After more than 350 on-air deals and eight seasons of tears, triumphs, and tense negotiations, Shark Tank is about to celebrate a new, nine-figure milestone.

In an episode slated to air tonight, the celebrity investors are expected to offer a deal that puts their total investment outlay at more than $100 million--a serious landmark for the investment show that wasn't an immediate hit. As for the entrepreneur who helps the Tank land its new high-water mark, nothing is known, other than that he or she is a Millennial.

Also, to be sure, there's no guarantee that that deal will stick. Nearly half of deals inked on Shark Tank fall apart after taping, according to research conducted by Forbes. For a variety of reasons--say a shark backs out or changes the terms of the deal in a way that irks the entrepreneur--deals often don't come to fruition. And, of course, some deals are just rejected outright. In 2015, the Kang sisters said no to billionaire investor Mark Cuban's proposal to buy their dating app, Coffee Meets Bagel, for $30 million.

What's more, some deals happen well after a company appears on Shark Tank. That's what happened to floral-delivery startup Bouqs.

Even so, multi-million dollar deals have become par for the course on the hit show. Here are eight of the biggest on-air, money deals to go through the Tank, along with some advice from the show's winners.

1. Zero Pollution Motors

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Musician Pat Boone and entrepreneur Ethan Tucker hold the record for accepting the largest deal in Shark Tank history. In 2015, the duo pitched a car that runs on compressed air made by the New Paltz, New York-based startup Zero Pollution Motors.

They agreed to give Shark Tank investor Robert Herjavec 50 percent equity and the opportunity to negotiate for the rights to bring the technology to the U.S. This was in exchange for $5 million.

The deal didn't close after taping, but Zero Pollution Motors CEO Shiva Vencat says there are other benefits to appearing on the show.

"Make the case for the deal but don't really expect anything from [the Sharks]. But expect the publicity," says Vencat, who did not appear on the episode. "I would advise people to go. At the end of the day, there is no such thing as bad publicity, there is just publicity."

2. SynDaver Labs

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Christopher Sakezles, the CEO of the synthetic human tissue and body-parts company, accepted Herjavec's offer of $3 million for 25 percent equity in 2015.

While the deal didn't close after taping, Sakezles didn't return to his Tampa headquarters empty-handed.

"It's a great experience for a couple different reasons. The No. 1 is to get an investment, and the other is exposure," says Sakezles. "You can buy [exposure], but small companies can't unless they have money for a Super Bowl ad."

Following the show, SynDaver Labs was featured on CBS's popular cop procedural, CSI. Sakezles said getting a product on national television gives an entrepreneur credibility with a wider audience.

3. Zipz Wine

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Andrew McMurray accepted an offer in 2014 from Shark Tank investor Kevin O'Leary that gave him $2.5 million in exchange for 10 percent of the single-serve wine company. O'Leary also noted he wanted the option to buy another $2.5 million worth of equity at the $25 million valuation.

McMurray, the national wine consultant for the company located in Brunswick, New Jersey, conferred with investors and accepted O'Leary's deal. He declined to explain how the deal may have changed after taping.

4. Ten Thirty One Productions

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Melissa Carbone didn't scare the Sharks away with her ghoulish characters or investment pitch in 2013. Cuban offered her $2 million in exchange for 20 percent of her Los Angeles-based entertainment company that focuses on the horror genre. Unlike most companies that accept deals on-air, the main aspects of her deal didn't change after taping.

5. Vengo

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Co-founders Steven Bofill and Brian Shimmerlik scored a huge deal for their digital vending machine company last year. Sharks Lori Greiner and O'Leary collectively offered them $2 million in venture debt, to be paid over three years at 7 percent interest, for 3 percent equity.

They accepted the deal, but whether or not the terms changed after they returned to headquarters in Long Island City, New York, is unknown.

6. Rugged Events

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Rob Dickens and Brad Scrudder, co-founders of the urban adventure and obstacle course company Rugged Races, inked their deal with Cuban in 2014. The billionaire investor offered the duo $1.75 million for 25 percent equity in the Boston-based company. The basic terms of their agreement did not change after taping.

Dickens says the key to getting large investments from Sharks is knowing your company's financial information so you can better negotiate.

"Make sure you have a 100 percent grasp on whatever is going on with your company," says Dickens. "If you know all your facts inside out, they can't rattle you, and you won't accept a lower offer than you should."

7. Sworkit:

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Cuban took an interest in the fitness app pitched by Ben Young and Greg Coleman in 2016. He offered them $1.5 million in exchange for 10 percent equity and $1.5 million worth of unsold advertisement inventory on the app.

The pair later told the Washington Business Journal that they didn't close the deal with Cuban after disagreements involving the value of the Rockville, Maryland-based company.

8. xCraft:

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JD Claridge and Charles Manning didn't just get a big deal; they got all the Sharks interested in their drone startup, xCraft. Cuban, O'Leary, Herjavec, Greiner, and Daymond John agreed to give the pair $1.5 million for 25 percent equity, split evenly between the investors, in 2015.

Their advice to fellow entrepreneurs? "If you think there is a possibility that you can bring in a big deal and close it, I would say, 'Go for it,'" says Claridge, the founder and CEO of the Coeur d'Alene, Idaho-based company. "Because of the big deal and because we brought all the Sharks in, that really doubled our exposure in a way."