SHIFT

The spray-and-pray approach to AI investing is dead. Join us as we discuss what it takes to stand out in a saturated market as we move beyond the hype to identify real moats and what’s next for investors in this space. 

This episode was taped before a live audience at Web Summit Vancouver. 

We meet: 

Andy McLoughlin is a seed-stage investor at Uncork Capital focused on B2B software, developer tools, and applied AI — and before VC, he co-founded Huddle, an enterprise collaboration platform that was acquired in 2016. 

George Mathew is a self-described "deep operator turned venture capitalist" at Insight Partners, with 20+ years building companies including as CEO of Kespry and President & COO of Alteryx, which he scaled through its IPO. 

Emily Fontaine leads IBM's $500 million Enterprise AI fund and quantum investing strategy — she's spent 15 years at IBM, previously serving as Executive Advocate to IBM's Chairman and CEO, and as AI Federal Leader for IBM Consulting. 

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

What if we've all become so focused on what technology is capable of that we've lost track of what children are capable of?  

We Meet: 

Andrew Sliwinski is the VP and Head of Product Experience for Lego Education. 

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

What if the standard approach to responsible AI, built around aspirational values like fairness and transparency, is fundamentally broken in the age of AI agents? 

We Meet: 

Reid Blackman is the author of the new book The Ethical Nightmare Challenge and the founder of AI ethics consultancy Virtue.

Episode Links:

Reid and Jennifer are speaking at the Drawing Room Salon on May 20:

https://thedrawingroom.ai/

Reid's new book:

https://www.amazon.com/Ethical-Nightmare-Challenge-Avoid-Worst-ebook/dp/B0GRC1ZPYX

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

How do you build intelligent systems that people trust? Then, how do you keep that trust when things go wrong? Because when things do, it’s not the tech that loses face but the brand people relied on. 

This episode was taped before a live audience on stage at the HumanX Conference in San Francisco.

We Meet: 

Radha Basu, Founder & CEO of iMerit

Shuman Ghosemajumder, Co-founder & CEO of Reken

Andrea Thomaz, Co-founder & CEO of Diligent Robotics

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

Capital One is the largest issuer of credit cards in the U.S. It’s also one of the largest banks, and car finance companies, in the country.  We learn from its experience building proprietary AI across fraud prevention, agentic workflows, customer experience, and risk and compliance in the latest installment of our oral history project.

We Meet: 

Capital One’s Head of AI Foundations Milind Naphade 

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

Engineers charged with maintaining secure and reliable sites and services need to be able to observe what’s going on inside their systems. That observability data helps them spot issues sooner,  fix problems faster, and learn from the whole experience.

A live conversation from the stage at the HumanX Conference in San Francisco.

We Meet: 

Christine Yen is the Co-founder and CEO of Honeycomb,

Jennifer Tejada is the CEO and chairperson of PagerDuty

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

Best-known as the creator of ImageNet, we meet the Godmother of AI, Dr. Fei-Fei Li In the latest installment of our oral history project. She's a Chinese-American computer scientist and the creator of ImageNet - the dataset that made rapid advances possible in this field of AI that helps computers take meaningful information from things like photos and videos.

We Meet: 

Stanford University's Fei-Fei Li, author of "The Worlds I See: Curiosity, Exploration, and Discovery at the Dawn of AI" and the founder of World Labs

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

Each day more than 11,000 people in the US turn 65 years old. It adds up to more than 4,000,000 people a year, and the labor force that serves them is struggling to keep up with that demand - a problem that’s unlikely to go away anytime soon. 

We explore this shift and how might technology be used to help people age in place in the latest installment of our oral history project.

We Meet: 

Chia-Lin Simmons is the CEO of Logic Mark

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

 Lately, it feels like you can’t go more than a few minutes without hearing someone talk about AI agents, and there’s a very good reason for that. Agents are doing more work, more quickly and in more places, and we’ve developed ways to help them retain knowledge from things they’ve done, and then build upon those experiences.

But what if the experience agents gain on a job changes the work product in ways we didn’t predict? How do you make sure that agent does what you want it to do? This episode, we explore the alignment problem in the age of AI agents.

We Meet: 

Andy Hall is a professor in the Political Economy Group at Stanford, and a senior fellow at the Hoover Institution.

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

Astro Teller, Alphabet’s Captain of Moonshots, joins us for a conversation about the importance of failure, workplace culture in a moonshot factory, and not throwing away your shot.

We Meet: 

Astro Teller is the Captain of Moonshots at X, Alphabet's Moonshot Factory

Credits:

This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

This episode originally ran in April 2025.