Today's guest is Dennis Pilarinos, who is founder and CEO of Unblocked.
With Dennis, we talked about his journey in tech, from director roles at Microsoft and Amazon, to founding BuddyBuild and later selling it to Apple, to founding Unblocked. We explored the challenges of building Unblocked, and the future of dev tools in the age of AI.
🎙️ Episode
You can watch the full episode on Youtube:
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🥇 Interview Summary
If you are a 🔒 paid subscriber 🔒 you will find my own summary of the interview below.
It’s the 10-minute, handcrafted takeaways of what we talked about, with timestamps to the relevant video moments, for those who don’t have time to sit through the 1-hour chat.
Here is the agenda for today:
🚀 Dennis's Journey Through Tech Giants (02:31)
🏗️ Lessons from Microsoft, Amazon, and Apple (07:27)
🔍 What Unblocked Solves Beyond Coding (11:23)
🧠 The Context Challenge in AI Development (15:31)
🔮 The Future of Developer Tools and Workflows (28:13)
Let's dive in 👇
1) 🚀 Dennis's Journey Through Tech Giants (02:31)
Dennis Pilarinos has been building developer tools for nearly 20 years, starting at Microsoft where he worked on the .NET Framework. His journey began with an incubation project that literally started as "a single machine plugged into a direct internet connection" in his office.
"We went from this group of radicals cannibalizing on-premise licensing businesses to a few years later, that single machine was now geographically distributed around the world. We were all in on the cloud, and that became the Azure platform."
From Microsoft, Dennis moved to Amazon where he worked on the Silk Web browser, a cloud-accelerated browser project. After leaving Amazon, he encountered the frustrating complexity of iOS development workflows, which led him to co-found BuddyBuild—a CI platform for mobile developers.
BuddyBuild went from conception to Apple acquisition in just three years. Dennis describes his career trajectory as being driven by impatience and mediocrity as a developer, constantly asking "why is it so hard to do this?" These frustration points became the foundation for solving real developer problems.
2) 🏗️ Lessons from Microsoft, Amazon, and Apple (07:27)
Working closely with founder CEOs at these tech giants gave Dennis unique insights into their distinct organizational strengths:
🏢 Microsoft — exceptional at building software at scale with well-understood processes for shipping and maintaining software.
🛒 Amazon — leadership principles aren't just wall decorations but core cultural drivers, especially customer obsession, bias for action, and strong ownership.
📱 Apple — masters of building delightful user experiences with multi-year vision that feels inevitable yet surprising when it all comes together.
