Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Apple, Amazon, Buddybuild, Microsoft)

Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft. — In today’s episode, we discuss: Lessons on culture and product from Amazon, Apple, and Microsoft Building and scaling DevTools Finding product market fit and monetizing it Why AI is complicating product market fit How Dennis prioritizes mental health as a founder The common mistake people make when hiring — Referenced: Apple’s acquisition of Buddybuild: https://www.cnbc.com/2018/01/02/apple-agrees-to-buy-buddybuild.html AWS: https://aws.amazon.com Bitbucket: https://bitbucket.org Confluence: https://www.atlassian.com/software/confluence GitHub: https://github.com GitLab: https://gitlab.com Looker: https://looker.com Microsoft Azure: https://azure.microsoft.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Stripe: https://stripe.com Twilio: https://twilio.com Unblocked: https://getunblocked.com/ — Where to find Dennis Pilarinos: LinkedIn: https://www.linkedin.com/in/dennispi Twitter/X: https://twitter.com/dennispilarinos — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:18) Why building for developers is different (07:28) Buddybuild’s origin story (10:40) Early signs of product market fit (12:22) Managing mental health as a second-time founder (21:09) Building and scaling Unblocked (29:52) Dennis’ cautious take on AI (34:20) Being customer-obsessed (35:25) Unblocked’s decision-making process (38:31) Don’t over-index on competency when hiring (43:36) Why great product is everything (45:41) Monetizing product market fit (48:21) The power of positioning (51:48) Why Dennis doesn’t do demos (54:45) How to deal with customer feedback (57:29) Stewart Butterfield’s impact on Dennis