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Mark Cuban

He can be bold and brash, but Mark Cuban is one of those rare entrepreneurs-turned-investors who can steer a new startup toward success. He juggles an ever-growing portfolio of businesses that now tops 80 ventures and sits as a judge on TV’s Shark Tank, a reality show where aspiring entrepreneurs pitch experts for investment.

So, how do you convince the Dallas Mavericks owner, worth an estimated $2.5 billion, to invest to your next big idea? “I look for unique products and companies that can be game changers in some cases or strategic to a theme I like or to another portfolio company,” Cuban wrote in an email to Entrepreneur.