CNBC's Jim Cramer broke down why investors must take a chance on a stock when the chief executive of the underlying company is being transparent. The "Mad Money" host sat down with the heads of Penn National Gaming and Barstool Sports to discuss the two companies' bet on sports gambling.

CNBC's Jim Cramer said Wednesday that investors can miss out on gains when companies have "embraced radical transparency" and investors fail to see the truth for what it is.

"It's easy to assume everyone in this business is totally cynical, but taking that approach kept you out of some monster gains in and in ," the "Mad Money" host said. "Some CEOs have earned the benefit of the doubt, and you should give it to them."

Barstool Sports founder David Portnoy told CNBC he has his eyes set on owning a sports team after the sports and pop culture blog landed a nine-figure partnership with .

The deal "is so big, I'm trying to get to, like, buy [a] sports team-type mogul," he said in an interview with Cramer, appearing alongside Barstool CEO Erika Nardini and Penn National CEO Jay Snowden on "Mad Money."

Portnoy did not say what kind of sports team or professional level he would like to gain ownership in, but he is placing a bet that the partnership makes progress toward that goal.

"This is hopefully what's going to take us there. I believe in it a million percent," he said.

In Cramer's lighting round, the "Mad Money" opined on viewers' top stock picks of the day.

: "You know, I didn't think the quarter was nearly as bad as the stock reacted. The stock's down $1.50, yields 5.6%. I think the yield's safe. I'm actually a buyer here."

: "They missed the quarter badly in a quarter in a market where semiconductors are all hitting it out of the park, so I have to say stay away."

: "Count me as a speculative buyer."

Disclosure: Cramer's charitable trust owns shares of Apple.