How to Control AI With Data-First Governance
Embracing Digital Transformation
October 18, 2026
Tim Freestone argues that AI is not leveling the playing field; it is magnifying the gaps organizations already had in data management, cybersecurity control, and operational discipline.
Speakers Dr. Darren Pulsipher, Tim Freestone
TopicsTechnologyBusiness
Dr. Darren Pulsipher (0:00)
Welcome to Embracing Digital Transformation. Before we dive in, I wanted to personally thank you for listening. Many of the ideas we discuss on this show inspired my new book, AI Augmented Teams. If you're looking for practical ways to combine human expertise and AI to achieve better outcomes, I think you'll find it valuable. Learn more at paydar.ai.books. That is paidar.ai.
Now let's get started with the show.
Tim Freestone (0:30)
And trying to keep on top of it, and just a bit of empathy and sympathy for what they're going through, because the stakes are very high, obviously, for this amount of compressed change. When you're dealing with, you know... The sensitivity and the decisions. I think we have a couple of people that run the global economy. So...
You know, it's a balance of anxiety and excitement, if I were to collapse it into one statement.
Dr. Darren Pulsipher (0:59)
Why this matters to you. AI is moving faster than most enterprises can govern it, and that creates a problem executives can no longer ignore. The real risk is not just adoption. It is what happens when AI meets weak data control, vague metrics, and overstretched security teams. If your organization is asking people to use AI without defining outcomes, controls, or ownership, you are creating motion without progress. In this conversation, we dig into the pressure points leaders need to see before the next wave of AI exposure hits.
Welcome to Embracing Digital Transformation. This is Dr. Darren. On this episode, how to control AI with data-first governance, with Tim Freestone, Chief Strategy Officer from Kiteworks.
All right, Tim, welcome to the show.
Tim Freestone (1:57)
Yeah, thanks, Darren. Third time's a charm, right?
Dr. Darren Pulsipher (2:00)
Third time's a charm. Yeah, it was funny because we already had started our little conversation, and then everything went completely. And I told you earlier, first thing I checked, I know you're in San Mateo, first thing I checked was, was there an earthquake in San Mateo?
Because I used to work in the Bay Area, and that was always something that you dealt with, right?
Tim Freestone (2:21)
This, and by the way, this is the answer that every CISO gives the board when something goes wrong. They go, I don't know, we were fine, and then everything went kapplui. That's my first joke of the series.
Dr. Darren Pulsipher (2:33)
That's exactly right.
Tim Freestone (2:34)
Yeah.
Dr. Darren Pulsipher (2:36)
So, apropos for today, because we are going to talk about AI, we're going to talk about AI agents and the danger, and the control, and there's a whole bunch going on around that space. But before we get started with that, everyone that listens to my show knows that I only have superheroes on the show.
Every superhero has a background story and origin story. So Tim, what's your origin story?
Tim Freestone (3:01)
Yeah. Well, thanks for the invitation to give it. I'll make it as short but insightful as possible. So I was originally from Montana. I'm one of the few people that makes it out. It's such a beautiful state. But aside from fly fishing and things like that, which I love, to pursue a career, you have to go somewhere else, changing a little bit now. But back in the year 1998, which was when I graduated college, that was the case. So I had two options. I go to San Francisco or I go to New York City. And I decided to go to New York City. I packed up a backpack. I had $2,000 saved to my name, and I went to New York City without any job. And I stayed in the spare bedroom of a Spanish gypsy in Weehawken, New Jersey, for about three months until I found a gig.
Longer story short, I ended up connecting with a guy who was doing some consulting around tech companies. Because at that time, which was around the year 2000, this is the start of everything we know for tech today.
And we started a company, and it was a marketing services company. We grew it from a Morley. The intern was our first employee. We grew it to having hundreds of customers over about 10 years.
And this is the heyday of tech, right? We saw companies like EMC, NetApp, Cisco, all those companies get bigger and bigger and bigger, and we're able to get kind of a front row seat to, again, like hundreds of companies all the way up the supply chain from channel partners to big manufacturers of just what was going on and the evolution in technology. And towards the end of that, I realized I was getting kind of premature gray hair because it's a lot of work running a services agency. And we decided to, for our own sake, wind it down. I went to one of our customers, I went client side, I worked with NetApp.
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