"Economically, I like what he's doing," Cuban said on "Squawk Alley" from the sidelines of BTIG's 15th annual charity day in New York.
"[But] If you don't learn from history you're doomed to repeat it," the Dallas Mavericks owner and "Shark Tank" investor said. "Words matter, and I don't think he's figured that out yet."
Cuban, who supported Democrat Hillary Clinton during the presidential race, took President Donald Trump to task for saying he would be "honored" to meet with North Korean dictator Kim Jong Un under the "right circumstances," while saying that South Korea should pay for the THAAD advanced U.S. missile defense system.
White House National Security Advisor Lt. Gen. H.R. McMaster walked back Trump's statement, saying the U.S. would continue to pay for it.
Cuban did say Trump is a "great salesperson." The president had has positive interactions with world leaders, including Chinese President Xi Jinping, he added.
— Disclosure: CNBC owns the exclusive off-network cable rights to "Shark Tank."