American Dream Achieved
IBA, as a fifty-one-year old business brokerage firm serving the entrepreneurial community of the Pacific Northwest, has been uniquely positioned since before the American Bicentennial celebration of 1976 to witness and hear the stories of thousands of people who have lived the American dream through entrepreneurship creating beloved businesses by employees, customers, and communities while finding personal fulfillment and financial prosperity through execution of their ideas, hard work, perseverance, and ability. In an effort to share these stories heard throughout the years by our team of business brokers, who are commonly regarded as the “best listeners” in the M&A industry, IBA has retained highly regarded writer, Nesha Ruther, to tell their stories. It is our goal to share one story a month. It is our hope that you will find the stories as inspirational and motivational as they are to us and the buyers who bought the businesses in IBA facilitated transactions in Washington, Oregon, and Alaska.
The Story of Jay Shephard of Dueber’s of Cannon Beach
By Nesha Ruther
Jay Shepard began his career as a marine engineer, working for seven years aboard ships. “While I was out on the ships, I worked on honing my computer programming skills, and after a period of time, I was able to transition from being a marine engineer to my own high-tech computer program-ming business,” he says.
The computer programming business had rapid success, and before long, was taking in venture capi-tal. “We moved into the pre-IPO stage in the late ‘90s, and we almost made it out of the window into an IPO until the dot-com bomb in 2001,” Jay recalls. “We ran out of funding in that window.”
When the dot-com bubble burst, Jay, like so many others, was forced to pivot. “My son was five years old at the time,” he recalls. “So, I needed an immediate cash flow when the markets turned south due to the dot-com bust. I had invested in a gift shop business with the intent of being a silent partner, but then my other partners decided they didn’t want to be on the hook for the half-a-million loan needed to build it.”
Jay had to decide whether he was going to take the leap into the gift shop business or look for another job. “A close friend of mine was also a partner, and I decided it looked like a great opportunity, so we leapt in headfirst,” Jay says. “We had two ex-partners who stayed on to train us, and we learned from the ground up..”
While Jay’s foray into the world of souvenirs and gift shops was one of convenience rather than pas-sion, he was able to apply many of the skills he’d acquired running his computer programming busi-ness. “The way we ran the shop was technology-oriented,” he says. “It was managing spreadsheets and ordering through computers.”
While there are multiple ways to run a gift shop, they tend to fall into two camps. The first is more like a boutique: a smaller number of items with larger variety. The second is, in Jay’s words “stack it high and watch it fly.”
Jay’s stores fell decidedly into the second camp. Whereas a boutique might hand-select original, arti-san-made items reflecting the owners’ specific tastes and artistic sensibilities, Jay’s brand of gift shops focused on bulk purchases from the same general pool of products. “The gift and souvenir business relies on making sure you’ve got the right products, tracking what’s selling, and replacing what isn’t,” he says. “Whatever is selling, you bring in more of it.”
And while the branding and designs of the products are specific to the area in which they are being sold, the products themselves are not. “The standard was t-shirts and sweatshirts with localized im-prints, and then your magnets, keychains, ornaments, and jewelry. We kept the price point low. Back in the day, it was below $30, now it’s below $60.”
Jay was able to open two different shops, one in the Mount St Helen’s Hoffstadt Bluffs Visitor Center and another in the Weyerhaeuser Forest Learning Center. The former performed so well that the county visitor center decided to try to take over the shop themselves, and Jay lost his lease in that tran-sition, forcing him to look elsewhere.
In 2010, Jay settled on a gift shop in Canon Beach. Not only was the location beautiful, but it was a high-profile tourist location, which allowed Jay to apply everything he learned at Mount St Helen’s. “The shop’s original name was Dueber’s in Cannon Beach,” Jay says. “It had been started by Mary Dueber in 1961 and originally had been a general store selling jeans and hardware before they began selling gifts and souvenirs. Mary’s son, Peter Dueber, worked there from the time he was 12 and sold me the business when he was in his mid-60s.”
The store’s long history meant it had an established legacy in Cannon Beach, but that didn’t mean Jay was going to rest on the laurels of its previous owners. He doubled its historical profits almost imme-diately after purchasing, and the business continued to grow with each passing year.
What many tourists don’t realize is that the top 20 to 50 vendors for gift shops and souvenirs operate nationwide, providing items to stores all across the country. “I could take that concept anywhere in the country, particularly in coastal areas. With some small tweaks, I could predict what I was going to sell no matter where we went. When we go to the Florida Keys or San Francisco, we see the same vendor lines,” he says.
Because the gift shop formula was so reliable, it didn’t take long for Jay to open another store. In 2018, Jay opened another giftshop in Seaside, which, like Cannon Beach, went on to experience an-nual growth.
While the gift shop model has always been largely transferable from location to location, innovations in technology have only made them more so. “The really exciting trend for the last three years has been print-on-demand,” Jay says. “You can order your T-shirts, sweatshirts, baseball caps, magnets, or keychains in small quantities at affordable prices and have it shipped to you within one to two weeks.” This was a game changer, because, historically, shop owners would have to rely on the ven-dors for their designs, order in large quantities, and wait months for the products to arrive.
Another innovation that has had a big impact on the industry is the use of AI. “I started combining AI with print-on-demand three years ago, and it’s taken off,” Jay says. “I was able to use AI to make our own localized creative design and artwork, order the products in small quantities, and test the different designs on different colored apparel garments to see what worked.”
Over the past few years, Jay has created roughly 60 unique winning designs for the apparel, magnets, mugs, and ornaments in his Oregon Coast shops. Many have performed so well, that he’s become the best-selling vendor in his own stores. “We were able to come up with designs that nobody else had up and down the coast, so while the AI designs didn’t supplant all our other vendors, we’ve become our own largest vendor,” he says. “We knew that with the combination of creating our own digital art with the ability to have it printed and shipped in low qualities, we had a real opportunity that had nev-er before been available in the gift industry.”
These innovations, combined with AI’s power to manage accounting and reordering products, have left the industry more automated than ever before. “I won’t say AI has revolutionized the gift and souvenir business, but it’s close to getting there and it will within the next couple years,” Jay predicts.
“It’s a great time to be a gift shop owner because with the print-on-demand technology combined with easy access to art, the shops themselves are much less dependent on large vendors,” Jay says. “In the future, shops could transition into doing their own art and printing on-demand in-house. That is going to lower the cost and also increase the variety of products moving forward.”
Jay predicts that this development will not only provide customers with more diverse products but give a struggling retail industry a much-needed boon: “The gift shops definitely need it because you’re seeing a transition from retail gift to retail service. The stores and boutiques that were selling T-shirts and cover-ups and shoes are now selling services like wellness clinics and beauty services, dog grooming and yoga,” he says.
Still, there remains one area of the industry that technology has not yet found a way to replicate and improve: customer service. “The merchandising is only part of the business,” Jay says. “The big chal-lenge is staffing. You have to train and maintain a staff that shows up and is pleasant and gets along with other staff.”
Finding hardworking and reliable staff members can prove even more challenging in seasonal indus-tries. Jay quickly learned that it saved a lot of time and energy to keep their staff through the winter months, so they don’t have to hire and train new employees come spring. “It’s not economical, we don’t need them in the winter, but even if they’re working reduced hours, it’s nice to have proven team members so we don’t worry about having to replace them the next spring,” he says.
Tourist communities also typically only have a small number of year-round residents, and large num-bers of Airbnbs and VRBOs have made housing scarce. The result are communities with too many jobs and not enough employees. “There’s a small number of people that live on the coast and there’s no housing for anyone to come and stay here,” Jay says. “So, the bar for hiring is really, really low. We increased wages enough to draw some good staff, but it’s always a challenge.”
While Jay handled much of the merchandising and logistics from his home office, it was his wife, Linda, who took care of hiring, staffing, and managing the stores. “I’d take care of the ordering, so I’d do the spreadsheets on a three-week basis and order and re-order whatever was needed. I’d also take care of all the accounting and bills, and Linda did anything HR related,” Jay says. “Over the past 16 years, she’s hired and trained over 130 people to work in the shops.”
Jay also credits Linda for the arrangement and aesthetic sensibilities of the stores. “I did the layout and the planograms of what went where in each area, and then she refocused each of those and beautified the merchandising,” he says. “I 100% credit my wife for creating shops that were visually and aes-thetically pleasing. I can bring in the product, but I needed her to arrange it so that the stores were fun to explore and looking at them was a happy experience that covered a wide variety of shoppers.”
Linda’s involvement also allowed the shops to cater to a demographic that Jay, on his own, might not have been able to account for. “She knew that even though some of our spa-type items might not have been the most profitable or the fastest-moving, they provided a variety that we needed,” he says. “An upscale female shopper probably isn’t going to be looking for a magnet, keychain, or hoodie, but if we had a nice selection of bath bombs, lip balms, and lotions, she could find something that she could take home. That was a part of our focus too, providing a wide variety of items so that the whole fami-ly could find something for everyone.”
For many, working with their spouse would prove challenging at best, but it was never an issue for Jay and Linda. “We have an incredible relationship and there was never an unenjoyable moment other than the one time she ran down the street after someone who had stolen something from one of the stores,” he laughs.
“A large gentleman had stolen some jewelry, and she ran out the door after him and told him she wanted her jewelry back otherwise she would call the cops. He emptied his pockets,” Jay recalls. “That was the only time I ever had a cross word for her because I don’t want to put any staff at risk and I certainly don’t want my wife at risk trying to save $20 worth of jewelry.”
Aside from chasing down shoplifters, Jay and Linda were in total harmony as both business partners and spouses. “The best part of running the stores was being able to work together,” Jay says. “We would go to all the shows together and had a great time meeting with vendors and picking out appar-el, and then we would spend late nights arranging everything. Creating the shops and getting to share that with her was the best part of the business by far. And I give her a tremendous amount of credit for making them as successful as they are.”
In addition to getting to travel with his wife, industry shows in Las Vegas and Florida allowed Jay to get creative when it came to the merchandising of the stores. “I enjoyed finding new concepts and envisioning the shoppers seeing them and purchasing them. I love that people take their kids into our shops and get joy out of looking at our merchandise,” he says.
Using AI—or JAI, as Jay calls his software—to create custom designs has also revealed a fun, crea-tive component to his job. “My next-door neighbor is a very talented artist, and I told him that I’m a talented artist too, I just can’t get it on the paper. He called that a leaky elbow, that your art comes out of our elbow and it can’t get on the canvas, that’s always been my problem,” Jay laughs.
“But with AI, I’m able to describe a vision I have, and it can create it. I was able to create a beautiful watercolor of an elk in front of Haystack Rock with a moon in the background. We put that on t-shirts and hoodies, and it was a real ‘wow’ moment. That design ended up being a home run, people would walk past the store and see it in the window and come in to buy it.”
Another special moment Jay recalls involved a design he created of a pirate. A few months later, he was walking down the beach and spotted an older gentleman dancing with his grandkids. He was wearing Jay’s pirate t-shirt. “I stopped and I shook his hand and told him I’d made the artwork on his shirt, and he thanked me and said he really enjoyed wearing it. Creating your own designs and seeing it bring joy to different people is really great.”
And while Jay’s designs have more than pulled their weight, when it comes to bestselling products, nothing can compete with absurd magic of a kids’ toy. “We brought in a silly little item called a Sugar Squeezy. It’s this little gelatin fidget toy that you squeeze. They do ridiculous numbers, we sell a hun-dred of those things a day, it’s crazy,” Jay laughs.
Under Jay’s ownership, both gift shops grew annually in profits, with the exception of 2020. While most industries struggled during the Covid-19 Pandemic, few were hit harder than tourism. “It was very challenging and surprising that we even survived it,” Jay says candidly. “It was hard to get staff-ing, and we had to reconfigure the shops so we had more spacing so people could be six feet apart, so people could come in one door and out another.”
The shops barely scraped by, but when the restrictions finally lifted, people were eager to travel and even more eager to commemorate their travels with souvenirs. “The good thing was that with the funding the government provided, when we did open back up, people were coming in with wads of fresh, crisp, $100 bills in their pockets, they were buying like crazy,” Jay says. “We had a real boom in business for a few years following [the Pandemic]”
Jay had always had the long-term goal of retiring when he turned 70. “I really enjoyed running the gift shops and the creativity and cash flow that came with it,” he says. “But I didn’t want to do that forever, I have a lot of other projects I’m working on, and I wanted to spend time with my wife and do some travelling. Whether it was the gift shop or anything else, I knew I didn’t want to be doing the same thing after 70.”
Jay had originally met Gregory Kovsky back in 2009, when he was looking at a Seattle gift shop to buy, and the pair had kept in touch over the years. “Last fall, I got a hold of Greg and told him that I was ready to put the gift shops on the market,” he says.
Gregory introduced Jay and Linda to Cameron Johnson, an IBA broker out of Portland. Cameron and Jay ended up having a remarkable amount of common history. “Cameron had actually worked with and flown some helicopters with a gentleman up at Mount St. Helens that I had sold helicopter tourist flights for,” Jay says.
The similarities didn’t end there. Jay’s son graduated from the University of Oregon business school, where Cameron’s son is now attending. If that alone wasn’t enough, Jay owns 100 acres in White Salmon, Washington. At the time of their meeting, Cameron had just made an offer on 20 acres of property right next door to Jay’s. “Cameron had decided the developer was too slow getting the roads up there done, so he backed out of the purchase, but he’s been up to my property a number of times now and wants to purchase 20 acres, so we’ll become neighbors in the future,” Jay says.
Jay had decided a long time ago that when he was ready to sell the businesses, he was going to sell through IBA. “Over the years, I’ve looked to buy additional gift shops, so I’ve basically looked at every gift shop listed for sale over the last 15 years. With all the businesses that were large enough to be profitable, Greg and IBA have been a part of the sale,” he says. “It was a no-brainer. When it came time to sell, I knew to get a hold of Greg. But it was also very fortunate to find out that Cameron was part of the team, because we hit it off right off the bat.”
“[Cameron] was impressively thorough in analyzing the business and the cashflow, reconciling the profit and loss Quickbooks cash flow versus the profit and loss on the income tax to make sure they all matched and matched my pro forma projections. Seeing his valuation process, I was very im-pressed,” Jay says. “And the fact that he knew that it was bankable, which to me, is the most im-portant thing. I’ve seen so many business owners that just don’t think about who is going to bank the deal, who is going to finance the purchase, and that’s the most important part of the sale. That was what Cameron was excellent at. After proving the finances, he had bankers lined up that would bank the deal, so all he needed to do once he’d done all that legwork was find an interested party.”
The sale went through on June 1st, 2026, allowing Jay to meet his goal of retiring by his 70th birthday, five months early.
For Jay, the American Dream means two things. “Pre-sale, it means doing something you enjoy that generates enough capital that you can support yourself and your family, while being able to take time off and enjoy hobbies and the like,” he says. “But when you’re done with that, the next step is being able to retire with enough funds that you can travel, pursue your hobbies, and support your family without having to wonder where the next dollar’s coming from.”
For Jay, those dreams have become the reality. “I absolutely feel I’ve been enjoying the American Dream and will continue to do so with this sale,” he says. The next great challenge is deciding what he wants to do with all his newfound free time. “I always have a million ideas on what I want to work on and how I want to make money, so it’s a new challenge to decide what to do when you don’t real-ly need the money,” he says with a laugh.
For Jay, the future is wide open. After a career of selling people souvenirs from some of their favorite trips, he can finally be the one to travel, explore, and maybe get a little something by which to re-member his adventures.
Nesha Ruther
Nesha Ruther is a writer and editor from Takoma Park, Maryland. She received her BA in English Creative Writing from the University of Wisconsin Madison, where she received a full tuition scholarship through the First Wave program based on academic and creative merits. She was a 2016 Young Arts winner in spoken word, a 2016 winner of the DC Commission of the Arts Larry Neal Writing Award, a 2017 winner of the Mochila Review Writing Award, which was judged by Nikki Giovanni, a 2020 winner of the University of Wisconsin’s Eudora Welty Fiction Thesis Award, and a 2022 Tin House Winter Workshop Participant. She has been commissioned to write and perform for the National Education Association, and has had work published in NarrativeNortheast, Angles Literary Magazine, Beltway Quarterly and more. She recently completed a tenure as the Lead Writer at Bond & Grace, and a co-host for the podcast Lit Talk (https://www.bondandgrace.com/the-lit-talk-podcast). Currently, Ms. Ruther is teaching classes and working on her Master’s Degree at the University of Kentucky.