Episode
106
March 13, 2025

Donald Trump

Transcript

Karl Marx famously quipped that history repeats itself.First is tragedy and 2nd as farce.But what if he had it backwards?Because, at least in the case of Donald Trump, it started as farce and only became real afterwards.Donald Trump.

0:15 Just last week he confirmed the National Review that he is again considering a run in 2016.Do it, Just do it.Look, look at me.Do it.I will personally write you a campaign check now on behalf of this country which does not want you to be president, but which badly wants you to run.

0:37 And then ofcourse, there's Donald Trump.Donald Trump has been saying that he will run for president as a Republican, which is surprising since I just assumed he was running as a joke.Knowing what we know now about how he has become president twice now, it can be difficult to put ourselves back in the mindset of 2015 and just remember exactly how far fetched his presidency seemed.

1:05 OK, here we are.And which Republican candidate has the best chance of winning the general election?Of the declared ones right now?Donald Trump.President Obama will go down as perhaps the worst president in the history of the United States.

1:27 Exclamation point at real Donald Trump.Well, at real Donald Trump, at least.I will go down as a president.And then, seemingly for no reason, everything changed.

1:44 Thank you.And tonight, Donald Trump is celebrating his first official victory of Campaign 2016.Poll says Donald Trump has taken a slight lead over Hillary Clinton for the 1st.Time and those are states that Clinton was supposed to win, was supposed to win Michigan, Pennsylvania, Wisconsin.

2:00 DNA projects Donald Trump will carry the state of Florida.CNN now projects that Donald Trump will carry the state of Wisconsin.Have a major projection.CNN projects that Donald Trump will win the great Commonwealth of Pennsylvania.

2:17 They're going to make this decision now.The Fox News decision desk has called Pennsylvania for Donald Trump.This means that Donald Trump will be the 45th President of the United States.

2:35 Sorry to keep you waiting.Complicated business.Complicated.So today we are talking about Donald Trump, who he is and what motivates him.Who is this guy and how did we get here?Find out now on how to take over the world.

Hello and welcome to How to Take Over the World.

3:15 This is Ben Wilson.Today we are talking about the guy Donald Trump.Maybe you've heard of him.Why would I do this episode about Donald Trump?Do I want everyone to hate me?No.The reason I wanted to do this episode is he is unquestionably a great man, one of the greats.

3:34 And that's not an endorsement, Neither is a condemnation.It's not a value judgement at all.He just is one of the great men of our lifetime, certainly one of the most powerful.His life is fascinating.And he's a symbol of this new mantra going around that you can just do things.You can just run for president with no experience and start the largest and most powerful American political movement in 100 years.

3:55 And let me just preface this episode by saying I know that many of you are not going to like it, both from the left and from the right.Donald Trump is probably the most polarizing figure of all time if you just take into account the sheer volume of people who have strong opinions about him.I would guess the upwards of 80% of the world, of the 8 billion people that live on this planet, either love or hate, have strong feelings in one way or another about Donald Trump in this episode, again, is not to tell you he's good.

4:22 It's not to tell you he's bad.I just want to get at the man Donald Trump, who he really is.What are the strategies that he has used to rise and become the most powerful man in the world?Because this is truly is a surprising and exceptional story.So let's get into it.This is the life of Donald Trump.

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5:51 So it's great.Go to Van Man dot shop.Use code takeover 10 to get 10% off.You won't regret it.I love everything they make.I can't recommend it highly enough.Go to Van Man dot shop.Use code takeover 10.OK, so let's start off talking about where Trump came from.

6:09 And that means talking about his father, Fred Trump.Because that relationship is one of the most important in Trump's life.It really formed him.So who's Fred Trump?He comes from a family.His parents immigrated to the United States from Germany.And he started out as a he was a genius, frankly.

6:25 He's very, very smart.And as a teenager, he learns a bunch of trades.He can, you know, do the plumbing and the carpentry and the painting.He can do everything to make a house.He learns all these trades.And so then he starts building his own houses and selling individual houses, and he keeps doing this and saving up a little bit of money.

6:44 And then eventually he's able to build entire neighborhoods, entire developments, as well as apartment complexes.So he's doing this in the outer boroughs of New York, first in Queens, and then later he moves to Brooklyn.He's again, a true genius.

7:00 He's very good at this.He's very thrifty.He knows the cost of every single thing that goes into a house, and therefore he can really drive his contractors on cost and make sure that he's getting things done as cheaply and efficiently as possible, but also doing them to a high standard of quality.

7:19 He makes a killing in the post World War 2 economy, and that's because there's federally subsidized housing.And so to make houses for all these returning GIS, all these returning soldiers from World War 2.And so the federal government, the US government says it will give developers money to build new cheap housing for returning soldiers.

7:42 OK.But they put a cap on the amount of profit that you can make on these complexes.And so Fred Trump cleverly just makes a shell corporation.And so 1 corporation is the developer and the other is the construction company, and he owns both.

8:01 And so he just transfers all the profits to the construction company, allowing himself to make all these profits that he's not supposed to be able to make.He does this by building more, you know, more cheaply than others while still maintaining a high standard of quality, but allows him to to pocket more profit than he was supposed to as mandated by law.

8:22 He actually gets called before Congress and he just explains how he did this.It's not uncontroversial, but it is legal.And so he he makes a ton of money doing this.During this time, he marries a recent Scottish immigrant, a woman named Mary Ann McLeod.

8:40 And together they have five children.Their first is a daughter, Mary Ann, then Fred Junior or Freddie as he was known, then Elizabeth, Donald, Donald Trump, the guy we know is the 4th and then fifth is Robert Trump.So who's this this Donald Trump kid?

8:56 Well, the first thing to know about him is that he loved fighting.He loved conflict.So here's what he writes about himself.He says even in elementary school, I was a very assertive, aggressive kid.In the second grade, I actually gave a teacher a black eye.

9:12 I punched my music teacher because I didn't think he knew anything about music, and I almost got expelled.I'm not proud of that, but it's clear evidence that even early on, I had a tendency to stand up and make my opinions known.OK.So yeah, he was a really aggressive kid.

9:28 There are other stories about him throwing cake at birthday parties, throwing erasers at teachers.His sister Marianne called him, quote, extremely rebellious as a youth.And yeah, so.So that's what he was like.He was very polarizing even as a child.

9:45 He was looked to kind of around the neighborhood as a leader, but also someone that a lot of people didn't like.He's a prankster.He loves pulling pranks and hijinks.And he has this combination that many great men always seem to emerge out of, which is he has a very demanding father.

10:05 You know, he he loves his father.He really respects him and his father loves him.They have a close relationship, but his you know, when Donald Trump describes him, he says, I love my father.In the very listen to this quote in Art of the Deal, Donald Trump says the most important influence on me growing up was my father, Fred Trump.

10:24 I learned a lot from him.Listen, I learned about toughness in a very tough business.I learned about motivating people and I learned about competence and efficiency.Get in, get it done, get it done right and get out.OK.So he, he really respects his father.He, he considers him his greatest influence.

10:40 But what's the first thing he says?He learned toughness.OK, that should tell you something about the type of relationship they had.And Donald Trump was tough and a fighter.And so he's the only child who would really stand up to his father.Not that he was abusive or anything like that, but he was very hard on the children.

10:59 And Donald Trump is the only one who doesn't say just, you know, yes, father and go along with it.He he pushes back a little bit.But so he's causing all this trouble.And at one point, Fred Trump finds out that Donald has been taking trains into Manhattan to buy switchblade knives.

11:17 And that's the last straw for Fred Trump.He says, OK, this kid, he's punching teachers, he's getting into fights, and now he's buying switchblades.We need to straighten this kid out.And so he sends him off to a military school called the New York Military Academy.And that's a good environment for Donald because it's it's a military school.

11:36 It's it's very aggressive.It goes well with his aggressive nature while also being very disciplined and helping to instill in him some of the discipline and rigidity that he would need to kind of even out his temperament.

11:54 Donald says about his time in New York Military Academy.I was a good enough student at the Academy, although I can't say I ever worked very hard.OK, so he's good enough.He's OK, but he didn't work very hard, so he didn't.He was an excellent student, and that's corroborated by all accounts by other students, by teachers.

12:11 They all say that he was a good student, but not a stellar 1.He was supposedly a very good baseball player and sports was very important to him.Again, very, very extremely competitive.Here's what one person said about him.This is someone who was both a teacher and a coach.

12:27 So he coached the baseball team that Donald Trump was on and also taught him.He says, I coached baseball and football and I taught them that winning wasn't everything.It was the only thing.Donald picked right up on this.He would tell his teammates, we're out here for a purpose to win.He always had to be #1 in everything.

12:43 He was a conniver even then, a real pain in the ass.He would do anything to win.OK, so that's what kind of person he is.He's also known as a ladies man.Women weren't allowed on campus at the New York Military Academy, But Donald Trump seems to find a way.

13:01 So he gets out of Military Academy in high school, after high school, after 12th grade, and the first thing he considers is a career in the movie industry.He briefly flirts with the idea of attending film school at USC.It's the best film school in the United States.

13:18 And he doesn't end up doing it, but he does end up obsessed with show business.It's really interesting to read through his biographies and he's always throwing out these little things that you can tell.

13:33 He's totally obsessed with this.He'll be saying, you know, 1988 is the year that I built X&Y building.It's also the year that cats came out for the first time.Like he just, he doesn't have to mention that, but he can't help himself.There's also a great interview that I saw with Steve Bannon that's that's very funny, where they're talking about New York in the 80s and they're talking about crime.

13:56 Steve Bannon is trying to get across the idea of how bad crime was in the 80s.So he brings up New York in the 80s and Donald Trump says, you know, I, I remember, I think he brings up a certain year like 1987, and Donald Trump says, Oh yeah, 1987.That's the year that Andrew Lloyd Webber was living in one of my buildings and he invited me to the opening of Phantom of the Opera.

14:16 Can you believe that?I was at the first ever showing a Phantom of the Opera.And Bannon tries to steer the conversation multiple times back to how bad crime was and just can't help himself.He's like, no, no, no, wait, hold on.But I was, I was there.Can you imagine that first ever showing Phantom of the Opera, one of the great musicals?

14:34 And he's, he's truly obsessive about musicals.And I think that gets at his love for show business and showing off and, and flair and, and being a personality and, and being in front of a, a crowd in his love of public adulation.

14:53But ultimately he decides not to go into build business.And he does go to school 1st at Fordham University in the Bronx, so they can be close to home, close to his family.But then he transfers to the University of Pennsylvania where he studies real estate.Penn is a very good school started by Benjamin Franklin.

15:10 It's Ivy League if you're not from the US Penn is not quite Harvard, Stanford, Princeton, Yale level, but it's just below that.And in fact, their Business School, which he attended is called the Wharton School of Business.And it's one of the best in the country.So it is in fact an elite university.

15:31 And apparently Donald Trump does well there.This is the 60s.And so there are a lot of protests going on and it it's the age of hippies and free love.And Donald Trump has none of that.He's not interested in partying at all.

15:48 He he just goes to school.He studies pretty hard, does quite well and then comes home, reads a little bit, watches TV shows and and goes to bed and then starts the whole thing over again.One reason that he goes to college, he was considering not going to college.

16:06 He was considering going straight to work for his father, But one of the reasons he does end up going to college is to avoid the Vietnam War.He never apologizes for avoiding the Vietnam War.If you were going to college, you'd get a deferment so that you wouldn't be entered into the draft.

16:24 So he never goes into the draft.And then once he's out of college, he had, he goes to a Doctor Who declares him medically unfit because of bone spurs.OK, this is a thing that you often hear from people who were dodging the draft, who are intentionally trying to not get in the war.

16:42 They would find a Doctor Who could say, oh, you have bone spurs.The other one is like, oh, your eyesight isn't quite good enough.And so they would get medical leave to not have to join the Vietnam War.So he does this.He goes to college, he gets a doctor to find he has bone spurs, doesn't enter the Vietnam War.

17:00 He never apologizes for this.He says he thought it was a stupid war and he's like, why would I have, you know, joined up and and made myself available to go fight in a war that I thought was stupid and not worth it?So he doesn't fight in the Vietnam War.Instead, what he does is immediately make a splash in the real estate business.

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18:20 So I really recommend it.Try it out.Go to gamesinbulk.com and use Code Ben to get a discount and that is games in bulk.You'll love it.OK, so he goes to work for his father and for a little while he's just learning the ropes, going to their apartment complexes in the Bronx and in Brooklyn and, and learning how to do things on a very basic level.

18:43 But almost immediately he decides that if he's going to do real estate, he wants to do it big.He wants to do it his style.And that means going to Manhattan, He says.The real reason I wanted out of my father's business, more important than the fact that it was physically rough and financially tough, was that I had loftier dreams and visions and there was no way to implement them.

19:02 Building housing in the outer boroughs.OK, So what are these dreams and visions?You know, what is success for Donald Trump?What is he trying to accomplish?I think it's very interesting that later on he would say about one of his projects, once it's completed, he says, quote, it was an unqualified success.

19:21 It had given me visibility and credibility and prestige.OK.I think that's so interesting.When he says it's an unqualified success, he doesn't say it generated an incredible return on investment.I made a bunch of money.No, he says.It was an unqualified success.He had given me visibility, credibility and prestige.

19:39 Again, going back to that idea of show business, that's what he wants.He wants the public acclaim.He wants the visibility.He wants the credibility.He wants the prestige.So this isn't someone who's trying to maximize the amount of money in his bank account.Yes, he does want to make money.

19:55 That is definitely true.But more he wants to make money because of what I will say about him as a person than for the sake of the money.And isn't the primary focus the primary thing?Is the visibility, the credibility and the prestige.One question a lot of people have about Donald Trump is, you know, is he a self-made man or is this all just something that was given to him by daddy?

20:18 Right?And I would say it's somewhere in between.He's not exactly an Eppo baby.It's not like he never does anything really successful.He does.He does have some remarkable accomplishments, especially early on.But of course, he does get a boost from his father.Some of that is capital.

20:33 He actually doesn't get as much capital as some people say.He gets loans.He he does, he gets some money from his dad.Let's be real.He gets some money from his dad who is worth, no one knows exactly how much, but probably fifty, $100 million and not all that.

20:49 You know, he has five kids.So Donald Trump would be entitled to about 20 million of that, right?So yes, he, he's somewhere in between, but he’s not, not only is it the money, it's the credibility he gets from being associated with his dad's business.

21:07 Because not only was Fred Trump successful, he's also very well connected.You know, to develop anything in New York is very difficult to do politically because they're all these approvals you have to get from regulators, environmental regulators, the, the mayor, the mayor's office, all this stuff, right?

21:27 And so Fred Trump is Republican, but he's a Republican who is very well ingratiated with the Democratic machine of New York and has greased those wheels, has made a lot of donations, is in good with those people.And so Donald Trump was able to inherit some of those relationships.

21:42 Probably the most important thing that he inherits from his father.And we see that in the first thing he ever does, and that is the Convention Center, the Javis Center in New York.So he buys this plot of land on the East Side, I believe, of New York, and he's very opportunistic about it.

22:03 He calls, he wants this, this piece of land.And the person who owns it says, I'm not selling.I'm not interested in selling at all.And he just keeps calling back every six months to a year and says, hey, you know, you're not interested in in selling that that land yet, are you?And eventually he calls him and the guy says, actually, you know, we've fallen on difficult times and yes, we would be interested in selling.

22:28 And so Donald Trump, because he's the first one to call and he moves quickly, is able to seize it for a price that's probably a little bit below market.And so he gets this this really prime plot of land, and then he's able to find a creative use for it.Here's what he writes in Art of the Deal.

22:45 He says, perhaps the best example I can give is the first deal I made in Manhattan.I got an option to purchase the Penn Central rail yards at W 34th St.My original proposal was to build middle income housing on the site with government financing.Unfortunately, the city began to have financial problems and money for public housing suddenly dried up.

23:02 I didn't spend a lot of time feeling sorry for myself.Instead, I switched to my second option and began promoting the site as ideal for Convention Center.It took two years of pushing and promoting, but ultimately the city did designate my site for the Convention Center and that's where it was built.

23:18 Of course, if they hadn't chosen my site, I would have come up with a third approach.OK.So it's a testament to his approach, which is to be flexible in finding a deal.And so he does eventually find a deal for the Convention Center.

23:35 It's very controversial.You know, he he has to really be out in public and promoting it and saying why it's the best.But he also has his connections at town hall with the mayor.And so, you know, one interesting story from this is the seller, one of the reasons he sold to Donald Trump is Trump convinced him that he was going to be able to get a deal done, to get something actually built on the site.

24:00 And the seller, because of complicated regulations, was was going to be able to get a major payday if someone actually developed the site of these rail yards.And so there were more people.There were people who were willing to give more money for the site.

24:18 But Donald Trump basically said, you know, Are you sure they're going to be able to develop something?I can get something actually built here.And the guy says, well, how do I know that you can get something built?And he says, well, I'm, I'm very well connected with the mayor.And he says, how do I know you're well connected with the mayor?

24:35 You know, could you arrange a meeting?And he says, oh, I can arrange a meeting.I'm going to send a car for you at 2:30 tomorrow because I want to make sure you're not late, OK?Because I can definitely make this happen.So he sends the car, he picks up the guy, takes him to the mayor's office at 3:00.And the mayor sits down with him.

24:51 And under directions from Fred Trump, Donald Trump's father, he says, I'm going to give Donnie whatever he needs.He's going to be able to get something built.So that's what gives this guy the confidence to say, OK, you know, I'll sell the site to to you, Donald Trump.

25:06 And so that's how he acquires it.Ultimately, Donald Trump is not the one who actually develops and builds the Convention Center.So he brokers the deal, but someone else actually builds it.So it's a qualified success.He makes I think like a million, million, a half dollars on the deal, a great deal for him.

25:27 I mean, a million and a half dollars in in a year or two is great money even today, but especially back then, that was that was a big chunk of change.The next deal that Donald Trump does is probably probably the most successful of his entire career, and that is the old Commodore Hotel.

25:44 And so it is in this prime location in Midtown Manhattan right near Grand Central Station. So it's really well positioned.It's this old hotel, the Commodore Hotel with this long story history.It's a old famous luxury hotel in New York City.

26:02 But the neighborhood, along with a lot of Manhattan had started to get rundown.There's a lot more crime that was surging in the 70s especially.And so, and the Commodore was an old hotel.And so it, yeah, it was starting to get rundown.And the old owners of the hotel, we're not able to keep it profitable.

26:21 And it was looking worse and worse to the point where they had a flea market that was regularly operating out of the out of the main lobby of the hotel.And so Donald Trump comes along and says, hey, would you be interested in selling this and, and US redeveloping it?

26:42 And they say absolutely.Now Donald Trump goes to the city and says, hey, we need a major tax concession if we're going to do this.Because what we're trying to do is make a statement that, you know, Midtown is not going away, even though it looks like some things are going downhill and they're surging crime.

27:05 This new hotel is going to be a statement that no, no, no, this area is turning around.So this is going to be good for the city.And so can you give me a tax abatement essentially, you know, not charge taxes on on the hotel for a certain number of years.

27:21 And he manages to convince the city that this is a good idea.Kind of they they agreed to a preliminary agreement.But as it gets closer and closer to signing the final deal, some people within the city government say, oh, hold on, this is a really generous tax deal that we're giving to Donald Trump.

27:40 And so here's what he writes about.You know what he does?So he says, I worried about the growing opposition, but publicly, my posture was to take the offensive and concede nothing to my critics.When a reporter later asked me why I got a 40 year tax abatement, I answered because I didn't ask for 50.

27:59 OK.So he's really aggressive.Like, no, I deserve this.This is good for New York.I should get a tax abatement.I'm not conceding anything that I'm getting a handout from the city.When the tax breaks are in danger, the seller announces that they're going to close the hotel.

28:16 OK, so from the biography, never enough, they write.For his part, Trump got workers at the hotel to tear down the clean looking plywood and 2 by 4 studs they had used to board up the ground floor windows of shops that had closed.They replaced these materials with dirty salvage scrap wood so that people who passed on the sidewalk would see that the Commodore was a mess and complain to city officials.

28:39 At the same time, John Koskinen suddenly announced that the Commodore, which had been open for business through all the deliberations, would close within days.OK.So he's really putting pressure on the city.He's getting the current owners to say, hey, we're going to close this down right away.

28:54 We're losing money every month we're in operation.So, you know, if you don't let this deal go through with the tax abatement, this hotel is going to close.And then it's going to be a major eyesore, You know, who knows what's going to happen?And at the same time, he's making it look worse so that people are going to complain and be like, what are you guys letting?

29:10 Let Donald Trump build here?So the deal goes through, city passes it.And actually, in order to get financing, he had to team up with a existing hotel chain, the Hyatt hotel chain.And so this hotel, the old Commodore, becomes the Grand Hyatt Manhattan.

29:27 And there's a controversial renovation.Donald Trump always wants to make a splash.He wants something that's going to stand out, is not going to, you know, just fit in.And so Grand Central Station and all the hotels nearby, they all have this certain, you know, old stone look.

29:49 And he says that's not what we're doing.We're going to make it all glass.And so you can go look up the Grand Hyatt right now.And it's this I, I don't frankly think it looks great, but it is this it's certainly striking.It's entirely glass exterior.

30:06 And this is the 80s when glass, huge glass buildings are new, they're exciting.And the Grand Hyatt as soon as it opens and, and even up until the current day is just an unmitigated, unqualified success.They're able to charge more than nearby hotels.

30:23 They have higher occupancy.People love it.It's a it's a very successful hotel and it makes Donald Trump a ton of money and once again, gives him a lot of visibility and a lot of credibility and a lot of prestige.So this is probably the single greatest deal of Donald Trump's career is his wrangling, all these people wrangling the city government and the tax abatements in order to make it work financially.

30:51 His partner from the Hyatt to operate it, to bring the credibility that this is an established hotel operator and they're going to be able to do so professionally, to wrangle the financing, which was very hard to come by, to make sure the money is there to build it and the architecture to make it stand out and make it desirable.

31:11 It all comes together in this deal that is brokered by Donald Trump and Grand Hyatt is a huge success for him.He certainly tries to leverage the success into even more social connections.One of the things he does is join the most prestigious club in Manhattan called Le Club.

31:30 And you know, his father is well connected in the city government, but in this sort of business way, not in a social way, Donald Trump very much has to make his own social connections in Manhattan.And so he wants to be part of Le Club because that is the most prestigious social club in the city.

31:52 And so he repeatedly calls the president of Le Club and his secretary turns him away every single time.And eventually, you know, he's able to connive his way into getting a meeting and just tells this guy, hey, I don't have anyone to recommend me.

32:10 I don't have any social connections to the club.But I think you should let me in.My name is Donald Trump.I'm building this impressive stuff.You know, I think I'll be great for the club.And the the president says, OK, well, why don't you come have dinner with me?So he goes, he has dinner with him.They have some drinks and the guy says, OK, you're great, you're in the club.

32:29 And so this is a, a place where Donald Trump was able to make a lot of these connections.I think it's interesting to just get kind of a, a view of what kind of person he is at this time because I do think this would change a little bit.So his first chauffeur and bodyguard writes this about him and his his working for Donald Trump.

32:51 He says the pay was equal to a police salary and that included overtime for nights.There were a lot of nights because he went out a lot, but I was single so it worked out.When I got married, he came to the wedding and gave us a nice present, which he didn't have to do when my wife was pregnant.My wife chose a Doctor Who wasn't in the medical plan, but he paid for it, which is about a month's salary.

33:10 When the baby was born, he bought the car seat that we brought home her home in.He was a nice guy who was never anything but good to me.He expected loyalty, but he was also loyal back when I got the chance to go back to the Police Department, it was a difficult decision because I liked working for him.Later on, when people started saying all the negative things about him, it didn't make sense to me.

33:28 The guy I knew then was a good guy.All right.So I do think at this time and subsequently, especially in social settings, he, you know, I know someone who who met Donald Trump and he said the only other person that he has ever met who's on the level in terms of charisma with Donald Trump is Bill Clinton.

33:50 And this is someone who knows everyone.He's like those two head and shoot holders above everyone else, the most charismatic men I have ever met.Donald Trump can charm you in the blink of an eye.He is very, very charming and he he can be very nice socially, very ingratiating.

34:08 You hear this from a lot of different people, especially at this time because why not?He's ascendant, he's on top of the world.He's got all these successful developments, so it's pretty easy to be nice when you got a lot to give, right?He didn't have any vices.He didn't drink, he didn't smoke.In part, this is because I mentioned the family and he's the middle son, right?

34:28 The oldest son, Fred Junior, commonly known as Freddie.He tries to work for his father and he's just not aggressive and combative enough.He doesn't have that fighter's personality.And so he Withers under his father's toughness, and he ends up becoming a pilot.

34:45 And both Fred Trump and Donald Trump kind of make fun of him for, you know, a pilot was a prestigious occupation.But it's not like going out and conquering the world, like being a a New York real estate developer.

35:02 At one point, Donald Trump says to him, yeah, I mean, OK, you're a pilot.But in the end, it's not that different from driving a bus, is it?So.So he really cracks under this pressure, turns to alcohol, becomes an alcoholic and ends up killing him.And so Donald Trump sees this example and decides that he is never going to touch alcohol.

35:21 He never drinks, never has, and doesn't smoke, doesn't get into drugs at all.His one vice, acknowledged by everyone, is women.Loves women, loves to go out to the clubs, loves to seduce women, has a real weakness for women.OK, so that's what he's like socially at the time.

35:40 His next big development is Trump Tower.He meets with the owners of the building in the location that will become Trump Tower, and that's a department store called Bonwit Teller.And so he says, hey, I want to meet with you.

35:56 And so they're not sure what he wants to meet about, But the CEO says, OK, sure, I'll take a meeting with you.And so he says, I'd like to buy your building.And then Trump says, quote, when I was done, he said to me very politely, but also very firmly, you've got to be crazy if you think there's any way we'd sell this incredible site.

36:15 So they shake hands.He leaves.And this guy is firm, saying, under no circumstances will you ever buy this property.No way.But he goes on and says, Even so, I didn't give up.It's very similar to the convention site.

36:31 He just keeps calling and calling.And then one day, of course, Bonwit Teller has fallen on hard times.And so he says, OK, Donald, you know, come take a look.And and so Bonwit Teller is actually going through a restructuring.I think they're going to bankruptcy.

36:47 So they need to sell a bunch of property.And so Donald Trump is able to buy this property and he wants to make it the most prestigious apartment complex, you know, the tower of apartments in all of Manhattan.

37:03 That's his goal.And so he has once again, this giant glass frame.This is the building that goes on to become Trump Tower.And one of the most controversial parts about the construction is there are these freezes, these art deco freezes, which is kind of like statues, 2 dimensional statues built into the wall.

37:24 And many people think they have great artistic merit.And Donald Trump says, sure, I'll, I'll try to preserve them.But in construction, his demolition crew comes to him and says, look, these things are heavy.In order to get them down all in one piece, it's going to cost like 1/4 of $1,000,000.

37:41 And Donald Trump says, like, look, I, I would try and preserve them, but that's more than they're worth.And so he just has them demolished.And it becomes a huge controversy.There's this big outcry, especially it's seen as this symbolic act that Donald Trump, who is becoming the face of rabid capitalism, make money at any cost, showy, vain, you know, he's Donald Trump as as we know him.

38:12 He's developing the Donald Trump persona.And they're saying, look, this greedy capitalist is destroying art to build the world's most luxurious apartments.Isn't this symbolic of the decay of social fabric of America?So Trump says about this in The Art of the Deal, good publicity is preferable to bad, but from a bottom line perspective, bad publicity is sometimes better than no publicity at all.

38:37 Controversy in short cells.I'm not saying that's a good thing.And in truth, it probably says something perverse about the culture we live in.But I'm a businessman, OK?And So what he says about this is the way that that generates publicity that's helpful is they keep saying this dichotomy that, look, art is being destroyed just to create the world's most luxurious apartments.

39:01 They keep repeating this line, the world's most luxurious apartments.He's like, yeah, just keep repeating that, baby.I love hearing that.And and so, you know, it works.It gets this cachet.And his reputation as this ultra luxurious new development, once again, similar to the Hyatt, he's got to constantly juggle what he calls provisional commitments.

39:22 OK, you get the financing, the approvals, the builders, the seller, the architect.And none of them want to agree to anything if he doesn't already have the other stuff in place.And So what he has to have is absolute confidence at all times.He's always telling everyone, you know, if he's talking to people who might finance this development, he says, don't worry, I've got the approvals locked down.

39:47 I've got the architect locked down.I've got, you know, everything I need.Similarly, he's going to the city and they're like, well, if we're going to give you the approvals, we want to make sure that, I mean, there's something that's actually going to happen.Do you have the financing?He's like, yeah, I got the financing locked down.In fact, at one point the city asks for the agreement that he has with the seller, Like, OK, we can agree to this provisionally or actually, excuse me, it's the it's the financing.

40:14 The banks, they want an agreement with the seller.So they're like, we want to make sure that this is.You know, all above board that you can, you actually have access and rights to this property.And so he says sure.So he sends the agreement.The only problem is he hasn't been signed yet, but he doesn't call attention to that obviously.

40:34 And no one notices.And they move ahead with everything.Everything goes ahead.And it's only much later that anyone notices that he had sent an unsigned agreement.So at all times he shows complete confidence this is all going to happen.This is all going through and, and it does.

40:52 It was originally going to be called Tiffany Tower because it's built next to the flagship Tiffany store.So you've heard of like Tiffany jewelry.It's built next to Tiffany.And he has this eye for marketing and he says, look, Tiffany's a great brand.

41:09 It's screams luxury.So let's, let's call it the Tiffany Tower.And here's what he writes about.He says, I was originally going to call Trump Tower by another name, Tiffany Tower for the famous jewelry store next door.I asked a friend, do you think it should be Trump Tower or Tiffany Tower?He said when you change your name to Tiffany, call it Tiffany Tower.

41:26 So he thinks that's good advice.OK, great.We'll call it Trump Tower.And when it first comes out, again, very luxurious, very successful.A lot of celebrities move in.Johnny Carson, Steven Spielberg and Liberace, among others, move into Trump Tower.A lot of foreigners move in, a lot of new money.

41:44 A lot of Saudis and Asians think that, you know, they love the glitz and the glamour of this glass building with all this gold inside.But they they sell out with very high rents and make a bunch of money on it.And this is the one, this is the development about which he says it was an unqualified success.

42:03 He had given me visibility and credibility and prestige.He does certainly bring him all of those things.One incident I didn't know anything about but I found very interesting was the renovation of the Woolman Rink.So this is an ice skating rink in Central Park in Manhattan, and renovations were announced for it in 1975 as an old ice skating rink needed to be renovated.

42:22 And so it's closed in 1980, and it's announced that it's going to take two years and $4.9 million in order to renovate.Flash forward six years, it's 1986.The city has already poured $13 million into it with no discernible progress to show.

42:40 There's no rink and there's no timeline for a finish.And so Donald Trump writes a private letter to the mayor of New York City saying, hey, I'd be happy to take this project on and renovate it at cost.And I bet you that I could do it by the end of the year, by the end of this year, even though it's taking you guys six years, $13 million, you haven't got anything done.

43:01 I bet you I could do it in half a year for $3,000,000.And the mayor writes back this very sassy letter and says, oh, sure, bud.You know, you know, he thinks Donald Trump is whatever, bloviating, self promoting, whatever.

43:18 And so he writes this reply to Donald Trump and he writes it as an open letter and has it published in the New York Times.And he he says, you know, he insults him a little bit and then says, I eagerly await your reply.Well, his backfires on the mayor really bad.

43:35 The the general population is looking at this the the citizens of New York and saying, like, you're not in a place to be turning down help from someone like Donald Trump.It'd be one thing if it was going well, but it's been 6 years, $13 million.Nothing has been done.Like, what are you thinking?And so there's mounting public pressure for the mayor to accept this offer from Donald Trump.

43:59 And ultimately he is forced to do it.And so Donald Trump gets the approval to renovate this rink.He, he gets it done in record time.You know, he, he goes to a construction company and says, hey, will you guys do this at cost for the publicity goes and finds the best ice skating rink designers from Canada and has them do the designs and it goes really well.

44:23 Here's what he writes in the Art of the Deal quote.It was almost four months to the day since I've gotten approval to renovate the rink.We'd also managed to come in more than $750,000 under our $3,000,000 budget.With the city's blessing, we use the leftover money to renovate the adjacent skate house and restaurant.OK, he later says.

44:41 Speaking of the Woolman Rink, I didn't fully realize the implications of the scene at time.Now I saw it as a symptom of the bigger problem at Woolman Rink.There was absolutely no one in charge, OK.That's why he He says nothing got done before.No one was in charge.You had all these committees.

44:56 You had the mayor who was kind of in charge and three different construction companies working on it, and a whole committee of public building that was in some way or shape or form supposed to be responsible, but there was no single person who was actually in charge.He he goes on and writes in The Art of the Deal, leadership is perhaps the key to getting any job done.

45:16 There wasn't a single day when I didn't check on the progress we were making in the rink.And so I just think that shows the difference between no leadership and good leadership is nothing happening and something happening very efficiently and effectively in a very short amount of time.

45:36 The last project I'll bring up, and this is the last project to bring up from sort of his golden age, Trump golden age is television city.So he buys this big plot of land on the western side of Manhattan overlooking the Hudson River, and he develops it.

45:58 He builds what's the tallest building in Manhattan for a little bit.It ends up going well.But to me, what's interesting about this is when he is designing this new development, NBC, which is an old television network and was one of the the the mainstays of New York City, one of the big employers.

46:20 And not just a big employer, but a big splashy employer.They still are.You know, Saturday Night Live is an NBC show and it's still filmed at their headquarters in Rockefeller Center in New York City.So.So it's a tourist attraction.

46:36 It's a big deal.The NBC is in New York City and they were saying we might not stay in New York.It's not so safe anymore.And the tax situation is just horrible.So we might go to New Jersey where we can have fewer taxes.And so Donald Trump, with this property he has overlooking the Hudson on the West Side, he says, here's what we're going to do.

46:56 We're going to call it Television City.We're going to attract NBC as the big tenant.We're going to work with the city to get them some tax breaks to stay in New York City and come to this new futuristic development of of the future here on the West side of Manhattan.

47:13 And so he announces his plan.He says we're going to get NBC.They're going to be our keystone tenant.We're going to build everything around them.And we're calling this new development Television City.All right.And the interesting thing is New York City, it does kind of prick New York City to to do something.

47:30 And they end up giving all these tax incentives to NBC to stay in New York City.But they stay in their same location in Rockefeller Center.They don't come to Donald Trump's new development that he's calling Television City.So that's kind of embarrassing, right?

47:46 Kind of humiliating.You have developed this entire multi billion dollar development with all these apartment buildings and all this office space and parks and this whole thing.The whole thing is built around attracting NBC and calling it Television City.And they don't come.So what does he do?

48:01 He just rebrands it and he just moves on.And this is interesting to me because so many people are afraid to really go for stuff because they're afraid of what will happen if it fails and how they'll look and how they'll be perceived.

48:17 And, you know, Winston Churchill says that success is moving from failure to failure with no loss of enthusiasm.Trump certainly does that, right?He just, he has no sense of shame, for better or for worse, right?

48:34 And so I think everyone else is too afraid of being cringed to announce big, audacious projects like this if there's a chance that they might fail.Donald Trump just realizes I can announce a big audacious project like this, get a whole bunch of headlines, attract all this attention.

48:50 And then when NBC doesn't come, I'll just pivot.I'll just call it something else.And which is what he does.And it's still a very successful development.And it gets him free media, It gets him PR, gives people something to talk about.And it puts the development on the map, even though ultimately he has to change the name and a certain features of the development to ultimately get approved by the city and to get built and and to be successful.

49:14 So I guess the take away there is everything that you want in life, all your goals, all the realization of all your dreams is on the other side of willing to be cringe of not being afraid of failure.

49:32 That to me is one of the great lessons of Trump.I mean, you see it that there was a really funny thing that happened the other day.He, this part's not funny, but he, he called Zelensky a, a dictator, right in a statement.And this did not go over well.

49:48 Zelensky, in case someone is watching this years from now, Zelensky is the president of Ukraine and they're currently fighting a war against Russia.And the United States has been an ally of Ukraine so far in this war.And the relationship right now that the presidency has changed from Biden to Trump is tenuous.

50:04 And Zelensky and, and Trump have had some run insurance.OK.And so Trump gets very fired up and calls Zelensky a dictator.And this is a step too far.He's clearly not a dictator.And a bunch of people got upset about this.

50:20 And even his allies in Congress were like, dictator.I don't know about that.And so someone asks him the next day and says, you know, why did you call him a dictator?And he says, did I really say that?I can't believe I said that.Just completely shameless.

50:36 Just Are you sure I said that?I don't think I said that.And that's it.And he's moving on.So, you know, I guess this is one principle from Trump, which is just act, be decisive, do things that are attention grabbing and that get you towards where you want to be.

50:59 You know, call the thing Television City.And if it doesn't work out, you can just pivot.And people don't care nearly as much as you think they will.You don't have to feel shame for something like that.OK, All right, so let's recap where we're at.So he really starts in the late 60s, early 70s with his father, but he really starts developing for himself in the 1970s and then all through the 1980s.

51:26 Donald Trump is a very successful Manhattan real estate developer.He has a sterling, although not uncontroversial, reputation.You could try to Ding him for the tax breaks that he's gotten, for the connections that he inherited from his father, some of the money that he inherited from his father.

51:44 But I mean, really he has developed very successfully a number of of properties in Manhattan, which is a very difficult place to develop.You know, it's, it's very cutthroat.And he's been really successful.He's done this through a combination of bravado, confidence, cunning, the common touch, understanding what people are interested in, where they want to live, what they will find eye-catching a noteworthy.

52:12 He's done it through gut feel and great marketing and the ability to hijack the news to cover stories that he wants to publicize.So I would say up to this point, you can have qualms with the way he does things, but his record is pretty unimpeachable.

52:29 His developments are successful, and they've made a really big name for Donald Trump.He was a symbol of American dynamism, exceptionalism, capitalism, but also greed and bombast and the negative aspects of that equation.

52:51 It was the 1980s.Business was booming in America, everything was fast, everything was loud.And Donald Trump kind of represented all of that in one person.So he's successful, he's riding high, he's living fast, but very soon, all of this would very quickly fall apart.

53:14 But before we get to the downfall of Donald Trump, a quick word about the podcast Founders.Founders is one of my favorite podcasts.You can think of it as very similar to How to Take Over the World, but specifically for and about founders, founders of great companies.And David Senra, the host, is a friend of mine.

53:31 He does a fantastic job.It's just one of the best podcasts anywhere.I just can't recommend it highly enough.If you're looking for some episodes to start with, I would recommend episode 370, which is on the founder of IKEA.His name's Ingvar, and that's incredible.

53:47 And then actually, if you know, if you're listening to this, you're interested in history, I'd also recommend episode 368, which is Rockefeller's autobiography.And David has some great things to say about Rockefeller.David has done almost 400 episodes by now.And one of the things that he's best at is looking at and finding connections between all these different founders and what the common themes and patterns are that link all of them.

54:12 It's really powerful.If you're a founder, if you're interested in entrepreneurship, this is the show for you.You're going to love it.So check it out.That's founders wherever you get your podcasts.OK, so let's talk about Trump's downfall.Here's what Donald Trump would say about his downfall and why it happened. 1 magazine headline said everything he touches turns to gold.

54:33 And I believed it.I'd never known adversity.I went straight from Wharton to wealth.Even in downmarkets, I bought properties inexpensively and made a lot of money.I began to think it was easy.In the late 80s, I lost focus.I'd fly off to Europe to attend fashion shows and I wasn't looking at the clothing.

54:50 My lack of attention was killing my business.Then the real estate market crashed.I owed billions upon billions of dollars, $9.2 billion to be exact.That's $9,200,000,000.I've told this story many times before, but it bears repeating.In the midst of the crash, I passed the beggar on the street and I realized he was worth $9.2 billion more than I was.

55:12 I saw a lot of my friends go bankrupt, never to be heard from again.OK, so that's his explanation.He loses focus, he's not dialed in on his business and the real estate market goes belly up.But actually if you look at it, he's real estate investments actually do OK.

55:30 Even through the crash, it was his casinos that did emit.So Trump gets into the casino business, Atlantic City in New Jersey had recently legalized gambling in in New Jersey, in this one city in New Jersey.And this is very close to New York City.

55:45 So this was a huge potential to essentially create Las Vegas, E right, the city where people can come from New York City to gamble.So Trump wants in from the very beginning.And so he builds a few casinos, He buys a few casinos in Atlantic City.

56:03 And at first it goes well and the numbers are way bigger than hotels.He's looking at this and the amount of revenue generated by casinos is huge.And so he opens up a few casinos, they start doing well.So he double s down, triples down.

56:18 He's gobbling up as many properties in Atlantic City as he can.And then it all starts flipping on him.The economy start slowing down.The casino business had overbuilt.You know, there's such enthusiasm for this new place that too many casinos were built to take the demand.

56:36 There was just more supply than there was demand.And so the whole industry suffers.But no one more than Trump, who had built enormous high end, very expensive casinos.He had also become distracted and he'd gotten married to Ivana earlier and they had three children together.

56:57 He starts cheating on her with Marla Maples, who was a Miss America winner.And it becomes this very high profile affair.It's in all of the tabloids.Like, this is a story that, like, helps create tabloid culture in the 90s and early 2000s as we know it.

57:16 Like, his face is all over newspaper stands everywhere.And the insurance and outs of his love life and his cheating on his his wife with Marla Maples come to be known.So he was legitimately distracted.I think that's part of it.And another part of it, too, is that, you know, he says that he believes in hiring the best of the best.

57:36 Well, he had hired one of the absolute best casino executives in the world, and that casino executive and two of his top lieutenants die in a plane crash right as Trump is opening many of his biggest casinos.

57:53 And so, you know, without that management, it's very difficult.So mostly because of all these big casinos, his business goes way underwater.They're hemorrhaging money.He has to go through bankruptcy and restructuring, not personal bankruptcy, which he's always important to point out.

58:13 That's like a point of pride for him that he never personally declared bankruptcy, but his organization has to go through bankruptcy and reorganize.He gets many of his creditors to write off a lot of the debt and and restructure.

58:30 OK, He does have to give up a lot, but the point is through this restructuring, through bankruptcy, he does manage to hang on to most of what he has.And they're thinking, look, if we just really put him through the ringer, we make him sell off all of his assets, then we're going to be getting $0.50 on the dollar of what we lent him.

58:55 It's much better to let him hang on to the assets, try and manage his way through it and see if we can claw back more than than 50%, right?So they're willing to write off a lot of their debt and let him hang on to the assets and see if he can turn it around.

59:11 You know, it's just everything is falling apart for him from the late 80s through the early to mid 90s.So his casino businesses are doing horrible.His marriage goes in the tank.He tries to buy a football team, the USFL, which is like not America's premier Football League.

59:33 They try and start a new Football League and within a year it crashes and burns.They lose their TV contract, they can't play.So his team goes to zero that he has bought as USFL team.He tries to start an airline that also fails.So in the 90's the Trump brand takes a real hit.

59:51 His personal brand was always ostentatious and flashy, which works when it's working, right?When you're making lots of money, ostentatious and flashy works.It's polarizing, but it works.But when you're not succeeding, then it looks vain, ridiculous, farcical.

1:00:06 And that's how it's starting to look in the 90s.OK, So what happens?He restructures through bankruptcy.He also goes public, which would be very controversial because bankruptcy, OK, you're losing money.

1:00:23 Yes, but these are all institutional investors who are invested in you.And so, I mean, they can take a hit, right.But once you go public, you have a lot of retail investors, a lot of mom and pops like people with their pension funds invested in you.

1:00:40 And those are the kind of people who are losing money on you if you don't do well raising, if you don't do well with a a public company, that's exactly what happens.So he goes public with his best casino, the one that is still pretty successful and doing OK, right?

1:01:00 And so he gets a a bunch of investment off his IPO, the stock price shoots up.Then he uses that money that he has raised from the initial public offering to buy his worst casino from himself at an inflated price.

1:01:20 So that's not great, right?He's essentially like cashing out into his own bank account from this public company that he has created.OK.So it doesn't look great.Frankly, it's not great for his investors.

1:01:35 He's also, you know, starting at this time and then kind of for the next decade, he's doing anything, and I mean, anything to make a buck.So he's realized, all right, I'm in a bunch of debt.I need to get out of debt.What assets do I have?

1:01:51 Well, one of the assets I have is my brand There is there is brand equity.And so he just uses that brand.He starts selling Trump steaks, Trump branded water, like literally plastic water bottles of Trump water.

1:02:07 He the books that he writes from this time are like these vapid money grab books, things like think like a billionaire.OK, kind of scammy self help type stuff.Listen to this opening line from Think Like a Billionaire, which I read so you don't have to.

1:02:24 He writes.In a world of more than 6 billion people, there are only 587 billionaires.It's an exclusive club.Would you like to join us?Of course the odds are against you about 10 million to one.But if you think like a billionaire, those odds shouldn't faze you at all.

1:02:41 Billionaires don't care what the odds are.We don't listen to common sense or do what's conventional or expected.We follow our vision no matter how crazy or idiotic other people think it is.That's what this book is about, learning how to think like a billionaire.Even if you absorb only 10% of the wisdom in this book, you'll still have a good shot at becoming a millionaire.

1:03:02 OK, OK, that those are the kind of books he's writing.And to be honest, so I've read all the Trump books for this episode.The art of the deal is pretty good.Like I would actually recommend it.The art of the deal is a good book.And some of his later books about his presidency are interesting if you're interested in that.

1:03:23 And and they're Willerton, But the books from this time, man, how to get rich, How to get rich is not as bad.Think like a billionaire is horrible.I mean, it it, it's some of the most boilerplate scammy self help stuff that you can imagine.

1:03:40 It's not a good book.OK, probably the most egregious money grab from this time is Trump University, which is a program to teach you about getting rich through real estate.And look, maybe some people learn something, but it is, I mean, it's hard to see it as much more than a scam organization.

1:03:59 You show up to a paid session and they say, hey, in order to really learn the tricks of the trade, you need to come to another even more extensive session.And there just isn't much value there.A lot of people are taking advantage of for a lot of money.There ends up being a class action lawsuit, which I believe is settled, but he has to pay out some money.

1:04:17 So anyway, it's unclear how much Trump is personally involved in things like this.Probably not much.He's not the kind of guy who would personally stand up a scam like this.But I think he's in desperate financial straits.He's willing to do anything to not go broke.

1:04:34 And so I think he's he, he must have known on some level that these were shady characters that he was partnering with and, and that he's getting money from.OK.He also starts going around and doing motivational speaking seminars with people like Tony Robbins, and he's making money on those as well.

1:04:57 To that end, in the year 2000, he flirts with running for president against Al Gore and George W Bush.And here's what he says about it.Quote, in 2000, I thought about running for president of the United States as a third party candidate.I proposed some sensible ideas.

1:05:12 Tax cuts for the middle class, tougher trade deals, a ban on unregulated soft money in campaigns, comprehensive health care reform.I formed an exploratory committee and met with Reform Party leaders.But in the end, I realized I was enjoying my business too much to run for off OK, so in the book, never enough.

1:05:29 Those authors take a very dim view of this first flirtation with a presidential run.Basically, they suggest that he did it in order to draw attention to himself and get more people to come to his seminars and make a little money off it.He's the only person I know of who actually makes money running for president rather than spending money to run for president.

1:05:51 However, knowing what we know now, I mean, they wrote this book in 2015.So knowing what we know now, I think his interest was also probably at least somewhat sincere.And it is interesting that his platform has remained remarkably consistent over the years.Better trade deals, tax cuts, a more isolationist foreign policy.

1:06:11 I mean, listen to what he did all the way back in 1987.OK, Reading now from never enough quote.In early September, Trump spent more than $90,000 to purchase full page advertisements in the Times, the Boston Globe and the Washington Post, the headline of the ad announced.

1:06:27 There's nothing wrong with America's foreign defense policy that a little backbone can't cure.In the text, which was addressed to the American people, Trump questioned America's defense commitments in Europe and Asia and argued that the United States should stop paying to defend countries that can afford to defend themselves.

1:06:42 He added.Make Japan, Saudi Arabia and others pay for the protection we extend as allies.Let's help our farmers are sick, are homeless.His closing was a rallying cry.Let's not let our great country be laughed at anymore.Trump did not speak to the first reporters who phoned him after this ad appeared.

1:06:59 But then he changed his mind.He told them that he had no intention of running for office but had paid to spread his message.Because I'm tired of watching the United States get ripped off by other countries.OK, so he doesn't end up running for president in 2000.But I think it taught him that he did have the stomach for it.

1:07:17 And I think his interest was sincere.You know, it is amazing that he has always had the same opinions.It actually is interesting to me, you know, people who think, oh, he's an asset of Russia, of Putin, and that's why he wants to weaken NATO.

1:07:35 And that's why he doesn't want to spend money defending Ukraine.Like, no, there's actually a very consistent through line going all the way back to 1987 that he's had this view.He views the world in terms of deals, and he doesn't like the idea of defending someone else without getting anything direct or immediate in return because that seems like a bad deal to him.

1:07:57 And so, yeah, I, I think that at least on some level of the interest must have been sincere in 2000.And certainly it placed the thought in his mind.OK, well, from there, he's doing things that are kind of scammy.

1:08:13 His reputation is sort of coming back.I mean, he's getting his name out there and he's no longer in debt.He's not going through bankruptcy anymore.However, he's still got this kind of stink of the bankruptcies of the of the 1990s on him.

1:08:31 There is one thing that really turns things around for him and that is ATV show that begins in the early 2000s called The Apprentice.The Apprentice is a reality TV show in which some contestants come together and they are competing to get a job with Donald Trump.

1:08:49 They accept, you know, all sorts of people from different backgrounds, and they give them challenges from week to week in which they can prove themselves.And then the, the person who does worst in that competition, they, they bring them all into a boardroom and Trump decides who performed the worst.

1:09:05 And then he looks at him and goes, you're fired.And then they're off the show.OK.And then the the winner gets hired, gets paid.I think the salary is $250,000 a year to go work for Donald Trump.That was a good salary back then.So for those of you who aren't around, the first few seasons of The Apprentice were a genuine phenomenon.

1:09:27 It was a huge show, really good ratings.I will stand by it was a good show.Like, I enjoyed it at the time.It, it's very well produced.It's it's, it's good reality TV.It's it's an easy watch.It's hard not to get sucked in the show.

1:09:45 The ratings do dip over time because it's difficult to recreate the same thing over and over.So they start going into Celebrity Apprentice and it doesn't perform quite as well.

1:10:02 They they're never quite able to capture the energy and excitement and popularity of those first couple seasons, which were genuine phenomenons when when they came on television.But this really, I mean, they're big enough that they get Trump in front of a lot of people.

1:10:19 They get in front of a lot of people with positive associations because he's in charge and it's an entertaining show and he seems like a great manager.So that is what gets him back in the public eye.I think that's what gives him enough of a name and enough popularity across the country that when he floats the idea of running for president in 2016, there's enough there to to give him the momentum and to give him the poll numbers to think maybe I could actually do this and win.

1:10:50 And so it's hard to overemphasize how important the show The Apprentice was to Trump's resurrection as a public figure.OK, well, I'm not going to go into his run for president nor into his terms of office as president again, because this isn't a political show.

1:11:11 I just want to see what it is about Trump, how he thinks, how he did things that kind of catapulted him toward who he eventually became.So having gone through the story broadly, let's take a step back.

1:11:27 Who is Donald Trump?What explains this guy?The first thing he's a deal maker.His book was called The Art of the Deal, and that's because he's good at deals and he loves deals.He's not a great money maker.

1:11:44 He's a good money maker, but he's not a great one and he's not a great executive.Frankly, he's maybe not even a good executive or manager, but he is good at making deals.Here's what he says about making deals.He has, frankly, like an almost erotic attachment to making deals.

1:12:00 Here's what he writes in The Art of the Deal.He says I don't do it for the money.I've got enough, much more than I'll ever need.I do it to do it.Deals are my art form.Other people paint beautifully on canvas or write wonderful poetry.I like making deals, preferably big deals.

1:12:17 That's how I get my kicks, OK?One of the first people to profile Trump all the way back in the early 80s, Wayne Barrett wrote.After getting to know him, I realized that his deals are his life.He once told me I won't make a deal just to make a profit.

1:12:33 It has to have its own excitement, its own flair.Another Manhattan developer said it differently.Trump won't do a deal unless there's something extra, a kind of moral larceny in it.He's not satisfied with a profit.He has to make something more.Otherwise, there's no thrill.OK, I think this explains so much of Trump, this sort of romantic, almost artistic attachment to deals.

1:12:58 He loves to make deals.I think that's what explains his success and his failures.Real estate is a deal based business.When you're building housing, apartments, condos, hotels, you succeed or fail based on the structure of the deal.

1:13:20 Yes, good operations can definitely make a difference, especially on the margins, but the success of a building is won or lost based on the deal and the way it's structured from the beginning.However, casinos are the opposite.

1:13:38 Casinos are all about financial manipulation and excellent operations and making sure that you structure them on an ongoing operation basis to get you great returns.

1:13:56 And that is not where Trump excels at all.He's not a great operator.He's not a great executive.He is a great deal maker.And I think you can actually see this, you know, in the 90s, he acquires, well, he acquires Mar a Lago back in the 80s as a private residence.

1:14:13 And in the 90s, he turns it into a private club, into a resort in 1994.And this is when all of his casinos are falling apart and he's going bankrupt.And yet Mar a Lago does extremely well and does well up until the current day.

1:14:30 So it's not just that he lost focus.It's not really a shift in time of like, oh, he's good in the 70s and 80s, he's bad in the 90s and 2000s.No, it is he's good deals based businesses and he's bad at operations based businesses.

1:14:47 And frankly, I think you see that in his presidency as well.So you think about it, he's he's maybe not a great manager, not a great leader of the executive branch.So you think about his cabinet and he has three secretaries of defense, 2 secretaries of state, three different attorney generals, the list goes on.

1:15:07 Three different chiefs of staff.A lot of these people burn out.Like the management is not great.But what was his biggest success, Biggest bipartisan success?Kind of unassailable.Everyone agrees that this was pretty great.And it's the Abraham Accords.It's this agreement between Israel and a bunch of other Middle Eastern countries that kind of regularizes relations and helps bring about more peace in the Middle East.

1:15:29 It is a deal.So even still, he, he's good at deals and he he's not so good at management.So I think that explains a huge part of who Donald Trump is.He is a deal maker.What else do we learn about him?

1:15:46 He's someone with a flair for drama.He he's a showman at heart.He thought about going and, and being a Hollywood executive.And in some ways, I think he still sees himself as someone who kind of is that, you know, and this is someone who who's eventual turn around comes from ATV show.

1:16:05 He has always had this knack for understanding what people want to talk about and giving it to them.And I think that understands a lot of his motivation is that again, he's someone who's in it for the exposure, for the prestige, for the visibility and, and, and for the recognition.

1:16:29 What is he like personally?He's someone who is loyal, warm and friendly when you don't stand in his way and when you're not disappointing him.However, if you are standing in his way or you are disappointing him, kind of all bets are off in terms of how he might treat you.Donald Trump is a fighter.

1:16:48 He's a pugilist.He loves conflict, confrontation and controversy.It's interesting to me that people have thought about other celebrities running for office ever since Donald Trump.Now people start to bring up, OK, well, if Donald Trump, who was this big celebrity and he successfully ran for president, why don't we run The Rock or Oprah?

1:17:11 And I think that those in particular are the people I hear floated the most.And it's a horrible idea to have The Rock or Oprah.Why?Because most people who are public figures, especially people who are actors or are in show business, they thrive on being liked on consensus.

1:17:32 They don't love conflict and controversy like Trump does.You have to to to make in politics.You have to find those people that thrive on conflict and controversy.You know, what was the issue that made Trump a political figure?

1:17:51 I don't know if you guys remember this.What was the first thing before he ran for president in 2016?What was his first issue?It was birtherism.It was him calling into question Barack Obama's birth certificate and saying he thought that maybe he was born in Kenya.Now, obviously that is not a non controversial topic.

1:18:09 He was attracted to it because it was controversial, because it stirred things up, because he knew that it would get him in the headlines.So look, my prediction is as we think about celebrities who will succeed in the future, look for people who are already comfortable being controversial, who are comfortable with conflict.

1:18:31 So for example, I think if I had to identify someone who I think will be very successful if they decide to run for president, I think of the Paul brothers, OK, these are people who are incredibly controversial as TikTok stars and, and didn't just not only didn't mind it, but they leaned in to the controversy.

1:18:50 They liked it.And now they're literally fighters, They're boxers, They're really fighting people.These are clearly guys who are very comfortable with conflict and taking controversial opinions.So I think they would do well in politics.Whereas I think if you look at other creators, most of them aren't looking for the conflict in the same way.

1:19:12 So if you want to leverage a career in the public eye to get into politics, you have to be that type of person who's very comfortable fighting as Trump is.OK, what else?What else can we learn from Donald Trump?

1:19:28 He controls the narrative by throwing out red meat, he wrote.Quote.One thing I've learned about the press is that they're always hungry for a good story, and the more sensational the better.It's in the nature of the job, and I understand that.The point is that if you are a little different or a little outrageous, or if you do things that are bold or controversial, the press is going to write about you.

1:19:47 I've always done things a little differently.I don't mind controversy, and my deals tend to be somewhat ambitious.Also, I achieved a lot when I was very young and I chose to live in a certain style.The result is that the press has always wanted to write about me.OK, you find this with a lot of great entrepreneurs.

1:20:06 Yes, they advertise.However, they find ways to be in the news and that is the greatest way they advertise.Donald Trump is just a master of that.Once again, this comes from his willingness to be controversial and and to be involved in fights.

1:20:25 And on that note, he is definitely playing a character.However, the character that he plays is genuinely a part of who he really is.But here's what he writes about playing a role.Quote The word persona has an interesting root.It comes from the Latin word meaning mask.

1:20:42 This, however, is not derogatory.It's necessary.Each of us has a persona.We need it for survival.It's the face we put on for public use, and it can be intentional or unconscious.For example, a salesman who has lost his entire family in an accident is naturally devastated, but to work effectively with his customers, he must appear cheerful and confident.

1:21:00 That's part of his persona.It's a survival device.The only danger is when people become their persona.That means something has been shut off somewhere along the line, and these people will end up hiding behind the false personality that works professionally.As I am very much in the public eye, this hits home and I gave it considerable thought.

1:21:18 Fortunately, I am aware of my public side as well as my private side.And while I'm not one for hiding much, I know there are several dimensions in which I operate.That's one reason I feel at home at the Trump Organization.The people I work with day in and day out.No, I'm not entirely a glam guy.They see how hard I work.

1:21:34 One person said I am very much like a Mormon, which I took as high praise.Thanks, Donald.OK, so he he knows that he is building a public persona.It's not totally who he is.He has a different personal dimension, but he is intentionally cultivating a public persona.

1:21:52 And I think everyone who wants to take over the world, wants to be extremely successful, needs to do that.On that note, he believes his ego is key to who he is.He says, I remember saying to someone, show me someone who has no ego, and I'll show you a big loser.I was trying to stir things up and provoke a reaction, but I later realized the basic idea is on target.

1:22:11 OK, look, I'll end by saying this.Donald Trump has succeeded.My main takeaways are constantly demand attention and always fight.Always fight.It's It's no coincidence that when he got shot in Butler, PA, he stood up.

1:22:30 He raised his first and what did he say?Fight, fight, fight.That nothing could be a more perfect encapsulation of who Donald Trump is and and why he does what he does.Fight, fight, fight.

1:22:47 And it explains the best parts of his personality and and the best parts of what he does and the worst parts he is at heart, a deal maker and he's a fighter.So anyway, I'll wrap it there.I know this is going to be a controversial episode.

1:23:04 I actually don't know who's going to attack me from the right, from the left.I imagine many of you are going to be unhappy for one reason or another, but I don't know he he's achieved a lot and I really felt like I, I learned a lot from reading and, and coming to understand better his story.

1:23:21 So I hope you enjoyed it as well.For those of you who are premium subscribers, I am going to go more into his personal life and I'm going to go through some of my favorite motivational quotes from Donald Trump because.He does have.He does have some very good ones that that I like and enjoy.

1:23:38 I'm going to go through his work habits.I'm going to go just through more, more takeaways, I guess in this episode because of Donald Trump.I didn't want to go too much into like Donald Trump inspirational figure, but I did find myself inspired in many ways, even if I was turned off in others.

1:23:57 But in the endnotes, I will just distill some of those maybe more inspiring takeaways from what he talks about and how he works.So if you're interested in that, go to takeoverpod.supercast.com.And that is Takeover Pod as in Takeover podcast, Takeover pod dot supercast.com.

1:24:14 And for $7.00 a month you can get the premium subscription and get all of my Endnotes episodes, all the full episodes, all the mini episodes, which I'm doing about one a week now of there's some really good stuff there.So I hope you'll go subscribe.But if not, until next time.

1:24:30 Thank you for listening to How to Take Over the World.Sorry to keep you waiting.Complicated business.Complicated.If I give you one message to hold in your hearts today, it's this.Never, ever give up.

1:24:54 Oh, and before you go, before you go.This episode is brought to you by Speechify.Speechify turns anything into a podcast.I use it a ton.I used it for the research for this book, and so I would just listen and read at the same time on my phone through Speechify and then every time that there was a quote I wanted to remember, I just took a screenshot and drop that into my Notes app.

1:25:16 So it's a great way you can get through more material.You can read faster when you read and listen at the same time while still maintaining a super high level of comprehension.Great leaders, great conquerors, great scientists, great artists, great founders, they all are obsessed with taking in more information, learning more as quickly as they can.

1:25:39 And Speech 5 is just a fantastic tool for learning more, learning faster.So go to speech5.com/ben.You get a 15% discount on Speech 5 Premium.You won't regret it.

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About Episode

Donald Trump: real estate mogul, master marketer, and the most polarizing figure of our time. How did he go from a brash young developer in Manhattan to the most powerful man in the world? In this episode of How to Take Over the World, we break down the strategies, mindset, and raw ambition that fueled his rise.

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