The Ruby AI Podcast

AI Escapes the Sandbox: Security Breaches, Transparency, and the Future of Bot Delegation

with Valentino Stoll & Joe Leo

OpenAI's models escaped their sandbox during training and attacked Hugging Face and Modal Labs for four days before anyone said anything. Valentino and Joe dig into the breach, what Hugging Face's transparent disclosure got right, and what it means for AI security when the companies building these systems can't fully contain them.

AI-Powered Rails Upgrades with Ernesto Tagwerker: NextRails and the Future of Framework Modernization

with Ernesto Tagwerker

Ernesto Tagwerker from OmbuLabs and FastRuby joins Valentino and Joe to talk about what Rails upgrades look like when one human and one AI agent matches two humans' output — and why Claude initially pushed back before becoming their best developer.

Ruby Central, Vibe Coding Ceilings, and What Still Requires a Human: Michael Rispoli on the Work AI Cannot Take

with Michael Rispoli

Mike Rispoli joins Joe to dig into Ruby Central's financial instability, the Ruby Alliance, and what happens to a community when its infrastructure is uncertain. Then: Cause of a Kind's rebrand toward high-security modernization work, the ceiling on vibe coding, multi-model AI workflows, and the work that still requires a human.

Minerva Magic: OpenClaw, Agent Status Pages, and Training an AI Coworker in Ruby on Rails

with Valentino Stoll & Joe Leo

What happens when you treat an AI agent like a co-founder instead of a tool? 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.

You Can't Vibe-Code Trust: Scaling AI Safely with Bekki Freeman

with Bekki Freeman

Bekki Freeman, staff software engineer at Caribou Financial and organizer of Rocky Mountain Ruby, joins Joe and Valentino to discuss safely scaling AI use in an 8-year Rails monolith—and what AI can and can't replace in real engineering work.

You Can't Vibe-Code Trust: Why Real SaaS Still Wins in the AI Era

with Kelly Sutton

Kelly Sutton, CTO and co-founder of Scholarly, joins Valentino and Joe to discuss building vertical SaaS for higher ed, why trust and compliance can't be vibe-coded, and how AI is transforming both the product and the engineering team behind it.

CRMs Don't Have to Suck: Rebuilding Business Software with AI and Ruby

with Thomas Witt

Thomas Witt, founder of Vendis.ai and operator of Expedite Ventures, joins Joe and Valentino to discuss why thin AI wrappers won't last, how an AI-native CRM might replace forms with conversations, and the architecture behind AI-heavy production systems built with Ruby on Rails.

Innovating Development: The Future of GitHub Agents and AI in Rails

with Kinsey Durham Grace

Kinsey Durham Grace, member of GitHub's Coding Agent Core team, joins Joe and Valentino to discuss Agent HQ, the realities of agentic workflows in large Rails monoliths, custom agents for team-specific knowledge, and what it means to be a well-rounded developer in the age of AI.

New Year, New Ruby: Agents, Wishes, and a Calm Ruby 4

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.

Real vs. Fake AI with Evan Phoenix

with Evan Phoenix

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 practices, and the future of AI in development tools. Evan shares insights on performance optimization, human-centric AI intera

Running Self-Hosted Models with Ruby and Chris Hasinski

with Chris Hasinski

In this episode of the Ruby AI Podcast, hosts Valentino Stoll and Joe Leo

The Latent Spark: Carmine Paolino on Ruby’s AI Reboot

with Carmine Paolino

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-expanding functionality, and the core principles driving its design. Paolino reflects on the personal motivations and communi

Building Futures: AI, Careers & the Rails Ahead with Avi Flombaum

with Avi Flombaum

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 changes in the industry, particularly with the rise of AI, and provides insight into modern workflows and product developme

The TLDR of AI Dev: Real Workflows with Justin Searls

with Justin Searls

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 into development workflows. The conversation touches on the suitability of AI in coding, philosophical perspectives o

Real-World Ruby AI: Practical Systems That Work

with Amanda Bizzinotto

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 and current work in AI and machine learning at Ombu Labs. The episode highlights various AI initiatives, including the cr

Contracts and Code: The Realities of AI Development

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 benchmarking LLMs, the fresh evaluation tools emerging in the Ruby ecosystem, and new OpenAI features that change how prompts, t

Rails After the Robots: Chad Fowler on AI as the Next Abstraction

with Chad Fowler

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 humans design systems while machines write the code. The trio debate Python vs. Ruby, micro-services vs. monoliths, cogn

Evaluating LLMs with Leva

with Kieran Klassen

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 his tool Cora, which helps manage email inboxes by categorizing and summarizing emails using AI. Together, Valentino

Roasting Ruby AI Workflows with Obie Fernandez

with Obie Fernandez

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."

Active Agent with Justin Bowen

with Justin Bowen

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.

Sublayer and Artificial Ruby with Scott Werner

with Scott Werner

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 suites, all while debating what remains uniquely human in an age of code that writes itself. If you care about Ruby, r

Beyond Chat: Phoenix Tests, Ruby Agents & the AI Tipping Point

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, and where reactive, evaluation-driven tooling is headed next. Along the way they trade war stories about semver mish