Dec 22, 2025 · 34 min · 12 segments
In this episode of Money Mondays, Dan Fleyshman sits down with entrepreneur and educator Troy Millings to talk about building businesses, smart investing, and creating generational wealth. Troy sharesâŠ
Dan FleyshmanHost
And the whole concept for me with the Money Mondays, and I'm sure with your messaging and Market Mondays and the way you teach with kids, we know that it's important to talk about money in households, in communities, et cetera.

How can we change the narrative? What can we do, or what can people that are listening do to start having these conversations so people don't think it's rude to talk about money?
You know, I come from a West Indian background, and, uh, the only thing that we talked about was money was like, "Save it.
Save it." Or in fact, I would ask my mom to borrow money and she was like, "If you was money, I would spend you." It was like this running joke we had.
And I was like, "Th- that's all we're gonna talk about when it came to money?" Um, and so what I've been doing is I've been leading by example in that space, because, like, I am the, the, the generation of-
... curse breaker, right? And so, I've been super intentional about making sure that my kids understand what money is and how it works, right? So, the same things I used to teach to students, I now teach to my, my two children, right? You can do a couple of things with it, right? You can spend it.
Right? That is natural, right? (laughs) They, because they've seen it, they've been around that.
You can share it, which is something that we've learned, and they were part of church, right? We would tak- I used to take them to church all the times.
I haven't made it to m- to my church a- as much as we've been traveling, but they saw that, right? We, we were giving tithes every Sunday, right? Then the next piece was like, okay, you can invest it, which nobody talks about.
Right? And I was like, "Oh, there's something here." And so, leading by example and showing them that I was like, okay, well, I want them to see money, and so I would have money around the house, right? Like, I, I, when we'd give back i- in, during the Christmas time or when we were giving back to our kids, uh, throughout our program, I would put the money on the table and I'd have my kids count it.
I'm like, "Each envelope is getting $200." They're like, "Dad, there's 30 kids."I'm like, "Yeah, don't worry about that.
"... every envelope." And so now the thousands, like couple thousand dollars is there, it's not big money to them anymore.

And the whole concept for me with the Money Mondays, and I'm sure with your messaging and Market Mondays and the way you teach with kids, we know that it's important to talk about money in households, in communities, et cetera.

How can we change the narrative? What can we do, or what can people that are listening do to start having these conversations so people don't think it's rude to talk about money?
You know, I come from a West Indian background, and, uh, the only thing that we talked about was money was like, "Save it.
Save it." Or in fact, I would ask my mom to borrow money and she was like, "If you was money, I would spend you." It was like this running joke we had.
And I was like, "Th- that's all we're gonna talk about when it came to money?" Um, and so what I've been doing is I've been leading by example in that space, because, like, I am the, the, the generation of-
... curse breaker, right? And so, I've been super intentional about making sure that my kids understand what money is and how it works, right? So, the same things I used to teach to students, I now teach to my, my two children, right? You can do a couple of things with it, right? You can spend it.
Right? That is natural, right? (laughs) They, because they've seen it, they've been around that.
You can share it, which is something that we've learned, and they were part of church, right? We would tak- I used to take them to church all the times.
I haven't made it to m- to my church a- as much as we've been traveling, but they saw that, right? We, we were giving tithes every Sunday, right? Then the next piece was like, okay, you can invest it, which nobody talks about.
Right? And I was like, "Oh, there's something here." And so, leading by example and showing them that I was like, okay, well, I want them to see money, and so I would have money around the house, right? Like, I, I, when we'd give back i- in, during the Christmas time or when we were giving back to our kids, uh, throughout our program, I would put the money on the table and I'd have my kids count it.
I'm like, "Each envelope is getting $200." They're like, "Dad, there's 30 kids."I'm like, "Yeah, don't worry about that.
"... every envelope." And so now the thousands, like couple thousand dollars is there, it's not big money to them anymore.
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