Aug 4, 2026 · 1 hr 49 min · 28 segments
From a live, in-person Chicago studio, we sit down with Tom Madine to unpack what real scale looks like in transportation, and why SMB shipping is still one of the most misunderstood corners of…
Tom MadineGuestAndrew SilverHostYes, it's interesting 'cause the other comparison I think of is, I was having this conversation with my father the other day, maybe a few weeks ago.
You know, I've got four months now left on my non-compete, and big question is, like, do I go start something from scratch, or do I buy something that's already operating?
And he's kind of against that, and he's like, "You know, I, I don't know why you would wanna buy someone else's trash, like, your, someone else's problems." And, and I'm like, "I get that." But then I realized, like, at Molo, we had plenty of our own trash and our own problems.
And there's certainly more control in building it yourself from scratch, but, uh, I think the advantage is, at least of entering the market in today's age, uh, with the Supreme Court stuff and just trying to, you know, onboard shippers that you, you have relationships with, it's way easier to do if you come in with an established business-

A- and we've done enough M&A, and they're, you usually [clears throat] because you didn't grow the business yourself, y- you, you go in and you're gonna scratch your head and look...

But, but there's this bias that you have of looking at, like, you know, we just did this deal with, you know, ShipStation now, where we and Octane come together.

So it's probably natural on both sides, you know, y- uh, yeah, look at, uh, you, you find something at the business that you weren't a part of, and you're like, "God, why are those guys doing it that way? That makes no sense." But then I look at my own business, and we got 30, you know, if, if they've got 100 things that are messed up, I got 101.

Um, I, I think the same is true of, like, franchise and agent, right? So, like, it's just, it's a, it's a different thing that you don't have the same level of direct control over.
Yes, it's interesting 'cause the other comparison I think of is, I was having this conversation with my father the other day, maybe a few weeks ago.
You know, I've got four months now left on my non-compete, and big question is, like, do I go start something from scratch, or do I buy something that's already operating?
And he's kind of against that, and he's like, "You know, I, I don't know why you would wanna buy someone else's trash, like, your, someone else's problems." And, and I'm like, "I get that." But then I realized, like, at Molo, we had plenty of our own trash and our own problems.
And there's certainly more control in building it yourself from scratch, but, uh, I think the advantage is, at least of entering the market in today's age, uh, with the Supreme Court stuff and just trying to, you know, onboard shippers that you, you have relationships with, it's way easier to do if you come in with an established business-

A- and we've done enough M&A, and they're, you usually [clears throat] because you didn't grow the business yourself, y- you, you go in and you're gonna scratch your head and look...

But, but there's this bias that you have of looking at, like, you know, we just did this deal with, you know, ShipStation now, where we and Octane come together.

So it's probably natural on both sides, you know, y- uh, yeah, look at, uh, you, you find something at the business that you weren't a part of, and you're like, "God, why are those guys doing it that way? That makes no sense." But then I look at my own business, and we got 30, you know, if, if they've got 100 things that are messed up, I got 101.

Um, I, I think the same is true of, like, franchise and agent, right? So, like, it's just, it's a, it's a different thing that you don't have the same level of direct control over.
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