Beyond the Cookie Cart:

Finding Success on your Own Terms

Meet Nate of Nate’s Oatmeal Cookies. You may have seen his shop on Belmont street, or his cookies on display at your local coffee shop. Nate is an acquaintance of mine and I have two distinct memories of him. The first is seeing Nate push a cream colored cookie cart down a grassy slope at Alamo Square park in San Francisco. The other is five years later, when I walked into his brick and mortar store on Belmont street in Portland.

It’s thrilling to see someone go after their dreams. It’s even more exciting to walk into their dream and eat a delicious cookie. So I decided to sit down with Nate and fill in the 5 year gap. On a rare sunny day in late February, Nate and I sat outside of Stumptown coffee on Belmont street, only a few doors down from his shop. The story I heard is one of perseverance and wins, but also how success is perceived by those who have it. An unexpected kernel, I found much more relatable.

The idea of Nate’s Oatmeal Cookies began in the pandemic. He was craving his mother’s family-loved Oatmeal cookies and after receiving not just the recipe, but all the ingredients to make them, he began obsessively baking. Sounds familiar right? A lot of us were baking during the pandemic, but Nate had a deeper connection to this hobby. In his own words he was “kind of a mess.” He was bartending and picking up some less than savory habits, “my life wasn’t good, [it] wasn’t healthy.”

“So you’re saying the cookies saved your life,” I couldn’t help but interject, but Nate doesn’t laugh. He actually considers my statement, his face rather serious, and responds, “the cookies gave me some stability; they gave me a thing to fixate on and build.”

It was this stabilizing force and lots of encouragement from his Dad, that Nate decided to pursue his cookie venture more seriously. Where his Mom was the creative genius behind the cookie, his Dad was the businessman behind the baker. Throughout every stage of his journey, the voice of his Dad was always there. “He wants me to make millions,” Nate says.

So Nate kept pushing and getting into a farmers market was his next big challenge. It wasn’t easy. Nate was rejected from every Bay Area farmers market he applied to. He couldn’t break in and he was getting discouraged. But then one of those the-universe-conspires-to-help-you-succeed type things happened. Nate decided to move back to Portland. On his drive from CA to OR, a friend connected him with Yoti, a “big greek guy” who needed help running this farmers market stand in Beaverton. Before Nate even arrived in Portland, he’d found his in.

While working for Yoti, Nate learned how to treat customers well, how to up-sell, how to have confidence in your product, and how to merchandise the table. He also made in-roads with the markets’ management so when he applied for his own table, they already knew who he was, and luckily his vegan Oatmeal Cookies were a unique product for the market to offer.

Nate’s confidence grew and while he was making strides, his Dad was still on him to go bigger. This persists even today. Nate described to me how a typical conversation goes. His Dad – Have you heard about xyz company? They started with this, and now they do this, and now they have a hundred stores! Nate knows this all comes from a place of love and he’s grateful for the ways his Dad has pushed him. But his ambition is different, it’s not fueled by the thought of endless expansion.

Nate got his own farmers market stand in 2022, which he still operates today and in 2024 he opened up the store on Belmont. Nate’s biggest hurdle? The business side. He describes transferring his business license from CA to OR with the familiar ire of decoding a medical insurance bill. I don’t even remember this doctor's visit? I thought my co-pay was only $25? Why have I been on hold for an hour? We’ve all been there and Nate is the first to admit he’s not the most organized person. He’s a “creative ball of ideas,” so keeping the paperwork neat and orderly is not his strong suit. Let’s just say he’s paid a few late fees.

As Nate laments these difficulties, he mentions that he is a “micro business”. He says this to convey to me that Nate’s Oatmeal Cookies is still a small operation. Sure, he’d love to hire someone to manage the business side, but right now he has to do it all himself. I start to understand that there’s still a mountain to climb. I sense that what Nate actually struggles with is the feeling that he hasn’t done enough. And how could he not? In a society obsessed with growth and a father with a seemingly infinite number of cookie millionaire success stories, Nate can feel like all he’s accomplished isn’t that amazing.

In talking about his struggles, Nate reminds himself why he started this in the first place. He just wants to create something that wasn’t there before. He’s not in it for the glory, the rapid growth, the money making frenzy. He’s in it for the joy and the people. Take his chocolate for instance. Nate only buys fair-trade chocolate. Of course he could get the cheap stuff, but Nate cares about the person harvesting the cocoa beans, just like he cares about the people working at his store, and the people who come in for Oatmeal Cookies.

Nate's story lands on something so personal. We probably all have something worth celebrating, an achievement we never thought possible, but how long did we revel in that win before we set the next goal? Nate is still figuring it out, but for now, he’s learning how to respond to his Dad. He focuses on how he wants to show up in his community and make his business successful, without the pressure of growing too fast. Nate may sometimes still see himself in his pandemic kitchen or pushing his cookie cart through parks in San Francisco, but to everyone else, he’s Nate of Nate’s Oatmeal Cookies: a small business owner and the creator of some seriously good cookies.