5. Copa Di Vino

• Entrepreneur: James Martin

• Product: Single-serve, ready-to-drink wine in a glass-like container.

• Deal: No deal (pitched twice, walked away both times).

• Why Unexpected: Despite not securing a deal, Copa Di Vino gained significant attention and sales due to its unique packaging and convenience, demonstrating the power of…

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4. The Original Comfy

• Entrepreneurs: Brian and Michael Speciale

• Product: A wearable blanket that combines the comfort of a blanket with the fit of an oversized hoodie.

• Deal: Barbara Corcoran invested $50,000 for 30% equity.

• Why Unexpected ?: Despite its simple concept, The Original Comfy turned into a huge success, becoming a…

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3. Tipsy Elves

• Entrepreneurs: Evan Mendelsohn and Nick Morton

• Product: Ugly Christmas sweaters and novelty clothing.

• Deal: Robert Herjavec invested $100,000 for 10% equity.

• Why Unexpected: ? Initially viewed as a niche product with limited seasonal appeal, Tipsy Elves expanded into a highly profitable business with year-round novelty apparel.

2. The Squatty Potty

• Entrepreneurs: Bobby Edwards and Judy Edwards

• Product: A toilet stool designed to improve bathroom posture for better elimination.

• Deal: Lori Greiner invested $350,000 for 10% equity.

• Why Unexpected: ?The Squatty Potty tackled a taboo subject with a straightforward and humorous approach, leading to massive sales and popularity.

1. I Want to Draw a Cat for You

• Entrepreneur: Steve Gadlin

• Product: Custom cat drawings for $9.95 each

• Deal: Mark Cuban invested $25,000 for 33% equity.

• Why Unexpected.? The concept of a business based on simple, hand-drawn cat illustrations seemed whimsical and unlikely to succeed, yet it captured Cuban’s interest.