Funny (Small) Business Stories

March 17, 2017 • 6 min read

Being the boss is serious work, but the always-stressful schedule of a business owner should include a regular round of laughs, to help you maintain your sanity and keep you loving the small business life. These business owners have mastered getting their daily dose of funny and staying sane.

The Marquee Messages

“We’re kind of known for our marquee,” says Art Design Portland (ADX) founder Kelley Roy.

ADX is a makerspace for artists, builders, and designers. The team takes safety seriously, but that’s about it. Anyone walking or driving by the building immediately encounters the ADX approach to life.

Reddish orange capital letters spell out smile-inducing phrases such as “Bro, do you even craft?” or “Pumpkin spice lathe.”

“The sense of humor has changed as new staff have come on board,” Roy says. “Right now, my staff has a similar sense of humor, so the marquee gets better and better. That’s one thing that I love about my team, and they definitely bring that into the space.”


For example, ADX sent Nick Offerman a gift that had to be opened with a table saw and has invited the Parks and Recreation star to teach a woodworking class.

“That’s a little dream of ours,” Roy says.

On the occasions that ADX uses its old-school social media platform for real messages — promoting gallery shows or events — they tune it with their spirit.

“Put your pants on, we’re having a party.”

All the levity works toward a higher purpose, Roy says, especially in a potentially intimidating environment of power tools and unfamiliar equipment.

“It helps people know we’re a really approachable space. People are friendly and willing to help. That marquee kind of says that without saying it directly. We know how to have fun and keep things safe but light. That’s our little humor gift to the world.”

The Disappearing Door

Every owner strives for a clean space to welcome customers, and that routine cleaning chore is no different for Kim Wattrick and her team at Summit to Soul.

Wiping windows is one of the daily tasks at the boutique fitness and apparel store in Washington, D.C. Wattrick’s shop occupies a building from the early 1900s, and during renovations, she decided to keep the glass door for its beauty and to save on costs.

She or her staff ensure the glass remains spotless. That’s the problem.

“When people leave the store, we repeatedly have people run into the door,” she says. “People are embarrassed. They tell us we do too good of a job cleaning the glass.”

The staff has held brainstorming sessions for ideas that would make the barrier more visible. Yet a chalkboard sign that hangs from the door hasn’t stopped the bumps and bruises.

“We have people run into the door almost daily,” Wattrick says. “We warn people when they’re on their way out.”

The Costume Confusion

Volunteers staff the counter and the aisles at the collective known as Boneshaker Books in Minneapolis. They even deliver literary purchases via bicycle. Being part of the crew means taking part in presentations about favorite topics to aid team bonding or voting to open the shop for 24 hours straight to celebrate Independent Bookstore Day.

For Halloween one year, a volunteer portrayed the ghost of a beloved author of children’s books.

“We advertised that Shel Silverstein was coming to read from his books,” says Amanda Luker, a collective member who helps make steering decisions for the overall business.

“He was so good. The only problem was that some people didn’t understand it was a ghost.”

A few people in the crowd asked the kinds of questions only answerable if Silverstein were alive and writing, a tough feat when the author had died in 1999.

“The volunteer was trying really hard to stay in character, but it got a little awkward.”

The Unplanned Partnership

Stitch & Rivet/Instagram

Manufacturing on a small scale puts the customer in contact not only with the products but also the process. Anyone wandering by Stitch & Rivet in Washington, D.C., can watch the design and assembly of bags and other leather goods.

Katie Stack’s shop sits on the way to a Metro station, and the front window entices people to stare or stop in. That simple interaction can lead to meaningful relationships or just casual comments. Sometimes both.

“We regularly get attorneys who stick their face in the door,” Stack says. “People see you doing a job that’s not what they do.”

She says the legal gurus often talk about how they wish they could pursue their passions. But one woman kept returning. On her walk to work. On her walk home. Twice a day for a month.

“She would stick her head in and say, ‘I want to do this for a living.’ Finally, I stopped her and asked what she did for a living.”

At the time, Stack needed help with a cease-and-desist order to thwart a scammer. She learned that the curious, would-be bag maker specialized in a particularly helpful area.

“She’s a business attorney,” Stack says with a laugh. “Now she’s my attorney.”

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