The Christmas Carolers, an entertainment company based in Alabama, nabbed a $250,000 deal on “Shark Tank” this week, but there was an unexpected twist.
Owner Kenyon Ross and “head elf” Jessica Harris appeared on the ABC reality series on Wednesday, Dec. 10, as part of a holiday themed episode called “Cash or Coal?: The Sharks Get Into the Holiday Spirit with Festive Pitches & Products.”
Their pitch to the celebrity investors — Barbara Corcoran, Daymond John, Lori Greiner, Daniel Lubetzky and Kevin O’Leary — featured a cappella singers in Victorian-style costumes, warbling Christmas tunes in a merry manner. Ebenezer Scrooge was on hand, as well, adding a classic “Bah, humbug!”
As Ross and Harris explained to the sharks, The Christmas Carolers provides costumed caroling groups for parties and corporate events, with a starting rate of $700 for the first hour. The company, based in Hoover, was founded by Ross in 1996, and has expanded to 14 cities over the past 30 years.
“It’s the most wonderful time of the year and people are craving something real,” Ross said. “Moments that bring us together. And that’s exactly what The Christmas Carolers has to offer. Who wants to be a part of bringing harmony back to the holidays?”
Ross and Harris were seeking a $250,000 investment from the high-powered celebs, in exchange for 20% of the company. Their goal, they said, is to expand The Christmas Carolers’ reach to 50 cities across the country.
“Sharks, I know I wouldn’t want to be visited by the ghost of missed opportunities,” Ross said. “So don’t let this slip you by.”
Although the investors appeared charmed by the troupe’s performance — and they noted the enthusiasm and commitment of Ross and Harris — they had some nitty-gritty questions about the seasonal company.
In particular, the sharks seemed flummoxed that The Christmas Carolers have just “hundreds of followers” on social media. Also, the investors were unimpressed by the sales numbers Ross mentioned: more than $1 million total over the lifetime of the company.
“Since 1996, he’s made over a million,” John said. “I could have said that about working at Red Lobster.”
Ross explained that The Christmas Carolers is a passion project for him — he makes his living as a full-time medical sales rep — and he projected a bump to $1 million in gross profit over a single year, up from $255,000 in 2024, if the company expands to 50 cities.

Under more grilling from the sharks, Ross said The Christmas Carolers made a 20% net profit in 2024, which O’Leary quickly estimated at $50,000. Ross added that he takes no salary from the company, and Harris works part-time as head elf.
The overall business plan did not sit well with the investors, and they had some blunt words about the company.
“I think your projections are actually very achievable,” Lubetzky said, ”as long as we’re talking about doing them in an alternative dimension.”
Ouch! But Lubetzky softened the blow with kudos for Ross and Harris.
“Am I right that what fuels you is that you just love what you do?,” Lubetzky said. “It’s pretty clear to me that you just have fun and you’re enjoying the ride. I really think this is really beautiful, but it’s not really investable.”
He passed on the deal, and three more investors — John, Greiner and O’Leary — followed suit. Then Corcoran jumped in, almost like Santa down the chimney.
She offered to buy the company for $125,000 cash, taking 100 percent of the stock. Corcoran sweetened the deal with a $125,000 loan, “to see the business through to success.” She also promised to boost The Christmas Carolers’ social media profile in a big way.
“I’m making you the chairman of the board,” Corcoran told Ross. “You’re going to go home with $125,000 in your pocket, and still have your day-to-day or every-other-week involvement or whatever you want.”
Ross, who appeared taken aback by her counter-offer, said he was unwilling to give up ownership of the company he founded.
“I really need to have the control, I must say, to bring it to what it’s supposed be,” Ross said. He also said he wanted to change Harris’ role to full-time, bringing her in as a partner.
After some negotiations, Ross and Corcoran settled on a deal: She would buy The Christmas Carolers for $125,000, taking 60 percent of the stock. Ross would get 30% of the stock and Harris would receive 10%. Corcoran added a $125,000 line of credit for the company, helping with expansion to other cities.

“This deal was really unexpected,” Ross said. “I don’t know if you can see it on my face. I did not expect to be, want to be, purchased out. So I’m glad we got to the terms that were agreeable for me.”
“And I got more money!” Harris said.
Performers for The Christmas Carolers celebrated the deal with a brief rendition of the “Hallelujah” chorus, and O’Leary put a capper on the episode with his unvarnished opinion.
“Barbara, it hit me,” O’Leary said. “It’s a Christmas miracle!”
