The Christmas Carolers - Shark Tank Update

The Christmas Carolers entered the holiday-themed Tank asking for $250,000 for 20%, presenting a business built entirely around premium Victorian-style caroling experiences for corporate events and private homes. Founded in 1996, the company has spent decades perfecting their nostalgic, costumed, a cappella performances, which are booked online and delivered by trained singers carefully selected from music and theater programs across the country.

While the service delivers undeniable Christmas magic, the sharks immediately raised the obvious concern: this is a strictly seasonal business. The founder confirmed as much, noting that despite their beautifully crafted performances and polished production, social media presence was limited to only “hundreds” of followers, and that most of their revenue still came from corporate party clients.

Performances average two hours, starting at $700 for the first hour-of which the carolers take home $230, translating to roughly $40–50 per hour per singer-with additional hours priced more affordably. Despite being in business nearly three decades, lifetime sales were just over $1 million, prompting a bit of playful ribbing from the sharks over the long runway.

But recent years told a more compelling story: $60,000 three years ago, $90,000 the next, then a jump to $255,000 last year, and a projection of $1 million for the current season thanks to a major expansion from 14 to 50 cities. That aggressive nationwide growth plan was the reason he came seeking a shark’s help.

Still, many sharks bowed out, saying they didn’t “get it” or didn’t see it as investable. Barbara, however, recognized the charm, the momentum, and the operational discipline behind scaling live entertainment.

She first offered $125,000 for 100% of the company plus a $125,000 loan, allowing the founder to remain chairman and involved as much as he wished, but he wasn’t willing to give up full ownership and countered at 50%. After more sharks stepped away and the tension rose, Barbara made one final offer: $125,000 in cash and a $125,000 loan for 60%.

Believing she could turn The Christmas Carolers into the go-to brand for holiday entertainment nationwide, she and the founder struck a deal, sealing a partnership to spread even more Christmas cheer.

Kenyon Ross and Jessica Harris’s Victorian-era caroling company entered the Tank as a deeply seasonal entertainment business, and post-show momentum has focused on scaling that niche with new bookings and broader geographic reach. Following their pitch and deal with Barbara Corcoran, The Christmas Carolers have been gearing up for an expanded 2026 season, with performances available in dozens of cities and interest from private events and corporate clients rising as holiday bookings open.

The company’s seasonal model - with packages that range by ensemble size and premium dates - continues to draw customers who want nostalgic, live holiday entertainment, and the Sharks’ spotlight has helped elevate awareness in markets across the U.S. While its revenue still concentrates in the winter months, The Christmas Carolers have amplified recruitment and brand exposure, reinforcing their role as a go-to for festive experiences.