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.

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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

In episode 11 of Platform Builders, Christine Spang and Isaac Nassimi chat with Greg Galant. Greg recounts his early entrance into podcasting, social media, and eventually PR tech. He shares war stories from the early 2000s, including launching a podcast before “podcasting” was popular, creating the viral Shorty Awards, and bootstrapping Muck Rack into a multi-million dollar SaaS company. The conversation offers a unique lens on innovation, timing, media evolution, and how AI is reshaping earned media.

Platform Builders - Ep. #11, How LLMs Are Changing PR Forever with Greg Galant

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.

New tracks tagged #Heavybit