The Ruby AI Podcast

Send us Fan Mail When AI Refused to Listen and Then Became the Best Developer on the Team Rarely does a story about an AI tool actively resisting instructions end up being the most compelling argument for using that tool. When Claude initially pushed back against adding conditionals for dual booting large legacy Rails applications, the team at FastRuby had to essentially teach it their own hard-wo...

Send us Fan Mail Joe Leo hosts the Ruby AI Podcast with guest Mike Rispoli, discussing Ruby Central’s financial instability, leadership changes, the Ruby Alliance (including Gusto joining), and concerns about fragmentation in the Ruby ecosystem after RailsConf’s end and uncertainty around RubyConf. They compare governance models (benevolent dictator vs committees) and debate centralized package in...

Send us Fan Mail What happens when you treat an AI agent like a co-founder instead of a tool? In this episode, Valentino and Joe go deep into a real-world experiment: spinning up an autonomous agent using OpenClaw, giving it domains, goals, and just enough guidance to build an actual business. From creating accounts and managing projects to writing code, deploying with Kamal, and even designing it...

Send us Fan Mail Valentino Stoll and co-host Joe Leo open the Ruby Podcast noting OpenAI is winding down its SOA video app and discuss the broader difficulty of building AI businesses. Guest Bekki Freeman, staff software engineer at Caribou Financial and organizer of Rocky Mountain Ruby, shares conference details (Boulder, Colorado at eTown, September 28–29; CFP opening soon; tickets after the sch...

Send us Fan Mail On the Ruby AI Podcast, hosts Valentino and Joe Leo welcome Scholarly CTO/co-founder Kelly Sutton to discuss building a vertical SaaS “faculty information system” for universities. Sutton explains why competitors can’t easily replicate Scholarly: higher ed is moving off decades-old homegrown software, and the product must meet trust, security, compliance, and regulatory demands su...

Send us Fan Mail Many “AI startups” today are little more than thin wrappers around large language model APIs. But what happens when those APIs improve and the platforms absorb those features? In this episode of The Ruby AI Podcast , Valentino Stoll and Joe talk with builder and investor Thomas Witt , founder of Vendis.ai and operator of the pre-seed firm Expedite Ventures. Thomas shares why he be...

Send us Fan Mail In this episode of the Ruby AI Podcast, hosts Joe and Valentino welcome special guest, Kinsey Durham Grace, a prominent figure in the Ruby community and member of the GitHub team. The discussion covers a range of topics including the use of AI for generating episode artwork, the application of AI agents in coding tasks, and the recent developments at GitHub like the Agent HQ. Kins...

Send us Fan Mail In this episode of the Ruby AI Podcast, hosts Valentino Stoll and Joe Leo are joined by Ben Schofield, an accomplished author, open source contributor, and Ruby enthusiast. The discussion starts with thoughts on the upcoming RubyConf and the unique experience of conferences hosted in Las Vegas. Ben shares his recent experiences with Bento and the impact of layoffs. The conversatio...

Send us Fan Mail Ruby turns 30, Ruby 4 quietly ships, and the AI tooling arms race shows signs of maturity. Valentino and Joe unpack what stability really means for a language in its third decade, debate agent-driven development, AI “slop,” binary distribution, and whether open source incentives are breaking down—or simply evolving. Mentioned In The Show A grab-bag of tools, projects, and referenc...

Send us Fan Mail In this episode of the Ruby AI podcast, hosts Valentino Stoll and Joe Leo engage with Evan Phoenix, a seasoned Ruby programmer and CEO of Mirren. The conversation explores Evan's unique name origin, his career trajectory, and the integration of AI in development workflows. They discuss the distinction between real and fake AI in products, the impact of AI on engineering pract...

Send us Fan Mail In this episode of the Ruby AI Podcast, hosts Valentino Stoll and Joe Leo welcome AI and Ruby expert Chris Hasinski. They delve into the benefits and challenges of self-hosting AI models, including control over model updates, cost considerations, and the ability to fine-tune models. Chris shares his journey from machine learning at UC Davis to his extensive work in AI and Ruby, to...

Send us Fan Mail In this episode of the Ruby AI Podcast, hosts Joe Leo and his co-host interview Carmine Paolino, the developer behind Ruby LLM. The discussion covers the significant strides and rapid adoption of Ruby LLM since its release, rooted in Paolino's philosophy of building simple, effective, and adaptable tools. The podcast delves into the nuances of upgrading Ruby LLM, its ever-exp...

Send us Fan Mail In this episode of the Ruby AI Podcast, hosts Valentino Stoll and Joe Leo are joined by Avi Flombaum, the founder of Flatiron School. Avi talks about the origins of Flatiron, the success it achieved, and the educational methods used to teach programming, emphasizing on the importance of understanding code deeply and leveraging AI efficiently. He discusses the challenges and change...

Send us Fan Mail In this episode of the Ruby AI Podcast, co-hosts Valentino Stoll and Joe Leo engage in a lively discussion with guest Justin Searls. They explore the evolving landscape of software development with agentic AI tools, comparing traditional agile methodologies with emerging AI-driven practices. Justin Searls his experiences with refactoring and the challenges of integrating AI tools...

Send us Fan Mail In this episode of the Ruby AI Podcast, co-hosts Joe Leo and Valentino Stoll, alongside guest Amanda Bizzinotto from Ombu Labs, delve into the ongoing controversy within the Ruby community involving Ruby Central, Shopify, and Bundler/Ruby Gems. While both Valentino and Amanda share their perspectives on the situation, the conversation swiftly transitions into Amanda's journey...

Send us Fan Mail In this episode, Valentino Stoll and Joe Leo unpack the widening gap between headline-grabbing AI salaries and the day-to-day realities of building sustainable AI products. From sports-style contracts stuffed with equity to the true cost of running large models, they explore why incremental gains often matter more than hype. The conversation dives into the messy art of benchmarkin...

Send us Fan Mail Veteran Rubyist and investor Chad Fowler sits down with hosts Valentino Stoll and Joe Leo to unpack why generative AI is less a magic trick and more the next big layer of abstraction. From his days rewriting Wunderlist in multiple languages to today’s LLM-driven code generation, Chad explains how small, well-typed modules, strong conventions and agent-based workflows could let hum...

Send us Fan Mail In this episode of the Ruby AI Podcast, host Valentino Stoll talks with special guest Kieran, a prominent figure in the Ruby AI space. Kieran recently gave a talk at the San Francisco Ruby Meetup about his new gem, Leva, which focuses on LLM evaluations in Ruby. Kieran discusses his background, his passion for AI and Ruby, as well as his journey in building AI products, including...

Send us Fan Mail Ruby legend Obie Fernandez joins hosts Valentino Stoll and Joe Leo to unveil Roast—the new open-source Ruby framework for declaring reliable AI workflows—and celebrate the 1.0 release of its engine library, Raix. The trio dig into agent swarms, prompt-engineering best practices, code-base refactors, and why unleashing creativity matters more than ever in an AI-driven future."...

Send us Fan Mail Seventeen-year Ruby veteran Justin Bowen joins hosts Valentino Stoll and Joe Leo to unveil Active Agent —a Rails-native framework that treats every agent like a controller and every prompt like a view, letting you weave LLMs, vector search, and business logic straight into MVC. The crew also digs into the real-world mechanics of shipping AI: defining ground-truth datasets, replay-...

Send us Fan Mail Scott Werner—author of the Works on My Machine newsletter and creator of the Sublayer AI-agent framework—joins Valentino and Joe for a fast-moving conversation on how Rubyists are bending large-language models to their will. We unpack Sublayer’s “generators + actions” architecture, the delightfully chaotic Monkey’s Paw prompt-driven web framework, and Phoenix’s AI-generated test s...

Send us Fan Mail Valentino Stoll and co-host Joe Leo kick off The Ruby AI Podcast with a candid deep-dive into what it really takes to ship AI-powered products in Ruby today. From the origin story of Joe’s test-writing automation platform Phoenix to the surge of new Ruby-first agent libraries, the duo explore why the community is approaching a tipping point, how to escape “chat-bot-only” thinking,...

Send us Fan Mail In this episode of the Ruby AI podcast, hosts Landon and Valentino discuss the exciting developments in the Ruby AI community. They explore three key gems: Ruby OpenAI, Raix, and Langchain.rb, highlighting their features, use cases, and the importance of evaluation methodologies like RAGAS in AI systems. The conversation emphasizes the collaborative spirit of the Ruby AI community...