How one man left the tech industry to live out his cookie monster dreams

Michael Pinckney opened Pinckney Cookie Cafe in 2009 after leaving the technology industry.

When looking back on his childhood, Michael Pinckney recalls finding his love of baking in his mother’s kitchen. Pinckney was one of four children who followed strict rules about not bringing junk food into the house, or he would face getting grounded.

“On the other hand, we could have whatever we wanted as long as we helped,” said Pinckney. “In my house growing up, there were always–and I mean always–fresh baked cookies or cakes.”

By the end of 2009, Pinckney started the Pinckney Cookie Cafe, an online cookie business that shortly made its way to retail stores, and thereafter, local farmers markets.

“It came about very organically because I am a cookie monster,” said Pinckney. “I started developing a chocolate chip cookie recipe in my New York City apartment in the 1980s just for fun.”

Over the years, Pinckney developed two cookie recipes that snackers raved about and craved, but while on a quest to create the perfect chocolate chip cookie, Pinckney was working in the technology industry.

He spent years at IBM in sales management, he said, and briefly worked as a private consultant before making his way to Seattle, where he worked at Microsoft and local start-ups.

“Quite frankly, I actually had some health concerns–sleep disorders–one of which wasn’t readily diagnosed while I was at Microsoft, and I just decided that it was time to do something totally different,” said Pinckney.

Pinckney mentioned how Microsoft treated him wonderfully, however he developed carpal tunnel syndrome while on medical leave, and when he went back to the office, he noticed that his ability to work was impacted. Since people had been raving about his cookies for years, Pinckney decided to open the Pinckney Cookie Cafe.

How the cookies crumble

“We really focus on our cookies having a balance between the different elements, and really having them be soft and chewy, and a great mouth feel,” said Pinckney.

The first ingredient listed in the cookies is dark Belgian chocolate, or callebaut chocolate, where in most cookies the first listed ingredient is sugar or flour, said Pinckney. The business’s flagship cookie is a brown butter, brown sugar, bourbon spice cookie, made in part from Woodinville Whiskey Co. bourbon.

Pinckney’s favorite artisan cookie is the Bing Bling!, which is made of chocolate dough, dark Belgian chocolate chips, coconut, and dried Bing cherries. Pinckney Cookie Cafe also offers gluten-free and vegan cookies, or ‘Miracle Cookies.’

The Bing Bling! cookie. Courtesy of Pinckney Cookie Cafe.

The Bing Bling! cookie. Courtesy of Pinckney Cookie Cafe.

“The secret to the miracle cookies is we spent months experimenting, and I use 10 different ingredients to substitute for the flour,” said Pinckney, who explained how the Miracle Cookies have been a great addition to the company.

Pinckney’s goal is to create the best cookies possible, which is why he prides his company on sourcing local ingredients; he gets his eggs from Cypress Farms in Yelm, WA to ensure consistency with freshness. Furthermore, Pinckney sources his salt from San Juan Island Sea Salt, a local company that collects and evaporates water from the San Juan Islands through the sun, rather than burning energy, said Pinckney.

Cookie sales support COVID-19 relief and racial justice

During the COVID-19 pandemic, Pinckney felt his mental health being impacted, and needed to find a way to give back. For every order of a dozen cookies or more that was sold, Pinckney donated $5 to charities engaging in COVID-19 relief.

“Over the course of 2020, we raised over $15,000 for charities doing COVID-19 relief,” said Pinckney. “That was the year that George Floyd was murdered, and halfway through we changed the focus to racial justice.”

Pinckney scaled back, and eventually stopped donations during the first quarter of 2021 because it was not sustainable in the long-term, he said.

“The original motivation was not a sort of business strategy or anything like that,” said Pinckney. “It was just an emotional need to do something positive at a really bad time, and just feel better about getting up everyday in the morning.”

While not a business strategy, Pinckney said having donated to charities shows what’s important to him. As a small business that’s rapidly growing, Pinckney is always looking for ways to give back. Most recently, his company is at a point where he can think about offering full benefits to employees, which was previously unattainable for him.

Where to find Pinckney’s cookies

In 2021, Pinckney Cookie Cafe returned to farmer’s markets after a quick hiatus due to COVID-19. On Thursdays, the cookies can be located at Queen Anne’s seasonal farmers market. On Saturdays, Pinckney Cookie Cafe can be found at the University District farmers market, and on Sundays, they can be found at the Ballard farmers market and the West Seattle farmers market.

Currently, there are no plans to increase farmers markets locations at this point, but the company is looking towards major plans for the future.

“We do have plans to build a bricks and mortar location. We’re not far enough along in that process to be able to announce it or give a date, but it is a firm plan at this point,” said Pinckney. “The first location will be in Kirkland, and then we plan to open additional locations after that.”

When asked his favorite part about running a cookie business, Pinckney laughed and stated how it was an embarrassing question.

“My favorite part about running my cookie business is of course, eating raw cookie dough,” said Pinckney, who brought up how his second favorite part was eating a Bing Bling! cookie nearly daily.

Joking aside, Pinckney acknowledged how running a business is a varied experience that constantly brings new challenges.

“I like the intellectual stimulation of having different things that I need to figure out,” said Pickney. “It’s interesting. It’s a lot of variety, and then competing for that would be the interaction with customers.”

To learn more about Pinckney Cookie Cafe visit