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: https://www.hbo.com/game-of-thrones

Connect with Chuck and Robbie

Robbie Wagner: https://x.com/RobbieTheWagner
Chuck Carpenter: https://x.com/CharlesWthe3rd

Subscribe and stay in touch

Website: https://whiskey.fm
Apple Podcasts: https://podcasts.apple.com/us/podcast/whiskey-web-and-whatnot/id1552776603
Spotify: https://open.spotify.com/show/19jiuHAqzeKnkleQUpZxDf
Overcast: https://overcast.fm/itunes1552776603
YouTube: https://www.youtube.com/@WhiskeyWebAndWhatnot

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