Yuying Chen-Wynn is the former Head of AI at PEAK6, a private equity powerhouse where she led GenAI strategy across the board: buy, build, invest, and risk-manage. From evaluating AI startups for acquisition to scaling AI capabilities across a multi-billion-dollar portfolio, she knows what makes an AI idea fundable—and what gets it shut down in the first five minutes.

Before that, she was Chief Product Officer at Barnes & Noble Education and has spent over 20 years building products—13 of them deep in AI across Big Tech, FinTech, and EdTech. She’s built AI that sells, AI that saves money, and AI that passed more executive reviews than she’d care to count.

Yuying got her start in computer vision back when AI was barely pronounceable—and yes, she really did end up at MIT by accident, thinking she was just applying to schools in Boston.

Today, she co-hosts the no-BS podcast “AI After Hours” with Polly Allen, where they call out hype, hallucinations, and high-risk optimism. Her popular Substack cuts through the noise for product leaders who don’t have time to chase shiny objects.

With Yuying in this sprint, you’re getting investor-grade filters, real product roadmaps, and the blunt honesty you need to figure out: is this thing worth building—or funding?

More at: Wittingly Ventures — Commit acts of AI, wittingly.

Inquire about team purchases