BILLIONS · 2026-05-28 · 57 min
On this episode of BILLIONS, I’m sitting down with Sandy Diao, an elite growth operator who has been remarkably right about major market trends long before the rest of the ecosystem. Sandy helped scale products to 200 million users by leading early growth efforts as employee number 30 at Pinterest. She then joined Descript as their first ghost hire, architecting an automated affiliate model that drove 25% of all new users completely self-service. Her thesis is a warning to every modern SaaS operator: the siloed channel specialist is obsolete. In a world flooded by AI-generated content, traditional acquisition paths are collapsing. The future belongs to full-stack, unified operators who realize that trust is the only channel that compounds. In this masterclass, we break down: The Pinterest Support Trench: How responding to raw customer tickets unlocked the insights to rewrite onboarding and drive massive user activation. Data-Inspired vs. Data-Driven: Why chasing exact precision can paralyze early growth, and why directional insights are the secret to building high-velocity engines.
The man who built a bank for people banks don't want - Jason Wilk [Dave]81 / 100
Why focus on only ONE product built a $1B super-brand (on just $6,000) - Pete Maldonado [Chomps]
Why the world’s biggest tech companies may never IPO again - Peter Singlehurst [Baillie Gifford]
Why high valuations are secretly killing tech unicorns - Martino Cadoni [Deepl]
How a $75 sneaker bot became a $300M/Month financial engine - Steven Schwartz [Whop]