Portland small businesses band together to compete on Black Friday, Small Business Saturday and beyond

A growing buy-local movement helped buoy many small businesses in Portland during the depths of the COVID-19 pandemic.

Now, worried that consumers might be more cautious with their spending this holiday season, small business owners across the region are banding together in hopes of convincing Oregonians to skip the big boxes and forsake larger retailers’ Black Friday hype.

Organizers of longstanding efforts say they’re seeing heightened participation this year.

Canoe, a gifts and home goods shop in downtown Portland, is one of the businesses participating for the first time in the Shop Small Win Big campaign, which enters shoppers at small businesses into raffles for roundtrip flights, Trail Blazers tickets and hotel stays. It’s the latest incarnation of the shop-local campaign known as Little Boxes.

Craig Olsen, Canoe’s owner, said he didn’t join in previous years due to lack of staffing during a busy time of the year. Besides, he said, the store had been going strong since 2005.

But this year, in a tough business climate and with customer spending uncertain, Olsen decided the time was right.

“We felt like this was a really good year to show some unity with other small businesses,” Olsen said. “It just felt like this was the year to kind of join up.”

Though Canoe is based downtown, Olsen said he appreciated that the program was citywide, not focused on one area.

Shop Small Win Big began last Thursday and runs through Dec. 10. Shoppers can participate through an app and check in at participating small businesses via a QR code. Each check-in can help shoppers earn tickets for raffles – winners will be drawn and notified by Dec. 18.

“The campaign helps pollinate this idea of going to other small businesses and continuing to discover other places,” said Sarah Shaoul, founder of Bricks Need Mortar, a small business advocacy group and lead organizer of the event. “And it really takes the entire community coming together to make it happen.”

The campaign is designed to get Portlanders out exploring neighborhoods, Shaoul said. Partners include Travel Portland and the Downtown Retail Council.

Shaoul said small businesses “are the places that inspire us and make Portland the wonderful, unique place it is.” She said a post-holiday survey of the Win Big event last year found that most shoppers discovered businesses they hadn’t previously known.

About 125 independent retailers and pop-up shops will participate this year, Shaoul said, up from 105 businesses last year.

Portland’s city government is also hosting events to help promote local businesses. Prosper Portland, the city’s economic development arm, will hold the winter edition of My People’s Market, a marketplace featuring locally owned vendors, Dec. 2 and 3 at the Oregon Convention Center.

Amanda Park, program manager at Prosper Portland who helped develop My People’s Market, said the event has seen the number of applications grow, and competition is fierce.

“Typically, our market would fill up in maybe one to two weeks. But now it’s filling up in a couple of hours,” Park said. “So we’ve really seen the demand from small businesses to participate ramp up.”

The city will also open an outdoor ice skating rink and holiday market downtown, across Tom McCall Waterfront Park, starting Dec. 16.

Meanwhile, some small businesses are organizing their own pop-ups.

Jenna Emerson, who makes and sells resin-based art for her business Baby Plonk, is running a Small Business Saturday pop-up market at Mood, a shared space among small retailers at 3808 N. Williams Ave. in North Portland. (The small business answer to Black Friday is this Saturday.)

Emerson opened Mood in October as a temporary storefront to host not only her budding business but others as well. Other regular vendors include Alchemy, Always Here Books and PDX Fresh Start. But Emerson wanted to give more local small businesses a chance to have a storefront experience for the holidays, so she invited a dozen vendors to fill her space during the Thanksgiving weekend.

“Our whole thing is that you don’t need to have a lot of experience,” Emerson said. “If you just have an idea you want to try out or if you have art and want to just put in front of people, you can run with our market. We’re very welcoming.”

Emerson, who also helps coordinate the monthly pop-up Welcome Market at the Lloyd Center, said she didn’t charge vendor fees for the Saturday holiday market to make it more accessible for small business owners.

“I want small businesses to feel very empowered to just get out there and hustle,” she said. “We all know malls are changing, the retail atmosphere is changing, and we want to make it meaningful and keep shopping local.”

Michelle Sachiko Paul, who founded Fever Vision Dreams last year to sell cat-themed art, stickers and candles, is one of 12 vendors participating at Emerson’s Saturday pop-up market.

For Paul, intimate pop-up markets like these are a way for even smaller businesses like her to set up a physical presence during the holiday shopping season, she said. Paul sells artwork inspired by her three adopted cats, Suzy Bubba, Kirby and Leopold Von Paul.

“The bigger markets often have higher vendor fees, and not everyone can make it to pay to participate,” Paul said. “I feel like these grassroots markets from artists for artists make it more accessible to share our work and gives us a chance to be more visible.”

–Kristine de Leon; [email protected]