Lauri Lyons: For your big stories that you’ve covered (Hurricane Katrina, Thailand tsunami, Haiti earthquake) what are the logistics and preparation time for getting you in the field and on camera?
Soledad O’Brien: I’m sitting in traffic on my way to Newark airport. So, I’m living your website. The logistics are usually pretty crazy, but I work at CNN, and they are pretty amazing at that. They are just masters of logistics. They would have a whole apartment, and then their goal is just to get you physically there. Then I travel with stacks of books and printouts, and any information I can find. While I’m on the flight, I’m reading. We’ll often travel without knowing very much.
For example, I know there’s an earthquake in Haiti, but what’s the history of Haiti? How did Haiti become a country? What are some of the big stories and issues in Haiti? You spend the entire flight reading until you really understand all the different contexts of the story, while somebody else is trying to figure out how to get you in. Then you get in there, and, depending on what show you’re assigned to, you hit the ground running.
We would take naps for forty-five minutes at a time and work in chunks. The time difference was such that when you’re supposed to be sleeping, you actually have to be working. Having someone amazing handling your logistics, so you can handle the content and storytelling, is really important and essential. It’s about teamwork. Everybody doing their job will ensure that all different parties know where they need to be.
Sometimes the context is a little challenging, it’s a little chaotic. A good example is the Haiti earthquake: I was on a plane in the Dominican Republic and I ran into Vin Diesel on the flight. He was going to chopper in from the Dominican Republic into Haiti, and he offered me a seat on his chopper and so I took it! That’s how I got into Haiti to cover the earthquake. It’s about being a little resourceful too.
Lyons: Every story is different, but generally how long are you in the field on assignment?
O’Brien: For the Thailand tsunami, I was there for three weeks. Usually, I like to say the wheels go off in my personal life after about three weeks. For Hurricane Katrina, we used to rotate every two weeks, so you’d be in the field for two weeks and then you’d swap with your co-anchor, and he’d go into the field while you’d stay home. That was really helpful, because my kids are little and they need homework help, and you need to do errands and just live your life and get stuff done when you’re at home.
After three weeks in Thailand, when I got home it was a mess. I was very happy to be home, but my kid’s hair had to be done, and everybody was wearing mismatched clothes, etc. Now that I’m not covering as much breaking news, a week is a long trip for me. I tend to keep my trips to under a week. Usually, it’s a trip that I’m going to a bunch of different places,so I’m traveling with a lot of different outfits, probably going to meetings and covering the news.
Lyons: Now that you have launched your company Starfish Media, what is a typical shoot day for you?
O’Brien: I have about five jobs, I’m a reporter, but I’m also running a company and I’m leading meetings. We’re also trying to figure out new business and coming up with interesting proposals around how to do stories. We’re developing shows, so a lot of my time is spent in developing meetings and reporting, whether it’s for WebMD or HBO Real Sports. A lot of my time is also spent on planes, heading to conferences or meetings.
I just was at the White House for the United State of Women Conference, which was fascinating. I was there on Tuesday, Wednesday, had a drink with a friend, who I’ll probably begin a project with, and then Wednesday night I jumped on an 8pm train and got back to my house at 12:30pm. In the morning I got up to do hair and makeup for a shoot and drove into New York City to do the shoot. Afterwards, I had a bunch of meetings, and now I’m heading back to the airport to go to LA.
Lyons: You literally have a 24-hour life?
O’Brien: Yeah, at the end of the day, Starfish Media is a start-up business. When you’re in a start-up, then you’re in start-up mode, which means you just work a lot, and you do a lot of jobs because you’re building something. When I was a reporter for a morning show, that’s sort of a start-up. You’re one of the millions of people working to try to get something done, and that’s a very different gig.
Lyons: How do you feel being the CEO of your own company is making you grow?
O’Brien: Oh my gosh, it’s been so much fun. I would not have said that two years ago because the first year was really hard. I had to learn everything and it wasn’t just how to run a company, it’s how do you be in charge? How do you hire people? How do you find space? How do you have operations? How do you get insurance for your company? Who can I partner with to bring these things that were just in my head, to life? How do we turn them into a real, successful business?
It’s this whole structure that you have to know. Every day felt like a really sharp learning curve, and I would literally say, “Oh god, could this be a day when I don’t learn anything?”, but I did and it was fine. Everything is learnable, and about a year in I finally realized I completely know what I’m doing. I knew that I wanted to do this, and it’s really fun to be able to do whatever you want. That’s very exciting.
Lyons: What has been your most challenging, or favorite, place to cover or produce a story?
O’Brien: I did a story on the Today Show where I had to go check on all the different expats who were running businesses in other countries. I was sent to Anguilla, which, as you can tell, was a scam of a story. I spent days and days in Anguilla, eating really good food and talking to Americans who had gotten sick of America and had gone off to live on an island. That was pretty amazing. I love going to new places to report. I love exploring cities and roaming around the country to really see American cities. I think the hardest part is all the places where there were terrible tragedies. It really changes how you feel about a place when you’ve been in sight of the worst violence or something really terrible happening.
Lyons: How do you emotionally leave a story behind?
O’Brien: I like to think that reporters have a job and that job is never about you. You’re just there to try to do the best you can for other people. You need to ask thoughtful questions because they don’t have the mic and you have a responsibility. I try to use the time and the mic as best I can to be useful and helpful. I think that has really helped me psychologically when I untuck stories. I feel like this is not about me, and I can get through to these people, whoever the people are that are affected. I can be of service to them if I simply do my job well.
Lyons: What are some of your “must-haves” for your suitcase?
O’Brien: Oh, I’m making my little bag of trips right now. So, my kids got me, for Mother’s Day, a really great cashmere bag, and inside are a cashmere scarf, a blanket, and a cashmere eye mask. It’s been the greatest thing. I carry it with me when I’m going on a plane for more than an hour and a half. I love that I have this snuggling-up gift from my kids - it’s awesome and it’s really useful! I’ve really come to rely on it and I love it.
The other things are low-heel shoes. I’m telling you, I’m turning fifty this year and I do not walk around in high heels anymore. I will wear them on TV, I will wear them for interviews, but I’m not gonna schlep through Newark Airport in 3-inch heels. They’re insane. I make sure to have really cute, comfortable, low-heel shoes that I can slip on, and when I get to my location I whip them off and I put on my heels.
Lyons: Do you have any unusual or personal travel rituals?
O’Brien: I really don’t. I think I am just a very efficient traveller. I land, I unzip, I hang up my bag, and I usually go to bed right away. I try to get up early in the morning, get ready to go very quickly, and I start my day. Because I have four kids, If I have a personal day in my travels I may go sit in the hotel lobby and just people watch, write in a diary, and just take a moment to thank the place for the quiet. It’s just a little break away to just enjoy a moment of quiet.
Lyons: Now that Cuba is opening up for tourism, do you have any plans on doing any reporting, or personal travel there?
O’Brien: Absolutely. We’re pitching a handful of stories in Cuba. I go as a reporter, every two years or so. I was just there in March to interview the President about entrepreneurship. I’d love to go to Cuba again. I think there are a million stories to tell there. I also think there’s just a tremendous interest in Cuba.
Lyons: I was surprised to learn that you and your family house-swap for vacations.
O’Brien: Yes, so we have done that. We did a house-swap in Rome, Paris, Barcelona, Capetown, and Panama. Last winter we went to Uruguay for two weeks during Christmas, and it was beautiful and amazing. I love sleeping in a house when I travel. I live in hotels all the time. A fancy hotel is just not my thing. And when I travel for vacation, I don’t want a fancy hotel. I love being in someone’s comfortable home, in their comfortable house, with my feet in their beautiful pool.
I loved the house-swap. It’s just so successful, especially with four kids! Honestly, it’s not that comfortable to travel with four kids in a small hotel room. It’s really expensive, and it’s not fun for them. When you’re in a home, usually there’s a place for them to play. In Paris, my kids used to put on plays. They did a whole series of them. The house that we were staying in, had two little boys, so they would play with their toys, and put on plays! It was a great way to see Paris, because you’re hanging out, instead of sitting in your hotel room and watching TV. I highly recommend it.
Lyons: What do you think your personal and professional travel experiences have taught you about yourself?
O’Brien: I think travel teaches you a lot of things. I think it teaches you to suck it up and get through it. I think you learn about people through travel. If you’ve never seen anybody fall hard on a trip, you think “Oh, this person isn't for me.” You find someone else. If you can’t handle the fact that we’ve lost our way, or we took the wrong bus and ended up on the wrong side of town, then this is probably not going to work out.
You learn about yourself. You find out that you’re resilient. You can figure your way around. There’s nothing more empowering than landing somewhere, not speaking the language, and having to navigate not just getting to the house you’re living in, but the supermarket. It’s funny, one year, in Paris, we ended up with six giant plates of french fries. I remember thinking, “Oh, that’s not what I wanted at all!” The kids were like, “Oh my god, this is amazing!” I think I said the wrong thing. I was trying to order something else.
I hope that when you go somewhere, that you just have fun, and you mess it up, and you try again, and you meet people, and you have experiences. Something goes wrong, and maybe you get another interesting thing that you weren’t planning on. I think travel sort of reveals the amazing mess that’s in store for life, and when you put yourself out there, you just kind of free yourself up to experience things, and you can have a really tremendous experience.