What does it mean to be an audacious entrepreneur? Ask Mark Cuban, he ought to know. The Shark Tank star and Dallas Mavericks owner is known for being bold, irreverent, and--yes--cocky in his business dealings. Read on for five classic Cuban moments. 

1. Trolling Yahoo. 

Cuban and his partners sold Broadcast.com to Yahoo in spring 1999 for a hefty $5.7 billion, which made Cuban a billionaire. Maybe it was worth it, but the audio product eventually disappeared from Yahoo's offerings.

2. Always the Maverick. 

Since buying a controlling stake of the NBA's Dallas Mavericks in 2000, Cuban has been fined 20 times by the league--a total of $2 million--mostly for criticizing officiating. This year, he said he wanted one last fine from outgoing commissioner David Stern; he got his wish, for $100,000.

3. Swimming with Sharks. 

Forget the show-biz convention of air kissing your co-stars. Cuban says the tension on the five-season ABC show Shark Tank is real: "Trust me, there are times when you just want to reach over and punch Kevin or Lori."

4. Taunting Regulators. 

Many people would be quietly grateful if they were cleared of an insider trading charge. But when a federal jury acquitted Cuban in 2013 for a questionable stock sale, Cuban challenged the SEC to "treat American citizens the way they should be treated."

5. Playing Trump's Cards. 

The two TV billionaires have been sparring for most of the 21st century, but Cuban's cheekiest jab came in 2012, when he offered Donald Trump $1 million to shave his head for charity. Whatever is atop Trump's head stayed intact.