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She spent her days at work and her nights building a brand — and ‘Shark Tank’ rewarded her with $250K

Ashley Sankar and her husband pitched their clothing startup, NineteenTwenty, to the Sharks and walked away with a massive deal

It appears that Ashley Sankar's multitasking turned out to be fruitful for her! For the unversed, Ashley worked nearly 10 to 15 hours at her day job every day. After wrapping up her day job, Ashley dedicated another six to eight hours to build her side business, and it seems like her hard work has finally paid off. During a November 2024 episode of 'Shark Tank' Season 16, Ashley, along with her husband and business partner Zach Sankar, pitched their clothing startup, NineteenTwenty, to the esteemed sharks Mark Cuban, Lori Greiner, Kevin O'Leary, Daniel Lubetzky, and Robert Herjavec.

Ashley and Zach's clothing brand, NineteenTwenty, creates convertible jackets that can be turned into tote bags, pillows, and blankets. The Sankars began their clothing company after realizing how costly the travel fees had become. The duo started selling their unique garments in December 2022, and Ashley stated that since then, they have made an annual revenue of $269,000 and expect to make $750,000 in sales. Along with this, Ashley also mentioned that they had earned $97,000 in lifetime profit.

Then, Ashley and Zach were seeking $250k in exchange for a 10% equity stake in NineteenTwenty. As per CNBC, Cuban shed light on the finances of their startup and said, "The numbers aren't adding up! One of the biggest challenges is fully understanding accounting and managing your cash flow. Because you want to say here that you’ve made $97,000 because it sounds good, but in reality, you didn’t make more than 82 [thousand], and it’s probably a lot less than that.”

Then, Ashley tried to defend the finances of her company by sharing that she and Zach work with financial consultants to arrive at their calculations. However, Cuban still wasn't convinced. Eventually, O'Leary made an offer of $250,000 for 30% equity to the Sankars, but he had an interesting condition: Ashley had to quit her day job and work on NineteenTwenty full-time.“You’re not 100% committed because you’ve got other jobs,” O'Leary told Ashley at that time.

Soon after, Herjavec chimed in, “That’s crap and it’s unfair. I started my first business — I didn’t know if it was going to work. I had to work a full-time job for six months.” When O'Leary remarked, “none of my CEOs” worked other jobs, Ashley responded, “They work 100% of the time, but they don’t work as much as I do.” Then, Herjavec promised the Sankars $250,000 for 25% of NineteenTwenty, and he told them, “You strike me as the kind of people [who are] going to figure it out."

Ashley tried to negotiate with Herjavec and asked him if he could lower the equity stake to 20%, but Herjavec declined. As per Daily Mail, Ashley broke down in tears and said, “I wish my mom would be able to see this.” For those wondering, Ashley's mother passed away when she was just 8 years old. In the end, the Sankars decided to accept Herjavec's offer, and they sealed the deal. Following that, Ashley exclaimed, "I’d rather have 70, 72% of something than have 100% of nothing. We came to make a deal.”