Hey y’all, it’s Ian! Since I started as G & G Law’s Executive Legal Assistant, I’ve taken more notice of small businesses and their owners. Interacting with enthusiastic entrepreneurs on the daily will do that, I suppose, and what excites me most about our clients are their stories. Every enterprise is an extension of its founder; knowing the owner’s history and motivation, their business takes on a life of its own. I recently tripped over the fascinating roots of a curious Christmas business and couldn’t help but dig deeper.

For a few months every year, plazas and parking lots across Chicago flourish with fragrant forests of firs for festively focused families to find. They’re like Scrooge’s door-knocker, but cheery – rather than portending dread and indigestion, seasonal Christmas tree lots herald flurries of cheer, compassion, and hot chocolate. Not only that, they epitomize the small business model: find a niche and perfect it. WBEZ’s Curious City tells us more:


Rural Roots

The business sprouted in the early 1900s. Pioneers of the industry cut down wild trees and ferried them into Chicago, often selling them straight from their barges. Many lots still operate this way. Their old-timey practice of harvesting and shipping trees from yon wilderness retains its share of folksy charm, but struggles to keep up with discounts offered by big-box retailers like Home Depot.

Customers may see larger price tags, but these lots provide something that chain stores cannot: a singular experience. Wandering through rows of evergreens, breath swirling before your balaclava, one is transported to the forests of Germany, birthplace of the Tannenbaum tradition. With a higher price comes the added pride of authenticity. Not to mention, the chances of suddenly and regrettably finding yourself in the toilet aisle are significantly lower.


A Retrimmed Tradition

But despite the allure of the family-owned, schooner-shipped spruce, traditions must evolve to fit changing times. Ivy’s Christmas Trees is the perfect example. While pop flies ricochet around Wrigley Field, owner Ivy Speck uses her lot as game-time parking. And while the Cubbies hibernate for the winter, she shifts tack and keeps on chugging.

While Arneson grows and provides his own trees, Ivy imports hers from around the nation. Most are from neighboring states, but the treasured Frasier firs ship all the way from North Carolina. Without the overheads associated with maintaining a farm from year to year, her business is much more agile. Like her lot, Ivy can adapt and keep her business lucrative as the seasons change.


Tree’s Company

Curious City stopped there, but there’s a third species of tree lot with special relevance to our clientele: alliances between small businesses with unused outdoor space and nurseries yearning for urban expansion. Restaurants are particularly well-suited for such relationships – outdoor seating, closed and wasted during winter months, may find new purpose as a home for prowling tree farmers.

Take Tuco and Blondie, a Mexican joint in Lakeview. Co-founder Josh Rutherford was contacted by a provider interested in renting their patio and he jumped at the chance. In addition to the natural benefits of additional foot traffic, such as people buying a drink before braving the cold, it created unique marketing possibilities. Customers could meet the farmer, enjoy seasonal specials (Mexican hot chocolate for kids, plus a ‘spicier’ option for the grown-ups), and even shake mitts with Saint Nick himself! I tell ya, booking Santa is no mean feat. He’s a busy elf this time of year.

Picture from Tuco and Blondie (Facebook)

The North Pole comes to Southport!


Cedars in the Spotlight

I have one more tale to cap this post. A tree-topper, if you will. Farm-to-table eatery Uncommon Ground also brought beautiful boughs to the north side, but with a twist. Last winter, their Edgewater patio transformed into not just a tree lot, but into an outdoor theater! With seasonal changes come seasonal opportunities, and Chicagoans loathe to let such chances just pass by. Chock it up to Midwestern thriftiness. Uncommon Ground took advantage of the lot’s rare ambiance to premiere Pine, a play set – you guessed it – in a tree lot! Reviews were mixed (though they agreed that winter isn’t the time for outdoor theatre), but each critic was struck by the setting. I think The Fourth Walsh captured the magic:

“Trees, serving as theatre walls, with strings of holiday lights form an enchanting fort away from the cityscape. Carols playing muffle the street noises behind the trees. Even the full moon overhead cooperates to create a unique and magical Christmas fantasy.”

Scott Brooker, general manager at their Edgewater location, thoroughly enjoyed both the production and the overall arrangement. His staff loved the variety and it didn’t impede running the business. Uncommon Ground didn’t need any special licensing to play host; they provided the space, the tree farm brought the goods, and both reaped the benefits of their union.


Planting Your Seeds

Katie here, with an attorney’s perspective. We couldn’t help but wonder what formal steps someone would need to take to start a Christmas tree business in the city. After our last blog post, we wondered if these businesses are eligible for pop-up business licenses. Unfortunately, under Chicago’s new pop-up policy, outdoor businesses cannot receive pop-up licenses. Instead, they would have to obtain what’s called an “Itinerant Merchant License.” Any individual or business who occupies or leases for less than one year a fixed outdoor retail space for the sale of merchandise (like Christmas trees!) is eligible for an itinerant merchant license. You can apply for a license at City Hall, Room 800.

In addition to a specific license, all businesses should start with formal entity formation, for liability protection. There are many types of legal entities, but an LLC seems most appropriate for this type of business. If the tree seller desires to work with another business to utilize vacant space in order to sell their trees (such as a grocery store parking lot or restaurant patio), the two business owners will probably have to come to their own, private agreement for subleasing space to sell the trees.


(Ian again) Whether honoring the custom’s rustic roots or pivoting to suit an urban owner and clientele, Chicago’s tree lots bring special experiences to the city. Customers get to share season’s greetings with those they love. Businesses and farms can become the center of traditions that wouldn’t otherwise coalesce – Josh hopes that trees at Tuco and Blondie will become a neighborhood staple, and Scott’s phone has been ringing off the hook with evergreen inquiries. These lots impart a touch of green upon the concrete jungle, a piece of a provincial pastime inaccessible to city dwellers. And hang my holly if it doesn’t wreathe me in holiday spirit.


Interested in sprucing up your own business for the holidays? Contact us today for a complimentary consultation.


Special thanks to WBEZ for their fabulous reporting, and to Tuco and Blondie and Uncommon Ground for speaking to me for this story. Happy holidays!