‘Hard work and community’: Lake County couple debuts Travelin’ Tom’s coffee truck

With their shaved ice truck stowed for winter, the enterprising Tcholakov family of Round Lake Beach has shifted to premium coffee and specialty beverages to offer at events throughout Lake County.

After attending training, picking up the truck and getting the needed health permits, Ivan and Jessica Tcholakov hit the road a few weeks ago with Travelin' Tom's Coffee of Grayslake, their second mobile food business.

The first, Kona Ice of Round Lake Beach, launched in July. In her early days as a publicist, Jessica Tcholakov’s first brand collaboration was the Kona franchise based in Florence, Kentucky.

Operating her own truck with Ivan and three kids became a personal milestone and longtime dream, Jessica Tcholakov said. So, after wrapping the shaved ice season near the end of October following a successful run, the couple are expanding their business.

Travelin’ Tom’s is a sister brand to Kona Ice, which was founded in 2007 by Tony Lamb with a single truck in northern Kentucky. More than 2,000 Kona Ice trucks operate across the country.

The first Travelin’ Tom’s franchises appeared in 2021 and now there are more than 300 trucks on the road. The Tcholakovs’ franchise is among a handful in the Chicago area and the only one in Lake County.

“After seeing the joy and impact Kona Ice brought to our community, expanding with Travelin’ Tom’s felt like a natural next step,” Jessica Tcholakov said.

They chose Round Lake for Kona because it’s Jessica Tcholakov’s hometown and was one of the few territories available in Lake County.

With an open slate in Lake County, Grayslake was chosen as home base for Travelin’ Tom’s because that’s where Ivan, who immigrated to the U.S. from Bulgaria at age 7, attended high school. Another connection was that their three children attended elementary and middle school there before the family moved back to Round Lake Beach, Jessica Tcholakov said.

Travelin’ Tom’s offers hot specialty drinks including cappuccino, mocha, cinnamon apple cider and spiced chai, and iced/frozen offerings including cold brew, frappe and iced latte.

“This journey is about opportunity, hard work and community,” Ivan Tcholakov said.

During the three-month Kona Ice season, the couple donated nearly $3,000 to local schools and nonprofits and plan on doing more for communities as Travelin’ Tom’s grows.

“We’re building something bigger than ourselves,” Jessica Tcholakov said. “These businesses allow us to show our kids what’s possible when you work hard, dream big and give back.”

Coffee brings people together in different everyday moments be it mornings at the train station, meetings, events, fundraisers and other ways, she added.

Travelin’ Tom’s has been at Hart’s Hill sled park, a Black Friday event and a parade last Saturday in Fox Lake for a young girl battling leukemia.

Next up is Frosty Fest at Viking Park in Gurnee on Jan. 10.