T-Shirt Streetwear Brand

How Doobie Duke Sims Built a Thriving T-Shirt Streetwear Brand from Scratch

Doobie Duke Sims once lived on $3 meals—two slices of pizza and a Coke—while touring with his band, Shinobi Ninja. Nights were spent in vans, chasing a dream.

That phase of his life felt fulfilling, but today, his reality looks much different. Now, he runs Snow Milk, a T-shirt streetwear brand launched from a Brooklyn basement in 2020.

A Humble Start with One T-Shirt Sale

The brand’s first year brought little success. Sims made just $50 from a single T-shirt sale in 2020. However, by December 2022, sales had skyrocketed, reaching $96,000 in revenue that month alone, according to CNBC-reviewed documents.

Over the next five months, Snow Milk generated over $260,000 in apparel sales. Although December remains the highest-earning month, the steady growth shows promise.

From Touring Musician to Streetwear Entrepreneur

Sims’ shift from music to streetwear fashion came from necessity. After his daughter was born in 2018, he needed a more stable income that kept him closer to home.

While browsing Craigslist, he found an ad for a fully equipped print shop in a dance studio basement. Already skilled in Photoshop, he saw an opportunity.

At first, he used the space to design band T-shirts. Teaching himself screen-printing, he soon realized he had everything needed to launch a clothing brand.

The Birth of Snow Milk: A Dream Turned Reality

The brand’s name came from a literal dream. Sims saw snow bursting from a milk carton, a vision that stuck.

Starting small, he sourced blank clothing from thrift stores, screen-printing his unique designs onto them. However, launching a T-shirt streetwear brand during the pandemic proved challenging. Sales barely moved—just one T-shirt sold on eBay that entire year.

Street Fairs, Word-of-Mouth, and Scaling Up

Determined to get his brand noticed, Sims took Snow Milk to street fairs in Washington Square Park in 2021. The face-to-face exposure created valuable word-of-mouth marketing, leading to $15,000 in sales that year.

With those earnings, he launched an online store and hired a team. Today, his 11-person staff makes a combined $10,000 per week, significantly expanding production and reach.

Creativity vs. Business: A Learning Curve

Designing clothing comes naturally. “I can be inspired by anything,” Sims says. “Clothing, for me, is just another medium of producing rhythm.”

Running a business, however, presented a challenge. Instead of focusing solely on design, he spent hours watching YouTube tutorials on business management.

Currently, he works on cutting costs while maintaining quality, ensuring long-term profitability. Most earnings go back into the business, and in 2023, he paid himself only $12,530. To cover personal expenses, he continues taking music-producing gigs.

From Music to Mastering Profit Margins

“Coming from music, I didn’t know anything about profit margins or costs of goods,” Sims admits. “I know bridges, verses, and choruses. But I had to learn about spreadsheets, QuickBooks, payroll, and insurance.”

The Future of Snow Milk

With momentum building, Sims envisions expanding Snow Milk into a household name in the streetwear industry. His journey proves that creativity and persistence—paired with a willingness to learn business fundamentals—can turn a passion project into a profitable streetwear brand.