Close this search box.

Podcast Transcript – Rick Wilson

Rick Wilson

Rick Wilson – Wit trumps Trump


– I always believe you should mock authoritarians, you should mock dictators, you should mock these hyper populist guys because they’re so delicate. Underneath all of them is the wounded little boy who didn’t get laid till he was in his, out of college, yet these guys are all, they’re all of a type. Nope, I don’t care if they control vast armies, they still have this shitty fragility about them, and humour is their kryptonite. They hate it.

– Welcome to the “Humourology Podcast” with me, Paul Boross and my glittering lineup of guests from the worlds of business, sport, politics and entertainment who are going to share their wisdom and their use of humour with you. Humourology is the study of how humour can dramatically improve your business and your life. Humourology puts the fun into business fundamentals, increases the value of your laughing stock and puts a punchline back into your bottom line. Please remember to like, subscribe and leave a review wherever you get your podcast. My guest on this edition of the “Humourology Podcast” is a 30-year veteran of U.S. politics as a strategist, commentator and satirist. He’s constantly called on for sharp-edged and witty political insight on the national news networks, including CNN and MSNBC. He’s also a frequent guest on “Real Time With Bill Maher”. As one of the founders of the Lincoln Project, a political action committee of present and former Republicans to prevent the reelection of Donald Trump, he effectively used humour to prick the bubble of pomposity. His book, “Everything Trump Touches Dies” was hailed by The Guardian saying, “It gives more unvarnished truths “about Donald Trump than anyone else “in the American political establishment has offered.” His biography describes his run of the mill hobbies as hunting, fishing, flying, and overthrowing governments. Rick Wilson, welcome to the “Humourology Podcast.”

– Thank you, Paul. Great to be with you.

– Oh, it’s my pleasure. I’m a huge fan of your work and well done for getting it done.

– Well, thank you. It was one of those things that it was basically an existential choice about the country. Do we spend the rest of our lives in Gitmo or do we beat Donald Trump? And with all the things about saving the Republic and all the minor side benefits that come from it. So here we are.

– Tiny things like saving the republic.

– It’s the small stuff.

– How important do you think humour is now in political strategy?

– Well, look, it depends on the race in some degree, but we’ve found especially with a candidate like Donald Trump who has this enormously well-developed sense of self regard and this enormously fragile ego, that by poking at that ego, by poking at it with humour, we did something no one else would do. Because, look, other people who criticise Trump would say his language is inappropriate and he’s a terrible person, and he’s mean to women. And yes, we did all those things, but I also made the first dick joke about a president in a TV ad in the history of American politics. And we also hit him over and over again on this fragile self conception. He’s a man who wears makeup and weighs nearly 300 pounds and wears lifts in his shoes to seem taller and is notoriously delicate when it comes to the slightest criticism. And so ramping up all those attacks, it wouldn’t do just to say, “Donald Trump is old and impotent,” we had to make it funny, we had to make it cutting. And by doing that, the Lincoln Project set out with a very serious political purpose in three areas. We wanted to psychologically wage war on Donald Trump, which we did, and a lot of that was with humour. We wanted to move soft Republican voters away from him which we did, but we wanted to block hard Republican voters from feeling comfortable about their vote, which we also did. But in that first column, the psychological warfare column, we went at Trump’s ego in a lot of different ways, we went at his administration in a lot of different ways. We managed to run an ad called “GOP Cribs” and we made it look like one of those “MTV Cribs” ads, and it was, it was so over the top and so hilarious. And the girl who did the voiceover, it’s so funny because in real life the voiceover talent has a perfectly lovely normal speaking voice, but she puts on this like, “Hey Donald.” And we wouldn’t normally run an ad like that but we knew he would pay attention when we did it. We knew he would lock in on it. And once we got him hooked into those things, making fun of him sent him around the corner. And it wasn’t just because we wanted to troll the guy, that was certainly part of it, we enjoy trolling as much as the next guys, right? But it was also because Donald Trump would see one of those ads and then he would spend a day or a day and a half going crazy in the White House. And we know this because, there’s been a lot of reporting about it now. We had people in the White House who were talking to us at the time in the campaign, and we knew that it drove him nuts. So, of course, if I know something drives Donald Trump nuts, I’m going to do more of it. And we kept that drum beat, that cadence constantly running including some ads that I think are unique in American political history. I mean, the Covita ad that we did, with the riff on Evita, when Donald Trump got COVID and came back to the White House, that ad came from the fact that Steve Schmidt and I were on the phone late at night, out in Park City and we’re talking back and forth and he said, “We should do something. “He’s like up on that balcony like Evita.” And I was like, “Wait, “wait, wait, wait, wait, wait.” And there was about an hour of us designing the ad back and forth, singing to each other, making up new lyrics to, “Don’t Cry For Me, Argentina”. And when it hit, we knew that people in the White House, because they had tried to make this glorious comeback, they released this propaganda film of Trump striding manfully across the White House lawn and looking tall and vigorous, and we just ripped it apart. We just tore it up. And that approach works with a guy like Trump. Now, I always believe you should mock authoritarians, you should mock dictators, you should mock these hyper populist guys because they’re so delicate. Underneath all of them is the wounded little boy who didn’t get laid till he was out of college. These guys are all, they’re all of a type. They never played team sports, they were always mama’s boys, and they have this fragility about them. No, I don’t care if they control vast armies, they still have this shitty fragility about them, and humour is their kryptonite. They hate it.

– Why do you think that he didn’t have the nous to actually get some writers in and some people around him who could fight back with humour because it seemed that he wanted to do it all himself. Was that just ego?

– Well, it’s two-fold. One, no one who’s actually funny wanted to work for Donald Trump.

– Ah.

– I mean, look, there is a sub genre in American comedy of Trumpians or MAGA political comedy. It is neither political nor comedy. It’s awful, and it’s all about these resentments that they have. But Trump also believes that he’s the master of television and that he sets the stage, the narrative, the themes, all these things, and we just, we weren’t going to play that game. Trump would come out and try to blow up the day and we would try to blow up the day in a different direction. And we frequently succeeded in that. And what a lot of people don’t understand is, again, we weren’t just trolling Donald Trump for trolling, we were trolling because when Joe Biden came out of the primary, his campaign was basically out of money, they were exhausted and disorganised. We were trying to buy Joe Biden days. We were trying to buy him time. So one thing you never get back in a campaign is time. And so we were trying to get Joe Biden into a position where he had, the strength and the resources to fight at the level he would have to, and he did. But, and we also knew that, we raised $90 million last year. $90 million is a drop in the presidential campaign bucket though. We ran the most successful super packs in history and all this other stuff, but we still couldn’t have gone up nationally and spent the money like Donald Trump did. So we had to be very targeted. We had to be very clever. We had to do things that had inherent humour and virality to them. And the virality could come from either being funny and witty and cutting and weird, or it could come from being emotionally resonant and powerful. I think it served us very well as an organisation and a movement to be able to talk about things that were lighter when we were also running ads about COVID and the economic devastation and the racial tensions and violence in the country. So, we could have gone heavy handed all the way home, but we really felt like, especially when it came to the narrative disruption ability and the psychological warfare against Trump, mocking him was more effective than saying, here’s a statistic and here’s another statistic and it sucks. And Donald Trump is to blame. You can do that, but he doesn’t care about those things. I mean,

– Do you think—

– You can wake Donald Trump up and say, “Hey, you’re going to be president again “but the earth is going to be consumed “in a firing nuclear apocalypse.” And he would say, “What’s the downside?” He didn’t hear about anything except himself.

– Well, you’ve just sort of said, he’s going to be president again. And a shiver went up my spine. What are the chances? Because you’ve had your foot in both camps. You’ve been a Republican, you’re now an independent. What do your Republican friends say about that possibility? And do you really think?

– They are simultaneously terrified and aroused. It’s like fucking your babysitter. It’s like a moment of complete… they can’t quite sort their emotions on it because, they loved the sugar high of Trump. They love not having responsibilities. They love not having to explain anything. They loved having somebody they could go, “That’s Trump, what are you going to do?” They loved that. Now that it’s on them, they’re in a much different position. They’re in a much more, they’re in a much more tenuous spot. They loved that though. And they loved the sort of middle finger to decency and probity and everything else. They enjoyed that freedom. But it’s a “Lord Of The Flies” kind of freedom. Okay? It is, it inevitably devolves into things that are shitty. And so, they fear that return and yet they love it. They also know that Donald Trump in the longterm and when I, when I started using the phrase, “everything Trump touches dies”, I meant it as a sort of witty little throwaway. I didn’t mean it as hundreds of thousands of Americans dying or anything like that. But as a political rule in this country, it’s an iron law now. I mean, I’m like the fucking Isaac Newton of Donald Trump laws, right? Principa Dickheadea. And so this guy, they think, “Okay, Trump let us be free. “He let us turn up this white male base. “And we were able to do, “anything we wanted.” The difficulty for them is he repulses and repels every other voter demographic group over time. And the Democrats, God bless them, they are, as I like to say, holistically terrible at politics. They’re good at little slices of politics, they’re extraordinary at some things. They suck at understanding the big complex multi-variate problem. The return of Trump would be the ultimate multi-variate problem for the Democrats. They would not know how to handle it. And right now they don’t understand how much trouble they’re really in. They have a majority in the House and Senate, and they’re like, “Yay, it’s permanent.” No, it’s not. And they’ve got a five seat majority in the House and a tie ball game in the Senate. And so typically, in an off year election in America, the party out of power in the White House will pick up between 10 and 25 seats. So that’s a House majority. And Mitch McConnell has already raised about $50 million to kill off the democratic candidates in 2022. So, this idea that Trumpism died with his leaving office is crazy. These guys that are running now are more Trumpy. They’re more, they lack an even greater degree of self-referential ability and knowledge. They cannot, they can’t understand why, people don’t love the dear leader and it’s going to be something that I think is, they’re going to pay a price for it probably in 2022 by not taking Trumpism seriously.

– Gosh. Oh, well, that’s something to look forward to, isn’t it?

– I’m just full of good news today Paul.

– Well, let’s take a little deviation. What makes you laugh Rick?

– What makes me laugh? Bad people getting kicked in the nuts.

– Well, you must have been laughing a lot recently.

– I have a great deal, I take a great deal of pleasure from beautiful wordplay and a great deal of pleasure from… my humour, as the stuff I do is, fairly constructed, but it’s not really comedy, it’s more wit than comedy, I guess you would say. ‘Cause I grew up in a house of talkers and people who wrote and talked all the time and argued all the time. So, being quick and verbally fluent with something that can be cutting or witty amuses me. I like people who can do comedy that isn’t, or can do humour that isn’t just broad comedy. And of course I grew up, as a, was a weird kid reading, Mencken and Bierce and Saki, and a lot of, a lot of stuff that is a little bit bygone now. But, as I always say that the dubious benefits of a classical education sort of serve me well in terms of being able to wrangle the English language around a good bit. In America, there was a magazine in the 1970s called “National Lampoon”. It spun off the “Harvard Lampoon”. And so I grew up in the seventies reading that as a little kid, as a kid. And that sort of affected some of the wryness of, corporate humour that exists today in my, at least in the way I express things.

– So, I mean, it’s very, very verbal and witty and everything. So you’re, which goes against somebody getting kicked in the nuts, to be honest with you.

– Yeah, but I find, listen, I think, I love watching people who are extraordinarily pompous get their ass handed to them. I love watching them have that moment of realisation that they’re, that they’ve shit the bed and that things are going very, very wrong for them. And you get that in politics more than most other things. You rarely see it in corporate life because those things are much more constrained and carefully crafted. But in politics, you can tell sometimes when somebody, to use the southernism that my grandmother, who was a very colourful Southern belle, would say, they realise there is a turd in the punch bowl. And after there’s a turd in the punch bowl, it’s not punch anymore, honey. It’s just turd water. They realise that they’ve made a mistake. I, that is a moment that always pleases me like watching bad people, watching bad people realise that they’ve made an error. It’s a delight for me. And, again, I enjoy crafted and smart humour that can play out a little bit. I don’t mind a little foreplay in my humour.

– So are there any comics who you were, particularly were drawn to?

– I can’t say necessarily. I like more topical and observational, topical sort of comedy that is more of the moment. There was a group back in the, in the eighties when I was in school, when I was in college in Washington, D.C. called The Capitol Steps and they did a sort of like light, light comedic takes on the moment in D.C. at the time. I think we lack that kind of thing now because there is a certain degree of prissyness that’s crept into everything and a certain degree of, “Oh God, am I going to get cancelled if I make a dick joke? “Am I going to get cancelled if I use the wrong word?” And so, that sort of thing. I feel like a lot of comedians are very restrained now in that sort of stuff. They try to be on the edge about, I mean, how do you do edgy humour about a smartphone? You don’t.

– Yeah.

– You do edgy humour about the things that always matter to people. Money, sex, power, politics, religion. And none of those things can be approached in the same way anymore in a lot of ways because there are too many people in the world that their greatest joy is saying, “What you’ve said is inappropriate “and now you must leave society.”

– But do you not think that that was one of the reasons why Trump got a following was—

– Absolutely.

– Yeah.

– The transgressive nature of Trump is extraordinarily appealing. And for my friends in the left, and I told them this a lot, if you do not understand that there are people in your base who do believe that if someone makes the wrong joke, they must be removed from society, they must lose their job, they must lose their platform, they must go away, if you don’t understand that eventually voters make a choice, they will choose the sociopath over the scold. They will choose the nihilist asshole over the thought conformity police. I worked to defeat Donald Trump but it doesn’t mean I’m a progressive. I’m fundamentally about a conservative of the individual liberty strain. And I believe that individual liberty is the, is the highest goal of a system of governance. And, if you end up where there is such a social constraint on speech, you will get a pushback. You will get a response in return that is Newtonian in the equality of its response. And so one of the reasons that you will see people who follow Trump continue to engage in the performative sort of dickery that he was known for, is because they know it works. You know why Fox News is spending weeks and weeks and weeks talking about Dr. Seuss and cancel culture? Because they know that most Americans are not far left woke Progressives from Brookline, Massachusetts, or from San Francisco. They know most progressives aren’t terribly woke. The scold culture, see, the thing I love is powerful corrupt people getting taken down a peg. The thing they love is anyone who violates their cultural norms getting taken down completely. And that’s, I think that’s something that is a lifeline for the nationalist populist types like Trump.

– Yeah, I… Yeah, we just heard the birds fly by.

– You did. You heard a big red tailed hawk trying to get eels out of my pond.

– That’s a first for the Humourology Podcast.

– I live in the jungle. Yes, I do.

– Rick, is everyone funny? Do they have the capability to be funny, or is it instinctual?

– Paul, that is a great question. And I don’t think everybody’s funny. Not everybody can, I can’t sing. I can do a million things. I’m a polymath in a million different areas. I can’t sing a note. I sound like two cats fucking in a dumpster. It’s horrifying. But—

– I love that album by the way.

– It’s great on vinyl. People can be funny, but they’re not always humorous. I mean, the 400 pound woman walking around Walmart screaming at people without a mask on, she’s funny. She just doesn’t know why. But I think it takes, I think it takes at least a respect and engagement with the language to be humorous. And I, I’ve talked to a lot of, in part of my other work, I write a lot of speeches for corporate, Fortune 100 CEOs and things. And I always had this fight with them at first which is, stop talking like you think your lawyers want you to talk. Speak as you speak. Sometimes it’s going to be eloquent and beautiful and uplifting. And other times it’s going to be your dick down in the dirt. Okay? That is the genuine thing that people really are. Okay? I could play the role of the political strategist and speak in that sort of lofty blah-blah-blah tone all the time. That’s not me. And there is a great power to people who are authentically funny because they are, and people get that. People understand that. You always know people like that, that have some inner light about their take on the world or their ability to withstand stuff. And I quote my grandmother a lot because she really was this wild Southern character. I mean, completely crazy as could be. But, she would say, “Gallows humour son, is still humour.” So if you’re…, and that was one thing we had a lot of people ask us during the campaign, like, why don’t you take Trump seriously? Well, you’re making fun of him. Why aren’t you hitting him on this issue? Well, we do take him seriously. We did take him seriously. We took him out seriously, but we did not treat him lightly. We didn’t treat him as a non-entity. We thought we’ve got to go and use all the different tools in the toolbox. And I think people, when they’re communicating, underestimate the value of wit and humour and a little bit of self-deprecation.

– Yeah, I agree. Because, I mean, as a psychologist, I get brought in a lot because I’ve got a performance background in comedy and everything. So I get brought in to where you’re writing the speeches, I will be getting them and deliver them and everything. And one of the first things I have to do is stop them from trying to do a gag sometimes because they step all over it.

– God! I, that to me, the first time I went on Bill Maher, one of his producers said to me, he goes, “You didn’t write any jokes, did you?” I was like, “Of course not, I would never do that. “I’m not a comedian.” And he’s like, “That’s the right way to think about it.” Bill’s a comedian. He’s a guy who does that craft, at the top of the game like very few other people ever have. But I would never presume to be a comedian because I’m not a comedian. I can be witty, I can be funny, but I’m not, but I try, I know the difference and the distinction.

– But that’s very important for our listeners to take away as well, is knowing what to do. ‘Cause I think people sometimes go in and go, “I have to do a gag.” Well, actually comedy is more about listening. And then, hearing when it’s appropriate to do something.

– That’s right. I think that’s very spot on. The idea that you’re a CEO or a military leader or a business leader, or a civic person of some kind or a political figure that you lead off with a canned gag about, “Hey, I’m happy to be in Des Moines you pig fuckers,” or whatever. Some weird ass thing that they think is funny. It’s got about an 80% chance of going over like the proverbial turd in the punch bowl aspect, the aforementioned turd in the punch bowl, right? And so, all those things I think accrue to, if you have some authenticity and engagement with what’s really happening around you, you’re going to be funnier. You’re going to be more, you’re going to be more valuable and engaging than you will be otherwise.

– Yeah, and it’s in, it’s in the moment. When my first book, “The Pitching Bible”, the first chapter is called “It’s All About Them” because actually whenever you’re communicating, it is about them. And actually I would argue that Trump was actually quite good at recognising other people and what it was about. But he just didn’t—

– Yeah, in both the negative and the persuasive frames. I mean, he understood to say to his audience, he understood the demographic character of his audience. And he understood the valences by which they were moved politically. Alienation. Aggrievement.

– Yeah.

– A sense that other people had more than they did because they were educated not because they worked hard. There was a frank sense of racial animus built into Trump’s messaging to them. And how did he get, how did he convince those people that he was one of them? He was crude. He was crass. He insulted his opponents in ways that were outside the bounds of political discourse in American politics. The most striking thing about it is, yes, it was enormously persuasive to those people. The most striking thing about it was it was also a roadmap to all Trump’s own mental insecurities. It was also a roadmap. Because it’s Trump who pretends to be the billionaire. The hobo’s idea of a billionaire is Donald Trump incarnate. And so, the idea that he was their avatar of this hatred and hostility they felt for all these people that they thought were not like them, e.g. not white working class, rural voters and ex-urban voters, it was brilliantly crafted on his part. It was a great pitch on his part. And, they tried initially to do a high, low. They would have Jared Kushner and other people going into private meetings and saying, “It’s an act. “Don’t worry about it. It’s going to be fine. “He’s normal underneath. He’s a business guy. “He’s just pitching.” Well, he wasn’t normal underneath, of course. It was crazy town. And everybody eventually knew that there was no better iteration of Trump. There was no better version of Donald Trump. He was always going to be that guy.

– So what would the world be like without humour, Rick?

– Oh, God, it would be like the vision, apparently a lot of people that, on the cancel side of the equation would love. We would each day contemplate our sins and failings and cast ourselves into the abyss and rend our hair shirts and everything else. I mean. It’s a very sackcloth and ashes world without humour. And not frankly, one I don’t, I don’t really care for.

– Well, I mean, this is the Humourology Podcast and where we’re trying to go, how does humour improve your business and your life generally? And I think it’s tremendously important to actually understand the essence of what people’s humour is like. And without it, I think the world is lost, basically.

– Look, I mean, we go back and humour has been a part of recorded human history all the way back. I mean, there were fart jokes on Sumerian tablets. Okay? This is something that is inherent, I think to humanity. I think every culture has its variabilities in what they look at as humorous, but I think it is, I think it is inherent to us. I think it is something that humanity shares. It has a lot of variability to it, but, and without it you do become… I mean, when I started life out, when I was in college, I was a Soviet studies and philosophy major, which of course, suited me perfectly for what I do now. But one of the things I was doing a lot of for my senior work was looking at sort of Soviet dark humour and the sort of incipient movements in the, inside the Soviet union of how the anticommunist voices could never truly be silent. There was always some level of wit or humour trying to sneak through. And, you look at that as a very dark society in a lot of ways. A very shielded, controlled, constrained, surveilled society. And yet they were still making jokes about Khrushchev and about Brezhnev and about Andropov even. And even the ones they feared the most, there were jokes. And humour exists in every shitty circumstance. It is something humans need, and it also exists as a way to level the playing field between power and powerlessness, between entitlement and disenfranchisement. And I think it’s important we keep that sort of, that we’d be mindful of that.

– So, how important is it to be able to laugh at yourself? I mean, I’m talking for takeaways for people listening to—

– Sure.

– Because, we work a lot with CEOs and people and that level of pomposity where you can’t do that.

– Generally speaking in most Western countries now, our CEO culture is still sort of a relic of the fifties and sixties of the last century. This idea of the guy in the perfect suit and a perfectly tied tie and the French cuffs and the serious expression and, the long gaze into the future. That I think doesn’t work the way it used to. And I think people who do take themselves too seriously end up in a box where they can be easily caricatured or easily disrupted in a lot of ways. And the idea that you’re like, there’s a fascinating set of like trolling that a lot of people in the Trump world did. They were like, “Oh, well “you’re just jealous because you’re bald.” Okay. But, there’s a lot of weird, like physicality to that, to the CEO role that used to exist that doesn’t anymore, because what is a CEO anymore? Mark Zuckerberg wears crappy sneakers and sweatpants, and he’s worth more money than all of us by several orders of magnitude. And the sort of, this shift in corporate culture from the suit and tie world has had a concomitant loosening of how seriously you take yourself. And I think that’s probably a good thing.

– So you would really say that leadership is enhanced by the ability to laugh, yeah?

– Oh, look, leadership is enhanced by the ability to laugh, not only at yourself, but with and for, not necessarily at, but with and for your people and your organisation. Okay?

– Yeah.

– Because, managerial authority can stem from either love or fear. Now, fear-based organisations can work for a period of time. I mean…

– Yes.

– Warning. But, with your people are loyal and love you and care about the mission and the… My dogs are behind me. They, at least love me. See, hello.

– Timing.

– Timing. Yes. It’s everything. If you have a culture where… The Lincoln Project, we often call ourselves a pirate ship because we’re not constrained by a lot of the old rules. And we actually love the analogy of the pirate ship because we’re married. We’re generally having a hell of a good time. And, we are, there’s a lot of towel snapping inside the camp and nobody’s safe from anybody going at them because, and we’ve built that culture where I want, when I say to one of our, somebody who works for me, “Hey, go execute this.” They know they’re going to go execute it. I trust them to go execute on what they’re going to do because we hire smart people to do smart things. And I also know they’re not going to freak out if I say, “Return with a mountain of skulls.” Or something like that. They get it. And so the pirate ship analogy in part is because there’s some swashbuckling, there’s some happiness about it. There’s a word called berserkergang, which was the sort of Viking trance they got into in combat where they were just like, fuck it. And they went at it. And so, I think if you’ve got an organisation that are happy together and have fun together and are amused, and you know what, and nobody’s exempt. So we have this broadcast that we do called Lincoln Project Television. And one night I’m out, I’m on the set, I’m doing the show. And one of our guys from the political office, this kid Lucas comes walking past behind me wearing a full Abe Lincoln outfit. And they’re doing their very best to crack me up on TV. And I’m doing my very best not to crack up, but finally I looked and I was like, “For fucks sake!” But an organisation that can’t have any fun, that doesn’t have any sense of, of lightness, like I said, they function for a while but they fall apart very quickly.

– So if I actually asked you to make a formal business case for humour in office, what would you actually include in it?

– Well, look, I would say this. Humour is an expression of the authenticity of the character of your leadership. Because not every person is a rigid automaton. And being able to show humour is a way of connecting the people who work with and for you, and to connect with your clients and your customers with a genuine sense of who you are as a person and as a corporate culture. And that, that is an attraction that doesn’t exist. You can’t buy that with advertising. Okay? You can’t buy that in a corporate culture by going on rock climbing retreats. There’s a degree of which everybody’s sitting around the table going, “Fuck you.” And having a good time about it is a bonding, has a bonding value that you don’t get elsewhere. And look, there is a degree to when humour becomes something very pointed and ugly and corrosive, but that’s not humour. That’s verbal cruelty disguised as humour, okay? And that you do have to watch for that. You do have to, you have to monitor that because there are people who will abuse that kind of thing. But for the most part, again, I think, actual humour is a gauge of authenticity of the self. And anybody who wants to just be the most serious of serious people, go be an actuary. Go be an insurance adjuster or whatever. I’m sure there are funny insurance adjusters but there are a lot of people who, they see you as a real person when they know what makes you laugh.

– Yeah. And I mean, actually what we have to do and what you’re brilliant at is selling this to people. So what’s the return on investment so that the accountants can go, “Ah, yeah, that’s worth it.”

– Well, as Alex said, the accountant can fuck off if they don’t like it. But, now, look, the return investment is a corporate culture that is stronger and more resilient and more bonded. The return on investment on the external front is that you don’t take yourself too seriously. You don’t look at yourself, and look, there’s a spectrum, okay? On the one hand, you don’t want to be trying to be hokey corny funny. You don’t want to be Go Daddy, an American political advertising, okay? But neither do you want to be so stiff and rigid and boring and unengaging that clients, customers and your employees go, “My work’s okay. “But their product’s fine, but…” And look, not every product needs a joke about it. Not every person needs to be funny all the time but showing enough of it, it’s the hot sauce theory, okay? Any idiot can use too much hot sauce. It takes a genius to use the right amount. That idea of calibrating your, the way humour plays, I mean, that is something that if you do it right, I think you get a great corporate culture.

– Yeah. I couldn’t agree more. There’s a great study in America that said 70.9% of people will change supplier based on one statistic. And that is if the supplier is more fun.

– Yeah. Sure.

– I think fun is completely undervalued. People—

– Fun is very, yes, fun is a underappreciated, image asset in organisations And again, the pirate ship. When the Lincoln Project was fighting Trump, we weren’t just out every day saying, “If we don’t defeat him, “he will destroy democracy.” We were out, we have to get rid of this guy because he can’t walk down a ramp. He can’t drink water with one hand. We have to get rid of this guy because he’s a buffoon and a clown. And he’s humiliating you by pretending to be president. Yeah, it’s definitely a, it’s definitely an under appreciated asset.

– Oh, I couldn’t agree more. Have you ever, and I presume this is going to be true. Have you ever taken a joke too far and crossed the line?

– Oh, sure. One time on MSNBC, a lot of the alt-right in American politics really supported Trump, these Neo racist guys, the Neo fascists and Neo Nazi guys. And I was on Chris Hayes’s show. And I said, a lot of these alt-right guys are home in their mom’s basement masturbating to anime. That joke, probably could have not been on TV. The collective pin drop from that one was fairly excessive.

– I think you coined the phrase about Trump as a faecal Midas.

– Yes.

– Did you not? Yes. He’s a faecal Midas.

– That’s one of my favourites as well. I don’t think you crossed the line there, but—

– No, I don’t think that was, that wasn’t over the line. Masturbating to anime was a little far, I think.

– I love it. So, in business, is it survival of the fittest or survival of the funniest?

– Well, again, going back to that gallows humour thing, you don’t have to be unfunny to be fit.

– Yeah.

– In fact, you probably are more resilient if you can take and make a joke. You’re probably more resilient if you can find, if you can find a moment of humour in even the worst days. I mean, look, our organisations had a couple of rough weeks. We’ve had some stuff in our organisation that hasn’t been great, but we wake up every morning and it’s like, “All right, what’s on the goddamn horizon today? “What fresh hell is this?” And we get through it in part because our core team of people, we believe in each other, we believe in our mission, we believe in our cause. We also believe we’re not going to take ourselves too damn seriously every day. We’re not going to get up every morning, because if we did, the ridiculousness of some of the attacks against us would hurt.

– Well, I think it’s very important that, I mean, you talked about when things go wrong, surely that’s when humour makes you stronger as well. That resilience comes through a sense of humour. Does it not?

– I really truly believe that. And that idea that you can look at the worst moments and find something about them to mock or to contextualise it or to make it lighter, I think that’s a really strong character trait. If you can do that, you’re a stronger person. And if you don’t take yourself too seriously or believe so, try not to buy all of your own bullshit is a pretty good rule in everything in life. And if you can do that and you can come out of it with, again, with a balanced sense of humour… I’m a private pilot, one of my instrument flight instructors one day, we had a little problem in the plane and I said, “Okay, I’m running the checklist.” And I went through like A, B, C, D. And I said, “Do you want to take this over “if I can’t figure this out?” He goes, “Nah.” He goes, “By the time, if you can’t figure it out, “we’re going to be a greasy stains. “So you might as well get to it.” And I was like, “Okay.”

– No pressure.

– Yeah, no pressure. Engine stopped, but it’s okay. So, again, I think humour, that authenticity of being able to admit you’re in a bad space and while you’re taking it seriously, you’re not taking yourself overly seriously, it’s one of the things I think that is a matter that builds strength and flexibility and that resilience like you talking about into organisations. And people that aren’t that way and who can’t take anything, who can’t find humour in anything who don’t have a sense of joy even in the shitty moments, they are much less able to handle these things.

– Yeah, resilience again. Well, we’ve reached a part of the show, Rick, which is called quickfire questions. ♪ Quick fire questions. ♪ Who’s the funniest person in business or politics that you’ve ever met?

– Funniest person in politics I’ve ever met was a guy named Ray Harding. Ray was a Serbian refugee from the Holocaust who came to America. Went into the U.S. Army, became an American citizen, became Rudy Giuliani’s like chief political counsellor. But Ray had this unbelievable constant low dark patter about everything. And it was always like, just perfectly balanced and eviscerating pompous people in particular. Ray was one of the human beings I’ve ever met. Lavishly corrupt. He chain smoked Camel cigarettes back to back. He was enormous. Went, got in all kinds of legal trouble, a classic New York City character.

– Oh, well. Is he still with us or is he gone now?

– No, Ray’s passed.

– Oh, right. Shame. I would have loved to have met him. What book makes you laugh?

– What book makes me laugh? There’s a book called “Augustus Carp”. I’m struggling to remember the author at the moment. It’s a little, it’s this parody basically of Victorian manners that just kills me every time. And it’s just, it’s so spot on about the sort of, the do-gooder Victorianism. It is one of my favourite comic novels. It’s really, really brilliant.

– What film makes you laugh Rick?

– “Dirty Rotten Scoundrels”, every goddam time.

– Ah.

– It is just about the perfect comedy. It is so, so well-crafted. It is my favourite. It is my favourite comedy by an order of magnitude.

– Oh, Steve Martin in that film is just hilarious. It’s perfectly spot on. I love the scene at the dining room table when he goes, “May I go to the lavatory?”

– Right! Mother.

– I know and he just—

– Ruprecht do you want the genital cuff?

– That’s right. It is genius. He’s genius. And even, I mean, that’s how good it is that all we have to do is think about it and we start to laugh. That’s the perfect, in psychological terms, anchor for you. You just think about it and what a genius. And by the way, what a great, his autobiography, “Born Standing Up”.

– Yes.

– That’s a great book as well. What word makes you laugh?

– What word makes me laugh? Precious. I don’t know why. And I guess it’s because I was raised in the south. Because Southern women can use the word precious to mean everything from that’s beautiful to fuck you.

– Oh.

– And it always cracks me up. I don’t know why. When someone says, “Oh, that’s precious,” I just…

– Yeah. It’s a great word. I was thinking in “Lord Of The Rings”, my precious.

– Right.

– And now—

– My precious.

– Okay, shifting over to the other side, I know you’re a libertarian at heart, but what’s not funny? Is there anything that’s not funny?

– Look, I mean, there are things that are not funny in this world. Like genocide is not funny. Okay? Organised racial hatred is not funny. Now, the people that do those things are inherently funny ’cause they’re always the worst possible fuck-ups no matter where they are found in the world. I mean, I guarantee you, other than skin colour that there’s very little derivation between them about how broken they are as individuals and why they start doing those things. It just, it is, the universality of shittiness is something that, those kinds of things are not funny. They’re just not funny. But weirdly, a lot of things can be funny that you might think aren’t funny. I mean, some of my, one of my best friends survived cancer a few years ago and she’s just has this mortal sense of humour about it. And that got her through it. It was a compensation and coping mechanism that at first you’re like, “Okay,” but then you realise it’s like, that’s defiance. Comedy can… humour can be defiance. Well, just like the Soviets that we talked about earlier, that was defiance against authoritarianism. And in her case, that was defiance against the disease that was really trying hard to kill her. The idea that there are unfunny things in the world, yeah, there are plenty of unfunny things. Child molesters, not funny. Hanging child molesters by the neck until dead, more funny. But it’s like, I fear, I’m more afraid of a society that thinks that a lot of things are off limits for humour than a society that thinks only a few things are off limits for humour. It’s the old Voltaire thing. Let me know who you can mock and I’ll tell you who’s powerful.

– Yes.

– Was it Voltaire or Molière? I think it was Voltaire. But, all those, all those areas of our societies that we take very, very seriously, we also ought to look at it as, in a broader perspective. Occasionally, that seriousness is because we don’t want to look at it hard enough. And sometimes we don’t want to look at things because we think of everything is too existential and too black and white and too consequential. And, the other day somebody asked me about, they asked me about, my position on climate change. I was like, “Climate change is real. What about it?” And they’re like, “Well, you were a Republican. You oppose.” I’m like, “No, actually, “I believe that markets have power. “We should put them to work in dealing with climate change. “Also, I believe, unless you’re willing “to put a hydrogen bomb in a volcano and set it off “to help climate change, “you’re not really serious about it.” And this guy is just like, “Wait, what? “What, what?” Well, look, if volcanoes cool the earth, we might as well use them. And I, when I realised he did not have the ability to cognitively like connect that I was being funny, I dead panned it even further.

– Of course.

– And by the end of it, he finally like, something went finally like, “Oh wait, you’re joking about a hydrogen bomb in a volcano.” I’m like, “You think?” Not that it would.

– Would you rather be considered clever or funny?

– Clever.

– Really?

– Yeah.

– Because funny comes easy?

– Because clever is funny.

– Oh, yeah. That’s where I was going with this because I—

– Clever and smart are two different things. I know plenty of smart guys who aren’t funny.

– So clever is funny.

– I’m a relatively smart guy who is funny.

– Yeah. Well, no, no, but that’s really interesting because I think in order to be really funny, you have to be really clever.

– Yes. Yes. You do. Clever comes from a power of observation about what’s happening around you and the ability to integrate that information quickly into a schema, a worldview, if you will. And that lets you be funny. Quick on the uptake is the essential nature of humour in a lot of ways, of observational humour, particularly.

– Yeah. I completely agree. And finally, Rick, Desert Island Gags. If you could only take one joke with you to a desert island, what would that be?

– The last man on earth, sat alone in a room. There was a knock at the door.

– Yes. Nicely done.

– Philosophy jokes.

– Yeah. I wonder how many of our audience, that’s gone way over their heads. But that’s a good thing ’cause they’ll be thinking about it. And you’ve given us so much to think about, so much to laugh about. Rick Wilson, thank you so much.

– Thank you Paul. I love being with you guys.

– [Paul] The Humourology Podcast was hosted by Paul Boross and produced by Simon Banks. Music by Steve Haworth, creative direction by Les Hughes and additional research by Helen Sykes. Please remember to subscribe, like and leave a review wherever you get your podcasts. This has been a Big Sky production.

Listen & Subscribe where you enjoy your Podcasts

See also:

More Humourology highlights