In this episode, Kyle Keesling, co-owner of PASS Testing and long-time solo Rails developer, shares how PASS grew from a college web design side project into a niche software and training business for the Underground Storage Tank (UST) industry. The conversation covers why they kept the products as two apps connected by a read-only private API, what makes compliance software hard, and how they modeled flexible equipment and inspection data—evolving from STI to Rails delegated types. Kyle also discusses early scaling pains around billing and payments, how feature requests are prioritized with help from their CRO and a contractor, and how tools like Claude Code are changing his workflow while maintaining PR-based review and safer deployment practices.

00:00 Meet Kyle Keesling& His Role at PASS Testing
00:29 From College Web Design to a Niche Opportunity in UST Compliance
02:31 Building Opus: A Custom LMS for Gas Station Training
03:34 Why Compliance Is Hard: 50 States, 50 Rulebooks
04:25 From Training to Past Tools: The Second Product Idea
08:06 Two Apps or One? Data Sync, APIs, and Customer Workflows
10:25 Would He Do It Again? Decoupling, Upgrades, and Acquisition Optionality
12:28 Why Past Tools Is More Complex: Data-Driven Inspections & Asset Inventory
16:13 Modeling the Domain in Rails: STI → Delegated Types (and Migration Strategy)
22:35 Versioning & “Point-in-Time” Inspections: Preventing Old Reports from Changing
24:13 Downtime, SLAs, and Recovering from Form/Data Bugs
26:40 Early Scaling Stories: Hardcoding States and Billing Growing Pains
29:39 Letting Customers Shape the Product (Beyond Compliance)
31:14 Integrations vs. Building Everything In-House
32:50 Feature Requests, Backlog Triage, and Adding Sales/Dev Bandwidth
37:41 Shipping Without the Never-Ending PR: Iterative Rollouts ("Visits")
40:39 Using AI Safely: PRs, Branch Protections, and Documentation Habits
46:14 Wrap-Up: Where to Find Kyle and Past Testing

LINKS

- PASS Testing

- Kyle's X/Twitter

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

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In this episode, the hosts reconnect after a holiday break to reflect on their podcast journey over the last year. They discuss important milestones like their one-year recording anniversary, the various episodes from the past year, and sharing their favorite moments.

00:00 Introduction and New Year Greetings
00:34 Reflecting on the First Year of Podcasting
01:57 Memorable Moments and Guest Highlights
03:51 Popular Episodes and Themes
06:38 Looking Forward: Future Topics and Guests
07:42 Balancing Guests and Solo Episodes
09:15 Podcast Growth and Marketing Insights
10:16 Commitment to Consistency and Goals
12:18 Exploring Business and Technical Challenges
27:46 Concluding Thoughts and Call for Guests

LINKS

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

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In this episode, the hosts discuss reflect on the high-quality, maintainable code found in various videos and books and their own aspirations to emulate such coding standards. The conversation covers the challenges of maintaining good coding practices over time and under business pressures. They explore the concept of 'good enough' code based on the maturity stage of a business, and debate how AI impacts coding quality. The hosts consider how AI can assist in writing tests, potential pitfalls, and the complexity of integrating AI into development while maintaining high standards. Lastly, they touch upon the concept of agentic coding and the importance of well-defined code boundaries in future development strategies.

00:00 Introduction and Catching Up
00:34 Exciting News from 37 Signals
02:11 The Urge for Clean Code
03:33 Challenges in Maintaining Code Quality
06:45 Reflections on Code Quality and Team Dynamics
16:12 The Role of AI in Coding
18:18 AI's Role in Code Architecture
18:33 AI in Controller and View Design
19:42 AI's Limitations in High-Level Decisions
21:13 Using AI for Writing Code and Tests
25:09 The Future of AI in Code Readability
29:49 Challenges and Hypotheses in AI-Driven Development
33:54 Final Thoughts and Future Topics

LINKS

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

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In this episode, we chat with Mateus Pereira from Ombu Labs about the nuances of Rails upgrades and how AI is revolutionizing the process. From tackling gem dependencies to client collaboration, Mateus shares valuable insights and tips for executing seamless upgrades. Perfect for developers looking to streamline their Rails projects and leverage AI tools effectively.

00:00 Introduction and Casual Chat
00:25 Meet Mateus: Senior Rails Engineer
01:29 Mateus' Journey into Programming
02:17 Joining Ombu Labs: Trials and Triumphs
03:33 Lessons from Rejection and Persistence
04:35 Challenges in Rails Upgrades
08:12 Tackling Gem Dependencies
20:04 The Role of AI in Rails Upgrades
30:47 Discussing Ruby Critic and Rails Bump
32:07 AI in Code Refactoring
33:58 Client Relationships and Project Management
44:14 Challenges with Test Coverage
45:32 Manual Testing and QA Processes
49:18 Using AI for Writing Tests
55:37 Final Thoughts and Sign-Off

LINKS

- Mateus' Blog

- Mateus' X/Twitter

- Mateus' LinkedIn

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

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In this episode, Nate Berkopec, the proprietor of Speedshop, a Ruby on Rails performance consultancy, author of several books including the Complete Guide to Rails Performance, and a maintainer of Puma, joins the podcast. Nate discusses his journey into Rails performance optimization, starting from his early career at startups and his breakthrough talk at the Gotham Ruby Conference. He outlines his 'Three S' framework—Speed, Scalability, and Stability—for tackling performance issues. The discussion includes practical advice for Heroku users on optimizing 'dynos' for better request queuing and performance, as well as insights on using tools like JudoScale and PG Analyze for better Sidekiq job management and database optimization. Nate also touches on the importance of setting proper performance thresholds to balance system efficiency and operational costs.

00:00 Introduction to Nate Berkopec and Speedshop
00:45 Nate's Early Career and Interest in Performance
03:36 The Impact of Nate's Conference Talk and Book
04:40 Challenges in Diagnosing Performance Issues
10:22 Framework for Tackling Performance Problems
17:27 Understanding Heroku's Load Balancing
27:39 Understanding TCP Open Failures
28:10 Optimizing Dynos on Heroku
29:16 Setting Performance Thresholds
31:12 The Importance of Monitoring and Automation
34:25 Challenges with Sidekiq and Data Processing
36:24 Best Practices for Sidekiq Queues
44:48 Ensuring Job Idempotency and Efficiency
49:26 Rapid Fire Tips for Indies
52:41 Conclusion and Final Thoughts

LINKS

- Speedshop

- Nate's X/Twitter

- The Complete Guide to Rails Performance Book

- Sidekiq in Practice Book

- High Availabillity Wikipedia Article

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

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In this episode, we tackle the nuances of communicating project requirements within development teams. From managing user stories and acceptance criteria to balancing control and flexibility, we explore best practices for ensuring clarity and efficiency. We share real-world experiences, including the effectiveness of detailed videos and spikes in guiding team members. 

01:24 Communicating with Different Levels of Expertise
06:06 The Role of Videos in Communication
14:45 Challenges in Estimating and Scoping Projects
30:52 Using AI to Assist in Writing Tickets

LINKS

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

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 In this episode, we welcome Stephen Anderson, founder and owner of Bendyworks, a Madison, Wisconsin based Ruby on Rails consultancy. Stephen shares his journey from corporate Java consulting to building a values-driven software shop, discussing his philosophy of constantly seeking 10x productivity improvements and the pivotal moments that led him to entrepreneurship. 

LINKS

- Bendyworks

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

Send us a text

In this episode, we welcome Scott Werner, CEO of Sublayer, to discuss the future of software development and how AI is transforming the industry. Scott shares his experiences and insights on how AI is changing the way startups build and maintain software products, including Sublayer’s AI-driven tools like APM, Augmentations, and Artificial Ruby. They explore practical applications of AI in software engineering, the concept of MCP, and the fast-evolving landscape of AI technology, offering valuable takeaways for developers and tech entrepreneurs.

00:20 Overview of Sublayer's AI Focus
01:20 Main Products and Innovations
03:29 AI in Software Development
07:00 Triggers and AI Automation
08:58 MCP and Structured Outputs
17:53 Open Source and AI Agents
20:05 The Future of AI in Development
21:15 Journey to Sublayer: A Winding Road
23:10 Challenges and Innovations in AI Product Development
28:09 The Fast Fashion Era of Software
33:14 The Future of AI and Business Models
40:17 Concluding Thoughts and Future Plans

LINKS

- Sublayer Website

- Scott's Blog (Works on My Machine)

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

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This week, Chris Gaffney, owner of Dead Man's Snitch, a niche monitoring service for CRON jobs and service heartbeats joined us. Discover the origins of the company, its growth journey, and the challenges faced in achieving uptime and scalability. Chris also shares insights on the tech stack used, the role of Rails in their development, and the impact of market strategies like Heroku integration.

00:00 Introduction and Guest Welcome
00:21 Overview of Dead Man's Snitch
03:03 Challenges and Achievements
03:49 Current Focus and Full-Time Commitment
04:12 Product Use Cases and Platforms
10:02 Heroku Integration Experience
16:09 Marketing Strategies and Developer Challenges
19:26 Future Plans and Dreams
20:08 Balancing Business and Family
23:56 The Value of Personal Touch in Business
25:40 Technical Challenges and Solutions
31:38 Data Management Strategies
37:19 The Role of Rails in Business Success
39:37 Conclusion and Contact Information

Questions or comments, email us at [email protected]

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In this episode, we explore how AI can be leveraged to build engaging features in our applications. We discuss the development of a 'guided blogging' feature using AI, its benefits for users, and the challenges faced in implementing conversational interfaces. We also discuss a bit about the future of AI in SaaS, the role of AI in content curation, and how to balance automation with human oversight.

00:00 Introduction and Catching Up
00:41 Discussing AI feature Ryan is building
02:35 Technical Challenges and Solutions
05:49 Exploring AI Integration
14:41 Future of AI in SaaS
25:13 Human Element in AI
31:42 Conclusion and Final Thoughts

LINKS

- Ryan's Website

- Brendan's X/Twitter

- Brendan's Bluesky

Questions or comments, email us at [email protected]

Send us a text