
Don Gregori
Chief Operating Officer of First Factory, author of The Emergent Leader, and AI Journal contributor
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Oct 12, 2026
Judgement Surge
8:06
8:16

Don GregoriGUEST
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.

Don GregoriGUEST
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
Why Your Tech Investment Needs a Profit Strategy | Don Gregori
12:22
12:32
12:43
12:48
12:56

Pam JordanHOST
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?

Don GregoriGUEST
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.

Don GregoriGUEST
You have to look longer term with software, right? Software isn't a one and done.

Don GregoriGUEST
It really does require a lot of maintenance, right? There are new versions that come out.

Don GregoriGUEST
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
Emergent Leadership Beats Overwhelm
25:10
25:33
25:39

Nick WestergaardHOST
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.

Don GregoriGUEST
We can't put it off to other people, right? It's going to impact every aspect of our business.

Don GregoriGUEST
I think you mentioned before in terms of, you know, the jobs being changed by 2030.
'The Emergent Leader'
0:48
1:03
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A
0:32Amanda AndrewsHOST
Let's start by giving our listeners a little rundown of your career journey and what your current role is at First Factory.

Don GregoriGUEST
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.

Don GregoriGUEST
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.

Don GregoriGUEST
And there was a period of time where there were bricks and mortar facilities that we had.
6 MINS LATER
The Emergent Leader with Author Don Gregori COO @ First Factory
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31:40

Don GregoriGUEST
how many of us, you know, when we're listening to podcasts now play it on, you know, 1.x speed or more.

Don GregoriGUEST
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.

Don GregoriGUEST
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.
5 MINS LATER

Mike PalmerHOST
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,
Why 80% of AI Projects Fail with Don Gregori
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Don GregoriGUEST
I have a bachelor's in theater, which is not necessarily the most direct path into business.

Don GregoriGUEST
I bounced around the film industry for a few years, had some fun stints, but, you know, work was far and few between.

Don GregoriGUEST
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.

Don GregoriGUEST
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.

