In this episode, Chuck, Ayush, and Valentino join Olly Headey as he shares his expansive career journey, from co-founding FreeAgent to navigating the intricate world of cloud migration and technology adoption. They dive deeply into the various challenges and decisions involved in choosing frameworks like React, tackling server costs with CDN solutions, and simplifying complex tech stacks. Olly also discusses his experiences with boot camps, emphasizing the importance of foundational knowledge over trendy frameworks. They touch on the significance of dependencies in tech projects, the evolving landscape of Ruby usage beyond Rails, and the practicalities of AWS CloudFront integrations. Olly offers his unique insights into balancing established and new technologies, emphasizing a pragmatic approach to tech evolution. Join them as they explore the nuances of engineering management, the real-world implications of tech choices, and the strategies for maintaining simplicity in a fast-evolving tech landscape. Let’s get started! Socials LinkedIn: Olly Headey Picks Charles - Challengers! | Board GameCharles - The Book on Mental ToughnessOlly - Friendly.rb - Your friendy European Ruby conferenceValentino - PodcastBuddy  Become a supporter of this podcast: https://www.spreaker.com/podcast/ruby-rogues--6102073/support.