Will Ruben spent nearly a decade at Meta building AI-powered products like Instagram Reels and content recommendations. Then he walked away to democratize something only executives get: an assistant.In this episode of Forward to Extraordinary, I sit down with Will to discuss his journey from building products for billions of users at Meta to founding Workmate, an AI executive assistant designed to help busy professionals reclaim their time and sanity.
We dig into what it means to be entrepreneurial within a large organization, why being a builder is the clearest signal you're meant to be a founder, and how the cost of code dropping to zero changes everything about product development—except the hard part: distribution.
Will breaks down the difference between building and selling, why personal brand compounds every future effort, and how agentic collaboration is the next frontier of work. This is a masterclass in transitioning from big tech to startup life without losing your edge.
Topics covered:
- Building AI products at Meta: Instagram Reels, content recommendations, and Moments
- What it means to be entrepreneurial inside a large organization
- The moment Will decided to leave Meta and start Workmate
- Democratizing executive assistants through AI: the Uber analogy
- How Workmate handles scheduling, calendar management, and team coordination
- Why distribution and conversion are harder than building
- The future of agentic collaboration and AI teammates
- Building personal brand as a compounding asset for founders
- Why being a builder is the clearest entrepreneurial signal
If you're building a product, contemplating a startup, or trying to figure out how to scale from first customer to real business, this conversation is for you.The cost of building is dropping. The cost of distributing isn't. Act accordingly.
Website: https://www.workmate.com
LinkedIn: https://www.linkedin.com/company/workmatelabs
Instagram: https://www.instagram.com/getaworkmate
X: https://x.com/workmate
YouTube: https://www.youtube.com/@getaworkmate
TikTok: https://www.tiktok.com/@getaworkmate
X: https://x.com/willruben