Standing in the Fire

Very Good Software

Dive into the fire with Kris, Garrett and John — three owners of Fireside.fm who know what it’s like to stand in the flames of entrepreneurship. In 'Standing in the Fire,' we tackle everything from the latest trends in podcasting to the realities of running a SaaS business. No scripts, no filters — just real talk about what it takes to keep the fire burning. Join us as we explore the triumphs, struggles, and surprising lessons learned along the way.

  1. Sep 29

    16: How Codex Fixed a Year and a Half of Bugs in Four Hours

    Big episode. Kris crossed the line. John's running out of tokens again. And there's a lot of ground to cover. Topics covered: [0:00] Intro & Back From Summer [1:17] Kris Installs Codex (Finally) [3:36] Founder Fellowship: 5 Vibe Coders Walk In [6:20] Hot Take: Will You Even Need to Learn to Code? [9:36] Getting Unlocked vs. Getting Generic Answers [11:06] AI Art in Client Brochures — A Trust Problem [13:23] Automating Social Media with Box Out [17:34] Trial Reels, Algorithm Games, and Quantity Over Timing [20:09] Onboard Your Own Product — On Repeat [23:50] Fireside New Site & Automated Weekly Emails [26:34] GStack: Build a Feature From Scratch With Bumpers [30:11] Building a Founder Fellowship Tracking App [33:47] Todoist + MCP — Logging the Admin Work That Doesn't Count [35:28] Flare Performance Reports Every Morning [38:49] What's Shipping at Fireside This Week [41:10] OpenAI Astra: Burned a Week of Tokens Before Breakfast [48:14] The Virtuous Loop: Codex Fixed 18 Months of Bugs [52:00] Recommendations: GStack, Astra & Leaders Eat Last Mentioned: OpenAI Codex / Astra GStack (Gary Tan / Y Combinator) Flare: app performance monitoring Box Out Speaker Deck Fireside.fm Momentum Founder Fellowship UserList — lifecycle email Todoist + MCP integration Cloudflare (for building lightweight apps) Jesse Hanley / Bento Grok / Grok Bot Like, follow, and leave a comment. First one's still up for grabs. Standing in the Fire is produced in South Bend, Indiana.

    16: How Codex Fixed a Year and a Half of Bugs in Four Hours
  2. Jun 10

    13: Running on Empty: Burning Out, Finding Margin, and Growing on Purpose

    In this episode of Standing in the Fire, Kris and John pull back the curtain on what life actually looks like when you're managing multiple SaaS products, a coworking space, and a life that doesn't have a quiet corner right now. What We Cover Into the Fire: What's Been Hard Kris opens up about a stretch where nothing feels like an oasis: hiring pressure, prepping for a big idea week at Momentum, and the small but real win of finally getting those emails out. John reflects on going deep into AI work with no buffer — and how a camping trip to Disney gave him the margin he didn't know he needed. Fan the Flames: What's Been Inspiring John shares a conversation with a friend about Essentialism and a question that's been sitting with him: what does intentional growth actually look like? Growing a business past a certain point means doing things you don't enjoy — so what do you really want? Kris has been listening to Personality Isn't Permanent, a change of pace from the typical hustle-heavy business books. Embers: Small Wins and Experiments Fireside's episode upload flow is getting a real look: streamlined fields, drag-and-drop uploads, and AI-suggested metadata from transcripts are all on the roadmap Momentum is solving a surprisingly relatable problem: members don't want to leave when they're in the zone, with a dead-simple iPad + Square terminal snack shop Fireside cover art generation is in early exploration: episode art, built right into the platform Podcast Rec of the Episode John's been listening to Physics of Startups on the road, specifically the "translation guide" episode on B2B sales and the push/pull framework. Highly recommended for anyone who's ever done a customer discovery call and walked away more confused than when they started. Standing in the Fire is produced in South Bend, Indiana.

    13: Running on Empty: Burning Out, Finding Margin, and Growing on Purpose
  3. May 13

    12: Chest Tight, Calendar Full: Finding the Off Switch in a Season of Growth - Ep. 12

    Ever feel like you're winning and burning out at the same time? That's the tension at the heart of this episode of Standing in the Fire, the show where SaaS founders Chris and John skip the highlight reel and get into the actual heat of building businesses. What's In the Fire This Week John opens up about hitting a wall after weeks of peak AI productivity. The work was getting done, more than ever, but the cost was invisible: no mental space, chest tightness, podcasts in the car, laptop on the couch, doomscrolling AI Twitter at midnight. He breaks down what recovery actually looked like: basketball, pantry shelves, a journaling workbook, and an E Ink notebook for thoughts he doesn't even need to keep. Kris brings the counterweight: a trip to Austin for pre-South by Southwest events with a room full of women founders at varying stages (bootstrapped, PE-backed, VC-funded, exited, bought back). The caliber of story and the in-person energy reminded him what's been missing: community, events, and the kind of conversation you can't get from a podcast. "It's not a different caliber of people, it's different experiences. And that changes everything." Fan the Flames: What's Been Inspiring Brainstorming with Claude as a thinking partner, not just a tool, exploring business ideas you don't have to build Reading Cornelius Vanderbilt and wondering: what gave historical figures their relentlessness? Was it just that there was nothing to do after dark except sit by the fire? Watching teammates build the impossible, like Box Out's OCR feature that extracted a name from a photo where a spiral notebook was covering half the letters Ember Updates: Small Wins Worth Noting Segmented email onboarding finally live for Speaker Deck - and the lesson: just launch with three emails, don't wait for seven Geo SEO / AI visibility auditing - a WordPress plugin that scores how well your site shows up in LLM responses, generates an llms.txt file, and gives you a prioritized fix list you can paste straight into Claude LLM self-verification as a design pattern - the insight that AI output is only as good as its ability to check its own work. Give it an API to render what it just built, compare against a reference, and let it loop until it gets there. Game-changing for template generation at Box Out. The Thread That Ties It Together Whether it's burnout recovery, event planning, email automation, or AI architecture, this episode keeps circling back to the same question: how do you define success clearly enough that the system (human or AI) can actually get there? Standing in the Fire is produced in South Bend, Indiana.

    12: Chest Tight, Calendar Full: Finding the Off Switch in a Season of Growth - Ep. 12

About

Dive into the fire with Kris, Garrett and John — three owners of Fireside.fm who know what it’s like to stand in the flames of entrepreneurship. In 'Standing in the Fire,' we tackle everything from the latest trends in podcasting to the realities of running a SaaS business. No scripts, no filters — just real talk about what it takes to keep the fire burning. Join us as we explore the triumphs, struggles, and surprising lessons learned along the way.

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