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AI After Hours

Polly Allen & Yuying Chen-Wynn

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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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Can we learn to make smarter choices? Listen in as host Katy Milkman--behavioral scientist, Wharton professor, and author of How to Change--shares stories of high-stakes decisions and what research reveals they can teach us. Choiceology, an original podcast from Charles Schwab, explores the lessons of behavioral economics to help you improve your judgment and change for good. Season 1 of Choiceology was hosted by Dan Heath, bestselling author of Made to Stick and Switch. Podcasts are for inf ...
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If you've ever gotten well into a project—maybe a DIY renovation—and then realized that you've taken the wrong approach, you probably know that it's very tempting to just stay the course. Starting all over again would be so painful, even if starting over is clearly the best option. Or maybe you've taken a wrong turn on a hike and only noticed it a …
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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 THE GUEST Don Stoddard is a powerhouse product leader with over two decades of experience driving SaaS innovation across B2B and B2C markets. From scaling globa…
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What makes an effective team? Talent? Skill? Discipline? In this episode of Choiceology with Katy Milkman, we're looking at some of the more surprising ingredients of successful teams, according to science. Teams where the whole is greater than the sum of its parts. You'll hear the story of the Kon-Tiki expedition—a harrowing journey across the Pac…
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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 THE GUEST Kelly-Ann Bakhos is a dynamic product leader with a diverse career spanning healthcare, retail, gaming, data analytics, and election systems. She has …
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We've all been there. Maybe you fumbled a line in a presentation. Or tripped on a shoelace. Or suffered a bad hair day. It can feel like the whole world is watching you—and judging you—in those embarrassing moments. But are people paying as much attention to you as you think? In this episode of Choiceology with Katy Milkman, we explore why we tend …
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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 THE GUEST Dave Stys is a product leader with one of the most fascinating paths into tech—starting his career calibrating instruments on the Hubble Space Telesco…
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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 …
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You've probably been in situations where multiple friends recommend the same product. It must be great, if everyone is talking about it, right? But then you find out that those friends had all just seen the same product on a popular TV show. What seemed like independent recommendations really came from a single source. In this episode of Choiceolog…
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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 THE GUEST Rebeca Assunção is a senior product leader driving innovation at the intersection of AI, mobility, and no-code tools. With over a decade of experience…
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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 …
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It's a new season of Choiceology, an original podcast from Charles Schwab. New episodes arrive every two weeks, so please follow us in your favorite podcasting app. Important Disclosures The comments, views, and opinions expressed in the podcast are those of the speakers and do not necessarily represent the views of Charles Schwab. Data contained h…
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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 THE GUEST Denise Hadzidakis is a transformational technology leader with a proven track record of building and scaling high-impact IT organizations across healt…
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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 THE GUEST David Murray is an accomplished product and operations leader with a passion for shaping the future of technology through innovation and impact. With …
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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 THE GUEST Ramkumar Nimmakayala is a strategic AI and product data leader, dedicated to advancing ethical, human-centered innovation at scale. With nearly two de…
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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 t…
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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 t…
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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 THE GUEST Bruce Randall is a seasoned sales leader and AI strategist with a passion for bridging the gap between cutting-edge technology and real-world business…
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Were you the kind of kid who devoured all your Halloween candy in one sitting—or savored it daily until, somehow, it was Easter? And when it comes to bad news, do you prefer it all at once or with some time in between? Turns out, the way we bundle or separate life's highs and lows can influence our happiness. In this episode of Choiceology with Kat…
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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 THE GUEST Camila Buenamar is a senior product leader and the founder of Productesas, a fast-growing community empowering Latinas in tech. With a strong track re…
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Would you pay more for a car with 29,999 miles than one with 30,000? The answer should be no—it's a negligible difference, after all—but research shows that people often do pay more than they should for cars that are just short of certain odometer thresholds. In this episode of Choiceology with Katy Milkman, we look at why a price or an age or a te…
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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 THE GUEST Prasanna Limbu is a dynamic IT leader with a proven track record of driving large-scale digital transformations across industries. With deep expertise…
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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…
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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…
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Streaks have long been logged in the world of sports. And for tracking habits, like daily writing. But now apps encourage us to keep streaks going for just about anything. Messaging friends, learning new languages, meditating, exercising, you name it. In this episode of Choiceology with Katy Milkman, we explore the motivational power of streaks. An…
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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 THE GUEST Dr. Yisha Stiskala-Yu is a clinical psychologist, scientist, and AI product leader transforming the digital health and medtech innovation landscape. W…
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First-born children tend to believe that their parents were harder on them than their siblings are willing to grant. Football fans take disproportionate note of the challenging games on their team's schedules. We're wired to interpret our challenges as bigger than our advantages, even if the reality is more balanced. In this episode of Choiceology …
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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 THE GUEST Kelli "Rua" Klein is a seasoned Product Manager and board member at Firebrand Resiliency Collective, where she leads innovative, AI-powered tools and …
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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…
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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…
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Is it ever possible to see the world objectively, as it is? Turn on the news, open social media, engage with that family member at Thanksgiving, and it appears to some the answer is yes. But what if our biggest blind spot is thinking we don't have a blind spot? In this episode of Choiceology with Katy Milkman, we look at how we can easily be fooled…
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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 THE GUEST Vasuki Chilukuri is a dynamic product leader known for driving impact at scale. At Intel, she pioneered the company’s first 'as-a-Service' model for d…
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Workplaces often rely on numerical ratings for performance reviews. Election debates focus on poll numbers and approval ratings. Your watch counts your steps in a day. Numbers increasingly influence our decisions. In this episode of Choiceology with Katy Milkman, we look at our very human tendency to fixate on digits even when words or graphs repre…
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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 THE GUEST Matt Wei has built a remarkable career in product management and agile transformation, driving impactful innovation at VMware Tanzu Labs. With experie…
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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 THE GUEST Flora Wu is a trailblazing program management leader redefining what’s possible at the intersection of technology and AI. With over a decade of experi…
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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…
  continue reading
 
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…
  continue reading
 
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 THE GUEST Fernando de Buen Lopez is an accomplished innovation and strategy leader with over a decade of experience driving customer-centric design and research…
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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 THE GUEST Suvda Myagmar, PhD, is an accomplished AI product leader with a track record spanning top tech companies like Salesforce, Adobe, and Microsoft, as wel…
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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 THE GUEST Yuying Chen-Wynn is a visionary leader in AI, tech and product strategy, who began her career designing LEGO Mindstorm’s second-generation CPU at MIT.…
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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 …
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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 …
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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 THE GUEST Alex Vega’s career journey is as unique as it is inspiring. Starting as a hairstylist and educator, Alex transitioned into tech through a User Experie…
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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 THE GUEST Adam Schweig’s career has spanned some of the world’s best known brands including NBC, Macy’s, Bareminerals and Estee Lauder. Adam Schweig has over a …
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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 THE GUEST Nico Posner’s whose career has spanned some of the world’s most innovative companies, including LinkedIn, eBay, Clover, and Xero. Nico’s career is a m…
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A quick glimpse into what happened in the world of AI in December 2024! 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…
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A quick glimpse into what happened in the world of AI in December 2024! 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…
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A quick glimpse into what happened in the world of AI in November 2024! 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…
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A quick glimpse into what happened in the world of AI in November 2024! 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…
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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 THE GUEST Annette Holland is a Senior Project Manager and Digital Transformation Leader with a rich background in AI, Agile methodologies, and complex project o…
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