CBS
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July 21, 2016 at 01:37 PM EDT

Before he decided to take Republican politics by storm, Donald Trump was known as a successful businessman and reality star. Who better to insult him, then, than Mark Cuban? After all, Cuban is a successful businessman who owns the Dallas Mavericks and is now the guy from Shark Tank. So when Cuban appeared on The Late Show Wednesday night, Stephen Colbert enlisted him for his Take the Gloves Off segment, during which they shared a round of insults against Trump.

“I’ve got a travel tip for you. When you’re going through customs and they ask if you have anything to declare, try not to blurt out ‘bankruptcy,'” Cuban said.

He continued: “Hey Donald, your companies fail so often, you must have gone to business school at Trump University.”

Like James Madison in Hamilton, Colbert acted as the hype man, pumping up the crowd and adding comments like “Oh, Donald, he just dumped you like one of your first two wives!”

Watch the clip below.

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