Pioneers of AI

When host Rana el Kaliouby started online dating, she designed algorithms to weigh multiple factors, and evaluated each date in a spreadsheet. Now, she’s rethinking all that. In a very personal LinkedIn post, Rana has wondered if a less engineered, more spontaneous approach can better lead to love – and whether AI can or should play a role.

This inspired the Masters of Scale Summit round table “Love, unoptimized,” where Rana, Masters of Scale co-host Jeff Berman, and Francesca Hogi, founder of the True Love Society, took the stage in San Francisco. They ponder how to balance engineering with serendipity to feel more agency in all our human relationships, and introduce us to the “Meet-Cute Mindset.”

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The world of brain-computer interfaces, or BCIs, is here. Implanted into the brain, BCIs can pick up neural signals for all kinds of use cases – turning thoughts into words without speaking or typing, or even sharing thoughts with third parties before they’re spoken. AI makes this tech much more powerful, processing and interpreting brain data at unprecedented speeds.

Live from Masters of Scale Summit in San Francisco, host Rana el Kaliouby explores the extreme promise and privacy concerns of BCIs with two leading experts: Matt Angle, CEO of the BCI developer Paradromics, and Nita Farahany, professor of law and philosophy at Duke and author of The Battle for Your Brain: Defending the Right to Think Freely in the Age of Neurotechnology.

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Few companies have as much influence over AI’s trajectory as OpenAI. Reid Hoffman sits down with CFO Sarah Friar to understand the precipice of the moment we are in and the decisions that could shape what comes next for each of us.

This conversation was recorded live as part of Masters of Scale Summit on October 21, 2026, at the Presidio Theatre in San Francisco.

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It often feels like the world is divided when it comes to AI — do you lean in, or opt out?

But what if that tension exists within your own household? This week, we're reprising a candid conversation between host Rana el Kaliouby and her two kids. Her son Adam is an AI enthusiast and her daughter Jana is an AI skeptic, a dynamic she wrote about in a recent essay, "I'm an AI Scientist, My Daughter Refuses to Use AI, and I'm Okay with It." She asks them both to explain their different perspectives on AI, how they've embraced it and how they haven't — prompting Rana to reflect on her role as a mother and an AI leader raising both of them. 

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Journalist Kevin Roose has closely watched and written about the AI race for about a decade, and his new book “The AGI Chronicles” documents the handful of driven people at the center of OpenAI, Google Deepmind, and Anthropic – along with their messy relationships, rivalries, decisions, and breakthroughs on the quest to create artificial superintelligence. Kevin recently left his role as a New York Times tech columnist and co-host of the podcast Hard Fork to start a new show, Machine Gods. 

Host Rana el Kaliouby sits down with Kevin to explore what his books reveals about the AI headlines we’re all obsessing over, his concerns around AI safety, and whether AGI is already here. 

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Thibault “Tibo” Sottiaux is OpenAI’s head of Product & Platform, making him responsible for the AI tools used by more than a billion users worldwide. Host Rana el Kaliouby spoke with Tibo about why he’s “proud” OpenAI delayed its latest Astra model over safety concerns, the new suite of agentic products released at DevDay, and what it’s like to lead inside a frontier AI company in this extraordinary moment in history. 

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On this week’s episode we’re excited to share an episode from our sister podcast Possible, a podcast that sketches out the brightest vision of the future.

Useful robots won’t be programmed one task at a time; they’ll need to adapt to unfamiliar objects, environments, and robot bodies. Physical Intelligence cofounder Chelsea Finn (named last month to the TIME100 AI list for 2026) joins Reid Hoffman and Aria Finger to explain how general-purpose robot models learn to act in the messy physical world. She explores why lower-quality training data can strengthen a model, what months of failed laundry-folding attempts revealed, and how the same system can work across different robot platforms. A robot mistaking an oven for a drawer becomes a lesson in the strange line between useful generalization and obvious error. They also examine why robot demos can mislead, how hardware reliability can stall progress, and what it will take to move AI off the screen and into the world.

Congratulations to Chelsea, recently named one of TIME’s 100 most influential people in AI:

https://time.com/collection/time100-ai/2026/chelsea-finn/

For more info on the podcast and transcripts of all the episodes, visit https://www.possible.fm/podcast/

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For the past four decades Sherry Turkle has studied the social and psychological implications of AI. She’s the Abby Rockefeller Mauzé Professor of the Social Studies of Science and Technology at MIT, founding director of the MIT Initiative on Technology and Self, and author of the upcoming book Artificial Intimacy: Who Do We Become When We Talk to Machines? Sherry sits down with Rana to deliver a warning about the slippery slope we’re all stepping on to with our use of AI.  

Sherry is direct and unfiltered in explaining why artificial intimacy is an oxymoron, what happens when humans become emotionally attached to AI, and why replacing human relationships with AI means we’ve basically given up on each other. But don't you worry, she leaves us with a strong message of agency and hope.

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Rudina Seseri is the Founder and Managing Partner of Glasswing Ventures, recently named one of America’s Top Venture Capital Firms of 2026 by TIME and Statista. With a focus on early-stage AI-powered companies, Rudina has been investing in AI since 2016 and has always been ahead of the curve. Host Rana el Kaliouby talks to Rudina about the shifting AI investing landscape, where she sees the real value in AI, and what she looks for in a founder before she writes her first check. 

Learn more about Pioneers of AI: http://pioneersof.ai/

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For decades, e-commerce rewarded the biggest brands that could buy their way to the top of search results. AI is changing that. Shopify COO Jess Hertz joins Rapid Response to share what Shopify's data reveals about the agentic shopping revolution in real time, and how the company is building the infrastructure layer that makes products discoverable and purchasable by AI. Plus, why Shopify's engineers can spend freely on AI tokens while the rest of the business world agonizes over ROI, and what it looks like when a company powering over 14% of online shopping decides to win the future or die trying.

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