Best Robbie Wagner Podcasts (2025)

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Taylor Otwell: What 14 Years of Laravel Taught Me About Maintainability 55:56

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4d ago55:56

55:56

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 maintainability, developer experience, and what it me…

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Sara Jackson: Why Resilience Is a Team Sport 53:06

1M ago53:06

53:06

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 Engineering at the application layer can help make the cas…

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Joel Chippindale: Why High-Quality Software Isn’t About Developer Skill Alone 56:39

2M ago56:39

56:39

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 Unmade and his current coaching practice, Joel outlines …

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Melanie Sumner: Why Continuous Accessibility Is a Strategic Advantage 49:30

3M ago49:30

49:30

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 change. Melanie shares her work making Ember.js more…

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Joe Masilotti: Simplify Your Stack, Ship Mobile Sooner 55:42

3M ago55:42

55:42

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 scripts often add unnecessary complexity, and how he eva…

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Freedom Dumlao: What 70 Java Services Taught Me About Focus 1:03:19

4M ago1:03:19

1:03:19

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 assets. But what’s most surprising? His story of how a t…

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Mercedes Bernard: Friendly Code Welcomes Everyone In 49:27

5M ago49:27

49:27

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 debt, and creating a team culture that values maintai…

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Evan Phoenix: The Why of the One Line 1:09:13

5M ago1:09:13

1:09:13

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 from artists and tradespeople alike. Episode Highlights…

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Chris Salvato: Building Developer Paradise by Sitting in the Problem Space 46:31

5M ago46:31

46:31

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 immediately into controllers and tests, he begins by talkin…

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Heimir Thor Sverrisson: Architecture First, Tech Debt Second 40:58

6M ago40:58

40:58

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, tackling technical debt, and solving large-scale perf…

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Noémi Ványi: Only Fix Problems That Are Actually Problems 42:01

6M ago42:01

42:01

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, how product teams and developers can work better tog…

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Julia López: Code Tells a Story—Even the White Spaces 50:32

6M ago50:32

50:32

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 refactoring and how a strong engineering culture can mak…

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Marty Haught: Rethinking Technical Debt—Is It Really Just Drift? 52:39

6M ago52:39

52:39

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 software with its evolving purpose over time. They also dig …

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Mike Bowers - From ISAM to JSON—Navigating 40+ Years of Database Evolution 44:46

7M ago44:46

44:46

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 debt. Mike shares how FairCom transitioned from ISAM-b…

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Lorna Mitchell: Writing Documentation Engineers Will Actually Read 43:18

7M ago43:18

43:18

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 in developer experience. Highlights: What Makes Soft…

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Carola Lilienthal: Tackling Technical Debt with Patterns and Domain Knowledge 43:00

7M ago43:00

43:00

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, and domain knowledge are crucial for maintainability…

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Joel Hawksley: The Hidden Costs of Frontend Complexity 46:13

8M ago46:13

46:13

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: GitHub’s design system and the paradox of its success…

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Austin Story: Making Software Easier to Change, Remove, and Evolve 47:08

9M ago47:08

47:08

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 architecture to a federated model, why simplicity matters …

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Dan Moore: Building Developer-Friendly Authentication Solutions 49:20

9M ago49:20

49:20

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 codebases. Working with Legacy Systems Dan shares stori…

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Tom Johnson: From Auto-Documentation to Better Collaboration 43:19

9M ago43:19

43:19

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. Topics Discussed Characteristics of well-maintained softw…

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Gulcin Yildirim Jelinek: Maintaining Postgres for Modern Workloads 38:18

9M ago38:18

38:18

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. Gulcin shares practical insights into modern database…

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Justine Gehring: Refactoring Software at Scale with AI 48:07

10M ago48:07

48:07

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 semantic trees, and discuss how developers can benefit …

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Katerina Skroumpelou: Bridging Engineering and Advocacy for Scalable Software 36:48

10M ago36:48

36:48

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 [00:01:25] Katerina’s Background: Robby and Katerina dis…

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Moriel Schottlender: The Challenges of Modernizing MediaWiki's Monolith 46:10

10M ago46:10

46:10

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 insights on what it takes to keep an enormous monolith…

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Kate Holterhoff: From Front-End Engineering to Developer Advocacy 51:55

11M ago51:55

51:55

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 from her time as a practitioner at a digital marketi…

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Alan Ridlehoover: Building Robust Systems Through Behavior-Centric Testing 48:27

11M ago48:27

48:27

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, clear code ownership, and thoughtful technical decisions…

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April Wensel: Navigating Legacy Code with Compassion 52:05

11M ago52:05

52:05

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 legacy code, mentoring junior developers, and address…

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Saron Yitbarek: The Balance Between Maintainable Code and Multiple Streams of Income 41:20

11M ago41:20

41:20

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 first teammate and the lessons learned along the way abo…

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Lutz Hühnken: Crafting Resilient Systems with Event-Driven Design 44:45

12M ago44:45

44:45

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 systems into manageable modules and leveraging event-driv…

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Noel Rappin: Reviving the Pickaxe— A Journey through Ruby's Legacy 43:58

12M ago43:58

43:58

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 legacy technical book and the lessons learned along the w…

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Cassidy Williams: Navigating the Career Jungle Gym in Tech 43:18

1y ago43:18

43:18

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 by discussing what makes software truly maintainable—…

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Obie Fernandez: Pioneering AI in Ruby on Rails Development 44:11

1y ago44:11

44:11

In this episode of the Maintainable Software Podcast, Robby speaks with Obie Fernandez, Chief Scientist at Olympia, about the integration of AI into modern software development. Obie shares his unique perspective on leveraging AI to enhance the maintainability and functionality of software applications, particularly in the Ruby on Rails ecosystem. …

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Tekin Süleyman: Balancing Complexity and Team Size 42:31

1y ago42:31

42:31

Topics Discussed Characteristics of Well-Maintained Software: Tekin emphasizes the importance of software that is easy to change and tailored to the team's needs. Balancing Complexity and Team Size: Tekin discusses how his small team manages complexity and features to maintain sustainable work practices without overburdening the developers. GovUK P…

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Ryosuke Iwanaga: The Benefits of Cell-Based Architecture 42:26

1y ago42:26

42:26

Ryosuke shares his insights on: Ownership in Software Maintenance: The role of single-threaded ownership and dedicated teams in maintaining software and shared libraries. Technical Debt: How his definition of technical debt has evolved over the years and strategies to manage it effectively. Monitoring and Alarming: The importance of comprehensive m…

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Julia Ferraioli - Capturing Untold Open Source Stories 47:32

1y ago47:32

47:32

Welcome to the Maintainable Software Podcast! In this episode, Robby speaks with Julia Ferraioli, an Open Source AI/ML Strategist at AWS and co-founder of Open Source Stories. Julia joins us from Seattle, Washington, and shares her insights into the world of open source, AI, and software maintainability. Key Topics: Well-Maintained Software: Julia …

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Tanmai Gopal: Unlocking the Potential of Unified APIs 44:39

1y ago44:39

44:39

In this episode of Maintainable, Robby Russell sits down with Tanmai Gopal, the CEO and co-founder of Hasura. Tanmai shares his insights into the characteristics of well-maintained software and the importance of a codebase that no team member fears. He emphasizes the need for accessibility and understandability in code, making it easier for develop…

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James Socol: Building Social Capital in Engineering Teams 44:18

1y ago44:18

44:18

In this episode of the Maintainable Software Podcast, Robby Russell sits down with James Socol, a Staff Engineer at Fastly, to discuss the art of maintaining legacy code and the nuances of technical debt versus technical depreciation. Key Topics Discussed: Characteristics of Well-Maintained Code: James shares his insights on what defines well-maint…

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Paola Ducolin: Building Trust and Communication in Engineering Teams 45:30

1y ago45:30

45:30

In this episode of Maintainable, Robby chats with Paola Ducolin, Staff Engineer at Datadog. Paola shares her insights on the characteristics of well-maintained software, the common struggles teams face, and effective strategies for working with stakeholders to prioritize refactoring. Key Topics Discussed: Characteristics of Maintainable Software: P…

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Robin Heinze - React Native and the Art of Flexibility 40:35

1y ago40:35

40:35

In this episode, Robby welcomes Robin Heinze, Director of Engineering at Infinite Red, to discuss the intricacies of building and maintaining robust software systems. Key topics covered include: Characteristics of Maintainable Software: Robin shares insights from her team on what makes software maintainable, emphasizing the need for clear documenta…

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Scott Hanselman - The Fear Factor in Maintainable Software 36:35

1y ago36:35

36:35

In this episode of Maintainable, Robby welcomes Scott Hanselman, VP of Developer Community at Microsoft and host of the Hanselminutes Podcast, to discuss the emotional side of maintainable software. Scott shares his thoughts on fear as a common thread in poorly maintained software, the importance of building a team culture of trust, and how finding…

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Stig Brautaset: Understanding Alien Artifacts in Legacy Code 46:04

1y ago46:04

46:04

In this episode of Maintainable, Robby chats with Stig Brautaset, Staff Software Engineer at CircleCI. Stig shares his insights on maintaining well-documented but complex legacy code, the impact of team dynamics on software maintenance, and his experiences with the SBJSON library. Stig discusses the characteristics of well-maintained software, emph…

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Brit Myers - Decoding Product vs. Technical Risk 42:20

1+ y ago42:20

42:20

Join Robby as he welcomes Brit Myers to the podcast. Brit, currently thriving as the VP of Engineering at System Initiative, discusses the intricacies of maintaining software. She emphasizes the importance of navigable software, where the ease of tracing the code and understanding its structure is paramount. Brit highlights the significance of clea…

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Andrea Guarino - Leveraging Static Analysis for Better Code 36:18

1+ y ago36:18

36:18

In this episode, Robby interviews Andrea Guarino, a Software Engineer at Sonar, about the importance of leveraging static analysis tools for maintaining clean and adaptable code. Andrea emphasizes that well-maintained software should be easy to change, consistent, intentional, and responsible. He explains that static analysis tools play a crucial r…

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Staffan Nöteberg - On the Power of Monotasking in Software Development 46:54

1+ y ago46:54

46:54

In this insightful episode, we dive deep into the essence of software maintainability with Agile Coach and author Staffan Nöteberg. Unpacking the layers of what it takes for software to be considered well-maintained, Staffan sheds light on the crucial roles of abstraction and modularity. These foundational elements not only make software easier to …

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Martin Emde - Ruby Central and the Art of Being Tolerant to Change 52:47

1+ y ago52:47

52:47

In this episode of Maintainable, our host Robby Russell sits down with Martin Emde, a sage in the Ruby community and the current Director of Open Source at Ruby Central. Together, they weave through the intricacies of maintainable software, legacy code, and the unwavering power of the Ruby ecosystem. Martin, with his wealth of experience, shares ta…

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Esther Olatunde - AI's Role in Evolving Software Engineering Practices 47:39

1+ y ago47:39

47:39

In this captivating episode of the Maintainable Software Podcast, host Robby Russell delves deep with Esther Olatunde, Senior Product Engineer at Intercom, into the realms of software maintenance, technical debt, and the impact of AI on software development. The discussion kicks off with Esther's insights on what constitutes well-maintained softwar…

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Robbie Wagner - Whiskey, Front-End, and Whatnot 40:02

1+ y ago40:02

40:02

Starting off, Robbie Russell and Robbie Wagner bonding over the complexities of their names in the coffee queue. They dive into the essence of maintainable software, debating the importance of recent commits and the dangers of a single-contributor project. Tech debt, the ever-looming shadow over software development, gets a moment in the spotlight.…

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Irina Nazarova - Investing in Innovation: The Consultancy's Guide to Growth 45:48

1+ y ago45:48

45:48

In the latest episode of Maintainable, Robby Russell has a fascinating conversation with Irina Nazarova, the CEO of Evil Martians, a name that resonates with innovation and bold strides in the software development world. They dive deep into what it takes to maintain not just code, but also the delicate balance between rapid development and long-ter…

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Kyle Daigle - Scaling Up with AI: A New Era of Code Maintenance 47:19

1+ y ago47:19

47:19

Robby has a chat with Kyle Daigle, the Chief Operating Officer at GitHub. They dive into the evolution of software development from the perspective of maintaining and scaling software within large organizations like GitHub. Kyle talks about the importance of simplicity and readability in code over complexity, advocating for well-named variables and…

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Jon Moniaci - Can We Draw A Boundary? 53:48

1+ y ago53:48

53:48

Robby speaks to the Senior Software Engineer at Perchwell, Jon Moniaci. They discuss the delicate balance between innovation and stability in software development. Jon emphasizes the importance of fostering an environment where engineers can experiment without fear, advocating for a culture of defensive programming to mitigate the fear of breaking …