How AI Solopreneurs Build $100K Products (Live Showcase)

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.

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.

Yuying Chen-Wynn is currently the Head of AI at CohnReznick, a former Head of AI at PEAK6, a private equity powerhouse where she led GenAI strategy across the board: buy, build, invest, and risk-manage.

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.

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