Comedian Tom Segura joined Joe Rogan for one of those sprawling podcast conversations that somehow ended up dissecting wealth, corporate tax strategy, and whether billionaires deserve all the hate they get. And the answer, according to Rogan, is complicated.

In a recent episode of "The Joe Rogan Experience," the two acknowledged that tax loopholes are real and shady as hell, but Rogan also made a case that not all ultra-wealthy people deserve to be lumped into the same villain category.

The Tax Loophole Problem

Segura kicked things off by pointing out how massive companies dodge taxes by shifting profits overseas. "They'll funnel it to Ireland and then not pay tax on it," he said. Rogan agreed that this is standard operating procedure for wealthy individuals and corporations. "Supposedly, that's what Jeffrey Epstein did for people. He helped people with tax loopholes and, you know, he helped rich people figure out how to save money," he added.

Segura wondered aloud whether these loopholes exist for a reason. Rogan didn't mince words: "They're scumbags. Yeah. They've all put it in place. They just want to make sure that they keep the most amount of money possible."

So far, pretty straightforward criticism. But then Rogan pivoted to a different angle.

In Defense of the Founder Billionaire

Despite calling out shady tax tactics, Rogan argued there's more nuance when it comes to billionaire founders who actually built something. "There's that thing where like 'no one should be a billionaire,'" Rogan said. "Well, okay, hang on. Do you like having a f***ing iPhone? Somebody had to make that. They're working 16 hours a day."

Rogan pointed out that people idolize tech leaders without understanding the personal toll. Nobody really wants to be Apple (AAPL) CEO Tim Cook or the late Apple co-founder Steve Jobs, he argued, adding that Jobs died young because of the intense pressure and workload.

Segura pushed back, noting that critics aren't always against success itself, but the inequality that comes with it. "These Amazon warehouse guys are like f***ing dying in the warehouse," he said. "You have the people at the top with like hundreds of billions of dollars. You can't trickle any of that down to some of your workers? That always seems like a legit complaint from people to me."

Segura mentioned that some of these employees earn as little as $15 an hour. Rogan countered that if the founder hadn't started the company, those jobs wouldn't exist at all. But then he added something interesting: they should "spread it around."

"Seems like probably better for everybody if you spread it around," he said. "Maybe people wouldn't hate you as much."

The Rare Humble Billionaires

The conversation turned to rare examples of billionaires who bucked the trend. Segura brought up Patagonia founder Yvon Chouinard, who gave up ownership of the company and its profits to fight climate change. Rogan appreciated that kind of move, joking, "He probably did mushrooms one day. He was like, 'What am I doing? I'm living in this prison.'"

Walmart (WMT) founder Sam Walton was another example of humility. Despite becoming the richest man in America in 1985, Walton lived modestly in Bentonville, Arkansas. Rogan read out his quote: "Why do I drive a pickup truck? What am I supposed to do? Haul my dogs around in a Rolls-Royce?"

But both comedians noted that Walton's kids and grandkids don't live the same way. "They're nepo babies," Rogan said. "That's not good. That's a tough way to live."

The Bottom Line

What makes this conversation interesting is that Rogan isn't taking a simple position. Yes, tax loopholes are scummy. Yes, billionaires should probably share more. But also, yes, building a massive company takes an insane amount of work, and the products these companies create have value.

It's the kind of nuanced take you don't often hear in the billionaire debate, which usually breaks down into "eat the rich" versus "they earned it." Rogan seems to be saying both things can be true: billionaires work incredibly hard, and they could afford to spread the wealth around more. And maybe if they did, people wouldn't be quite so angry about the whole thing.