Shark Tank star Robert Herjavec stunned viewers in May by making a handshake deal to invest $5 million in Zero Pollution Motors, maker of a $10,000 plastic minicar that runs on compressed air. The deal would have doubled the previous record for the largest Shark Tank investment ever, but ultimately fell apart during the due diligence process. Still, a handful of entrepreneurs have successfully attracted million-dollar investments from the Sharks. Here are the five largest deals made on Shark Tank in which money actually wound up exchanging hands.

5. Breathometer: $1 million

Entrepreneur Charles Michael Yim made history in more ways than one during season five of Shark Tank. On top of landing the show's largest deal at the time--$1 million for his smartphone breath-analysis company Breathometer--Lim was the first to partner with all five Sharks. Mark Cuban paid $500,000 for 15 percent of the company, while Lori Greiner, Robert Herjavec, Daymond John, and Kevin O'Leary split the remaining $500,000 investment. The 30 percent equity stake Lim gave up seems to have been worth it: A year after the segment aired on the show, Breathometer's sales hit nearly $10 million, up from $1 million just a few months earlier.

4. BeatBox Beverages: $1 million

Austin, Texas-based BeatBox Beverages didn't reinvent the wheel with its product, wine in a neon-colored package designed to look like a boombox. But Justin Fenchel and his co-founders did walk out of the tank during season six with a huge check from Mark Cuban. They initially asked for $250,000 for 10 percent equity, but ended up with a much sweeter deal: $1 million for a third of the company. Sales reportedly have surged following the business's appearance on the show last October.

3. Rugged Events: $1.75 million

The founders of Rugged Events, which hosts of a five-kilometer race through a muddy course called the Rugged Maniac Obstacle Race, entered the tank during season five seeking $1 million for 10 percent equity. After fielding multiple offers for a piece of the company, which had $4.2 million in annual sales at the time, co-founders Rob Dickens and Brad Scudder accepted $1.75 million for 25 percent from Mark Cuban. Since then, revenue reportedly has grown by $1 million.

2. Ten Thirty One Productions: $2 million

In season five, entrepreneur Melissa Carbone struck a $2 million deal with Mark Cuban for 20 percent of her horror entertainment company, Ten Thirty One Productions, claiming what was then the largest deal ever on Shark Tank. With Cuban's help, Carbone's business, which creates and produces live Halloween-themed attractions, inked a partnership with Ticketmaster and received a separate investment from Live Nation, the largest concert company in the country.

1. Zipz: $2.5 million

Kevin O'Leary, aka "Mr. Wonderful," struck the largest deal in Shark Tank history during season six by loaning the single-serve wine company Zipz $2.5 million in exchange for 10 percent equity. O'Leary even negotiated the right to buy another $2.5 million worth of equity from Zipz founder Andrew McMurray at the same valuation in the event of an exit. The deal went through, and O'Leary says he expects the company to have a game-changing impact on the U.S. beverage market, though it likely will take several years.

Published on: Jun 24, 2015