Authors in August: Vasant Dhar & “Thinking With Machines” artwork

Authors in August: Vasant Dhar & “Thinking With Machines”

Rule Breaker Investing

August 12, 2026

Artificial intelligence may feel suddenly everywhere, but AI pioneer Vasant Dhar has had a front-row seat for more than four decades—teaching AI, building companies around it, and bringing machine learning to Wall Street long before ChatGPT entered the conversation.
Speakers: David Gardner, Vasant Dhar

Topics: Investing, Business

**David Gardner** (0:00)
August means Authors on Rule Breaker Investing, and amazingly, this is our ninth year of Authors in August. Last week, philosopher T Nguyen joined us to ask, what happens when the scores around us start shaping what we value? This week, we turn to the technology shaping just about everything else these days, and that's artificial intelligence. My guest Vasant Dhar has been working in AI since long before most of us had heard the term, teaching it, building companies around it, bringing machine learning to Wall Street, and now writing his book Thinking With Machines. What has somebody with a 40-year front row seat learned about where AI came from, where it's going, and most importantly, how we humans should think alongside it without surrendering our own judgment?
Thinking With Machines with Vasant Dhar, only on this week's Rule Breaker Investing.

**SPEAKER_2** (1:01)
It's the Rule Breaker Investing Podcast with Motley Fool co-founder, David Gardner.

**David Gardner** (1:11)
Welcome back to Rule Breaker Investing. I'm excited to be joined by Vasant Dhar in just a minute. Let me mention this is Authors in August, and what are we doing next week? Well, our third and final author for August is author of book I've loved and returned to for years, and that's The Why of Work by Dave and his wife, Wendy Ulrich. We began this month by asking T Nguyen how the scores around us shape what we value, and Vasant Dhar is now going to help us think alongside increasingly intelligent machines. Next week, perhaps the most personal question of all, why do we work? Not just why we need a paycheck, but why some workplaces give us energy, identity, connection, and purpose, while others drain them away. If you lead people, if you work with people, or simply spend a substantial portion of your waking life working, tune in next week for my conversation with Dave Ulrich on The Why of Work.
All right, Vasant Dhar is the Robert A Miller Professor at the Stern School of Business and Professor of Data Science at New York University. Vasant refers to himself as an artificial intelligence researcher and data scientist. But given his long and deep history with AI, I'm going to add my own word here to characterize him, pioneer. Vasant Dhar is an AI pioneer and host of the podcast Brave New World, which explores how AI and other technologies are transforming humanity. I was privileged, I should mention, to appear on Brave New World this summer.
If you'd like to hear what happens when questions get turned on me instead of vice versa, do listen in to my foolish talk with Vasant on Brave New World, wherever you find and listen to podcasts. Our episode came out just a few weeks ago on July 16th. Vasant Dhar, great to be with you again, and welcome to Rule Breaker Investing.

**Vasant Dhar** (3:09)
David, delighted to be on the show. Very much looking forward to our conversation.

**David Gardner** (3:13)
This is going to be a fascinating conversation, and I know that not even knowing where we're going exactly because one of my favorite lines comes from Lord Peter Whimsy, which was Dorothy Sayers' answer to Sherlock Holmes. So a century ago, her hero was Lord Peter Whimsy, her protagonist, and his family crest said, where my Whimsy takes me. Vasant, I think that's very apropos of our conversation this week.

**Vasant Dhar** (3:39)
I like that.

**David Gardner** (3:40)
Thank you. Let me just start by saying, you were there before it was cool.
Vasant, you've taught your first AI course, and I have this right. In 1984, you founded four AI companies, you brought machine learning to Wall Street in the 1990s, and now four decades later, suddenly, everybody else is now using AI as well. Let me start by asking you, Vasant, what does the AI revolution look like to somebody who's actually watched almost the whole thing happen?

**Vasant Dhar** (4:10)
Well, it's almost like I've watched it in slow motion. I don't mean for that to sound like a train wreck, it's actually been quite a ride in slow motion. And I say slow motion because it's been 40 plus years. It's been 47 years since I got into the field in 1979 And little did I realize at the time what I was getting into. And as I sometimes refer to the famous Jerry Garcia line, what a long strange trip it's been.
It really has. But it didn't answer your question specifically, which is that what I've really seen is this progression, what I call these paradigm shifts, where we've gone from the paradigm of specification, which is what we used to do in the late 70s, the 80s, where we specified knowledge by talking to humans, by eliciting what they knew and then encoding it into the computer. It sounds so arcane now, but that was it. And we thought that that would take us to the promised land. Little did we know that those tools really were not sufficient.

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