How This Christmas Tree Seller Spreads Holiday Cheer With Square

How This Christmas Tree Seller Spreads Holiday Cheer With Square
Greg Walsh has been selling Christmas trees in New York City for 35 years, learn how he does it with Square.
by Nina Godlewski Dec 15, 2023 — 4 min read
How This Christmas Tree Seller Spreads Holiday Cheer With Square

Every November, Christmas tree stands pop up across New York City seemingly overnight. And every year, New Yorkers head to the nearest one to pick up a tree. To give you a sense of scale, 58,000 trees were recycled across the five boroughs after the 2022 holiday, according to the New York City Parks Department.

All those trees have to be trucked into the city to be sold, many of them by Christmas tree business owners and operators like Greg Walsh of Greg’s Trees. The long-time tree seller operates seven stands across Brooklyn and Queens and uses Square to serve his many customers.

Adjusting to changing times

Just like any business, Christmas tree sales have their ups and downs, and the market changes from year to year. This year, 20% of respondents surveyed by the Real Christmas Tree Board said they were planning to buy a real tree for the first time.

In addition to more people buying real trees, the time of year when people buy trees has changed, too. Unlike earlier years, customers don’t tend to buy trees at night, and trees are bought earlier in November than ever, Walsh said. This trend isn’t specific to New York City. People have been buying trees sooner and decorating sooner. “We kind of like it; it’s really nice to be breaking even by December 1,” Walsh said. “We used to break even December 18.”

That means inventory management and sourcing are key. To meet this demand, each year he buys five trailers worth of trees and about 1,000 wreaths to sell at his stands. He buys with the goal of having some inventory left by Christmas. “We don’t aim to run out completely. The last couple of days people still want choices and all in all it is usually only 2% left over,” he said. 

He works to source his trees from farms in Tennessee, North Carolina, Oregon, Washington, and even from Canada, specifically the Quebec and Nova Scotia areas. “I personally go to all the farms every couple of years,” Walsh said.

Payment flexibility for the holiday season

The National Christmas Tree Association estimates that 25 to 30 million real Christmas trees are sold every year across the United States, making it lucrative for those who can weather the difficulties of running a seasonal business. But running a business requires flexibility when it comes to accepting payments, something Walsh found out early on in his time as an entrepreneur.

“I had a lot of trouble with the other ones [point of sales],” he said. Before he started using Square, he would have issues completing payments and dealing with chargebacks after the selling season was complete. “We never get that with Square,” Walsh said.

He’s been selling Christmas trees in New York City for 35 years, mostly as a side hustle. He worked full-time in education, focusing on tree sales after the school day ended.

For the last 15 years, he has been running seven or so stands each year, using Square to take payments, and working with employees who return each holiday season. “We have a great group of guys who return every year,” he said of the staff who all help him run the stands.



A Greg's Trees Christmas tree stand in New York City.

Many of Walsh’s customers are New Yorkers looking to bring a tree home to add some holiday cheer to their apartments. But some of Walsh’s largest sales are from corporate clients that need large orders of wreaths, trees, and the like. “We love Square Invoices,” he said. “Some of the really, really good sales are commercial. Like, ‘Hey, I need 15 wreaths; I need three big trees for a building; but I need a receipt.’ They don’t want some scribbled scrap of paper,” Walsh said. So he sends an invoice over, and his clients love it, “They’re like, ‘Oh my God, this is so beautiful!’” he said.

And for those customers who do pay on the spot, he says they rarely ever swipe credit cards anymore. “We’re at zero cards that are being put in the machine anymore. I don’t think anybody does that anymore. They all tap it, use their phone, their watch. To me, it’s all amazing,” he said. 

Standing out in a forest of tree sellers

In such an early and competitive market, with other sellers meeting the demand too, he found a way to set his business apart. “We decided seven, eight years ago to brand it. Nobody else does this in New York. You see these tree stands. You think they’re independent? They’re not independent,” Walsh said. So instead, he leaned into the fact that he operates several stands throughout the city. He added a logo featuring his name and face to his stands, social media, and website.

“We weren’t sure how it would go, but people are just absolutely gaga over it. They feel like they know me,” he said. Branding his stands this way has also helped grow his returning customer base and recurring revenue. He said people will greet him at his stands and say they come every year. After moving away from the city, some people travel back just to buy from Walsh. It doesn’t hurt that Walsh, who already looks like Santa, dresses up a few times each season to greet shoppers at his stands. 

“I’m Santa about five days, six days out of the whole season. But it’s usually the busiest days. So it’s a little Santa miracle as far as I’m concerned,” Walsh said. 


IMG_4798 (1).jpeg

Greg Walsh dresses up as Santa Clause at his Christmas tree stands five or six times each season.

Walsh never sells trees himself while dressed as Santa, but that doesn’t stop him from monitoring how sales are doing across all of his stands using the Square Dashboard app. Plus, he uses the year-over-year data to see how his business is pacing compared to prior years.

He said he can usually tell how a season will pan out by December 1 or 2. The data from years prior gives him a realistic expectation of what’s to come and helps him set the right expectations with his team too. 

“I only completely ran out one time, and that was due to Covid,” Walsh said. He attributes this to decreased travel because of the COVID pandemic and people being stuck at home during that season.

This season, Greg said his sales were already off to a good start, a trend he likes to see. “And I think a lot of that’s been due to branding and Square,” he said. “People love it. They love it because they feel comfortable giving their cards to a sophisticated-looking system like Square, not sticking them in some weird little machines,” Walsh said.


Nina Godlewski
Nina Godlewski is an editor at Square covering all things technology and using storytelling to help businesses succeed and grow.


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