This week, Robbie and Chuck talk about the unintended chaos of “move fast and break things” in both software and startups. From Riverside glitches to Tesla’s overengineered wipers, they explore how updates can derail otherwise stable experiences. They unpack the economics of getting laid off, the pressure to build a personal brand in tech, and the strange fate of dev tools. Plus, Robbie shares his latest app ideas.

In this episode:

• (00:00 ) - Intro
• (02:27 ) - Whiskey rating and review: Old Grand-Dad 16 Year Straight Bourbon Whiskey
• (13:27 ) - When updates break what worked
• (20:21 ) - Are devs prioritizing personal brands?
• (23:13 ) - The strange economics of getting laid off
• (28:39 ) - Is GitLab trash?
• (30:25 ) - Robbie’s ADHD app and vibe coding plans
• (34:05 ) - Debt, 401k, and emergency funds
• (35:30 ) - Prepping for Big Sky Dev Con
• (38:26 ) - UPS shipping woes
• (44:10 ) - React Miami and difficulties taking a podcast on the road
• (48:58 ) - Whiskey + Girl Scout cookies (and other pairings)
• (54:05 ) - Should open source have a franchise model?
• (55:28 ) - Work, paternity leave, and the IBM acquisition
• (57:15 ) - Tesla shopping for a family of five
• (61:08 ) - Movies and TV

Links

• Old Grand-Dad: https://www.beamdistilling.com/our-brands/old-grand-dad-bourbon
• Wild Turkey: https://www.wildturkeybourbon.com/
• Riverside: https://riverside.fm/
• Tesla: https://www.tesla.com/
• Arc: https://arc.net/
• Silicon Valley: https://en.wikipedia.org/wiki/Silicon_Valley_(TV_series)
• Chrome: https://www.google.com/chrome/
• Shark Tank: https://en.wikipedia.org/wiki/Shark_Tank
• GitHub: https://github.com
• Microsoft: https://www.microsoft.com/
• Typescript: https://www.typescriptlang.org/
• Rust: https://www.rust-lang.org/
• VS Code: https://code.visualstudio.com/
• OpenAI: https://openai.com
• Cursor: https://www.cursor.com/
• Windsurf: https://windsurf.ai/
• Copilot: https://github.com/features/copilot
• Deno: https://deno.com/
• Node: https://nodejs.org/
• GitLab: https://gitlab.com/
• Bitbucket: https://bitbucket.org/
• Fresca: https://www.coca-cola.com/us/en/brands/fresca-sparkling-soda
• Shepherd: https://www.shepherdjs.dev/
• ChatGPT: https://chatgpt.com/
• Claude: https://claude.ai
• Warp: https://www.warp.dev/
• Big Sky Dev Con: https://bigskydevcon.com/
• Adam Argyle: https://x.com/argyleink/
• HTMX: https://htmx.org/
• Carson Gross: https://x.com/htmx_org/
• Ruby: https://www.ruby-lang.org/
• UPS: https://www.ups.com
• Amazon: https://amazon.com
• React Miami: https://www.reactmiami.com/
• Typecraft: https://typecraft.dev/
• Jason Lengstorf: https://x.com/jlengstorf
• Web Dev Challenge: https://www.youtube.com/playlist?list=PLz8Iz-Fnk_eTkZvSNWXW_TKZ2UwVirT2M
• Mux: https://www.mux.com/
• Aaron Francis: https://x.com/aarondfrancis
• Terminal Coffee: https://www.terminal.shop/
• Syntax: https://syntax.fm
• Sentry: https://Sentry.io/
• David Cramer: https://x.com/zeeg
• Girl Scouts: https://www.girlscouts.org/
• Carlyle House: https://en.wikipedia.org/wiki/Carlyle_House
• Ken Wheeler: https://x.com/ken_wheeler/
• Whiskey Library: https://mwlpdx.com/
• Jack Rose: https://www.jackrosediningsaloon.com/
• Gumroad: https://gumroad.com
• Supabase: https://supabase.com/
• McDonald's: https://www.mcdonalds.com/
• HashiCorp: https://www.hashicorp.com/
• IBM: https://www.ibm.com/
• Model X: https://www.tesla.com/modelx
• Elon Musk: https://x.com/elonmusk
• Rivian: https://rivian.com/
• Why Women Kill: https://en.wikipedia.org/wiki/Why_Women_Kill
• Lucy Liu: https://en.wikipedia.org/wiki/Lucy_Liu
• American Psycho: https://en.wikipedia.org/wiki/American_Psycho_(film)
• Paramount Plus: https://www.paramountplus.com/
• Yellowstone: https://en.wikipedia.org/wiki/Yellowstone_(American_TV_series)
• 1883: https://en.wikipedia.org/wiki/1883_(TV_series)
• Faith Hill: https://en.wikipedia.org/wiki/Faith_Hill
• Tim McGraw: https://en.wikipedia.org/wiki/Tim_McGraw
• Game of Thrones: <a href="https://www.hbo.com/game-of-thrones" rel="