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Ryan Oleary

Ryan Oleary

Aug 14, 2026

32:18
Mm-hmm.
32:18
Uh, you need to understand what's, what's more important, uh, whenever you have your business built.
32:24
Uh, what's more important? Is that base salary the most important with your income structure, or is that commission actually the most important thing? Um, what are you, what are you trying to grow? What are you trying to, you know, actually accomplish down the, the future and, and make, you know, into your prime business?
32:45
Yeah.
32:45
So, um, that's what I would, you know, look at.
32:49
You know, you, you're taking a look into your benefit structures and, um, you're working with your HR.
32:55
And you figure out, uh, how much you're actually covered, and whenever you know how much you're covered, you need to understand, "Can I live off that, uh, if anything were to happen to me?" I know I'm in the office and I'm, you know, driving to work, driving back from work, not really on the road with a truck.
33:13
But, uh, uh, you just have to make sure that, you know, whenever you're a broker and you're building something from nothing, you gotta make sure that those, those steps, those, those next goals and levels that you're achieving, that are all covered behind you.
32:48
Mm-hmm.
32:48
Uh, you need to understand what's, what's more important, uh, whenever you have your business built.
32:54
Uh, what's more important? Is that base salary the most important with your income structure, or is that commission actually the most important thing? Um, what are you, what are you trying to grow? What are you trying to, you know, actually accomplish down the, the future and, and make, you know, into your prime business?
33:15
Yeah.
33:15
So, um, that's what I would, you know, look at.
33:19
You know, you're, you're taking a look into your benefit structures and, um, you're working with your HR, and you figure out, uh, how much you're actually covered.
33:30
And whenever you know how much you're covered, you need to understand, "Can I live off that, uh, if anything were to happen to me?" I know I'm in the office and I'm, you know, driving to work, driving back from work, not really on the road with a truck.
33:43
But, uh, uh, you just have to make sure that, you know, whenever you're a broker and you're building something from nothing, you gotta make sure that those, those steps, those, those next goals and levels that you're achieving, that are all covered behind you.
7:16
Whoever wants to go first, I'm going to let you guys make the decision.
7:20
Yeah, I mean, I think we both can all like start it off and talk a little bit about, you know, the business and kind of how it started and kind of what my role was.
7:30
And then, you know, Chris can obviously talk about, you know, the impact that she had as well and helping us kind of scale it.
7:38
So your real background is like I worked in the payment processing industry before.
7:47
for, I guess, well, it was about 21 years.
7:50
And so, and specifically in payment processing, I was in, you know, I worked with a couple larger than multinationals like JP Morton Chase, Fiserv, like in a business development capacity.
8:05
So I was like originally hired as a sales representative um to basically work with small business so small and then you know small to medium-sized business and set them up so that they could process visa mastercard american express um either online or in person or through integrated platform and so i was hired as a representative here in in nova scotia working with small business um and it did quite well as an individual sales rep And I really done that right until 2016.
11:24
For
139:35
What was sort of like the next couple years like?
139:40
So I ended up leaving, so th- so by August...
139:47
So aft- after the boat operations, I ended up leaving the legion.
139:52
Um, and my guys continued on into, like, the unit I was with continued on into, uh, Severodonetsk-And then Bakhmut and some other stuff, whereas I transitioned over into, uh, back doing just like dro- some drone stuff, to be quite honest.
140:10
Um, at that point in the war, you could start to see that it was going to s- like the Russians were still obviously pushing areas, but it was turning into more of a, a static line defense type stuff.
140:27
Um, but I, I honestly, I left that unit because that boat op, I was just...
140:33
I, they were gonna keep doing 'em, and I was like, "I am like, I'm over it." So I went back and started doing drone operations.

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