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So to Speak Podcast Transcript: How to make a winning free speech argument

How to make a winning free speech argument

Note: This is an unedited rush transcript. Please check any quotations against the audio recording.

Bob Ewing: I wrote an essay years ago called “Sweet Prime Focus,” and the idea was, focusing is so important for communication, for being effective at anything. Now, meditation’s a really popular way to try to improve our focus. I think that that’s starting at step three though because –

Nico Perrino: Meditation is?

Bob Ewing: Yes. It’s really hard to focus if we haven’t swept and primed. Before any big event, I think it’s important to sweep and prime and then, you’re naturally ready to focus. Breathing techniques and vocal exercises, warming up our voice, warming up our bodies, warming up our lungs, warming up our brains and minds are ways to prime ourselves to be ready. No football player just gets off the couch, gets out of bed to watching TV –

Nico Perrino: Without doing some jumping jacks or some stretching.

Bob Ewing: Yeah, right? You get ready and then you get the pump-up to talk and you’re, “Rah,” and you run out. Right? We should prime ourselves before important events.

Nico Perrino: What is the sweep then? Is that…?

Bob Ewing: Sweeping is just getting all the shit out of your head because we have so much shit that’s running around in our head constantly.

Nico Perrino: Yeah. Stop looking at Twitter before you look up the speech.

Bob Ewing: It’s not looking at Twitter. No. Are you familiar with Getting Things Done by David Allen?

Nico Perrino: Nuh-uh.

Bob Ewing: David Allen was this super guru back in the 90s, in particular. He’s still around, but he created a system called “getting things done” or GTD, which is this super productivity system. It’s awesome. The very first component of that system is sweep, is sweep your mind. He created what he called a trigger list that you would go through, read all of these different things that will spur ideas in your head. Basically, we have tons of shit in our head, all these different ideas and they’re floating around and we just leave them there. What he says is you have to pull those out because our minds are for having ideas, not holding them. It’s hard to focus your mind with all of this clutter.

Nico Perrino: How do you do that? It’s easier said than done, right? When I think about clearing my mind, I then get anxiety about having to clear my mind.

Bob Ewing: Totally.

Nico Perrino: It’s like when you think about trying to fall asleep is when you have a hard time falling asleep.

Bob Ewing: Yes. 100%. The two ways that I do it is one, I use the the app Otter, which is just a free app you could put on your phone, and I just talk into it, and you just talk it out.

Nico Perrino: Oh, interesting.

Bob Ewing: You literally just exhale. A lot of therapy is just helping people to exhale. The best coaching book, the most popular coaching book right now, The Coaching Habit, he says the first two questions you should ask people you’re coaching are, “What’s on your mind?” and, “What else?” It’s that “and what else” question that really pulls shit out of your head. Once you pull the shit out of your head, then you feel more liberated.

Nico Perrino: Yeah. You know, one of the things that I ask some of my colleagues who are having trouble writing to do is to just write because sometimes, you have so much anxiety about putting the perfect word on the page, and sometimes the way to do that is to talk into something. Just turn on voice dictation in a Google doc and talk about the thing you want to write about. Then, you actually have some words on a page that you can respond to and refine and figure out what’s missing or what’s there.

Bob Ewing: Totally.

Nico Perrino: Maybe you do it on two or three occasions. Maybe get out of the shower after thinking about it and just word vomit in your Google doc. Then later, you can come in and sit down and say, “Okay. What is actually vomit and what is gold?” and refine it.

Bob Ewing: In Bird by Bird, the famous book on writing, she says, “Write shitty first drafts.” The best way to write a shitty first draft is just to talk it out. For speaking, it’s even more important because speaking isn’t writing. Dan Gilbert, the Harvard psychologist, says if you’re gonna speak, your first draft should be spoken, not written, because then, you have to try to perform this alchemy, he calls it, that fails where you try to convert the writing to speaking. We encourage all of our clients to write their first drafts on speeches to write them orally.

Nico Perrino: Oh, interesting.

Bob Ewing: Yeah, and Greg does that already.

Nico Perrino: Oh, does he really? Yeah. Well, Greg does a lot of voice dictation. He is a big for voice dictation. I generally don’t do that, but I try and use that as a tool to break the writer’s block when I’m having a hard time getting words on the page for a first draft.

Bob Ewing: Totally.

Nico Perrino: I just need to get out of my own way and just say what I’m thinking into voice dictation. It puts the words on the page for me, and then see what I’ve got. Right?

Bob Ewing: It’s awesome.

Nico Perrino: That’s sweeping, right?

Bob Ewing: Yeah.

Nico Perrino: You’re trying to sweep your mind and then priming, we were talking earlier before we were rolling about there’s “bah, bah, bah,” and then you were talking about something related, and then it was breathing. What were those two tools?

Bob Ewing: Totally. Priming is just putting your mind into the correct mental state that you want it to be in. I’ll say quickly to tie up the sweeping, the most common way to sweep is to take pieces of paper, little individual pieces of paper and just each idea have in your head gets its own individual piece of paper. That’s the most tried-and-true gold standard way to sweep. I try to do that once a week. That’s gold standard recommended. Sometimes, I’ll even do blue paper and green paper and blue paper will be anything that is causing you anxiety, and the green paper will be anything that’s getting you excited. You get all that shit out of your head.

Nico Perrino: You don’t do anything with those pieces of paper after you’ve done it?

Bob Ewing: The very fact that you do it is transformational to how you feel inside.

Nico Perrino: Oh, interesting.

Bob Ewing: Now, if you want to keep going, then you could go into the whole GTD philosophy. He says once you’ve swept, it’s not only getting shit out of your head, but it’s getting shit out of your inbox. It’s getting shit out of your voicemails. It’s getting shit out of your mailboxes. You have all these different inboxes and so you gather all that stuff together and you figure out where to put it, but it shouldn’t be in your head. You wanna have a second brain where you store everything.

Ideally, what you would do is that you would look at each of these things that’s causing you anxiety and you would say, “What’s the smallest possible step I could take on each of these that will move them forward?” and you write that down on a piece of paper, and then, that is also liberating.

Nico Perrino: That’s sweeping.

Bob Ewing: That’s sweeping.

Nico Perrino: Then, priming.

Bob Ewing: Priming is putting your mind so you’re ready to optimize whatever you’re gonna do. Football players will get together and get all excited. There’s something I sometimes do, and I was actually at Mercatus yesterday. We were doing a workshop and I was teaching these guys something I call the Eddie Jayne, which is Eddie Jayne was this guy I wrestled all through school. In Ohio, Eddie Jayne was the most badass wrestler when I was there. I got to see him wrestle a couple of times.

I never wrestled him because I was tinier than him, but he would get up before the match, he would stare at the person across the way, and he would start jumping around. He would be slapping his legs, slapping his arms, slapping his face, looking at you, and then the match would start and he’d run out and murder you and then he’d go back.

Nico Perrino: Yeah. We used to do that. I ran track in high school and college and I would just pound my legs and pound my back. I didn’t really have a reason for doing it other than I saw other people who were really good at track doing it. It’s the idea that you’re priming your muscles or something.

Bob Ewing: You’re getting yourself excited. Yeah, you could say you’re getting your muscles warmed up, and when we’re going on stage –

Nico Perrino: But, it could also be a placebo. Maybe it’s not doing anything to your muscles, but it’s a sense of you’re getting yourself ready for the thing.

Bob Ewing: The beauty of placebos is that it works even when you know it’s a placebo. Everyone should take a pill every morning that does nothing other than tell you it’s a placebo that will make your day better. But, yes, there’s a whole bunch of ways we can prime our mind, and prime our bodies, and then prime our voice. If you take voice lessons or if you’re a singer, or if you go on stage and you’re a high-powered executive, you’re gonna have people that will help you with your voice. We encourage our clients to warm up their voice before they go out and do an important presentation.

Nico Perrino: How do you recommend they do that?

Bob Ewing: Lips and tongue are both important. These are weird exercises you normally wouldn’t do on your own.

Nico Perrino: We’re gonna do them, actually. Let’s do them.

Bob Ewing: We can do them. Okay. One would be “bah,” right? Bah, bah, bah, bah, bah, bah.

Nico Perrino: Bah, bah, bah, bah.

Bob Ewing: Super classic. And then, there’s the intense version of that which would just be [blows air through lips loosely], like that. Right?

Nico Perrino: Yeah. [Blows air through lips loosely].

Bob Ewing: Yes. Right. The motorboat.

Nico Perrino: Someone’s gonna clip that and make it a meme of me going [blows air through lips loosely].

Bob Ewing: Then, you do the same thing with your tongue. It would be lah, lah, lah, lah, lah, lah.

Nico Perrino: Lah, lah, lah, lah, lah, lah.

Bob Ewing: And then trill. [Trills].

Nico Perrino: I don’t know that I can do that one.

Bob Ewing: [Trills].

Nico Perrino: [Trills].

Bob Ewing: Trust it, dude. Julian Treasure, who’s a famous voice coach, he calls that “champagne for the tongue.”

Nico Perrino: [Trills].

Bob Ewing: You feel your lips, you feel your tongue, you feel them warmed up. You’re warming up your tools before you go use them. Then, you have pitch. Most people stay in this narrow pitch, and you want to expand that, so there’s something called “the siren” that you could do. This is really weird, so you probably don’t want it, but the siren is, you start with “we” and end in “aw,” but “we” is up high and “aw” is down low.

Nico Perrino: Weeeeeeawwwww.

Bob Ewing: Yeah. Weeeeeeawwwww. Weeeeeeawwwww. That’s weird stuff, right? It helps you open up your voice, it helps you open up your throat, it helps you to experience that range and all –

Nico Perrino: You watch documentaries about singers. They’ll sometimes have them getting ready in the green room and they’ll do things like that.

Bob Ewing: Dude, totally, because it’s helpful, right?

Nico Perrino: Yeah.

Bob Ewing: Just like when you watch a sports athlete who’s really good. Watch LeBron James. He’s not just flipping through Instagram the hour before the match.

Nico Perrino: He’s taking the chalk and throwing it.

Bob Ewing: He’s getting ready, man. You’re getting yourself primed so you can be successful. Speaking is your whole body, so I encourage folks to do some type of an Eddie Jayne thing. I encourage folks to go to the bathroom before a big moment, before they go on stage. Three reasons to go to the bathroom. One, because you don’t want to be squirming around halfway through being on stage. Second one is you wanna look yourself in the mirror. Do I have anything stuck in my teeth?

Nico Perrino: That’s true. Yeah.

Bob Ewing: Is all my shit together? Then third is one last prime. Look yourself in the mirror and say, “I’m gonna fucking crush it.”

Nico Perrino: The fourth is you might have to go.

Bob Ewing: Well, that’s the first thing is actually go to the bathroom.

Nico Perrino: Yeah, actually go to the bathroom.

Bob Ewing: Yes.

Nico Perrino: You were saying there were some breathing techniques that are aside from kind of the vocal prime.

Bob Ewing: There’s a whole bunch of breathing techniques that are awesome. That’s physiological sighing. That’s absolute gold standard. I’ll say the most foundational thing is called resonant breathing, and this is when you get different systems in your body in sync. Resonant breathing is the most simple, basic thing. Every major religion and culture has independently discovered resonant breathing. I always encourage resonant breathing and then now, there’s this –

Nico Perrino: What is resonant breathing?

Bob Ewing: Resonant breathing is just about six seconds in and about six seconds out. That goes for about six cycles per minute. It’s also called slow breathing and it just very quickly gets you calm. We could do that at any point in real time. Waiting in line at the grocery store, before we’re about to go on a podcast, a couple of cycles of resonant breathing are useful. The most powerful is physiological sighing. This is a new study from Stanford. Huberman. Andrew Huberman’s awesome. He looked at a whole bunch of different types of breathing and said physiological sighing is the best in real time at reducing stress and elevating confidence.

We can go to a retreat for several days, but we can’t always do that in real time, so what do you do right now? You’re about to walk on stage. What do you do? Do a little bit of physiological sighing. It’s two shots in, one out. It’s full breath in, starting with your belly, through your nose if you can. When you’re done, you take an extra shot.

Nico Perrino: You try and get an extra breath [inhales]… and then, you… [exhales].

Bob Ewing: Yeah. That pulls all the carbon dioxide out and it changes your heart rate variability. It changes the size of your heart. I know you’re into health. Are you familiar with the heart rate variability stuff?

Nico Perrino: Not really.

Bob Ewing: I wear an aura ring to measure sleep and all this different stuff. Now, they can measure heart rate variability, which is the variation in our heartbeats over time. We think maybe it’s about one beat every second, but really, it might be 0.9 here and then 1.2 here. Counterintuitively, the more variation you have, the healthier your heart.

Nico Perrino: Oh. I didn’t know that.

Bob Ewing: Yeah. Physiological sighing, when you breathe all the way in, it kind of smooshes your heart, and when you come all the way out, it expands your heart. It ends up changing your heart rate variability in a way that is conducive to just feeling less stressed and more confident.

Nico Perrino: Now that we’ve primed, I think –

Bob Ewing: Let’s do it.

Nico Perrino: You’ve been mentioning your company, which is Ewing School.

Bob Ewing: Yeah.

Nico Perrino: You’re Bob Ewing, of course.

Bob Ewing: Yes, sir.

Nico Perrino: You’re the founder and, I’m assuming, president. Do you have that title?

Bob Ewing: Yes, sir. I’m the founder and president and Maryrose is the CEO.

Nico Perrino: Okay. You and I go fairly far back. When I first started at FIRE, I was – Greg Lukianoff who you worked with on speaker training and his speeches and what not, he’s the president and CEO of FIRE. I was his assistant and FIRE was a 12, 13, 14-person organization at the time.

Bob Ewing: That’s amazing.

Nico Perrino: Yeah. He and I were working on his book when I first came along, his first book called Unlearning Liberty. I had some experience doing advertising and marketing at Indiana University, and that’s what I thought was gonna go into before I ended up coming to FIRE. When that book came out, I helped him with the comms for it because believe it or not, in 2012 when I started at FIRE, we didn’t really have a communications shop. We had a public awareness program on which many people worked, but nobody doing core communications work.

Bob Ewing: What took you to FIRE?

Nico Perrino: I was an intern at FIRE in 2010.

Bob Ewing: Why did you go and intern at FIRE?

Nico Perrino: I had always been interested in issues of political philosophy and the Constitution.

Bob Ewing: Pictures of Luke?

Nico Perrino: I’m sorry to say that I learned about Luke Skyywalker and that’s the principle in 2 Live Crew here who’s, for our radio or podcast listeners, they can’t see. I’ve got a poster of Luke Skyywalker on my wall because his album, one of his albums, I think it’s Nasty as They Wanna Be, was deemed obscene in the state of Florida and actually, there were people who distributed the album who were charged with crimes for selling it. He became kind of a First Amendment advocate and he came out with later, a song or an album called Banned in the U.S.A. I’ve got that poster on my wall with a picture of him with his hand in his pants.

Bob Ewing: Dude, I love that. That’s so great.

Nico Perrino: The other side is actually him flicking off –

Bob Ewing: Yes.

Nico Perrino: – whoever’s looking at it. When he worked for –

Bob Ewing: I remember this album. My brother had it when I was a kid. It was like anyone who doesn’t like the First Amendment, I have a picture for you. You open it up and he’s flicking you off.

Nico Perrino: Yeah, he’s flicking it off. He became a big advocate for –

Bob Ewing: This is Luke Skyywalker from 2 Live Crew, not Luke Skywalker from Star Wars.

Nico Perrino: Yeah, he spells it little bit differently, and I don’t know if it’s a play on Luke Skywalker from Star Wars, but I think there’s two Rs at the end of it or something. I don’t know, but he became kind of a First Amendment hero because he ended up winning that case involving obscenity and became an advocate for free expression more broadly. Killer Mike actually, in his speech at FIRE’s gala earlier this month, talked about Luke Skyywalker and 2 Live Crew. Is his name actually Luke Skyywalker or is it… Luther Campbell, I think, is his name.

Bob Ewing: It’s Luther Campbell. Yeah.

Nico Perrino: Yeah, but I think he went by Luke Skyywalker or something like that.

Bob Ewing: And Uncle Luke.

Nico Perrino: Yeah. I guess he does some really good work. I think he’s based in Miami. Killer Mike was telling me that he does some really good work for the community. Anyway, no, that’s not why I came to FIRE, but I’d always been interested in issues of free expression, and the Constitution, and we had a question come up with one of the student groups I was involved in involving student fees and funding, the funding that our student group could get to bring a speaker to campus. We didn’t know what our rights were or what really was required of the university.

It just so happened that FIRE had recently distributed their guide to student rights on campus to our student group and one of those four or five guides was “The Guide to Student Fees and Funding.” FIRE still does this. Student groups that we work with, we try and distribute these guides so that they know what their rights are on campus. On the back of the guide is, of course the URL to the website, which I went to, and just so happens out of coincidence that at the time I went to it, FIRE was advertising its internship program. I applied, I ended up getting it. I ended up moving to Philadelphia. The rest, as they say, is history and that was 2009, 2010 when I applied, 2010 when I was an intern and it’s 13, 14 years later.

I’m still here all because FIRE just so happened to be advertising its internship program when I went there. Anyway, then I came aboard in 2012 as a full-time employee, as Greg’s assistant, and after doing the book, Greg recognized the opportunity to have a communications department at FIRE. He said, “Oh, you did great work on “Unlearning Liberty.” Why don’t you transition out of being my assistant and be our first communications staffer?” so, I was a communications coordinator and I had no idea how to do any of this work. I went to journalism school. I studied a little bit of advertising and marketing. I had a knack for just getting things in front of people, but I have no philosophy.

I had no idea how to put together a pitch to a journalist. I had no idea how to win in the court of public opinion, more or less. What I did, and I think what any person who’s actually interested in learning in this space would do is I reached out to people who did do this stuff in a way that I admired. I reached out to the Drug Policy Alliance, for example, and to a train up to Manhattan and met with them and said, “How do you do communications work?” I also reached out to you and your colleague at the time you were working in the Institute for Justice, Mark Meranta. I’ll never forget. It’s one of the more life-changing things that ever happened to me.

We went out for lunch. We sat at an outside table. I forget what the name of the place was, and you brought out a presentation that you had clearly given before and just walked me through the process of doing communications work at the Institute for Justice. Not just the tactical approach to it, but also the broader philosophy behind why you did things tactically. I took a lot of the learning back from that conversation and tried implement it here at FIRE to, I hope, good effect. Over the years, we’ve remained in touch.

You’ve given me advice in many other contexts as well including recommending, when first got into the workforce, that I should put as much money as I can into my 401(k), or nonprofit worlds, 403(b) because one day, I might have kids and I might not have as much disposable income, so you get it there now and you work with the compounding interest. It’s a pleasure now that you’ve started the Ewing School that you work with FIRE staff on developing their speaking skills, and refining their speeches, and doing media trainings.

The purpose of this conversation is not only to thank you for effectively getting FIRE’s communications department up and running without really knowing it, but two, to kind of bring some of the lessons learned over the last 20 years of your career or whatever and talk with our audiences about what makes them effective speakers but more precisely, what would make them an effective advocate for free expression in the court of public opinion. I want to get started and talk about audience. I know that’s a big message for you is you need to have an idea of who your audience is when you are preparing to go into the court of public opinion.

Bob Ewing: Yes.

Nico Perrino: How do you work with your clients to do that, to help identify the audience so that you’re not just talking to the masses, so to speak?

Bob Ewing: Absolutely. Yeah. It’s an excellent point. I would say the highest level of communication is about connection, and what we wanna do is we want to connect with our audience, and we want to connect our message with our audience. Ideally, the better we can understand our audience, the more effectively we can connect. We wanna make sure we’re not doing things that disconnect us from our audience. When we work with all of our clients, we always say, “First and foremost, who is your audience, what are they interested in, and how can you help them?” That’s where you start whether it’s a big presentation like Greg and Will will just did –

Nico Perrino: At the gala.

Bob Ewing: – at your FIRE gala, or whether it’s a conversation that you’re having in line at the grocery store. Who’s the audience, what are they interested in, and how can you help them? That’s the starting point for effective communication.

Nico Perrino: One of the challenges that I have, not necessarily within the communications department, but working with the other programs that we have here at FIRE here, and I’ll put this down here. This is another book you recommended to me, Made to Stick, which now has become this sort of comms bible within the communications department so to speak, but you can put your coffee on that so it’s not clinking. One of the challenges I have working people out of communications is they have a program, or they have a case, or they have a report, or they have something that they’re trying to get out.

Working with them to identify an audience is hard because your instinct is, “I want everyone to know about this,” because you think it’s important, because this is something you’ve worked long and hard about and you think people should care about it. That’s not always the best approach to messaging, for example, FIRE’s internship program, or for this particular case, or this particular survey.

For example, we just did a survey of college scholars and the amount of times that they’ve been punished for what would be First Amendment protected speech related to their academic work. We’re sitting down and we’re talking about it. Is the audience for that report all Americans because we’re all in America and these scholars are in America, and we think that all of them should care about the scholars, or should it be something more narrow? I think for folks who don’t work in the communications department, the answer is always, “Everyone should care this because I care about it.” Do you have that problem when you’re working with clients?

Bob Ewing: I’ll tell you a quick story that that brings to life. Back when I worked at the Institute for Justice, there was a new attorney that started named Arif. Did you work with Arif?

Nico Perrino: Yeah, I worked with Rif.

Bob Ewing: Rif’s awesome, right?

Nico Perrino: Yeah.

Bob Ewing: Rif had just started and he said, “I want to pitch an op-ed to the Austin American-Statesman.” He was living down in Texas. And I said, “Dude, there’s no reason to pitch an op-ed to the Austin American-Statesman because they’re not gonna run it because they don’t respond to my emails. They’re an amazing paper. They’re the paper of record in the capital in Texas, but they do not respond to my emails. It’s a black box. You cannot get into the Austin American-Statesman.” He said, “Well, I think that I still want to do that.” I said, “But, it doesn’t make sense.” He said, “Well let me send you over the op-ed, the idea I have in mind, and you take it and read it.”

I start reading this totally skeptical and by the time I finished, I was like, “Holy shit, dude. I think this might work.” What he wrote was he wrote a piece that said, “Austin, you guys have the best food truck regulations in the state and the rest of Texas needs to be more like Austin.” San Antonio just passed some bad regulations in particular, so there’s timely hook. [Inaudible] [00:23:53] oh my god. I sent it to the Austin American-Statesman and they write me right back and they say, “We love it. We’re in.”

He’s written a whole bunch of pieces for the Austin American-Statesman now. It was sort of like, “Of course.” I had been sending pieces to the Statesman that were saying things like, “Austin, you have bad regulations. You need to be more like someone else.” It was not audience-focused.

Nico Perrino: Right. I remember that’s one of the points that you made to me during that first meeting which was, you need to bait the hook to sweep the fish. That might be an old proverb, so to speak –

Bob Ewing: An old proverb.

Nico Perrino: – that you don’t use anymore, but the idea is you’re not gonna send a pitch, a story pitch to national review in the same way you’re gonna do it to Mother Jones. Right? They have two different editorial perspectives, two different audiences, two different sets of interest. You need to tailor your pitches to the audiences you’re trying to reach, and in the case of the Austin American-Statesman, not only are you giving them props because their city of Austin is doing something well, but you’re comparing it to other things that are happening in the state that’s within the readership as well.

One of the cases that I like to reflect back on, because I also worked at the Institute for Justice for a time, was our civil asset forfeiture case involving Philadelphia’s civil asset forfeiture program, which was among the most corrupt and abusive in the entire country. One of the hardest places to get your story to run is on cable television, television just in general. They run three stories a day and civil asset forfeiture often isn’t one of them. We thought, well, if we could identify a host or a producer who has a connection to Philadelphia and might be uniquely interested in what’s happening there, maybe we might have a chance.

We did some research. We found out that Jake Tapper is from Philadelphia. You go to his Twitter account, he’s talking about things that are happening in Philadelphia. Of course, he’s a popular host over at CNN so we pitched him. Lo and behold, it worked. He decided he would take it as an exclusive and they ended up running the story. He ended up introing the story, but it was run by one of his segment producers who does legal stuff. It’s more work, but you need to figure out how you can make your message resonate with a particular audience if you do want it to resonate with that audience.

Bob Ewing: Totally, and it doesn’t matter what the context is. One of our clients argued a case on Wednesday before the Supreme Court. That’s a very high pressure, high-stakes environment. You have an audience of nine. There’s nine people and they come from a diverse variety of backgrounds and different ideological beliefs. The idea here, this was Christina Martin who is arguing Tyler v. Hennepin County, the case from the Pacific Legal Foundation. It’s a property rights case that has to do with home equity theft. The point was when she’s preparing, she’s not just thinking, “Okay. Home equity theft. What do I think about it?”

It’s, “What do I think about it in the context of these nine people that I’m interacting with? What’s every conceivable question I could get from each of these nine people? How will they approach the case? What specifically will they be interested in and how can I help them to see it in a way that makes the most sense from my perspective? I want to set the terms of debate in a way that makes most sense for me understanding the world through each of their eyes.”

Nico Perrino: Yeah, and sometimes, it’s even narrower than the nine justices. Sometimes you know as an advocate in front of the Supreme Court who the justices are who are probably already on your side, and sometimes you’re going up there and making your argument to one justice who’s gonna be the swing justice, who’s the one justice you need to convince. You’re not ignoring the other justices, but your topline talking point, your topline message is really to appeal to this originalist justice who is skeptical of your arguments but you really need them in order to win, to get that fifth vote.

Bob Ewing: Totally. Right. If you’re speaking to students on a college campus, it’s gonna be different than if you’re, say, keynoting at the FIRE Gala.

Nico Perrino: Oh, totally. Yeah. We have some of that issue right now at FIRE since we expanded our mission in June of last year. We recognize that a lot of people who have been FIRE subscribers to our email accounts or social media stuff, they’re gonna start getting a lot of stuff that isn’t on college campuses anymore. Alternatively, we have people that are coming in because they’re excited about FIRE’s new mission, expanding our free speech advocacy off-campus, and at least at the outset, this was a conversation we had.

All of our programming is still about campus because we haven’t revved up the off-campus program yet. We’re bringing all these people in and they’re just seeing campus stuff, but maybe that’s not what they’re interested in. We needed to be very deliberate and thoughtful on how we mixed up content, how we introduced new off-campus content to our on-campus advocates and supporters, and that’s hard. It takes a lot more work. It’s a lot easier just kind of follow inertia and just blast your message out without any sort of thought or strategy behind it.

Bob Ewing: Totally. There’s a great quote from the tech writer Ken Haemer that says, “Giving a speech without an audience in mind is like writing a love letter and adjusting it ‘to whom it may concern.’”

Nico Perrino: You put that in your Substack. What’s your Substack again by the way?

Bob Ewing: It’s called Talking Big Ideas.

Nico Perrino: Talking Big Ideas. I recommend it to everyone. I’ve probably emailed our staff three or four times saying, “Everyone needs to get this,” or forwarded one of your messages from that. You did have a Substack newsletter a couple of weeks ago where you had that quote. “Speaking without an audience in mind is like writing a love letter ‘to whom it may concern.’” It’s just brilliant. I’ve used it 20 times since I read that. Yeah, exactly right. You can understand it intuitively.

Writing a love letter to no one in particular is not going to be an effective letter. We don’t think about it in the same way when we’re doing public interest litigation or advocating the court of public opinion for constitutional rights. You just don’t always do that.

Bob Ewing: The important thing too is that we’re still true to ourselves. It’s not that we’re saying I have to change who I am to appeal to different audiences. It’s how can I best connect who I am to these different audiences. Here’s a quick example of that. Years ago, I went to a VIP dinner at the Willard Hotel here in D.C. A bunch of presidents have lived in that hotel. It’s a VIP hotel. Lots of senators and politicians hang out there.

Nico Perrino: Right across the street from the White House.

Bob Ewing: Yes. I’m on the second floor. We’re in this dinner. There’s just 12 of us sitting around one table, closed door, there’s two people at the table that are current U.S. senators. There’s heads of commissions. There’s some researchers. I’m there to facilitate conversation. The guy to my right was a guy named Adam Thierer. You may know him. He works at R Street. He was at Mercatus at the time and he had done research about 20, 25 years on tech policy issues.

He wasn’t saying anything and I thought he maybe he was really scared because there were these high-status people at the table. Halfway through the dinner, he still hadn’t said a word. I thought, “Oh, maybe do I try to get him the ball or he’s too scared?” Then, at some point, he ends up getting the conversational ball to land in his lap and he absolutely knocks it out of the park. He gets a follow-up question. Crushes it. The rest of the dinner was the Adams Thierer show.

Nico Perrino: Yeah. The center of gravity had shifted in the room.

Bob Ewing: The center of gravity had totally shifted to him. When the dinner was over, normally people gather around the highest status person, one of the senators. Everyone gathered around Adam. He had become the highest status person in the room and afterwards, I asked him, I said, “How the hell did you do that?” He said, “I’ve been doing research on a whole bunch of different kinds of issues for the last 25 years.” He always takes the best stories, and Proverbs, and analogies from his different research and says, “I’m gonna save these and hold onto them.”

He actually prints them out and keeps them in a binder, which is intense, but he stores them in the cloud as well. That’s what we encourage all of our clients to do is capture all the different stuff that you’re saying, clarify it into – we like to say communication is fundamentally connection, and then you have audience, messaging, and delivery. We can talk about that, but the messaging is to capture your messaging and clarify it over time. It’s a long-term game. Once you have that storytelling catalog, if you will, saved in the cloud, then when you’re going over to an event like Adam was, he said, “I was just riding the lift right over to that event and I pulled up my catalog and I flipped through it.

I thought, “What of my ideas will resonate most with this audience? Oh, they’re gonna like this analogy. They’re gonna like this story. They’re gonna like this shit.” Then, when he’s there, he’s got all of this shit ready so he’s not just babbling at them, but he has his ideas that he’s clarified and he picks the correct ones for that audience and they love it. It’s like starting off every conversation on third base.

Nico Perrino: Yeah. I love that story, which I have heard you tell before, and I was listening to a podcast with Matthew Weiner who is the creator and writer for Mad Men. The host had asked him how he found his ideas for the show or anything that he works on. He says, “I keep a catalog of ideas. Essentially when a very human moment happens in my life,” whether it’s something as simple as his kid kicking a soccer ball for the first time, or the way he felt after a loved one died, he just writes a sentence about that happening.

I thought that was such a wonderful way to introduce real life into storytelling, but it’s something that a lot of us don’t do because when you’re sitting in front of the blank page, you have a hard time recollecting all that stuff. One of the superpowers that you can do is being organized with what works, what’s happened to you, what are the stories that you’ve told that were most resonant and for what audiences. It’s not the same thing that he’s doing, but it’s collecting things from your past that you can use again in different contexts.

Bob Ewing: Totally. Yes. Authenticity trumps profundity. We often think that we have to have these crazy ass stories to end up connecting with our audience and that’s absolutely not true. We just have to speak in an authentic way. When you capture those little stories from your life, it helps to bring them to life and connect with our audiences. It’s a fantastic exercise.

Nico Perrino: Yeah. You just give your characters that you’ve already created more connection with the average person because if you had that experience in your life, chances are millions of others have had it as well and so they’ll be able to connect on it. The last thing on the audience point just because it’s something we experienced this week, some of our listeners might be familiar with the story that Disney is suing the state of Florida, the DeSantis administration, because the state had taken away some of its privileges tax and otherwise that had previously been granted.

It’s very clear because they opposed the DeSantis administration’s parental rights and education bill, often referred to as the “Don’t Say Gay” bill, and Republicans in the state were very upset about that. As as a result of that, they said we’re gonna do something and you’re gonna kind of regret that you opposed us on this. FIRE came out and said, “Yeah, this is a serious First Amendment issue. This is First Amendment retaliation. Disney doesn’t have the right to this privilege, but it’s also unconstitutional to revoke it for an unconstitutional reason, which is political advocacy.”

In writing our statement for that and creating our message around that, we understood that the audience that we’re trying to reach were conservatives who might be sympathetic to the DeSantis administration and might be some sympathetic to the underlying bill, the parental rights and education bill. We needed to explain to them that the same tools that you might give a pass to the DeSantis administration for use in the state of Florida can be used by others who you might be more inclined to agree with can be used by other politicians and states that you disagree with, for example, in the state of New York.

We drew the analogy. In the state of New York, they’re using financial regulations to try and blacklist the NRA so it can’t do business in the state. Essentially, it can’t get insurance, it can’t have any banking operations set up in New York State all because of its advocacy around gun rights issues. If you give DeSantis a pass in Florida, that also means that you’re giving a pass to the state of New York and going after the NRA. We could’ve just gone after the DeSantis administration or the state of Florida, but then, we wouldn’t have been able to demonstrate, we wouldn’t have really reached conservatives without showing that this is the cost of letting this go too.

We did the same thing in South Carolina and North Carolina surrounding abortion where in South Carolina, they were trying to criminalize speech relating to abortion. Not abortion itself, just speech about abortions. We came out as advocates against that and were effective in defeating that bill. At the same time, in the state of North Carolina, the student government at UNC Chapel Hill was trying to deny funding to any group that advocates a pro-life position more or less. We said, “Look. This goes both ways. If you want the freedom to speak about abortion, you need to protect the freedom for others to express a pro-life message.”

I think that is one of the more effective ways in just advocating for free speech more generally to make people understand that it’s your ox that can be gored the next time. What’s good for goose is what’s good for the gander.

Bob Ewing: Yep. One thing that I would add that too is Maryrose and I were with my mom last week in Tuscany, which is an absolutely gorgeous vacation, and a lot of people didn’t speak English. It really drove on this idea that in different places, people speak different languages. It made me think about Arnold Kling’s book, The Three Languages of Politics, and just how important that is. Are you familiar with Three Lang – okay. A hundred percent recommend picking it up.

Nico Perrino: Would you say the name again?

Bob Ewing: Arnold Kling, The Three Languages of Politics. Absolutely fantastic book. What he says is – you're familiar with Jon Haidt’s ideas on the righteous mind where he says there are these six different moral bubbles that we live in, and we all give different weights to them. Kling takes that a little bit further and says really what we have right now in the United States at this time in this context, we have three, and now he's even updated it to say probably four different languages that we're speaking when it comes to politics and ideology.

He says if you're speaking your language to someone who speaks a different language, it's not going to be effective. We need to learn how to speak the language of the people that we're talking to and be audience-focused. The four different languages that he identifies are progressivism, conservativism, libertarianism, and now populism. He says they operate on different axes and they talk in different ways. He'll go through and say, “Here's Black Lives Matter from each of these different languages.” And you see it like, “Oh my god, yeah. And you can do this now for COVID, or you could do it for the DeSantis Disney thing.

You can say okay, I want to put this in each of in these different contexts. He says progressives are fundamentally operating on an axis of oppressed to oppressor and that's the context through which they're seeing the world and how they're understanding and talking about that issue or whatever it may be. Conservatives have civilization to barbarism. Libertarians of course have liberty to tyranny and then now, the rise of populism, there's this nationalism to globalism.

He says if you want to effectively connect with people, address their love letter, so to speak, to the audience that you're talking to. If you're talking to a conservative audience, frame what you're saying in a civilization to barbarism perspective rather than maybe a libertarian or progressive perspective.

Nico Perrino: That’s really smart because Jonathan Haidt does talk about that sort of issue in The Righteous Mind and you need to appeal to people's moral intuitions or instincts.

Bob Ewing: Yeah. Another huge thing here is the difference between System 1 and System 2 thinking, Dan Kahneman’s iconic book.

Nico Perrino: Yeah. You might need to break that down.

Bob Ewing: Dan Kahneman, famous writer, thinker, the first non-economist to win the Nobel Prize in economics, he wrote Thinking, Fast and Slow and he wrote Noise, which are fantastic books that we should read and understand. In Thinking, Fast and Slow, he says, fundamentally, we have a System 1 type of thinking and a System 2 type of thinking. System 1 thinking is quick and responsive and intuitive and we need this all the time. The tiger jumps out at us and we run away, or something happens that we need to very quickly respond to. Then, we have this other type of thinking which is very slow and deliberative. He calls the slow one System 2.

Most of the time, Haidt says, in The Righteous Mind, his first principle of social psychology is intuitions come first and reasoning follows. He says we make a quick System 1 judgment of the world and then we use our System 2 thinking to justify our intuitions. We use the deliberate to justify the intuitive. There's a lot of truth to that, but we're not confined to only using our slow, deliberative brain to justify our intuitions. We can break free of that and as Arnold Kling says, we don't have to have our System 2 brain be a lawyer that's justifying our actions. We can have it be a judge that's honestly trying to seek the truth. Is there someone coming in?

Nico Perrino: No, I think my colleague on the other side of the wall is nailing something to the wall. Hopefully, it's just one nail.

Bob Ewing: The idea is that understanding that most of the time when we’re interacting with people, ourselves included, we're engaged in very quick System 1 thinking. What’s important is we're making judgments, snap judges and intuitions and they’re biased based on the language that we speak. We can overcome that and be slow and deliberative and say I'm going to move into a System 2 framework where I'm going to be trying to honestly understand the truth rather than just justifying my own intuitions.

Nico Perrino: Easier said than done though, right?

Bob Ewing: Yes, and this gets to a design problem, right? We can design the context that we’re interacting with people in a way that pushes us into System 2 thinking.

Nico Perrino: That's kind of like, this is the follow-up of The Righteous Mind, which was The Coddling of the American Mind. It's not the same subject necessarily, but there is some connection because they talk in The Coddling of the American Mind, Jonathan Haidt and Greg Lukianoff, FIRE President, about cognitive behavioral therapy, which I think a way of not reasoning toward coming up with reasoning towards your initial instinct, but it's like let's judge it accurately by giving it a label of how we distort our thinking sometimes and distort our analysis.

The, the idea being, okay, I responded this way to this situation, but then you come back and you take out your pen and paper and you write out your thoughts about it and you're like, “Oh. This is catastrophizing,” or, “This is black and white thinking. Is my initial analysis of the situation really catastrophe, or is this just my mind playing tricks on me?

Bob Ewing: Totally. CBT is a way to prime our minds to engage in more System 2 thinking.

Nico Perrino: I want to move away now from audience. You have your audience in mind but then you need to identify what your message is, which is the hard thing to do. You advocate for finding your big idea.

Bob Ewing: Yes.

Nico Perrino: How do you do that?

Bob Ewing: That's hard.

Nico Perrino: Yeah.

Bob Ewing: Richard Feynman said that anyone could explain something complex in a complex way, or explain something simple in a complex way, but to explain something complex in a simple way, that's hard.

Nico Perrino: To distill it down to its essence.

Bob Ewing: Yes. To make it as simple as possible, but not simpler. We always encourage all of our clients to think about, again, messaging, delivery, audience. These are the three buckets that we want to be thinking about because what we say matters. The effectiveness of our ability to communicate is going to determine in large part the effectiveness of whatever it is that we're working on. The more we can break it down into who's the audience and then what specifically is the message that I want to get to them, and how can I deliver that in an effective way, that will largely determine how successful we are.

Messaging, I would break down into content and structure. For content, we always recommend everyone to say, "Whatever you're talking about, what's the big idea, and then, how do you bring it to life?” We always encourage three different things. We call them proverbs, stories, and analogies. A proverb would be, what's the one thing that you want to stick in everyone's head so when you're done talking, it's there?

Nico Perrino: Yeah. I remember when I was at IJ, and I think this is something that you discussed in our initial meeting as well, you would talk about, what is the theme. My colleague is still hanging stuff in the room. Can you let Bob know, Tyler, that we're recording a podcast? You would talk about the theme. What is the one thing you want the audience to come away with? Then, you would build talking points or, when we were at The Institute for Justice, SOCO, strategic overriding communications objectives –

Bob Ewing: Which is ironic.

Nico Perrino: – in support of that theme. The theme was often just the distillation of everything you were trying to communicate. What is that one core message? It could be as simple as, “It’s just a box.”

Bob Ewing: Yeah.

Nico Perrino: Right? Do you wanna tell that story?

Bob Ewing: Sure. Yeah. That's Jeff Rowes. The Institute for Justice filed several cases in different courts in different jurisdictions going after a particular occupational licensing law. In this case in particular that we're talking about, it had to do with caskets being shipped across state lines, and it got into technical legal stuff. Law gets complicated, economics gets complicated, and yet, as with anything, if we put enough effort in, we can find a way to explain complex things in a simple way.

What we came up with in that case was a proverb that was no more than four words long and none of the words had more than four letters which was, "It's just a box.” These caskets are just a box and then this simple proverb, if you will, that we connected to that, there's no reason to require a license to sell what is just a box. The only reason this licensing law is on the books is to protect the financial interests of the powerful funeral lobby.

Nico Perrino: Your clients were monks, right?

Bob Ewing: Yeah. Our clients at the Saint Joseph Abbey are prepared to go all the way to the Supreme Court if that's what it takes to vindicate the right to earn an honest living for Americans everywhere. That “it's just a box” theme showed up in everything, in op-eds, in conversations, in donor meetings, and before court arguments, testifying, whatever it may be. That big idea gets translated.

Nico Perrino: Yeah. You're talking about all of these complex economic regulations, policing how caskets are made in the state of Louisiana, I believe. Right?

Bob Ewing: In that case, yes.

Nico Perrino: Yes, in the state of Louisiana. You said you don't really need to understand all these complex economic regulations if you just understand that it's just a box. You don't need all that BS and all that red tape to create a box. Right?

Bob Ewing: Watch really good speakers speak and this happens. This goes back probably thousands of years, but Bourke Cockran hammered this home. He was perhaps the most influential speaking coach of the 20th century for elites, and then I would say Dale Carnegie was for the commoner. Bourke Cockran trained people like FDR. Winston Churchill said the single most influential person in his life was Bourke Cockran, and Bourke Cockran said, “Always, always, always make just one point and that's it, and drive it home.”

Nico Perrino: Yeah. We did a speaker training, a media training recently where we were talking about the difference between a good speaker and a good communicator. They're not always the same thing and the comparison was brought up between Ted Cruz and Donald trump. Ted Cruz you can listen to him on the floor. He talks about the Constitution and he's a very good speaker. I think he was a debate champion in high school or college. He's also, I think, the attorney general in Texas, although, I could have that wrong. He argued in front of courts. He knows how to be a good speaker.

You could listen to him for an hour and not remember anything he said. On the other hand, Donald Trump, who many people don't see as a good speaker because he talks in circles, but you know the main messages that he's coming away from whether you agree with them or not. He's communicating a message that sticks and that are instilled down into their essence. Sometimes, just seeing someone who looks very polished doesn’t mean they're also a really good communicator who will leave an impression on that audience.

Bob Ewing: You know what? I would say on the idea of “what's the big idea,” watch people and whoever you really like, even if it's political people, even the people that you don't really like, people that are effective. I like to use Steve Jobs as an example. Steve Jobs put a ton of work into speaking, and watch him introduce a new product like the iPhone. It's a complicated technological thing that he's talking about and yet, it’s crystal clear. Proverb is five words. “Apple is reinventing the phone.” He said “reinventing” over, and over, and over, and over, and everyone who watched that talk and heard that talk knew Apple is reinventing the phone.

When Will was at the gala, your FIRE gala, “If it's protected, we defend it,” and that's clear. And Greg. It's clear. Fight for free speech every day. Killer Mike was talking about the importance of understanding your enemy. Free speech allows us to hear and understand people we disagree with.

Nico Perrino: Yeah. You know, often times, when you're thinking about your big idea, you're often thinking about how you want to frame the debate. You want to make this debate about whether we really need all these onerous regulations surrounding a box. We do that at FIRE too.

For example, we've had cases in the past on college campuses involving so-called security fees. These are fees that are levied by the college or university against students or student groups who want to invite a speaker to campus and who might be controversial. The idea being that if you want to have Ben Shapiro on your campus, then you know the protests are going to come and we're going to need more police presence, we might even need to buy or rent barricades to put around the event to avoid any sort of violence or disruption at the event.

We had a case in Western Michigan University involving rapper and social justice advocate, Boots Riley. He was being brought to campus by the Kalamazoo Peace Commission, but he is a somewhat controversial speaker and they levied an excessive security fee on him. We were thinking about how to message this. It's like, people like security. They might not have any objections to a security fee, but what we're really trying to communicate is that this is a tax on controversial speech in the United States of America.

We can't discriminate based on the content of the speech. We said, why would we adopt our terms of the debate and use security fees? Why don't we just call it a speech tax? That's what it is.

Bob Ewing: Love it.

Nico Perrino: Right?

Bob Ewing: Yeah.

Nico Perrino: That's the big idea from this case is that you cannot tax speech in America. As you said with “it's just a box,” it made it into op-eds, it made it into news stories and headlines. Sometimes, you even do this. You create this kind of zeitgeist and this framing around issues without even intending to do it. We mentioned Jonathan Haidt and Greg Lukianoff’s book The Coddling of the American Mind. That was not their initial title for that book. It originally started as an Atlantic article. It was originally supposed to be titled Disempowered. The idea is that we are creating systems and processes and teaching kids to become disempowered and lose some agency.

Bob Ewing: Greg wanted CBT in the title, didn't he? In the subtitle?

Nico Perrino: It might have been. It might have been. I don't remember what the subtitle would have been, but I remember the –

Bob Ewing: Disempowered. I like it.

Nico Perrino: Yeah, I remember the Disempowered. A lot of people on the outside bold realize that when you write an article, you usually don't pick the headlines for publications like The Atlantic or The New York Times. I just wrote an op-ed for The L.A. Times where they picked a title I wasn't happy with. People are fighting over the headline. I was like, “That's the one thing that I didn't write for this piece. Why is that what you're debating?”

You can shape the terms of debate even unintentionally. The Coddling of the American Mind became a meme. It became the way you talked about what was happening on college campuses, even going so far as two weeks after the original article came out, it was the second most read cover story in Atlantic history. Barack Obama's on the stage saying, “I don't think when you go to college that you should be coddled and protected from different points of view.”

Bob Ewing: I love it, dude. The Atlantic's been around for a few years.

Nico Perrino: It’s been around for a few centuries at this point perhaps.

Bob Ewing: That’s awesome. I wrote a piece called, “I Did Not Kidnap Anyone.” The whole point of it was you should always set the times of the debate. Speak in a positive and solutions-oriented way. Use your terms, not terms that frame what you're talking about in a way that you don't want it framed. There is a classic tweet where a guy said, “I did not kidnap anyone.”

Nico Perrino: Richard Nixon. "I’m not a crook.”

Bob Ewing: Richard Nixon. “I’m not a crook.” You listen to that, and you listen to Bill Clinton say, “I did not have sexual relations with that woman, Miss Lewinsky.” What’s the one thing that you think about that guy knowing nothing else about it? You hear Nixon say, “I’m not a crook.” When you frame things

Nico Perrino: “I didn’t kill my wife.” Yeah.

Bob Ewing: Yeah. “I don’t beat my wife,” right? You’ve framed things negatively and you’ve prime people to think the opposite. We always want to state things in a positive and solution-oriented way from our perspective and think about it in advance.

Nico Perrino: Yeah, so they're not thinking about security. They're thinking about taxes on speech.

Bob Ewing: Yes, and it's brilliant.

Nico Perrino: People hate taxes. Well, most people hate taxes.

Bob Ewing: Jimmy Carter paid extra taxes, I think.

Nico Perrino: Oh, did he?

Bob Ewing: I think he was paying extra, but yes. Most people don’t like taxes.

Nico Perrino: Yes. The last thing I want to talk about on this messaging, and I hope you do have 15 more minutes because there's two other subjects I want to get to.

Bob Ewing: We'll go as long as you want.

Nico Perrino: Okay. Numbers. Please help me with numbers. I work in an organization –

Bob Ewing: [Inaudible] [00:55:05].

Nico Perrino: Yeah. Bob's holding up the book Making Numbers Count by Chip Heath and –

Bob Ewing: Karla Starr.

Nico Perrino: – Karla Starr. Another book that Bob recommended to me. If you don't have time for even this slim of a 150-page book, Bob has a recent Substack article out talking about numbers and how you communicate numbers. They're among the most difficult thing to communicate. What you say in your piece, “How to Communicate Numbers,” is that nobody truly understands numbers. This was one example that you used in your Substack piece that you use to, I think it's “compare,” is how it would fit into the cut, simplify, and compare proverb about the solar system. Right?

Solar system, things are light years away, which you might not even know what a light year is. Things are trillions of miles away. How do you really understand just how far something is in the solar system? You have this kind of example that you use that could simplify it for our audience.

Bob Ewing: Totally. Yeah. In this context, the nearest solar system is something like 3.98764 or whatever trillion miles away. None of us understand that massive number. It doesn't matter if you can't cut or simplify in this case. You could simplify and say it's about four light years away, but we don't understand a light year. In this case, if it’s just one number but we can't simplify it to the extent that we can really understand it, then we have to find a comparison.

The example here is imagine that you are at your high school football stadium and you walk over to one of the goal posts, and you pull a quarter out of your pocket, and you drop it by the goal post, and you walk all the way across the football field to the other goal post, and you drop another quarter there. If we took our solar system in the nearest nearby solar system, or we took our whole universe and shrunk it so our solar system was the size of a quarter, that's the distance away we are from the nearest solar system.

That comparison, is friendly to humans. Numbers aren't intuitively friendly to humans. What we want to do is put all of our communication into a context that is audience-focused. If we're talking to a computer, we can use really big numbers. If we are talking to humans, we should cut, simplify, and compare.

Nico Perrino: Yeah. We've done a little bit of that in the past in some of FIRE’s work. We work with college free speech zones. We don't have as many college free speech zones today in America because we’ve defeated most of them, but it used to be the case that one in six colleges had a college free speech zone in the United States. We would litigate against some of these free speech zones and some of them were just absurd.

One of the ways we would use to demonstrate the absurdity was comparing. It's like if the college is as a tennis court, a college or university is the size of a tennis court, the size of their free speech zone is a size of an iPhone. Or, would say that it's just one percent of the college campus and 99% of the campus is not a free speech zone. Or, we'd say it's the size of a parking spot. There was one unique case that we had at Texas A&M University. It's a huge school. Tens of thousands of students. We wanted to demonstrate the absurdity of saying the only place on campus that you can exercise your free speech rights is this one gazebo that they designated.

Greg got one of his friends from MIT to do the calculation and one of our talking points became if you want every student at Texas A&M University wanted to exercise their free speech rights at the same time, they would all need to be crushed down to the density of uranium-238. Nobody knows what uranium-238 is, but he's like they would need to be crushed down to the size of an element in order to exercise their free speech rights. It’s one way of just kind of creating absurdity out of it, so comparisons are always super helpful.

Bob Ewing: It’s memorable. In the Made to Stick book, they talk about the importance of being unexpected. You don't expect to be talking about uranium or crushing down the student body, so that helps to make it sticky.

Nico Perrino: Yeah.

Bob Ewing: I love it.

Nico Perrino: That's comparing. Simplifying. You have this great example in here and this might actually come from Starr and Heath. Here's the sentence. Thirty-four percent of white applicants and 14% of Black applicants without criminal records receive callbacks on job applications compared to 17% and five percent with records. Okay. Now, recite it. Remember it.

Bob Ewing: You know what? I actually went back to read this and I read it a few times and I still close my eyes and I could not recite it.

Nico Perrino: You simplified it, or they simplified it to this. White job applicants with felony records are more likely to receive a call back than Black job applicants with clean records.

Bob Ewing: That is a gut punch.

Nico Perrino: Very easy to remember, right?

Bob Ewing: Yes.

Nico Perrino: Much more effective to communicate what you're trying to communicate.

Bob Ewing: Yes. What's the big idea, and how do you bring it to life in a way that resonates with your audience? Cut all of the numbers and clarify the big idea.

Nico Perrino: Yeah. We already talked about simplify. You say read these three numbers and close your eyes and try and recall each out loud from memory. 3,948,583. 17 out of 33. 3.0423. Then, you said, now try doing the same experiment using these numbers. Four million, 1/2 and three. Right?

Bob Ewing: Yes.

Nico Perrino: What is easier?

Bob Ewing: It’s obvious. Yeah. Four million, 1/2, and three. I made those numbers up and even though I wrote those numbers out and thought about them, I’ve never been able to actually do that.

Nico Perrino: That’s messaging. Right?

Bob Ewing: Yep. I'll just add on the compare thing. Comparisons are hard. All of this stuff is hard and it's all gotten easier. Analogies are – David Hofstadter who wrote Gödel, Escher, Bach, he calls it the fuel –

Nico Perrino: I’ve been in his house before.

Bob Ewing: Are you serious? Well, we have to talk about that at some point because that's amazing.

Nico Perrino: Well, yeah, because he taught at Indiana University.

Bob Ewing: Oh, dude.

Nico Perrino: I went to Indiana University and he had a wife who passed away who was studying in a program in Bologna, Italy that I was applying for. He created kind of a memorial scholarship for that program for students from Indiana University who wanted to go to this Bologna full immersion language program. I was an Italian student. I ended up winning the scholarship.

Bob Ewing: Dude, that's awesome.

Nico Perrino: I ended up not doing the program, but when I won the scholarship, he invited me over and gave me this book with his signature. It wasn't Gödel, Escher, Bach. It was –

Bob Ewing: Is it Surfaces and Essences?

Nico Perrino: No, it was a later one. It was, I think, about something – I forget what it was called. It had crosses on the front or something. I remember the one thing about the book. I never got a chance to read it. I probably shouldn't say that, but it was like a 500-page book and he worked with the publisher so that at the end of every page was the end of the paragraph. You never flipped to the next page in the middle of a paragraph or in the middle of a sentence, which is very much like if you know him, it's like that might be something he wanted to try and do.

Bob Ewing: Yes. I love it.

Nico Perrino: Anyway, we can talk about that later.

Bob Ewing: I think there was some famous writer who took the opposite approach to writing, which was it might have been Hemingway, that would never finish a sentence at the end of a writing session so when he would start back up, it would be very easy to get started because I have to finish this sentence.

Nico Perrino: Oh, interesting.

Bob Ewing: Yeah. Yeah. Hofstadter calls analogies the fuel and FIRE of thinking. He says everything that we understand, we have to connect it to something we already understand to learn something new. We have to put it into a context that we understand. He says all of our thinking, whenever we discover new ideas, that process is analogical by nature and then analogies are so important to put into our communication, into our speaking, but they're hard because it's hard to come up with good analogies. Right? You want to tailor them to your specific audience.

Now, we have this incredible tool that's an analogy super making machine, and it's Chat. Before you go do a speech, you should absolutely toss in part of your speech to Chat and say come up with –

Nico Perrino: ChatGPT.

Bob Ewing: ChatGPT. Yeah, or whatever LLM you want and say, “Come up with five analogies for me that will bring my big idea to life.” Give them your theme, give them your proverbs, give them your stories, give Chat your specific audience and say, “Come up with some analogies for me.” That will help you to get started.

Nico Perrino: You know, it's interesting you say that because we're working on a case right now that's cert petition before the Supreme Court. Cert petition is essentially you’re petitioning the court to hear your case. It involves this case that involves this independent filmmaker who made a movie in a national park, an independent filmmaker. He filmed it in the national park. It was just him and a couple of people. They just set up a camera and took a couple of pictures. The National Park Service came after the guy, actually showed up at his place of business and turns, out, if you are making a film and you don’t get a permit and pay a fee in the national park, then you could be arrested, or jailed, or fined.

They have all these carve outs for all these different sorts of things that make no sense why some people need to do it and other people don't need to do the permit fee thing. That's neither here or there. The case went up to the DC circuit, which is an appellate court, and they upheld the permanent fee regime under the argument that sure, the film is First Amendment protected activity, but making the film, shooting the film is not.

They disaggregated the thing that's protected by the First Amendment from the process of making it. We were trying to talk internally about how do we communicate how absurd this is to people? We started thinking of some analogies. It's like Henry David Thoreau could publish his poems from Walden Pond, but he couldn't write them next to Walden Pond. That's a little too heady for people, so it’s like they might not [inaudible - crosstalk] [01:05:25] –

Bob Ewing: For a certain audience, that could be awesome.

Nico Perrino: Yeah, it could, but it's more like Picasso can sell his painting, but he can't take brush to canvas to actually paint it, or Beethoven could perform his symphony, but he can't actually write it out or something like that. You know, it's those sorts of analogies to make people see how absurd it is. Outside of the speech context, it's like, yeah, you can eat dinner, but you can't cook it. They're regulated in two different ways to demonstrate kind of the absurdity of the D.C. circuit’s opinion.

I want to close up here by talking about two final things that you like to talk with us about at FIRE which one is delivery and one is okay, so you've got all these things and how do you refine it, and how do you actually do it? One of the things you talk about with delivery is jazz over classical. Can you explain what that means?

Bob Ewing: Yes. Absolutely. The idea is in classical music, everything is written. Every note is written and then folks come out and perform that piece exactly. I got to see Itzhak Perlman with my brother at the Kennedy Center who's arguably the most talented violinist alive. Incredible concert and the music is totally written out in advance. It's a little different when you go to a jazz concert. They really intuited the music they're gonna play, but they never play the same song twice because in a jazz performance, they take the liberty to do what feels best in the moment and to connect with people in the audience, to connect with each other on stage, to do whatever they're feeling inside and to go different riffs.

It's not in a vacuum. There's a particular structure that they have totally integrated. We're gonna be in the key of C and we’re gonna move over to F. We know where we are and we're in a particular structure that makes sense and we start off, it's totally ingrained. The beginning is memorized, and it starts off this way, and we know exactly how it's gonna end, and we know what the structure is. Within the context of that structure, we bring it to life in whatever makes the most sense in that moment. You and I did not script out this conversation that we're having right now, but we've thought about it.

Nico Perrino: Yeah. We thought about a couple of questions we want to ask. We've kind of outlined it. We know the foundation of the conversation, what it's about, but we don't know which direction it’s gonna go.

Bob Ewing: Yes. If you are a military commander and you're giving a speech and one wrong word can start a nuclear war, then write a script and stick to it. If you're not in that context, then it probably makes more sense to play jazz than to play classical music or just to show up and ramble.

Nico Perrino: So, how do you play jazz? Do you write a couple of notes on a notepad? Do you outline the big themes you wanna hit and just talk about them?

Bob Ewing: Everyone should do what's best for them. This isn't physics algorithms, right? There's no one way to do this. There are people like Dan Kahneman, from Thinking, Fast and Slow, that need notes in front of them. They need to be looking at stuff while they're talking. There are folks like Salman Khan from Khan Academy who would never write out a script in a million years. He'll say, “I'm gonna come with a couple of bullet points, I’ll run a few reps, and I'm gonna go talk, and that’s how he does his thing. Then, there are other folks that write out scripts, memorize everything, and then show up, and then try to do whatever they can.

I recommend, I’d say it doesn't matter what approach you take so long as when you show up on game day, you feel like your message is clear in your head. When our thoughts are clear, then the words naturally flow. Paul Graham, the great venture capitalist –

Nico Perrino: Y Combinator. Yeah.

Bob Ewing: Yeah. He's awesome.

Nico Perrino: FIRE supporter.

Bob Ewing: Hey, that's because he's a smart man. He says that clear writing is hard because it's downstream from clear thinking. I would put clear speaking downstream from clear writing. The exact approach that you take doesn't matter, but the more we can clarify our thinking, the more the words will naturally flow. That's the hard part. Once you show up on stage, if it's a big event, you don't want to totally ramble. You want to say, okay. What are my proverbs, what are my big ideas, and what are the stories I'm going to use to bring them to life? Then, what particular structure am I going to put these into so they can best resonate with that audience?

Nico Perrino: Yeah. I gave a couple of speeches at the end of last year, one at Brown and one at Northeastern. They were on similar topics. I tailor them to each school, but Brown, I had this very detailed, it wasn't just outlined, it was like pulled quotes and facts and figures at this, that, or the other thing. I finished the speech and I felt like it was all right. I didn't get everything in that I wanted to get in. Before I knew it, my 35 minutes were up and I was like, “Oh wow.” Killer Mike actually had that problem at our gala too.

Bob Ewing: I got one more minute but I'm going for two.

Nico Perrino: Then at Northeastern, it was the next day. Something had come up here and I didn't have a chance to refine my notes or anything and I had realized that kind of the outline for this type of speech that I put together was far too long that I had to deliver it at Northeastern. I essentially just took my notepad and scribbled out some of the top lines that were on the notes for Brown and said, “Okay, I'm gonna to hit these five points. We'll see how it goes,” out of necessity just because I didn't have time.

I felt like it was one of the better speeches I had ever given. Unfortunately, it wasn't recorded, and I know that's one thing that you always recommend is at least, just voice memos on your phone or something so you can hear, and reflect, and improve and make progress. I learned that because I'm an expert on this topic, I don't need to create an expert on the paper as well. I just need to remind myself of the things that I want to talk about and maybe kind of the story I want to start, and the story I wanna end with, and the main themes I need to hit in between.

I learned from practice that that's the best way I give a speech. I just spoke at Kenyon and that's the way I did it. I got my five bullet points and 40 minutes later, the speech was over. It's like I don't need all these crutches.

Bob Ewing: Totally.

Nico Perrino: I just don't. I know the issue well enough.

Bob Ewing: Yep. The more clarity you have on it, the less you're gonna probably be bound to a script, and context matters. Let's say Will Creeley gave his remarks at the gala. He, I doubt, was spending his time reading from notes. He has internalized the stuff that he wants to talk about. You've internalized that. When Christina Martin argued her case before the Supreme Court on Wednesday, she had two minutes. You get two minutes before you get the Q&A. She had written everything out like, “Here’s exactly what I want to say in this context. This is really important.” The context matters and the individual people matter. I used to write everything out for stuff that I would do.

Nico Perrino: Same.

Bob Ewing: Then, 10 years later, I thought, “Oh my god. I could just show up and I have gone through this, and thought about it, and spoken about it so much that I don't need to be totally scripted.”

Nico Perrino: I did a talk out in California at some fancy high school, prep school and they did one of the TEDx things and I was TEDx speakers. You know with TED, you've got to be very refined and kind of work on things and distill them down. I ended up writing out a 15-minute speech and memorizing it word for word more or less. When I got up there to do it, the first 10 minutes go by great. The first 10 minutes, I'm kind of laying out the argument before I'm getting to the big point that I want people to come out with. There was a connection sentence or two that my whole speech kind of hinged on to transform from the laying out the problem to the solution and I just forgot it.

It's not like I forgot it in the moment. I can't even really explain what happened, but the point is, I wasn't really thinking about the speech. I was just going through the motions because I had memorized it. If I played jazz, I would have known because I was active and I was participating in the speech rather than just going through the motions. I would have realized that I didn't make that connection and I would have made it. From that point on, I decided I was never gonna memorize a speech because I need to be present in the speech and I need to connect with the audience, and I need to understand how my argument is going, not just with them but for me as well. Am I connecting A, to B, to C, to D?

Bob Ewing: Totally. Yeah what we say to our clients is however you want to do it, you have to push through the uncanny valley. What that is is when we normally talk, like we're talking now, we're talking in a way that brings our personalities out that's authentic. The problem with talking informally is we tend to ramble. The beauty of a structured speech is that we can add clarity without the rambling. When people start to do that, they go into what I call the uncanny valley where they become eloquent, but they sound unnatural and then, most people back out. What you have to do is push through and pop out on the other side where you could become authentic and eloquent. That's the goal.

Nico Perrino: Yeah. One of the ways you get to that goal is practice. You guys are so big on practice –

Bob Ewing: Of course.

Nico Perrino: – and listening to what you have done. When I said I forgot to put the voice memo on, it's like Bob Ewing’s in my ear. I should have done the voice memo because I thought that was a good speech. Let’s listen back. What did you like about it? What made it good? Also, soliciting feedback from people honestly, not just negative feedback on what could be improved, but what you do well so that you can lean into that in the future. I don't know that there's any extra point on that. I think people understand intuitively that that's an important step in the process.

Bob Ewing: Yes, but no, most people don't do it. It should be absolutely part of the presentation. There's a saying in rock climbing that when you get to the top, you’re only halfway there. All growth happens in the stretch zone and if we want to get better at stuff, we have to iterate based on feedback. There's a great quote from Naval Ravikant. He says, “It’s not 10,000 hours that leads so to excellence. It's 10,000 iterations.” That's how all progress happens in our universe. That’s natural selection, that's why markets work, that's how engineers build stuff, that's how science works and that's how skill development works is we iterate based on feedback.

So, if you say from now to the moment that you're going on stage, it's not about logging as many hours as you can. It's about getting as many iterations as you can. That's what you need to do, and the better your iterations come, the better your feedback is. Feedback from self, feedback from others, feedback from the world around us, iterate, iterate, iterate.

Nico Perrino: Yeah, and you can build things into your presentations and into how you assess them so that you can generate good feedback as result. You can go to someone in the audience and say, “Hey, can you take some notes on what you think is working and not working here as you're listening?” You can turn on your voice memos. As you said, this is how they do it in engineering. When the starship blows up in space, that's a learning opportunity. How do we iterate on top of this next time so maybe it gets higher or who knows, it gets to orbit and is successful, or we don't blow up the launchpad?

Bob Ewing: Yes. Most people do not give good feedback. We tend to be assholes to ourselves and then we tend to be really kind to others in front of them, and then we go in private, we tend to tell ourselves we did better than we did and we tend to be critical of others. Good feedback is honest, it’s specific, and it’s compassionate. We say to ourselves, “What specifically did I do well and what specifically can I do to take it to the next level?” and we do the same thing for our colleagues. The better we can get at that, the quicker we grow.

Nico Perrino: We're closing here. Are there any speakers that you admire, who you're constantly coming back to and saying, yeah, this person knew how to get a message across?

Bob Ewing: Sure. Yeah. As a general rule, I recommend to people to look at the best entrepreneurs and the best stand-up comedians that really resonate with them. I think those genres in general produce the best public speakers.

Nico Perrino: Can I also say I did a stand-up comedy class at The Comedy Cellar when I was living in New York city. I work in the communication space and the best writing training that I’ve ever gotten was taking that class and learning how to write a stand-up comedy joke. Really, the setup and punchline, just generating that and condensing your joke down to get as many laughs per minute as possible, you're just forced to kind of remove all the bullshit, and all the throat clearing, and get down to your core message and the stuff that's really gonna resonate with your audience. You have feedback from your audience immediately. They either laugh or they don't.

Bob Ewing: Yes. Yes. It's real feedback.

Nico Perrino: You start to figure out what your message – yes.

Bob Ewing: That's the universe giving you genuine feedback.

Nico Perrino: It is. I would just, I guess, say, “Yes, and…”.

Bob Ewing: Exactly.

Nico Perrino: Look at stand-up comedy and maybe try it yourself, just writing some jokes.

Bob Ewing: Yes. Speaking’s a skill, but you get better at it by doing it. You don't get better at speaking by reading books. You get better by going out and doing it and then getting feedback. If I had to pick a top public speaking guru or someone that resonates with me the most, I would say I'd like to go back in history and say who were the best speakers of all time and read their speeches. William Safire has compiled hundreds of the best speeches ever. If I had to pick one person, I would say you and Killer Mike were just talking about Frederick Douglass, one of the great icons of free speech and great advocates of free speech, and you talked about his Boston speech.

The piece that resonates the most with me with Douglas is actually something that he wrote, and 10 years after he escaped slavery, he wrote a letter to his former slave master, Thomas Auld, and by background, Thomas Auld is someone that he said made him feel like degraded chattel and made him tremble. Whenever Frederick heard Thomas's voice, he would tremble and Douglass was a big, strong guy. At one point, he tied Frederick's cousin Henny, a small, crippled girl, to a post and beat her until she passed out and bled, and hours later, he came back and beat her again. You can imagine the context in which Douglass is writing this letter 10 years after he escaped.

He writes this letter, and I like to say to people, “If you were Frederick Douglass, what would you put in that letter?” Everyone should read it. This is basically how. First, he brings it to life with stories from his life and that's what we should do. The letter is full of stories from his life. This is how he ends it. He says, “Thomas, you are always welcome in my house. There is no roof under which you would feel more safe than mine. There is nothing in my house that if it would not aid in your comfort, I would not readily provide you.” Then he says, “I would esteem it a privilege to show you how human beings ought to treat one another.”

When I read that, I'm like, “Oh my god. That's it.” If he can transcend outrage, then certainly, we can. Righteous indignation, we see this so much on social media because it primes us to engage in System 1, anger. If we can pull back and say, “Okay, I'm going to try to think through what I'm going to say, or maybe I have to write out everything.” I have to write one Substack piece a week instead of write 100 Tweets are angry. I have to have one thoughtful piece. That's a huge deal. The thing with Douglass is he's showing us with clarity and compassion the correct path forward.

Nico Perrino: He's making it impactful by laying out all the atrocities at the beginning, right?

Bob Ewing: Yes. Yes.

Nico Perrino: If the punchline, and it's hard to even use that phrase in the context of such a visceral and terrifying letter, if the punchline is “I'm going to offer you all the comforts of my home and nobody would be a more welcome guest than you in it,” if you want that to really resonate with people and to understand that this is the way we defeat the hatred in our world, you begin by demonstrating all the examples of hatred that this person laid upon you in their life. Then, it's like this misdirection.

You're expecting, as most reasonable humans would today, that Frederick Douglass is gonna lash out and use the opportunity to get revenge but then he doesn't. That's what makes it so powerful is he does the kind of sort of Christ-like thing and grants almost forgiveness at the end.

Bob Ewing: Yeah. Showing with clarity and compassion the correct path forward. That's it. It doesn't matter how people treat us. We always have the freedom to choose how we communicate and how we speak, and how we speak matters.

Nico Perrino: Well, Bob, I think that's a good place to leave it. I really enjoyed this conversation. As I said, much of what we do here at FIRE was inspired in part by kind of the lessons you gave to me early in my career, so I want to thank you for that. I just urge any of our listeners who are looking for help in developing their message or their public speaking to get in touch with you and Maryrose and your colleagues over at the Ewing school. What's the URL for that?

Bob Ewing: and

Nico Perrino: You own both. Very good. You’re, of course, the founder and president over at the Ewing School and it's been such an honor and a privilege to get to work with you, and Maryrose, and your team in developing some of our speeches here at FIRE, including the gala speeches that you mentioned before. Greg and Will both worked with you and your team in developing those, so Bob, thanks for coming on the show and hopefully, we can do it again sometime soon.

Bob Ewing: Absolutely. Thanks for having me.

Nico Perrino: This podcast is hosted and produced by me, Nico Perrino, recorded by my colleague, Tyler MacQueen, and edited by my colleague Aaron Reese and Ella Ross. To learn more about “So to Speak,” you can subscribe to our YouTube channel, which will be linked here in the show notes. We're also on Instagram, Facebook, and Twitter under the handle freespeechtalk. You can also like us at Facebook at We take email feedback at If you enjoyed this episode, please consider leaving us a review on Apple Podcasts or Google Play. Reviews do help us attract new listeners to the show, and until next time, thank you all for listening.