Standing in the Fire

By: Very Good Software
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  • Summary

  • 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.
    © 2025 Very Good Software, LLC
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Economics Leadership Management & Leadership Marketing Marketing & Sales
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Episodes
  • 6: The Art of Sharing Knowledge in Teams

    6: The Art of Sharing Knowledge in Teams
    Mar 10 2025
    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."
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    28 mins
  • 5: Tech Wins & Hiring Woes: How to Communicate, Celebrate, and Find the Right People

    5: Tech Wins & Hiring Woes: How to Communicate, Celebrate, and Find the Right People
    Feb 5 2025
    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.
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    41 mins
  • 4: Black Friday Reflections and New Year Opportunities

    4: Black Friday Reflections and New Year Opportunities
    Jan 9 2025
    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
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    44 mins

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