Humble beginnings: Whidbey Coffee owner is building success beyond Whidbey’s shores

Hilary Carpenter

Just before the lunch-time rush, a customer pulls up to the drive-through window at Freeland’s Whidbey Coffee wearing a T-shirt with a vintage company logo.

On the other side of the window, Megan Williams is having trouble containing her excitement.

“Those are very rare,” she said.

Williams beams with pride about Whidbey Coffee. She manages both the Clinton and Freeland stores and has been connected with the company since 1993, four years after the enterprise was founded.

From inside Freeland’s store, Williams is aware that she’s standing on hallowed ground ­— the birthplace of sorts for Whidbey Coffee.

Freeland’s drive-through was the first retail outlet opened by company president Dan Ollis and his former business partner Shawn Ogle in 1991 and is only a short distance from the site of the coffee cart they set up in front of Payless Foods a year earlier.

Officially, the company’s history is traced to the Evergreen State Fair in Monroe, where the young entrepreneurs sold chicken fajitas out of a borrowed concession trailer in 1989. But it was in Freeland where the mobile operation first became grounded, and yet, nearly tipped over.

“Oh my gosh, the health department at the time … They required an umbrella over the cart,” Ollis said recently, recalling the summer he and Ogle set up shop in front of Payless without one. “I got the umbrella but it was a Sam Adams umbrella. Some people thought I was selling beer.

“I remember people thinking we were crazy selling coffee. I remember sales for the first few days, thinking, ‘Oh my gosh, we made a mistake.’ ”

Whidbey Coffee has grown immeasurably since its humble beginnings with Ollis alone at the helm since 1993.

The company is now represented by 13 retail outlets in the North Puget Sound area and, through a partnership with Red Lion Hotels, is being served in a rapidly growing number of hotel lobbies across the country.

Despite its expansion, Whidbey Coffee and its founder continue to be popular and appreciated on the island that inspired the company name.

Whidbey Coffee was voted Business of the Year and Ollis the Business Person of the Year in the Best of Whidbey Readers Choice Awards conducted annually by the Whidbey News Group.


The journey has been a steady ascent for Ollis, a 1988 South Whidbey High School graduate who grew up in Bayview. A pivotal move came in 2007 when he acquired Seattle-based coffee company Victrola Coffee, which gave him two coffee brands, a roastery and café on Pike Street and two other cafes in the Emerald City.

The move also increased Ollis’ expertise in the coffee industry and ended Whidbey Coffee’s reliance on using contracted roasters.

“I have watched a three-location company turn into my goodness,” said Stacy Madsen, a buyer for Whidbey Coffee who’s been with the company since 1992 and now works in the head office in Mukilteo.

“We bought another company, Victrola. Now we’re roasting our own coffee. Our wholesale program is taking off. We’re throughout the country. Some international.”

“It has changed dramatically. Who would have ever thought?”

Tom Brown, store director at Payless, counted himself as one of the doubters in the early days.

He once employed Ollis as a grocery clerk, then watched him transition to a barista in front of his store at a time when specialty coffee was still a novelty.

“We made fun of him, saying, ‘Who is going to pay this much money for espresso? Who’s going to buy it from a cart?’ ” Brown said.

Brown’s history with Ollis dates back to the days when he was a middle school bus driver.

“He kicked me off the bus,” Ollis said.

“I’ve known Danny for a long time,” Brown said. “He was sort of a hellion as a grocery clerk. But he’s always had a vision that he was going to be somebody and not in a bad way. He was always looking to do something.”

He did.

Ollis estimates he and Ogle sold about 20 cups of coffee a day that summer in front of Payless.

Today, he guesses that total company-wide, including three Victrola cafes, is about 5,400 cups per day.

“What I really like about Danny is he’s really successful but he always remembers his roots,” Brown said.

“A lot of people do very well and seem to forget where they came from, but Danny doesn’t. He always remembers where he’s from. He always tries to help the community. He’s very loyal to us and to South Whidbey.”

Whidbey Coffee is known island-wide for its generosity. It is a major sponsor behind the fireworks shows in Freeland and Oak Harbor that celebrate the Fourth of July.

The company also awards a $5,000 scholarship each year to a South Whidbey High School senior who is headed to a community college. Ollis attended Edmonds Community College.

“His vision was obviously to run an amazing company,” Madsen said. “Today, we’re not only able to run an amazing company, we’re also able to give back to our communities. That’s very important to all of us here.”

Brown said Ollis still visits him faithfully once a month at the Freeland store and calls even more frequently.

It’s a bond that’s important to Ollis, who laughs about memories of shenanigans that got him into trouble with his former boss. He remembers the apology he needed to make to be considered for the clerk job after the bus incident. He doesn’t mind that Brown still refers to him as “Danny.”

“I think long-term relationships are important,” Ollis said.

“It is who we are. It is our makeup. Coffee is great. We have a great time selling it every day. But I’m in the people business.”