One Of Ones: Lessons From Oprah

Winfrey's career is a reminder of the importance of betting on yourself—and knowing when to let others bet on you, too.

I’ve never interviewed Oprah Winfrey, but I did spend the better part of a decade counting her money. As the media & entertainment editor at Forbes, I oversaw our annual Celebrity 100 issue, which measured the annual earnings of the world’s top entertainers. And Winfrey topped the list so many times that her success almost ceased to be news.

I remember the collective sigh of relief in the office when Winfrey decided to wind down her eponymous talk show and focus on her Oprah Winfrey Network (OWN). The move meant other stars would have a chance at the top spot as she built out her new project, and that our list might have a different look from year to year.

Winfrey was able to start OWN because she’s a true one of one, overcoming the unimaginable circumstances of her youth and turning into one of the world’s most beloved personalities. She’s also among the wealthiest, becoming the first-ever Black woman billionaire in 2003. Winfrey now boasts a net worth of $3 billion, placing her among the richest 1,200 people on the planet.

This phenomenal level of achievement—despite the longest of odds—is why Trapital founder Dan Runcie and I delved into Winfrey’s career in the latest installment of our “One of Ones” series. Check out our podcast episode here; my written breakdown on lessons I learned is available to paid subscribers, as usual, below.

Winfrey’s story is inspiring on myriad levels, but one of the most significant decisions in her professional life was founding OWN. And the choices she made in terms of timing, planning, and structure make for a fascinating case study when it comes to the business of ownership.

Here are three lessons that stood out above everything else.