Small Business Survivors: Tren’ness Woods-Black on keeping Sylvia’s Restaurant going and working on Thrillist Block Party in Harlem

Hospitality courses through Tren’ness Woods-Black’s veins.

The businesswoman and entrepreneur first got her start with her grandmother  Sylvia Woods, founder of the iconic Sylvia’s Restaurant. At the young age of 13, Woods-Black had her sights set on becoming a waitress, but was surprised that her grandmother had other plans.

“I grew up helping out clearing tables, passing ac customer something. [My grandmother] had us come in and dressed ready with black reeboks, black jeans, with Sylvia’s t-shirts on, training my cousin and I to be bus girls,” recalled Woods-Black. “My grandma promoted my cousin to become a waitress. I was like, ‘Where’s my section?’ And my grandma said, ‘I’m going to put you on the door as a hostess.’ My heart dropped.”

Though she was initially disappointed at her placement as hostess, her grandmother saw something in her that Woods-Black hadn’t seen yet, and she would later fall in love with the role.

“She said, ‘Baby, you are going on the door because you have great communication skills. You have got to be able to talk to the guests. Trust me, if you go to the door with the same happiness and excitement that you brought to bussing, you’re going to get tips,’” said Woods-Black. “She was right! She explained the importance of hosting — you are the first person that people are going to see, so you represent the whole restaurant. I started hosting at 13 and I loved it. I loved keeping people relaxed and learning where people were from. I loved hearing stories from Harlemites who had been coming since they were kids and watching as years went by seeing those people get older and have families and bring their kids.”

Woods-Black would continue to host at Sylvia’s over the years, but it was during her time in college and interning at RCA Records that she learned that what she was doing this whole time as a hostess was public relations. Woods-Black took her experiences and started up Sylvia’s PR and marketing department while also helping to expand the catering department, where she really learned to love putting on events.

During this time, Woods-Black also freelanced in PR before starting her own business, Tren’ness Woods-Black LLC (TWB), where she is able to bring special experiences to her hometown of Harlem. She has worked closely with people such as Bruno Mars and Janet Jackson to bring events and experiences to the neighborhood. Woods-Black has also recently partnered with Delanie West to launch a new product line, founded the nonprofit Harlem Park to Park, became the Executive Producer of her show Cornbread & Conversations and taken on roles in the NYC Hospitality Alliance and NYC & Company.

I represent small businesses, Black founders, entrepreneurs and creators across two different companies and 8 different boards. For me, it’s all hands on deck. Every ounce of talent, it’s a labor of love and if I have it, I’m giving it,” said Woods-Black. “My grandmother never let us forget that we are in the restaurant business, which means to be of service to our guests and our community. I had the same philosophy when forming my company.”

Tren’ness Woods-Black, granddaughter of the late Sylvia Woods and a third generation heir of one of Harlem’s most iconic businesses, Sylvia’s Restaurant, poses for a portrait outside its premises following the outbreak of the coronavirus disease (COVID-19) in Manhattan in New York City, New York, U.S., July 7, 2020.REUTERS/Mike Segar

Shifting to philanthropy

During the pandemic, Woods-Black found herself contributing to the Harlem community in a huge way. Under the Cuomo administration, she was tapped to represent small businesses on the New York Forward board.

“My philanthropic work became a 40-50 hour work week. I was making sure I was well informed and up to date on legislation and executive orders while making sure I was liasoning between businesses and the community with administrators to align in a meaningful way,” said Woods-Black. 

Woods put her skills to use to also create a food pantry on Sundays in Harlem, with the help of the CARE organization, Rev. Al Sharpton and his daughters.

“For the first time, we were not in a position financially to feed the masses. [Sharpton] explained to me that the pantries were closed on Sundays, so I thought I’ll come out on Sundays, in partnership with organizations, to feed over 1,300 people, and we’d do so within an hour,” said Woods-Black. “As soon as we were able to see light at end of the tunnel, my family started donating meals. We came up with the campaign ‘Sylvia’s Feed a Family.’ We would buy gift cards and we’d donate them in gift bags, gave out PPE, hand sanitizer, information on COVID, all necessary tools we had access to that could help in that moment.”

While giving back to Harlem, Woods-Black was continuing to build up her business, particularly on the philanthropic side. Her work got the attention of executives at Thrillist who were interested in helping her expand Sylvia’s even further.

“He explained that he grew up coming to the restaurant and Thrillist wanted to support restaurants and give them ghost kitchens. With their help, we built out a robust campaign and kitchen customized to our needs. They collaborated on Sylvia’s meal kit and gave us access to delivering in Lower Manhattan, which helped reintroduce us in an area where we had no presence before,” said Woods-Black. “They were impressed by my commitment to the community and to my skillset as an event producer. I had an idea for a block party that is ultimately a community party with a purpose; all the makings of a fun day but also created a new revenue source for our restaurants that are struggling.”

A party in Harlem

That idea sparked the Thrillist Block Party that was held in Harlem on Sept. 12. The all-day event featured several activities for people of all ages, including live performances, talks, booths from local restaurants and shops, and more.

Around 3,000 New Yorkers rolled through the block party, which helped give the local Harlem businesses a boost in these uncertain times.

“We provided what they needed, and we also highlighted their stories on the Thrillist platform. We sat down with microgrant recipients and talked about what they mean to Harlem and provide content to get them more connected to their audience during a difficult time,” said Woods-Black. “The block party Turned out to be everything I wanted and more, it was my actual living love letter for Harlem.”

As we head further into 2021, Woods-Black says that there are plans to bring the Thrillist Block Party to more cities across the U.S. while she continues to build up her brand.

I am sounding the alarm. My contribution to assist in this moment is by creating a platform regardless of where we’re at. You still have a platform to stand on with you. Reach out and help someone else. you always have space to do that,” said Woods-Black. “I just feel really blessed to do all of these things on behalf of Harlem and New York City, Black people and people celebrating community all over the globe.”

You can follow Woods-Black on Instagram at @queenofhospitality and on Twitter @TrennessTweets. For more information on Sylvia’s, visit