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

Jeff Cunningham got a chance to speak with TV personality and business leader Soledad O'Brien about what it’s like being a CEO, negotiator, and still occasionally, a mother of four.
Soledad O’Brien Photo: Jeff Cunningham

Soledad O’Brien is one of the most recognizable faces in America. Her three-time Emmy award reporting has taken her from opioid dens in San Francisco to the hurricane-ravaged streets of New Orleans. But they are only a part of her amazing story of growing up in a mixed racial family and making her way from Harvard to the TV anchor desk and now as CEO of Starfish Media Group, her production company headquartered in New York’s Madison Park media village. I had the chance to talk to O’Brien recently about what it’s like being a CEO, negotiator, and still occasionally, a mother of four.

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 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 ever have to stay on top of your employees?

SO: In our office, I do not want anybody who has to feel, ‘Soledad needs to see me come to the office to do my job.’ If you’re sick, don’t come in. If you’ve got good ideas, let’s go figure out how to get them funded and make them happen. I try to hire smart people and then set them free to do what they want to do.

JC: What are some of your ‘art of the deal’ tricks?

SO: I’m a very straightforward person. Some people love to go back and forth, and it’s a game for them. I say, ‘Here’s what I want to achieve. Here’s what I’m willing to pay for it. This is what I want to do. Do you want to be part of this?’ Sometimes the answer is, ‘No, we’re not going to see eye-to-eye. Maybe the next go-around we’re both going to be able to hit the things that we need to move forward.’ I always think of negotiating as, ‘Let’s save each other three-and-a-half weeks and lay out what we need, and we can get this deal done by the end of the week.’

JC: When you’re interviewing someone, how hard is it being a celebrity?

SO: First of all, Madonna’s famous, Beyoncé’s famous. I’m someone who’s on TV. People are more like, ‘I loved that story,’ or sometimes, ‘I hated that story,’ and they feel very comfortable telling you what they think. In interviews, the onus is on the interviewer to make the other person comfortable, and it’s my job to make them feel at ease, ‘once we start, we’re just going to have a conversation.’

JC: In your book, you often refer to your upbringing in shaping who you are. Do you bring that to the workplace?

SO: My parents were not entrepreneurs although they were very straightforward and kind of strict. I don’t think of myself as strict with my employees. I think I’m just clear. ‘This is what I need. Here’s what my expectations are.’ I try to do the way I like to be treated. I want to know what the milestones are and what the deliverables are and what the timeline is, stop me if I’m screwing this up, and tell me what I’m doing wrong. I always appreciated bosses who said, ‘Here’s what I need.’

I didn’t like bosses who played games, and TV news is full of people who play crazy games, ‘Are you happy today? Are you not happy today? How are you feeling?’ Who wants to waste everybody’s time?

I like to come in in a good mood. I like the workplace to be a really pleasant place. I never enjoyed going into offices where someone was psycho mad, and everybody had to walk around on potato chips. Who wants that? I like the office to be fun. I hire nice people. I fire people who are not nice.

At some point, it’s just, ‘Let’s end the drama and focus on the fun part.’

Read more: Ralph Lauren Is Being Disrupted In Real Time


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