Keith Olbermann's Curious Course to Career Success

or from his career as a commentator on MSNBC. This week on Game Plan, we're talking about his drama filled career where he got fired and rehired and apparently burned bridges along the way. I'm Rebecca Greenfield, a reporter at Bloomberg where I cover workplace culture, and I am Sam Grobart. I am a writer at Bloomberg Business Week magazine. So Keith Olrin's career from the beginning was filled with drama, Yes,

from day one, essentially. Yeah. When he worked at up I Radio, he was almost fired and the only thing that saved him, according to a New York article, was his guild. Oh well, that's helpful. But he's continued this pattern quite successfully of going places, being very successful, and then getting very fed up, frustrated, some contention with his bosses and bolting. Yeah, do we think it's useful to just give like us quick rundown of the firings and hirings.

I mean we have to do all of no, no, no, Here I can pick out some of the highlights, So here we go. Berman joins ESPN, He's there for five years when he leaves acrimoniously in He then goes over to MSNBC, but leaves there two years later when he joins Fox, but he's fired from there in two thousand one. In two thousand three, he goes back to MSNBC, but he's suspended from MSNBC in two thousand ten and leaves in two thousand eleven. In July two thousand thirteen, he

goes back to ESPN. He leaves that network for the second time two years later. Right, So what's crazy besides that he's boomeranged around these various companies is also the stories that have come out of this. When he left ESPN that first time in seven there's a famous quote saying he didn't burn bridges, he napalmed them like a cool guy. Yeah yeah, And when he left Fox, I believe Rupert Murdoch said he fired him because he's quote crazy as opposed to all of the incredibly sane people

that Rupert Murdoch has kept in his employees. Yes, really great point. Yeah, yeah, yeah, yeah, maybe yeah, probably Yeah. Olberman is is to the left of Rupert Murdoch, and maybe that's why he thought he was crazy. Yeah, maybe that's contributed a little bit to it. Um, but really

it's hard to work with. I guess the question is this, Yeah, is he you know, should he be sort of um lambasted or feared as a difficult person or should he be sort of lionized for basically not giving a damn in a good way and saying I'm going to do what I do. I'm really good at it. If you've got a problem with that, you can take this job and shove it and finding another place where he can

continue to apply his craft. Yeah, as we were talking about this, I definitely had a little bit of Oh, maybe he's my work hero, right, Maybe Keith Alberman is sort of like what we all wish we could be, which is apparently permanently employable, obviously very well compensated, and with the kind of courage of his convictions to leave a place when he starts to feel like things are going south for him. Yeah, and he obviously is good enough to get hired back from these same places. That's

what's crazy. It's not like he's just jumped and dumped and dumped and dumped. He's he's so good in some ways that ESPN or MSNBC want to have him back even after reports of this friction, because whether he's Employee of the Month or the world's worst coworker, the fact remains Keith Olberman is a singular talent in broadcasting and that presumably affords him second and third chances that most of us would never get. Yeah, that's what we're going

to talk about with him today. Keith is here with us. He's our guest. He has a new web series at with g Q. It's called The Closer, and we're going to talk with him about that latest comeback and his

bumpy road to success. So why don't you start, Keith by telling us about your latest role at g Q. Um about August or so, I got a call from an editor at g Q named Jeff Ganion who had an idea that was similar one I did, which was, we would be a good idea if I was doing commentary on the campaign yeah, and I think ten days later we posted the first of them, which is not quite the record in my career for getting something started.

But what we posted a piece called hundred and seventy six reasons Donald Trump should not be elected or cannot be elected or however it has various titles, which has been in the following ten days or so seen somewhere around three and a half million times. So you made the decisions so quickly to take the job, yeah, because it was we knew going into this at both ends of it that there was gonna be learning curves for

both g Q and for me. But on the other hand, they weren't going to hold the election until we were settled and ready to go. And I had talked to a lot of people about doing something like this, and most of them were just, well, we're at the cutting edge of new media and we're going to do this, and we're going to do that, but we can't move quickly or anything. How About in January? And it's like, well, look in January, maybe these commentaries won't be necessary or

legal by then. So it's one of those two options. I'd like to just get on the air with it. Can we just get on the end. These these guys had the same idea I did, and the premise of it was similar to mine, which was, let's do it. Let me ask you another question, based on the experience you're having right now, do you think this is the future of people like you and the work that you do, which is to say, not necessarily being tied in a

very formal sense to one large entity. But you do g Q through the election, then you do something else for someone else, you know, by January, and you just kind of it could go in that direct. Let me put it to you this way. This is why I'm I don't have a distinct answer for it, apart from the fact that I can't see it clearly yet and I don't think anybody can. The first thing that was burned into my psyche when I started in the business.

The first two major national television organizations I worked for did not exist the day I graduated college and where the day I started in broadcasting. I started at network Radio in New York, so I was, you know, already the third or fourth level of the business. These places didn't exist. I've been on the air longer than ESPN, and that was the place I have the most success except for CNN, which didn't exist, an MSNBC, which was seventeen years away from exist. Thing, So you have to

adjust to it. If you're somebody who's working in the industry and this is you know, the possibility that you have a brand and then you marry your brand or date your brand to somebody else's brand is absolutely a possibility, and certainly we're doing that right now. Your career seems particularly well suited for that because I changed a lot over years because tattoos with with logos of companies. Yeah,

I mean, yeah, you're not particularly loyal to a specific company. Um, You've also not always loyal when I'm there, don't don't you know? I am actually a tremendous team player. It's one of the unfortunate things. You can't really convince anybody. How many teams have you played for? Yeah, but I was a team player for all those teams. But go ahead,

I'm sorry, Well, you've you've been asked a large audience already. Yeah, it's five and a half million as of the first six commentaries and one interview, which is a lot from a from a from a dead stop, right, I mean, we just there was nothing. This did not exist on Labor Day at all. Yeah, but I mean, we're build an audience. That's a really hard thing to do when you're just some people. Have you always had that view on your career, like I'm going to build an audience

for me. I'm in this for my own personal growth only in the sense of that old philosophy that is, if it does not interest you, it cannot possibly interest the person you're talking to. In other words, I never associated the salary with the work or how much effort I should put into it, or what it should look like. And I never I mean, the venue is sometimes important. You reflect to some degree who you're working for, and there are rules in some places that don't exist in others.

I always thought that I had an obligation to myself more than anything else, to do it in a way that matched my standards, And I would often get into conflicts with management places that didn't have the same standards, and I would be saying, I don't think we should do this, I don't think it's journalistically correct, and then they would say, well, you don't make that decision here, and I would say, well, I do make one decision here,

and then it go to somewhere else. If you're working just to be on so you can say at the end of the day, I work for such and such, forget it. I mean, there will be trained artificial intelligences who can take that job. You will be competing with the machine that never stumbles on the air. And I mean, if you're just going to be a voice, if you're going to have a set of codes and a point

of view. I think, no matter what the medium turns out to be, even if we're speaking telepathically to the audience, eventually and there's no equipment required to except a small chip here in one of your teeth, that will always be in demand. And it will also if you stick to that, it will also be every work experience will be valuable in someone. You talk about the relationship that you've had with some of your employers, how you will disagree.

You have the option to leave. Obviously you have done that. Was that always true for you from the beginning or did you come into that understanding later on in your career, and if so, what was that education. I was also like this as a child. Yeah. Now, I I tell you this is very interesting because my father, who had one full time two full time jobs in his life, and the rest of his career worked freelance. Said to me once I was leaving. My first job was at

United Press International. That's how old I am. And when I left, the guy said, why are you leaving? I said, because the way you treat the younger people here, the place isn't going to exist in ten years. And he said, oh, what do you think? There will always be a u p I. Within ten years, I was on TV and he was managing a restaurant in Katona, New York. Anyway, Yes, and he's a great guy too, but there just wasn't

a job for him. And he also it was he had enough of radio, so he left and was a manager. And I was going to leave, and I had two choices, and I wasn't sure because this was u p I. It had been in its two originators of United Press and News International, had been around since the nineteenth century. And the place I was going to have been around for sixteen months, and it was more money and sleeker studios and less work, and it was a brand new thing and it's like a young adult audience and all

the rest of that. And I still had a little hesitation in doing it. My father said, this is the first job you've ever been offered and I said no. He said, what was that other thing last year that you didn't take? That I wanted you to go to Boston? I said okay. He said, so that's you had, the one you got, the one in Boston, and this that's three. I said yeah. I said how old are you? I said, I think you should know this and he said how old are you? I said, I'm gonna be twenty two

next month. He said, so you think these are the last three jobs you're ever going to be offered? And I said no. He said, then what are you worried about? This doesn't work? Get something else. By that point, I had already had more jobs than he'd had. So I don't know where this wisdom came from, but it's always stuck with me. And I just think that's a good way to operate, and many people can't, and I don't criticize them for doing so. I don't think I'm better

than they are. I'm either smarter or much much stupider, and and it probably both. And it's probably also just to set a circum stances that I just I've never never sought security, and I've never wanted to compromise in exchange for security, and that often comes across as there's a bad employee in that sense. Yeah, I mean you're going to You're going to get what you get, and I am going to do what I think is appropriate.

And trust me, I have compromised a thousand times. It's not I don't, it's not I won't, it's this is fine. These firmpromises are fine. Number one is where I draw the way. Yeah, I think that's worth pointing out that, you know, some people do have to compromise and some

people are risk averse for other reasons. And maybe I don't know if you believe this, but do you think it's also particular to the profession that you or we are in, where all these things we're talking about about building a brand and skills are transferable and yeah, yeah, right, the advantages that you are likely to rise in this in any kind of medium format and any kind of media format based on whether or not you have a

personal appeal to the audience, and it's not it's not. Well, we like generic announcer number thirty two and he fits. He's new generic announcer number thirty two. It's not a character that's written for you. You You know, it's not Elizabeth, my friend, Elizabeth Montgomery's husband on Bewitched, who suddenly was a different guy in September, and I was like, no, no, there's nothing to all the characters are behaving like there's nothing wrong here, and he's just regenerated like doctor Who.

But you know that's fine. It's not like that. You are yourself and that is that is the brand. And the other thing I would point out in my defense in terms of this, it's not strategy, just it's a reflection of my personality. I have had my national television employers have been CNN, ESPN, MSNBC, and Fox and Current if you want to count that. The Current doesn't exist anymore.

So that's not possible. Four television networks that I've had some success at, and I've gone back to work a second and in one case a third time with three of them. So I went back to mss NBC, I went back to See and and I went back to ESPN. And it wasn't me going can I please come back? It was a mutual decision. So there is in all the sort of wander lust quality to it, and it's not very usual that you go back to a former employer, especially when you have a reputation of burning down bridges.

It's like, that's just that's just for show, so that when you leave someone it's like, so I didn't like that girlfriend anyway. It's the business equivalent of that. Ap happens when the power and potential of every employee and leader in your workforce is released, and corn Ferry can get you there by aligning your people to your strategy, attracting, developing, engaging,

and rewarding them to reach new heights. With corn Ferry, you get a partner who truly understands people, leadership, and the new landscape of work, a partner who knows how to take your business up. Learn more at corn Ferry dot com slash up. Do you ever think back on the different places that you've worked and wish they try to remember them? Right? Okay? Do you ever have any

any regrets? Sir? Wish that maybe absolutely. My going back to work for ESPN the second time was instibly to change the ending of that experience because I did not think I had behaved particularly maturely, and I thought looking and particularly reading about how it was, seeing twenty years later that there needed to be a different ending to it.

I think I succeeded accomplishing that. I would never go back and say that the opinions that I took my stances on were wrong, but there was absolutely no reason for me to have done certain things about them, like in a couple of cases going public. Certainly, you know, the twelve thirteen page memos that I would slip under my boss's door before going home at midnight probably were unnecessary. And they look at this thing and I I, oh, we hate this guy. This is really well written. It's just

it's a mixed message. I could have just had a conversation, and that was largely why I went back there, and other cases where you sit there and you learn from it. If you don't learn from something constantly, I mean, there are mistakes I made in at at ESPN the second time that I learned from And I was, you know, fifty six years old when I was when that show ended, um, and there were mistakes that they made to which they

may or may not have learned from. See, I'm still doing it so as someone I'm younger, younger than both of you, and if I want to learn something from you, and you know, you're talking about doing what you believe in and sticking to your conscience, but now you're saying that there are also things that you shouldn't have done. You could have acted more mature. So what advice would

you give? Never put it on paper? I mean, that's a good that that sounds like either paranoia or a cliche, but it's there's a permanence to it that you may not be intending as you write it. And this also goes for texts and emails and just use paper generically. You may not want it to be preserved forever in a large main frame under the Kremlin. I mean, you don't know where that's going to be. And I always as the longer I got into it, the more computer

materials came in. More I began to think, is it a good idea? And I would type all these memos on my home computer and just print them out. But even then it's something that you would say and you go, no, that's not exactly what I meant, and it's gone and there's no reason to That's the easiest one. It's just don't just sit down and say, here are my reservations and if you if you read from note cards or you read from what it is that you had written

in anger. And the other one is always if you can wait till tomorrow to do it, wait till tomorrow to do it. Those are the two simplest things and the only other general advice in terms of succeeding that there's two things I always heard. One of them is becoming less and less important. But the first one is if you want to go and be involved in media in some way, you have to be able to do everything.

If you have to be able to be in print, you have to be able to be on the spoken form in one way or the other, podcast, radio, internet, whatever. And you have to be able to be on video on camera in some way and be able to at least press the button to record the video. You must do all these things, and you know that's that's it's if there's another dimension that we haven't thought of yet, learn how to do that too. Snatch up. Yeah. Absolutely.

Another question I have was that despite all of the turmoil that you've had another at some of your jobs, are you happy with your career? Yes, Oh, I I achieved everything I intended to achieve at least fifteen years ago, possibly longer, everything that I had set out, and I literally other kids had day dreams of, I don't know what, being Donald Trump or something. I know what the average day dream was for a kid of my age in

the seventies. But I actually thought, maybe be great. What if there was an all news television station and an all sports television station, and I'd like to work for

them both. And I'd like to be involved in the baseball broadcasts, and I'd like to cover the Super Bowl, and I'd like to if it's plausible, I'd like to get involved in the presidential inauguration press well by by by two thousand and nine, I had hosted all of these things, including a World Series between the two New York teams, which is by itself, I hope I've lived

to see that. I was literally standing on the field at Yankee Stadium introducing Game one of the World Series when it suddenly dawned on me that if I did not stop talking, they would not get to play. I was to introduce the p A announcer Bob Shepherd, wh would then introduce the players. If I just kept talking, I was holding up this World Series was a great powerful moment as long as you understand you have to relinquish that fanciful power immediately. So I got everything done.

So yes, absolutely no question of it. When you start a new job, do you start it in a particular way. I'm asking this. I'm thinking in my position, which is sort of very mid level. I come into a new job, I kind of lay low for a little yeah, yes, and then I sort of figure out what's what an hour or two? Yes, okay, before breaking any heads. Yes, now that would be there. That would be the assumption.

It's it's an organic part of the process. You can't know where everything is, you can't know who everybody is by name. You have to have help very often going where's the door in this room? I know there is one I came in, but you you will absolutely need to be guided around for a long period of time. And that's a good time to be a little less obstreperous, because otherwise they'll just leave you and they'll tell you that the studios over here, when in fact that's the

closet and you're you're late for the show. So yeah, there there is to some degree a sort of toning down you do have to go and correct people's impressions. The one thing, unfortunately about having a reputation, whether it's is the greatest person in the world or the worst, some large percentage will have a ridiculously wrong impression of you. When I went to work for Fox in I noticed when I would go through the hallways and say hi

to people, they looked surprised, and some of them. As I'd be coming down the hallway, you'd see two guys chatting and suddenly they'd stop talking to each other and put their heads down and just sort of walked past me. I was like, what the hell did I do? And I found out only at about six or eight weeks in that literally one of the very few true idiot bosses I ever had had put out a memo saying, do not talk nor look in the eyes of Keith

Olberman unless he has spoken to you. First, I was like, what, why We're I mean, lots of things you could accuse me of in a workplace, but not wanting to talk to the people I worked with. It was certainly not one of them. And this went on for six weeks to the point where I was getting paranoid, and so yeah, I mean, there's always an adjustment period, but but you have to go in and make sure people have a fairly good opinion of you before you start spending that

in any way. Yes, yeah, I imagine that's gotten even harder for you as as you have more of a reputation as your career has gone on. In one sense, in other words, the baggage will seem larger. But if you don't act like the baggage, that point gets across to the relief of the people that you're working with much faster. It's like he didn't hurt anybody on the first day. It's like, I'm not you know, it's not

that at all. That's that I never I never, never have been my reputation two colleagues or people who would be below me on the food chain. It's my employers that I've always treated that way, and I they would even say that, And that's I think that's part of the responsibility. You're supposed to punch up at the office and you spend many times it's been on in the in the behalf of people who did not have the

kind of freedom that I described to you before. I was like, you know, people who have three mortgages and they have to keep this job. And it's like, well, I don't care one way or the other. I'll just I'll stick my neck out. I don't care it grows back, it doesn't go back for everybody. One last question I have. Have you ever been scared that you wouldn't get another job again? Uh? The thought occurs every once in a while.

I do remember a time I was fired from a job and I was reinstated two days later, because the boss can't fire you just because you're twenty one and he's drunk. But in that initial period of time, it's like I've been fired from my first job, and I it doesn't pay a lot, and I need four five dollars from my studio apartment at fifty fifth and Second, and I'm going to have to go sell blood. Now that's nineteen eighty. I don't think I've really had that

feeling since then. And one of the more interesting things is every time the industry evolves into something else, mutates. I think it's probably a better word. There's a certain group of people who are grandfathered in, and now that I'm old enough to be a grandfather, it's literally true that, as say the studio sports news show deflates into something

people don't need on cable. There are a few people who are who they'll still watch Bob Costas, Tony Kornheiser me while I'm I'm on I got under that wire. I'm somehow in the Yeah, okay, I remember him from my childhood or my father's childhood or whatever. I mean. I literally it's like I used to watch you with press. Secretary of the United States or the White House said to me the other day that he used to watch me on doing sports when he he was a kid.

It's like, oh, for God's sake, so so yes, and no you have anybody in a performing position whatsoever is always worried about that. But on the other hand, it seems like I've I've sneaked into some sort of permanent stature where people at least will tune in to laugh, even if I don't want them to laugh at that particular moment. So yeah, that seems like a nice luxury that you've built. That built it up. Well, thank you so much for talking to us about your career. This

was really interesting for me and for me glad. I hope so and I hope that any if anybody's still listening, I hope it was interesting for that. So there you have at Folks News you can use from a multimillionaire, legendary television and radio broadcaster. That being said, I do think that there were some lessons to be taken from that conversation that actually do apply to anybody in the workplace. Yeah.

I felt a little inspired. Yeah, no, I'm I'm ready to go out there and you know, start kicking ass and taking names. Yeah, I mean not being in it for yourself a little bit. Seems like a good lesson that started running their career could use. Stally true to yourself, follow your dreams. That's the Keith Overmon way. He thought he reached his dreams like twenty years ago. We should all be so by the way I did them. Half then and I realized that he reached his dreams younger

than I am. Now we're failures. Although maybe this is my dream. Yeah, come on, well if you put it that way, all right, And now it's time for our favorite part of the show. Half big takes, half fake takes. Have big takes are are not fully formed opinions about the world at work and not So what's your sam mine has to do with the business lunch, and it also has to do with what to order at the

business lunch. The trick here is you want to pick a dish that is easy to eat, and that generally means food on fork, fork in mouth, clean, release, repeat. So the brisket sandwich with extra jo does not fit into this description. What does fit into this description? Two words chopped salad. Okay, I get that. I get it. It's like a first date. It is like a first date and you have to look good, but we're gonna get the ribs. But it's being paid for by your work.

So like if there's a lobster roll on that many lobster salad, I do love lobsters. There you go. I'm not saying you've got a cheap out here. You could do the steak salad with prime rib on top, but you have to get something that's been cut up for you and that you can just kind of poke out almost like you don't even have to look down. You just know you're gonna get like manageable amounts of food in your mouth. All right, Okay, okay, My half fake take is that I think it's okay to use your

phone during meetings. That is such a super troll. Well, that's kind of the point it takes, you know, to get people riled. You know, meetings take up a lot of time. Everybody knows that they're too long. They waste a lot of time. I think that I can be engaged in the meeting and also sometimes check my email because you're meeting stinks. I will always be offended at you if and when you do that. Is this a

generational thing? I don't think it is. Like, you know, all my friends have their phones out during dinner, so I'm used to it. Nah, that ain't right. That's not right at all. Well, maybe your meetings should be better. I don't have meetings. Let me tell you right now, so I don't look at me. Well, that would be nice, but I gotta tell you I will meet you halfway, which is to say, a discreet under the table kind of check, yeah, just to see what's up. I understand

that I have an Apple Watch. Oh okay, that makes you better than the rest of us. I'm actually but I mean yeah, that's actually one of the benefits of it. In a meeting, you can just kind of be like, what's up? Okay, Okay, so the solution everyone gets Apple watches. I don't want to talk about my Apple Watch. That's weird, all right. I will compromise with you. I think that discreet almost under the table, like at least make the effort to try and hide it. Be cool about it. Yes,

I'm obviously cool about it. There are some people that who will basically just like put the phone out at the middle of the table, like lean on the table, and that to me is just that's not that's like your time is not worth my time, right, But that's kind of what I'm saying, though, Do me the courtesy at least of trying to look like you know it's wrong. All right, This has been half big takes halfa takes. Thanks for listening to another episode of Game Plan. You

can find me on Twitter. I'm at RZ Greenfield and you should check out Keith Olberman's new web series The Closer over at g Q, and I'm Sam Grobart. You can find me on Twitter at Sam Grobart. See you next week. Get the most from your people and send your busines a soaring with Corn Ferry from executive search to talent strategy, leadership development, rewards and succession planning. Corn Ferry knows Up is more than a direction, it's your future. Learn more at corn Ferry dot com. Slash up give

me AFT two. You're not feeling well, but worry on to give the hill. It's gonna make you go from healthy to ll ha ha. You're really good at that. Thank you,