app03 Fri, 25 Sep 2026 18:27:28 +0000 Fireside (https://fireside.fm) The Friday Deploy https://thefridaydeploy.fireside.fm Fri, 25 Sep 2026 14:26:08 -0400 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. en-us © 2026 The Friday Deploy episodic Ship on Friday. Sleep through the night. John Nunemaker 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. false John Nunemaker john@fireside.fm Episode 1: Changing the Wheels While the Car Is Moving https://thefridaydeploy.fireside.fm/1 e0839f74-3d30-43d4-b914-6d1492c48ead Fri, 25 Sep 2026 13:00:00 -0400 john@fireside.fm (John Nunemaker) full John Nunemaker 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. 55:26 false 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.

Two years later, almost every piece has been replaced while podcasts, feeds, and downloads kept running.

In 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.

This 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.

They also get into:

  • Why verification matters more than another round of prompting
  • How multiple models can provide independent reviews
  • Giving agents safe, read-only access to production context
  • Keeping deterministic work out of nondeterministic agents
  • Using real customer data to guide product and interface decisions
  • Scheduled tasks as the beating heart of an AI-assisted workflow
  • Whether the next generation of software needs a traditional interface at all

The goal is not to eliminate risk. It is to gather enough evidence that shipping stops feeling like a leap of faith.

]]> 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.

Two years later, almost every piece has been replaced while podcasts, feeds, and downloads kept running.

In 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.

This 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.

They also get into:

  • Why verification matters more than another round of prompting
  • How multiple models can provide independent reviews
  • Giving agents safe, read-only access to production context
  • Keeping deterministic work out of nondeterministic agents
  • Using real customer data to guide product and interface decisions
  • Scheduled tasks as the beating heart of an AI-assisted workflow
  • Whether the next generation of software needs a traditional interface at all

The goal is not to eliminate risk. It is to gather enough evidence that shipping stops feeling like a leap of faith.

Links:

]]> 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.

Two years later, almost every piece has been replaced while podcasts, feeds, and downloads kept running.

In 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.

This 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.

They also get into:

  • Why verification matters more than another round of prompting
  • How multiple models can provide independent reviews
  • Giving agents safe, read-only access to production context
  • Keeping deterministic work out of nondeterministic agents
  • Using real customer data to guide product and interface decisions
  • Scheduled tasks as the beating heart of an AI-assisted workflow
  • Whether the next generation of software needs a traditional interface at all

The goal is not to eliminate risk. It is to gather enough evidence that shipping stops feeling like a leap of faith.

Links:

]]> https://fireside.fm/player/v2/wKHjBfwC+s5MvqGP7 ]]> John Nunemaker Garrett Dimon