Marketdash
Back to Stock Market News

Mark Cuban's Shark Tank Nightmare: How Free Shipping Killed a $100K Chocolate Pretzel Deal

MarketDash Editorial Team
2 days ago
Mark Cuban invested $100,000 in The Painted Pretzel on Shark Tank, only to watch it become one of his most frustrating deals. The culprit? A free shipping offer that turned every $29.95 sale into a $1 loss. Despite 1,500% growth after the show aired, the company's broken economics eventually led to its closure.

Mark Cuban has closed hundreds of deals on Shark Tank, but there's one chocolate-covered disaster that still haunts him. Speaking at Oxford Union in 2017, he described a company that "still drives him crazy" without naming names. The math was brutal: product sold for $29.95, cost about $14 to make, and came with free shipping that cost the business $16 per order. Every single sale lost a dollar. "Cash is going like this," Cuban said, gesturing to show how quickly money vanished. "She should've killed it."

He didn't mention the company by name, but the details match The Painted Pretzel, founded by Raven Thomas. Back in 2012, Thomas walked into the Tank asking for $100,000 in exchange for 25% equity. Cuban handed it over immediately, impressed by her drive and the product itself.

From Kitchen Experiment to Shark Tank

Thomas started making chocolate-dipped pretzels in her Scottsdale, Arizona kitchen as gifts. People loved them. Requests started pouring in. Eventually her kitchen couldn't keep up, and she found herself turning down massive orders, including a $2 million one from Sam's Club. That's when she knew she needed serious help and applied to Shark Tank.

The Shark Tank effect hit hard. In a 2016 interview with WAGS Redefined, Thomas revealed that her website crashed the moment her episode aired. "My business grew 1,500%," she said. "It was wonderful and terrible at the same time because it was just so much to deal with." Millions of viewers meant phones ringing, emails flooding in, and orders exploding overnight. The business went into hyperdrive.

Scaling Pains and Operational Chaos

But growth isn't the same as profitability. Thomas admitted the experience was chaotic and required rapid manufacturing expansion. Most production moved to a large candy facility, though she stayed deeply involved. "I'm very involved, and I'm a perfectionist," she explained. As for Cuban? He wasn't managing daily operations but remained available when needed. "He has a million people who work for him... it's readily available," she said.

Here's where the business model started breaking down. While Cuban pointed to free shipping as the fatal flaw, Thomas prioritized customer satisfaction above all else. Noble goal, terrible economics. The margins collapsed, and the company started hemorrhaging cash with every order.

The Death Spiral

During his Oxford talk, Cuban grouped the chocolate pretzel company with several businesses that "have gone out of business but aren't smart enough to know it." He didn't trash the product. In fact, he told Food Republic in 2015 that the brand had real potential with proper support. But the business model? Completely broken.

Warning signs started appearing. According to Food Republic, The Painted Pretzel's Yelp page filled with complaints about long delays, order problems, poor communication, and unfulfilled shipments. Some customers filed Better Business Bureau complaints after waiting weeks without updates. The company's own FAQ admitted orders could take up to a month to arrive.

By 2025, Yelp listed The Painted Pretzel as closed.

Resilience Versus Reality

In that same WAGS interview, Thomas showed no fear of failure. "I've failed many times in business, and I think that's big," she said. "That is resilience." When she first pitched the Sharks, she wasn't nervous about the presentation. She just didn't want to trip walking down the hallway. Her audition video was a one-take wonder filmed in her kitchen by her husband and sent off without edits.

Thomas had zero pretense about her business. "Why would they pick me? I just make chocolate-covered pretzels," she remembered thinking. But Cuban saw something deeper. "You're putting your heart, your soul, and your love into it," he said on the show, defending her against Kevin O'Leary's dismissive comments. "And you care about the business."

But here's the harsh truth: caring doesn't fix a balance sheet.

The Painted Pretzel had everything going for it. Product-market fit? Check. Massive publicity? Check. A resilient founder? Absolutely. But none of that matters when your unit economics are underwater. The company collapsed under unsustainable margins, logistical strain, and systems that couldn't scale.

The product was beloved. The founder was tough. The investor was engaged. But the business, plain and simple, didn't work.

Back to Stock Market News

Mark Cuban's Shark Tank Nightmare: How Free Shipping Killed a $100K Chocolate Pretzel Deal

MarketDash Editorial Team
2 days ago
Mark Cuban invested $100,000 in The Painted Pretzel on Shark Tank, only to watch it become one of his most frustrating deals. The culprit? A free shipping offer that turned every $29.95 sale into a $1 loss. Despite 1,500% growth after the show aired, the company's broken economics eventually led to its closure.

Mark Cuban has closed hundreds of deals on Shark Tank, but there's one chocolate-covered disaster that still haunts him. Speaking at Oxford Union in 2017, he described a company that "still drives him crazy" without naming names. The math was brutal: product sold for $29.95, cost about $14 to make, and came with free shipping that cost the business $16 per order. Every single sale lost a dollar. "Cash is going like this," Cuban said, gesturing to show how quickly money vanished. "She should've killed it."

He didn't mention the company by name, but the details match The Painted Pretzel, founded by Raven Thomas. Back in 2012, Thomas walked into the Tank asking for $100,000 in exchange for 25% equity. Cuban handed it over immediately, impressed by her drive and the product itself.

From Kitchen Experiment to Shark Tank

Thomas started making chocolate-dipped pretzels in her Scottsdale, Arizona kitchen as gifts. People loved them. Requests started pouring in. Eventually her kitchen couldn't keep up, and she found herself turning down massive orders, including a $2 million one from Sam's Club. That's when she knew she needed serious help and applied to Shark Tank.

The Shark Tank effect hit hard. In a 2016 interview with WAGS Redefined, Thomas revealed that her website crashed the moment her episode aired. "My business grew 1,500%," she said. "It was wonderful and terrible at the same time because it was just so much to deal with." Millions of viewers meant phones ringing, emails flooding in, and orders exploding overnight. The business went into hyperdrive.

Scaling Pains and Operational Chaos

But growth isn't the same as profitability. Thomas admitted the experience was chaotic and required rapid manufacturing expansion. Most production moved to a large candy facility, though she stayed deeply involved. "I'm very involved, and I'm a perfectionist," she explained. As for Cuban? He wasn't managing daily operations but remained available when needed. "He has a million people who work for him... it's readily available," she said.

Here's where the business model started breaking down. While Cuban pointed to free shipping as the fatal flaw, Thomas prioritized customer satisfaction above all else. Noble goal, terrible economics. The margins collapsed, and the company started hemorrhaging cash with every order.

The Death Spiral

During his Oxford talk, Cuban grouped the chocolate pretzel company with several businesses that "have gone out of business but aren't smart enough to know it." He didn't trash the product. In fact, he told Food Republic in 2015 that the brand had real potential with proper support. But the business model? Completely broken.

Warning signs started appearing. According to Food Republic, The Painted Pretzel's Yelp page filled with complaints about long delays, order problems, poor communication, and unfulfilled shipments. Some customers filed Better Business Bureau complaints after waiting weeks without updates. The company's own FAQ admitted orders could take up to a month to arrive.

By 2025, Yelp listed The Painted Pretzel as closed.

Resilience Versus Reality

In that same WAGS interview, Thomas showed no fear of failure. "I've failed many times in business, and I think that's big," she said. "That is resilience." When she first pitched the Sharks, she wasn't nervous about the presentation. She just didn't want to trip walking down the hallway. Her audition video was a one-take wonder filmed in her kitchen by her husband and sent off without edits.

Thomas had zero pretense about her business. "Why would they pick me? I just make chocolate-covered pretzels," she remembered thinking. But Cuban saw something deeper. "You're putting your heart, your soul, and your love into it," he said on the show, defending her against Kevin O'Leary's dismissive comments. "And you care about the business."

But here's the harsh truth: caring doesn't fix a balance sheet.

The Painted Pretzel had everything going for it. Product-market fit? Check. Massive publicity? Check. A resilient founder? Absolutely. But none of that matters when your unit economics are underwater. The company collapsed under unsustainable margins, logistical strain, and systems that couldn't scale.

The product was beloved. The founder was tough. The investor was engaged. But the business, plain and simple, didn't work.