Meet the Cashman sisters, female auctioneers who are raising millions for ND and Montana charities

BISMARCK — When sister auctioneers Missy O’Malley and Katie Fitzsimmons take the stage, it’s like watching a veteran comedy duo in action.

Fitzsimmons, the older sister, is the more reserved of the two, although she also reveals a clever wit, a flair for one-liners and a photographic memory for every item auctioned.

O’Malley, 18 months younger than Fitzsimmons, is bubbly and electric. She often works as the “spotter” half of the twosome — clapping, stomping, slapping her thigh and even jumping to amp up the excitement while also helping her sister identify bidders.

“That's our job. We are the joy injectors. We’re the fun providers. We’re providing the stoke, if you will,” O’Malley said.

Since 2016, Fitzsimmons and O’Malley have been known as the Cashman Auctionisters. They specialize in running auctions for charities, selling everything from high-end art to a McDonald's lunch with a parish priest to raise money for Make-a-Wish chapters, humane societies, women’s entrepreneurship programs and schools.

In the last eight years, they’ve raised over $10 million at nearly 200 events in North Dakota and Montana.

Sometimes they work separately, as Fitzsimmons lives in Bismarck and O’Malley lives nearly 600 miles away in Bozeman, Mont. But when they work together, the magic is undeniable.

It's high-pressure work that requires a whip-fast wit, sharp instincts, the ability to read the room like a skilled diplomat and the potential to spout up to 250 words per minute — something the Bismarck-born Cashman sisters have been preparing for it all their lives.

If you lived in central or western North Dakota in the last 40 years, you probably saw TV commercials featuring the Cashmans.

Down-to-earth patriarch Dan Cashman ran (and still runs) Bismarck's Cashman Nursery, which he cleverly promoted with TV ads featuring his six telegenic kids. From an early age, the Cashman kids urged viewers to call the nursery at “701-222-tree-tree-tree-tree” or gamely sported earmuffs that sprouted branches to tell viewers, “We’ve got trees growing out of our ears.”

Even today, strangers who recognize them will walk up to them and spout the catch phrases.

The sisters believe it was this early exposure to TV cameras — along with growing up in a big, boisterous family — which helped them feel comfortable in the spotlight.

“Coming from a big family, if you finally did get something to say, you had a quick platform and a quick minute, so it better be good,” O’Malley said.

The girls’ communication skills also were shaped by their mother, Carol, a communications professor who taught speech at Bismarck State College for 30 years. “So as a kid, we really paid attention to diction and enunciation,” she said.

Although O'Malley and Fitzsimmons are close in age, Carol Cashman said they have diverse personalities that complement each other on stage.

O'Malley takes after Dan’s father, who founded Cashman’s nursery and was a born salesman with bushels of charisma.

For her part, O’Malley calls herself “misbehaving O'Malley,” because she’s always been the fun, spontaneous sister who “will try something until you tell me no.”

Fitzsimmons is more like Carol’s father, who worked as a bank president by day but had a photographic memory which allowed him to entertain at conventions by reciting long ballads and intricate jokes.

Fitzsimmons also has her grandfather’s head for business. When they first started the Auctionisters, Fitzsimmons insisted they keep spreadsheets to record every detail and dollar earned from past events — a habit that has become invaluable for tracking their progress.

O’Malley describes her big sister as “the smarter, wittier, older sister who has a quicker tongue. She doesn’t miss a bit.”

“The two of them together are really good; they fill in the gaps for each other,” Carol said. “They take their talents and, as they say, they work for the greater good. I’m very proud of them.”

O’Malley was at a black-tie charity event in Bozeman in 2010 when she first witnessed the power of a top-tier female auctioneer.

At the time she was working as a local radio personality who taught snowboard lessons and deejayed events on the side. She'd also signed on as the charity event's deejay.

When auctioneer Johnna Lee Wells swept into the room, O’Malley saw a striking brunette dressed in a chic, olive-green cocktail dress and stilettos. The auctioneer took total command of the space, raising hundreds of thousands for the charity and then dashing off to catch her plane like a Hollywood star.

“Being from North Dakota, the only auctioneer that I had ever seen or heard of was Farmer Brown from the stockyard. So out comes this very classy woman,” O’Malley said. “She was so classy, so powerful, so commanding in the best way. And so I remember just being dumbfounded and struck by her presence.”

O’Malley volunteered at the event the following year, and again saw Wells. Afterward, she struck up a conversation with her. Then, unable to contain her excitement, she called Fitzsimmons — even though it was 1 a.m. CT.

Fitzsimmons happened to be awake, as she had a newborn daughter.

“Katie, I got it!” O'Malley practically hollered into the phone. “We are in the wrong line of work! We need to become auctioneers!”

Some siblings might have hung up on such a notion, especially at 1 a.m. But not Fitzsimmons. Like her sister, she still had some grease paint in her veins.

The sisters would get to know Wells, who mentored them and encouraged them to attend auctioneer school.

After all, they belong to a small sisterhood. Statistics vary on how many women in the U.S. are auctioneers, although a 2022 blog post by the National Auctioneers Association reports that 15% of its membership is female. Zippia, an online recruitment service, reports that 23.9% of the 5,582 auctioneers currently working in the country are women.

In June of 2016, the sisters attended the Missouri Auction School, which is billed as the “Harvard of auctioneering” on its website.

They spent 10 days attending classes in a Holiday Inn conference center in St. Louis. Their class contained 76 people from across the country; only seven of them were women. Most of the students were taking over family businesses and planned to auction cars or livestock.

When the sisters told classmates they wanted to dress up and raise money for charities, their classmates seemed amazed they could get paid for it.

Every morning, the 76 students warmed up by running through tongue twisters and number games, such as reciting digits by certain increments.

They also developed their auction chants — the ritual of alternately calling the number of the current bid with the number the auctioneer is seeking.

“You start selling fence posts as you’re driving down the highway,” Fitzsimmons said.

Before the week was done, the Auctionisters had landed their first gig.

That first year, they raised $59,000. In 2017, the number jumped to $428,000. In 2019, it exceeded $1 million. The sisters were doing so well that O’Malley left her morning show gig at Bozeman’s local CBS affiliate in December 2019, intending to do events and fundraisers full time.

“They had a record number of events set for 2020. “Then COVID hit and every event we had was canceled,” O'Malley said. “But now things have bounced back.”

While the sisters work hard to tailor their approach to each event, they set the mood with a light-hearted introduction which helps set the evening’s tone.

“We’ll say, ‘I’m Missy, and I’m Katie, and we’re the Cashman sisters, the auctioneer sisters. We like to talk fast, we like to have fun and we like to raise a boatload of money for good causes,’” O’Malley said.

Typically, one sister will be the lead auctioneer while the second will be the spotter, or “ring man.” They’ll riff off each other while building excitement over the organization and the night’s prizes.

The spotter's job is to let the auctioneer know there’s a bid out there. O'Malley isn't shy in how she does that. Her signature spotting move is the “whistle-cha,” an enthusiastic two-finger whistle punctuated by a cowboy-esque “Chaaa!”

“It’s like I’m herding cattle,” O’Malley said. “I’m slapping my thigh, I’m stomping my foot. People actually think I’m on something or five cups of coffee.”

“The auctioneer can’t see everything, so the spotter is crucial,” Fitzsimmons said. “Missy is so dang good at spotting. Truly, she has a way of being heard and spurring excitement while not overpowering me when I’m selling.”

It must work. Amanda Godfread, regional director of Make-A-Wish North Dakota in Bismarck, said they hired the Auctionisters in 2018 for their World of Wishes fundraiser. They were so pleased with the results that the Fargo chapter added the sisters to their their Wine and Wishes fundraiser a year later.

Godfread said their approach perfectly balances humor with the reality that Make-A-Wish kids face.

“They’re both so tactful and able to balance that (mixture) between professionalism and care and the whimsy and brightness of a wish,” Godfread said.

She said the sisters also provide pre-planning expertise. They’ll share their experiences of successful features from past auctions and volunteer ideas on the most strategic way to set up auction items.

Since the sisters have taken on the Bismarck region’s auctions, Godfread said fundraising numbers have increased 87%.

It takes a lot of preparation, time and travel to do this, and neither sister is getting rich from it. Auctioneers may charge 20 or even 50% of proceeds from an estate auction, but a charity auction is a different animal.

“They're selling things, and here we're just sort of raising money,” Fitzsimmons said. “So if a (fundraising) event is only bringing in $15,000 or $20,000, I can’t take 30% of that income.”

Today, they’ll charge around $5,000 for large gala events, Fitzsimmons said, although that number is smaller in the Bismarck area. “Missy’s always up on my case that I don’t charge enough here. But the market’s very different than in Bozeman.”

It’s enough to occasionally prompt Fitzsimmons’s husband, Owen, to say, “You know, we don’t have to do this. We’re doing OK financially.”

After all, Fitzsimmons already holds a 50-hour-a-week job as director of student affairs for the North Dakota University System.

To which Fitzsimmons reminds him auctioneering helps fill her need for performance.

“It gives me a lot of oxygen,” she said. “It gives me energy.”

It also takes energy.

“When you're on stage, it's a mix of stand-up comedy,” Fitzsimmons said. “And selling. And reading every nuance in the crowd in real time ... It's this balancing act, and you don't realize in the moment how truly exhausting it is.”

“It’s a roller coaster that's sort of an adrenaline rush that we both kind of seek at the same time,” Fitzsimmons said. “And it's a risk that I'm always going to be willing to take.”

O’Malley said the auctioneer business has proven more rewarding than she could have hoped.

“It’s very awkward to ask for money,” she said. “So we try to make it fun. We try to make everyone feel included. We just want to make sure everyone feels great about what they’re doing and why they’re there."

Learn more at http://www.theauctionisters.com