AI After Hours

Hosted by Polly Allen & Yuying Chen-Wynn

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Latest episode

Jan 2026

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EN-US

About the show

Join Polly Allen (AI Career Boost, ex-Alexa AI Principal PM) and Yuying Chen-Wynn (Wittingly Ventures, formerly CPO and Barnes and Noble Education and Head of AI at Peak 6) as they serve up their no-BS takes on the month’s juiciest AI headlines. From wild research reactions to workplace adoption struggles, we call out what’s real, what’s hype, and what’s just plain ridiculous in AI. Irreverent. Insightful. Slightly buzzed. It’s AI After Hours.

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22 recent

January 28, 2026Episode 2247 min

How an AI Side Hustle Reached Revenue in 60 Days (Without Overbuilding)

Most people think winning with AI means building better tech. In reality, it means building less — and validating faster. In this episode, we break down a real case study of an AI side hustle that reached revenue in under 60 days by staying laser-focused on one question: Would someone pay for this today? We cover: How early charging validated real demand Why obsessing over conversion beats adding features The role AI search now plays in discovery How non-technical founders can move fast with modern AI tools The mindset shift that turns ideas into revenue This conversation is for builders, solopreneurs, and operators who want proof before polish — and results before complexity. Irreverent. Insightful. Slightly buzzed. It’s AI After Hours. LINKS: Polly Allen LinkedIn: ⁠ https://www.linkedin.com/in/pollymallen/ Blog: https://aicareerboost.com/interested AI Career Boost: ⁠https://www.aicareerboost.com/⁠ Yuying Chen-Wynn LinkedIn: ⁠ https://www.linkedin.com/in/yuyingchenwynn/ Blog: https://yuying.substack.com/ Wittingly Ventures: https://wittinglyventures.com/

December 31, 2025Episode 2133 min

The Fastest Way to Win With AI: Solve Real Problems People Will Pay For

There’s a lot of noise around AI right now. People love to talk about bubbles, hype cycles, and overnight success. But when you look at what’s actually happening on the ground, a very different story emerges. In this episode, we break down real AI product success stories from solopreneurs and founders who shipped fast, validated real demand, and focused relentlessly on conversion—not perfection. From a solo founder who built a mobile app using ChatGPT and Cursor and hit 20,000 downloads in a single week, to a broader discussion on why the so-called “AI bubble popping” is actually a healthy filter for the ecosystem, this conversation is about what actually works. This isn’t about chasing trends or quick cash grabs. It’s about having strong instincts for real problems, moving fast, and letting the market validate your ideas. Irreverent. Insightful. Slightly buzzed. It’s AI After Hours. LINKS Polly Allen LinkedIn: https://www.linkedin.com/in/pollymallen/ Blog: https://aicareerboost.com/interested AI Career Boost: ⁠https://www.aicareerboost.com/⁠ Yuying Chen-Wynn LinkedIn: https://www.linkedin.com/in/yuyingchenwynn/ Blog: https://yuying.substack.com/ Wittingly Ventures: https://wittinglyventures.com/

December 10, 2025Episode 2035 min

How I Built an AI Product Without Coding (And Got Paying Customers Fast)

Want to build an AI product but don’t know where to start? In this video, we break down the exact process we used to validate, design, and sell an AI product before writing a single line of code. You’ll see how we used “vibe coding” to build a simple AI prototype, test it with a real small business owner, and turn that prototype into a paid engagement. Whether you’re a non-technical founder, an entrepreneur exploring AI, or someone looking for an AI-powered side hustle, this step-by-step breakdown will show you how to turn an idea into revenue—fast. In this video, you’ll learn: How to validate an AI idea using real conversations How to “sell before building.” What vibe coding is and why it works How to build an AI prototype without coding How the prototype turned into a paying customer Why small businesses are an ideal early market for AI tools

October 2, 2025Episode 1937 min

AI Secrets You Never Knew!

Another month, another round of AI headlines! This time, we're diving into the latest from OpenAI and Sam Altman, plus the biggest tech news stories influencing artificial intelligence. We'll also explore the tech trends that are driving the development of large language models. Stay informed with all the AI news! Join Polly Allen (AI Career Boost, former Alexa AI Principal PM at Amazon) and Yuying Chen-Wynn (Wittingly Ventures, former CPO at Barnes and Noble Education and Head of AI at Peak 6) as they serve up their no-BS takes on the month’s juiciest AI headlines. From wild research reactions to workplace adoption struggles, we call out what’s real, what’s hype, and what’s just plain ridiculous in AI. Irreverent. Insightful. Slightly buzzed. It’s AI After Hours. LINKS Polly Allen LinkedIn: https://www.linkedin.com/in/pollymallen/ Blog: https://aicareerboost.com/interested AI Career Boost: ⁠https://www.aicareerboost.com/⁠ Yuying Chen-Wynn LinkedIn: https://www.linkedin.com/in/yuyingchenwynn/ Blog: https://yuying.substack.com/ Wittingly Ventures: https://wittinglyventures.com/

August 4, 202539 min

AI After Hour Summer Edition: Anthropic’s Legal Win, Apple’s Reasoning Drama, and HR’s AI Crisis

AI After Hours – Summer Edition: Copyright showdowns, reasoning meltdowns, and HR mayhem! Anthropic scores a legal win that could reshape LLM training. Apple releases a reasoning paper that stirs up more drama than insight. And HR? They're drowning in AI-generated résumés while legally barred from using AI themselves. Oh, and did we mention robots folding laundry offline ? Join Polly Allen (AI Career Boost) and Yuying Chen-Wynn (Wily Ventures) as they serve up their no-BS takes on the month’s juiciest AI headlines. From wild research reactions to workplace adoption struggles, we call out what’s real, what’s hype, and what’s just plain ridiculous in AI. Irreverent. Insightful. Slightly buzzed. It’s AI After Hours.

June 16, 202549 min

17: May 2025

A quick glimpse into what happened in the world of AI in May 2025! THE SHOW AI After Hours with Polly Allen and Yuying Chen-Wynn is an irreverent attempt to 'edutain' about the latest AI headlines & tools! THE LINKS Recommendations For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested Polly Allen LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠ Yuying Chen-Wynn LinkedIn: ⁠https://www.linkedin.com/in/yuyingchenwynn/⁠ Blog: https://yuying.substack.com/

May 5, 202546 min

16: April 2025

A quick glimpse into what happened in the world of AI in April 2025! THE SHOW AI After Hours with Polly Allen and Yuying Chen-Wynn is an irreverent attempt to 'edutain' about the latest AI headlines & tools! THE LINKS Recommendations For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested Polly Allen LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠ Yuying Chen-Wynn LinkedIn: ⁠https://www.linkedin.com/in/yuyingchenwynn/⁠ Blog: https://yuying.substack.com/

April 7, 202548 min

15: March 2025

A quick glimpse into what happened in the world of AI in March 2025! THE SHOW AI After Hours with Polly Allen and Yuying Chen-Wynn is an irreverent attempt to 'edutain' about the latest AI headlines & tools! THE LINKS Recommendations For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested Polly Allen LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠ Yuying Chen-Wynn LinkedIn: ⁠https://www.linkedin.com/in/yuyingchenwynn/⁠ Blog: https://yuying.substack.com/

March 2, 202537 min

14: February 2025

A quick glimpse into what happened in the world of AI in February 2025! THE SHOW AI After Hours with Polly Allen and Yuying Chen-Wynn is an irreverent attempt to 'edutain' about the latest AI headlines & tools! THE LINKS Recommendations For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested Polly Allen LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠ Yuying Chen-Wynn LinkedIn: ⁠https://www.linkedin.com/in/yuyingchenwynn/⁠ Blog: https://yuying.substack.com/

January 26, 202547 min

13: January 2025

A quick glimpse into what happened in the world of AI in January 2025! THE SHOW AI After Hours with Polly Allen and Yuying Chen-Wynn is an irreverent attempt to 'edutain' about the latest AI headlines & tools! THE LINKS Recommendations For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested Polly Allen LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠ Yuying Chen-Wynn LinkedIn: ⁠https://www.linkedin.com/in/yuyingchenwynn/⁠ Blog: https://yuying.substack.com/