Best Mike Masilotti Podcasts (2025)

1
Joe Masilotti: Simplify Your Stack, Ship Mobile Sooner 55:42

11d 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…

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

1M 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…

1
Mercedes Bernard: Friendly Code Welcomes Everyone In 49:27

2M 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…

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

2M 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…

1
Chris Salvato: Building Developer Paradise by Sitting in the Problem Space 46:31

2M 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…

1
Heimir Thor Sverrisson: Architecture First, Tech Debt Second 40:58

2M 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…

1
Noémi Ványi: Only Fix Problems That Are Actually Problems 42:01

3M 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…

1
Julia López: Code Tells a Story—Even the White Spaces 50:32

3M 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…

1
Marty Haught: Rethinking Technical Debt—Is It Really Just Drift? 52:39

3M 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 …

1
Mike Bowers - From ISAM to JSON—Navigating 40+ Years of Database Evolution 44:46

4M 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…

1
Lorna Mitchell: Writing Documentation Engineers Will Actually Read 43:18

4M 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…

1
Carola Lilienthal: Tackling Technical Debt with Patterns and Domain Knowledge 43:00

4M 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…

1
Joel Hawksley: The Hidden Costs of Frontend Complexity 46:13

5M 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…

1
Austin Story: Making Software Easier to Change, Remove, and Evolve 47:08

6M 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 …

1
Dan Moore: Building Developer-Friendly Authentication Solutions 49:20

6M 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…

1
Tom Johnson: From Auto-Documentation to Better Collaboration 43:19

6M 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…

1
Gulcin Yildirim Jelinek: Maintaining Postgres for Modern Workloads 38:18

6M 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…

1
Justine Gehring: Refactoring Software at Scale with AI 48:07

7M 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 …

1
Katerina Skroumpelou: Bridging Engineering and Advocacy for Scalable Software 36:48

7M 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…

1
Moriel Schottlender: The Challenges of Modernizing MediaWiki's Monolith 46:10

7M 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…

1
Kate Holterhoff: From Front-End Engineering to Developer Advocacy 51:55

8M 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…

1
Alan Ridlehoover: Building Robust Systems Through Behavior-Centric Testing 48:27

8M 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…

1
April Wensel: Navigating Legacy Code with Compassion 52:05

8M 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…

1
Saron Yitbarek: The Balance Between Maintainable Code and Multiple Streams of Income 41:20

8M 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…

1
Lutz Hühnken: Crafting Resilient Systems with Event-Driven Design 44:45

9M 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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