Standing in the Fire

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.

  1. 13: Running on Empty: Burning Out, Finding Margin, and Growing on Purpose

    2d ago

    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.

    36 min
  2. 12: Chest Tight, Calendar Full: Finding the Off Switch in a Season of Growth - Ep. 12

    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?

    39 min

  3. Apr 17

    11: 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.

    27 min

  4. Mar 23

    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.

    30 min

  5. 11/24/2025

    9: 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.

    24 min

  6. 05/13/2025

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

    Inspired by John’s real-life annual physical, this episode explores what it means to give your SaaS app its own annual checkup. What should you audit regularly to keep your app healthy? The guys cover: • 🩺 Auditing automated onboarding and transactional emails • 🧪 Building a Customer Health Index to proactively reduce churn • 📉 How and when to talk to customers—without annoying them • 📬 Rethinking drip campaigns and newsletters so they actually get read • 🛠️ Revisiting your content, SEO metadata, accessibility, and dependencies • 💵 Why your pricing probably needs a tune-up It’s packed with tactical insights and spicy opinions, like: “If you reply to an email I claim is from me—it better come to me.” “Most teams don’t need more email. They need better email.” “Documentation, accessibility, and alt text… yep, we forget those too.” This one will leave you with a solid checklist for improving your product, process, and communication in the year ahead.

    47 min

  7. 03/21/2025

    7: Stop drowning in tasks, start buying back your time

    What if you could focus only on what truly moves the needle? John and Kris dig into Buy Back Your Time by Dan Martell and explore how founders can delegate smarter, systemize better, and scale faster. Key Takeaways: You can always get more money, but you can never get more time. Outsource tasks that drain your energy and time. Creating playbooks can streamline delegation and training. Hiring should focus on finding the right fit through practical projects. Energy and enthusiasm are contagious in leadership. Setting clear metrics helps track progress and success. Delegation is essential for scaling your business effectively. Systems are more important than goals for achieving success. Celebrating small wins can motivate teams and individuals. Understanding when a task is done is crucial for productivity. “You don’t hire to grow your business. You hire to buy back your time.” This episode is for founders drowning in tasks, solopreneurs hitting a ceiling, and anyone looking to escape the endless work treadmill. Challenge: Can you delegate one task this week? Let us know!

    47 min

  8. 03/10/2025

    6: The Art of Sharing Knowledge in Teams

    How does a growing SaaS company keep track of important knowledge? From server setups to customer success playbooks, every company builds a wealth of internal information—but too often, that knowledge is scattered, siloed, or locked away in someone’s head. In this episode, John, Kris, and Garrett explore how to document and share company knowledge effectively. They discuss real-world challenges, like merging Rails apps and ensuring critical infrastructure knowledge isn’t lost, as well as how to balance text-based documentation with video walkthroughs. Takeaways: Company knowledge management is crucial for team efficiency. Identifying challenges in knowledge sharing helps improve processes. Technical documentation should be thorough and accessible. Centralizing information can streamline communication. Choosing the right tools is essential for effective documentation. Video can enhance knowledge transfer but should be concise. Documentation needs to be regularly updated to remain relevant. AI has the potential to automate documentation processes. Creating a culture of knowledge sharing is important. Feedback from users can guide improvements in knowledge management. Key Quotes: "If you document nothing, the only knowledge management system you have is luck." "Slack is great for quick answers but terrible for long-term knowledge storage." "Your team should always know where to look before they have to ask." "Documentation is a moving target."

    28 min
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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.

Information

  • Creator
    Very Good Software
  • Years Active
    2024 - 2026
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © 2026 Very Good Software, LLC
  • Show Website
    Standing in the Fire

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