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.

Polly Allen is a former Principal PM at Amazon Alexa, where she led the launch of the first generative AI answers on Alexa in 2020. With over two decades of experience across software engineering, machine learning, and product leadership, Polly knows exactly how to turn cutting-edge AI into real-world products that ship—and scale.

But she’s not just a corporate success story. Polly is also the founder of AI Career Boost, a multi–six-figure AI training company helping professionals leap into AI leadership without needing a PhD or a dev team. Her students have launched AI side hustles, landed dream jobs, and even raised funding—thanks to her unique ability to break down complex AI concepts into clear, strategic action.

Polly built her own profitable AI business from scratch—and now she teaches others how to do the same. Whether you’re dreaming of startup freedom or a fundable idea, she’s your shortcut to skipping the fluff and finding what works.

I’m Joel. I’m a CEO, startup advisor, podcast host and I host events for founders.

Vygo

Vygo believes every human deserves a world-class education and that social experience is at the core of impactful learning. The Vygo platform gives every learner a social education community.

Startup Advising

I work with early-stage founders to clean up their ops, sharpen their story, and build companies they actually want to run.

Startup Social House

Real startup people. Monthly events. Free drinks.

No panels, no pitching - just music, free drinks and name tags.

DO AS I SAY

An advice show about the real problems in startups. Each week I bring on best-selling authors, unicorn founders, and investors to workshop the real and vulnerable challenges we face in the startup world.

Pitch Please Game

A card game built for founders who like to laugh. Hustle your way to the top in this cutthroat pitching showdown.