Standing in the Fire

About Standing in the Fire

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.

Publisher

Very Good Software

Category

business · business

Language

en

Explicit

No

First episode

9 Nov 2024

Latest episode

22 Oct 2026

Latest episodes

19 episodes in the feed.

1. 

   22 Oct 2026

   18: Nobody Wants Your Web UI Anymore

   This week we start with the small wins. Two Momentum coworking members grew enough to upgrade to offices, and Fireside shipped Air, a clean new website theme built around your cover art. Then John plants his flag: within a few years, chat will replace clicking around in web apps. He's already stopped opening the dashboards for the tools he uses every day. Kris pushes back on behalf of the huge non-technical crowd that's still asking AI to rewrite their emails. From there it gets personal. Why working with AI all day makes people feel harder, what to do with all the open loops in your head, waking up with dread, finally sending the ask you've been avoiding, and real advice on getting better sleep. And John explains why he's back on Claude after building a polished iPhone dice game in an afternoon. In this episode: Why members who outgrow coworking might be the best proof it works Projecting success, and when it backfires Fireside's new Air theme with light and dark modes The web UI is disappearing, and what replaces it Why AI-written tests are slowing everyone down Async AI work vs. synchronous people Using an AI project manager to clear the deck Sleep, caffeine, cortisol, and shutting your brain off Asking for what you want, even when it feels awkward Building custom tools that solve only your problem Just doing the thing instead of ruminating on it

2. 

   13 Oct 2026

   17: Nobody Needs the Tutorial Anymore

   John just got back from Rails World in Austin, his first conference of the AI era. One Cybercab ride had him seeing the future. Then hallway conversations about consulting drying up and apps losing revenue brought him right back down. Kris shares the highs and lows of building Momentum, why AI-generated art is slowing down production at the screen print shop, and the new rule he wants for anyone sending AI reports without checking them first. Plus, Kris starts shipping real changes with Codex, and Fireside turns two. Show Notes: Celebrating wins when you're the one who has to lead the celebration Rails World, robotaxis, and why self-driving could be everywhere in two to five years What happens to consulting when every small business has an AI subscription Why AI art makes screen printing slower, not faster How to price work fairly when AI does most of it Verification as the most important skill right now Using Codex on a WordPress site, and a banner page that finally converted Why project managers pick up AI coding faster than you'd expect What happens when your software is a black box Fireside's two-year anniversary

3. 

   29 Sept 2026

   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.

4. 

   10 Aug 2026

   15: Hot Takes: AI Art, Vibe Coding, and Why Codex Isn't All Bad

   Sometimes the thing that's slowing you down isn't the business, it's the nasal spray. John's back, feeling good, and firing on all cylinders. Kris is deep in the work of letting go. This one's equal parts founder therapy and technical nerd session. Show Notes: (0:00) Intro: Starting with the Wins (0:39) It Was the Flonase (John's Back) (2:39) Collecting Validation: Save the Wins Too (5:11) The Fireside New Studio: What's Working (10:04) Delegate or Die: Letting Go Without Losing Control (12:33) New Segment: Sparks Fly (Hot Takes) (13:05) Hot Take: AI Art Is Ruining the Print Shop (20:01) Hot Take: Codex Isn't All Bad (24:59) Vibe Coding: What Nobody Tells You (28:29) Fan the Flames: Try More Than One AI (30:07) The Busy Light Saga (35:28) Embers: Momentum Startup Cohort (37:22) Embers: Podcast Art & Thumbnail Strategy (38:20) Surviving a 5-Hour Railway Outage with Claude (44:45) Flare, Box Out Click Tracking & What's Next Check Out John's Stuff: Fireside.fm: https://fireside.fm (https://fireside.fm/) Flipper Cloud: https://www.flippercloud.io (https://www.flippercloud.io/) Check Out Kris's Stuff: Momentum – Coworking space in South Bend: https://momentumsb.com (https://momentumsb.com/) Access Imprints – Screen printing & embroidery: https://accessimprints.com (https://accessimprints.com/) The Hardest Thing Podcast: https://hardestthingpod.fireside.fm (https://hardestthingpod.fireside.fm)

5. 

   3 Aug 2026

   14: Stop Fixing Every Bug (And Let Claude Handle the Rest)

   John (https://x.com/jnunemaker (https://x.com/jnunemaker) ) and Kris (https://www.instagram.com/kristopherpriemer (https://www.instagram.com/kristopherpriemer)) talk about the real side of running multiple businesses: open loops, hiring pains, patience, and what actually keeps founders going. Show Notes: (00:00) Intro & Catching Up (01:39) Into the Fire: Idea Week Debrief (02:58) Coworking Pivot: Why Private Offices Win (06:42) New Category Thinking (Grüns Gummies) (08:12) How to Fund the Build-Out (08:52) Into the Fire: Health, Friendship & Hell Yeah or No (11:06) Who You're Around Changes Everything (12:23) Fan the Flames: Graham Weaver's Asymmetric Life (14:07) Personality Isn't Permanent & Leadership Presence (16:23) Cornelius Vanderbilt & the Art of No Grudges (22:21) GStack: Gary Tan's AI Dev Workflow (24:36) Using Claude to Fix WordPress Bugs (26:33) YouTube Rabbit Holes & What John's Feed Looks Like (28:29) Embers: Fireside, Flare & Flipper Updates (33:05) Building an AI Watchdog That Redeploys at 3am (38:23) Daily GitHub Summaries for $20/month Check Out John's Stuff: Fireside.fm – Podcast hosting for serious podcasters: https://fireside.fm (https://fireside.fm/) Flipper – Feature flag management: https://www.flippercloud.io (https://www.flippercloud.io/) Check Out Kris's Stuff: Momentum – Coworking space in South Bend: https://momentumsb.com (https://momentumsb.com/) The Hardest Thing Podcast – https://hardestthingpod.fireside.fm (https://hardestthingpod.fireside.fm)

6. 

   24 Jun 2026

   Bonus Episode: Open Loops, Hiring Pains, and Not Quitting

   A lost episode, finally found and worth the wait. John and Kris get into the real conversations founders rarely have out loud. Topics covered: Recording in person vs. remote - why it changes everything from the conversation to the edit Zoom fatigue and the surprising reason video calls wear you out The compounding effect: Atomic Habits applied to building a podcast (and a business) Hiring contractors vs. in-person employees - the messier, harder reality Patience as a founder - why wanting things to move faster creates its own kind of damage Open loops, stress, and why celebrating closed wins matters more than we admit The cost of being a yes-person when your time is your most valuable asset What's fueling the fire: books, podcasts, community events, and people showing up Mentioned: Atomic Habits – James Clear Ready, Fire, Aim – Michael Masterson $100M Leads – Alex Hormozi My First Million Podcast Momentum (coworking space, South Bend) Like, follow, and leave a comment, it genuinely helps.

7. 

   10 Jun 2026

   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.

8. 

   13 May 2026

   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?

9. 

   17 Apr 2026

   Ship It Fast, Fix It Later - The New SaaS Playbook

   What happens when the coffee runs out, and everything else goes sideways too? Kris and John are back with a new episode format built around three segments: what's been hard, what's been inspiring, and what's been shipping. No highlight reels. Just the real stuff. 🔥 Into the Fire - What's Been Hard Momentum was built around great amenities. Draft lattes. Cold brew on tap. Pour-over. The works. So when the RO water system ran dry and the kegs went empty first thing in the morning, chaos ensued. Kris breaks down their own version of "Watergate" — and what it revealed about turning a customer frustration moment into surprise and delight. John gets honest too: the constant tension between deep builder mode and staying on top of customer support is real. Plus — why good AI support bots are genuinely useful, and why bad ones make you want to throw your laptop. 📖 Fan the Flames - Recommendations Worth Your Time John just finished Alex Hormozi's $100M Money Models and one subtle pricing reframe completely changed how he thinks about annual plans. Instead of offering a discount, give bonus months. Small shift, big psychological difference. Kris connects it to membership sales at Momentum and brings in Ryan Serhant's obsessive follow-up philosophy: people who don't respond aren't always uninterested. A three-month-cold lead just booked a tour. Kris's tool pick: Jesse Itzler's wall calendar for mapping out an entire year intentionally, personally and professionally. They used it to plan 75 events without losing their minds. ✨ Embers - Small Wins & Things Shipping John shipped Ember, a brand new embeddable podcast player for Fireside, and then turned a single customer feature request into a working playlist player in under an hour. The customer's response? "This is unreal." The lesson: getting something good to production fast beats waiting for perfect. AI-assisted development has changed what's possible for small teams, and John's sticky note says it all "What has to be true for it to take half the time?" Chris closes with some news: he's been named Outstanding Young Business Leader of the Year by the South Bend Regional Chamber, and yes, he announced it at Christmas dinner to very confused nieces. Standing in the Fire is about what it actually feels like to own and grow SaaS products. Hosted by John and Kris, owners of Fireside.fm. New episodes dropping consistently, sometimes. Like what you hear? Subscribe. It helps more than you know.

10. 

    23 Mar 2026

    10: The Neo Moment

    In this episode, Kris and John dig into what's been hard and stretching lately — from December's packed schedules to leveling up the Box Out conference booth, hiring challenges at the print shop, and keeping Momentum's big vision alive through the day-to-day grind. John shares his obsession with Claude Supermax and how switching to Opus-level AI coding has unlocked a "Neo in the Matrix" moment — pushing Speaker Deck links, Flipper Expressions, Box Out page views, and Fireside episode duplication all forward in a single week. Kris recommends Opus (the video tool) for turning landscape podcast footage into vertical social clips. They wrap up with goals for the new year: John wants to 2-4X his output, while Kris is focused on filling Momentum, growing strategically, and finding better work-life integration.

11. 

    24 Nov 2025

    Back in the Studio: A Summer Break, Big Plans, and Momentum

    In this episode of Standing in the Fire, John and Kris return after a summer break and settle into the new Fireside studio inside the Momentum Entrepreneurship Hub—an ambitious space they helped bring to life in South Bend. With Garrett remote in Colorado, the two hosts talk about why recording in-person felt like the right move for now, how the summer unfolded, and what it took to get the hub open, from construction chaos to a packed ribbon-cutting. They share stories about landing big-name visitors—including the co-founder of Hotwire and an early investor in Facebook and Slack—along with pitch nights, food in the fridge, and the surprisingly important role of community. The conversation drifts into reflections on their first year owning Fireside: the plans they thought they’d tackle, the reality of maintenance and customer needs, and the satisfaction of making publishing reliable and metrics faster again. From T-shirt shipments across the world to planning the next iteration of the Fireside marketing site, John and Kris talk openly about learning to set more realistic goals, building foundations before flash, and the excitement of seeing long-term vision start to take shape. They wrap by looking ahead—Black Friday plans, product improvements, onboarding upgrades, and maybe even hosting a creator gathering in South Bend. It’s casual, honest, funny, and a great reset episode before the momentum picks up again.

12. 

    13 May 2025

    The SaaS Checkup: What You Should Audit Every Year (But Probably Don’t)

    Host John and his guest explore essential annual audits for SaaS applications, covering onboarding, churn reduction, customer communication, and pricing to ensure product health.

13. 

    21 Mar 2025

    Stop drowning in tasks, start buying back your time

    Host John and guest Kris discuss Dan Martell's "Buy Back Your Time," revealing how founders can delegate smarter and systemize better to reclaim their valuable time.

14. 

    10 Mar 2025

    6: The Art of Sharing Knowledge in Teams

    John, Kris, and Garrett discuss effective strategies for documenting and sharing company knowledge to boost team efficiency and accessibility.

15. 

    5 Feb 2025

    5: Tech Wins & Hiring Woes: How to Communicate, Celebrate, and Find the Right People

    John, Kris, and Garrett discuss communicating tech wins effectively and share strategies for evaluating developers and building strong company cultures in this interview.

16. 

    9 Jan 2025

    4: Black Friday Reflections and New Year Opportunities

    John, Kris, and Garrett discuss Black Friday marketing strategies and New Year opportunities for SaaS businesses, exploring customer-centric timing and software modernization challenges.

17. 

    24 Dec 2024

    3: Mastering Prioritization in SaaS

    John, Kris, and Garrett discuss mastering prioritization in SaaS, sharing strategies for balancing multiple demands and avoiding burnout in this interview.

18. 

    17 Dec 2024

    2: Making Podcasting Less of a Pain

    John Nunemaker, Garrett Dimon, and Kristopher Priemer discuss simplifying podcast production workflows and integrating video for a better listener experience.

19. 

    9 Nov 2024

    1: Drinking Our Own Champagne

    John Nunemaker, Garrett Dimon, and Kristopher Priemer discuss their journey as new owners of Fireside.fm, emphasizing the importance of using their own platform to connect with customers.

Podcast Authority Score: 20 / 100

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