A podcast exploring exceptional products, how they're tested, and other stories from the testing community. How It's Tested is hosted by Eden Full Goh, Founder and CEO of Mobot.

How It's Tested

A podcast exploring the intersection of infrastructure and artificial intelligence, hosted by Rachel Chalmers.

Generationship

Exploring the evolution of open source software and its impact on the Tech landscape.

Open Source Ready

The podcast for leaders in software development to talk about the future of SaaS.

Platform Builders

In episode 36 of o11ycast, Charity and Liz speak with Jacob Scott of Stripe about the need for SRE teams, prioritizing customer happiness, and the limitations of distributed tracing tools.

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o11ycast - Ep. #36, Resilience Engineering with Jacob Scott of Stripe

In episode 57 of o11ycast, Jess and Martin speak with Shahar Azulay of Groundcover about monitoring Kubernetes applications, improving the UI experience of observability tools, and utilizing APMs. Shahar shares lessons learned from his storied career in R&D leadership positions, cyber security, machine learning and AI, as well as general advice for developers, SREs, project leaders, and executives.

o11ycast - Ep. #57, Monitoring K8s Applications with Shahar Azulay of Groundcover

In episode 59 of o11ycast, Jess and Martin speak with Laura Maguire of Jeli and Nick Travaglini of Honeycomb. They unpack Learning From Incidents (LFI), resilience engineering, process tracing, safety science, and the human side of observability.

o11ycast - Ep. #59, Learning From Incidents with Laura Maguire of Jeli

In this debut episode of How It’s Tested, Eden Full Goh of Mobot speaks with Ian Brillembourg of Plunk. Together they explore product testing processes, insights on utilizing AI-driven data as part of quality assurance, and lessons on striking a balance between web teams and mobile teams within a modern organization.

How It's Tested - Ep. #1, A Closer Look at Product Testing with Ian Brillembourg of Plunk

In episode 60 of o11ycast, Jess and Martin speak with Todd Gardner of TrackJS and Winston Hearn of Honeycomb. This talk explores customer-centric observability, Request Metrics, Core Web Vitals, and insights on optimizing observability across different browsers.

o11ycast - Ep. #60, Customer-Centric Observability with Todd Gardner and Winston Hearn

In episode 2 of How It’s Tested, Eden Full Goh speaks with Daniel Knott. They discuss trends in mobile testing tools, testing strategies for mobile clients, how mobile testing differs from broad software testing, and insights on advocating for mobile QA in the testing community.

How It's Tested - Ep. #2, Challenges in Mobile Testing with Daniel Knott

In episode 3 of How It’s Tested, Eden speaks with Alan Page. The conversation begins by exploring why developers should own the vast majority of testing automation. Alan also shares insights on balancing automated and manual testing and even shares lessons learned from his time testing products at Microsoft. As the conversation winds down, Eden and Alan discuss what makes a test case worth automating.

How It's Tested - Ep. #3, Balancing the Ownership of Testing with Alan Page

In episode 4 of How It’s Tested, Eden Full Goh speaks with testing expert Jacob Stevens. Together they unpack session-based testing and how it compares to regression testing. They also share insights on managing customer satisfaction, keeping up with rapidly evolving technology, and understanding the key differences between automated and manual testing.

How It's Tested - Ep. #4, Session-Based Testing with Jacob Stevens

In episode 5 of How It’s Tested, Eden Full Goh speaks with Filip Grebowski. This conversation explores Filip’s career journey, metrics for gauging the health of a product, insights on parsing vanity metrics from useful metrics, AI and content creation, and the future of developer advocacy.

How It's Tested - Ep. #5, The Future of Developer Advocacy with Filip Grebowski

Generationship is a podcast exploring the intersection of infrastructure and artificial intelligence through a technical and philosophical lens. In this debut episode, host Rachel Chalmers is joined by special guest Catharine Strauss of Summerstir Solutions. Together they dive deep into the world of infrastructure capacity planning, sustainability in data centers, the future of AI in the industry, the importance of getting outdoors, and much more.

Generationship - Ep. #1, Building Future Infrastructure Sustainably with Catharine Strauss

In episode 2 of Generationship, Rachel Chalmers speaks with Liz Fong-Jones and Phillip Carter of Honeycomb. Together they explore use cases for LLMs, insights on navigating AI hallucinations, the tradeoffs between fine-tuning and prompt engineering, and the privacy and security implications inherent to commercial LLMs.

Generationship - Ep. #2, Putting LLMs to Work with Liz Fong-Jones and Phillip Carter of Honeycomb

In episode 3 of Generationship, Rachel speaks with Steven Schkolne of MightyMeld. They discuss cultural myths surrounding AGI, theories on machine consciousness, philosophical insights on how humans might hybridize with machines, Steven’s literary influences, and how generative AI is helping humans advance their creative abilities.

Generationship - Ep. #3, A Contrarian History of AI with Steven Schkolne of MightyMeld

In episode 4 of Generationship, Rachel speaks with Michael Sawka of Wave Terminal (known as Command Line Inc. at the time of this recording). This talk focuses on the terminal, how easily it’s overlooked, and what’s missing from the terminals we use today. Other topics explored include the security implications of commercial LLMs, the risks AI poses to programming as an occupation, and the hard lessons Michael learned on the journey to building Wave Terminal.

Generationship - Ep. #4, Reimagining The Terminal with Michael Sawka of Wave Terminal

In episode 5 of Generationship, Rachel shares interviews from Heavybit’s 2023 DevGuild: AI Summit on October 19th, 2023. This Open Space unconference brought together a community of 200+ to discuss how AI will change the face of software development.

This episode features event highlights and insights from industry experts: Christine Spang of Nylas, Heidi Waterhouse of Sym, Paul Biggar of DarkLang, Raiya Kind of Code and Concept, and Seema Patel of Stifel Venture Banking.

Generationship - Ep. #5, Live from DevGuild: AI Summit

In this inaugural episode of Open Source Ready, Brian Douglas and John McBride embark on a technical and philosophical exploration of the current state of open-source AI. John shares his hands-on experience with building large-scale data pipelines and integrating AI to create meaningful insights for developers. The discussion revolves around the balance between innovation, data privacy, and the growing power of large tech companies in the AI space. They also touch on the open-source community's challenges, including licensing issues and the role of foundations in supporting AI projects.

Open Source Ready - Ep. #1, Introducing Open Source Ready

In episode 2 of Open Source Ready, Brian Douglas and John McBride speak with Avi Press, Founder & CEO of Scarf. Together they explore the evolving definition of "open source" in the context of AI and the future of technology. They also examine broader issues surrounding licensing, business models in open source, and the challenges associated with both.

Open Source Ready - Ep. #2, Defining Open Source with Avi Press of Scarf

In episode 3 of Open Source Ready, Brian and John sit down with Chad Whitacre from Sentry to discuss the Open Source Pledge, a new initiative aimed at addressing the sustainability crisis in open source software. Chad shares insights on how companies can better support the maintainers behind the projects they rely on and explores the cultural challenges of funding open source development.

Open Source Ready - Ep. #3, The Open Source Pledge with Chad Whitacre of Sentry

In episode 4 of Open Source Ready, Brian and John chat with open source expert Tobie Langel about the critical issues of sustainability and security in open source software. Tobie shares insights on the vulnerabilities of widely used open source projects, the need for professional maintainers, and the evolving legislative landscape that could reshape the future of open source.

Open Source Ready - Ep. #4, A Billion-Dollar Idea with Tobie Langel

In episode 5 of Open Source Ready, John and Brian speak with Elliott Minns, the creator of Dreams of Code and Dreams of Autonomy. They explore Elliott’s mission to empower developers through software autonomy, the challenges of open source sustainability, and the fascinating potential of Linux and NixOS. Discover how self-hosting and open source tools are transforming the way we interact with technology.

Open Source Ready - Ep. #5, Software Autonomy: Owning Your Tech with Elliott Minns

In this inaugural episode of Platform Builders, hosts Christine Spang and Isaac Nassimi of Nylas welcome Justin Belobaba, Founder and CEO of Nowsite. Justin shares his journey from finance to tech entrepreneurship and offers insights on the importance of failing fast, why startups must be willing to pivot, and how AI is shaping the future of solopreneurship. If you’re building a business—or just fascinated by the power of AI—you won’t want to miss this conversation.

Platform Builders - Ep. #1, The Future of CRM is No CRM with Justin Belobaba

Jesse Robbins interviews Sean Taylor about his work programming the Data Science & Algorithms track for Data Council 2025.

Data Council - Ep. #2, The Data Science & Algorithms Track with Sean Taylor and Jesse Robbins

In episode 2 of Platform Builders, Jamie Davidson, CEO of Vitally, joins Christine Spang and Isaac Nassimi to discuss the evolution of customer success platforms. They explore Vitally's journey from a customer data tool to a comprehensive platform, the strategic decisions behind product development and fundraising, and the impact of AI on the future of customer success. Davidson also shares insights on innovating customer engagement and building a platform that empowers both customer success teams and the wider business.

Platform Builders - Ep. #2, Charging Customers was a Mistake with Jamie Davidson

In this episode of Platform Builders, Christine Spang and Isaac Nassimi chat with Ben Rubin about the evolution of software development, from the early days of the internet to the current age of AI. They discuss the impact of AI on B2B SaaS, the challenges of building platforms in a rapidly changing landscape, and the future of user experience. Ben shares his experiences and insights on how developers and businesses can adapt to thrive in this new era.

Platform Builders - Ep. #3, Building Platforms in the AI Era with Ben Rubin of Verify

In episode 4 of Platform Builders, Christine Spang and Isaac Nassimi interview Ray Zhou, co-founder of Affinity, about his journey building the company, the evolution of the SaaS market, and the transformative potential of AI. Ray shares insights on scaling a business, the importance of focusing on the problem, and how SaaS companies can adapt to thrive in an AI-driven future.

Platform Builders - Ep. #4, Building Affinity: From College Dropout to SaaS Leader with Ray Zhou

In episode 5 of Platform Builders, Christine Spang and Isaac Nassimi chat with Scott Mitchell, former CTO of Salesloft, about the challenges and triumphs of scaling a high-growth B2B SaaS company. Scott shares his experiences navigating hyper-growth, from tackling critical infrastructure bottlenecks to fostering a culture of adaptability. They also explore the evolution of sales technology and the impact of AI on the future of sales engagement.

Platform Builders - Ep. #5, Maxed out on AWS, Still Falling Over with Scott Mitchell

In episode 80 of o11ycast, Ken Rimple and Jessica Kerr chat with Kent Beck about the emerging world of AI-assisted coding. Beck shares his experiences with "augmented coding," discussing the benefits, challenges, and the evolving relationship between developers and AI agents. They explore how these tools are changing software development practices and what it means for the future of coding.

o11ycast - Ep. #80, Augmented Coding with Kent Beck

In episode 35 of Generationship, Rachel is joined by Brooke Hopkins to explore what it takes to make voice AI agents reliable, robust, and ready for real-world deployment. Drawing from her experience at Waymo and her current work at Coval, Brooke reveals how testing and evaluation are the key to staying ahead in a fast-moving AI landscape.

Generationship - Ep. #35, Wisdom with Brooke Hopkins of Coval

In episode 13 of Open Source Ready, Thorsten Ball of Sourcegraph joins Brian and John to unpack the real-world engineering decisions behind language choices, like Microsoft using Go for the recent TypeScript compiler rewrite. Explore the importance of continuous learning in tech, the benefits of knowing multiple programming languages, and how AI agents are poised to reshape developer workflows.

Open Source Ready - Ep. #13, Why Microsoft Chose Go: A Deep Dive with Thorsten Ball

In episode 6 of Platform Builders, Christine Spang and Isaac Nassimi chat with Brad Rigby about Canopy’s strategic shift from a niche tax tool to a leading accounting practice management platform. This conversation explores the challenges and triumphs of this major pivot, the nuances of building vertical SaaS, and how Canopy is leveraging AI to streamline workflows and make accounting tech essential.

Platform Builders - Ep. #6, Making Accounting SaaS Sexy Again with Brad Rigby

In episode 81 of o11ycast, Charity Majors and Martin Thwaites dive into a lively discussion with Hazel Weakly and Matt Klein on the evolving landscape of observability. The guests explore the concept of observability versioning, the challenges of cost and ROI, and the future of observability tools, including the potential convergence with AI and business intelligence.

o11ycast - Ep. #81, Observability 3.0-vNext-final-DRAFT with Hazel Weakly and Matt Klein

In episode 36 of Generationship, Rachel Chalmers speaks with Christine Spang about the past, present, and future of enterprise software, with a particular focus on AI. Spang shares her experiences building Nylas and discusses the practical applications of AI in business, as well as the ethical considerations surrounding its use. Lastly, they explore the social and cultural impact of AI, pondering its effects on human connection and the perception of reality.

Generationship - Ep. #36, Solarpunk with Christine Spang

In episode 14 of Open Source Ready, special guests Mike McQuaid and John Britton join Brian and John to share the story of Workbrew. They unpack their journey in the developer tools space, the evolution of Homebrew, the inspiration behind Workbrew, and their perspectives on the future of developer environments.

Open Source Ready - Ep. #14, The Workbrew Story with Mike McQuaid and John Britton

In episode 82 of o11ycast, Ken and Jess chat with Morgante Pell, the visionary behind Grit, an AI-powered agent designed to automate developer toil and technical debt. The discussion covers the evolution of AI in coding, the challenges of building and deploying AI agents, the future of combining code awareness with production awareness, and Grit’s acquisition by Honeycomb.

o11ycast - Ep. #82, Automating Developer Toil with Morgante Pell of Grit

In episode 7 of Platform Builders, Christine Spang and Isaac Nassimi dive deep into the world of CRMs and SaaS strategy with Steve Oriola, CEO of Unbounce. Steve shares his insights on the historical shifts in CRM technology, the critical role of data in modern marketing solutions, and his approach to leading companies through significant transitions and acquisitions. Learn how focused product development and a strong company culture can drive success.

Platform Builders - Ep. #7, SaaS Before It Was Cool with Steve Oriola

In episode 15 of Open Source Ready, Brian and John chat with Adewale "Ace" Abati from Block about Codename Goose, an open-source AI agent, and the underlying Model Context Protocol (MCP). They explore how AI agents are revolutionizing developer workflows, the concept of "vibe coding" for rapid prototyping, and the future of AI in productivity and accessibility.

Open Source Ready - Ep. #15, Codename Goose and the Future of AI Agents with Adewale Abati

In episode 83 of o11ycast, the Honeycomb team chats with Dan Ravenstone, the o11yneer. Dan unpacks the crucial, often underappreciated, role of the observability engineer. He discusses how this position champions the user, bridging the gap between technical performance and real-world customer experience. Learn about the challenges of mobile observability, the importance of clear terminology, and how building alliances across an organization drives successful observability practices.

o11ycast - Ep. #83, Observability Isn't Just SRE on Steroids with Dan Ravenstone

In episode 37 of Generationship, Rachel Chalmers chats with Latrice Barnett and Kanika Chander from The Majority Collective about their mission to empower underrepresented founders. The conversation covers the practical benefits of fractional expertise, the importance of defining clear company strategies, and a thought-provoking exchange on the opportunities and pitfalls of artificial intelligence in shaping the future of entrepreneurship.

Generationship - Ep. #37, Optimism with a Plan with Latrice Barnett and Kanika Chander

In episode 8 of Platform Builders, Christine Spang and Isaac Nassimi are joined by John Melas-Kyriazi, founder and CEO of Standard Metrics. John shares his journey from VC to founder and how he’s rethinking investor–portfolio company collaboration. From spreadsheets to vertical SaaS, and now to AI-powered platforms, John dives deep into building software that’s truly purpose-built for venture capital.

Platform Builders - Ep. #8, The Beauty of Vertical SaaS with John Melas-Kyriazi of Standard Metrics

In episode 16 of Open Source Ready, Brian and John sit down with Mitchell Hashimoto, founder of HashiCorp, to discuss his journey after leaving the company and his latest passion project, the open source terminal emulator Ghostty. Mitchell shares the accidental origins of Ghostty, his pragmatic approach to technology, and his thoughts on the current state of open source business models. Lastly, they explore the complexities of AI development and the trade-offs of foundation governance.

Open Source Ready - Ep. #16, Building Tools That Spark Joy with Mitchell Hashimoto

In episode 38 of Generationship, Rachel Chalmers sits down with Heidi Waterhouse, co-author of "Progressive Delivery." They unpack what Progressive Delivery means as an extension of continuous delivery, focusing on the crucial role of user experience in software development. Discover fresh insights on user autonomy, the pitfalls of uninvited AI, and how to bring empathy back into the software lifecycle.

Generationship - Ep. #38, Wayfinder with Heidi Waterhouse

In episode 47 of The Kubelist Podcast, Marc and Benjie sit down with Grant Miller, Founder and CEO of Replicated. This talk chronicles the triumphs and tribulations of Replicated and the many entrepreneurial lessons learned along the way. Grant and Marc also unveil SecureBuild, a new offering for open source projects. Lastly they share their firsthand experiences using AI-assisted coding tools and how they’re revolutionizing productivity.

The Kubelist Podcast - Ep. #47, SecureBuild with Grant Miller of Replicated

In episode 9 of Platform Builders, Christine and Isaac sit down with Manny Medina, founder and CEO of Paid, to unpack the tectonic shift happening in software. From the rise of AI agents that autonomously perform tasks, to the death of seat-based pricing, and why ARR and SaaS metrics just don’t make sense anymore—Manny makes a compelling case that we’re entering a new era. If you're building, investing in, or working with AI-native companies, this is essential listening.

Platform Builders - Ep. #9, Manny Medina Explains: What the F Is an AI Agent?

In episode 17 of Open Source Ready, Brian and John speak with Docker founder Solomon Hykes about his latest project, Dagger, and its mission to fix the pain points of modern CI/CD. Solomon explains why DevOps is due for a systems-level rethink and how AI agents are changing the way software gets built and shipped.

Open Source Ready - Ep. #17, AI Native Software Factories with Solomon Hykes

In episode 39 of Generationship, Rachel speaks with Simon Willison, founder of Datasette and co-creator of Django. Simon discusses the surprising resurgence of blogging, his coining of the term “prompt injection,” the power of learning in public, and how he uses GitHub issues as an external brain to manage hundreds of projects. This quick-witted and humorous conversation offers a pragmatic look at leveraging today's tools for maximum productivity and impact.

Generationship - Ep. #39, Simon Willison: I Coined Prompt Injection

In episode 84 of o11ycast, Ken Rimple and Martin Thwaites welcome Maddy Montaquila, lead PM for .NET Aspire at Microsoft. This episode dives into the "magic" of Aspire, exploring how it streamlines the developer experience from frictionless app startup to telemetry-rich development. Discover how Aspire makes telemetry a first-class citizen, simplifying debugging and enhancing observability for modern applications.

o11ycast - Ep. #84, Maddy Montaquila on .NET Aspire

In episode 18 of Open Source Ready, Brian Douglas and John McBride are joined by Christopher Burns to unpack the complexities of consent management and cookie banners. Discover how Christopher’s open source project, c15t, aims to simplify privacy compliance for developers, bridging the gap between legal requirements and practical implementation. This episode offers a fresh perspective on why consent is not just a legal burden, but a critical component of modern web development.

Open Source Ready - Ep. #18, Consent Management with Christopher Burns

In episode 10 of Platform Builders, Christine Spang and Isaac Nassimi chat with Seth Besmertnik about Conductor's journey through the WeWork acquisition and its incredible comeback from near-disaster, offering a powerful lesson in resilience and leadership. The conversation then pivots to the future, exploring how AI is about to turn the web upside down. Seth provides a clear framework for how brands must adapt their content and SEO strategies to survive and thrive in this new AI-driven world.

Platform Builders - Ep. #10, Building Leverage, Not Features with Seth Besmertnik

In episode 40 of Generationship, Salma Mayorquin of Remyx AI unpacks the shift from traditional MLOps to ExperimentOps—a framework for scaling insight in modern AI development. With stories from Netflix, Yelp, and Stripe, she explains how teams are bringing foundation models into production and what it takes to keep up. If you're grappling with LLMs, MLOps, or decision paralysis in GenAI, this one’s for you.

Generationship - Ep. #40, ExperimentOps with Salma Mayorquin of Remyx AI

Welcome to Demuxed, a new podcast for and by engineers working with video. Demuxed is hosted by Matt McClure, Co-founder of Mux, Steve Heffernan, Co-founder of Mux, and Phil Cluff, Director of Media Technologies at Brightcove.

In this first episode, Matt, Steve, and Phil are joined by Reinhard Grandl, Solutions Architect at Bitmovin. The group has a great discussion about NAB 2016, 360 video on the web, and what’s next in online video delivery formats.

Producer: Ted Carstensen
Editor: Lucas Oswald

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Demuxed - Ep. #1, Introducing Demuxed

Heavybit is the leading early-stage investor in enterprise infrastructure. Since 2013, we've helped launch and scale visionary technical startups—from DevSecOps and feature flagging to AI code generation and beyond. We go hands-on from day 0, backing founders as they turn code into companies and build the future of software from the bottom up to the top down.

Heavybit

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