The New, New Kingmakers: Agents, Developers, and the Future of Software with Stephen O'Grady
The Enterprise AI Show
October 7, 2026
Brandon interviews Stephen O'Grady, principal analyst and co-founder of RedMonk, about his 2013 book *The New Kingmakers* and his recent follow-up, "Agents: The new, New Kingmakers.
Speakers Brandon, Stephen O'Grady
TopicsTechnologyNewsTech News
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Brandon (1:41)
And we're back. Joining me today is Stephen O'Grady, principal analyst and co-founder of RedMonk. Welcome to the show, Stephen
Stephen O'Grady (1:48)
My pleasure
Brandon (1:50)
Well, listen, I don't think you need a long introduction. I think people already know who you are, and we're gonna talk a little bit about your your great book, The New Kingmakers, and your recent response to your own book, if you want a second. But before, before we jump in, I thought I'd start with something kind of fun.
I… Last I looked I've seen on the social media you're, like, a big fitness walker. You've been, like, walking many miles and, you have a bunch of blog posts about it. So I was gonna say are you still, I know you've got family now, priorities and stuff, everything. Are you still getting your walks in? You still making it around your little area out there up in Maine?
Stephen O'Grady (2:18)
I am. I am still still at it. It's, I got into it a couple years ago when I was like tried to get back into running and just kept like, "Oh, my foot hurts or back," or, everything's tweaked, and it was like, eh, just walk a lot, I am fortunate to be in a profession where I can do a bunch of things. Certainly we'll get into the a bit later, but even taking, listening to calls and all that, I can do while I'm walking around. So it's a good way to combine in many cases getting some work done with getting some exercise
Brandon (2:41)
Yeah, no, I think, I agree. I think it's a great way just to… I always, I tell people don't sit at your desk and watch the keynote. Put it in your phone and then walk around and watch the keynote. You'll stay more involved. I did say, one thing that I thought, did you walk something? In, I remember seeing a picture of it was, like, very cold, or it looked very cold. It was, like, snowing, and you did like a long eight-hour walk or something. Is this, am I remembering this correctly, or?
Stephen O'Grady (3:02)
yeah, I've done walks that are cold. I've done walks that are pretty long. I did 50 miles one time, 60 miles another time.
Brandon (3:07)
Like a serious walker.
This is-- I don't want people to be like,"It's just I'm just out like taking a stroll." Like you're doing the real thing,
Stephen O'Grady (3:13)
No, but honestly, I tell people all the time, man if all you can do is get out and take a stroll, like great, man. Like any, any movement's good. So if you got 20 minutes, half hour, whatever it is, recommend it
Brandon (3:21)
Do what you can do. Hopefully we always get notes that people are running, walking, wa- walking their dogs about the podcast. So hopefully people are out right now. They're listening to us while they're on a, a great new walk. Listen as I mentioned at the top there, so you wrote a book in 2013, The New Kingmakers, which I think was like, I don't know, I think it's like a seminal book for the industry, took a lot of ideas at the time and kinda condensed them into a nice narrative for all of us. And but of course, many things have changed there. So I thought maybe let's just start with for those that haven't read the book, maybe why don't you set it up? What was-- Take us back to 2013 What were you thinking about? What prompted you to write the book, and what, kinda what's the core thesis of it?
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