Shark Tank Second Chance: Entrepreneurs Who’ve Appeared on Shark Tank Twice

Every season of Shark Tank sees thousands of hopeful entrepreneurs audition for the chance to stand in front of the Sharks and pitch their businesses. Some get lucky on their first try, while others have auditioned up to 7 times!

From those thousands, only a handful are chosen to pitch the Sharks, and from that handful, only a select few pitches actually make it to television. But some lucky entrepreneurs get that chance of a lifetime twice. Do they make the most of that second chance? Read on to find out!

Rebecca Rescate:

Citikitty(Season 2 Episode 9) & Hoodie Pillow (Season 4 Episode 25)

If anyone knows how to get in front of the Sharks, its Rebecca Rescate. In her first appearance, Rebecca pitched the Citikitty, a cat toilet training system that allows cat owners to quickly and effectively train their cats to use the toilet over time.When she appeared on Shark Tank for the first time, Rebecca had excellent sales figures, which immediately impressed the Shark and she was able to strike a deal with Kevin Harrington for $100,000 in exchange for 20% of her company.

Six years later, Rebecca became an investor and co-owner of another Shark Tank product: The Hoodie Pillow. The Hoodie Pillow became a fast success, and after appearing on Shark Tank a second time, Rebecca left with a deal from Robert Herjavec for $90,000 in exchange for 20% of the company. Both products are doing extremely well today and the company continues to sell on a massive scale.

Dave Alwan:

Echo Valley Meat (Season 4 Episode 21 & Season 6 Episode 22)

As a third-generation butcher and meat farmer, Dave Alwan mixes traditional butcher methods with high-quality meat processing to give customers the best of the best in meats. After opening his company, Echo Valley Meats, Dave appeared on season four of Shark Tank, seeking an investment that would help him amp up his ability to process online orders. Although the Sharks loved the meat samples, one by one they dropped out.

In between his appearances on Shark Tank, Dave launched an incredibly successful career in the meat industry, taking to heart the advice offered by the Sharks. On season six of Shark Tank, he won a deal with Mark Cuban for $150K in exchange for 25% of the company.

James Martin:

Copa Di Vino (Season 3 Episode 11 & Season 2 Episode 1)

Copa di Vino, ‘wine by the glass,’ is a patent created by James Martin. An Oregon native, James worked a farm that was left to him by his family. He loved to host parties but found the handling of corkscrews and fragile wine glasses to be difficult. He decided to create a pressure-sealed wine in a cup. After years of research and testing by top-of-the-line laboratories, James began the patent process on his wine in a cup.

During his pitch to the sharks in season two, Kevin O’Leary showed the most interest, but more so in the patent than the wine itself. He offered an investment toward the patent only, which James turned down. When James came on the show again one season later, he was no more successful landing a deal. However, by this point, his business was flourishing with deals in motion to land his product on the shelves of major retailers like Kroger.

Jason Woods:

Kymera ( Season 10 Episode 21 & Season 5 Episode 7)

Jason Woods is a Shark Tank success story if ever there was one. A California native, Jason created an electronic bodyboard that gives its users a fun ride on the water. Although the concept is fun and creative, Jason failed to get the product working and out on the market before his first appearance on Shark Tank. As a result, he had only prototypes to show the investors who one by one dropped out.

Despite this failure to make a deal, Jason took the advice of Mark Cuban and hired a partner to manage the business side of things. Several years later during his second appearance, Jason had working models to show the sharks, along with several new products. While sales were not soaring, the product had a promising future. Jason was able to land a deal with Robert Herjavec. This product is now sold in several marine retailers but is mostly accessible online.

Phil Black:

FitDeck (Season 5 Episode 15) & PrepWell (Season 11 Episode 18)

The FitDeck is a deck of cards that have an exercise on each card. The user can shuffle the deck to have a fun and effective workout, and each card has three difficulty levels ranging from easy to hard. Phil Black is the creator of this unique product, getting his inspiration from his career as a Navy Seal.

With the additional business sense lent to him by his Ivy League education, Phil was able to sell thousands of units prior to his appearance on Shark Tank. His downfall was investing most of the proceeds into developing a mobile app. After the episode aired, the product continued selling at fast rates. However, Phil eventually sold the company in an effort to help his sons prepare for high school and college. This is why he created PrepWell Academy, an online multi-week learning program that helps high schoolers prepare for college, careers, and the real world. Despite his enthusiasm, this idea failed to grasp the sharks’ attention or get Phil a deal. PrepWell Academy still offers a variety of programs for students that are preparing for the next step in their lives.