{"version":"https://jsonfeed.org/version/1","title":"The Friday Deploy","home_page_url":"https://thefridaydeploy.fireside.fm","feed_url":"https://thefridaydeploy.fireside.fm/json","description":"The Friday Deploy is a podcast about shipping software with confidence. Today, John and Garrett run Flipper Cloud and Fireside. Before that, Garrett built and sold Sifter, and John worked in the dark corners of GitHub. Between them, they’ve spent decades building, shipping, breaking, and fixing software. Each episode digs into feature flags, deployments, infrastructure, incidents, product decisions, and the practices that let you deploy anytime and still sleep through the night.","_fireside":{"subtitle":"Ship on Friday. Sleep through the night.","pubdate":"2026-11-06T10:30:00.000-05:00","explicit":false,"owner":"John Nunemaker","image":"https://cdn.fireside.fm/file/fireside-images-2024/podcasts/images/c/cf46278b-b0e2-4c19-bb2d-a4220cbf6aab/cover.jpg?v=2"},"items":[{"id":"2a9b943f-4aef-460f-8fa9-633838d64e27","title":"Episode 2: Your PR Shouldn’t Make Your Stomach Hurt","url":"https://thefridaydeploy.fireside.fm/2","content_text":"AI will happily help you turn a small change into a 3,000-line pull request. Then it'll help you review it forever. At some point, you have to know when to stop.\n\nJohn and Garrett compare the workflows they've built around Nunebot and Workbench: deterministic checks, a second model looking for holes, a limit on review cycles, and pull requests that explain why a change matters and prove it works.\n\nThey also get into moving Fireside's file storage to Cloudflare R2 behind separate read and write flags, watching successful uploads instead of waiting for support emails, and throwing away an overgrown implementation to find a simpler one.\n\nAlong the way: personalized interfaces, the limits of read-only access to your email, AI-assisted appliance repair, and Garrett's basketball app. The point isn't to stop caring about software. It's to spend more time on the parts you actually like, with enough evidence to feel good about shipping.Links:Don’t Make a Human Do What AI Is Amazing At\n — John’s write-up of Nunebot: small PRs, bounded review loops, and proof that changes work.\nReviewer\n — Garrett’s tool for running automated code review checks.\nFlipper Cloud\n — Feature flags for gradual releases and safer deployments.\nFireside\n — The podcast hosting platform behind the storage migration discussed in this episode.\nHoneybadger\n — Error monitoring used to find problems and watch deployments.\nFlare\n — Performance monitoring for Ruby and Rails applications.\nEpisode 1: Changing the Wheels While the Car Is Moving\n — Rebuilding Fireside while keeping it running, verifying dangerous changes, and knowing what complexity is worth adding.\n","content_html":"\u003cp\u003eAI will happily help you turn a small change into a 3,000-line pull request. Then it'll help you review it forever. At some point, you have to know when to stop.\u003c/p\u003e\n\n\u003cp\u003eJohn and Garrett compare the workflows they've built around Nunebot and Workbench: deterministic checks, a second model looking for holes, a limit on review cycles, and pull requests that explain why a change matters and prove it works.\u003c/p\u003e\n\n\u003cp\u003eThey also get into moving Fireside's file storage to Cloudflare R2 behind separate read and write flags, watching successful uploads instead of waiting for support emails, and throwing away an overgrown implementation to find a simpler one.\u003c/p\u003e\n\n\u003cp\u003eAlong the way: personalized interfaces, the limits of read-only access to your email, AI-assisted appliance repair, and Garrett's basketball app. The point isn't to stop caring about software. It's to spend more time on the parts you actually like, with enough evidence to feel good about shipping.\u003c/p\u003e\u003cp\u003eLinks:\u003c/p\u003e\u003cul\u003e\u003cli\u003e\u003ca title=\"Don’t Make a Human Do What AI Is Amazing At\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkyMjkz\"\u003eDon’t Make a Human Do What AI Is Amazing At\n\u003c/a\u003e \u0026mdash; John’s write-up of Nunebot: small PRs, bounded review loops, and proof that changes work.\n\u003c/li\u003e\u003cli\u003e\u003ca title=\"Reviewer\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkyMjk0\"\u003eReviewer\n\u003c/a\u003e \u0026mdash; Garrett’s tool for running automated code review checks.\n\u003c/li\u003e\u003cli\u003e\u003ca title=\"Flipper Cloud\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkyMjk1\"\u003eFlipper Cloud\n\u003c/a\u003e \u0026mdash; Feature flags for gradual releases and safer deployments.\n\u003c/li\u003e\u003cli\u003e\u003ca title=\"Fireside\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkyMjk2\"\u003eFireside\n\u003c/a\u003e \u0026mdash; The podcast hosting platform behind the storage migration discussed in this episode.\n\u003c/li\u003e\u003cli\u003e\u003ca title=\"Honeybadger\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkyMjk3\"\u003eHoneybadger\n\u003c/a\u003e \u0026mdash; Error monitoring used to find problems and watch deployments.\n\u003c/li\u003e\u003cli\u003e\u003ca title=\"Flare\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkyMjk4\"\u003eFlare\n\u003c/a\u003e \u0026mdash; Performance monitoring for Ruby and Rails applications.\n\u003c/li\u003e\u003cli\u003e\u003ca title=\"Episode 1: Changing the Wheels While the Car Is Moving\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkyMjk5\"\u003eEpisode 1: Changing the Wheels While the Car Is Moving\n\u003c/a\u003e \u0026mdash; Rebuilding Fireside while keeping it running, verifying dangerous changes, and knowing what complexity is worth adding.\n\u003c/li\u003e\u003c/ul\u003e","summary":"If a pull request makes your stomach hurt, another round of AI review might not be the answer. John and Garrett compare the workflows that keep changes small, explain how feature flags helped move Fireside's file storage, and talk about what to watch when support gets suspiciously quiet.","date_published":"2026-11-06T10:30:00.000-05:00","attachments":[{"url":"https://aphid.fireside.fm/d/1437767933/cf46278b-b0e2-4c19-bb2d-a4220cbf6aab/2a9b943f-4aef-460f-8fa9-633838d64e27.mp3","mime_type":"audio/mpeg","size_in_bytes":84927702,"duration_in_seconds":3489}]},{"id":"e0839f74-3d30-43d4-b914-6d1492c48ead","title":"Episode 1: Changing the Wheels While the Car Is Moving","url":"https://thefridaydeploy.fireside.fm/1","content_text":"When John, Garrett and Kris bought Fireside, they inherited an eight-year-old Rails app running on Ruby 2.7, Rails 5, Postgres 9.5, and aging infrastructure that could not simply be switched off and rebuilt.\n\nTwo years later, almost every piece has been replaced while podcasts, feeds, and downloads kept running.\n\nIn the first episode of The Friday Deploy, they break down how they rebuilt Fireside while it was live, including a jump from Postgres 9.5 to 18 with no downtime for listeners. They talk about reverse-engineering undocumented infrastructure, using Flipper to put the application into read-only mode, testing migrations until they became boring, and letting agents carry work all the way to the final approval.\n\nThis is not a story about giving an AI agent one prompt and letting it loose on production. It is about breaking dangerous work into small, verifiable steps and knowing where experience and taste still matter.\n\nThey also get into:\n\n\n  Why verification matters more than another round of prompting\n  How multiple models can provide independent reviews\n  Giving agents safe, read-only access to production context\n  Keeping deterministic work out of nondeterministic agents\n  Using real customer data to guide product and interface decisions\n  Scheduled tasks as the beating heart of an AI-assisted workflow\n  Whether the next generation of software needs a traditional interface at all\n\n\nThe goal is not to eliminate risk. It is to gather enough evidence that shipping stops feeling like a leap of faith.Links:Fireside\nFlipper\nFlare\n","content_html":"\u003cp\u003eWhen John, Garrett and Kris bought Fireside, they inherited an eight-year-old Rails app running on Ruby 2.7, Rails 5, Postgres 9.5, and aging infrastructure that could not simply be switched off and rebuilt.\u003c/p\u003e\n\n\u003cp\u003eTwo years later, almost every piece has been replaced while podcasts, feeds, and downloads kept running.\u003c/p\u003e\n\n\u003cp\u003eIn the first episode of The Friday Deploy, they break down how they rebuilt Fireside while it was live, including a jump from Postgres 9.5 to 18 with no downtime for listeners. They talk about reverse-engineering undocumented infrastructure, using Flipper to put the application into read-only mode, testing migrations until they became boring, and letting agents carry work all the way to the final approval.\u003c/p\u003e\n\n\u003cp\u003eThis is not a story about giving an AI agent one prompt and letting it loose on production. It is about breaking dangerous work into small, verifiable steps and knowing where experience and taste still matter.\u003c/p\u003e\n\n\u003cp\u003eThey also get into:\u003c/p\u003e\n\n\u003cul\u003e\n\u003cli\u003e  Why verification matters more than another round of prompting\u003c/li\u003e\n\u003cli\u003e  How multiple models can provide independent reviews\u003c/li\u003e\n\u003cli\u003e  Giving agents safe, read-only access to production context\u003c/li\u003e\n\u003cli\u003e  Keeping deterministic work out of nondeterministic agents\u003c/li\u003e\n\u003cli\u003e  Using real customer data to guide product and interface decisions\u003c/li\u003e\n\u003cli\u003e  Scheduled tasks as the beating heart of an AI-assisted workflow\u003c/li\u003e\n\u003cli\u003e  Whether the next generation of software needs a traditional interface at all\u003c/li\u003e\n\u003c/ul\u003e\n\n\u003cp\u003eThe goal is not to eliminate risk. It is to gather enough evidence that shipping stops feeling like a leap of faith.\u003c/p\u003e\u003cp\u003eLinks:\u003c/p\u003e\u003cul\u003e\u003cli\u003e\u003ca title=\"Fireside\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkwODY4\"\u003eFireside\n\u003c/a\u003e\u003c/li\u003e\u003cli\u003e\u003ca title=\"Flipper\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkwODY5\"\u003eFlipper\n\u003c/a\u003e\u003c/li\u003e\u003cli\u003e\u003ca title=\"Flare\" rel=\"nofollow\" href=\"https://click.fireside.fm/e/MTkwODcw\"\u003eFlare\n\u003c/a\u003e\u003c/li\u003e\u003c/ul\u003e","summary":"AI can write the migration plan, inspect the servers, and even carry the work to the finish line. It still cannot decide what complexity is worth adding. John and Garrett talk about rebuilding Fireside, verifying dangerous changes, and why taste remains the difference between generating code and shipping dependable software.","date_published":"2026-09-25T13:00:00.000-04:00","attachments":[{"url":"https://aphid.fireside.fm/d/1437767933/cf46278b-b0e2-4c19-bb2d-a4220cbf6aab/e0839f74-3d30-43d4-b914-6d1492c48ead.mp3","mime_type":"audio/mpeg","size_in_bytes":80586731,"duration_in_seconds":3326}]}]}