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Don Gregori

Don Gregori

Chief Operating Officer of First Factory, author of The Emergent Leader, and AI Journal contributor

Oct 12, 2026

8:01
Yeah.
8:01
Don, how are you guys using Gen Zs in your, your operation? Yeah.
8:06
I mean, we're as primarily a software development company, so I mean, it's very, you know, heavily skewed toward, you know, younger people, especially in Costa Rica.
8:13
Mm-hmm.
8:13
Um, but- Yeah ... you know, I think there's a few things.
8:15
I mean, it's core to our business.
8:16
Um, and, you know, also when you build teams, you know, from a cost efficiency model, right? You know, you don't want, you know, seven seniors, and you don't need seven seniors, right? So- Right ...

40 MINS LATER

48:27
Yeah.
12:22
But what are the big, give me like two or three that you're seeing over and over that small business owners are making when it comes to software, tech, AI?
12:32
I'll say the first thing is really, and it's kind of like, you know, even at a big business when you've got an RFP, you know, certain companies, they go with, you know, the lowest cost provider.
12:43
You have to look longer term with software, right? Software isn't a one and done.
12:48
It really does require a lot of maintenance, right? There are new versions that come out.
12:51
There are new integrations.
12:53
your business changes, things need to adapt.
12:56
So you really have to make decisions about your software, not only about what I need for this defined window, right? I'm looking to get something released in September and here's the goal.

10 MINS LATER

22:41
So how do you define a forever company? What does that mean?
25:10
But why not go for the trifecta here? As we're talking about the emergent leader, what does that mean in the face of one of the biggest inflection points of our professional careers? And that seems like it's AI.
25:25
We all need to understand what the tools are, how they work.
25:29
and how they're limited.
25:30
That is another leader's responsibility.
25:33
We can't put it off to other people, right? It's going to impact every aspect of our business.
25:39
I think you mentioned before in terms of, you know, the jobs being changed by 2030.
25:45
I'll be honest, plenty of jobs are going to go away.
28:38
And I think the reality is, is somewhere in between.
0:32
Let's start by giving our listeners a little rundown of your career journey and what your current role is at First Factory.
0:42
Sure, I guess I have a fairly untraditional path into business leadership.
0:48
I graduated Stony Brook University as a theater major and didn't realize that there was so much about running a theater and plays and directing and managing people toward a unified effort that really would play out in business later.
1:03
After that, I worked at Kaplan Test Prep and Admissions for 18 years, everything from marketing and then running like center operations and then national operations, consolidating many business units for efficiency and scale and innovation.
1:20
And there was a period of time where there were bricks and mortar facilities that we had.
1:24
There were like 160 of them.
1:26
And we had those both for classroom space, but also for a training library.

6 MINS LATER

7:58
Yeah.
26:07
But, you know,
26:07
how many of us, you know, when we're listening to podcasts now play it on, you know, 1.x speed or more.
26:13
And so we're...
26:15
And AI is only speeding that up, right? I'm saving, on average, at least 15, 20 hours a week using AI as a research tool, as a forecasting tool, as, you know, a whole host of things.
26:25
But it doesn't mean that I'm working less.
26:29
It does a couple of things, right? Number one is it does let me get to, you know, the other things that are on my list that, you know, I wasn't getting to before.
26:35
So I'm accomplishing more.

5 MINS LATER

31:40
What are you noticing there? Like, how are you thinking about it at First Factory? And then since you have access to a pretty wide array of clients, you know, what are you noticing that you think is worthy of note? Well, I'm going to be a sober voice,
2:03
Uh, please give us the elevator pitch of your story.
2:07
Sure.
2:07
I have a bachelor's in theater, which is not necessarily the most direct path into business.
2:13
I bounced around the film industry for a few years, had some fun stints, but, you know, work was far and few between.
2:20
Uh, I ultimately landed at Kaplan in a marketing position.
2:23
Uh, part of the interview was an audition because we were giving presentations, and that was a pretty easy hurdle for me at the time.
2:30
And when I got there, um, I really only expected to spend, like, nine months or so, and was just impressed by the caliber of the people, you know, the, the intelligence, the compassion, and then there was just plenty of opportunity to contribute, um, and really put your fingerprints on the process and make things better.
7:47
Uh, what differentiates FirstFactory? Uh, what's the it factor?

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