As building gets easier and almost anyone can ship an app in an afternoon, what actually separates a product leader who creates leverage from one who doesn’t?
In this special live episode of Supra Insider, recorded on stage at the Toronto Product Conference, Marc Baselga sits down with Colin Matthews, Head of Education for Lenny’s Newsletter and a former founder, PM, and longtime hobbyist builder. Marc lays out a thesis that the best way to prepare for the AI era is to build a real side project, one with actual users and ideally revenue, and Colin pressure-tests it with the framework he uses himself: start with distribution, then work backward to the customers and problems you can reach.
They explore the blurring lines between product, engineering, and design, why the code review bar stays the same no matter who writes the code, when to ship a PR versus a prototype versus a spec, why Colin uses AI for comprehension rather than raw velocity, and the two distribution paths he has actually seen work for solo builders.
If you’re a PM wondering which skills matter most next, a product leader trying to get your team building, or anyone who keeps starting side projects that never find users, this episode is for you.
Huge thanks to Balaji Gopalan, Andrew Williams, and the team at The Toronto Product Conference for hosting us.
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In this episode, we covered the following topics:
(01:26) Marc kicks off Supra Insider’s first live podcast and sets up the thesis on side projects and the three judgments
(04:45) Colin on years of building side projects, a roughly 10% hit rate, and what actually counts as a real one
(06:27) His first project, a walk-in clinic reservation app, and the distribution lesson that stuck
(08:12) The distribution-first framework: start with the channel, then find the customers and problems
(10:25) How to bring distribution thinking into your day job, and the career risk of validating bets that fail
(14:09) The blurring lines between product, engineering, and design, and PMs shipping to production
(15:43) Why the code review bar stays the same no matter who submits the PR
(17:22) Colin’s fourth judgment: deciding whether to ship a PR, a prototype, or a spec
(18:40) The profile picture and Base64 example of a simple feature hiding real complexity
(20:26) Using AI for comprehension over velocity, and why he avoids Supabase on a learning project
(23:31) A beginner-friendly stack and the primitives to layer on one problem at a time
(24:50) The case for prototyping almost everything before writing a spec
(26:41) Design systems as leverage, through the Figma MCP or the codebase itself
(30:26) Where to start: learning versus business, and choosing your intention first
(34:22) The distribution sprint, the “meaningful rep,” and the two paths that work for solo builders
And more!
Links:
Lenny’s Newsletter
Toronto Product Conference: https://www.tpma.ca/conference/toronto-product-conference
Toronto Product Con Association: https://www.tpma.ca/
https://www.tpma.ca/conference/toronto-product-conference
Colin Matthews: https://www.linkedin.com/in/colinmatthews-pm/
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