Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling

James Cowling is the CTO at Convex and was previously the most senior engineer at Dropbox. We discussed technical details of his past projects, simplicity vs complexity, and career advice given where AI is today.• My ergonomic keyboard project I mentioned, you can follow along here: https://read.compose.llc/𝗣𝗼𝗱𝗰𝗮𝘀𝘁 𝗹𝗶𝗻𝗸𝘀:• YouTube: https://youtu.be/3XkmNSuHFmY• Apple: https://podcasts.apple.com/us/podcast/the-peterman-pod/id1777363835• Transcript: https://www.developing.dev/p/dropboxs-former-most-senior-eng-building𝗧𝗵𝗮𝗻𝗸 𝘆𝗼𝘂 𝘁𝗼 𝘁𝗵𝗶𝘀 𝗲𝗽𝗶𝘀𝗼𝗱𝗲'𝘀 𝘀𝗽𝗼𝗻𝘀𝗼𝗿 𝗳𝗼𝗿 𝘀𝘂𝗽𝗽𝗼𝗿𝘁𝗶𝗻𝗴 𝗺𝘆 𝘄𝗼𝗿𝗸:• WorkOS: makes your app Enterprise Ready with easy to use APIs to add SSO, SCIM, RBAC, and more in just a few lines of code, check them out at https://workos.com/𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:0:00 - Intro0:53 - Systems work during his PhD13:05 - Dropbox technical deep dive21:57 - Why Dropbox migrated from AWS36:40 - How to do massive migrations44:31 - Simplicity vs complexity in promos49:23 - What technical teams should be focused on1:00:25 - Doing the right thing vs promo hypothetical1:08:13 - Why he dipped into management sometimes1:11:36 - Why you shouldn't lead by example1:23:23 - How to mentor Senior Staff+ engineers1:27:30 - Career advice for the AI era1:37:21 - Why he started his own company1:46:05 - The most technically challenging work of his career1:48:10 - How he got involved in Silicon Valley1:52:16 - Career regrets1:55:54 - Top technical book recommendation1:56:36 - Younger self & permanent underclass advice𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝗝𝗮𝗺𝗲𝘀:• LinkedIn: https://www.linkedin.com/in/jcowling/• Twitter/X: https://x.com/jamesacowling• His company: https://www.convex.dev/𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝗥𝘆𝗮𝗻:• Newsletter: https://www.developing.dev/• X/Twitter: https://x.com/ryanlpeterman• LinkedIn: https://www.linkedin.com/in/ryanlpeterman/• Threads: https://www.threads.com/@ryanlpeterman• Instagram: https://www.instagram.com/ryanlpeterman• TikTok: https://www.tiktok.com/@ryanlpeterman𝗥𝗲𝗳𝗲𝗿𝗲𝗻𝗰𝗲𝗱 𝗶𝗻 𝘁𝗵𝗶𝘀 𝗲𝗽𝗶𝘀𝗼𝗱𝗲:• His PhD Thesis: https://www.usenix.org/system/files/conference/atc12/atc12-final118.pdf• Masters paper: https://www.cs.princeton.edu/courses/archive/fall19/cos418/papers/vr-revisited.pdf• Papercuts writing he mentioned: https://medium.com/@jamesacowling/embracing-papercuts-e6390055dfc4• "Don't lead by example": https://medium.com/@jamesacowling/dont-lead-by-example-4f86b1174e64• His writing about orienting teams around missions: https://medium.com/@jamesacowling/your-system-is-not-a-sports-team-e17f9eb16b94