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Jack Newton & Dennis Pilarinos on $500M ARR, Apple Exits and AI
Guests
Jack Newton
Built the company from a bootstrapped lifestyle business in Edmonton to the operating system for the legal industry — $500M+ ARR, $5B valuation, and 18 years in. Studied computer science at the University of Alberta, caught the startup bug at a life sciences spinoff, and founded Clio in 2008 with his childhood best friend. Has run every single day for 27 years without missing one.
Dennis Pilarinos
Spent nine years at Microsoft helping build Azure from a direct ethernet cable in his office, then became Amazon's first employee in Vancouver. Built BuddyBuild on the side, took it from zero to Apple acquisition in three years, and got the band back together to start Unblocked, a tool that gives developers and their AI agents instant institutional knowledge. SFU computer science. Dad of a seven-month-old.
Description
In this episode, Willson sits down with Jack Newton (CEO, Clio) and Dennis Pilarinos (CEO, Unblocked) to talk about the sliding door moments that define companies, why AI is transforming legal and developer tooling faster than almost any other industry, and what it really takes to build for the long haul.They get into managing a cap table across decades, building context engines that actually win markets, and why the founder brain never fully shuts off — even when you’re kayaking with your kids.
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