‘I’ve already lived my worst days on earth’
Shawano coffeehouse changes hands with former employee becoming owner
February 23, 2026
ASHWAUBENON – Co-owner Stacey Stewart said Fly Me Flag, 2190 S. Ashland Ave., has seen a sharp rise in business in the two months since acquiring Best Custom Flags in Downers Grove, Illinois.
Stewart said the acquisition is expected to double the company’s custom flag and banner volume, with increased interest and sales already evident.
“The return on investment… it’s going to pay off,” she said. “From [former Best Custom Flags owner, Laurie Olsen’s] customers’ perspective, it’s been really flawless.”
As she and her husband, Robert, mark their 10th year as owners, Stewart said Fly Me Flag is entering its 41st year serving the Greater Green Bay community, with momentum and excitement building for what’s ahead.
A bit of history
Stewart said Fly Me Flag was founded in 1985 by Joyce Halron after she struggled to find a flag to fly on her boat.
She said the business was later sold to Mike and Carol Debbout, before being acquired by her parents – Terry and George Rapp – in 2011.
“I have so much respect for all of the owners, what they achieved and all those milestones,” she said. “My dad bought the business with the intent of owning it for five years.”
Stewart said the opportunity to purchase the business from her parents came at the perfect time, as she and Robert were at a crossroads in their careers and ready to pursue a new direction.
“They didn’t want it to get sucked up into a sign company or a big corporate entity,” she said.
Stewart said she and Robert – both Wisconsin natives, growing up in Fond du Lac and West Allis, respectively – met in Las Vegas while both held leadership roles at the same hospital, her in community outreach and him in environmental and food services.
After marrying in November 2014, Stewart said they visited Fly Me Flag during its busy season, and by May 2016, they decided to buy it.
She said they moved to Green Bay that November and assumed ownership in February 2017.
“I’m so glad we took the risk,” she said. “It’s really been such a blessing in so many ways.”
Since purchasing the business from her parents, Stewart said she and Robert have doubled revenue.
Upon arriving in Green Bay, Stewart said she initially lacked a clear understanding of the community.
Becoming a member of the Greater Green Bay Chamber, however, she said, allowed her to connect with fellow small business owners and serve some of the region’s largest companies.
Stewart said she and Robert each bring their own strengths to the business and have specific roles – with her as CFA (“chief flag authority”) and Robert as CFI (“chief flagpole influencer”).
Expanded reach
As the business’s fourth owners, Stewart said they are committed to only selling American flags that are “Certified Made in the USA,” meaning they are 100% manufactured by American workers, with domestic-sourced materials from U.S. facilities.
Before the acquisition, Stewart said flagpole installation made up about 50% of the business, with American flag sales accounting for 25-30%.
“[With flagpole installation], we cover the whole state of Wisconsin and the Upper Peninsula of Michigan,” she said. “We’ve had occasions where we have done Iowa, Minnesota and Illinois where we are competitive.”
Fly Me Flag, Stewart said, is a certified retailer of the Flag Manufacturers Association of America (FMAA) and a member of the National Independent Flag Dealers Association (NIFDA), which applies to: U.S. flags, international, military, specialty and civil service.
It was through that involvement in industry-focused professional associations – including her role as immediate past president of NIFDA – that Stewart said they became friends with Olsen.
“We purchase from the same manufacturers…,” she said. “We have the same philosophy about customer service. Robert and I kind of saw the opportunity. We started playing with the [acquisition] idea more than a year ago.”
Stewart said those brief conversations escalated over time, culminating with Olsen eventually indicating she wanted to wrap things up by the end of 2025.
“I think the acquisition is going to have a huge impact on our business,” she said. “We’re really proud to expand our customer base and continue to serve Laurie’s customers in the way they have been used to being served.”
With a strong national presence, Stewart said Best Custom Flags will transition to the Fly Me Flag name and is now stocking flags from multiple states.
“I feel so good,” she said. “A friend got to retire. We’re working out the logistics stuff, and in the end, those customers are going to continue to receive the same customer service… and the care they have come to expect.”
Three-prongs
Describing Fly Me Flag is a “three-prong business,” Stewart said it encompasses its in-store retail experience, online sales and flagpole installation and service.
“We strive to be the business that is incredibly easy to do business with,” she said.
Fly Me Flag’s five core values – competence (be consistently capable and efficient), strong will (persist in the face of adversity), optimism (choose to see the opportunity), meticulousness (perform with care and precision) and servant leadership (take the extra step to deliver and delight) – she said, are central to every aspect of the business.
Stewart said customer feedback helps confirm that Fly Me Flag’s values are visible in its work, with repeat business remaining a cornerstone – such as a municipality’s recent order of 300 springtime flags.
Furthermore, Robert said Fly Me Flag handled the installation of the American flags and flagpoles at Lambeau Field, featured atop the 4K Mitsubishi Diamond Vision video boards added in 2023.
“It’s probably the most visible project we’ve done,” he said.
Stewart said in-store consultations cover installations up to 35 feet.
Taller flags, she said, require full-site coordination, including soil testing, and may even involve discussions with the Federal Aviation Administration.
“Flags are usually under sign ordinances,” she said.
Due to the specialized nature of the work, Stewart said she advises against hiring a sign company or landscaper for flagpole installations.
“That’s what sets us apart,” she said. “That’s all we’ve done for 40 years. I think there is a lot of trust that has been earned and comes with that expertise.”
Robert said the Fly Me Flag team takes pride in residential and corporate flagpole installations – such as the 120-foot flagpole recently installed at AmeriLux’s newest facility.
Though Fly Me Flag previously relied on Creative Signs in De Pere for bucket and boom truck services, Robert said in 2025, they opted to acquire their own equipment, which now gives them the ability to expedite repair work.
“It’s been great,” he said. “Customers are really shocked [with our turnaround time]. We always underpromise and overdeliver.”
For flagpoles 50 feet and above, Robert said Fly Me Flag uses hydro excavation.
Stewart said hydro excavation offers customers a cleaner installation while helping the business avoid workers’ compensation claims.
National attention
Having participated in NIFDA convention panels on flagpole knowledge and innovations, Robert said Fly Me Flag is increasingly relied upon by companies across the U.S. for installation guidance.
When attending the NIFDA convention for the first time in October 2017, Stewart said they were reluctant to share details about how they were innovating their business.
“[Before] that first convention, I [remember saying], ‘We don’t want to share what we’re doing…’ and now we’re being asked to serve on these panels…,” she said. “[Other attendees] were willing to share what was working – it really felt like family… What a difference nine years [has] made.”
Stewart said she spent six years on the NIFDA board and continues to serve in an advisory capacity as immediate past president.
“It’s huge for our business,” she said. “It’s really helped us to get to know the industry.”
By serving alongside leaders in the industry, Stewart said she has gained insight into effective business growth strategies.
E-commerce, she said, has transformed the industry, but some online retailers make misleading claims about whether their American flags are truly made in the United States.
“The [NIFDA] board is working with the FTC (Federal Trade Commission) on labeling laws,” she said
Stewart said a flag can only be considered made in the USA if every component is domestically sourced and sewn in U.S. factories using American labor.
She said the NIFDA is supporting legislation that would mandate federally funded flags be manufactured in the United States.
Fly Me Flag’s dedication to USA-made flags and supporting veterans, Stewart said, led to a partnership with HOOAH Wisconsin, whose mission focuses on veteran wellness and suicide prevention.
To date, she said Fly Me Flag has installed flagpoles for 27 area veterans and supplied them with USA-made flags.
Stewart said they have also committed to providing lifetime maintenance for the HOOAH veteran flagpoles, including replacing the American flags as needed.
America250 celebration
Stewart said this year’s 250th anniversary of the Declaration of Independence is a significant event for Fly Me Flag – with the store offering six commemorative flags and custom flags and banner options for municipalities, businesses and individuals.
“I just quoted a job for 38,000 stick flags [for an out-of-state veterans group],” she said.
Stewart said demand for the commemorative America250 flags is already exceeding industry expectations.
“We are encouraging everyone to get those large flag orders in early, to get their commemorative 250 flags,” she said. “If they want to have something custom-made…, those orders [also need to come] in early. I honestly don’t even think it’s on people’s radars yet. A lot of people don’t even know it’s the 250th yet. But once we get into the patriotic season…, we expect demand to grow considerably.”
The future
Similar to other small businesses, Stewart said one of Fly Me Flag’s biggest challenges is artificial intelligence (AI), which has affected her website.
The AI-generated summaries at the top of online searches, she said, can reduce website traffic, making it difficult for small businesses to compete.
“As a small business, it’s hard to compete with those changes,” she said. “It’s constant… You really have to stay on top of it.”
Stewart said she is collaborating with a marketing agency on search engine optimization (SEO) to develop a strategy that redirects AI-driven traffic back to Fly Me Flag’s website.
In addition to her and Robert, Stewart said Fly Me Flag has one full-time and one part-time store employee, as well as a full-time flagpole installer.
However, with the expected growth from the acquisition and the America250 celebration, Stewart said Fly Me Flag plans to add staff, including a full-time store employee, a full-time installer and a seasonal installer.
Beyond staffing, she said Fly Me Flag is focusing on growth in custom flags and banners, installation services and the retail store.
At the store, Stewart said customers can experience the fabrics firsthand and get guidance on flagpole installations.
The three stars in the Fly Me Flag logo, she said, represent pride, patriotism and personality, which reflect the company’s focus on supporting customers throughout their entire purchasing journey.
“The difference really is the personal experience,” she said. “I think that this is where we see the opportunity to grow our business and where we are intentionally focusing our efforts.”
