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Nikisha Founder of Win Win Coffee Bar Fills The Gap In The Black-Owned Coffee Industry

Updated: May 10, 2022

There's a reason we say a cup of coffee can change the world. Coffee is one of those things that brings people together, and when people come together, amazing things happen. We're not talking about that awkward networking event where people pass around their Instagram and LinkedIn accounts, hoping they don't have to talk to each other aside from the superficial conversations. We're talking about real connections forged by something as simple as sitting down over a cup of coffee. Sometimes these connections lead to lifelong friendships and new ideas.

Nikisha Bailey, the co-founder of WIN WIN Coffee Bar, said, "I've always just enjoyed coffee and bringing people together. So through the course of my life and career, I was always known as a person who could bring different types of people from different walks of life together and just have an amazing conversation." Not only does Win Win Coffee Bar offer a space for creatives to meet and collaborate, but they also shifted to eCommerce and launched Win Win Roast with a local minority-owned importer, roaster, and distributor, Bean2Bean. A portion of their sales goes to community job training.

As the former VP of APG / Atlantic Records, Nikisha hadn't owned a business before but felt it was time to own something for herself after a long career in corporate America. She and her co-founder Matthew Namaste acquired the coffee brand. It was already up and running when they became the new owners of WIM Win. When asked what it was like to acquire a business, Nikisha said, "We negotiated the price, and we took a look at the assets that he had to offer. We had to bring in an attorney and an accountant to look over all the financials to ensure there weren't any debts or liens on the company, and to make sure it was something that we could viably do ourselves, knowing that it would be a turnkey situation and preparing ourselves for whatever the community might have to say about that." Nikisha and Matthew expected to make their investment back within five years based on the numbers.

The original owners that we acquired the business from where White men, and the location of the coffee shop is in a historically black neighborhood that is currently gentrifying , so naturally, Nikisha had some concerns about how the community would embrace them in this particular area of Philadelphia. She continued to say, we were these young Black entrepreneurs coming into an area where you don’t see a lot of black ownership. We were shifting up the space and making it our own. There was definitely a little trial and error phase for us as we hosted different events like Black trivia and workshops on Anti-Recidivism in Philadelphia. It was so amazing though, that all of our efforts were well received by the people who supported WIN WIN prior, as well as our new patrons.

Just different, like we were hosting community workshops on Anti-Recidivism. There are just different things like that that affect the Black community, but that was also well received by the people who supported the prior Win Win, so that was awesome."

Before the pandemic, Win Win Coffee Bar did well and, within two years, made back their investment. But like most businesses, they were at a standstill during the pandemic. They couldn't sell anything, and that's when they pivoted to the eCommerce model, launching their online retail space by selling their own coffee brand.

Nikisha saw the financial opportunities of roasting their coffee and noticed the stark gap in Black-owned coffee roasters. She said, "I feel like everything happens for a reason. And each piece of learning along the way has led me to this point of running a full-blown commercial coffee, roaster, and distribution company."

Her top tips about acquiring a business are:

  • Have cash reserves.

  • Be okay with making mistakes because that's where the learning happens.

  • Be ready to finance on your own if you need to.

  • Make sure you're bankable, find investments from people looking to invest in a startup, or have the means to float yourself for six months.

What's the biggest risk you've taken?

Nikisha's biggest risk was moving to Philadelphia to start a business. She's lived in New York for so long that it was a risk going outside of her bubble to live and work in a different state. Going outside of her comfort zone was a big theme for her during this process. She said, "I continue to be an advocate for the lack of Black representation and business owners in Philadelphia. It's one of the most prominent Black cities, but there are only like 2% of Black business owners in the city. And just always speaking out about that and noting that gentrification is a real thing.

Like all these amazing businesses are opening up in these Black neighborhoods, but none of them are Black-owned. And I think that's a serious issue." She's on the Merchants Association board to remain up to date on what's happening with business owners in Philadelphia.

Tell us about a major setback and how you recovered.

The most significant setback for Nikisha and her partner was becoming bankable. A bank denied their business loan because they didn't have any history or the paperwork. She also didn't know of any outside funding aside from the banks that they could apply for. Ultimately, they figured it out.

The next setback was the pandemic. They had zero income coming in until they decided to sell their own coffee. Within a few months, they sold 4,000 bags—so they knew they were on to something. The business is self-funded, and they've completed the Goldman Sachs program to learn how to operate a business.

​​What fears did you have along the journey?

Nikisha's biggest fear was starting a business in the food and beverage industry, an unfamiliar territory to her. She had to rely on other, more knowledgeable people to help her.

What are you most proud of when it comes to Win Win Coffee Bar?

Nikisha is proud of not giving up. She knows how to execute a goal and find solutions. Therefore she took the same drive into her business. Even though the road was intense and lacked clarity, Nikisha never gave up. She said, "Just waking up every day and knowing that I want it to keep this going and believing in myself that I could actually figure it out."

Describe what it was like preparing for the pitch competition.

As a music executive, Nikisha never shied away from speaking in front of large audiences and pitching ideas and artists, but she had to become more comfortable with pitching herself. She said, "And I think especially as a Black woman, you don't always toot your own horn or go in and talk about the positive things you're doing and what makes you so unique and different from other people.

So I really enjoyed this pitch competition because I was surrounded by other Black women and minority women. And we were all just talking about the best things that we have been doing and what we have to offer. So it was very great to experience that. And then to have someone review my deck and tear it apart, but then offer real suggestions. Like people don't always take the time or the energy to go in and tell you what you really need to be doing. So that was super invaluable for me."

We asked Nikisha what the crowdfunding experience was like because pitching in the competition is only the beginning. She said, "Everyone I worked with within the music industry, every network I had, I sent an e-blast. I probably could have been a bit better coordinated and thought about it beforehand, but I didn't, so lesson learned."

Nikisha used her social media platform to get the word out, and people started to share the competition. She said, "I was genuinely taken back by how supportive everyone was, and a lot of people still don't know that I'm in the coffee industry. And so I think this one is a great introduction, but it was just great to see my network and my community show up for me." Entering the pitch competition exposed Win Win Coffee Bar to many opportunities.

Her advice for those looking to pitch is, "I would say, get your story ready. Many people buy into who you are as an entrepreneur and as a business owner, so make sure your values and mission are clearly verbalized, and then be open to feedback. Participate in the sessions where you review the decks, and you can get feedback from the BGV members. Like that's invaluable and incorporate it as much as you can. Know that they're very experienced and don't take anything personally."

Win Win Coffee Bar will use the pitch funds to scale their commercial roasting and purchase a packaging machine that helps to seal the bags of coffee. They used a hand sealer in the past, which would take hours and lots of family involvement. With this new automation system, they'll be able to get more coffee bags out of the door and increase their sales volume.

Support isn't always given to Black and Brown women in business; when has this shown and hurt or disappointed you the most?

Nikisha said, "​​It shows up a lot of times, especially if I'm negotiating with the lawyer or a landlord or any partner that we have a contract with.

I have ten years of negotiating in the music industry, and I think people aren't quite ready for what I actually know or the things that I could easily pull and figure out myself. So, I find it sometimes challenging just getting people to actually hear me and know that I'm an expert in what I'm talking about—but then realized that part of business, if things aren't moving from you, don't move from them.

So knowing that you don't scare easily or you don't back down, and things don't always move as quickly as you want them to. It's worth getting what you want out of certain deals and relationships with people, especially your landlord, or if you're renting because that's always been the most difficult for us."

What's the most critical lesson that you've learned about business?

Nikisha has learned that you don't have to know everything as an entrepreneur. If entrepreneurs are willing to listen to different perspectives, then make a judgment on your own or be willing to take the risk without outside insights.

She said, "You might not know a clear answer, but I feel like it's this, and if it's not this, go back and learn another lesson. I think a lot of times, as Black women, we always want to be right. We always feel like we have to be the experts, or else people will judge us. But that's not how real life works. Like a lot of executives, they don't know everything. They have big teams behind them that support them and guide them to the right answers."

She later says to ensure you have a core group of people within your circle where you trust their perspectives so you can use them as a sounding board.

What do you think is an important skill or asset you need to succeed in business?

Nikisha recognizes that she's a great networker and quickly connects with people. She believes that's an essential skill to have as an entrepreneur. If there's a skill you lack, she encourages entrepreneurs to collaborate with individuals who can fill those gaps. She said, "What characteristics do you have to lead your business and really emphasize and focus on bringing those to the surface every time you work in your zone of genius."

What's the most exciting part of your business?

Nikisha loves working the barista shifts and making coffee for people. She also loves to problem solve. For instance, when the espresso machine broke, she had to learn how to troubleshoot that.

What do you think the future holds for Black and Brown women entrepreneurs?

Nikisha said, "I think the future is bright. I think this, especially with the pandemic, it's interesting how the world works. Cause I believe the pandemic showed a lot of women, Black women in corporate America, that they weren't really happy.

But they also had the wherewithal to lead and do things themselves. So I'm even seeing a lot of women that I work within the entertainment industry have their own businesses and realize that they can be entrepreneurs as well because you make millions of dollars for these giant corporations, okay, you get a decent salary, but you're not getting the real rewards and profits from the industries.

So I think the future is very bright. I think incubators like Black Girl Ventures that support and provide the resources and the knowledge and the community are super essential to growing as a business and as a community, leaning on others in participating, which is really on the person. I know I'm not the most active all the time, but I go on, read the posts and newsletters, and see what's going on. Like the resources that are provided are invaluable. It's amazing."

If you and I were meeting three years from now, looking back, what would it take for you to feel over the moon about your progress?

Win Win Coffee Bar would like to be the leading coffee roaster distributor in the Northeast. Then hopefully, the second location for their roasting facility will be either in Philadelphia or another mostly Black city. She sees Win Win Coffee Bar expanding to cities like Atlanta, Detroit, and St. Louis. They may even consider having a coffee resort in Jamaica.

How do you measure success?

Success is quite simple for Nikisha. It's her waking up every day and being happy doing the things you want to do. Leading a life without regrets or doubts and intentionally removing the 'what-ifs' from her day today.

Running a business while balancing a personal life can be demanding and taxing. How do you take care of yourself?

Nikisha taps into her core friendships for support. She does this when she recognizes that she's working too much or possibly being irrational with her decision-making. Nikisha enjoys getting manicures and pedicures and treating herself to a spa day. This year she's focusing on her health. She said, "I wanna make sure I'm around for the next 40 years, so this business can actually grow, and I can start something else and start the next chapter of my life. So focusing on my physical health too has become a big priority for me."

What is your favorite quote or mantra?

"Practice makes improvement. You can always better your best."

What is a book that you would recommend?

Podcast: Access and Opportunity with Carla Harris

Book: Strategize to Win: The New Way to Start Out, Step Up, or Start Over in Your Career by Carla Harris

​​What's your favorite business hack or app you can't live without?


What's one food item that you have a hard time saying no to?

Anything with noodles.

What's next for WIN WIN Coffee Bar?

Win Win Coffee Bar is launching a new roast, an Ethiopian blend, and then will also launch a Kenyan blend later in the year. They also plan on doing influencer partnerships to reach more consumers with limited edition blends specific to the artists they partner with. All the proceeds will go to the nonprofit of the artist's choice.

Any last words…

Nikisha shared, "I will just say that the Black Girl Ventures experience has been incredible. It's an awesome network. And even just like people, or Omi being like you need a capability statement and I'm like, what's that?

She's like, girl, how are you going to—I'm like, all right. So even just all the feedback, cause like you don't know what you don't know, and it's so priceless to have a community that will tell you, this is what you need to know."

Subscribe to the Digital Orange Juice for juicy ideas and the people who fund them. You can find out about our next pitch competitions. Also, be sure to join our new community BGV Connect!

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