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Billionaires live in a different reality — but that’s no reason why you can’t connect, communicate, and collaborate. This week Paul and Rich share tips for successfully communicating with the wealthiest leaders. They explain the importance of keeping it simple and why billionaires often respond with gusto when you tell them what they shouldn’t do.


Paul Ford You on a yacht is an absolute nightmare. Like I don’t even want you on a yacht, ever.

Rich Ziade Me?

PF No! You’re just gonna be like ‘what the hell–all anybody wants to talk about is boat stuff and the Wifi is 1.5 kb/second.’ [Rich laughs] You’re setting up Raspberry Pis on the yacht. [music ramps up, plays alone, fades out]

PF Richard!

RZ Paul.

PF Hey, how you doing?

RZ Listen, there’s this weird, weird phenomenon consulting. 

PF Okay…

RZ We’re not gonna talk about consulting. That’s not what this is gonna be about. But, what I’m about to say is gonna launch us into a whole other conversation that is universal in scope. 

PF Nothing I would like more right now than to just be launched. 

RZ You ready?

PF Yeah, I’m ready.

RZ The smaller the deck, the bigger the budget.

PF Oh yeah, yeah this is a classic. This is a big one for me. The way I learned this was I got called over to a giant publishing company. And it was like ”you’re a writer” I was like ”yeah, sure I am!” You know, all confident. They were like ”we need you to go talk to this head of HR, C-level person, giant company, and help her get her presentation done.” So I go over and I’m ready with my bullet points and my thoughts and I’ve looked her up and I’ve got my plan. And she shows me the deck and it’s literally like a picture of the White House with the word ‘power’ on it. I never seen anything like this before where corporate messaging was reduced to one word at time. It’s all risk otherwise.

RZ I want to peer into the mind of the billionaire. Okay?

PF In general. I’m against this. I think we all think too much billionaires. And people worry too much about other people’s money.

RZ No doubt about that. No doubt about that. I’m not saying let’s get some tips on how you can become a billionaire. I’m not suggesting that. I think billionaires are weird. There’s a few characteristics that jump out at me. I think the human mind at some point can’t wrap it’s head around wealth once you cross a certain point. I don’t think it’s wealth anymore. It becomes things like that person meets you in Aspen and you walk up to them and say what about yesterday before we think about tomorrow. And then the billionaire says ”oh my god, you should be managing my charity.” Like they get to such an abstract place that the words chosen–and there are people by the way who know how to deal with billionaires, they actually, people who are really great at fundraising, people who are really great at managing relationships of really wealthy people, understand the importance of very few words. Because their heads are fully scrambled at that level. And first off, they’re bright. Most billionaires, except for the ones that inherited their money, got there because they’re probably outlier bright. Like let’s just say that out loud.

PF This is critical to understand. I mean A, everybody kinda knows that money creates more money. Right? So there’s that. But I think it’s also just like, money isn’t that complicated. Like these are people who just took, they’re bright, they’re smart, they put all their energy towards making something, they got a lot of money, and now that money is just gonna make more money. It’s all set up for that.

RZ And there are characteristics, right? There are weird–like Steve Jobs was a weird guy. Like that’s not a guy that really sought wealth. He was just very driven and very particular but he was also crazy. Right? He would yell at you for bringing the wrong salad to him. Like berate you in front of the staff.

PF Oh god yeah.

RZ He was that guy. 

PF Oh, just you know, wire your shoes yellow!

RZ Exactly. So like there’s an eccentricity that’s kind of consistent amongst them. I mean, when I heard Bezos was making like a clock, I think there’s a clock in the side of a mountain or something.

PF That’s the Long Now foundation. It’s a 10,000 year clock buried in the West, and lets us think longer term.

RZ Right, exactly. But But the idea of a billionaire saying, Oh my god, I have to do this. I need to take two weeks off somebody else from Amazon. I need to think about this clock, tells you a lot about how they think and the things that tipped them off. Like the things that light a fuse for them are very unusual and strange, right? Like they’re not, there’s no such thing as that as the down to earth, like sort of just he’s just really looking forward to reading this book this weekend billionaire. Isn’t like Larry Ellison, isn’t he like into Samurai outfits and swords and shit?

PF He’s had any new his outdoor shower is made from many ton boulder. So you’ve got that going on there. I just, I think that these are people for whom a lot of stuff has become an abstraction, right? Like, first of all, you can’t trust human relationships anymore, because you have this huge moat made of money between you and everyone else. So there’s that Second, the things that interest you, you now can actually exert real influence over. I like writing, I’m going to find a college. You can do all these things. And then you’re like, well, what am I going to? What am I going to do? And, you know, it’s interesting to me I what I’ve observed, they all start to live out. And it’s mostly men, their boyhood fantasy. So it’s like, space is cool. The one who is the most interesting is Jeff Bezos, his ex wife, who literally went, Wow, I have an absolutely unbelievable amount of money after this divorce. I think she married a dude from her kids school. And then she gives the money to the most obvious charities possible and says go to, I don’t need a lot of reporting. And so it’s like, for her, she’s like, I gotta get this out of here. It’s too wacky. For her husband. It’s like, I need to fly a space phallus into orbit.

RZ I want to share another observation, which I think is relatively consistent amongst really, really, really, really outrageously wealthy people. Because and this doesn’t apply to billionaires. It applies to a lot of people who are absolutely singularly focused with a goal. And the example I want to, I want to highlight here. I was in Miami, just spending a weekend and I had some, some work related stuff. And I happened to be there during and this is a fascinating world, Paul Ford, we are not on in this world. We are successful people. We don’t, it was a yacht festival. 

PF Ah, yeah. So I started to peer into this world, not because I want to not envy or anything, I was just fascinated at the society that was built around this. Because these some of these yachts were like the mega yachts, like the 300 meter, whatever like these are, you know, they’re 100 million dollar and up yachts. And I learned something. I learned that they don’t make them. You don’t just make the yacht, you don’t order the yacht and make it. It’s actually a project. It’s this really engaging relationship. It turns out with the buyer, where the goal is this outcome, and they’re going to talk to you throughout, it’s actually collaborative, and there’s nothing but success at the other end, because it’s this amazing boat that’s going to be built, but the actual offering, the service, they’re offering you his satisfaction, so that you can feel like you are moving forward towards this thing, because billionaires are absolutely wired towards not failing and having the perfect outcome occur. So they have literally this world, they create a world because the y’all it’s gonna take a year and a half. And they love that one hour meeting once a week where they’re showing them the path.

PF That is exactly right. Let’s pick, we need to pick the table for the forecastle.

RZ All of it. You know, they say it’s 150 million, and it ends up 250. Because of that the person’s decisions, right? They keep caking it on. And this is I want to translate this to advice because this is a weird topic we’re touching on, is when you are talking to people further and further up the chain, right? Walk back from outcomes. They are fully wired, fully programmed to think about outcomes. And then they run the scenarios and the risk and they navigate the risk and they look at the investment required, but talk outcomes. That one page memo isn’t some poem that they sign off on, then they hand you 10 million bucks to do a project, that one page memo is a state of the world that you are promising them, and then they’re going to interrogate it, let them interrogate it, but start with the state of the world, start with that outcome.

PF And this is the thing like the 3d model is what wins, right? The walk through, the shiny stuff. 

RZ Oh, yeah. I mean, let’s take it to Postlight. Here, like we are big advocates of creating artifacts that are rich that you can touch, forget the power of the PowerPoint doesn’t cut it. If you’re looking to persuade and you’re looking to gain, like real political momentum.

PF We should be clear for our audience, like you’re thinking about this, we’re talking about it. But this is actually not a firm, optimized to serve billionaires. We’ve had people of unbelievable wealth come through. And we, I mean, we do fine, we do their work. But the kind of attention and focus that you’re talking about, we don’t build yachts, we make the product and it drives some revenue, and it’s good and it’s solid in the works. There is a whole nother world of selling where you’re going up that level, where if you take six months to get that one architectural rendering done, and they pay you along the way or not. That’s the level that they’re expecting.

RZ Yes. And they expect you to value their time such that you are putting forward a particular reality. Anxious, wealthy people, anxious leaders in companies, anxious executives, is just gold for our world, for the consulting world. Why do you call a boutique consulting firm like McKinsey that charges you outrageous amounts of money? It’s because A, you have money to spend and B, you’re anxious. You need to see a path and they want clarity and they want real commitment to that path. I always try to talk people out of option A, B, and C, because that’s not a path. That’s you’re giving them work now, and they just want the best option put in front of them.

PF People at that scale, they want better than next door.

RZ Yes. I mean, you’re talking about the competitive aspects of this too, right? Which is–

PF Not to say like, I want my–look, I’ve already seen what a really nice boat can look like, mine should be one foot longer. It should have a chrome trim. Because why wouldn’t it? I’m amazing, right? And it’s like, the same is true of my strategy for expanding the franchise in South America. It should be a little bit better.

RZ You know, and this is the hardest thing to teach when you’re communicating to decision makers and leaders and people who have a lot of control over the levers. Probably one of the hardest things to teach, because it’s not really a teachable thing is how much they value, a strong voice in the room and an assertiveness and a conviction around the path, right? They’re brutal. Bezos is legendary for just cutting people to pieces as they’re trying to put forward a plan. But they want you to defend it. Because they’re looking for a little bit of themselves in that advocate, right?

PF They’re so bored. They’re just so frickin bored. If you look at Jeff Bezos is incapable of feeling any kind of stimulus short of being shot into space by a rocket at this stage in his life. Yeah, he there is nothing left for him to conquer. He doesn’t want to be the president of the United States, right. I mean, Mike Greenberg did, right. But like, he doesn’t want to. Like these people it’s just, um, so it’s like, well, I guess I go into space, really, I got a life ahead of me. Do something fun. And you’re in there and you’re like, I want to tell you about the q4 numbers and where we’re gonna go with cocoa beans. And he’s like, I died two years ago, listening to you.

RZ I need to ask you a question, Paul. I need you to honestly and openly. I always thought Elon Musk was a kook, what are your views of Elon Musk?

PF I have a very conflicted set of views. First of all, Elon Musk on Twitter is one of the worst things that’s ever happened in human history. Just garbage. [Rich laughs] Just crypto and nonsense. And he’s like, he acts like an edge lord, and he’s got to be in his 50s now or his 40s. It’s just very Bay Area.  And also, like, you know, this guy, he’s sort of like the, it’s the Steve Jobs thing in that, like, what does he really do? Right? Like, he just creates an environment probably by annoying everyone so much, that an unbelievable amount of stuff gets done. Like he just is so annoying, and he clearly gets into your head to such a degree that you eventually go, I will make a rocket land on the ground while still standing straight up. He’s a fantastic risk taker. And here’s the tricky part. He is a capitalist bullshit artist, there is no way around it. But the work he does around climate, around batteries, around sustainable energy, etc, etc, etc. is very significant. There is no way around it. And then you see the cybertruck and you go like, is this guy just completely dicking with us? Is he just thinks we’re idiots like, you know, this low poly nonsense that we’re going to have. And here’s, I have tried to block Elon Musk’s name from Twitter. I’ve tried to lock him out of my life. And escape that guy. He is absolutely and then he’s on SNL. You cannot escape Elon Musk.

RZ So here’s what were my perspective on him has evolved. I used to think he was kook and I found him kind of annoying. And I agree with you. The social media stuff is kind of dumb. But here’s–is Elon Musk, a genius? Is Steve Jobs a genius? Doesn’t have to be, but they share a very particular characteristic, Paul, and this goes back to my point earlier. They state an absolutely preposterous future state and tell people we’re going there. And know how to activate really talented people to believe something that they probably shouldn’t believe in at the outset.

PF It doesn’t always work right? Like it worked with the Mac, they got the Mac across the line in 84. And then Steve Jobs went to Next and said I will we will have a factory floor. Everything will be perfect, everything will be flawless. And until Apple bought Next it was going to die. The other thing that you’re missing is what I think of as hitting the sheet metal with a hammer every two hours, which is something that these people are excellent at doing, which is like, oooh, it’s been 119 minutes, bring me my sheet metal in my hammer, and then they just hammer it until everyone runs to see why there’s an enormous, loud thundering noise coming from the CEOs office.

RZ It’s enormous pressure. You can be brutal and not really managed with love but rather with fear. But if you’re aspirational and you’re promising them that they are going to be connected something that is elevated. And is going to change the world. You bring things out of them that you otherwise couldn’t. Dictators and cult leaders do this for all the wrong reasons. The characteristics of a Steve Jobs, to be brought an iPad, and say this is really great Congrats. But guess what it needs to fit in my pocket, go back. And then they had to toil away for another year. Most people don’t know that the iPad predates the iPhone, you are not going to get dad’s love. It’s always just beyond reach. 

PF You’ve identified the particular kind of like sociopathy, that’s fascinating, which is, I’m going to make a decision right now, that will cost this person a year of their life. And it could fail. And I don’t care. I wish them well, because I pay their salary. I can spend their time as I will. Hopefully something good comes of it. And then I’ll take the credit, but they can put it on their LinkedIn. And that dynamic is like that is a specific kind of human being.

RZ It is a specific kind of human being. But that kind of human being is using that charisma to align enormous talent and resources to just give something a go, right. Usually, that kind of personality is aligning humans and resources for power. 

PF This is where billion comes in. Right? Because the people who do that spend unbelievable amounts of treasure, and are okay with getting nothing in return. 

RZ Of course!

PF Like, Elon Musk has burned so much money. Why is he successful? Well, he understands what he’s building. He has a good sense of technology. He’s charismatic, he will get people lined up. He drives everybody crazy. And they want to please him. And he will spend ungodly amounts of money to get the thing that’s in his head. Other people’s money, of shareholder money. To get the thing in his head into the world.

RZ Yeah, I think that is a pattern. You know, I watched that creepy NXIVM–

PF Oh yeah, yeah.

RZ And you knew that that guy, he’s kind of this little bullshitty weasel. He’s essentially like a just a management coach who figured out how to make a cult in Albany. By the way, I don’t know what’s worse, the cult or the fact that it was near Albany. It’s almost like a double hit. 

PF Yeah, but if you start a call in New York City, you have a lot of competition. Albany’s good. Rochester would have been good. [Rich laughs] If I was gonna start a cult, I’d do it in Buffalo!

RZ But you watch that, and you’re like, if this person was interested in mobile apps, they would have been a billionaire. You can just see the ingredients are there. But the motivation and the interest in the technology just wasn’t there. You know, why are we talking about this?

PF You got to tell me, ’cause you’re like, let’s talk billionaires. I’m like, alright, what brought this on?

RZ Look, as someone who spent a good amount of their time as we grew Postlight, and my old agency, essentially trying to persuade people who had their hand on the power levers to do something, I think I’ve learned a lot about A, how they think, and that’s not. And those characteristics trickle down, and B, how to communicate with them, and how to position yourself as you communicate with them. And to get them from point A to point B. People talk about, you know, sales tips and persuasion techniques and whatnot. And it’s very particular and you the further you go up the chain, the weirder it is the the more counter intuitive it is.

PF I gotta tell you, I don’t talk about this very much. But like, yeah, I have actually worn personal relationships with a couple of ultra high net worth individuals. And I have been in the room with very, very powerful people, probably, I don’t know, 10, 20 times in my career. And it is a different kind of experience. So I mean, let’s talk about it, you go into that room. And then first of all, there’s a lot of people attending. There’s just a lot of humans usually who are nearby. Now, I’m not talking about just like executive assistants, but like, ultra high net worth individuals tend to like a lot of people around them. That’s just part of it.

RZ People I think they who they’ve come to trust, I worked for, I reported directly to a billionaire. And he used to drag me into meetings that really weren’t in my purview. I was Chief Product Officer. And he’d say, come to this meeting. And I’m like, why am I in this meeting? And the only reason I was in the meeting is when the meeting ended, he asked me to stay for five minutes and asked me what I thought. And that’s it.

PF But it’s but again, your what’s your time, your time, he doesn’t have to explain why he wants you time. He wants to just move you around. You are a factor. You are a unit for him. He’s hoping that you’ll get some inputs and you’ll come up with an interesting output five minutes of his time. On to the next thing. I’ll tell you what people do a lot, which is, here’s what I’ve noticed people think about ultra high net worth individuals a lot. They tweet about them. They get angry at them, they internalize them, they worry about what it’s going to be like to meet them and so on.

RZ Why do you think that is? Is that envy?

PF That is just humans look up and go what either, why not me? Or how do I get there? That is absolutely just human behavior. Right?

RZ I have neither of those characteristics. I am fascinated by them from an anthropological sense. And from a communication sense.

PF I can tell you too, we had somebody come by the office once who had had an enormous outcome from the company. And they spent the whole time telling us how toxic and poisonous it was and how miserable they are. Just like, you know, there’s another billionaire, there’s a lot of that, too. Here’s the thing, you can’t have a relationship, or prove in the short term, that you are special, because the next person on their list is like a Dean at Harvard.

RZ Don’t try to win anyone over.

PF No, they have access to every single brain in the world, because that’s what money buys you. And if they’re smart, they enjoy that part of it. Right? All you do is like state your case, if there’s something they can help you with, you ask, and if there’s something that you can help them with, you offer, you kind of expect to get dismissed. And you know, what’s funny is you actually have the same relationship when you’re on the media. I remember when I used to go on the radio a lot. I would talk, they’re done with you. The host is warm, and they’ve brought you in and they’ve had a beautiful conversation, it had gone really well. And it’s like, click and you go anything else? They go, no. And it’s someone else’s voice. It’s like some intern and they’re like, no, thanks, Paul, click.

RZ Zoom out of billionaires. This isn’t about billionaires, what you’re talking about the advice you just gave, right, which is don’t promote yourself, in those moments, when you’re talking to people who are influential, whose time is limited, who just have access to everything. That’s a lot of people, there are plenty of executives in plenty of companies who are exactly in that state. Don’t go in thinking about you and how you’re going to increase your perceived value. Don’t bother, go in there, lock into their paranoia and anxiety, everybody, and believe me, the higher up the chain you go, the more twisted and anxious they actually are deep down.

PF Let’s go back to your original point, right, which is not just billionaires, but media people, powerful people, people who run this show, the Dean of the College, the person who runs the large, the large NGO, the head of the foundation, okay? They have a lot to do every day. And they’re very bored. Because they do the same things over and over every day, they’re going to come in, you’re going to come in there, and you’re going to tell them why you are the answer to all of their problems. And they hear that 20 times a day. And in fact, they’re experts in filtering it out, because that’s what everybody does, because we’re all human, everybody wants to get in there. All you got to do is go in there. And you know, there was a piece of advice, someone who had to present a Bezos said, you know, you just cut every other slide out. So he has to interpolate between in the deck, right? Like, that’s actually a ridiculous concept. But don’t fill in the blanks. One number, two numbers,

RZ I’ve landed some very, very large deals for postflight. And I’ve been in the room with some very, very influential, like people who have a lot of influence and have a lot of sway, I have one consistent piece of advice to share, they really value it, when you warn them not to do something. Because what you’re telling them, they these people got to where they are, whether it be decision makers, executives, wealthy people, whatever it is, they got to where they are, because they really are tuned into avoiding danger, to avoiding risk. And when you give some time towards what they should not do, and why they should not do it. And if you feel strongly about it, and emphatic about it, you just want you just gained another few meetings of time.

PF Something really specific there, which is that when you’re dealing with somebody with a lot on their plate, and I think billionaire is to focus, right, like just somebody who has a lot going on, they’re getting sold hard. They’re an obvious target. Their name has a title. And so people who have platforms, ideas, buzzwords, are hitting them hard. And in fact, all that stuff comes pre packaged. And it comes in the form of expensive consultants saying what’s your blah, blah strategy and making that people love to put them back on their heels, they love to present jargon. And they’re in a position where they can either go, I guess I’m an idiot who doesn’t know about that, or they can go I don’t know, why don’t you tell me what my strategy is? People are really good at getting them positioned that way. Now, you’re going in there and you’re saying like, oh, man, yeah, I bet they’re eating you alive. I bet it’s like mosquitoes with digital transformation. And they go like, oh, man, and they laugh. They go, you have no idea. You know, and you go, now, frankly, I probably don’t. But I will tell you that what I see is really happening. It looks like this. Where’s the money? Where’s the power? Where’s the influence? Where’s the growth going to come from? It’s real simple stuff. And then they’re trying to think who if I want to do this, it’s also worth like, what are their thoughts? Their thoughts are if I want to do this, who’s going to do it? It’s not that’s a good idea. It’s that sounds interesting. Can I take Sally and I can I move Sally out of where she is right now and put her on to this instead? Yeah, because the thing you care about your discipline, the metrics you care about doesn’t matter, doesn’t matter.

RZ You know, this is universal advice. One is, be emphatic, and tell them clearly what they shouldn’t do, what they should avoid doing and why they should avoid doing it. And to give them clarity around that outcome. And a path to getting to that outcome without too much information without too many options, put in front of them without option A, B, C, D. Because that speaks to conviction. They’re where they are, because they are smart. And they’re going to read the room very, very quickly, right. But what you’re doing is you’re giving them clarity.

PF You know, the other thing here too, is you can spend all your time saying I don’t have the right clothes, etc, etc. They don’t care, you’re only in that room, if you’re supposed to be.

RZ So true.

PF And they don’t care. They don’t care.

RZ They patronize people in strong positions.

PF Don’t go out and buy like a $75 tie. Because you only have $50 ties.

RZ It’s not gonna move the needle. [Rich laughs]

PF Like if you’re like me, if you’re kind of like a schlubby guy who gets lost in his own head. That’s why they called you don’t pretend to be otherwise. Oh, the other thing I’ve noticed people, when they interact with this part of the world, they tend to have little like, Cinderella fantasies. But no, you’re going home at the end of the day back to the same apartment, you’re going to eat the same dinner. This is something to know, and this is really important. Ultra high net worth individuals or extremely powerful individuals are unbelievably good at taking your time and really not giving you a lot in return. Like, god bless them. Because you’re gonna go in there and go, this could be it for me, oh, my God. And there’s a little bit of a vibe around them, because that’s how they get power. They get power by everybody thinking that they have a magic wand, right? But they’re not going to give you $2 million, because you had a fun idea. And then or if they are they’re going to take 35% of your company.

RZ Totally agree.

PF Should there be billionaires, or should we tax aggressively? 

RZ Fine. Yeah. I mean, they’re, you know, wealth concentration has–I believe in free markets. I believe in America driven systems. I’m the American dream. I came here with nothing and was able to do stuff and but–

PF It’s a little out of whack, right?

RZ It’s a little out of whack. You can have the debate about whether, you know, did I want government to redistribute Bill Gates as wealth do I prefer the Bill Gates Foundation distribute Bill Gates wealth? You can have that debate.

PF His soon to be ex wife is definitely distributing quite a bit of as well right now, too. So there’s that?

RZ No, no, no. But I guess I guess what I’m saying is, do I think foundations are going to do a better job than governments around climate change? I don’t know. I think they’re necessary. I think, I think we need a little bit of both. Are things out of whack? Things are out of whack. That is real. You and I have done extremely well. We are in the middle of the pack. They’re just, they’re like 30 people who have an absolutely preposterous outsize proportion of the wealth of the world in their hands. And it’s kind of comical. So, that’s where I am. Anyway, I do think this is universal advice. I do think this is, this is advice around anyone who’s trying to convince anyone else who seems to have just a tad more power than they actually do. And how do you get that person there? And you know, the days of the drink, I’m gonna take you out for a drink and schmooze you or get you, you know, a skybox seat at a ballgame. I feel like that’s, that’s still part of the process. But man that doesn’t cut it. Right. We’ve learned that that doesn’t cut it.

PF Look, I mean, if this is the world you’re in, and you success should be measured by, do you get an email twice a year saying, Hey, I have some questions for you. That’s about it. That is success. 

RZ That is great success. 

PF Any closer than that, and you get ready. That’ll blow your world up. My number one rule for this world because I’ve interacted with a bunch is don’t worry about other people’s money.

RZ Man, that is such good advice. 

PF Yeah, yeah. I mean, you can have big structural thoughts, but the amount of time and energy we spend on Jeff Bezos, Jeff Bezos isn’t going to give his mind to you the way you change the Jeff Bezos’ of the world. Yeah, we legislate a different taxation plan. And if our government doesn’t want to do that, that’s the problem. We focus too much on the individuals. Now granted, it’s a little tricky with Mark Zuckerberg and you know, the influence that he has over our economy and over our discourse, but then again, he got on that weird surfboard thing and carried the flag. So you know.

RZ All was forgiven, man.