Ivanka Trump: Politics, Family, Real Estate, Fashion, Music, and Life

The following is a conversation with Ivanka Trump, businesswoman, real estate developer, and former senior advisor to the president of the United States. I've gotten to know Ivanka well over the past two years. We've become good friends, hitting it off right away over our mutual love of reading, especially philosophical writings from Marcus Aurelius, Joseph Campbell, Alan Watts, Victor Franco, and so on. She is a truly kind, compassionate, and thoughtful human being. In the past, people have attacked her, in my view, to get indirectly at her dad, Donald Trump, as part of a dirty game of politics and clickbait journalism. These attacks obscured many projects and efforts, often bipartisan, that she helped get done, and they obscured the truth of who she is as a human being. Through all that, she never returned the attacks with anything but kindness and always walked through the fire of it all with grace. For this, and much more, she is an inspiration and I'm honored to be able to call her a friend.

You said that ever since you were young, you wanted to be a builder, that you loved the idea of designing beautiful city skylines, especially in New York City. I love the New York City skyline. So, describe the origins of that love of building. I think there's both an incredible confidence and a total insecurity that comes with youth. So, I remember at 15, I would look out over the city skyline from my bedroom window in New York and imagine where I could contribute and add value, in a way that I look back on and completely laugh at how confident I was. But I've known since some of my earliest memories, it's something I've wanted to do. And I think fundamentally, I love art. I love expressions of beauty in so many different forms.

A hundred percent. One of the underlying principles of the page I just mentioned, and I hear folks mention this a lot, is that modern architecture is kind of boring, that it lacks soul and beauty. And you just spoke with admiration for both modern and for Gothic, for older architecture. So, do you think there's truth that modern architecture is boring?

What in general is your philosophy of design and building in architecture? Well, some of the most recent projects I worked on prior to government service were the Old Post Office building and almost simultaneously, Trump Doral in Miami. So, these were both two just massive undertakings, both redevelopments, which in a lot of cases, having worked on ground-up construction redevelopment projects, are in a lot of ways much more complicated because you have existing attributes, but also a lot of limitations you have to work within, especially when you're repurposing a use. So, the Old Post Office building on Pennsylvania Avenue was-

If we go back to that young Ivanka, the confidence of youth, and if we could talk about your mom. She had a big influence on you. You told me she was an adventurer. Yeah.

I think my father's sense of humor is sometimes underappreciated, so he had an amazing and has an amazing sense of humor. He loved music. I think my mom loved music as well, but my father always used to say that in another life he would've been a Broadway musical producer, which is hilarious to think about. But he loves music. That is funny to think about.

So amongst many other things, you created a fashion brand. What was that about? What was the origin of that? I always loved fashion as a form of self-expression, as a means to communicate either a truth or an illusion, depending on what kind of mood you were in. But this second body, if you-

And that's a really hard thing especially, and I think one of the things that I love most about all of these creative pursuits is that ability to work with the best people. Right now I'm working with my husband. We have this 1400 acre island in the Mediterranean and we're bringing in the best architects and the best brands. But to have a point of view and to challenge people who are such artists respectfully, but not to be afraid to ask questions, it takes a lot of confidence to do that. And it's hard. So these are actually just internal early renderings. So we're in the process of doing the master planning now, but- This is beautiful. I mean, it's on a side of a mountain.

I kind of want to forever be excited by the Peek-A-Boo phenomena, the simple joys. We're talking about on fashion, having the confidence of taste to be able to sort of push through on this idea of a design. But you've also mentioned somebody you admire is Rick Rubin in his book, The Creative Act. It has some really interesting ideas, and one of them is to accept self-doubt and imperfection. So is there some battle within yourself that you have on sort of striving for perfection and for the confidence and always kind of having it together versus accepting that things are always going to be imperfect? I think every day. I think I wake up in the morning and I want to be better. I want to be a better mom. I want to be a better wife. I want to be more creative. I want to be physically stronger. And so that very much lives within me all the time. I think I also grew up in the context of being the child of two extraordinarily successful parents, and that could have been debilitating for me. And I saw that in a lot of my friends who grew up in circumstances similar to that. They were afraid to try for fear of not measuring up.

Harness the fear. The other thing he writes about is intuition, that you need to trust your instincts and intuition. That's a very recruitment thing to say. So what percent of your decision making is intuition or what percent is through rigorous careful analysis, would you say? I think it's both. It's like trust, but verify. I think that's also where age and experience comes into play, because I think you always have sort of a gut instinct, but I think well-honed intuition comes from a place of accumulated knowledge. So oftentimes when you feel really strongly about something, it's because you've been there, you know what's right. Or on a personal level, if you're acting in accordance with your core values, it just feels good. And even if it would be the right decision for others, if you're acting outside of your integrity or core values, it doesn't feel good and your intuition will signal that to you. You'll never be comfortable. So I think because of that, I start oftentimes with my intuition and then I put it through a rigorous test of whether that is in fact true. But very seldom do I go against what my initial instinct was, at least at this point in my life.

Amongst many other things. You were on The Apprentice. People love you on there. People love the show. So what did you learn about business, about life from the various contestants on there? Well, I think you can learn everything about life from Joan Rivers, so I'm just-

I think certain people are just born to be entertainers. Like Elvis on stage, they come to life. This is where they're truly happy. I've met guys like that. Great rock stars. This is where they feel like they belong, on stages. It's not just a thing they do and there's certain aspects they love, certain aspects they don't. This is where they're alive. This is where they've always dreamed of being. This is where they want to be forever. Michael Jackson was like that.

And I just in general love to see people that have found the thing that makes them come alive. I, as I mentioned, went to the jungle recently with Paul Rosolie, and he's a guy who just belongs in the jungle. That's a guy where when I got a chance to go with him from the city to the jungle, and you just see this person change, of the happiness, the joy he has when he first is able to jump in the water of Amazon River and to feel like he's home with the crocodiles, and all that, with his calling friends and probably dances around in the trees with the monkeys. So this is where he belongs, and I love seeing that. You felt that. I mean, I watched the interview you did with him and he felt that his passion and enthusiasm, it radiated. And I mean, I love animals. I love all animals. Never loved snakes so much. And he almost made me, now I appreciate the beauty of them much more than I did prior to listening to him speak about them. But it's an infectious thing. He actually, we were talking about skyscrapers before. I loved it. He called trees skyscrapers of life, and I thought that was so great.

Yeah, the power of the waves is cool. I love swimming out into the ocean and feeling the power of the ocean underneath you, and you're just like this speck. And you can't fight it, right?

How did life change when your father decided to run for president? Wow, everything changed almost overnight. We learned that he was planning to announce his candidacy two weeks before he actually did. And nothing about our lives had been constructed with politics in mind. Most often when people are exposed to politics at that level, that sort of national level, there's first city council run, and then maybe a state-level run, and maybe, maybe congress, senator ultimately the presidency. So it was unheard of for him never to have run a campaign and then run for president and win. So it was an extraordinary experience. There was so much intensity and so much scrutiny and so much noise. So that took for sure a moment to acclimate to. I'm not sure I ever fully acclimated, but it definitely was a super unusual experience.

What was it like trying to get stuff done in Washington in this place where politics is a game? It feels that way maybe from an outsider perspective. And you go in there trying, given some of those stories, trying to help people. What's it like to get anything done? It's an incredible cognitive lift ...

It's the only time in my life where you actually feel like there's always a conflict, between work and life and making sure, as a woman, I'd often get asked about how do you balance work and family? And I never liked that question because balance, it's elusive. You're one fever away from no balance. Your child's sick one day. What do you do? There goes balance. Or you have a huge project with a deadline. There goes balance. I think a better way to frame it is, am I living in accordance with my priorities? Maybe not every day, but every week, every month. And reflecting on have you architected a life that aligns with your priorities so that more often than not you're where you need to be in that moment. And service at that level was the one time where you really you feel incredibly conflicted about having any priorities other than serving. It's finite.

What advice would you give to other mothers just planning on having kids and maybe advice to yourself on how to continue figuring out this puzzle? I think being a parent, you have to cultivate within yourself, like hide in levels of empathy. You have to really look at each child and see them for who they are, what they enjoy, what they love, and meet them where they're at. I think that can be enormously challenging when your kids are so different in temperament. As they get older, that difference in temperament may be within the same child, depending on the moment of the day, but it really, I think it's actually made me a much softer person, a much better listener. I think I see people more truly for who they are as opposed to how I want them to be sometimes. And I think being a parent to three children who are all exceptional and all incredibly different has enabled that in me.

You made the decision not to engage in the politics of the 2024 campaign. If it's okay, let me read what you wrote on the topic. "I love my father very much. This time around I'm choosing to prioritize my young children and the private life we're creating as a family. I do not plan to be involved in politics. While I will always love and support my father going forward, I will do ... While I will always love and support my father, going forward, I will do so outside the political arena. I'm grateful to have had the honor of serving the American people, and I will always be proud of many of our Administration's accomplishments. So can you explain your thinking, your philosophy behind that decision?

No more duels. You mentioned Dolly Parton.

Ivanka Trump and Lex Fridman discuss adele.

Yeah, I mean, she's extraordinary. Her voice is unreal. So I find her to be so talented. And she's so unique in that three year olds love her music. She was actually the first concert Arabella ever went to at Madison Square Garden when she was around four. And 90-year-olds love her music. And that's pretty rare to have that kind of bandwidth of resonance. So I think she's so talented. We actually just saw her, I took all three kids in Las Vegas around a month ago. Alice Johnson, whose case I had worked with in the White House, my father commuted her sentence, her case was brought to me by a friend, Kim Kardashian, and she came to the show. We all went together with some mutual friends. And that was a very profound... It was amazing to see Adele, but it was a very profound experience for me to have with my kids because she rode with us in the car on the way to the show, and she talked to my kids about her experience and her story and how her case found its way to me. And I think for young children, it's very abstract, policy. And so for her to be able to share with them this was a very beautiful moment and led to a lot of really incredible conversations with each of my kids about our time and service because they gave up a lot for me to do it. Actually, Alice told them the most beautiful story about the plays she used to put on in prison, how these shows were the hottest ticket in town. You could not get into them, they always extended their run. But for the people who were in them, a lot of those men and women had never experienced applause. Nobody had ever shown up at their games or at their plays and clapped for them. And the emotional experience of just being able to give someone that, being able to stand and applaud for someone and how meaningful that was. And she was showing us pictures from these different productions and it was a beautiful moment.

The way Adele can hold just the badassness she has on stage, she does heartbreak songs better than anyone. Or no, it's not even heartbreak. What's that genre of song, like Rolling in the Deep, like a little anger, a little love, a little something, a little attitude, and just one of the greatest voices ever. All that together just her by herself. Yeah, you can strip it down and the power of her voice. I think about that. One of the things we were talking about live music, one of the amazing things now is there's so much incredible concert material that's been uploaded to YouTube. So sometimes I just sit there and watch these old shows. We both love Stevie Ray Vaughan, like watching him perform. You can even find old videos of Django Reinhardt.

No. I cry. Look up... It was in LA. It was like the Temple Missionary Baptist Church. Talk about stripped down. She's literally a... I mean, just listen to this.

I love watching Queen, like Freddie Mercury, Queen performances in terms of vocalists and just great stage presence. That Live Aid performance is considered one of the best of all, I think.

So you've been training jiu-jitsu. Yes. Trying.

It's a lot. There are things that just popped to mind that you're thinking about, especially in the near future? Just anything.

I think I feel a lot of hope when I'm in nature. I feel a lot of hope when I am experiencing people who are good and honest and pure and true and passionate, and that's not an uncommon experience. So those experiences give me hope. Yeah, other humans. We're pretty cool.