Mompreneurs: Shay Wood Talks Iconic Harlem Fashion & Legacy

Shay Wood is the matriarch of Harlem’s “first family of fashion,” overseeing a growing business ecosystem under the Harlem Haberdashery umbrella. From fine spirits and beverages to a boutique, podcast, and legendary clothing atelier—everything Wood builds revolves around one constant: building a legacy for her family. In this episode of Mompreneurs, Wood joined host Nancy Redd to reflect on fashion, family, and the lessons of first-generation entrepreneurship.

“The 90s was perfect for the creation of our business.”

5001 Flavors was Wood’s entry into entrepreneurship. Today, it’s recognized as a Harlem fashion institution that has outfitted legends across music, film, and sports—from Biggie and Beyoncé to Jay-Z, Alicia Keys, Swizz Beatz, and LeBron James. The list goes on.

She teamed up with her then-boyfriend, now husband, Guy Wood. He brought the creative vision and sharp sense of style, while she brought the strategic business mind. The young couple was on the path to something special.

“At an event, someone needed a look for their artist. They stepped to (Guy), ‘Are you a stylist?’ And he was like, ‘I am now.’ So in 1992, as a junior at Columbia University in my dorm room, 5001 Flavors was born.”

“Ultimately, one client turned into 10 turned into 100.”

Mompreneurs: Shay Wood — Source: Shay Wood

Word of mouth fueled 5001 Flavors’ reach across the music industry’s rising stars. “It was a good time. Social media did not exist, but referral-based marketing was really what made 5001 work,” said Wood.

Hip-hop was on the rise, and 5001 Flavors rose with it, growing alongside the movement as it became a global force. From music to fashion, hip-hop touched every part of the culture—and 5001 was there, helping shape a new era of style with their iconic custom clothing pieces.

“The good thing is that music then started to translate into all of these really cool opportunities—movies, national tours, because some of these artists became music moguls, and then they had other people that they produced, and then they were in movies. So now you could dress them across all of the lanes. We followed our clients as they diversified their revenue streams.”

This year marks the company’s 33rd anniversary, a legacy still deeply tied to Harlem and its creative heritage.

“You can’t rely on one revenue stream, so you have to think about what’s next.”

Wood knew that diversification was key. Thirteen years ago, she and her family opened the Harlem Haberdashery clothing boutique at 245 Lenox Avenue. Today, the family-run business includes not only the couple, but Wood’s brother and son. “It was important to further extend the entrepreneurship to other members of my family,” said Wood.

“The good thing about working with my family and having my husband as my business partner, there is a lot of interconnection between my personal time and my business time, and I love it. It doesn’t bother me. I can easily switch between mom, business, wife, sister, friend, working with my family. So I actually love it, it works well for me.”

Harlem Haberdashery has expanded beyond clothing into accessories and eyewear, including a collab with Vontelle Eyewear, founded by fellow mompreneurs Nancey Harris and Tracy Green.

With HH Bespoke Spirits, the Woods introduced Harlem Haberdashery gin, rum, and vodka—later adding bottled alkaline water to their line. “It was a lifestyle category for us that made sense,” she said, aligning the collection with the family’s design-forward aesthetic.

“Generational curses ran in my family until they ran into me.”

For Wood, entrepreneurship is about more than fashion. It’s about rewriting family history. “In our communities, we are so talented. We make something out of nothing all the time. So I love when we’re able to monetize our talents.”

She’s passionate about building wealth that her daughter and “bonus kids” can inherit, so the next generation doesn’t have to start from zero. “It’s hard for that first-generation entrepreneur to come in without a business plan, the knowledge, or the blueprint,” she said. “The challenge is being a history maker in your family and breaking these generational curses.”

Also in this episode of Mompreneurs, Shay Wood opens up about blending love and business, breaking generational curses, and giving back. Watch the full conversation above.

Catch new episodes of Mompreneurs every week.

Welcome to Season 4 of Mompreneurs—where we spotlight brilliant Black women who are building their businesses and raising their families with strength and style. Join host and New York Times bestselling author Nancy Redd as these inspiring mompreneurs share their stories and the lessons they’ve learned along the way. Catch new episodes of Mompreneurs every Monday on MadameNoire’s YouTube channel or listen to the podcast online on the Urban One Podcast Network.

Categories: Entrepreneurship