{"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":"2026-09-25T13:00:00.000-04:00","explicit":false,"owner":"John Nunemaker","image":"https://media24.fireside.fm/file/fireside-images-2024/podcasts/images/c/cf46278b-b0e2-4c19-bb2d-a4220cbf6aab/cover.jpg?v=2"},"items":[{"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":79845712,"duration_in_seconds":3326}]}]}