with Webflow. This talk aims to share David's explorations and perhaps make some recommendations on a way forward for improving the developer onboarding experience.