Standing in the Fire cover art

Standing in the Fire

Standing in the Fire

By: Very Good Software
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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.© 2026 Very Good Software, LLC Economics Leadership Management & Leadership Marketing Marketing & Sales
Episodes
  • Bonus Episode: Open Loops, Hiring Pains, and Not Quitting
    Jun 24 2026

    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.

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    30 mins
  • 13: Running on Empty: Burning Out, Finding Margin, and Growing on Purpose
    Jun 10 2026

    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.

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    36 mins
  • 12: Chest Tight, Calendar Full: Finding the Off Switch in a Season of Growth - Ep. 12
    May 13 2026

    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?

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    39 mins
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