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.

Episodes

  1. 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

  2. 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

  3. 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

  4. 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

  5. 02/05/2025

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

    Celebrating tech wins in a way that resonates with customers can be tricky—so how should SaaS companies do it? John, Kris, and Garrett break down how they approach communicating improvements, from backend optimizations to feature rollouts. They debate whether customers care about upgrades like Rails 6 and share ideas on writing updates that connect with both technical and non-technical users. The conversation then shifts to hiring—how to evaluate developers, why trade-offs are crucial in the interview process, and the unique challenges of hiring remote vs. local talent. John shares insights from his GitHub hiring experience, Kris talks about building teams for different projects, and Garrett explores the psychology behind finding people who truly align with company culture. The episode wraps up with wins of the week, including major Fireside updates, basketball coaching victories, and a heated discussion about Notre Dame football. Key Quotes "If you don't celebrate, it can feel like nothing is happening—even when big things are." "Customers don't care about Rails upgrades, they care about how fast and smooth their experience is." "Hiring is as much about culture fit as it is about technical ability." Takeaways Celebrating tech wins authentically is crucial for customer engagement. Customers care more about stability and bug fixes than technical upgrades. Effective communication of tech improvements can enhance customer trust. Hiring processes differ significantly between startups and larger companies. Cultural fit is essential when hiring, especially in remote teams. Technical evaluations should focus on problem-solving and trade-offs. Building a positive company culture requires intentional effort and understanding. Non-technical founders can benefit from involving technical friends in hiring. Celebrating small wins can boost team morale and motivation. Understanding employee motivations is key to fostering a supportive work environment.

    41 min

  6. 01/09/2025

    4: Black Friday Reflections and New Year Opportunities

    This episode tackles the highs and lows of Black Friday marketing and its relevance to SaaS businesses like Fireside. John, Kris, and Garrett discuss how customer-centric timing could outperform traditional holiday discounts, with ideas ranging from New Year podcasting pushes to conference-aligned offers. The trio also delves into the backend challenges of modernizing software, balancing Rails upgrades with visible customer improvements, and finding psychological triggers to help customers start and sustain new initiatives. They share insights on turning performance boosts into happy customers and why community-building could hold the key to podcasting success. Key Quotes “What if instead of discounts, we focused on lowering the risk for customers to try podcasting?” - Garrett “You don't have to go crazy and work a ton. You can you can achieve great success by turning a few levers. But sometimes it just takes a lot of work to figure out what those levers are.” - John "I'm just thinking about swag, but that's a discussion from another day." - Kris "I feel like that's the thing with SaaS in general. I'm sure some people have gone viral, new product just hit the sweet spot, nailed it, they knew exactly what they're doing, had a bunch of experience. But, on the other hand, every other SaaS app I've been involved in, it is nothing but just slow and steady constant improvements that are customer centric. And eventually at some point you've removed enough of the friction in onboarding, registration, daily usage, whatever it is, you know, either it combats churn a little bit or it increases registrations. And then, you look back three years later and you're like, it got there. But without that immediate reward all the time, it's definitely challenging to keep the faith." - Garrett

    44 min

  7. 12/24/2024

    3: Mastering Prioritization in SaaS

    The art of prioritization takes center stage in Episode #3 of “Standing in the Fire.” John, Kris, and Garrett explore how they balance the demands of running multiple SaaS companies, tackling technical debt, strategizing marketing efforts, and avoiding burnout. From Rails upgrades to marketing plans and hard-stop productivity hacks, this conversation reveals how founders navigate the chaos to move their businesses forward. Tune in for relatable stories, practical tips, and a touch of humor about the realities of entrepreneurship. Prioritization is a constant challenge for founders. Balancing multiple projects requires clear focus and boundaries. Customer satisfaction is tied to visible improvements. Setting specific goals can help guide daily tasks. Rest and downtime are essential for sustained productivity. Planning ahead can significantly boost daily productivity. It's important to recognize the value of small wins. Managing a backlog is a necessary part of software development. Effective communication within the team is crucial for progress. Creating a loyal customer base should be a top priority.

    37 min

  8. 12/17/2024

    2: Making Podcasting Less of a Pain

    The Standing in the Fire crew — John Nunemaker, Garrett Dimon, and Kristopher Priemer — returns with Episode #2, where they discuss: Customer feedback on integrating video and YouTube for podcasts. The friction points in podcast production, from editing to publishing. Ideas for simplifying workflows with tools, automation, and potential Fireside.fm features. Their recent development wins, including performance improvements and platform upgrades. Whether you’re a podcaster or just curious about the behind-the-scenes of building a SaaS app, this episode offers insights into problem-solving, customer experience, and the future of podcasting.

    25 min

  9. 11/09/2024

    1: Drinking Our Own Champagne

    Welcome to the first episode of Standing in the Fire, where John Nunemaker, Garrett Dimon, and Kristopher Priemer share their journey as the new owners of Fireside.fm. This podcast isn’t just about running a SaaS business—it’s about living the Fireside experience as podcast hosts and users. In this episode, we: Introduce the team and their backgrounds in software, marketing, and entrepreneurship. Explore the challenges and excitement of owning and improving a podcast hosting platform. Discuss the importance of drinking your own champagne (aka eating your own dog food) and connecting with customers. Share our vision for Fireside.fm, from better analytics to fostering a podcaster community. Join us as we navigate the highs and lows of entrepreneurship, building great software, and helping podcasters thrive.

    32 min
  • 9 Episodes

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 - 2025
  • Episodes
    9
  • Rating
    Clean
  • Copyright
    © 2026 Very Good Software, LLC
  • Show Website
    Standing in the Fire