Fundraising: three syllables that spark fear, dread, or just plain confusion. Inspiring people to invest in your mission is a big task in the creative sector. But it doesn’t have to be a source of anxiety. It can even be—dare we say—a little bit fun.
These five Midwest arts organizations have turned fundraising for the arts . . . into an art.
Grilled Cheese Grant: Starting Small and Staying Accessible
In 2016, a group of seniors at Milwaukee Institute of Art and Design (MIAD) in Milwaukee, Wisconsin, cooked up a plan to help future students fund their senior thesis projects. Inspired by a “Sunday Soup” fundraiser in Chicago, they added Wisconsin flair and created the first Grilled Cheese Grant, supporting young artists by selling grilled cheese sandwiches.
Eleven years later, The Grilled Cheese Grant has grown from funding just one artist to five. Applications are open to all emerging visual artists (not just students) in southeastern Wisconsin. Finalists showcase their work at a fun local venue, and for a $15 ticket, attendees—grilled cheese in hand—vote to determine who gets the top prize (40% of funds raised, including donations).
The event now includes activities like butter-making, postcard-writing, and drawing stations hosted by fellow creatives.
Founding member Rachel Hausmann-Schall points to two key features in Grilled Cheese Grant’s success: community roots and accessibility.
“You can show up to an event and have five, 10, 15 bucks in your pocket,” Hausmann-Schall says. “And if you’re willing to put that money towards helping an artist execute a project that they have been hoping to do . . . that really means a lot.”
Grilled Cheese Grant’s advice to others?
“Be prepared to ask for a lot more than you think you need, and be prepared to be told no. Grilled Cheese Grant . . . was built on personal connections and trust within the community. Being prepared to just ask or build those relationships is absolutely integral to what we do. And sometimes, that comes with a no. But if you’re willing to keep trying and keep that dedication, you can build something pretty amazing.”
Lucky Number: Amping Up the Energy While Giving Back to the Community
Fun-loving and ever-creative, Ipso Gallery has turned art fundraising for the Sioux Falls, South Dakota community into a sport. (Kind of.)
Nicknamed “The Thunderdome of Arts Fundraisers,” Ipso’s biannual Lucky Number event supports local arts organizations or public art projects by auctioning local artists’ work, lottery-style.
Sponsors (individuals or groups) buy in for $1,500, which guarantees they’ll be walking home with three original art works–they’re just not sure which ones until their number is called.
Participating artists are guaranteed a competitive rate of $900 for three pieces of work: $750 from sponsors buying in, and $150 from Ipso.
The arts organization or project receives the other half of the funds raised from sponsors, which usually amounts to between $10,000 and $15,000. In 2025, Lucky Number funded a site-specific public art installation in Sioux Falls.
In short, everybody wins. And the energy is electric.
Liz Heeren, Director of Ipso Gallery, says the affordability, plus the high quality of the art they’re able to auction from local artists, makes the event successful every year with many recurring sponsors.
“This might only happen in the Midwest where you can do this. $1,500, and you go home with three original artworks,” Heeren says. “The artist wins, the sponsor wins, the organization wins.”
Ipso Gallery’s advice to others?
“People love the energy and the fever of the event, so play that up. We’ve had local celebrities calling numbers before. Amplifying the fun has been a big factor. [Also:] Start earlier than you think you need to!”
Monster Drawing Rally: Showcasing Artists and Welcoming First-Timers
Midway Contemporary Art in Minneapolis, Minnesota, is an artist-led nonprofit dedicated to uplifting visual arts in the Twin Cities. Their fundraiser of choice, inspired by a San Francisco initiative of the same name, is the Monster Drawing Rally.
Far from being scary, this family-friendly tradition has become a gateway for artists to gain an audience and for art lovers to collect something one-of-a-kind.
Dozens of local artists come to draw and donate their on-the-spot creations to the cause. The fundraiser attracts a crowd of families, fellow artists, first-time art collectors, and long-term supporters excited to collect an original work of art.
Every drawing is then sold for $35 on a first-come, first-served basis. If multiple people want the same drawing, a volunteer has them draw cards—high card wins. All proceeds support Midway’s exhibitions, public programs, artist grants, and research library.
“The event has introduced many people to collecting art for the first time, and because of that, the atmosphere feels welcoming, energetic, and genuinely community-oriented,” says Deputy Director Megan McCready. “We love the DIY nature of the event. Starting the day with bare tables, empty walls, and a cooler of cold beverages—and ending it having watched hundreds of drawings made and taken home—never fails to amaze us.”
Midway’s advice to others?
“Simply give it a try. The first iteration will likely feel like a whirlwind, although you figure out what works by doing it, adapting along the way. [Also]: We had to institute a no-glitter policy after discovering it’s impossible to clean off the concrete floor.”
The Supply Hive: Strengthening Community Ties Through Fun and Games (and Spelling Bees)
Only an organization called “Supply Hive” could give a spelling bee so much buzz—for a great cause.
This Des Moines, Iowa-based mutual aid nonprofit connects people with the supplies they need, especially through food rescue (saving food from being thrown out and distributing it to people who need it). To raise funds and forge community connections, Supply Hive hosted a spelling bee for adults!
Each round revolved around a theme, like “classic bee” or “naughty or nice.” Attendees who took the stage to spell got free admission and the chance to win a cash prize. Along with tickets, raffle sales, and day-of donations, the bee gave Supply Hive the chance to connect with new people, even attract new recurring donors.
“We try to keep our finger on the pulse of what people want, what’s creative and out-of-the-box,” says co-founder Zakariyah Hill.
Big galas aren’t Supply Hive’s style, and while raising money is important, the bee was laying the foundation for something deeper: a bigger hive.
“Our goal on that night was to attract people to our mission, to our organization, and have a fun night. To remind people what we do, and why they want to be included with us,” he says. “It takes a hive to see change done.”
Supply Hive’s advice to others?
“Don’t do it by yourself. Have a team and delegate roles for people to do. You don’t have to reinvent any wheels. And don’t put too much pressure on it. Take that improv mindset of ‘yes, and,’ then everything will flow better.”
zAmya House Parties: Fundraising and Friendraising at Home
Since 2004, zAmya Theater Project in Minneapolis, Minnesota, has used the tools of theatre to talk about housing and homelessness. They host workshops for people coming out of homelessness and employ artists who have experienced homelessness to create original plays for community performances.
With housing and home as the backbone of their work, zAmya developed a creative way to spread awareness and raise funds: house parties.
Hosted by supporters at their homes for invited groups of friends, the house parties featured a 75-minute program of live performances by zAmya company members and prompted discussions.
Along with introducing the organization, the host custom-designed the rest of the party as a barbecue, a brunch, or anything in between.
The result was a deeply personal introduction to zAmya’s work and the people making it happen. While the fundraising portion fluctuated as they workshopped the best way to “make the ask,” the friendraising component was powerful every time.
“When you’re in someone’s home, there’s a belonging that happens there,” says Maren Ward, zAmya’s artistic director. “With fundraising and the kind of work we do, it can be tricky [to not] feel like you’re exploiting people’s stories to raise money. And this didn’t feel like it was doing that; it felt like it was honoring people.”
zAmya’s advice to others?
“Really look at the fundraising piece and figure out who it makes sense to ask to do that. We started sharing an example of somebody’s script who had done a really good job at it. There’s so many different ways you could do it. But pay attention to that part.”
Tip Jar
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Galas and fancy dinners don’t work for every organization and that’s okay!
What other kinds of gatherings sound fun and feasible for your organization? Buck tradition to earn a buck!
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Don’t underestimate the power of small donations!
Getting more people to buy in—even in smaller amounts—leads to a lot of community-building and satisfaction.
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Showcase what—and who—your organization values.
Pulling back the curtain on the arts work you support can be a fantastic way to generate long-term interest and investment from new community members.
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Prioritize community participation.
Get people tangibly involved in fun ways like voting, bidding, spelling, or hosting.