Inspiration comes from all different places.
—Jeffrey Katzenberg, CEO, DreamWorks Animation.
Oprah Winfrey and Henry Louis Gates Jr.
Oprah Winfrey is known for making guests on her show cry. However, this time, she was the one who would shed tears, overcome by the significance and serendipity of the moment.
In 2007 I stumbled upon a television special titled Oprah’s Roots: An African American Lives Special, in which producer Henry Louis Gates Jr. revealed shocking news to Winfrey about her family history. Gates, head of Harvard’s Afro-American Studies program, researched Winfrey’s family history extensively and decided to share what he found in a television special. The revelation was astonishing.
Gates shared that Winfrey’s great-great-grandfather, a former slave, bought a large amount of land and built on it a school for African American children. Considering the times, this achievement was extraordinary. When Winfrey learned this amazing piece of history, she was speechless. Tears came to her eyes. A blank stare turned into a confident smile. Winfrey, whose passions are education and land, instantly made the connection to her trailblazing ancestor. Like him, she built a school for young children and owns quite a bit of land. Oprah found renewed meaning and validation of her purpose in life. (Coincidentally, my wife and I went horseback riding on Winfrey’s land in Hana, Hawaii, in 2008. We learned then that her land there was one of several properties that she owns around the world.)
While watching the television special, I couldn’t help but get emotional, too. I felt tremendous joy for Winfrey and hope for myself that someday I would find someone in my family who was a trailblazing entrepreneur. As a young entrepreneur I struggled to find positive affirmation from my family that entrepreneurship was an honorable and legitimate path. Having a network of friends and associates who are entrepreneurs is wonderful, but having supportive family members—extended or immediate—makes a difference.
My older brother was the closest to an entrepreneur. Having graduated from Berklee College of Music in Boston and traveled the world playing jazz piano with Wynton Marsalis and Herbie Hancock, he was in charge of finding his band’s gigs, booking the band, and paying band members. He created a company through which he produced his CDs and managed his piano-tuning appointments. Other than my brother, no one in my immediate family was close to being an entrepreneur. On both sides of my extended family, everyone worked a normal 9-to-5 job.
I would later find out just how rare entrepreneurs are. According to the Kauffman Foundation, Atlanta ranked second among top metro areas in 2011 in the creation of new business. In 2011, 500 out of 100,000 adults ages twenty to sixty-four started a business. Los Angeles was the top city with 580 out of 100,000. That’s approximately 0.58 percent in the most entrepreneurial city in the United States. No wonder it’s so hard to find a family member who’s an entrepreneur.
My paternal grandmother was born in 1912. I never thought that she would be the link to connect me to relatives who owned their own businesses. When encouraging my siblings and me to watch a video of my grandmother talking about her life, my father mentioned that she had a brother who owned a grocery store. After asking my dad to tell me more, I learned that my uncle Thomas and an uncle Dan were my enterprising great-uncles. Uncle Thomas would deliver groceries with his horse and buggy, while Uncle Dan would make trips to the coal mines in Pennsylvania to collect coal to sell in Baltimore. After learning this, I didn’t come to tears like Oprah, but I searched for and found a connection. I wasn’t so odd after all.
Choosing to be an entrepreneur can be a lonely endeavor and experience, especially if no one in your family is one. But I encourage you to do a little research on your family, and chances are you will find someone who took the same risks that you did. Just like Oprah Winfrey and me, you will find that one brave family member who gives you extra inspiration and makes you proud. As the character Charlotte Phelan said in the Academy Award–winning movie The Help, “Courage sometimes skips a generation.”
