PODCAST · technology
Maintainable
by Robby Russell
Do you feel like you're hitting a wall with your existing software projects? Are you curious to hear how other people are navigating this? You're not alone.On the Maintainable Software Podcast, Robby speaks with seasoned practitioners who have overcome the technical and cultural problems often associated with software development.Our guests will share stories in each episode and outline tangible, real-world approaches to software challenges. In turn, you'll uncover new ways of thinking about how to improve your software project's maintainability.
Episodes
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Gabriela Moreira: When 800 Tests Aren’t Enough
A large test suite should make developers feel safer changing software. Gabriela Moreira, CEO of Quint, has recently experienced something quite different: a new codebase grew from roughly 200 tests to 800 with the help of AI, yet she found herself trusting the suite less and manually verifying...
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Matija Šošić: Abstractions Aren’t Going Anywhere
What makes software maintainable might have less to do with how clean the code looks and more to do with how well it serves the people responsible for it. Matija Šošić, co-founder and CEO of Wasp, joins Robby to talk about boring and predictable code, resisting unnecessary abstractions, and why...
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José Valim: Designing a Language You Can Maintain for Decades
What does maintainability look like when the software you’re responsible for is a programming language? José Valim creator of Elixir and founder of Dashbit, joins Robby to talk about software that can “fit in your head,” the importance of clear boundaries, and why maintaining a language requires…
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John Athayde: Maintaining the User Side of Software
Software maintainability is often discussed through the codebase, but users experience years of accumulated decisions through the interface. John Athayde of Meticulous joins Robby to examine maintainability from the front-end and product-design side, starting with documentation and the context it...
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Kristin Isaac: The Customer Doesn’t Care About Your Technical Debt
Technical debt rarely arrives in a support ticket labeled “technical debt.” Customers experience something simpler: the product is slow, unreliable, or the same problem keeps coming back. Kristin Isaac, Co-Founder and CEO of Strudel, joins Robby to look at software maintainability from the…
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David Hayes: Boring Software, Clear Incentives, and Better Checklists
Drawing from his experience at PagerDuty, Sentry, and now FusionAuth, he joins Robby to explore what happens when software becomes trusted infrastructure. Their conversation touches on API design, naming things, product management, self-hosted software, and why customers rarely upgrade as quickly...
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Diana Pfeil: Building Confidence in Probabilistic Systems
Machine learning systems can degrade even when the underlying code has not changed. Diana Pfeil of Sunbeam Consulting joins Robby Russell on Maintainable to explain how changing data, model behavior, and non-deterministic outputs create a different kind of maintenance challenge. Rather than…
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Chris Coyier: The Long Game of Maintaining CodePen
What does it take to keep a product healthy after more than 15 years of continuous evolution? In this episode, Robby Russell talks with Chris Coyier, co-founder of CodePen, about the long game of maintaining software. Chris shares how CodePen has evolved over time, the trade-offs involved in...
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Sally Lait: Confidence Is the Real Metric
Sally Lait joins Robby Russell on Maintainable to explore software maintainability through a different lens… not just code quality, but how teams work together over time. Sally is a fractional technology leader and advisor with more than two decades in the industry. You can follow her on LinkedIn...
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Rein Henrichs: The Real Work of Maintenance Happens Before You Touch the Code
Software maintenance is often framed as a technical problem. Refactoring code, fixing bugs, or upgrading dependencies. In this conversation, Robby Russell talks with Rein Henrichs about a different lens, one centered on understanding. Rein is a Principal Software Engineer at Procore, where he…
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Russ Olsen: The Hidden Cost of Forgetting Why the Code Looks Like That
Software doesn’t become hard to maintain only because the code is messy. It often becomes hard to maintain because the reasoning behind it disappears. In this episode of Maintainable, Robby Russell talks with Russ Olsen about trade-offs, legacy systems, and why maintainability depends on context...
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Joel Oliveira: Predictability Is a Maintainability Feature
Long-lived software systems rarely stay tidy. Over time they accumulate decisions, workarounds, and layers of history that can make even simple changes feel risky. For engineers responsible for maintaining those systems, the challenge often becomes less about writing new code and more about...
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Lucas Roesler: The Fast Feedback Loop Advantage
Maintaining software over time rarely fails because of one bad decision. It fails because teams stop getting clear signals… and start guessing. In this episode, Robby talks with Lucas Roesler, Managing Partner and CTO at Contiamo. Lucas joins from Berlin to unpack what maintainability looks like…
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Brittany Ellich: Using AI to Maintain Software, Not Rewrite It
Rewrites are seductive. Clean slates promise clarity, speed, and “doing it right this time.” In practice, they’re often late, over budget, and quietly demoralizing. In this episode of Maintainable, Robby sits down with Brittany Ellich, a Senior Software Engineer at GitHub, to talk about a…
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Kent L Beck: You’re Ignoring Optionality… and Paying for It
Kent Beck: You’re Ignoring Optionality… and Paying for It In this episode of Maintainable, Robby speaks with Kent Beck, a foundational voice in modern software development and author of Tidy First?. Kent joins from California to explore why optionality is a central, often underestimated dimension...
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Don MacKinnon: Why Simplicity Beats Cleverness in Software Design
Episode Highlights [00:00:48] What Makes Software Maintainable Don explains why unnecessary complexity is the biggest barrier to maintainability, drawing on themes from A Philosophy of Software Design. [00:03:14] The Cost of Clever Abstractions A real story from a Node.js API shows how an unused...
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Chris Zetter: Building a Database to Better Understand Maintainability
Episode Summary In this conversation, Robby sits down with software engineer and author Chris Zetter to explore what building a relational database from scratch can teach us about maintainability, architectural thinking, and team culture. Chris shares why documentation often matters more than...
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Denis Rechkunov: When Consistency Becomes a Culture
Maintaining consistency across a sprawling codebase is one of the hardest challenges in software engineering. Denis Rechkunov, a Principal Software Engineer at Elastic, joins Robby to share how his team turned consistency into a cultural practice rather than a technical checklist. From managing...
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Nathan Ladd: Relentless Improvement and the Cost of Neglect
Episode Notes The discussion moves into how standards evolve beyond tools, the trade-offs of monocultures vs. consensus-driven teams, and why ownership matters when the original authors move on. Nathan also unpacks the cost of neglect, describing defects as anything that slows developers down—not...
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Taylor Otwell: What 14 Years of Laravel Taught Me About Maintainability
Taylor Otwell, creator of Laravel and CEO of Laravel LLC, joins Robby to reflect on his 14-year journey building and maintaining one of the most popular web frameworks in the world. From its PHP 5.3 origins to a full-time business with a 70-person team, Taylor shares what he's learned about code...
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Sara Jackson: Why Resilience Is a Team Sport
Robby is joined by Sara Jackson, Senior Developer at thoughtbot, to explore the practical ways teams can foster resilience—not just in their infrastructure, but in their everyday habits. They talk about why documentation is more than a chore, how to build trust in test suites, and how Chaos...
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Joel Chippindale: Why High-Quality Software Isn’t About Developer Skill Alone
CTO coach Joel Chippindale joins Robby to share what he's learned over two decades of building and leading software teams. Joel argues that maintainability has less to do with “clean code” and more to do with how teams communicate, prioritize, and make progress visible. Drawing on his time at...
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Melanie Sumner: Why Continuous Accessibility Is a Strategic Advantage
Melanie Sumner: Why Continuous Accessibility Is a Strategic Advantage Melanie Sumner, Product Accessibility Lead for Design Systems at HashiCorp, joins Robby to talk about what it takes to scale accessibility across legacy products—and how aligning design and engineering processes creates lasting...
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Joe Masilotti: Simplify Your Stack, Ship Mobile Sooner
In this episode of Maintainable, Robby speaks with Joe Masilotti, an independent consultant who helps Rails teams ship mobile apps using Hotwire Native. Joe shares his perspective on what makes software maintainable—especially for consultants who need to onboard quickly. He explains why setup...
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Freedom Dumlao: What 70 Java Services Taught Me About Focus
Freedom Dumlao (CTO at Vestmark) joins Robby to explore what it means to maintain software at scale—and why teams sometimes need to unlearn the hype. With two decades of experience supporting financial systems, Freedom shares how his team manages a Java monolith that oversees $1.6 trillion in...
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Mercedes Bernard: Friendly Code Welcomes Everyone In
Mercedes Bernard, Staff Software Engineer at Kit, joins Robby to talk about what it really means to write code that lasts—and who it should be written for. In this episode of Maintainable, Mercedes shares a thoughtful and practical perspective on working with legacy codebases, managing technical...
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Evan Phoenix: The Why of the One Line
Evan Phoenix (@evanphx), CEO of Miren, joins Robby to explore the subtle but powerful difference between writing code that works and writing code that explains itself. They discuss the role of clarity in maintainable systems, why splitting a monolith can backfire, and what developers can learn…
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Chris Salvato: Building Developer Paradise by Sitting in the Problem Space
Software isn’t always about rapid iteration. Sometimes, the real challenge lies in carefully assessing the existing environment. Chris Salvato, a Senior Staff Engineer at Shopify, believes that spending time in the “problem space” is vital for any long-lived application. Rather than diving...
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Heimir Thor Sverrisson: Architecture First, Tech Debt Second
Heimir Thor Sverrisson joins Robby to discuss the importance of software architecture in long-term maintainability. With over four decades in the industry, Heimir has witnessed firsthand how poor architectural decisions can set teams up for failure. He shares his experiences mentoring engineers,...
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Noémi Ványi: Only Fix Problems That Are Actually Problems
Not every messy piece of code needs a refactor. Noémi Ványi, Senior Software Engineer at Xata, joins Robby to discuss how to develop the intuition to know when refactoring is truly necessary and when it’s just unnecessary churn. She shares her approach to balancing pragmatism and maintainability,...
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Julia López: Code Tells a Story—Even the White Spaces
How much can legacy code tell us beyond just functionality? Julia López, Senior Software Engineer at Harvest, believes that even small details—such as white spaces, variable names, and formatting choices—can reveal a system’s history. In this episode, Julia and Robby discuss the importance of...
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Marty Haught: Rethinking Technical Debt—Is It Really Just Drift?
Episode Overview Marty Haught joins Robby to discuss the sustainability of open-source projects, the challenges of maintaining RubyGems, and why the metaphor of technical debt may not fully capture how software ages. Instead, he suggests thinking of it as drift—the natural misalignment of…
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Mike Bowers - From ISAM to JSON—Navigating 40+ Years of Database Evolution
Mike Bowers, Chief Architect at FairCom, has spent decades navigating the evolution of database technology. In this conversation, he and Robby explore the challenges of maintaining a 40+ year-old codebase, balancing legacy constraints with forward-thinking design, and the realities of technical...
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Lorna Mitchell: Writing Documentation Engineers Will Actually Read
Join Robby as he chats with Lorna Mitchell, open source advocate and technical writer, about the art of creating documentation that doesn’t gather dust. Lorna shares her experiences as a maintainer of the open source project RST2PDF, the value of API governance, and how documentation bridges gaps...
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Carola Lilienthal: Tackling Technical Debt with Patterns and Domain Knowledge
Episode Summary In this episode of Maintainable, Robby sits down with Carola Lilienthal, Software Architect and Managing Director at WPS. Together, they explore the intersection of cognitive science and software architecture, strategies for tackling technical debt, and why simplicity, modularity,...
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Joel Hawksley: The Hidden Costs of Frontend Complexity
Topics Discussed The importance of changeability as a core characteristic of well-maintained software. How GitHub has approached accessibility as a business and legal imperative. The evolution of GitHub’s frontend system, spanning over 2,000 pages, and the concept of "frontend vintages." Primer:...
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Austin Story: Making Software Easier to Change, Remove, and Evolve
Austin Story, Senior Engineering Director at Doximity, joins Robby to explore the intricacies of building maintainable systems, fostering team accountability, and enabling faster iteration without sacrificing quality. Austin shares how his team approached migrating from a monolithic GraphQL...
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Dan Moore: Building Developer-Friendly Authentication Solutions
Topics Covered Characteristics of Maintainable Software Dan emphasizes the importance of internal consistency in codebases, automated tests, and proper documentation to preserve decision-making context. [00:05:32] Internal consistency: Why it matters. [00:08:09] Lessons from maintaining legacy...
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Tom Johnson: From Auto-Documentation to Better Collaboration
In this episode of Maintainable, Robby speaks with Tom Johnson, Co-Founder and CEO of Multiplayer. Tom shares his perspectives on the evolving landscape of distributed systems, the challenges of maintaining legacy software, and how innovative tools are transforming the way teams collaborate.…
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Gulcin Yildirim Jelinek: Maintaining Postgres for Modern Workloads
In this episode of Maintainable, Robby speaks with Gulcin Yildirim Jelinek, a Staff Database Engineer at Xata. Joining from Prague, Czech Republic, Gulcin discusses her experiences working with legacy databases, the evolution of Postgres, and her passion for building accessible tech communities....
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Justine Gehring: Refactoring Software at Scale with AI
Robby sits down with Justine Gehring, an AI Research Engineer at Moderne, to explore how AI tools are transforming code maintenance and scalability. They dive into the unique ways AI can support refactoring for massive and legacy codebases, from retrieval-augmented generation (RAG) to lossless...
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Katerina Skroumpelou: Bridging Engineering and Advocacy for Scalable Software
As a product advocate at Nx, Katerina Skroumpelou combines her engineering skills with a knack for connecting with clients. In this episode, she shares how clear documentation, scalable architectures, and a collaborative culture can transform software development for the better. Key Takeaways...
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Moriel Schottlender: The Challenges of Modernizing MediaWiki's Monolith
Welcome to another engaging episode of the Maintainable Software Podcast! In this episode, Robby sits down with Moriel Schottlender, Principal Software Engineer at the Wikimedia Foundation, to explore the complex journey of modernizing MediaWiki, the software behind Wikipedia. Moriel shares her...
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Kate Holterhoff: From Front-End Engineering to Developer Advocacy
Welcome to another engaging episode of Maintainable! Robby sits down with Kate Holterhoff, Ph.D., a Senior Analyst at RedMonk and former front-end engineer, to explore the intricate world of software maintenance, documentation, and the future of developer roles. Kate brings her unique perspective...
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Alan Ridlehoover: Building Robust Systems Through Behavior-Centric Testing
Alan Ridlehoover: Building Robust Systems Through Behavior-Centric Testing In this episode of Maintainable, Robby speaks with Alan Ridlehoover, Senior Engineering Manager at Cisco Meraki. Alan shares his perspective on building well-maintained software by focusing on behavior-centric testing…
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April Wensel: Navigating Legacy Code with Compassion
In this episode of Maintainable, Robby speaks with April Wensel, Founder and Owner of Compassionate Coding. April shares her journey in the software industry and how she came to embrace compassion as a core value in coding and team dynamics. She explains why empathy is critical when working with...
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Saron Yitbarek: The Balance Between Maintainable Code and Multiple Streams of Income
In this episode of the Maintainable Software Podcast, Robby sits down with Saron Yitbarek, founder and CEO of DiscoLink, to explore the challenges of maintaining early-stage software while balancing multiple streams of income. Saron shares her journey from being a solo developer to hiring her…
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Lutz Hühnken: Crafting Resilient Systems with Event-Driven Design
Introduction In this episode of Maintainable, Robby speaks with Lutz Hühnken, Head of Engineering Excellence at Upvest, about the transformative power of event-driven architecture in software development. Lutz brings his extensive experience to the table, discussing how breaking down complex...
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Noel Rappin: Reviving the Pickaxe— A Journey through Ruby's Legacy
In this episode of the Maintainable Software Podcast, Robby is joined by Noel Rappin, Staff Engineer at Chime Financial, and the mind behind the latest edition of the classic Programming Ruby book, affectionately known as the "Pickaxe." Noel delves into the intricate process of modernizing a…
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Cassidy Williams: Navigating the Career Jungle Gym in Tech
In this episode of the Maintainable Software Podcast, Robby sits down with Cassidy Williams, Developer Advocate at GitHub, to explore the dynamic nature of a tech career, the delicate balance between clever code and maintainability, and the evolving trends in software development. Cassidy begins…
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ABOUT THIS SHOW
Do you feel like you're hitting a wall with your existing software projects? Are you curious to hear how other people are navigating this? You're not alone.On the Maintainable Software Podcast, Robby speaks with seasoned practitioners who have overcome the technical and cultural problems often associated with software development.Our guests will share stories in each episode and outline tangible, real-world approaches to software challenges. In turn, you'll uncover new ways of thinking about how to improve your software project's maintainability.
HOSTED BY
Robby Russell
CATEGORIES
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Frequently Asked Questions
How many episodes does Maintainable have?
Maintainable currently has 234 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Maintainable about?
Do you feel like you're hitting a wall with your existing software projects? Are you curious to hear how other people are navigating this? You're not alone.On the Maintainable Software Podcast, Robby speaks with seasoned practitioners who have overcome the technical and cultural problems often...
How often does Maintainable release new episodes?
Maintainable publishes regularly with 234 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Maintainable?
You can listen to Maintainable on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Maintainable?
Maintainable is created and hosted by Robby Russell.
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