Entrepreneurial Vibes from Musical Genius John Legend

by Diana Drake

When John Legend joined a virtual Wharton Venture Lab celebration this month to accept his Penn Wharton Entrepreneurship 2021 Alumni Achievement Award, he shared a story about when he was a teenager growing up in Springfield, Ohio. When he was 15, he entered a Black History Month essay contest sponsored by McDonald’s in which he answered the question: How do you plan to make Black history?  

“My answer in 500 words or less was that I was going to make it in the music business, become a successful artist and use my platform to fight for justice and equality for my people,” recalled Legend during his conversation on March 3 with Wharton Dean Erika James. “I was so interested to read about civil rights heroes, people who fought for justice and fought for equality. It always struck me that they lived really impactful lives and I wanted to live an impactful life. I wrote that [essay] when I was 15 and had forgotten about it. When I was embarking on my career, my dad reminded me of it, and when I reread it I was almost in tears because it was so prescient saying exactly what I ended up doing in my life.”

While many know Legend as a celebrity singer, songwriter, record producer and more, fewer know his passion for social causes, especially criminal-justice reform and education. His accelerator Unlocked Futures, for example, supports entrepreneurship as a pathway for people who have been affected by the criminal justice system to earn an income and build a career.

For these endeavors, as well as his own personal entrepreneurship journey that led him to build a multi-platinum music career, and start businesses like Get Lifted Film Company and LVE Wines, Legend, a 1999 University of Pennsylvania grad, won this year’s Penn Wharton Entrepreneurship Alumni Achievement Award.

“It’s hard to make it as an artist without entrepreneurial spirit,” said Legend. “So much of what you’re doing is presenting yourself as a new business and a new idea and a new entry in a crowded field of musicians. You’ve got to find a way to convince funders (record labels, usually), and your customers that you’re a new company worth investing in and buying products from. My first big entrepreneurial move was to decide to embark on this career as an artist…and get my music out in the world.”

“How do I show love for people that I don’t even know?” — John Legend, Entrepreneur

Entrepreneurship, and the characteristics that define this business mindset, have continued to guide Legend’s path forward since college when, even as an English major, he was “very influenced by my Wharton undergrad friends.”

Threads of inspiration woven throughout his experiences reflect one or all of the following principles:

Humanity. Connecting with the people you hope to serve and understanding them deeply can take your entrepreneurial pursuits to a new level, which has helped Legend in his work with people leaving prison. “Dr. Cornel West [political activist] said that justice is what love looks like in public,” noted Legend. “I think what he meant is that if you love people that you don’t even know — people who may not look like you, may not worship like you, may live across the country or across the world — it shows itself in policy, in justice and equality. I use that as a guiding force for how I think about my activism…How do I show love for people that I don’t even know? How do I show love for people who may be overlooked? Who may be under-resourced? Who may be oppressed or who may be outcast because they look differently or love differently or worship differently?”

Collaboration. Part of differentiating yourself “is collaborating with the right people to do it together and learn from each other to create something new you wouldn’t have done by yourself,” said Legend. “I learned from my own journey…It took a lot of time and collaboration, working with people who inspired me and pushed me and challenged me.”

Persistence. “So much of what is going to happen at the beginning of any kind of entrepreneurial venture is you being told no; you being told you’re not ready yet, being told to wait. You’re probably like: ‘What do they know!…I know I have something great to offer.’ I was thinking that as a musician. I’m ready! What do these labels not see in me that they should be seeing? You have to take that feedback, learn from it, grow from it and be persistent,” advised Legend. “Have grit, have determination, have that perseverance and resilience to get through all those no’s until it’s time for your yes to come. A lot of times their feedback can let you hone [your idea] and shape it and mold it in the way it needs to be molded until it’s really ready for prime time. Even though I wouldn’t have admitted it to myself at the time, I can in hindsight say that a lot of the feedback and constructive criticism that I got back then really helped me become a better artist.”

Related Links

Conversation Starters

Did you ever enter a public essay contest like the one John Legend recalls? What did you write about? Did it help you focus in on what you have to offer the world?

Why do you think John Legend focuses on humanity as an important awareness in his own business journey?

Constructive criticism almost always improves our ideas, products, services and contributions, and yet, we can resist people telling us that we have more to learn. Describe an experience where you embraced the value of feedback in your own life — or rejected it. What was the outcome?

4 comments on “Entrepreneurial Vibes from Musical Genius John Legend

  1. As an Asian American growing up in China and coming to the US in my later middle school years, I experienced cultural shock and conflicting standards. People deemed me too ‘American,’ which implied arrogance based on their stereotypical analyses of Asian Americans in China. In contrast, my acceptance to the US wasn’t welcoming either. I was unaware of essential American customs like greetings and slang and clueless about the hip-hop rap culture, American football and the Superbowl, and academic expectations. I wasn’t just introverted but, rather, unable to find a starting spot to talk to others beyond the introductory level.

    “How do I show love for people that I don’t even know?”


    John Legend’s evaluation of his pursuits, goals, and ambitions of becoming a musician is strikingly similar to mine. I used my passion for popping (a hip-hop/funk dance style) to communicate with others, showing that I share a common love for music and am eager to meet new people.

    I recall anxiously walking to my first ever theatre class at the new middle school, afraid of the unknown – what to expect, who the people are, and how to socialize. It was during one of the dance-to-the-music exercises where I, the only Asian student in the classroom, caught the attention of my peers. I remember how I closed my eyes and subconsciously started doing arm and body waves to the soothing music, only to realize that my classmates were staring at my peculiar yet ‘cool’ movements when the exercise ended. From then on, people introduced themselves to me, opening me up to the American lifestyle and helping me form self-confidence and new friendships. From then on, I took the initiative to approach my classmates and shared my dancing story with those interested in learning. Inspired by the overwhelming support, I established a HipHop club, where I taught interested students simple dance routines and showed them videos of popping professionals, introducing them to my world.

    I believe my journey ties to John Legend’s pursuit of showing love and connecting to those who are different from you. Just like Legend said, “I learned from my own journey…It took a lot of time and collaboration, working with people who inspired me and pushed me and challenged me.”

  2. John Legend’s message of pursuing his dreams while leading a meaningful life and giving back to the community is a powerful testament to how life should be lived and the value of giving back to the community while pursuing one’s dreams. Legend says giving back to the community is important because it can serve as a time to connect deeper with the community, and this then will lead to a more fulfilling entrepreneurial endeavor. There has been a time where we all have dreamed of achieving our goals: opening up a business, becoming an actor on the big screen, or singing in front of a crowd and hearing cheers of your name from every direction. However, with these big dreams, we often lose sight of the people who are cheering us on and why we decided to embark on this entrepreneurial journey in the first place. Legend is a prime example of someone who hasn’t lost sight of his purpose during his entrepreneurial journey. He has been able to combine his love of singing with his passion for speaking out on social issues and social rights, making the path for a long-lasting career that has been successful but also very meaningful. Legend’s soulful tunes show his earnest need to give back to his community and connect with others. In today’s business world, young entrepreneurs should learn from Legend’s story and experience to ensure that they find meaningful work and give back to the communities where they live.

  3. Quarantine restrictions gave some of us the chance to reflect on ‘who we really are’, the striking question of ‘what is the meaning of life?’ and most importantly ‘how will life be carried on once this is all over?’. These questions, in some ways, helped guide us to the paths we most wanted to pursue just like John Legend’s essay.

    During the numerous months stuck at home, I came across a box of memories, stashed with trinkets and tickets from events, name tags, medals and written notes from new friends. These objects were my ‘forgotten’ course that led me to where I am now – a place I dreamed to be in as a child. It was my version of John Legend’s essay. The article changes the question of ‘what will life be after’ to ‘what is your action-plan on fulfilling your dreams to the next level’, especially in the given circumstances, or in other words ‘what are you going to add to your memory box to become even closer to realizing your passion’.

    My memorabilia is the representation of my assets – my worth as a contender in the industry – as we present ourselves as ‘new businesses’ as mentioned by John Legend. Thus, we need to survive, gain experience and skills, and grow as individuals with an entrepreneurial mindset. This would help us analyze ourselves as the ‘new idea’, finding routes and considering options best for us to progress and fill in gaps. No matter our dream, dedication to research and develop ourselves would bring a competitive edge, especially by first answering our question of how to continue achieving our dreams even with the limited opportunities provided by the pandemic.

  4. John Legend provides a truly inspirational figure as a successful Black musician and as a person who strives to give love and share it with everyone around him. Reading about him reflecting upon his old essay and further connecting it to what he believes is needed for musical success reveals all of the intertwined chains between the music industry and its consumers

    Black people and other people of color have continuously had to deal with attacks: George Floyd, Breonna Taylor, the Atlanta spa shooting, the attacks on elderly Asians, and many more. Online and offline, POC has been advocating for their rights to be recognized, for their feelings to be acknowledged, and for action to be taken. When John Legend talked about connecting to his audience and understanding them as a part of his business, he truly is correct in this aspect. Music artists, actors, Youtubers, streamers; all have an incredibly large influence over a massive population. So it comes as no surprise that when we want to spread education and information for our movements, we’d love it if our favorite influencers showed they cared by helping us spread awareness. It doesn’t take much effort, and even the smallest bit goes a long way. When an influencer refuses to acknowledge or support these human rights issues because they don’t want to “damage” their image, they often lose a large portion of their fanbase.

    Thus, every single influencer should take note and realize that their profession is, in reality, entrepreneurship. How you connect with your audience and how you react to what the audience wants creates the basis of your business. “How do I show love for people that I don’t even know?” You show genuine support for the issues that affect your audience. You recognize that you need this audience to keep your business running. When you make mistakes, you realize and genuinely apologize. John Legend’s words go beyond the music industry; they are words all influencers should carry when they think about how they can persist and continue to allow their businesses to grow.

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