In this podcast excerpt, Sam Parr and Sean discuss the strategy of acquiring small, stable "boring" businesses—such as pool construction firms and local internet service providers—owned by retiring baby‑boomers. They highlight the massive upcoming wealth transfer as boomers exit, leaving many profitable enterprises without successors, creating a market of undervalued assets that are too small for traditional private equity but too large for a solo entrepreneur. Sean explains how Enduring’s founders, Siva and Xavier, have rolled up nearly $100 million in revenue from an initial $2 million equity base by repeatedly buying and holding these cash‑flow businesses. Sean also shares his personal investment experience, receiving advisory shares that matched his capital, and notes that his stake has already appreciated roughly 20‑fold. Sam adds a personal anecdote about his own family’s small business and the emotional challenges of succession, underscoring the human side of this opportunity. The conversation blends market‑size observations, concrete acquisition examples, financial outcomes, and the emotional dynamics of business succession.
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They are buying— like, can we talk about what they bought?
They've come on the pod before, uh, and they're pretty public about stuff. So they're buying companies like pool construction companies. So it's like, uh, you know, pools are this like amazing business that you could, you could do. And they bought one in like— I think it's called Dolphin Pools or something like that. They bought it in Arizona. Crushes it. They hired this one operator who's like really good, who took it over from the original owner, the boomer owner, and basically it's grown like crazy, and that's like one of their cash cows now.
And I— and they also bought an internet web, like, um, I got— in the country, like, they don't have like AT&T or Time Warner or whatever. They, they have like local providers, and they bought one of those, and it's doing well. And I have family members, so my dad's an entrepreneur. They want like 5 kids.
They bought 5 different—
Yeah, a bunch of 'em.
Internet service providers.
And they're all doing, I think, pretty good. Um, and so my dad owns a small business that none of his family is taking over. My father-in-law owns a small business who, and it is a really, it's a killer business. I mean, um, and they, uh, he somehow the, our new brother-in-law is now gonna take it over and seeing the turmoil that he had to go through in order to, he was like, well, I spent 40 years, building this thing, and I guess if no one that I love wants it, I'm just gonna shut it down. Yeah, exactly. And, and it was like kind of tragic. And it's like, I'm literally willing to give this to a family member and they can make many millions of dollars a year if they wanted to do this. It's just, it's, it's free. You could have it. And, uh, people didn't wanna do it. And so I've seen this process and it is like an emotional it's a really— it's a huge challenge. And this is very, a very interesting market. There's some stats about how many— do you know how many boomers are retiring in like the next—
some absurd number.
It's absurd. It's like, it's like, it's like a quarter of the country, like, or, or a third of the country.
Biggest wealth transfers of all time is about to happen. It's the, like, that, that group of people, when they pass down their inheritance, it's gonna— it's like many trillions of dollars, I think. I don't know if that's— that might be hyperbole, but I think it's something like that. Some ridiculous number. And then that's like a lot of people that are just not gonna have to work, but also don't know what to do with it. And similarly, there's many, many businesses that was when Enduring first pitched it, they were like, they just showed me the stats. They were like, there are this many boomer businesses where they want to retire. They don't want to run their business anymore and their kids don't want to take it over. And like those businesses are up for grabs and they're like too small. Like they're not sexy as a startup and they're too small for big private equity. And so we're going to be like basically like permanent equity where they're going to be— they're just going to buy it and hold these amazing businesses for a very long time. And they keep doing that one after another. Like, I think Siva and Xavier, they've rolled up like almost $100 million of business equity off of a $2 million starting equity amount. Like, we— yeah, we—
it is crazy. I invested in what— I didn't have a lot of money when I first invested in, so— but at the time it was like like $10,000 or $15,000 or something like that that I invested. It was like, that was a big deal for me.
Did I tell you what happened with my investment in it?
It's just been like, it's just been growing and growing and growing. No.
So they, so they were like, they were like, Sean, like you've helped us like think through this idea. And like they knew like, I like this stuff. I'll be helpful along the way. So they're like, you know, we want to offer you, like if you invest, we'll also offer you like an invest, uh, an advisor or like, uh, like an advisory grant that'll just match your investment. And, uh, and I think they thought I was going to do like—
You forgot to file the paperwork.
No, no, no, no. I think they thought I was going to put in like $25K or like max or like K, something like that. So they're like, okay, cool, you got like 20K of equity, we'll give you 20K worth of advisory shares. But I was like a big believer in what they were doing, so I put in $200,000 and then they were like, they're like, oh. And I was like, look, you don't have to, like, I get it, you don't have to give me $200,000 of advisory shares. But Xavier was like, nope, a deal's a deal. And, um, like, I was like, if we didn't sign anything and like, dude, I'm totally okay with it. But he's like, no, like, like, we will, we'll honor that. And also like, I know you'll like, you'll deliver. And so since then, I've had this, like, immense desire to deliver on that. It was actually the best thing he ever did because he got me to basically work for him for free for this one. Like, for this act of goodwill, I am like, I will— I see your goodwill and I raise you 10 times goodwill on my own side.
It's going to— that's going to end up being a great— one of your better investments, I would think, depending on— I don't know when you got in.
Were you with— very—
we both— were you both? Yes. Then that's going to— I think it's going to crush.
Yeah, exactly. I think already, let's say conservatively, that's probably up 20x, you know, like something like that in valuation.
You think that's up 20x?
Because if they go raise now, they basically have— I don't know exact numbers, but like somewhere between $25 to $50 million of revenue, uh, closer to $50 million in revenue from these businesses now, um, that they've acquired off of $2 million in equity.
