The Thing Soledad O’Brien Learned By Starting Her Own Company

Jeff Cunningham
4 min readMay 20, 2019
Soledad O’Brien, TV anchor and CEO Starfish Media Group

Soledad O’Brien is one of the most recognizable faces in America. The former CNN anchors career has brought her three Emmy awards and dragged her into opioid dens in San Francisco through the hurricane-ravaged streets of New Orleans.

O’Brien’s career has taken off once again. She has made the transition from the TV anchor desk to Starfish Media Group, her production company headquartered in New York’s Madison Park media village. In our interview, she spoke candidly about her role as lead negotiator, creative boss, and still occasionally, a mother of four.

JC: What was your biggest first-day surprise in launching a company?

Soledad O’Brien: When you walk in and realize ‘the garbage cans don’t empty themselves, what?’

JC: What was the most difficult part about starting your business?

SO: What surprised me was how hard it was to build a team because you have to hire people for an area that you’re not an expert. For instance, I had to hire an editor. But I don’t know enough about editing, so you need to figure out how to be sure you’re not doing a bad job hiring because of your weaknesses.

JC: With so many projects, how do you stay focused?

SO: It’s very easy to spin your wheels. You have to say no to a lot of things. For me the first couple of years I said yes because I was panicked, ‘We’ve got to get this business going,’ Then really it comes down to what’s worth my time?

JC: What new skills did you have to develop as an entrepreneur?

SO: I’ve been a reporter for a long time. Then it turned out I was very good at negotiating, which I would never have thought. I like structuring deals. I love negotiating with people. It’s exciting to find something that you’re good at that’s different than the thing you thought you were good at. The part I like best about being an entrepreneur is that every minute of the day I’m doing something that I want to do.

JC: Do you need to stay on top of your employees?

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