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BLOG | Nikisha Bailey: Stirring Up the Coffee Industry with Win Win Coffee


In the dynamic world of startups, where innovation meets passion, Nikisha Bailey stands out as a visionary entrepreneur whose journey from a music executive to the forefront of the coffee industry tells a story of transformation, purpose, and impact. Nikisha has harnessed her leadership skills, passion for community building, and a keen eye for opportunities to create something truly remarkable in the coffee sector.


CoffeePLUG and Win Win Coffee are two initiatives to revolutionize the coffee supply chain by introducing transparency, efficiency, and fairness. Through these platforms, Nikisha seeks to bridge the gap between coffee farmers and buyers, ensuring that the fruits of labor are justly rewarded and that the industry as a whole moves towards a more sustainable and equitable future.


In this exclusive interview, Nikisha shares insights into her inspiring journey, the challenges and triumphs of building a startup, and the profound lessons learned along the way. Join us as we delve into the mind of a woman whose life mantra, "always bet on yourself," has propelled her to new heights in the pursuit of creating meaningful change.


What inspired you to start this particular startup?


A desire for meaningful impact sparked my journey from a music executive to the world of coffee, and I knew that I had the leadership skills and knowledge to build something that was mine.


Witnessing coffee farmers' challenges and the industry's disjointed nature, I saw an opportunity to bridge gaps, foster transparency, and empower buyers and farmers. This transition directly aligns with my passion for community building and positive change.


What problem or pain point does your startup aim to solve?


Both Win Win Coffee and CoffeePLUG aim to address the coffee supply chain's disorganization and lack of transparency. By leveraging technology, we seek to create a seamless and transparent platform that connects buyers directly with farmers. Our goal is to eliminate inefficiencies, ensure fair compensation for farmers, and contribute to the overall improvement of the coffee industry.


What are the biggest challenges you anticipate in building and scaling your startup?


Building and scaling CoffeePLUG had unique challenges, including market adoption, technology implementation, and fostering collaboration within the industry. Additionally, ensuring that our community-centric approach remains integral to our growth presents an ongoing challenge we are actively addressing.


What were the key experiences or moments in your career that led you to pursue entrepreneurship and start your own company?


My experiences as a music executive exposed me to the power of collaboration and community building. This and a desire for meaningful impact inspired me to transition into entrepreneurship. Witnessing the potential for positive change in the coffee industry fueled my commitment to create CoffeePLUG and Win Win Coffee.


How has your background and expertise prepared you for the challenges of leading a startup in this particular industry?


My background in the music industry equipped me with valuable skills in collaboration, innovation, and understanding market dynamics. These skills, coupled with a passion for community impact, allowed me to navigate the challenges of leading a startup in the coffee industry.


How do you handle failure, and what have you learned from past entrepreneurial experiences, if any?


Embracing failure as a learning opportunity has been a key aspect of my entrepreneurial journey. Each setback has provided valuable insights, enabling me to refine strategies, pivot when necessary, and strengthen our approach. Resilience and adaptability are crucial elements in overcoming challenges.


What skills or qualities do you believe are essential for a successful founder, and how have you cultivated them?


Successful entrepreneurship requires a combination of resilience, adaptability, effective communication, and a deep understanding of the industry. My journey in the music industry has honed these skills, and continuous learning and collaboration are key to staying ahead in the dynamic startup landscape.


My mantra in life is to “always bet on yourself.” No one knows your goals, your desires, and what you are capable of more than you. Lean in on those things, and always know you are your biggest champion!


What advice do you have for aspiring entrepreneurs based on your own experiences?


Embrace your passion, stay resilient in the face of challenges, and never underestimate the power of collaboration. Surround yourself with a diverse and talented team, and don't be afraid to learn from failures—they are stepping stones to success. And don’t forget to always bet on yourself!


Can you describe your fundraising strategy, including the types of investors you target and why?


Our fundraising strategy is focused on securing support from investors who align with our mission and values. We seek partners who share our commitment to positive impact and sustainability. Building a diverse investor base, including those with industry expertise, is crucial for our long-term success.


What mentors, role models, or advisors have influenced your approach to entrepreneurship, and how have they shaped your thinking?


Influential mentors and advisors have played a significant role in shaping my approach to entrepreneurship. Their guidance has provided valuable perspectives, helping me navigate challenges and make informed decisions. My village is everything. They support, advise, mentor, and bring me back to the reality that’s needed!


A great leader knows that they don’t always know the answer to every question but have the tools within their wheelhouse to figure it out and get the job done. 


What motivates you?


My community is the next generation of entrepreneurs, people who wake up every day and are committed to doing what they love. I’m motivated by so many things, but most importantly, I’m motivated by myself and knowing the challenges I’ve had to overcome personally and professionally to get to where I am today.


Creating positive change in the coffee industry is also a powerful motivator. Knowing that CoffeePLUG and Win Win Coffee can contribute to a more transparent, equitable, and sustainable supply chain while fostering community development fuels my passion and dedication to our mission.

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