Keith Olbermann, Trump, and the Life of the Professional Speaker
31 Dec 2025 · 29 min
TJ Walker’s podcast episode (Oct 25, 2016) discusses media personalities and the life of a professional speaker. Walker analyzes Keith Olbermann’s move to short-form online video (GQ), contrasts comedic political commentary with straight analysis, critiques Donald Trump’s Al Smith Dinner performance briefly, and answers a listener question about balancing a speaking career with parenting by recommending niching as a subject-matter expert, building multiple revenue streams, and using a home studio to preserve family time.
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Speaking with TJ Walker, the show where we dissect how and what world class leaders communicate. Today on Speaking with TJ Walker, I'll be looking at a lot of top news stories, the messages and the messengers behind them. Plus taking your questions. We'll be looking at what Keith Olbermann, formerly of MSNBC and CNN and ESPN and every other network is up to these days. An analysis of the Al Smith dinner benefit speeches last week, also the latest on the presidential campaign and more and more questions. But first, let's go to look at Keith Olbermann. Some of you love Keith Olbermann, some of you hate Keith Olbermann, and some of you may feel both. But he was a widely, widely viewed, perhaps the most viewed host on MSNBC. Although in fairness to Bill O'Reilly and Fox, the ratings were never anything to really cause any source of concern for the folks over at Fox. Bill O'Reilly always beat him. But Keith Olbermann has famously sort of burnt out, burned bridges. He left MSNBC in a huff, went to Current tv, sort of left there in a huff or gotten rid of. He was so difficult, that whole network went kapuhi. But apparently he got such a big payout, he's now so we're talking tens of millions of dollars. He now feels like he can do anything he wants. And good for him. He's recently started doing essentially video blogs on GQ Gentleman's Quarterly. Not something you normally think of as a preeminent outpost of political commentary, but they were looking for something to kind of jumpstart their website and the traffic there. They made a deal with Keith Olbermann. I don't know what they're paying him, if anything, or if he even cares. Huge profile of him in the New York Times the last few days talking about this. And here's the thing. I've seen a couple of his clips on gq. Very simple looking set. It's really just him talking and reading from a teleprompter and it has generated tens and tens of millions of views and that's without any advertising, not much promotion. He claims nothing other than his own tweeting. It does show that there is an interest in insightful political commentary. And here's the thing that interests me. It's not about the comedy. Now, you may find that Keith Olbermann occasionally has some wit about him, but by his own admission, he's not trying to be Bill Maher or Jay Leno or Samantha Bee or John Oliver. I mean, there's a lot of liberal political commentators who are comedians and humorists, and their comedy is what draws the audience in. That's not the case with Keith Olbermann. Now, there are a lot of commentators on the right, whether it is the far, far, far right, alternative right, the Alex Joneses of the world, the mainstream right, like Rush Limbaugh. But there are many commentators in audio and video format on the right who attract huge audiences, really not so much on the Democratic liberal side. And I am speaking of commentary and news analysis, not delivering news. And Keith Olbermann in that regard is really a lot more like the conservatives in that he's giving his analysis, he's not delivering news, he's not breaking news. He's giving perspective, analysis and commentary, and he's generating huge, huge audiences. Now, Oberman famously cannot get along with people, cannot get along with managers. By all accounts, GQ is just sort of letting him be. They've, I guess, set up a studio for him and they let him come in a couple times a week, shoot a few, and he leaves, and this may be a winning match. What I still don't understand because, folks, I predicted this several years ago. What I said at the time was, why doesn't Keith Olbermann just set up his own little studio in his apartment, do his own thing, not worry about any managers, not worry about any bosses, just do it himself, monetize it himself. And this is sort of one step up from that. I guess there's a teleprompter studio, sort of one person there to run the camera. But if you look at what he's done so far, and folks, go to GQ.com and check it out yourself, plus just go to YouTube and type in Keith Olbermann and you can see what I'm talking about. I do think this is the future. Now, I have a bit of a self interest in this because I started doing political commentary, not just communications commentary, political news commentary in a video format way back in the late 1990s. Now, that was too soon. People had a hard time downloading and watching a video commentary. But I have a strong interest in the medium. And I think at some point Keith Olbermann is going to say, what do I need GQ for? I'll just do it myself, sell my own ads, have no boss, no manager, no nothing. Just unfiltered Keith to the public. Is that going to appeal to most people? No, but it certainly could appeal to millions. Ultimately, I think that's where he's at it. Keith Olbermann is a talent. And I say that in the same breath that I say Rush Limbaugh is a talent. Rush seems to be a little better at getting along with bosses than Olbermann does. But they're both great communicators. And I for one, am looking forward to hearing more from and I do still listen to Rush occasionally, but I also look forward to hearing from Keith Olbermann occasionally. Okay. We spoke about humor. Humor is something that is valuable not just to political commentators, but to politicians. Ronald Reagan was the master of humor. He was always great at the annual Gridiron Club meetings and dinners in Washington, the annual press gala events where politicians are invited and they make gentle fun of each other and they make fun of themselves. Ronald Reagan was the master of that. Truth be told, Bill Clinton's pretty good at it. George W. Bush, not bad at it. Obama's pretty good at it. And that leads us to last Thursday night's event, the annual Al Smith Dinner. It's the Catholic Charities event. It's an annual event, but it gets big play every four years because the Republican and the Democratic nominees always show up and they sit next to each other, separated only by the cardinal. Now, it happened this year. Donald Trump's speech did not go over well. He didn't have, let's say, the best of jokes and he was booed. He was told to shut up. He was told he was an embarrassment and his jokes went over like a lead balloon. The problem with Donald Trump is there's a lot of problems. He can't seem to make fun of himself. The only joke that even was close to making fun of himself is when he said, I don't understand why Michelle Obama gets such great reviews for her speech. Melania gave this same speech and she didn't get good reviews. That brought a big chuckle throughout the House. But even there, he wasn't making fun of himself. He was making fun of his wife. And here's a guy who has famously said he apologized and then in the last debate said he didn't apologize to his wife for his whole on the bus grabbing, you know what, comments. Now Hillary Clinton, let's be fair. Now, Hillary Clinton's speech was not particularly well received. But compared to how blunt Donald Trump was, how sort of obtuse his attacks were on Hillary, nobody really noticed Hillary's speech and the fact that her jokes weren't that great. So folks, a little advice to politicians. These so called speeches, events, dinners that aren't important and they don't really matter, they do matter when it comes to the public forming opinions of you at A human level. Do they like you or not? It definitely has an impact on the media's opinions of you. You can of course make the case that someone could be a great public official, govern from the standpoint of what's in the best interest of the public at all times and not be funny. And on the other hand, you can make the case that someone can be wildly funny, have a great sense of humor, and constantly make decisions that are against the public good. I get that. I'm not saying it's fair, but I am saying it is reality. So if you are a politician, you don't have to become a world class comedian, you don't have to go to stand up comedy school. But I do think, you know, a stand up comedy workshop, an improv workshop here and there occasionally wouldn't hurt. Making sure somebody on your staff, someone on your speechwriting crew has a passing interest in stand up comedy. Probably a good thing. Folks, this program is brought to you by Media Training Worldwide for all of your public speaking media training needs. We're here for you. If you would like to get a taste without any risk, you can do so. We're happy to send you at no cost, no obligation, you don't have to give a credit card. But if you got an upcoming speech or media interview or podcast and you want to prepare, we'll send you our online media training course and an online public speaking course, plus a couple of books at absolutely no charge. All you have to do is click on the link in the show notes or just go to mediatrainingworldwide.com and click on the link for the free online training and and you can start learning today. So please use that resource, folks. We'd like to hear from you any way that's convenient to you. So you can post a tweet jwalker on Twitter, you can post a comment on our Facebook page, LinkedIn, YouTube. Wherever you are experiencing this program, you can post your comments, your questions or your suggestions for guests. I did get an interesting question from one of my online students earlier today and I want to share that with you and give you a question in more detail. So this one comes from Lee and he says, C.J. i just want to know if the speaking life is conducive to being a good parent. Can you balance both effectively? Well, of course you can do it effectively. You can balance anything if you have it the right way. But there's a lot of assumptions in this question of Lee's that I want to address. It's certainly possible and I've seen this. Some of my friends who are professional speakers, they get so addicted to the thrill of the stage, and they get better and better and more in demand. Next thing you know, they're trying to do 200 speaking engagements a year. They're on the road 320 days a year. And yeah, they might be making a lot of money, but if you only see your spouse and your kids one day a month, well, guess what? They're going to be strangers. It doesn't lend itself to lasting relationships. And that's why I have a lot of friends who are professional speakers who've been divorced three times and are now single and barely know their kids. So it's certainly possible, Lee, to be a professional speaker and be on the speaking life and have a horrible personal life and be a horrible parent. Now, I am a parent. I happen to think I'm a great parent. Now you can ask my daughter, maybe in a few years. She's three and a half at this point. She thinks I'm a great daddy. I can tell you that in the future. Can I guarantee. Well, no, I don't think anyone can really guarantee things like that. But here's the thing. It's about time. There are a few mistakes that some people do make that just guarantee failure. Some people, Lee, and I don't know what your particular niche is, but some people just say, I want to be a speaker. All I care about is speaking. I'll speak anywhere, anytime, any price. And they just sort of hold out. They put out a shingle saying, I'm a motivational speaker. They don't have any really clearly defined niche, no real expertise, and they just hold their. Put out a shingle as a professional speaker, keynote speaker, and they'll speak for a thousand bucks, 750 bucks. And you know what? You can do 100 days a year, and then with travel, that's 200 days, and with planning, that's 250. And that's pretty much your whole life. So, yeah, you've done a hundred speeches all over the country or different places, and you brought in 100,000. And to a lot of people, well, that sounds great. The average family in America's income is 55,000. So 100,000 sounds great. But here's the problem. You have expenses. You have marketing expenses. You have. And I'm assuming you're getting your travel paid separately, you have marketing expenses. It's your own business. You have to pay for your own health insurance. You have to pay for your own retirement. So what sounds like a nice, cushy six figure income is actually more like making $45,000 as an assistant manager at a Burger King. Well now if you do have a spouse and kids, there may be constant financial woes and problems combined or magnified by the fact that you're gone all the time. So that is a prescription for disaster if you try to be this general speaker. My advice, Lee, is it's fine to want to speak and it's fine to be a professional speaker, but you should never, ever, ever position yourself or see yourself in your own eyes as a professional speaker. That's going about it the wrong way. You need to position yourself first and foremost as an expert in a particular area. And because you're an expert, you will gladly speak on that. For a set fee, you will do workshops, seminars. For a set fee, you'll write books on the subject. You'll create online courses, you will do consulting. You will help people through a live Skype video. Once you define your area of expertise, there are now a lot of different ways you can make money on it. And once you establish an area of expertise, you can dig deep, deeper and deeper and deeper so that you get better at it and so that people recognize your expertise and you can charge more. That's really the key to it, I think. I have a good family life and I get to spend a tremendous amount of time with my daughter because I do have a home office. Now there are times when I'm on the road or I'm away in Europe for nine days or in the Middle east or in India somewhere, but I might have a three week stretch where I don't have to leave the home. I do have a home office. I have a home TV studio, recording studio, and I have a separate home office for everything else. Marketing, website calls, sales, all of that, and then a living space. And what that means is I often spend three meals a day with my daughter. Breakfast, lunch, lunch, dinner. This afternoon I was lucky enough to take off 3:30 and we went to a little farm and did the whole Halloween pumpkin patch thing. And now I am back in the studio at five doing a show for you so you can have flexibility. Lee. The hard part for most people is really figuring out what's the area of expertise you want to dig deep into and figuring out what your main driver is that you can sell. Now I also wrote back to Lee saying it can be conducive to being a good parent because if you are an expert and a professional speaker these days and you don't have a large Staff and office and you don't need to, and you don't have some big large consulting firm, you can have a home office, you can work from home. And Lee wrote back and said, wow, that would be great. I'd love to work from home. Here's the thing, Lee, be very, very careful of anyone selling you on the idea of helping you have a home based business or professional speaking business. Be very leery of that. I've met at this point thousands of professional speakers, many of them with home offices. I've never met anyone who started off because they started looking for a home based business. Your focus first and foremost has to be on some subject matter. For me, I've always been fascinated with communicating media speaking, speaking to the media, speaking to live audiences, politicians speaking, newsmakers speaking. It's just naturally been an interest of mine my whole life. So for me to talk about it, read about it, think about it, analyze this, it comes second nature. So when I started selling my services, it wasn't a big stretch because it was a culmination of everything I've done before. And you know, I didn't start off selling with the fees I do today. I mean, I started off selling my services at the bottom end. A thousand dollars a day, sometimes even less, Many, many years, you know, decades ago. Now I sell for a lot more. And I don't mind telling you, if any of you want to write to me, I'll certainly tell you what my fees are. But I won't broadcast it here in the pod, although I may in the future. It's not a big secret, but let's put it this way, it's. It's enough that in theory, if I only got booked once in a month for a day, that's more than most people make in a month. And it's enough for my own nut. Again, I don't say that to brag. That just means I'm a professional level speaker trainer. So, Lee, my advice to you is don't focus on home based business. Don't focus on being a professional speaker. Focus on becoming the number one expert in the world on some subject matter and make sure it's a subject matter people care about. Now, you could be the number one expert in the world on how to tie a Windsor knot or how to tie a bow tie. And I'm sure there's some ways of making money on that. And certainly you could have websites and videos that you monetize, but for the life of me, I've never heard of a convention hiring a speaker to talk about how to tie a bow tie or a Windsor knot. So I don't think that is a big enough niche, but I could be wrong. Don't listen to me. Listen to the marketplace. So my advice to anyone who wants to be a professional speaker is before you start worrying about your lifestyle and, you know, worried about being on the road too much, you got to worry about anyone hiring you even wants. And then you got to figure out a way of duplicating it. One of the biggest scams out there, all these get rich quick guys. And it is, for the most part, guys telling you how to become a professional speaker and how to be rich. And it's highest paid professional. Well, let me tell you, professional speaking is not one of the highest professions in the world. It's one of the lowest professions in the world. If you actually look at the reported revenues from people who are members of the National Speakers Association. I know when I first joined 10, 15 years ago, the average was something like $28,000 a year. Again, we're talking about less than what the association assistant manager at Burger King makes now. I think it's maybe up to 45, $48,000. So we're not talking about the highest paid profession. Of course, it is true that there are certain celebrities. If you are Bill Clinton or George W. Bush, yes, for one hour you can get two, three, four, even $500,000. But they're not being paid to speak, they're being paid to show up because they are a world renowned celebrity. And people like being around famous people. So it begs the question, how do you become famous? If you become president, obviously, problem solved. Bingo. For the rest of your life. You can make a lot of money as a speaker, but if you become president of the United States, money is probably, at least in the last 60 years, the least of your concerns. There's so many other ways of making money. But Lee, for you, for me, for most people, it's a chicken egg scenario. Okay. How do you become famous? Well, you speak a lot. Well, how do you speak a lot? Well, you become famous. So you've got to start somewhere. You've got to define yourself. And most people make the mistake of being too generic, too general, and they just call themselves a speaker or a motivational speaker. Too general, too vague, too fuzzy. Let me tell you a story about how I started. I don't talk about this often, but I don't mind sharing it with you. It's nothing negative. When I really, really started my training business as a serious business and not just something as a freelance side gig. It was about 16, 17 years ago. I had done training on the side for many years, but I was always hosting talk shows full time, working for members of Congress, working politically. I was doing other things. And when I started my business, it was the middle of a recession. And I looked at what all of my competitors were doing and they all said, we do media training for every people, every, every industry, every type of person in every industry. We do athletics and finance and authors and experts. And I'd had a little bit of experience in all those places, but I thought to myself, how can I differentiate myself? How can I somehow stand out as a little bit different? And how can I stand out as the best at something? So I looked at all of my clients and I had done a little dabbling here and there of some politicians, a few athletes, a few authors, an obscure Osmond brother here and there. You know, this is 20 years ago. And I looked at what I did and I said, you know what? I have done training with CEOs and CFOs at publicly traded companies, companies. And I also thought, who are the best clients to have who? And I wasn't even charging that much at the time, but clients who don't complain about paying money for training, clients who don't want to dicker over fees. And even then it occurred to me that the best clients were publicly traded corporations because. Because 99% plus of companies in the world are too small to be publicly traded companies or they're just privately held companies. So the idea came to me of why don't I call myself the leading media training firm in the world specializing in senior executives at publicly traded corporations. Now that may sound like a mouthful, but that's how I labeled my website at the time. It was T.J. walker Communications. That's how I positioned myself. And I gotta tell you, it started gaining traction in the second year when I went over to that branding. And it really seemed to work because I was instantly able to make myself seem like a good fit for people at publicly traded company. Now, I want to point out I didn't lie. It's not. Not like I'd never worked for a publicly traded corporation before or top executives. I didn't lie and fake it till I made it. I just narrowed my focus and I narrowed what I wanted other people to look at when they saw me for the first time. And I do think that that's a helpful technique. Whether you're a consultant, a trainer or a speaker, people have a hard time Seeing you with more than one hat and if you can narrow it down so they see you as one thing, it's going to make it easier for them to imagine hiring you, especially if you want to charge a lot of money. And that's what I did. Now I no longer do that because I found I had other ways of marketing. So now anytime someone calls me and they say they're in a particular industry, I just instantly start bombarding them with clients in their industry that I've worked for. And I create a personalized video for them where I talk about them, their concerns, their needs, other clients in their industry. I've worked with their issues so I'm able to personalize it in a different way. So Lee, that is my advice to you is figure out a way of really number one, narrowing your focus but number two narrowing the focus focus of your prospects so that they really see you in a different specialized light. Do that and you'll have a lot of flexibility because the more specialized you are, the more you can charge. The more you can charge, the less likely you are going to be to run around, fly all the way across the country for a low paying gig. You want to be turning down most of your prospects because they can't afford you long run or you want to be able to sell them on videos, online courses, things that don't take your time that you can do while you are home, spending time with your family. Good luck with your career and good luck with your family. You really can have it both. I'm TJ Walker, thanks for joining me. See you tomorrow. Thanks for listening to speaking with T.J. walker.
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