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

0:00:06 The following is a conversation with Ivanka Trump, businesswoman, real estate developer,
0:00:09 and former senior advisor to the President of the United States.
0:00:15 I’ve gotten to know Ivanka well over the past two years. We’ve become good friends,
0:00:21 handing it off right away over our mutual love of reading, especially philosophical writings from
0:00:29 Marcus Aurelius, Joseph Campbell, Alan Watts, Victor Franco, and so on. She is a truly kind,
0:00:34 compassionate, and thoughtful human being. In the past, people have attacked her, in my view,
0:00:40 to get indirectly at her dad, Donald Trump, as part of a dirty game of politics and click-bait
0:00:48 journalism. These attacks obscured many projects and efforts, often bipartisan, that she helped get
0:00:56 done, and they obscured the truth of who she is as a human being. Through all that, she never returned
0:01:02 the attacks with anything but kindness, and always walked through the fire of it all with grace.
0:01:10 For this, and much more, she is an inspiration, and I’m honored to be able to call her a friend.
0:01:20 Oh, and for those living in the United States, happy upcoming Fourth of July. It’s both an
0:01:26 anniversary of this country’s Declaration of Independence and an anniversary of my immigrating
0:01:34 here to the U.S. I am forever grateful for this amazing country, for this amazing life,
0:01:41 for all of you who have given the chance to a silly kid like me, from the bottom of my heart.
0:01:49 Thank you. I love you all. And now, a quick few second mention of each sponsor. Check them out
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0:02:22 go to lexfreedmen.com/hiring. And now, onto the full ad reads. As always, no ads in the middle.
0:02:28 I try to make these interesting, but if you skip them, friends, I will not hold it against you.
0:02:32 I will forgive you, in fact, I will continue to celebrate you,
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0:04:26 engineer at heart still writes code, all that kind of stuff, and a philosopher. It’s really
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0:04:35 I don’t even know if he knows that Shopify sponsors this podcast, which is,
0:04:43 I guess an indication of a large successful company where all of the stuff is delegated.
0:04:48 I think we just connected as human beings. Anyway, he’s a great leader, great person,
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0:05:19 This episode is also brought to you by Netsuite. Speaking of businesses, it’s an all-in-one cloud
0:05:24 business management system. It’s the machine within the machine that helps find the common
0:05:30 language between the different modules of a business. It’s, I guess, called an ERP system,
0:05:35 Enterprise Resource Planning. The fact that I don’t really know anything about ERP,
0:05:46 the terminology of it, is a kind of inkling from the Jungian shadow of capitalism, that it’s not
0:05:52 enough to be a designer, an idea person, an engineer. You have to know so many parts of a
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0:06:03 Manages financials, HR, inventory supply, e-commerce, much more. Running a business is
0:06:09 really tough. This is one of the things I’ve been really, really thinking a lot about. I love
0:06:14 being an individual contributor, sort of an engineer as part of a small team that builds stuff,
0:06:19 or creative person as part of a small team that builds stuff, and like love the people you work
0:06:25 with and just collaborate, brainstorm, argue, all of that, and create together. And when you scale
0:06:34 that business, man, so much pain starts to emerge. But the other side of the coin of that pain is
0:06:39 you get to have impact. You get to potentially make a lot of people in the world feel good.
0:06:45 If you put a lot of love in the product and they feel that love that makes people feel good, so
0:06:49 it’s a trade-off and it’s something I think a lot about. I don’t care about money, I don’t care
0:06:56 about any of that stuff, but it is something I care a lot about to have a positive impact in this
0:07:04 world on a small scale or a large scale. Either one, all of it is magical. Anyway, over 37,000
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0:07:38 into the night because I love it. But when I get to the bed and ahead of me because it’s scheduled,
0:07:44 it just gets cold and a warm blanket and I could just disappear into the beautiful, beautiful abyss
0:07:50 of dreams. I stay there for six, seven, eight, sometimes nine, and get crazy sometimes. I go
0:07:55 nine, sometimes I get 10 hours. I recently got 10 hours of sleep. I was like, what happened?
0:08:02 It all went dark and I woke up. The light emerged from the windows and wow. It’s a good feeling.
0:08:08 Anyway, that disappearance, that teleportation procedure can only happen under bed. That’s
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0:10:12 And now, dear friends, here’s Ivanka Trump.
0:10:21 You said that ever since you were young, you wanted to be a builder,
0:10:25 that you loved the idea of designing beautiful city skylines, especially in New York City.
0:10:30 I love the New York City skyline. So describe the origins of that love of building.
0:10:40 I think there’s both an incredible confidence and a total insecurity that comes with youth.
0:10:47 So I remember at 15, I would look out over the city skyline for my bedroom window in New York and
0:10:57 imagine where I could contribute and add value in a way that I look back on and completely laugh
0:11:02 at how confident I was. But I’ve known since some of my earliest memories, it’s something I’ve wanted
0:11:09 to do. And I think I fundamentally, I love art. I love expressions of beauty in so many different
0:11:19 forms. With architecture, there’s the tangible. And I think that marriage of function and something
0:11:27 that exists beyond yourself is very compelling. I also grew up in a family where my mother was
0:11:32 in the real estate business working alongside my father. My father was in the business and I saw
0:11:37 the joy that it brought to them. So I think I had these natural positive associations. They used
0:11:44 to send me as a little girl renderings of projects they were about to embark on with notes asking
0:11:49 if I would hurry up and finish school so I could come join them. So I had these positive associations,
0:11:55 but it came from something within myself. I think that as I got older and as I got involved in real
0:12:02 estate, I realized that it was so multidisciplinary. You have, of course, a design, but you also have
0:12:08 engineering, the brass tacks of construction, there’s time management, there’s project planning,
0:12:14 just the duration of time to complete one of these iconic structures. It’s enormous. You can
0:12:20 contribute a decade of your life to one project. So while you have to think big picture, it means
0:12:28 you really have to care deeply about the details because you live with them. So it allowed me
0:12:33 to flex a lot of areas of interest. I love that confidence of youth. It’s funny because we’re
0:12:42 all so insecure in the most basic interactions, but yet our ambitions are so unbridled in a way
0:12:48 that makes you blush as an adult. And I think it’s fun. It’s fun to tap into that energy.
0:12:53 Yeah, where everything is possible. I think some of the greatest builders I’ve ever met
0:12:58 kind of always have that little flame of everything is possible still burning.
0:13:03 That is a silly notion from youth, but it’s not so silly. Everybody tells you something is impossible,
0:13:09 but if you continue believing that it’s possible and have that naive notion that you could do it,
0:13:13 even if it’s exceptionally difficult, that naive notion turns into some of the greatest projects
0:13:20 ever done. 100%. Going out to space or building a new company where everybody said it’s impossible,
0:13:26 taking on a gigantic company and disrupting them and revolutionizing how stuff is done,
0:13:33 or doing huge building projects, where like you said, so many people are involved in making
0:13:39 that happen. We get conditioned out of that feeling. We start to become insecure and we
0:13:47 start to rely on the input or validation of others and it takes us away from that sort of core
0:13:55 drive and ambition. It’s fun to reflect on that and also to smile because whether you
0:14:02 can execute or not, time will tell. That was very much my childhood.
0:14:07 Yeah, of course, it’s important to also have the humility once you get humbled and realize
0:14:13 that it’s actually a lot of work to build. I still am amazed just looking at big buildings,
0:14:18 big bridges that human beings are able to get together and build those things.
0:14:24 That’s one of my favorite things about architecture is just like, wow, it’s a
0:14:29 manifestation of the fact that humans can collaborate and do something like Epic much
0:14:34 bigger than themselves. It’s like a statue that represents that and it can be there for a long
0:14:41 time. I think in some ways you look out at different city skylines and it’s almost like
0:14:50 a visual depiction of ambition realized. It’s a testament to somebody’s dream, not somebody,
0:14:59 whole ensemble of people’s dreams and visions and triumphs and in some cases failures
0:15:06 if the projects weren’t properly executed. You look at these skylines and it’s a testament
0:15:13 that I actually heard once architecture described as frozen music that really resonated with me.
0:15:18 I love thinking about a city skyline as an ensemble of dreams realized.
0:15:25 Yeah, I remember the first time I went to Dubai and I was watching them dredging
0:15:31 out and creating these man-made islands. I remember somebody once saying to me,
0:15:37 they’re an architect, an architect actually who collaborated with us on our tower in Chicago.
0:15:44 He said that the only thing that limited what an architect could do in that area was gravity
0:15:51 and imagination. Yeah, but gravity is a trick you want to work against and that’s where civil
0:15:56 engineers, one of my favorite things, they used to build bridges in high school for physics classes.
0:16:01 You have to build bridges and you compete on how much weight they can carry relative to their own
0:16:08 weight. You study how good it is by finding its breaking point and that was a deep appreciation
0:16:14 for me on a miniature scale, on a large scale, what people are able to do with civil engineering
0:16:20 because gravity is a trick you want to fight against. It definitely is in bridges. Some of the
0:16:27 iconic designs in our country are incredible bridges. If we think of skylines as ensembles
0:16:32 of dreams realized, you spent quite a bit of time in New York. What do you love about
0:16:38 and what do you think about the New York City skyline? What’s a good picture? We’re looking
0:16:45 here at a few. I mean looking over the water. I think the water is an unbelievable feature
0:16:52 of the New York skyline. As you see the island on approach and oftentimes you’ll see like in
0:16:58 these images, you’ll see these towers reflecting off of the water surface. I think there’s something
0:17:07 very beautiful and unique about that. When I look at New York, I see this unbelievable tapestry
0:17:13 of different types of architecture. You have the Gothic form as represented by buildings like
0:17:20 the Woolworth building or you’ll have Art Deco as represented by buildings like 40 Wall Street or
0:17:26 the Chrysler building or Rockefeller Center and then you’ll have these unbelievable
0:17:32 super modern examples or modernist examples like Leverhouse and Seagram’s house. You have
0:17:38 all of these different styles and I think to build in New York, you’re really building the
0:17:45 best of the best. Nobody’s giving New York their second rate work and especially when a lot of
0:17:49 those buildings were built, there was this incredible competition happening between
0:17:57 New York and Chicago for kind of dominance of the sky and for who could create the greatest
0:18:02 skyline that’s sort of raced to the sky when skyscrapers were first being built starting
0:18:09 in Chicago and then New York surpassing that in terms of height at least with the Empire State
0:18:14 building. So I love sort of contextualizing the skylines as well and thinking back to
0:18:22 when different components that are so iconic were added in the context in which they came into
0:18:29 being. I got to ask you about this. There’s a pretty cool page that I’ve been following on X,
0:18:35 Architecture and Tradition and they celebrate sort of traditional schools of architecture
0:18:40 and you mentioned Gothic, the tapestry. This is in Chicago, the Tribune Tower in Chicago.
0:18:44 So what do you think about that sort of the old and then new mix together? Do you like Gothic?
0:18:48 I think it’s hard to look at something like the Tribune Tower and not be completely in awe.
0:18:53 I think this is an unbelievable building. Look at those buttresses and you’ve got
0:19:01 gargoyles hanging off of it and you know this style was reminiscent of the cathedrals of Europe
0:19:07 which was very kind of in vogue in like the 1920s here in America. Actually,
0:19:13 I mentioned the Woolworth Tower before. The Woolworth Tower was actually referred to as the
0:19:22 Cathedral of Commerce because it also was in that Gothic style. So this was built maybe a decade
0:19:30 before the Tribune Building but the Tribune Building to me is almost not replicable. It personally
0:19:35 really resonates with me because one of the first projects I ever worked on was building Trump
0:19:43 Chicago which was this beautiful, elegant, super modern, all glass skyscraper right across the way.
0:19:48 So it was right across the river. So I would look out the windows as it was under construction or
0:19:54 be standing quite literally on rebar of the building looking out at the Tribune and incredibly
0:20:01 inspired and now the reflective glass of the building reflects back not only the river but also
0:20:06 the Tribune Building and other buildings on Michigan Avenue.
0:20:11 Do you like it when the glass, the reflective properties of the glass as part of the architecture?
0:20:16 I think it depends. Like they have super reflective glass that sometimes doesn’t work. It’s distracting
0:20:24 and I think it’s one component of sort of a composition that comes together. I think in this
0:20:31 case the glass on Trump Chicago is very beautiful. It was designed by Adrian Smith of Skidmore Owing’s
0:20:38 in Maryland, a major architecture firm who actually did the Burj Khalifa in Dubai which is I think
0:20:46 like an awe-inspiring example of modern architecture. But glass is tricky. It’s you have to get the
0:20:52 shade right. You know some glass has a lot of iron in it and it gets super green and that’s
0:20:58 a choice and sometimes you have more blue properties, blue-silver like you see here,
0:21:03 but it’s part of the character. How do you know what it’s actually going to look like when it’s
0:21:07 done? Like is it possible to imagine that because it feels like there’s so many variables?
0:21:14 I think so. I think if you have a vivid imagination and if you sit with it and then if you also go
0:21:21 beyond the rendering, right, you have to live with the materials. So you don’t build a 92-story
0:21:30 building glass curtain wall and not deeply examine the actual curtain wall before purchasing it.
0:21:35 So you have to spend a lot of time with the actual materials, not just the beautiful sort
0:21:43 of artistic renderings, which can be incredibly misleading. The goal is actually that the end
0:21:50 result is much, much more compelling than what the architect or artist rendered, but
0:21:56 oftentimes that’s very much not the case. You know, sometimes also you mention context,
0:22:00 you know, sometimes I’ll see renderings of buildings. I’m like, wait, what about the building
0:22:06 right to the left of it that’s blocking 80% of its views? You know, architects will remove
0:22:13 things that are inconvenient, so you have to be rooted in reality.
0:22:20 Exactly. And I love the notion of living with the materials in contrast to living in the imagined
0:22:26 world of the drawings. So both are probably important because you have to dream the thing
0:22:30 into existence, but you also have to be rooted in like what the thing is actually going to look
0:22:34 like in the context of everything else. 100%. One of the underlying principles of the page
0:22:40 I just mentioned, and I hear folks mention this a lot, is that modern architecture is kind of
0:22:46 boring, that it lacks soul and beauty. And you just spoke with admiration for both modern
0:22:52 and for Gothic, for older architectures. So do you think there’s truth that modern architecture
0:23:00 is boring? I’m living in Miami currently, so I see a lot of super uninspired glass boxes
0:23:07 on the waterfront, but I think exceptional things shouldn’t be the norm. You know, they’re typically
0:23:15 rare. So, and I think in modern architecture, you find an abundance of amazing examples of
0:23:20 super compelling and innovative buildings designs. I mean, I mentioned the Burj Khalifa,
0:23:28 it is awe-inspiring. This is an unbelievably striking example of modern architecture. You look
0:23:34 at some older examples, the Sydney Opera House, and so I think there’s unbelievable, there you go.
0:23:40 I mean, it’s like a needle in the sky. Yeah, reaching out to the stars.
0:23:48 It’s huge, and in the context of a city where there’s a lot of height. So it’s unbelievable,
0:23:54 but I think one of the things that’s probably exciting me the most about architecture right now
0:24:00 is the innovation that’s happening within it. There’s example of robotic fabrication, there’s
0:24:08 3D printing. Your friend who you introduced me to not too long ago, Neri Oxman, which he’s doing at
0:24:16 the intersection of biology and technology, and thinking about how to create more sustainable
0:24:23 development practices, quite literally trying to create materials that will biodegrade back into
0:24:27 the earth. I think there’s something really cool happening now with the rediscovery of ancient
0:24:33 building techniques. So you have self-healing concrete that was used by the Romans, an art and
0:24:41 a practice of using volcanic ash and lime that’s now being rediscovered and is more critical than
0:24:47 ever as we think about how much of our infrastructure relies on concrete and how much of that is
0:24:53 failing on the most basic level. So I think actually it’s a really, really exciting time
0:25:01 for innovation in architecture. And I think there are some incredible examples of modern
0:25:09 design that are really exciting. But generally, I think Roosevelt said that comparison is the thief
0:25:14 of joy. So it’s hard. You look at the Tribune building, you look at some of these iconic structures.
0:25:20 One of the buildings I’m most proud to have worked on was the historical post office building
0:25:26 in Washington DC. You look at a building like that and it feels like it has no equal.
0:25:31 Also, there’s a psychological element where people tend to want to complain about the new
0:25:40 and celebrate the old. It’s like the history of time. People are always skeptical and concerned
0:25:45 about change. And it’s true that there’s a lot of stuff that’s new that’s not good. It’s not
0:25:50 going to last. It’s not going to stand the test of time, but some things will. And just like
0:25:57 in modern art and modern music, there’s going to be artists that stand the test of time and
0:26:02 we’ll later look back and celebrate them. Those are the good times. When you just step back,
0:26:06 what do you love about architecture? Is it the beauty? Is it the function?
0:26:12 I’m most emotionally drawn, obviously, to the beauty. But
0:26:19 I think as somebody who’s built things, I really believe that the form has to follow the function.
0:26:29 Like there’s nothing uglier than a space that is ill-conceived, that otherwise it’s decoration.
0:26:36 And I think that after sort of that initial reaction to seeing something that’s
0:26:44 aesthetically really pleasing to me when I look at a building or a project,
0:26:52 I love sort of thinking about how it’s being used. So having been able to build so many things
0:26:59 in my career and worked on so many incredible projects, I mean, it’s really, really rewarding
0:27:04 after the fact to have somebody come up to you and tell you that they got engaged in
0:27:11 in the lobby of your building or they got married in the ballroom and share with you
0:27:19 some of those experiences. So to me, that’s equally as beautiful, the use cases for these
0:27:30 unbelievable projects. But I think it’s all of it. I love that you’ve got the construction and you’ve
0:27:36 got the design and you’ve got then the interior design and you’ve got the financing elements,
0:27:43 the marketing elements, and it’s all wrapped up in this one effort. So to me, it’s exciting to
0:27:48 sort of flex in all those different ways. Yeah, like you said, it’s dreams realized, hard work
0:27:56 realized. I mean, probably on the bridge side is why I love the function in terms of function
0:28:04 being primary. You just think of like the millions of bridges. Go, go down. You had,
0:28:12 look at that. Yeah, this is Devil’s Bridge in Germany. Yeah, I wouldn’t say it’s like the most
0:28:17 practical design, but look how beautiful that is. Yeah, so this is probably, well, we don’t know.
0:28:21 We need to interview some people whether the function holds up, but in terms of beauty,
0:28:25 and then like what we’re talking about, using the water for the reflection
0:28:29 and the shape that creates, I mean, there’s an elegance to the shape of a bridge.
0:28:33 See, it’s interesting that they call it Devil’s Bridge because to me, this is
0:28:39 very ethereal. You know, I think about the ring, the circle, life.
0:28:43 There’s nothing about this that makes me feel, maybe they’re just being ironic
0:28:46 in the names. Once that function’s really flawed.
0:28:52 Yeah, exactly. Nobody’s ever successfully crossed the bridge yet. But I mean, to me,
0:28:57 there’s just iconic, I love looking at bridges because of the function. It’s the Brooklyn Bridge
0:29:00 or the Golden Gate Bridge. I mean, those are probably my favorites in the United States,
0:29:08 just in a city to be able to look out and see the skyline combined with the suspension bridge
0:29:14 and thinking of all the millions of cars that pass, like the busyness, like us humans getting
0:29:19 together and going to work, building cool stuff. And just the bridge kind of represents
0:29:25 the turmoil and the busyness of a city as it creates. It’s cool.
0:29:27 And the connectivity as well.
0:29:29 Yeah. The network of roads all come together.
0:29:35 So the bridge is the ultimate combination of function and beauty.
0:29:40 Yeah. I remember when I was first learning about bridges, studying the cable stay
0:29:47 versus the suspension bridge. And I mean, you actually built many replicas. So I’m sure you’ll
0:29:53 have a point of view on this, but they really are so beautiful. And you mentioned the Brooklyn
0:29:59 Bridge, but growing up in New York, that was as much a part of the architectural story
0:30:04 and tapestry of that skyline as any building that’s seen in it.
0:30:05 So.
0:30:11 What in general is your philosophy, philosophy of design, and building in architecture?
0:30:17 Well, some of the most recent projects I worked on prior to government service were the old
0:30:24 post office building and almost simultaneously Trump Dural in Miami. So these were both two
0:30:31 just massive undertakings, both redevelopments, which in a lot of cases, having worked on
0:30:37 ground up construction redevelopment projects are in a lot of ways much more complicated
0:30:44 because you have existing attributes, but also a lot of limitations you have to work within,
0:30:50 especially when you’re repurposing a use. So this, the old post office building on Pennsylvania
0:30:50 Avenue.
0:30:51 It’s so beautiful.
0:31:00 It’s unbelievable. So this was a Romanesque revival building built in the 1890s on America’s
0:31:08 main street to symbolize American grandeur. And at the time, there were post office being
0:31:13 built in the style across the country, but this being really the defining one still to this day,
0:31:19 the tallest habitable structure in Washington, the tallest structure being the monument,
0:31:24 the nation’s only vertical park, which is that clock tower, but you’ve got these thick granite
0:31:32 walls, those carved granite turrets, just an unbelievable building. You’ve got this massive
0:31:40 atrium that runs through the whole center of it that is topped with glass. So having the
0:31:46 opportunity to spearhead a project like that was so exciting. And actually, it was my first
0:31:53 renovation project. So I came to it with a tremendous amount of energy, vigor, and humility
0:32:00 about how to do it properly, ensuring I had all the right people. We had countless federal
0:32:06 and local government agencies that would oversee every single decision we made.
0:32:12 But in advance of even having the opportunity to do it, there was a close to two year request for
0:32:19 proposal, like a process that was put out by the General Services Administration. So it was this
0:32:26 really arduous government procurement process that we were competing against so many different
0:32:32 people for the opportunity, which a lot of people said it was a gigantic waste of time.
0:32:37 But I looked at that and I think so did a lot of the other bidders and say it’s worth trying to
0:32:41 put the best vision forward. So you fell in love with this project? I fell in love, yeah.
0:32:47 So is there some interesting details about what it takes to do renovation? Is there about some of
0:32:57 the challenges or opportunities because you want to maintain the beauty of the old and now upgrade
0:33:04 the functionality, I guess, and maybe modernize some aspects of it without destroying
0:33:11 what made the building magical in the first place? So I think the greatest asset was already there,
0:33:19 the exterior of the building, which we meticulously restored and any addition to it had to be done
0:33:29 sort of very gently in terms of any signage additions. And the interior spaces were completely
0:33:36 dilapidated. It had been in a post office then we was used for a really rundown food court and
0:33:46 government office spaces. It was actually losing $6 million a year when we got the concession to
0:33:52 build it and when we won and became one of I think a great example of public-private partnerships
0:33:58 working together. But I think the biggest challenge in having such a radical use conversion
0:34:05 is just how you lay it out. So the amount of time I would get on that excella
0:34:12 twice a week, three times a week to spend eight trips down in Washington and we would walk every
0:34:18 single inch of the building, laying out the floor plans, debating over the configuration of a room.
0:34:24 There were almost 300 rooms and there were almost 300 layouts. So nothing could be repeated.
0:34:33 Whereas when you’re building from scratch, you have a box and you decide where you want to add
0:34:40 potential elements and you kind of can stack the floor plan all the way up. But when you’re
0:34:45 working within a building like this, every single room was different. You see the setback. So the
0:34:54 setback then required you to move the plumbing. So it was really a labor of love and to do something
0:34:58 like this. And that’s why I think renovation. We had it with Durral as well. It was 700
0:35:09 rooms over 650 acres of property. And so every single unit was very different and complicated,
0:35:16 not as complicated in some ways. The scale of it was so massive, but not as complicated as the
0:35:21 old post office, but it required a level of precision. And I think in real estate, you have a lot of
0:35:30 people who design on plan and a lot of people who are in the business of acquiring and flipping.
0:35:39 So it’s more financial engineering than it is building. And they don’t spend the time sort of
0:35:44 sweating these details. It makes something great and makes something functional and you feel it in
0:35:51 the end result. But I mean, blood, sweat, tears, years of my life for those projects. And it was
0:35:58 worth it. I enjoyed almost. I enjoyed almost every minute of it. So to you, it’s not about the
0:36:04 flipping. It’s about the art and the function of the thing that you’re creating. 100%.
0:36:13 What’s design on plan? I’m learning new things today. When proposals are put forth by an architect
0:36:18 and really just the plan is accepted. And in the case of a renovation, if you’re not walking
0:36:24 those rooms, the number of times a beautifully laid out room was on a blueprint. And then I’d go to
0:36:30 Washington and I’d walk that floor and I’d realize that there was a column that ran right up through
0:36:36 the middle of the space where the bed was supposed to be or the toilet was supposed to be or the
0:36:45 shower. So there’s a lot of things that are missed when you do something conceptually
0:36:51 without sort of rooting it in the actual structure. And that’s why I think even with ground
0:36:55 up construction as well, people who aren’t constantly on their job sites, constantly
0:37:04 walking the projects, there’s just a lot that’s missed. I mean, there’s a wisdom to the idea
0:37:09 that we talked about before, live with the materials and walking the construction site,
0:37:14 walking the rooms. I mean, that’s what you hear from people like Steve Jobs, like Elon. That’s
0:37:21 why you live on the factory floor. That’s why you constantly obsess about the details, the actual,
0:37:27 not of the plans, but the physical reality of the product. I mean, the insanity of Steve Jobs
0:37:33 and Johnny and I working together on making it perfect, making the iPhone, the early designs,
0:37:39 prototypes, making that perfect, like what it actually feels like in the hand. You have to be
0:37:46 there as close to the metal as possible to truly understand. And you have to love it in order
0:37:51 to do that. Right. It shouldn’t be about how much it’s going to sell for and all that kind of stuff.
0:37:56 You have to love the art. Because for the most part, you can probably get 90, maybe 95% of the end
0:38:05 result, unless something has terribly gone awry by not caring with that level of almost like
0:38:15 maniacal precision. But you’ll notice that 10% for the rest of your life. So I think that extra
0:38:23 effort, that passion, I think that’s what separates good from great. If we go back to that young
0:38:31 Ivanka, the confidence of youth, and if we could talk about your mom, she had a big influence on
0:38:39 you. You told me she was an adventurer, Olympic skier and a businesswoman. What did you learn
0:38:51 about life from your mother? So much. She passed away two years ago now. And she was a remarkable,
0:38:58 remarkable woman. She was a trailblazer in so many different ways. As an athlete and growing up in
0:39:07 Communist Czechoslovakia as a fashion mogul, as a real estate executive and builder, just this
0:39:14 all around trailblazing businesswomen. I also learned from her, aside from that element,
0:39:21 how to really enjoy life. I look back and some of my happiest memories of her are
0:39:28 in the ocean, just lying on our back, looking up at the sun and just so
0:39:37 in the moment or dancing. She loved to dance. She really taught me a lot about living life to its
0:39:46 fullest. She had so much courage, so much conviction, so much energy and a complete comfort with who
0:39:53 she was. What do you think about that? I mean, Olympic athlete, the trade-off between ambition
0:39:59 and just wanting to do big things and pursuing that and giving your all to that and being able to
0:40:08 relax and just throw your arms back and enjoy every moment of life, that trade-off. What do
0:40:16 you think about that trade-off? I think because she was this unbelievable, formidable athlete and
0:40:23 because of the discipline she had as a child, I think it made her value those moments more as an
0:40:29 adult. I think she was a great balance of the two that we all hoped to find and she was able
0:40:36 to find both incredibly serious and formidable. I remember as a little girl, I used to literally
0:40:44 traipse behind her at the Plaza Hotel, which she oversaw and actually kind of was her old
0:40:51 post office. It was this unbelievable historic hotel in New York City. I’d follow her around
0:40:59 at construction meetings and on job sites and there she is dancing. See? That’s funny that
0:41:03 that’s the picture you pull up. I’m sorry, the two of you just look great in that picture.
0:41:13 That’s great. She had such a joy to her and she was so unabashed in her perspective and her
0:41:21 opinions. She made my father look reserved. Whatever she was feeling, she was just very
0:41:28 expressive and a lot of fun to be around. She, as you mentioned, grew up during the Prague Spring
0:41:36 in 1968 and that had a big impact on human history. My family came from the Soviet Union
0:41:43 and then the 20th century, the story of the 20th century is a lot of Eastern Europe,
0:41:53 the Soviet Union, tried the ideas of communism and it turned out that a lot of those ideas
0:41:59 resulted into a lot of suffering. What do you think the communist ideology failed?
0:42:08 I think fundamentally, as people we desire freedom, we want agency. My mom was a lot of
0:42:13 other people who grew up in similar situations where she didn’t like to talk about it that often.
0:42:21 One of my real regrets is that I didn’t push her harder. I think back to the conversations we
0:42:28 did have and I try to imagine what it’s like. She was at Charles University in Prague, which was
0:42:37 really like a focal point of the reforms that were ushered in during the Prague Spring and
0:42:42 the liberalization agenda that was happening. The dance halls were opening, the student activists
0:42:50 and she was attending university there right at that same time. The contrast to this feeling of
0:43:01 freedom and progress and liberalization in the spring and then it’s so quickly being crushed
0:43:09 in the fall of that same year when Warsaw Pact countries and the Soviet Union rolled in to
0:43:16 put down and ultimately roll back all those reforms. For her to have lived through that,
0:43:27 she didn’t come to North America until she was 23 or 24. That was her life. As a young girl,
0:43:34 she was on the junior national ski team for Czechoslovakia. My grandfather used to train her.
0:43:40 They used to put the skis on her back and walk up the mountain in Czechoslovakia because there
0:43:47 were no ski lifts. She actually made me do that when I was a child just to let me know what her
0:43:52 experience had been. If I complained that it was cold out, she’s like, “Well, you didn’t have to
0:43:56 walk up the mountain. You’d be plenty warm if you had carried the skis up on your back
0:44:02 up the last run.” I feel like they made people tougher back then. My grandfather,
0:44:08 and you mentioned it’s funny, they go through some of the darkest things that a human being can go
0:44:14 through and they don’t talk about it. They have a general positive outlook on life that’s deeply
0:44:23 rooted in the knowledge of what life could be, like how bad it could get. My grandma survived
0:44:31 Haldemur in Ukraine, which was a mass starvation brought on by the collectivist policies of the
0:44:36 Stalin regime. Then she survived the Nazi occupation of Ukraine, never talked about it,
0:44:44 probably went through extremely dark, extremely difficult times and then just always had a positive
0:44:51 outlook on life and also made me do very difficult physical activity. Just imagine,
0:44:57 just to humble you. Kids these days are soft kind of energy, which I’m deeply, deeply grateful for.
0:45:04 On all fronts, including just having hardship and including just physical hardship flung at me,
0:45:10 I think that’s really important. You wonder how much of who they were was a reaction to their
0:45:17 experience. Would she have naturally had that sort of forward-looking, grateful, optimistic
0:45:23 orientation? Or was it a reaction to our childhood? I think about that. I look at this picture of my
0:45:32 mom and she was unabashedly herself. She loved flamboyance and glamour and in some ways, I think
0:45:40 it probably was a direct reaction to this very austere control childhood. This was one expression
0:45:47 of it. I think how she dressed and how she presented, I think her entrepreneurial spirit
0:45:53 and love of capitalism and all things American was another manifestation of it and one that I
0:46:02 grew up with. I remember the story she used to tell me about when she was 14 and she was going,
0:46:11 to neighbouring countries. As an athlete, you were given additional freedoms that you wouldn’t
0:46:20 otherwise be afforded in these societies under communist rules. She was able to travel where
0:46:25 most of her friends never would be able to leave Czechoslovakia. She would come back from all of
0:46:31 these trips and the first place where she’d do ski races in Austria and elsewhere. The first thing
0:46:38 she had to do was check in at the local police. She’d sit down and she had enough wisdom at 14
0:46:45 to know that she couldn’t appear to be lying by not being impressed by what she saw and the fact
0:46:50 that you could get an orange in the winter, but she couldn’t be too excited by it that she’d become
0:46:59 a flight risk. Give enough details that you’re believable but not so many that you’re not trusted.
0:47:09 Imagine that as a 14-year-old, that experience and having to navigate the world that way. She
0:47:15 told me that eventually all those local police officers, they came to love her because one of
0:47:19 the things she’d do is smuggle that stuff back from these countries and give it to them to give
0:47:28 their wives perfume and stockings. She figured out the system pretty quickly, but it’s a very
0:47:34 different experience from what I was navigating and the pressures and challenges me as a 14-year
0:47:40 old was dealing with. I have so much respect and admiration for her.
0:47:46 Yeah, hardship clarifies what’s important in life. You know, I’ve talked about man’s search for meaning,
0:47:55 that book, having an ultimate hardship clarifies that finding joy in life is not about the
0:48:01 environment, it’s about your outlook on that environment. There’s beauty to be found in any
0:48:07 situation and also in that particular situation, when everything is taken from you, the thing you
0:48:13 start to think about is the people you love. In the case of man’s search for meaning, Victor
0:48:20 Franco thinking about his wife and how much he loves her. That love was the flame, the warmth
0:48:25 that kept him excited. The fun thing to think about when everything else is gone. We sometimes
0:48:29 forget that with the business of life and get all this fun stuff we’re talking about, like building
0:48:34 and being a creative force in the world. At the end of the day, what matters is just the other
0:48:40 humans in your life, the people you love. It’s the simple stuff. Victor Franco is somebody,
0:48:48 I mean, his, that book and just his philosophy in general is so inspiring to me, but I think
0:48:53 so many people, they say they want happiness, but they want conditional happiness. When this
0:48:58 and this, a thing happens or under these circumstances, then I’ll be happy. I think
0:49:07 what he showed is that we can sort of cultivate these virtues within ourselves regardless of
0:49:14 the situation we find ourselves in. In some ways, I think the meaning of life is the search for
0:49:20 meaning in life. It’s the relationships we have and we form. It’s the experience we have. It’s
0:49:27 how we deal with the suffering that life inevitably presents to us. Victor Franco does
0:49:35 an amazing job highlighting that under the most horrific circumstances, and I think it’s just
0:49:41 super inspiring to me. He also shows that you can get so much from just small joys,
0:49:47 like getting a little more soup today than you did yesterday. I mean, it’s the little stuff.
0:49:54 If you allow yourself to love the little stuff of life, it’s all around you. It’s all there.
0:49:59 So you don’t need to have these ambitious goals and the comparison being a thief of joy, that
0:50:04 kind of stuff. Just like it’s all around us, the ability to eat. When I was in the jungle,
0:50:10 and I got severely dehydrated because there’s no water, you run out of water real quick,
0:50:20 and the joy I felt when I got the drink. I didn’t care about anything else. Speaking of
0:50:25 things that matter in life, I always started to fantasize about water. That was bringing me joy.
0:50:32 You can tap into this feeling at any time. Exactly. I was just tapping in just to stay
0:50:35 positive. Just go into your bathroom, turn on the sink, and watch the water.
0:50:42 Oh, for sure. I mean, people really, it’s good to have stuff taken away for a time.
0:50:48 That’s why struggle is good, to make you appreciate, to have a deep gratitude for when you have it.
0:50:54 And water and food is a big one, but water is the biggest one. I wouldn’t recommend it necessarily
0:50:58 to get severely dehydrated to appreciate water, but maybe every time you take a sip of water,
0:51:03 you can have that kind of gratitude. There’s a prayer in Judaism you’re supposed to say every
0:51:13 morning, which is basically thanking God for your body working. It’s something so basic,
0:51:19 but it’s when it doesn’t that we’re grateful. So just reminding ourselves every day, the basic
0:51:29 things of a functional body, of our health, of access to water, which so many millions of people
0:51:36 around the world do not have reliably, is very clarifying and super important.
0:51:42 Yeah, health is a gift. Water is a gift. Is there a memory with your mom that
0:51:48 had a defining effect on your life? I have these vignettes in my mind,
0:52:00 seeing her in action in different capacities. A lot of times, in the context of things that
0:52:06 I would later go on to do myself, so I would go every day, almost every day after school,
0:52:11 and I’d go to the Plaza Hotel and I’d follow her around as she’d walk the hallways and just
0:52:17 observe her. And she was so impossibly glamorous. She was doing everything in four and a half inch
0:52:27 heels with this bouffant. So it’s almost like an inaccessible visual, but I think for me,
0:52:35 when I saw her experience, the most joy tended to be by the sea. Almost always, not a pool. And I
0:52:43 think I get this from her. I say, “Pools, they’re fine.” I love motion. I love salt water. I love
0:52:50 the way it makes me feel. And I think I got that from her. So we would just swim together all the
0:52:58 time. And it’s a lot of what I love about Miami, actually, being so close to the ocean. I find
0:53:05 it to be super cathartic. But a lot of my memories of my mom seeing her really just
0:53:12 in her bliss is floating around in a body of salt water.
0:53:16 Is there also some aspect to her being an example of somebody that could be
0:53:22 sort of beautiful and feminine, but at the same time powerful, a successful businesswoman
0:53:29 that showed it as possible to do that? Yeah, I think she really was a trailblazer. It’s not
0:53:36 uncommon in real estate for there to be multiple generations of people. And so on job sites,
0:53:43 it was not unusual for me to run into somebody whose grandfather had worked with my grandfather
0:53:50 and Brooklyn or Queens or whose father had worked with my mother. And they’d always tell me these
0:53:56 stories about her rolling in and they’d hear the heels first. And a lot of times, the story would
0:54:02 be like, “Oh, gosh, really, it’s two days after Christmas. We thought we’d get a reprieve.”
0:54:11 But she was very exacting. So I have this visual in my mind of her walking on rebar
0:54:16 on the balls of her feet in these foreign shields. I’m assuming she actually carried
0:54:25 flats with her, but I don’t know. That’s not the visual I have. But I loved the fact that
0:54:37 she so embodied femininity and glamour and was so comfortable being tough and ambitious and
0:54:45 determined and this unbelievable businesswoman and entrepreneur at a time when she was very much
0:54:51 alone, even for me in the development world and so many of the different businesses that I’ve been
0:54:57 in, there really aren’t women outside of sales and of marketing. You don’t see as many women in
0:55:04 the development space and the construction space, even in the architecture and design space,
0:55:13 maybe outside of interior design. And she was decades ahead of me. So I love hearing these
0:55:20 stories. I love hearing somebody who’s my peer tell me about their grandfather and their father
0:55:25 and their experience with one of my parents. It’s amazing. And she did it all in foreign
0:55:32 shields. She used to say, “There’s nothing that I can’t do better in heels.” That would be
0:55:36 your exact thing. And when I complained about wearing something, it was like
0:55:46 the early ’90s, everything was also uncomfortable, these fabrics and materials. And I would go back
0:55:54 and forth between being super girly and a total tomboy. But she’d dress me up in these things
0:55:59 and I’d be complaining about it. And she’d say, “Yvanka, pain for beauty,” which I happen to totally
0:56:04 disagree with because I think there’s nothing worse than being uncomfortable. So I haven’t
0:56:13 accepted or internalized all of this wisdom, so to speak, but it was just funny. She had
0:56:18 a very specific point of view. And full of good lines, “Pain for beauty.”
0:56:24 It’s funny because just even in fashion, if something’s uncomfortable, to me,
0:56:29 there’s nothing that looks worse than when you see somebody tottering around and their heels
0:56:36 hurt them. So they’re walking oddly. They’re not embodying their confidence in that regard.
0:56:39 So I’m kind of the opposite. I start with, “Well, I want to be comfortable.”
0:56:46 And that helps me be confident and in command. A foundation for fashion for you is comfort.
0:56:50 And on top of that, you build things that are beautiful. And it’s not comfort, like,
0:56:55 dowdy. There’s that level of comfort. Functional comfort. But I think you have to, for me,
0:57:01 I want to feel confident. And you don’t feel confident when you’re pulling at a garment
0:57:08 or hobbling on heels that don’t fit you properly. And she was never doing those things either. So
0:57:11 I don’t know how she was wearing stuff like that. That’s like a 40-pound bead of dress. And I know
0:57:19 this because I have it. And I wore it recently. And I mean, I got a workout walking to the elevator.
0:57:23 Like, this is a heavy dress. And you know what? It was worth it. It was great.
0:57:25 Yeah. She’s making it look easy.
0:57:28 But she makes it look very, very easy. So…
0:57:30 Do you miss her?
0:57:39 I’m so much. It’s unbelievable how dislocating the loss of a parent is. And
0:57:50 her mother lives with me, still. My grandmother, who helped raise us. So that’s very special.
0:57:56 And I can ask her some of the questions that I would have… Sorry. I wanted to ask my own mom,
0:58:03 but it’s hard. It was beautiful to see. I’ve gotten a chance to spend time
0:58:11 with your family to see so many generations together at the table. And there’s so much history there.
0:58:21 She’s 97. And until she was around 94, she lived completely on her own. No help, no anything, no support.
0:58:31 And now she requires really sort of 24-hour care. And I feel super grateful that I’m able
0:58:37 to give her that because that’s what she did for me. It’s amazing for me to have my children be
0:58:46 able to grow up and know her stories, know her recipes, check dumplings and goulash. And
0:58:51 Kitsulitsa and all the other things she used to make me in my childhood. But she really,
0:58:59 she was a major force in my life, my grandmother. My mom was working. So my grandmother was the
0:59:06 person who was always home every day when I came back from school. And I remember I used to shower,
0:59:13 and it would almost be comical. I feel like in my memory, and there is no washing machine I’ve seen
0:59:19 on the planet that can actually do this. But in my memory, I’d go to shower, and I’d drop something
0:59:24 on the bed, and I’d come back into the room after my shower, and it was like folded, pressed. It was
0:59:31 all my grandmother. She’s like running after me, taking care of me. And so it’s nice to be able
0:59:42 to do that for her. I got from her reading. My grandmother, she devoured books. She loved the
0:59:49 more sensational ones. So some of these romance novels that would pick them up, the covers.
0:59:56 But she could tell you, she could look at any royal lineage across Europe and tell you all the
1:00:04 mistresses, all the drama. She loved it. But her face was always buried in a book. My grandfather,
1:00:14 Ditto, he was the athlete. He swam professionally on the national team for Czechoslovakia, and he
1:00:18 helped train my mom, as I was saying before, in skiing. So he was a great athlete, and she was
1:00:26 at home, and she would read and cook. And so that’s something I remember a lot from my childhood,
1:00:33 and she would always say, I got reading from her. Speaking of drama, I had my English teacher in
1:00:38 high school recommend a book from me by D.H. Florence. It’s supposed to be a classic. She’s
1:00:43 like, this is a classic you should read. It’s called “Lady Shatter A’s Lover.” And
1:00:49 I’ve read a lot of classics, but that one is straight up like a romance novel about a wife
1:00:54 we like just cheating with a gardener. And I remember reading this like, what? Like in retrospect,
1:01:00 I understand why it’s a classic because it was so scandalous to talk about sex in a book 100
1:01:04 years ago, or whatever. In retrospect, do you know why she recommended it to you? I don’t know.
1:01:10 I think she’s just sending a signal, hey, you need to get out more or something. I don’t know.
1:01:19 Maybe she was seeking to inspire you. Exactly. Anyway, I mean, I love that kind of stuff too,
1:01:25 but I love all the classics. And they get, there’s a lot of drama, human nature,
1:01:31 drama is part of it. So what about your dad growing up? What did you learn about life from
1:01:38 your father? I think my father’s sense of humor is sometimes underappreciated. So he had an amazing
1:01:45 and has an amazing sense of humor. He loved music. I think my mom loved music as well, but
1:01:51 you know, my father always used to say that in another life he would have been a Broadway musical
1:01:57 producer, which is hilarious to think about, but he loves, he loves music.
1:02:05 That is funny to think about. Right. Now he DJs at Mar-a-Lago. So people get a sense of,
1:02:12 he loves Andrew Lloyd Webber and all of it, Pavarotti, Elton John. I mean, these were the
1:02:19 same songs on repeat my whole childhood. So I know the playlist. Probably Sinatra and all that.
1:02:26 Love Sinatra. Love Elvis. You know, a lot of the greats. So I think I got a little bit of my love
1:02:34 from music from him, but my mom shared that as well. I think one of the things, you know, in
1:02:39 looking back that I think I inherited from my father as well is this sort of
1:02:48 interest or understanding of the importance of asking questions and specifically questions of
1:02:55 the right people. And I saw this a lot on job sites. So I remember with the old post office
1:03:02 building, there was this massive glass topped atrium. So heating and cooling the structure
1:03:10 was like a Herculean lift. We had the mechanical engineers provide their thoughts on how we could
1:03:18 do it efficiently and so that the temperature never varied. And it was enormously expensive
1:03:25 as an undertaking. And I remember one of his first times on the site because, you know,
1:03:30 he had really empowered me with this project and he trusted me to execute and to also,
1:03:35 you know, rope him in when I needed it. But one of the first time he visits, we’re walking the
1:03:40 hallway and we’re talking about how expensive this cooling system would be and heating system
1:03:48 would be. And he starts stopping and he’s asking duct workers as we walk what they think of the
1:03:54 system that the mechanical engineers designed. First few, fine, you know, not great answers.
1:03:59 The third guy goes, “Sir, if you want me to be honest with you, it’s obscenely over designed.”
1:04:08 In the circumstance of a 1,000-year storm, you will have the exact perfect temperature
1:04:14 if there’s a massive blizzard or if it’s unbearably hot, but 99.9% of the time you’ll never need it.
1:04:22 And so I think it’s just an enormous waste of money. And so he kept asking that guy questions
1:04:28 and we ended up overhauling the design pretty well into the process of the whole system,
1:04:34 saving a lot of money, creating a great system that’s super functional. And so I learned a lot,
1:04:38 and that’s just one example of countless. That one really sticks out in my head because I’m like,
1:04:43 “Oh my gosh, we’re redesigning the whole system.” You know, we were actively under construction.
1:04:52 But I would see him do that on a lot of different issues. He would ask people on the work level
1:04:59 what their thoughts were, ideas, concepts, designs. And there was almost like a Socratic
1:05:08 sort of first principles type of way he questioned people, trying to get down to sort of
1:05:14 trying to reduce complex things to something really fundamental and simple.
1:05:20 So I try to do that myself to the best I can. And I think it’s something I very much learned
1:05:26 from him. Yeah, I’ve seen great engineers, great leaders do just that. You see, you want to do
1:05:34 that a lot, which is basically ask questions to push simplification. So can we do the simpler?
1:05:39 The basic question is like, why are we doing it this way? Can this be done simpler?
1:05:44 And not taking as an answer that this is how we’ve always done it.
1:05:51 Not allowing yourself. It doesn’t matter that’s how it was done it. What is the right way to do
1:05:58 it? And usually the simpler it is, the more correct the way. It has to do with costs,
1:06:03 it has to do with simplicity of production manufacture, but usually simple is best.
1:06:08 And it’s oftentimes not the architecture, the engineers. It’s, you know, in Elon’s case,
1:06:14 probably the line worker who sees things more clearly. So I think making sure it’s not just
1:06:19 that you’re asking good questions, you’re asking the right people, those same good questions.
1:06:25 That’s why a lot of the Elon companies are really flat in terms of organizational design where
1:06:34 the, anybody on the factory floor can talk directly to Elon. There’s not this managerial
1:06:39 class, this hierarchy where to travel up and down the hierarchy, which large companies often
1:06:46 construct this hierarchy of managers where no one manager, if you ask them the question of
1:06:50 like, what have you done this week? The answer is like, it’s really hard to come up with.
1:06:55 Usually it’s going to be a bunch of paperwork. Yeah. So you’re like, nobody knows what they
1:07:01 actually do. So when it’s flat, you can actually get as quickly as possible. When problems arise,
1:07:08 you can solve those problems as quickly as possible. And also you have a direct, rapid,
1:07:14 iterative process where you’re making things simpler, making them more efficient and constantly
1:07:19 improving. So yeah, it’s interesting. Well, when large, I mean, you see this in government,
1:07:26 a lot of people get together, a hierarchy is developed and that somehow sometimes it’s good,
1:07:31 but very often just slows things down. And you see great companies, great, great companies,
1:07:39 Apple, Google, Meta, they have to fight against that bureaucracy that builds,
1:07:44 the slowness that large organizations have. And to still be a big organization and act
1:07:50 like a startup is the big challenge. It’s super difficult to deconstruct that as well once it’s
1:07:58 in place, right? It’s circumventing layers and asking questions, probing questions of people
1:08:05 on the ground level is a huge challenge to the authority of the hierarchy. And there’s
1:08:11 tremendous amount of resistance to it. So it’s how do you grow something in the case of a company,
1:08:22 in terms of a culture that can scale, but doesn’t lose its connection to sort of real and meaningful
1:08:29 feedback? It’s not easy. I’ve had a lot of conversations with Jim Keller, who’s this legendary
1:08:36 engineer and leader. And he has talked about, you often have to kind of be a little bit of
1:08:43 an asshole in the room, not in a mean way, but it’s uncomfortable. A lot of these questions,
1:08:48 they’re uncomfortable, they break the kind of general politeness and civility that people
1:08:55 have in communication. When you get a meeting, nobody wants to be like, can we do it way different?
1:09:03 Everyone wants just like, this lunch is coming up. I have this trip planned on the weekend
1:09:09 with the family. Everyone just wants comfort. When humans get together, they kind of gravitate
1:09:15 towards comfort. Nobody wants that one person that comes in and says, hey, can we do this way
1:09:20 better and way different? And everything we’ve gotten comfortable with, throw it out. Not only
1:09:24 do they not want that, but the one person who comes in and does that puts a massive target on
1:09:32 their back and is ultimately seen as a threat. I mean, nobody really gets fired for maintaining
1:09:38 the status quo. Even if things go poorly, it’s the way it was always done. Yeah, humans are
1:09:46 fascinating. But in order to actually do great big projects to reach for the stars, you have to
1:09:52 have those people. You have to constantly disrupt and have those uncomfortable conversations.
1:09:58 And really have that first principles type of orientation, especially in those large bureaucratic
1:10:05 contexts. So amongst many other things, you created a fashion brand. What was that about?
1:10:14 What was the origin of that? I always loved fashion as a form of self-expression,
1:10:20 as a means to communicate either a truth or an illusion, depending on what kind of mood you’re
1:10:26 in, but this like sort of second body, if you will. So I loved fashion. And look, I mean,
1:10:32 my mother was a big part of the reason I did, but I never thought I would go into fashion.
1:10:38 In fact, I was graduating from Wharton. It was the day of my graduation. And a winter calls
1:10:47 me up and offered me a job at Vogue, which is a dream in so many ways. But I was so focused. I
1:10:53 wanted to go into real estate, and I wanted to build buildings. And I told her that. So I really
1:11:00 thought that that was going to be the path I was taking. And then very organically fashion,
1:11:07 you know, it was part of my life, but it came into my life in a more professional capacity
1:11:15 by talking with my first of many different partners that I had in the fashion space about.
1:11:21 He actually had shown me a building to buy. His family had some real estate holdings, and
1:11:26 I passed on the real estate deal, but we forged a friendship. And we started talking about
1:11:36 how in the space that he was in, fine jewelry, there was this lack of product and brands that
1:11:42 were positioned for self-purchasing females. So everything was about the man buying the Christmas
1:11:46 gift, the man buying the engagement ring. The stores felt like that. They were all tailored
1:11:52 towards the male aesthetic. The marketing felt like that. And what about the woman who had a
1:11:58 salary and was really excited to buy herself a great pair of earrings or had just received a
1:12:03 great bonus and was going to use it to treat herself? So we thought there was a void in the
1:12:10 marketplace. And that was the first category I launched, Ivanka Trump Fine Jewelry. And
1:12:15 we just caught lightning in a bottle. It was really quickly after that, I met my partner
1:12:22 who had founded Nine West Shoes, a really capable partner. And we launched a shoe collection,
1:12:28 which took off and did enormously well. And then a clothing collection and handbags and
1:12:40 sunglasses and fragrance. So we caught a moment. And we found a positioning for the self-purchasing
1:12:47 multi-dimensional woman. And we made dressing for work aspirational. At the time we launched,
1:12:53 if you wanted to buy something for an office context, the brands that existed were the
1:12:59 opposite of exciting. Nobody was taking pictures of what they were wearing to work and
1:13:06 posting it online with some of these classic legacy brands. Really, it felt very much like it was
1:13:11 designed by a team of men for what a woman would want to wear to the office. So we started creating
1:13:15 this clothing that was feminine, that was beautiful, that was versatile, that would take
1:13:24 a woman from the boardroom to an after-school soccer game, to a date night with a boyfriend,
1:13:30 to a walk in the park with their husband, all the different ways women live their lives and
1:13:38 creating a wardrobe for that woman who works at every aspect of their life, not just sort of the
1:13:45 siloed professional part. And it was really compelling. We started creating great brand
1:13:53 content. And we had incredible contributors like Adam Grant, who was blogging for us at the time,
1:13:59 and creating aspirational content for working women. It was actually kind of a funny story,
1:14:05 but I now had probably close to 11 different product categories, and we were growing like
1:14:10 wildfire. And I started to think about what would be a compelling way to sort of create
1:14:17 interesting content for the people who are buying these different categories. And we came up with
1:14:22 a website called Women Who Work. And I went to a marketing agency, one of the fancy firms in New
1:14:27 York, and I said, “We want to create a brand campaign around this multidimensional woman who
1:14:33 works. And what do you think? Can you help us?” And they come back and they say, “You know what?
1:14:40 We don’t like the word work. We think it should be women who do.” And I just started laughing because
1:14:46 I’m like, “Women who do?” And the fact that they couldn’t conceive of it being sort of exciting
1:14:54 and aspirational and interesting to sort of lean into working at all aspects of our lives
1:15:00 was just fascinating to me, but that was part of the problem. And I think that’s why ultimately,
1:15:06 I mean, when the business grew to be hundreds of millions of dollars in sales, we were distributed
1:15:12 at all the best retailers across the country from Neiman Marcus to Saks to Bloomingdale’s
1:15:19 and beyond. And I think it really resonated with people in an amazing way and probably not
1:15:27 dissimilar to how I have this incredible experience. Every time somebody comes up to me and
1:15:37 tells me that they were married in a space that I had painstakingly designed, I have that experience
1:15:43 now with my fashion company. The number of women who will come up tell me that they loved my shoes
1:15:48 or they loved the handbags. And I’ve had women show me their engagement rings. They got engaged
1:15:53 with us. And it’s really rewarding. It’s really beautiful. Yeah, when I was hanging out with
1:16:00 you in Miami, the number of women that came up to you saying they love the clothing, they love
1:16:04 the shoes is awesome. All these years later. All these years later. Yeah. What does it take
1:16:11 to make a shoe where somebody would come up to you years later and just be just full of love
1:16:15 for this thing you’ve created? What’s that mean? Like, what does it take to do that?
1:16:20 Well, I still wear the shoes. I mean, that’s a good starting point, right? Is
1:16:26 it create a thing that you want to wear? I feel like the product, I think first and foremost,
1:16:31 you have to have the right partner. So shoe, building a shoe, if you talk to a great shoe
1:16:36 designer, it’s like, it’s architecture. Like making a heel that’s four inches that feels
1:16:43 good to walk in for eight hours a day. That is an engineering feat. And so I found great partners
1:16:48 in everything that I did. My shoe partner had founded Nine West. So he really knew
1:16:52 what went into making a shoe wearable and comfortable. And then you overlay that with
1:17:00 great design. And we also created this really comfortable, beautifully designed, super feminine
1:17:07 product offering that was also affordably priced. So I think it was like the trifecta of those
1:17:15 three things that made it stand out for so many people. Can you speak to, I don’t know if it’s
1:17:22 possible to articulate, but can you speak to the process you go through from idea to the final thing,
1:17:28 like what you go through to bring an idea to life? So not being a designer, and this was true in
1:17:33 real estate as well. I was never the architect. So I didn’t necessarily have the pen and in
1:17:39 fashion the same. I was kind of like a conductor. I knew what I liked and didn’t like. And I think
1:17:45 that’s really important. And that became honed for me over time. So I would have to sit a lot
1:17:53 longer with something earlier on than later when I had more refined my aesthetic point of view.
1:18:01 And so I think, first of all, you have to have a pretty strong sense of what resonates with you.
1:18:09 And then as in the case of my fashion business, as it grew and became quite a large business,
1:18:13 and I had so many different categories, everything had to work together. So I had individual partners
1:18:18 for each category. But if we were selling at Neiman Marcus, we couldn’t have a pair of shoes that
1:18:24 didn’t relate to a dress that didn’t relate to a pair of sunglasses and handbags all on the same
1:18:32 floor. So in the beginning, it was much more collaborative. As time passed, I really sort of
1:18:36 took the point on deciding, and this is the aesthetic for the season. These are the colors
1:18:42 we’re going to use. These are fabrics. And then working with our partners on the execution of
1:18:49 that. But I needed to create an overlay that allowed for cohesion as the collection grew.
1:18:54 And that was actually really fun for me because that was a little different. I was typically
1:19:01 initially responding to things that were put in front of me. And towards the end, it was my
1:19:09 partners who were responding to the things that myself and my team. But I always wanted to bring
1:19:17 the best talent. And so I was hiring great designers and printmakers and copywriters.
1:19:25 And so I had this almost like that conductor analogy. I had this incredible group of, in this
1:19:34 case, women assembled who had very strong points of view themselves. And it created a great team.
1:19:40 So yeah, I mean, great team is really sort of essential. It’s the essential thing behind any
1:19:47 successful story. But there’s this thing of taste, which is really interesting. It’s hard to kind of
1:19:55 articulate what it takes, but basically knowing A versus B, what looks good. Or without A/B comparison
1:20:03 to say like, if we did, if we changed this part, that would make it better. That sort of designer
1:20:11 taste, it’s hard to make explicit what that is. But the great designers like have that taste,
1:20:16 like this is going to look good. And it’s not actually, again, Steve Jobs thing is not the
1:20:22 opinion, like you can’t pull people and ask them what looks better. You have to have the vision
1:20:30 of that. And as you said, you also have to develop eventually the confidence that your taste is good
1:20:37 such that you can curate, you can direct teams, you can argue that no, no, no, this is right.
1:20:41 Even when there’s several people that say this doesn’t make any sense. If you have that vision,
1:20:46 have the confidence, this will look good. That’s how you come up with great designs.
1:20:50 It’s a mixture of great taste as you develop over time and the confidence.
1:20:57 And that’s a really hard thing, especially, I think one of the things that I love most about
1:21:01 all of these creative pursuits is that ability to work with the best people.
1:21:09 Right now, I’m working with my husband. We have this 1400-acre island in the Mediterranean,
1:21:14 and we’re bringing in the best architects and best brands. But to have a point of view
1:21:22 and to challenge people who are such artists, respectfully, but not to be afraid to ask
1:21:28 questions, it takes a lot of confidence to do that. And it’s hard. So these are actually just
1:21:33 internal early renderings. So we’re in the process of doing the master planning now.
1:21:39 But this is beautiful. It’s an early vision. Yeah. It’s going to be extraordinary.
1:21:45 Amman’s going to operate the hotel for us, and there are going to be villas, and we have
1:21:51 Carbone who’s going to be doing the food and beverage. But it’s amazing to bring together
1:21:56 all of this talent. And for me to be able to play around and flex the real estate muscles
1:22:00 again and have some fun with it is… The real estate, the design, the art. How hard is it to
1:22:05 bring something like that to life? Because that’s like, that looks surreal out of this world.
1:22:12 Well, especially on an island, it’s challenging, meaning the logistics of even getting the
1:22:20 building materials to an island or no joke, but we will execute on it. And it may not be this,
1:22:26 this is sort of, as I said, early conceptual drawings, but it gives a sense of sort of wanting to
1:22:33 honor the topography that exists. And this is obviously very modern, but making it feel right
1:22:41 in terms of the context of the vegetation and the terrain that exists is… And not just have
1:22:49 a beautiful glass box. Obviously, you want glass, you want to look out and see that gorgeous blue
1:22:56 ocean. But how do you do that in a way that doesn’t feel generic and isn’t a squandered
1:23:01 opportunity to create something new? Yeah. And it’s integrated with the natural landscape.
1:23:05 It’s the celebration of the natural landscape around it. So I guess you start from this dream-like,
1:23:09 because this feels like a dream. And then when you’re faced with the reality of the building
1:23:13 materials and all the actual constraints of the building, then it evolves from there, right?
1:23:20 Yeah. And so much, I mean, so much of architecture you don’t see, but it’s decisions made. So
1:23:26 how do you create independent structures where you look out of one and don’t see the other?
1:23:33 You know, how do you ensure the sort of the stacking and the master plan works in a way
1:23:40 that’s harmonious and view corridors and all of those elements, all of those components of
1:23:44 decision-making are super appreciated, but not often thought about.
1:23:46 What’s a view corridor?
1:23:52 Like to make sure that the top unit, you’re not looking out and seeing a whole bunch of units,
1:23:55 you’re looking out and seeing the ocean. So that’s where you take this and then you start
1:24:00 angling everything. And you start thinking about, well, in this context, do we have green roofs?
1:24:06 So if there’s any hint of a roof, it’s camouflage by vegetation that matches what already exists
1:24:11 on the island, where the engineers become very important. How do you build into a mountainside
1:24:16 while being sensitive to the beauty of the island?
1:24:21 It’s almost like a mathematical problem. I took a class, Computational Geometry in grad school,
1:24:26 where you have to think about these view corridors. It’s like a math problem.
1:24:31 But it’s also an art problem because it’s not just about making sure that there’s no occlusions
1:24:37 to the view. You have to figure out when there is occlusions, like what is the vegetation?
1:24:42 You have to figure all that out. And there’s probably, so every single room, every single
1:24:45 building is the thing that adds extra complexity.
1:24:50 And then the choice is like, how does the sun rise and set?
1:24:56 Yeah. So how do you want to angle the hotel in relation to the sun rise and the sunset?
1:25:05 Do you obviously want people to experience those? So which do you favor the directionality of the
1:25:12 wind on an island? And in this case, the wind is coming from the north and the vegetation is
1:25:18 less lush on the northern end. So do you focus more on the southern end and have the horseback
1:25:23 riding trails and amenities up towards the north? So there are these really interesting
1:25:28 decisions and choices you get to reflect on. That’s a fascinating sort of discussion to be
1:25:34 having. And probably there’s actual constraints on infrastructure issues. So all of those are
1:25:39 constraints. Well, the grade of the land, right? If it’s super steep. So also finding the areas
1:25:44 of topography that are flatter, but still have the great views. So it’s fun. I think for real
1:25:50 estate and building, it’s like a giant puzzle. And I love puzzles. Every piece relates to another
1:25:54 and it’s all sort of interconnected. Yeah. Like you said, in the whole post office,
1:25:58 like every single room is different. So every single room is a puzzle when you’re doing the
1:26:05 renovation. That’s fascinating. And if you’re not thoughtful, like it’s like, at best,
1:26:11 really quirky. At worst, completely ridiculous. Quirky is such a funny word.
1:26:17 You’ve walked into, I’m sure you’ve walked into your fair share of like quirky rooms.
1:26:24 And sometimes like that’s charming. But most often it’s charming when it’s intentional through
1:26:29 like smart design. Yeah, you can tell if it’s by accident or if it’s intentional. You can tell.
1:26:34 So much, I mean, the whole hospitality thing. So it’s not just like how it’s designed. It’s how,
1:26:39 once the thing is operating for the hotel, like how everything comes together.
1:26:43 Like the culture of the place. And the warmth. Yeah.
1:26:50 Like I think with spaces, you can feel like the soul of a structure. And I think
1:26:55 on the hotel side, you have to think about like flow of traffic. You saw these things,
1:27:00 when you’re building condominiums or your own home, you want to think about like the warmth
1:27:06 of a space as well. And especially with super modern design, sometimes like warmth is sacrificed.
1:27:13 And I think there is a way to sort of marry both. And that’s where you get into sort of the interior
1:27:21 design elements and disciplines and how fabrics can create tremendous warmth in a space, which is
1:27:27 otherwise sort of colder, raw building materials. And that’s a really interesting, like how texture
1:27:36 matters, how color matters. And I think oftentimes interior design is not,
1:27:45 it doesn’t take the same priority. And I think the, I think that underestimates the impact it can have
1:27:51 on how you experience a room or a space. Yeah. Especially when it’s working together with the
1:27:56 architecture. Yeah. Yeah. Fabrics and color. That’s so interesting.
1:28:01 Finishes, you know, the choice of wood. That’s making me feel horrible about the space we’re
1:28:07 sitting in. It’s like black curtains. The warmth. I need to work on this. No comment.
1:28:13 This is a big two-door. This is a big two-door item. You’re making me feel, I’ll listen back to this
1:28:19 over and over. There may be like a woman’s touch needed. A lot. A lot. But I actually, I appreciate
1:28:26 the vegetation. Yeah. Fake plants. You know what I love about this space though is it’s, is like you
1:28:32 come through. Like every single element, there’s a story behind it. So it’s not just some, you didn’t
1:28:37 have some interior designer curate your bookshelf. You know, there’s like, nobody came in here with
1:28:43 books by the yard. This is basically an Ikea, like this is not, this is not deeply thought through,
1:28:52 but it does bring me joy. Yeah. Which is one way to do design. As long as you’re happy, that usually
1:28:59 means if your taste is decent enough, that means others will be happy or we’ll see the joy radiate
1:29:03 through it. But I appreciate you were grasping for compliments and you eventually got that. No, I
1:29:09 actually, I love it. I love it. Do you have like a little, I love this guy. There’s, yeah, you’re
1:29:15 holding onto a monkey looking at a, at a human skull, which is particularly irrelevant.
1:29:22 This, I mean, I feel like you’ve really thought about all of these. Yeah. There’s robot. I don’t
1:29:27 know if, I mean, I don’t know how much you looked into robots, but there’s, there’s a way to communicate
1:29:32 love and affection from a robot that I’m really fascinated by. And a lot of cartoonists do this
1:29:38 too. You have to, when you create cartoons and non-human like entities, you have to bring out
1:29:47 the joy. So with Wally or robots and Star Wars, to be able to communicate emotion to anger and
1:29:52 excitement through a robot is really interesting to me. And people that do it successfully
1:30:00 are awesome. To make you smile. Yeah. That makes you smile for sure. There’s a longing there.
1:30:05 How do you do that successfully as you, as you bring them your projects to life?
1:30:10 I think there’s, there’s so many detailed elements that I think artists know well,
1:30:18 but one basic one is something that people know and you now know because you have a dog,
1:30:26 is the excitement that a dog has when it, when you first show up, just the recognizing you and
1:30:32 like catching your eye and just showing his excitement by wiggling his butt and tail and all
1:30:40 this kind of, this, this intense joy that overtakes his body, that, that moment of recognizing
1:30:47 something. It’s the double take that you’re, that, that moment of like where this joy of
1:30:54 recognition takes over your whole cognition and you’re just like there and there’s a connection.
1:30:58 And then the other person gets excited and you both get excited together. It’s kind of like that
1:31:03 feeling. What would I put it? You know, like when you go to airports and you get to see people
1:31:09 who haven’t seen each other for a long time, all of a sudden recognize each other in their meeting
1:31:14 and they’re all like, run towards each other in the hug and that moment. By the way, that’s
1:31:19 awesome to watch as somebody’s joy. And, and dogs though will have that every time you could walk
1:31:25 into the other room to get a glass of milk and you come back and your dog sees you like it’s the
1:31:31 first time. So I love replicating that in robots. They actually say children, like one of the reasons
1:31:38 why peek-a-boo is so successful is that they actually don’t remember not having seen you
1:31:44 a few seconds prior. There’s a, there’s a term for it, but I remember as when, when my kids were
1:31:49 younger, you leave the room and you walk back in 30 seconds later and they experienced the same joy
1:31:58 as if you had been, you know, gone for four hours. And we grew out of that. We become very used to
1:32:04 one another. I kind of want to forever be excited by the peek-a-boo phenomena. The simple joys we’re
1:32:09 talking about on fashion, having the confidence of taste to be able to sort of push through on
1:32:15 this idea of design. But you’ve also mentioned, and somebody you admire is Rick Rubin in his book,
1:32:23 The Creative Act. It has some really interesting ideas. And one of them is to accept self-doubt
1:32:29 and imperfection. So is there some battle within yourself that you have on sort of
1:32:37 striving for perfection and for the confidence and always kind of having it together versus like
1:32:42 accepting that things are always going to be imperfect? I think every day. I think I wake up
1:32:48 in the morning and, you know, I want to be better. I want to be a better mom. I want to be a better
1:32:58 wife. I want to be more creative. I want to be physically stronger. And so that very much lives
1:33:05 within me all the time. You know, I think I also grew up in the context of being the child of two
1:33:14 extraordinarily successful parents. And that could have been debilitating for me. And I saw that in
1:33:22 a lot of my friends who grew up in circumstances similar to that. They were afraid to try for fear
1:33:31 of not measuring up. And I think somehow early on, I learned to kind of harness the fear of not
1:33:40 being good enough, not being competent enough. And I harnessed it to make me better and to push me
1:33:47 outside of my comfort zone. So I think that’s always lived with me. And I think it probably
1:33:53 always will. I think you have to have humility in anything you do that you could be better
1:34:00 and strive for that. I think as you get older, it softens a little bit as you have more reps.
1:34:06 You know, as you have more examples of having been thrown in the deep end
1:34:15 and figured out how to swim, you get a little bit more comfortable in your sort of
1:34:23 abstract competency. But if that fear is not in you, I think you’re not challenging yourself
1:34:32 enough. Harnessed the fear. The other thing he writes about is intuition. That you need to trust
1:34:40 your instincts and intuition. That’s a very recruitment thing to say. So what percent of your
1:34:49 decision making is intuition or what percent is through rigorous, careful analysis? Would you
1:34:58 say? It’s both. It’s like trust would verify. I think that’s also where age and experience
1:35:04 comes into play because I think you always have sort of a gut instinct. But I think intuition,
1:35:12 like well-honed intuition, comes from a place of accumulated knowledge, right? So oftentimes,
1:35:17 when you feel really strongly about something, it’s because you’ve been there. You know what’s
1:35:25 right. Or on a personal level, if you’re acting in accordance with your core values,
1:35:31 you know, it just feels good. And even if it would be the right decision for others, if you’re
1:35:39 acting outside of your sort of integrity or core values, it doesn’t feel good. And your intuition
1:35:49 will signal that you’ll never be comfortable. So I think because of that, I start oftentimes with
1:35:57 my intuition. And then I put it through like a rigorous test of whether that is in fact true.
1:36:04 But very seldom do I go against what my initial instinct was, at least at this point in my life.
1:36:11 Yeah, I had actually a discussion yesterday with a big time business owner investor
1:36:18 who was talking about being impulsive and following that. Like on a phone call, shifting like the
1:36:24 entire everything, like giving away a very large amount of money and moving it in another direction
1:36:30 on an impulse, making a promise that he can’t at that time deliver but knows if he works hard,
1:36:36 he’ll deliver and all do just be following that impulsive feeling. And he said now that, you know,
1:36:42 he has a family that probably some of that impulse is quieted down a little bit. He’s more
1:36:49 rational and thoughtful and so on, but wonders whether it’s sometimes good to just be impulsive
1:36:55 and to just trust your gut and just go with it. Don’t deliberate too long because then you won’t
1:37:02 do it. It’s interesting. The confidence, the stupidity maybe of youth that leads to some
1:37:08 of the greatest breakthroughs and it’s like there’s a cost to wisdom and deliberation.
1:37:15 There is, but I actually think in this case, as you get older, you may act less impulsively,
1:37:22 but I think you’re more like attuned with. You have more experience, so your gut is like more
1:37:33 well-honed. So your instincts are more well-honed. I think I found that to be true for me. It doesn’t
1:37:42 feel as reckless as when I was younger. Amongst many other things, you were on the apprentice.
1:37:47 People love you on there. People love the show. So what did you learn about business,
1:37:53 about life from the various contestants on there? Well, I think you can learn everything about life
1:38:03 from Joe Burgers, so I’m just going to go with that. She was amazing. It was such a
1:38:09 wild experience for me because I was quite young when I was on it, just getting started in business
1:38:15 and it was the number one television show in the country and it went on to be syndicated all over
1:38:24 the world and it was just this wild, phenomenal success. A business show had never crossed over
1:38:31 in this way. So it was really a moment in time and you had regular apprentice and then the celebrity
1:38:36 apprentice, but the tasks, I mean, they went on to be studied at business schools across the
1:38:42 country. So every other week, I’d be reading case studies of how the apprentice was being examined
1:38:48 and taught to classes and this university in Boston. So it was extraordinary and this was
1:38:54 like a real life classroom I was in. So I think because of the nature of the show, you learn a
1:39:00 lot about teamwork and you’re watching it and analyzing it real time. You learned a lot about,
1:39:07 a lot of the tasks were very marketing oriented because of the short duration of time they had
1:39:15 to execute. A lot of, you learned a lot about time management because of that short duration.
1:39:22 So almost every episode would devolve into people hysterical over the fact that they had 10 minutes
1:39:30 left with this Hercules and Lyft ahead of them. So it was a fascinating, it was a fascinating
1:39:35 experience for me and we would be filming, I mean, we would film first thing in the morning
1:39:42 at like 5 or 6 a.m. in Trump Tower oftentimes, like in the lobby of Trump Tower. That’s where
1:39:48 the war rooms and board rooms of the candidates were, the contestants were.
1:39:54 And then we would go up in the elevator to our office. We would work all day and then we’d come
1:40:01 down and we’d evaluate the tasks. It was this weird, like real life television thing experience
1:40:08 in the middle of our, sort of on the bookends of our workday. So it was intense.
1:40:12 So you’re curating the television version of it and also living it?
1:40:18 Well, living the, and oftentimes there was like an overlay. Like there were episodes that they
1:40:26 came up with brand campaigns for my shoe collection or my clothing line or design
1:40:31 challenges related to a hotel that was responsible for buildings. So there was this
1:40:37 unbelievable crossover that was obviously great for us from a business perspective,
1:40:44 but it’s sometimes surreal to experience. What was it like? Was it scary to be in front of a
1:40:50 camera when you know so many people watch? I mean, that’s a new experience for you at that time,
1:41:00 just the number of people watching. Yeah. Was that weird? It was really weird. I really struggled
1:41:09 watching myself on the episodes. Like I really, I still to this day, like television as a medium,
1:41:13 like the fact that we’re taping this. Yeah. I’m more self-conscious than if we weren’t. I just,
1:41:22 it’s. Hey, I have to watch myself. After we record this, before I publish it,
1:41:29 I have to listen to my stupid self-talk. So you’re saying it doesn’t get better?
1:41:34 It doesn’t get better. I still, I hear myself. I’m like, does my voice really sound like that?
1:41:42 You know, why do I do this thing or that thing? And I find it, some people are super at ease and
1:41:46 who knows? Maybe they’re not either. But some people feel like they’re super at ease.
1:41:55 My father was, I think, like who you saw as who you get. And I think that made him so effective
1:42:01 in that medium because he was just himself and he was totally unselfconscious. I was not.
1:42:11 I was totally self-conscious. So it was extraordinary, but also a little challenging for me.
1:42:16 I think certain people are just like born to be entertainers, like Elvis, like on stage,
1:42:21 they come to life. Yeah. This is where they, this is where they’re truly happy. I’ve met,
1:42:27 I’ve met guys like that, like great rock stars. Like this is where they feel like they belong.
1:42:31 On stages, it’s not just the thing they do and they, there’s certain aspects they love,
1:42:35 certain aspects they don’t know. This is where, this is where they’re alive. This is where they,
1:42:39 they’ve always dreamed of being. This is where they want to be forever.
1:42:42 Michael Jackson was like that. Michael Jackson, some pictures of you hanging out
1:42:47 with Michael Jackson. That was cool. He came once to a performance. I wanted to be,
1:42:56 one moment in time, I wanted to do a professional ballerina. And I was working really hard. I was
1:43:00 going to the School of American Ballet. I was dancing at the Lincoln Center in the nutcracker.
1:43:08 I was super serious, nine, 10 year old. And my parents came to a Christmas performance of
1:43:14 the nutcracker and my father brought Michael Jackson with him. And everyone was so excited
1:43:22 that all the dancers, they wore one glove. But I remember he was so shy. He was so quiet.
1:43:31 When you’d see him, like in smaller group settings, and then you’d watch him walk onto stage.
1:43:39 And it was like a completely different person. Like the vitality that came into him. And you
1:43:45 say that’s like someone who was born to do what he did. And I think there are a lot of performers
1:43:53 like that. And I just in general love to see people that have found the thing that makes
1:43:59 them come alive. Yeah. Like I, as I mentioned, went to the jungle recently with Paul Rosely.
1:44:04 And he’s a guy who just belongs in the jungle. Yeah. Like that’s a guy where like when I,
1:44:11 I got a chance to go with him from the city to the jungle. And you just see this person change
1:44:19 of the happiness, the joy he has when he first is able to jump in the water at the Amazon River
1:44:26 and to feel like he’s home with the crocodiles and all that. And with what he’s calling friends and
1:44:31 probably dances around in the trees with the monkeys. So he, like he, this is, this is where
1:44:37 he belongs. And I love seeing that. You felt that. I mean, I watched the interview you did with him and
1:44:46 and you felt that like his passion and enthusiasm, like it radiated and captivated. I mean, I’m,
1:44:52 I love animals. Like I love all animals. Never loved snakes so much. And he almost made me,
1:44:58 now I appreciate the beauty of them much more than I did prior to listening to him speak about them.
1:45:03 But it’s an infectious thing. He actually, we were talking about skyscrapers before. I loved,
1:45:09 he called trees skyscrapers of life. And I thought that was so great. Yeah. And they are,
1:45:18 they’re so big. I mean, just like skyscrapers or large buildings, they also represent a history,
1:45:22 especially in Europe. I like to think, look at all these ancient buildings,
1:45:26 you like to think of all the people throughout history that have looked at them,
1:45:32 have admired them, have been inspired by them. You know, great leaders of history.
1:45:36 In France, it’s like Napoleon, just the history that’s contained within a building,
1:45:42 you almost feel the energy of that history. You could feel the stories emanate from the buildings.
1:45:49 And that same way, when you look at giant trees that have been there for decades, for centuries,
1:45:56 in some cases, you, you feel the history, the stories emanate. I got just to climb some of them.
1:46:01 So you feel like there’s a visceral feeling of the power of the trees. It’s cool. Yeah.
1:46:08 That’s an experience I’d love to have be that disconnected. Yeah. Being in the jungle,
1:46:14 among the trees, among the animals, you remember that you’re forever a part of nature. You’re,
1:46:21 you’re fundamentally our nature, that this isn’t a, earth is a living organism and you’re a part of
1:46:28 that organism. And that’s humbling, that’s beautiful. And you get to experience that in a real, real way.
1:46:32 It sounds simple to say, but when you actually like experience it, it stays with you for a long
1:46:38 time, especially if you’re out there alone. I got a chance to spend time in the jungle solo,
1:46:48 just by myself. And you sit in the fear of that, in the simplicity of that, all of it, and just
1:46:56 no sounds of humans anywhere. You’re just sitting there and listening to all the monkeys and the
1:47:02 birds trying to have sex with each other, all around you, just screaming. And there’s like
1:47:06 romantic, I mean, I romanticize everything. There’s like birds that are monogamous for life,
1:47:11 like macaws. You could see like two of them flying. They’re also, by the way, screaming at each
1:47:16 other. I always wonder like, are they arguing or is this their love language? Like, you just
1:47:21 have these like two birds that you know have been together for a long time and they’re just screaming
1:47:25 at each other in the morning. That’s really funny because there aren’t that many animal species that
1:47:30 are monogamous and you highlighted one example where they literally sound like they’re bickering.
1:47:35 But maybe to them it’s beautiful. You know, I don’t want to judge, but they do sound very loud
1:47:41 and very obnoxious. But amidst all of that, it’s just, I don’t know.
1:47:48 I think it’s so humbling to like feel so small too. Like, I feel like when we get busy and when
1:47:55 we’re running around, it’s easy to feel, we’re so in our head and we feel sort of so consequential,
1:48:00 like in the context of even our own lives. And then you find yourself in a situation like that.
1:48:07 And it’s, I think you feel so much more connected knowing how minuscule you are
1:48:12 in the broader sense. And I feel that way when I’m on the ocean, on a surfboard.
1:48:21 You know, you just, it’s really humbling to be so small amidst that vast sea. And it feels,
1:48:29 it feels really beautiful, you know, with no noise, no chatter, no distractions.
1:48:35 Just being in the moment. And it sounds like you experienced that in a
1:48:41 very, very real way in the Amazon. Yeah, the power of the waves is cool. I love swimming out into the
1:48:45 ocean and feeling the power of the ocean beneath you. You’re just like this speck.
1:48:50 And you can’t fight it, right? You just have to sort of be in it. And I think in surfing,
1:48:54 one of the things I love about it is I feel like a lot of water sports are like manipulating
1:49:00 the environment, you know? And there’s something that can be a little like violent about it,
1:49:06 like you look at windsurfing and whereas with surfing, you’re like in harmony with it. So
1:49:13 you’re not fighting it. You’re, you’re flowing with it. And you still have like the agency of
1:49:18 choosing which waves you’re going to surf. And you sit there and you, you read the ocean and,
1:49:26 and you learned to understand it, but you can’t control it. What’s it like to like,
1:49:33 like fall in your face when you’re trying to surf? Like what, I haven’t surfed before. It just feels
1:49:39 like, I always see videos of when everything goes great. I just wonder like when it doesn’t.
1:49:44 Those are the ones people post. No, well, I actually had the unique experience of
1:49:48 one of my first times surfing. I only learned a couple of years ago. So I’m not good.
1:49:53 I just love it. I love everything about it. I love the physicality. I love being in the ocean.
1:49:59 I love everything about it. The hardest thing with surfing is paddling out because when you’re
1:50:03 like committing, you catch a wave, obviously sometimes like, you know, you flip over your board
1:50:09 and that doesn’t feel great. But when you’re in sort of the line of impact and you’ve maybe surfed
1:50:14 a good wave in and now you’re going out for another set and you get sort of stuck in that impact line,
1:50:19 there’s like nothing you can do. You just sort of sit there and you try to dive underneath it
1:50:25 and it will pound you and pound you. So I’ve been stuck there while, you know, four, five,
1:50:32 six waves just like crash on top of your head. And the worst thing you can do is get reactive and,
1:50:38 you know, and scared and try and fight against it. You kind of just have to flow with it until
1:50:44 inevitably there’s a break and then paddle like hell back out to the line or to the beach.
1:50:48 Whatever, you know, whatever you’re feeling. But it’s that’s, to me, that’s the hardest part,
1:50:55 the paddling out. How did life change when your father decided to run for president?
1:51:06 Wow, everything changed, you know, almost overnight. We learned that he was planning to
1:51:15 announce his candidacy two weeks before he actually did. And nothing about our lives
1:51:22 had been constructed with politics in mind, you know, most often when people are exposed to
1:51:30 politics at that level, that sort of national level, there’s first like city council run
1:51:37 and then maybe a state level run and and maybe maybe, you know, congress senator,
1:51:46 ultimately the presidency. So it was unheard of for him never to run a campaign and then run for
1:51:56 president and win. So it was it was an extraordinary experience. There was so much intensity and so
1:52:05 much scrutiny and and so much noise. So that took for sure, like a moment to acclimate to,
1:52:14 I’m not sure I ever fully acclimated, but it definitely was was a super unusual experience.
1:52:23 But I think then the the process that unfolded over over the next couple of years was also
1:52:29 like the most extraordinary growth experience of my life. You know, suddenly I was going into
1:52:36 communities that I probably never would have been to. And I was talking with people who in 30
1:52:45 seconds would reveal to me their deepest insecurity, their gravest fear, their wildest ambitions,
1:52:50 all of it with the hope that in telling me that story, it would get back to
1:52:56 a potential future president of the United States and have impacts for their family, for their
1:53:04 community. So the level of candor and vulnerability people have with you is on like anything I’ve
1:53:11 ever experienced. And I’ve done the apprentice before people may know who I was in some of these
1:53:17 situations that I was going into. But they wouldn’t have shared with me these things that you got the
1:53:21 impression that oftentimes their own spouses wouldn’t know. And they wouldn’t do so within 30
1:53:31 seconds. So you learn so much about what motivates people, what drives people, what their concerns
1:53:39 are, and you grow so much as a result of it. So when you’re in the White House, people,
1:53:45 unlike in any other position, people have a sense that all the troubles they’re going through,
1:53:54 maybe you can help. So they put it all out there. And they do so in such a raw, vulnerable,
1:54:05 and real way. It’s shocking and eye-opening and super motivating. I remember once I was
1:54:11 in New Hampshire and early on, right after my father had announced his candidacy,
1:54:20 and a man walks up to me in the greeting line. And within around five seconds, he had started to
1:54:27 tell me a story about how his daughter had died of an overdose and how he was worried his son was
1:54:36 also addicted to opioids, his daughter’s friends, his son’s friends, and it’s heartbreaking. It’s
1:54:42 heartbreaking and it’s something that I would experience every day in talking with people.
1:54:51 And those stories just stay with you? Always. You know, I took a long road trip around the
1:54:57 United States in my 20s. And I’m kind of thinking of doing it again just for like a couple of months
1:55:04 for that exact purpose. And you can get these stories when you go to like a bar in the middle
1:55:11 of nowhere, and just sit and talk to people. And they start sharing. And it reminds you like how
1:55:17 beautiful the country is. It reminds you several things. One, that people, well, it shows you
1:55:22 that there’s a lot of different accents. That’s for one. But aside from that, that people are
1:55:28 struggling with all the same stuff. And at least at that time, I wonder what it is now. But at that
1:55:35 time, I don’t remember on the surface, there’s like political divisions, there’s Republicans and
1:55:41 Democrats and so on. But like underneath it, there are people who are all the same. The concerns
1:55:46 are all the same. There’s not that much of a division. Right now, the surface division has
1:55:52 been amplified even more maybe because of social media. I don’t know why. So I would love to see
1:55:59 what the country is like now. But I suspect probably it’s still not as divided as it appears to be
1:56:05 on the surface with the media shows, with the social media shows. But what did you experience
1:56:11 in terms of the division? I think a couple of reactions to what you just said. I think the
1:56:22 first is when you connect with people like that, you are so inspired by their courage in the face
1:56:30 of adversity and their resilience. And it’s a truly remarkable experience for me. The campaign
1:56:36 lifted me out of a bubble I didn’t even know I was in. I grew up on the Upper East Side of New
1:56:43 York and I felt like I was well-traveled and well-educated. And I believed at the time that I’d
1:56:52 been exposed to divergent viewpoints. And I realized during the campaign how limited my exposure
1:56:58 had been relative to what it was becoming. So there was a lot of growth in that as well.
1:57:05 But I do think you think about the vitriol and politics and whether it’s worse than it’s been
1:57:09 in the past or not, I think that’s up for debate. I think there have been
1:57:17 there have been duels and there’s been screaming. And politics has always been
1:57:23 a bloodsport and it’s always been incredibly vicious. I think in the toxic swirl of social
1:57:31 media, it’s more amplified. And there’s more democratization around participating in it,
1:57:38 perhaps. And it seems like the voices are louder, but it’s always been, it feels like it’s always
1:57:48 been that. But I don’t believe most people are like that. And you meet people along the way
1:57:54 and they’re not leading with what their politics are. They’re telling you about their hopes for
1:58:02 themselves and their communities. And it makes you feel that we are a whole lot less divided
1:58:10 than the media and others would have us believe. Although I have to say, having duels sounds pretty
1:58:16 cool. Maybe I just romanticize westerns. Anyway, all right, I miss Clint Eastwood movies. Okay.
1:58:21 But it’s true, like you read some of the stuff like in terms of what politics used to be in
1:58:27 the history of the United States, those folks went pretty rough, like way rougher actually,
1:58:32 but they didn’t have social media. So they had to go like real hard. And the media was rough too.
1:58:40 So all the fake news, all of that, that’s not recent. It’s been nonstop. I look at the surface
1:58:45 division, the surface bickering. And that might be just a feature of democracy. It’s not a bug
1:58:52 of democracy. It’s a feature. We’re in a constant conflict. And it’s the way we resolve, we try
1:58:57 to figure out the right way forward. So in the moment, it feels like people are just tearing
1:59:02 each other apart, but really, we’re trying to find the way where like in the long arc of history,
1:59:08 it will look like progress. But in the short term, it just sounds like people making stories up about
1:59:15 each other and calling each other names and all this kind of stuff. But there’s a purpose to it.
1:59:19 I mean, that’s what freedom looks like, I guess is what I’m trying to say, and it’s better than
1:59:24 the alternative. I think that the vast majority of people aren’t participating in it. Sure. Yes,
1:59:29 that’s true also. You know, I think there’s a minority of people that are doing most of the
1:59:34 yelling and screaming. And the majority of Americans just want to send their kid to a great
1:59:43 school and want their communities to thrive and want to be able to realize their dreams and
1:59:51 aspirations. So I saw a lot more of that than it would feel obvious if you looked at like
1:59:59 a Twitter feed. What went into your decision to join the White House as an advisor?
2:00:09 You know, the campaign, I never thought about joining. I was kind of like get to the end of it.
2:00:15 And when it started, everything in my life was almost firing on all cylinders. I had two young
2:00:21 kids at home. During the course of the campaign, I ended up, I was pregnant with my third. So
2:00:30 this young family, my businesses, real estate and fashion, and working alongside my brothers,
2:00:39 running the Trump Hotel collection. My life was full and busy. And so there was a big part of me
2:00:45 that was just wanted to get through, just get through it without really thinking forward to
2:00:53 what the implications were for me. But when my father won, he asked Jared and I to join him.
2:01:00 And in asking that question, you know, keep in mind, he was a total outsider. So there was no
2:01:06 bench of people as he would have today. He had never spent the night in Washington, D.C. before
2:01:12 staying in the White House. And so when he asked us to join him, he trusted us, he
2:01:20 trusted in our ability to execute. And there wasn’t a part of me that could imagine
2:01:28 the 70 or 80 year old version of myself looking back and having been okay with having said no,
2:01:35 and going back to my life as I knew it before. I mean, in retrospect, I realized there is no life
2:01:44 as you know it before, you know, but just the idea of not saying yes, wherever that would
2:01:55 lead me. And so I dove in. I was also, during the course of the campaign, I was just much more
2:02:03 sensitive to the problems and experiences of Americans. I gave you an example before of the
2:02:10 father in New Hampshire, but even just in my consumption of information, you know, I had a
2:02:16 business that was predominantly young women, you know, many of which were thinking about having a
2:02:24 kid, had just had a child, were planning on that life event. And I knew what they needed to be able
2:02:29 to show up every day and realize the stream for themselves and the support structures they would
2:02:36 need to have in place. And I remember reading this article at the time in one of the major
2:02:45 newspapers of a woman, she had had a very solid job working at one of the blue chip
2:02:51 accounting firms. And the recession came, she lost her job around the same time as her partner
2:02:59 left her. And over a matter of months, she lost her home. So she wound up with her two young
2:03:11 kids after bouncing around between neighbors living in their car. She gets a call back from
2:03:16 one of the many interviews she had done for a second interview where she was all but guaranteed
2:03:22 the job should that go well. And she had arranged childcare for her two young children with a
2:03:28 neighbor in her old apartment block. And the morning of the interview, she shows up and the
2:03:35 neighbor doesn’t answer the doorbell and stands there five, 10 minutes, doesn’t answer. So she
2:03:43 has a choice. Does she go to the interview with her children or does she try to cancel? She gets
2:03:47 in her car, drives to the interview, leaves her two children in the backseat of the car
2:03:53 with the window cracked, goes into the interview and gets pulled out of the interview by police
2:03:57 because somebody had called the cops after seeing her, her children in the backseat of the car.
2:04:05 She gets thrown in jail. Her kids get taken from her. And she spends years fighting to regain
2:04:10 custody. And I think about, that’s an extreme example, but I think about something like that.
2:04:15 And I say, if I was the mother and we were homeless, would I have gone to that interview?
2:04:29 And I probably would have. And that is not an acceptable situation. So you hear stories like
2:04:37 that and then you get asked, will you come with me? And it’s really hard to say no. I spent four
2:04:43 years in Washington. I feel like I left it all in the field. I feel really good about it. And
2:04:49 I feel really privileged to have been able to do what I did.
2:04:58 A chance to help many people. Saying no means you’re kind of turning away from those people.
2:05:00 Felt like that to me.
2:05:07 Yeah. Yeah, but then it’s the turmoil of politics that you’re getting into. And
2:05:17 it really is a leap into the abyss. What was it like trying to get stuff done in Washington?
2:05:27 And this place where politics is a game, it feels that way, maybe from an outsider perspective.
2:05:31 And you go in there trying, given some of those stories trying to help people,
2:05:35 what’s the like to get anything done? It’s an incredible cognitive lift.
2:05:43 That’s a nice way to put it, yeah. To get things done. There are a lot of people who
2:05:53 would prefer to cling to the problem. And they’re talking points about how they’re going
2:05:59 to solve it rather than roll up their sleeves and do the work it takes to build coalitions of
2:06:06 support and find people who are willing to compromise and move the ball. And so it’s extremely
2:06:11 difficult. And Jared and I talk about all the time, it probably should be. Because these are
2:06:17 highly consequential policies that impact people’s lives at scale. It shouldn’t be so easy to do
2:06:24 them and they are doable. But it’s challenging. One of the first experiences I had where it
2:06:31 really was just a full-grind effort was with tax cuts and the work I did to
2:06:38 get the child tax credit doubled as part of it. And it just meant meeting after meeting after
2:06:44 meeting after meeting with lawmaker, convincing them of why this is good policy, going into their
2:06:50 districts, campaigning in their districts, helping them convince their constituents of why it’s
2:06:58 important, of why child care support is important, of why paid family leave is important, of different
2:07:09 policies that impact working American families. So it’s hard, but it’s really rewarding. And then
2:07:14 to get it done, I mean, just the child tax credit alone, 40 million American families
2:07:22 got an average of $2,200 each year as a result of the doubling of the child tax credit set,
2:07:28 one component of tax cuts. When I was researching this stuff, you just get to think
2:07:36 the scale of things, the scale of impact, is 40 million families. Each one of those is the story,
2:07:42 is the story of struggle, of trying to give a large part of your life to a job,
2:07:46 while still being able to give love and support and care to a family and to kids,
2:07:50 and to manage all of that. Each one of those is a little puzzle that they have to solve,
2:07:57 and it’s a life and death puzzle. It’s a, you can lose your home, your security, you can lose
2:08:04 your job, you can screw stuff up with parenting. So you can mess all that up and you’re trying to
2:08:13 hold it together, and government policies can help make that easier, or can in some cases make that
2:08:19 possible. And you get to do that at a scale not of like five or 10 families, but like 40 million
2:08:24 families. And that’s just one thing. Yeah. The people who shared with me their experience, and
2:08:31 you know, during the campaign, it was what they hoped to see happen. Once you were in there,
2:08:36 it was what they were seeing, what they were experiencing, the result of the policies. And
2:08:44 that was the fuel. You know, on the hardest days, like that was the fuel. Child tax credit.
2:08:49 I remember visiting with a woman, Brittany, a houseman. She came to the White House. She had
2:08:53 two small children. She was pregnant with her third. Her husband was killed in a car accident.
2:08:59 She was in school at the time. Her dream was to become a criminal justice advocate.
2:09:04 That was no longer on the table for her after he passed away. And she became
2:09:10 the sole learner and provider for her family. And she couldn’t afford childcare. She couldn’t
2:09:18 afford to stay in school. So she ended up creating a childcare center in her home. And her center
2:09:24 was so successful because in part of different policies we worked on, including the childcare
2:09:29 block grants that went to the state, she ended up opening additional centers. I visited her at one
2:09:38 of them in Colorado. Now, she has a huge focus on helping teenage moms who don’t have the resources
2:09:45 to afford quality childcare for their kids come into her centers and programs. And it’s stories
2:09:51 like that of the hardships people face, but also what they do with opportunity when they’re given it
2:09:58 that really powers you through tough moments when you’re in Washington.
2:10:04 What can you say about the process of bringing that to life? So the child tax credits,
2:10:12 so doubling them from 1,000 to 2,000 per child. What are the challenges of that,
2:10:16 getting people to compromise? I’m sure there’s a lot of politicians playing games with that
2:10:20 because maybe it’s the Republican that came up with an idea or a Democrat that came up with an
2:10:25 idea and so they don’t want to give credit to the idea. And there’s probably all kinds of games
2:10:32 happening where they, when the game is happening, you probably forget about the families. Each
2:10:37 politician thinks about how they can benefit themselves if you get like the serving part
2:10:41 of the role you’re supposed to be in. There were definitely people I met with in Washington
2:10:48 who I felt that was true of, but they all go back to their districts. And I assume that they all
2:10:53 have similar experiences to what I had where people share their stories. So there’d be something
2:10:58 really cynical about thinking they forget, but some do. You help get people together.
2:11:02 What’s that take, trying to get people to compromise, trying to get people to see the
2:11:06 common humanity? Well, I think first and foremost, you have to be willing to talk with them.
2:11:14 So one of the policies I advocated for was paid family leave. We left and 9 million more Americans
2:11:20 had it through a combination of securing it for our federal workforce. I had people in the White
2:11:27 House who were pregnant who didn’t have access to paid leave. So we want to keep people attached to
2:11:34 the workforce. Yet when they have an important life event like a child, we create an impossibility
2:11:40 for that. Some people don’t even have access to one paid leave if they’re part-time workers.
2:11:48 So that and then we also put in place the first ever national tax credit for workers
2:11:55 making under $72,000 a year where employers could then offer it to their workers. That was also part
2:12:02 of tax cuts. So part of it is really taking the arguments as to why this is good, smart,
2:12:11 well-designed policy to people. And it was one of my big surprises that on certain policy issues
2:12:17 that I thought would have been well-socialized, the policies that existed were never shared
2:12:24 across the aisle. So people just lived with them maybe in hopes that one day they would have
2:12:30 the votes to get exactly what they want. But I was surprised by how little discussion there was.
2:12:36 So I think part of it is be willing to have those tough discussions with people who may not share
2:12:44 your viewpoint and be an active listener when they point out flaws and they have suggestions for
2:12:53 changes, not believing that you have a monopoly on good ideas. And I think there has to be a lot of
2:13:01 humility in architecting these things. And a policy should benefit from that type of well-rounded
2:13:06 input. Yeah, be able to see, like you said, well-designed policies. There’s probably like the
2:13:13 details are important too. There’s just like with architecture and you walk the rooms. There’s
2:13:20 probably really good designs of policies, economic policy that helps families, that delivers the
2:13:27 maximum amount of money or resources to families they needed and is not a waste of money. So like
2:13:33 that, there’s probably really nice designs there and nice ideas that are bipartisan that has nothing
2:13:39 to do with politics has to do with just great economic policy. It’s great policies. And that
2:13:46 requires listening. Quarters trust too. Like I learned tax cuts was really interesting for me
2:13:53 because I met with so many people across the political spectrum on advancing that policy. I
2:13:59 really figured out who was willing to deviate from their talking points when the door was closed
2:14:08 and who wasn’t. And it takes some courage to do that, especially without surety that it would
2:14:14 actually get done, especially if they’ve campaigned on something that was slightly different.
2:14:20 And not everyone has that courage. So through tax cuts, I learned the people who did have that
2:14:26 courage. And I went back to that well time and time again on policies that I thought were important.
2:14:34 Some were bipartisan. The Great American Outdoors Act is something, it’s incredible policy.
2:14:36 I love that one.
2:14:41 Yeah, it’s amazing. It’s one of the largest pieces of conservation legislation since
2:14:50 the national park system was created. And over 300 million people visit our national parks
2:14:54 the vast majority of them being Americans every year. So this is something that is real and
2:14:59 beneficial for people’s lives, getting rid of the deferred maintenance, permanently funding them.
2:15:06 But there are other issues like that that just weren’t being prioritized, modernizing Perkins
2:15:11 CTE in vocational education. And it’s something I became super passionate about
2:15:20 and help lead the charge on. I think in America for a really long period of time,
2:15:25 we’ve really believed that education stops when you leave high school or college.
2:15:31 And that is not true. And that’s a dangerous way to think. So how can we both galvanize the
2:15:36 private sector to ensure that they continue to train workers for the jobs they know are coming?
2:15:44 And how they train their existing workforce into the new jobs with robotics or machinery or new
2:15:51 technologies that are coming down the pike. So galvanizing the private sector to join us in that
2:15:57 effort. So whether it’s the legislative side, like the actual legislation of Perkins CTE,
2:16:03 which was focused on vocational education, or whether it’s the ability to use the White House to
2:16:10 galvanize the private sector, we got over 16 million commitments from the private sector to
2:16:17 retrain or reskill workers into the jobs of tomorrow. Yeah, there’s so many aspects of
2:16:23 education that you’re helped on. Access to STEM and computer science education. So the CTE thing
2:16:27 you’re mentioning, modernizing career and technical education, that’s millions, millions of people.
2:16:34 The act provided nearly $1.3 billion annually to more than 13 million students to better align
2:16:41 the employer needs and all that kind of stuff. Very large scale policies that help a lot of
2:16:46 people. It’s fascinating. Education often isn’t like the bright shiny object everyone’s running
2:16:53 towards. So one of the hard things in politics when there’s something that is good policy,
2:16:58 sometimes it has no momentum because it doesn’t have a cheerleader. So where are areas of good
2:17:08 policy that you can literally just carry across the finish line? Because people tend to run towards
2:17:14 what’s the news of the day, to try to address whatever issues being talked about on the front
2:17:20 pages of papers. And there’s so many issues that need to be addressed. And education is one of them
2:17:27 that’s just under prioritized human trafficking. That’s an issue that I didn’t go to the White
2:17:34 House thinking I would work on, but you hear a story of a survivor and you can’t not want to
2:17:42 eradicate one of the greatest evils that the mind can even imagine. The trafficking of people,
2:17:48 the exploitation of children. And I think for so many, they assume that this is a problem that
2:17:55 doesn’t happen on our shores. It’s something that you may experience at far flung destinations
2:18:01 across the world, but it’s happening there and it’s happening here as well. And so through a
2:18:09 coalition of people that, on both sides of the aisle, that I came to trust and to work well with,
2:18:16 we were able to get legislation, which the president signed, past nine pieces of legislation,
2:18:22 combating, trafficking at home and abroad, and digital exploitation of children.
2:18:28 How much of a toll does that take, seeing all the problems in the world at such a large scale,
2:18:34 the immensity of it all? Was that hard to walk around with that, just knowing how much suffering
2:18:39 there is in the world? As you’re trying to help all of it, as you’re trying to design government
2:18:46 policies to help all of that, it’s also a very visceral recognition that there is suffering in
2:18:54 the world. How difficult is that to walk around with? You feel it intensely. We were just talking
2:19:00 about human trafficking. I mean, you don’t design these policies in the absence of the input of
2:19:07 survivors themselves, so you hear their stories. Remember a woman who was really influential
2:19:15 in my thinking, Andrea Hipwell, who she was in college where she was lured out by a guy she
2:19:22 thought was a good guy, started dating him. He gets her hooked on drugs, convinces her to drop
2:19:27 out of college and spends the next five years selling her. She only got out when she was arrested.
2:19:32 All too often, that’s happening too, that the victim’s being targeted,
2:19:43 not the perpetrator. We did a lot with DOJ around changing that, but now she’s helping
2:19:51 other survivors get skills and job training and the therapeutic interventions they need.
2:19:57 But you speak with people like Andrea and so many others. I mean, you can’t not, your
2:20:06 heart gets seized by it. It’s both motivating and it’s hard. It’s really hard.
2:20:12 I was just talking to a brain surgeon. Many of the surgery has to do, he knows the chances
2:20:23 are very low of success. He says that that wears at his armor. It chips away. It’s only so many
2:20:27 times can you do that. And thank God he’s doing it because I bet you there are a lot of others that
2:20:32 don’t choose that particular field because of those low success rates. But you can see the pain
2:20:39 in his eyes. Maintaining your humanity while doing all of it. You could see the story though.
2:20:47 You could see the family that loves that person. You feel the immensity of that and you feel the
2:20:53 heartbreak involved with mortality in that case and with suffering also in that case and in general
2:21:01 in all these in human trafficking. But even in helping families try to stay afloat, trying to
2:21:06 break out or escape poverty, all that. You get to see those stories of struggle. It’s not easy.
2:21:15 But the people that really feel the humanity of that, feel the pain of that are probably the
2:21:20 right people to be politicians. But it’s probably also why you can’t stay in there too long.
2:21:28 It’s the only time in my life where you actually feel like there’s always a conflict, right,
2:21:36 between work and life and making sure as a woman I’d often get asked about, how do you balance
2:21:43 work and family? And I never liked that question because balance, it’s elusive.
2:21:53 You’re one fever away from no balance. You’re child sick one day. What do you do?
2:22:00 There goes balance or you have a huge project with a deadline, there goes balance. I think
2:22:04 a better way to frame it is, am I living in accordance with my priorities?
2:22:11 Maybe not every day, but every week and every month and reflecting on have you
2:22:18 architected a life that aligns with your priorities so that more often than not you’re
2:22:26 where you need to be in that moment. And service at that level was the one time where you really,
2:22:33 you feel incredibly conflicted about having any priorities other than serving. It’s finite.
2:22:39 In every business I’ve built, you’re building for duration. And then you go into the White House
2:22:44 and it is sand through an hourglass, whether it’s four years or eight years. It’s a finite
2:22:49 period of time. And most people don’t last four years. I think the average in the White House
2:22:57 is 18 months. It’s exhausting. But it’s the only time when you’re at home with your own children
2:23:04 that you think about all the people you’ve met and you feel guilty about any time that’s spent
2:23:13 not advancing those interests to the best of your capacity. And that’s a hard thing.
2:23:19 That’s a really hard feeling as a parent. And it’s really challenging then to be present,
2:23:27 to always need to answer your phone, to always need to be available. It’s very difficult. It’s
2:23:34 taxing. But it’s also the greatest privilege in the world. So through that, the turmoil,
2:23:38 that the hardship of that, what was the role of family through all that? Jared and the kids,
2:23:45 what was that like? That was everything. To have that, to have the support systems
2:23:52 I had in place with my husband. We had left New York and wound up in Washington. In New York,
2:23:57 I lived 10 blocks away from my mother-in-law, who if I wasn’t taking my kids to school,
2:24:02 she was. So we lost some of that, which was very hard. But we had what mattered, which was each
2:24:10 other. And you know, my kids were young. When I got to Washington, Theo, my youngest was eight
2:24:22 months old. And Arabella, my oldest, my daughter was five years old. So they were still quite young.
2:24:32 We have a son, Joseph, who was three. And I think for me, the dose of levity coming home at night
2:24:44 and having them there and just joyful. It was super grounding and important for me. I still
2:24:50 remember Theo. When he was around three, three and a half years old, Jared used to make me coffee
2:24:56 every morning. And it was like my great luxury that I would sit there. He still makes it for
2:24:59 me every morning. I told him, I’m never, even though I secretly know how to actually work the
2:25:04 coffee machine, but I’ve convinced him that I have no idea how to work the coffee machine.
2:25:09 Now I’m going to be busted. But it’s a skill I don’t want to learn because it’s one of
2:25:14 his acts of love. He brings me coffee every morning in bed while I read the newspapers.
2:25:23 And Theo would watch this. And so he got Jared to teach him how to make coffee. And Theo learned
2:25:30 how to make a full blown cappuccino. And he was so, he had so much joy in every morning bringing me
2:25:40 this cappuccino. And I remember the sound of his little steps, the slide. It was so cute coming
2:25:45 down the hallway with my perfectly foamed cappuccino. Now I try to get him to make me coffee.
2:25:51 And he’s like, come on, mom. So it was a moment in time, but we had a lot of little
2:26:00 moments like that that were just amazing. Yeah, I got a chance to chat with him. And he has his
2:26:06 silliness and sense of humor. It’s, yeah, it’s really joyful. I could see how that could be an
2:26:14 escape from the madness of Washington of the adult life. And they were young enough. We really
2:26:19 kept like our home life pretty sheltered from everything else. And we were able to do so because
2:26:24 they were so young. And because they weren’t connected to the internet, they were too young
2:26:29 for smartphones, all of these things, we were able to shelter and protect them and allow them to have
2:26:37 as normal as upbringing as was possible in the context we were living. And
2:26:45 they brought me and continued to bring me so much joy. But they were, I mean, without Jared and
2:26:53 without the kids, it would have been much more lonely. So three kids, you’ve now upgraded two dogs
2:27:02 in a hamster? Well, our second dogs, we rescued him thinking, we thought he was probably like part
2:27:08 German shepherd, part lab is what we were told. He’s now, I don’t even know if he qualifies as a
2:27:15 dog, he’s like the size of a horse, a small horse, Simba. So I don’t think he has much lab in him.
2:27:23 We, Joseph has not wanted to do a DNA test. Because he really wanted a German shepherd,
2:27:29 so he’s a German shepherd. He’s gigantic. And we also have a hamster, who’s the newest edition,
2:27:36 because my son Theo, he tried to get a dog as well. Our first dog winter
2:27:43 became my daughter’s dog, as she wouldn’t let her brothers play with him or sleep with him and was
2:27:48 old enough to bully them into submission. So then Joseph wanted a dog and got Simba. Theo now wants
2:27:56 the dog and has busted the hamster in the interim. So we’ll see. What advice would you give to other
2:28:03 mothers just planning on having kids and maybe advice yourself on figuring out this puzzle?
2:28:13 I think being a parent, you have to cultivate within yourself like heightened levels of empathy.
2:28:17 You have to really look at each child and see them for who they are,
2:28:27 what they enjoy, what they love, and meet them where they’re at. And I think
2:28:34 that can be enormously challenging when your kids are so different in temperament. As they get older,
2:28:38 that difference in temperament may be within the same child, depending on the moment of the day.
2:28:49 But I think it’s actually made me a much softer person, a much better listener. I think I see people
2:28:58 more truly for who they are as opposed to how I want them to be sometimes. And I think being a
2:29:04 parent to three children who are all exceptional and all incredibly different has enabled that in
2:29:12 me. I think for me, though, they’ve also been some of my greatest teachers in that we were talking
2:29:19 about the presence you felt when you were in the jungle and the connectivity you felt and
2:29:26 sort of the simple joy. And I think for us as we grow older, we kind of disconnect from that.
2:29:32 Like my kids have taught me how to play again. And that’s beautiful. I remember just a couple
2:29:37 of weeks ago, we had one of these crazy Miami torrential downpours, and Arabella comes down.
2:29:45 It’s around eight o’clock at night. It’s really raining. And she’s got rain boots and pajama
2:29:50 pants on, and she’s going to take the dogs for a walk in the rain, which she had all day to walk.
2:29:54 But she wasn’t doing it because they needed to go for a walk. She was like, “This would be fun.”
2:30:00 And I’m standing at the doorstep watching her, and she goes out with Simba and Wincher,
2:30:06 this massive dog and this little tiny dog. And I’m watching her walk to the end of the driveway,
2:30:11 and she’s just dancing, and it’s pouring. And I took off my shoes, and I went out, and I joined
2:30:18 her. And we danced in the rain. And even as a preteen who normally, she allowed me to experience
2:30:25 the joy with her. And it was amazing. We can be so much more fun if we allow ourselves to be more
2:30:32 playful. We can be so much more present. I look at Theo loves games. So we play a whole lot of board
2:30:39 games, any kind of game. So it started with board games. We do a lot of puzzles that have
2:30:44 become card games. I just taught him how to play poker. He loves backgammon, like any kind of game.
2:30:52 And he’s so fully in them. When he plays, he plays. My son, Joseph, he loves nature.
2:30:58 And he’ll say to me sometimes when I’m taking a picture of something he’s observing,
2:31:01 like a beautiful sunset, he’s like, “Mom, just experience it.”
2:31:11 Yes, you’re right, Joseph, just experience it. So those kids have taught me so much about
2:31:18 sort of reconnecting with what’s real and what’s true and being present in the moment and experiencing
2:31:23 joy. They always give you permission to sort of reignite the inner child, be a kid again.
2:31:30 And it’s interesting what you said that the puzzle of noticing each human being, like what makes
2:31:36 them beautiful, that the unique characteristics, like what they’re good at, the way they want to be
2:31:49 mentored. I often see that, especially with coaches and athletes, young athletes aspiring to be great,
2:31:57 each athlete needs to be trained in a different way. For example, with some you need a softer
2:32:04 approach. Like with me, I always like a dictatorial approach. I like the coach to be this menacing
2:32:10 figure. That brought out the best in me. I didn’t want to be friends with the coach. I want to,
2:32:17 almost, it’s weird to say, but yell that to be pushed. But that doesn’t work for everybody.
2:32:23 And that’s a risk you have to take in the coach context of like, because you can’t just yell at
2:32:31 everybody. You have to figure out what does each person need. And when you have kids,
2:32:34 I imagine the puzzle is even harder. And when they all need different things,
2:32:40 but yet coexist and are sometimes competitive with one another. So you’ll be at a dinner table,
2:32:45 the amount of times they get, well, that’s not fair. Life isn’t fair. And by the way,
2:32:51 like, I’m not here to be fair. I’m trying to give you each what you need, especially when I’ve been
2:32:55 working really hard. And in the White House, I’d say, okay, well, now we have a Sunday and we
2:33:01 have these hours and I’ll have like a grand plan, you know, and we’re going to make a count. And
2:33:08 it’s going to involve, you know, hot chocolate and sleds, you know, whatever, whatever it is that,
2:33:13 like, my great adventure, that we’re going to go play mini golf. And then I come down,
2:33:20 all psyched up, all ready to go. And the kids have zero interest. And there have been a lot of
2:33:24 times where I’ve been like, we’re doing this thing. And then I realized, wait a second, you know,
2:33:29 like, sometimes you just like plop down on the floor and start playing magnet tiles,
2:33:36 you know, and like, that’s where they need you. And so, so those of us who have sort of like alpha
2:33:43 personalities, who sometimes it’s just, just witness, like witness what they need, don’t like
2:33:49 play with them and allow them to lead the play, don’t force them down a road you may think is
2:33:55 more interesting or productive or educational or edifying, you know, just, just be with them,
2:34:03 observe them and, and then show them that you are genuinely curious about the things that
2:34:07 they are genuinely curious about. I think there’s a lot of love when you do that.
2:34:13 Also, there’s just fascinating puzzles. I was talking to a friend yesterday and she has four kids
2:34:21 and they fight a lot. And she, she generally wants to break up the fights. But she’s like,
2:34:28 I’m not sure if I’m just supposed to let them fight. Can they figure it out? But you always break
2:34:32 break them up because I’m told that it’s okay for them to fight kids do that. They kind of figure
2:34:37 out their own situation. That’s part of like the growing up process. But you want to always,
2:34:42 especially if it’s physical, they’re like pushing each other, you want to kind of stop it. But at
2:34:47 the same time, it’s also part of the play, part of the dynamics. That’s a puzzle you also have to
2:34:52 figure out. And plus you’re probably worried that they’re going to get hurt. If they’re,
2:34:57 I think there’s like, when it gets physical, that’s like, okay, we have to intervene. I know you’re
2:35:04 into martial arts, but that’s normally like the red line. You know, once it, once it tips into that.
2:35:09 But there is always that, you know, like you have to allow them to problem solve for themselves,
2:35:15 like a little interpersonal conflict is good. It’s really hard when you try to navigate something
2:35:19 because everyone thinks you’re taking their side, you have oftentimes incomplete information.
2:35:27 It’s, I think for parents, what tends to happen to is we see our kids fighting with each other
2:35:34 in a way that all kids do. And we start to project into the future and like catastrophize.
2:35:41 You know, if like my two sons are going through a moment where they’re like oil and water,
2:35:46 anything one wants to do, the other doesn’t want to do, it’s like a very interesting moment.
2:35:50 So my instinct is they’re not going to like each other when they’re 25. You know, you sort of
2:35:56 project into the future as opposed to recognizing this is a stage that I too went through. And
2:36:06 it’s normal and not building it in your mind into, into something that’s unnecessarily consequential.
2:36:16 It’s short term formative conflict. Yeah. So ever since 2016, the, the number and the
2:36:21 level of attacks you’ve been under has been steadily increasing has been super intense.
2:36:30 How do you walk through the fire of that? You’ve been very stoic about the whole thing. I don’t
2:36:37 think I’ve ever seen you respond to an attack. You just let it pass over you and you stay positive
2:36:44 and you focus on solving problems and you didn’t engage while being in DC, you didn’t engage into
2:36:49 the back and forth fire of the politics. So what’s your philosophy behind that?
2:36:55 I appreciate your saying that I was very stoic about it. I think, you know, I feel things pretty
2:37:04 deeply. So initially, some of that really took me off guard. Like some of the derivative love
2:37:13 and hatred, some of the intensity of, of, of the attacks. And there were times when it was,
2:37:20 it was so easy to counter it. I’d even write something out and, and say, well, I’m gonna,
2:37:28 I’m gonna press send and never did. I felt that sort of getting into the mud, fighting back,
2:37:36 it didn’t run true to who I am as a human being. Like it didn’t, it felt at odds with, with who I
2:37:42 am and how I want to spend my time. So I think as a result, I was oftentimes on the receiving end
2:37:47 of a lot of, a lot of cheap shots. And I’m okay with that because it’s sort of the way I know how
2:37:54 to be in the world. I was focused on things I thought mattered more. And, you know, I think part
2:38:03 of me also internalize, there’s a concept in Judaism called Lushanhara, which is translated into,
2:38:11 I think, quite literally evil speech. And the idea that, you know, speaking poorly of another,
2:38:19 is almost the moral equivalent to murder. Because you can’t really repair it. You can
2:38:25 apologize, but you can’t repair it. Another component of that is that it does as much damage to the
2:38:33 person saying the words than it does to the person receiving them. And I think about that a lot.
2:38:40 I talk about this concept with, with my kids a lot. And I’m not willing to pay the price
2:38:48 of that fleeting and momentary satisfaction of, of sort of swinging back. Because I think it would
2:38:56 be, it would be too expensive for my soul. And, and that’s how I kind of made peace with it. Because
2:39:04 I think that’s just, that feels more true for me. But it is a little bit contrary in politics.
2:39:14 It’s definitely, it’s definitely a contrarian viewpoint to not get into the fray. Actually,
2:39:21 someday I love Dolly Parton says that she doesn’t condemn or criticize, she loves and accepts.
2:39:24 And I like that it feels, it feels right for me.
2:39:31 I also like that you said that words have power. It’s not sometimes people say, well, words,
2:39:38 when you speak negatively of others, that’s just words. But I think there’s a cost to that.
2:39:43 There’s a cost like you said to your soul. And there’s a cost in terms of the damage you can do
2:39:48 to the other person, whether it’s to their reputation publicly, or to them privately,
2:39:55 just as a human being psychologically. And in the place that it puts them, because they think,
2:39:58 they start thinking negatively in general, and then maybe they respond and there’s this vicious
2:40:03 downward spiral that happens. They’re almost like we don’t intend to, but it destroys everybody in
2:40:12 the process. You quoted Alan Watts, I love him, in saying, quote, you’re under no obligation
2:40:19 to be the same person you were five minutes ago. So how have the years in DC and the years after
2:40:29 changed you? I love Alan Watts too. I listened to his lecture sometimes falling asleep. He’s
2:40:34 got like an on plane. He’s got like the most soothing voice. But I love what he said about
2:40:38 you have no obligation to be who you were five minutes ago, because we should always feel that
2:40:46 we have the ability to evolve and grow and better ourselves. I think further than that,
2:40:52 if we don’t look back on who we were a few years ago, with some level of embarrassment,
2:40:57 we’re not growing enough. So there’s nothing, when I look back, I’m like, oh,
2:41:08 I feel like that feeling is, because you’re growing into hopefully sort of a better version
2:41:15 of yourself. And I hope and feel that that’s been true for me as well. I think the person I am today
2:41:25 we spoke in the beginning of our discussion about some of my earliest ambitions in real
2:41:32 estate and in fashion. And those were amazing adventures and incredible experiences in government.
2:41:40 I feel today that all of those ambitions are more fully integrated into me as a human being.
2:41:47 I’m much more comfortable with the various pieces of my personality and that any professional
2:41:53 drive is more integrated into more simple pleasures. Everything for me has gotten much simpler and
2:42:01 easier in terms of what I want to do and what I want to be. And I think that’s where my kids
2:42:08 have been my teachers just being fully present and enjoying the little moments. And it doesn’t
2:42:18 mean I’m any less driven than I was before. It’s just more a part of me than being sort of the
2:42:23 all-consuming energy one has in their 20s. Yeah, just like you said, will your mom be able to let
2:42:32 go and enjoy the water, the sun, the beach and enjoy the moment, the simplicity of the moment.
2:42:35 I think a lot about the fact that for a lot of young people,
2:42:42 they really know what they want to do, but they don’t actually know who they are.
2:42:48 And then I think as you get older, hopefully you know who you are and you’re much more comfortable
2:42:54 with ambiguity around what you want to do and accomplish. You’re more flexible in your thinking
2:42:57 around those things. And give yourself permission to be who you are. Yeah.
2:43:05 You made the decision not to engage in the politics of the 2024 campaign. If it’s okay,
2:43:12 let me read what you wrote on the topic, quote, “I love my father very much. This time around,
2:43:17 I’m choosing to prioritize my young children and the private life we’re creating as a family.
2:43:22 I do not plan to be involved in politics. While I will always love and support my
2:43:27 father going forward, I will do so outside the political arena. I’m grateful to have had the
2:43:33 honor of serving the American people and I will always be proud of many of our administration’s
2:43:38 accomplishments.” So, can you explain your thinking, your philosophy behind that decision?
2:43:45 I think first and foremost, it was a decision rooted in me being a parent,
2:43:55 really thinking about what they need from me now. Politics is a rough business,
2:43:59 and I think it’s one that you also can’t dabble in. I think you have to either be
2:44:07 all in or all out, and I know today the cost they would pay for me being all in.
2:44:18 Emotionally, in terms of my absence at such a formative point in their life,
2:44:25 and I’m not willing to make them bear that cost, I serve for four years and feel
2:44:31 so privileged to have done it. But as their mom, I think it’s really important that
2:44:36 I do what’s right for them. And I think there are a lot of ways you can serve.
2:44:42 I think there’s, obviously, we talked about the enormity, the scale of what can be accomplished
2:44:50 in government service, but I think there’s something equally valuable about helping
2:44:56 within your own community. I volunteer with the kids a lot, and we feel really good about
2:45:03 that service. It’s different, but it’s no less meaningful. I think there are other ways to serve.
2:45:13 I also think politics is a pretty dark world. There’s a lot of darkness, a lot of negativity,
2:45:24 and it’s just really at odds with what feels good for me as a human being, and it’s a really rough
2:45:32 business. So for me and my family, it feels right to not participate.
2:45:38 So it wears on your soul, and yeah, there is a bit, at least from an outsider’s perspective,
2:45:44 a bit of darkness in that part of our world. I wish it didn’t have to be this way.
2:45:50 Me too. I think part of that darkness is just watching all the legal turmoil that’s going on.
2:45:57 What’s it like for you to see your father involved in that, going through that?
2:46:07 On a human level, it’s my father, and I love him very much, so it’s painful to experience,
2:46:10 but ultimately, I wish it didn’t have to be this way.
2:46:15 I like it that underneath all this, I love my father is the thing that you lead with,
2:46:24 and that’s so true. It is family, and I hope I missed all this turmoil. Love is the thing that
2:46:31 wins. It usually does. In the end, yes, but in the short term there is, like we were talking about,
2:46:38 there’s a bit of bickering, but at least no more duels. No more duels. You mentioned Dolly Parton.
2:46:42 That’s a segue.
2:46:49 Listen, I’m not very good at this thing. I’m trying to figure it out. Okay, we both love Dolly Parton.
2:46:57 So, you’re big into live music, so maybe you can mention why you love Dolly Parton.
2:47:00 I definitely would love to talk to her. I would love to interview her. She’s such an icon.
2:47:08 What I love about her, and I’ve really come to love her in recent years, is she’s so authentically
2:47:15 herself. She’s obviously so talented and so accomplished, and this extraordinary woman,
2:47:22 but I just feel like she has no conflict within herself as to who she is. She reminds me a lot
2:47:31 of my mom in that way, and it’s super refreshing and really beautiful to observe somebody who’s so
2:47:37 in the public eye, being so fully secure in who they are, what their talent is, and what drives
2:47:44 them, so I think she’s amazing. She leads with a lot of love and positivity, so I think she’s
2:47:48 very cool. I hope you have a long conversation with her. Yeah, she’s like, okay, so there’s many
2:47:55 things to say about her. First, incredibly great musician, songwriter, performer, also can create
2:48:02 an image and have fun with it. Have fun being herself over the top. It feels that way, right?
2:48:08 She enjoys, after all these years, it feels like she enjoys what she does,
2:48:11 and you also have the sense that if she didn’t, she wouldn’t do it.
2:48:19 That’s right, and just an iconic country musician, country music singer. There’s a lot,
2:48:23 we’ve talked about a lot of musicians. What do you enjoy? You mentioned Adele seeing her perform,
2:48:28 hanging out with her. Yeah, I mean, she’s extraordinary. Her voice is
2:48:36 unreal, so I find her to be so talented. She’s so unique in that three-year-olds love her music.
2:48:41 She was actually the first concert Arabella ever went to at Madison Square Garden when
2:48:47 she was around four, and nine-year-olds love her music. That’s pretty rare to have that kind of
2:48:53 bandwidth of resonance, so I think she’s so talented. We actually just saw her. I took all
2:49:01 three kids in Las Vegas around a month ago. Alice Johnson, whose case I had worked with in the White
2:49:08 House, my father commuted her sentence. Her case was brought to me by a friend, Kim Kardashian,
2:49:16 and she came to the show. We all went together with some mutual friends. I was a very profound.
2:49:21 It was amazing to see Adele, but it was a very profound experience for me to have with my kids
2:49:25 because she rode with us in the car on the way to the show, and she talked to my kids about
2:49:34 her experience and her story and how her case found its way to me. I think for young children,
2:49:41 it’s very abstract policy. For her to be able to share with them this was a very beautiful
2:49:48 moment and led to a lot of really incredible conversations with each of my kids about our
2:49:54 time in service because they gave up a lot for me to do it. Actually, Alice told them the most
2:50:00 beautiful story about the plays she used to put on in prison, how these shows were the hottest ticket
2:50:06 in town. You could not get into them. They always extended their run, but for the people who were
2:50:15 in them, a lot of those men and women had never experienced applause. Nobody had ever shown up
2:50:23 at their games or at their plays and clapped for them. The emotional experience of just being able
2:50:31 to give someone that, being able to stand and applaud for someone and how meaningful that was.
2:50:36 She was showing us pictures from these different productions. It was a really beautiful moment.
2:50:44 Alice actually, after her sentence was commuted and she came out of prison, together we worked on
2:50:55 23 different pardons or commutations. The impact of her experience and how she was able to take
2:51:02 her opportunity and create that same opportunity for others who were deserving and who she believed
2:51:08 in was very beautiful. Anyway, that was an extraordinary concert experience for my kids
2:51:16 to be able to have that moment. What a story. Then here we are dancing at Adele.
2:51:23 Six years later, it was almost to the day, six years later. That policy, that meeting of the
2:51:28 Miser’s ultimate major turning point in her life and Alice’s life, and now you’re dancing with Adele.
2:51:36 And now we’re at Adele. You mentioned also there, I’ve seen commutations where it’s an
2:51:44 opportunity to step in and consider the ways that the justice system does not always work well.
2:51:51 I can cases when it’s nonviolent crime and drug offenses, there’s a case of a person
2:51:57 you mentioned that received a life sentence for selling weed.
2:52:05 And it’s just the number, it’s like hundreds of thousands of people are in the federal prison
2:52:13 and jail in the system for selling drugs. That’s the only thing with no violence on their record
2:52:18 whatsoever. And obviously, there’s a lot of complexity. There’s the details matter, but
2:52:26 oftentimes the justice system does not do right in the way we think right is. And it’s nice to be
2:52:35 able to step in and help people. They’re overlooked and they have no advocate. Jared and I helped in
2:52:40 a small way on his effort, but he really spearheaded the effort on criminal justice reform
2:52:46 through the First Step Act, which was an enormously consequential piece of legislation
2:52:52 that gave so many people another opportunity. And that was amazing. So working with him closely on
2:52:57 that was a beautiful thing for us to also experience together. But in the final days of the
2:53:03 administration, you’re not getting legislation passed. And anything you do administratively is
2:53:09 going to be probably overturned by an incoming administration. So how do you use that time
2:53:15 for maximum results? And I really dug in on pardons and commutations that I thought were
2:53:26 overdue and were worthy. And my last night in Washington, D.C., the gentleman you mentioned,
2:53:33 Corvin, I was on the phone with his mother at 12.30 in the morning telling her that her son
2:53:39 would be getting out the next day. And it felt really, it’s one person, but you see with Alice,
2:53:45 like the ripple effect of the commutation granted to her and her ability and the impact she’ll have
2:53:51 within her family with her grandkids. And now she’s an advocate for so many others who are
2:53:59 voiceless. It felt like the perfect way to end four years to be able to call those parents and
2:54:03 call those kids in some cases and give them the news that a loved one was coming home.
2:54:08 And now I just love the cool image of you, Kim Kardashian and Alice just dancing on Adele’s show
2:54:14 with the kids. I love it. Well, Kim wasn’t at the Adele’s show, but she had connected us. It was
2:54:25 beautiful. Yeah, the way Adele can hold just the bad assness she has on stage. She does heartbreak
2:54:31 songs better than anyone. Or no, it’s not even heartbreak. What’s that genre of song,
2:54:38 like rolling in the deep, a little anger, a little love, a little attitude, and just one of the
2:54:44 greatest voices ever. All of that together just by herself. Yeah, you can strip it down and the
2:54:49 power of her voice. You know, I think about that. One of the things we were talking about live music,
2:54:56 one of the amazing things now is there’s so much incredible concert material that’s been
2:55:02 uploaded to YouTube. So sometimes I just sit there and watch these old shows. We both love
2:55:07 Stevie Ray Vaughn, like watching him perform. You can even find old videos of like Django Reinhardt.
2:55:12 You got me. I got you. Texas Flood. We had this moment, which is hilarious,
2:55:17 that you said like one of the songs you really like of Stevie’s is Texas Flood.
2:55:23 Well, my bucket list is to learn how to play it. It’s a bucket list. You made me feel so good,
2:55:28 because for me, Texas Flood was the first solo on guitar I’ve ever learned, because for me it was
2:55:36 like the impossible solo. And then that was, so I worked really hard to learn it. It’s like one of
2:55:44 the most iconic sort of blues songs, Texas blues songs. And now you made me fall in love with the
2:55:49 song again, want to play it out live, at the very least put it up on YouTube. Because it is,
2:55:54 it’s so fun to improvise it. And when you lose yourself in the song, it truly is a blues song.
2:55:59 You can have fun with it. I hope you do do that, and regardless, I want you to play it for me.
2:56:07 100%. But he’s amazing. And there’s so many great performers that are playing live now.
2:56:13 I just saw Chris Stapleton show. He’s an amazing country artist. He’s too good.
2:56:19 He’s so good. That guy is so good. Lucas Nelson’s one of my favorite to see live. And there’s so
2:56:25 many incredible songwriters and musicians that are out there touring today. But I think you also,
2:56:30 you can go online and watch some of these old performances like Django Reinhardt was the first,
2:56:36 because I torture myself, was the first song I learned to play on the guitar. And it took me
2:56:41 like nine months to a year. It was, I mean, I should have chosen a different song, but Ue2
2:56:48 Monomor, one of his songs was, and it was like finger style. And I was just going through and
2:56:54 grinding it out. And that’s kind of how I started to learn to play by playing that song.
2:57:00 But to see these old videos of him playing without all his fingers and the skill and the
2:57:06 dexterity, one of my favorite live performances is actually who really influenced Adele as Aretha
2:57:14 Franklin. And she did this, she did a version of Amazing Grace. Have you ever seen this video?
2:57:20 No. I cry. Look up. It was in LA. It was like the temple missionary Baptist church.
2:57:25 Talk about stripped down. She’s literally, I mean, just listen to this.
2:57:36 You could do one note and you could just kill it.
2:57:45 The pain, the soulfulness. The spirit you feel in her when you watch this.
2:57:50 That’s true. Adele carries some of that spirit also, right? Yeah.
2:57:56 And you can take away all the instruments with Adele and just have that voice. And it’s so
2:58:05 commanding and it’s so amazing. Anyway, you watch this and you see like the arc of also
2:58:11 the experience of the people in the choir and them starting to join in. And it’s anyway, it’s
2:58:16 amazing. I love watching Queen, like Freddie Mercury, Queen performances. Like in terms of
2:58:21 vocals and just like great stage presence. Well, that live aid performance is considered one of
2:58:26 the best of all. I’ve watched that so many times. He’s so cool. Can we pull up that for a second?
2:58:32 Go to that part where he’s saying radiogaga and they’re all
2:58:35 mimicking at his arm movements. It’s so cool.
2:58:47 Look at that. I miss that guy. So good. So that’s an example of a person that was born to be on
2:58:54 stage. So good. Well, we were talking surfing. We were talking jiu-jitsu. I think live music is one
2:59:02 of those kind of rare moments where you can really be present. Where something about the
2:59:06 anticipation of choosing what show you’re going to go to and then waiting for the date to come.
2:59:12 And normally it happens in the context of community. You go with friends and then allowing
2:59:21 yourself to sort of fall into it is incredible. So you’ve been training jiu-jitsu. Yes. Trying.
2:59:28 I mean, I’ve seen you do jiu-jitsu. You’re extremely, you’re very athletic. You know,
2:59:35 you know how to use your body to commit violence. There’s better ways of phrasing that. But anyway.
2:59:41 It’s been a skill that’s been honed over. I mean, what do you like about jiu-jitsu?
2:59:48 Well, first of all, I love the way I came to it. It was my daughter. I think I told you this
2:59:56 story. She’s at 11. She told me that she wanted to learn self-defense and she wanted to learn how
3:00:01 to protect herself, which I just, as a mom, I was so proud about because at 11, I was not thinking
3:00:06 about defending myself. You know, I loved that she had sort of that desire and awareness.
3:00:14 So I called some friends, actually a mutual friend of ours and asked around for people
3:00:19 who I could work with in Miami and they recommended the Valentae Brothers Studio. And
3:00:26 you’ve met all three of them now. They’re these remarkable human beings and they’ve been so wonderful
3:00:30 for our family. I mean, first starting with Arabella, I used to take her and then she’d kind
3:00:34 of encouraged me and she’d sort of pull me into it. And I started doing it with her and then
3:00:42 Joseph and Theo saw us doing it. They wanted to start doing it. So now they joined and then
3:00:48 Jared joined. So now we’re all doing jiu-jitsu. And for me, there’s something really empowering,
3:00:54 knowing that I have some basic skills to defend myself. I think it’s something as humans we’ve
3:01:01 kind of gotten away from. You look at any other animal and even the giraffe, they’ll use their
3:01:10 neck, the lion, the tiger, every species. And then there’s us, who most of us don’t and I didn’t
3:01:15 know how to protect myself. And I think that it gives you a sense of confidence and also gives
3:01:21 you kind of a sense of calm, knowing how to de-escalate rather than escalate a situation.
3:01:35 I also think as part of the training, you develop more natural awareness when you’re out and about.
3:01:39 And I feel like especially, you know, everyone’s, you get on an elevator and like the first thing
3:01:43 people do is pick up their phone. You’re walking down the street. People are getting hit by cars
3:01:48 because they’re walking into traffic. I think as you start to get this training, you become much more
3:01:55 aware of the broader context of what’s happening around you, which is really healthy and good
3:02:02 as well. But it’s been beautiful. Actually, the Valente brothers, they have this 753 code that was
3:02:10 developed with some of the sort of samurai principles in mind. And all of my kids have
3:02:16 memorized it and they’ll talk to me about it at Theo. He’s eight years old. He’ll be able to recite
3:02:26 all 15. So, you know, benevolence and fitness and nutrition and flow and awareness and balance. And
3:02:33 it’s an unbelievable thing. And they’ll actually integrate it into conversations where they’ll
3:02:39 talk about something that happened. Yeah, rectitude, courage. Benevolence, respect, honesty, honor,
3:02:44 loyalty. So this is not about jujitsu techniques or fighting techniques. This is about a way of life,
3:02:49 about the way you interact with the world with other people. Exercise, nutrition, rest,
3:02:53 hygiene, positivity. That’s more on the physical side of things. Awareness, balance, and flow.
3:02:59 It’s the mind, the body, the soul, effectively is how they break it out. And the kids can only
3:03:04 advance and get their stripes if they really internalize this. They give examples of each of
3:03:09 them. And my own kids will come home from school and they’ll tell me examples of how things happened
3:03:18 that weren’t aligned with the 753 code. So it’s a framework, much like religion is in our house and
3:03:24 can be for others. It’s a framework to discuss things that happen in their life, large and small,
3:03:32 and has been beautiful. So I do think that body, mind, connection is super strong in jujitsu.
3:03:38 So there’s many things I love about the Valenti brothers. But one of them is how rooted it is
3:03:43 in philosophy and history of martial arts in general. A lot of places, you’ll practice the
3:03:49 sport of it, maybe the art of it, but to recognize the history and what it means to be a martial
3:03:54 artist broadly on and off the mat. That’s really great. And the other thing is great is they also
3:03:59 don’t forget the self-defense route, the actual fighting routes. So it’s not just the sport,
3:04:04 it’s a way to defend yourself on the street in all situations. And that gives you a confidence.
3:04:09 And just like you said, an awareness about your own body and awareness about others.
3:04:17 It is, sadly, we forget, but it’s a world full of violence or the capacity for violence,
3:04:22 so it’s good to have an awareness of that and a confidence how to essentially avoid it.
3:04:29 100%. I’ve seen it with all of my kids and myself, how much they benefited from it. But
3:04:37 that self-defense component and the philosophical elements of… They, Pedro, will often tell them
3:04:48 about Wu Wei and soft resistance and some of these more Eastern philosophies that they get
3:04:59 exposed to through their practice there that are non-resistance, that are beautiful and hard concepts
3:05:07 to internalize as an adult, but especially when you’re 12, 10, and eight, respectively.
3:05:13 So it’s been an amazing experience for us all. I love people like Pedro because he’s finding
3:05:19 books there in Japanese and translating them to try to figure out the details of a particular
3:05:26 history. He’s like an ultra scholar of martial arts, and I love that. I love when people give
3:05:32 everything, every part of themselves, to the thing they’re practicing. People have been fighting
3:05:38 each other for a very long time, and I love, from the Colosseum on, you can’t fake anything,
3:05:45 you can’t lie about anything. It’s truly honest. You’re there, and you either win or lose. It’s
3:05:50 simple, and it’s also humbling. The reality of that is humbling.
3:05:55 And oftentimes in life, things are not that simple, not that black and white.
3:06:00 So it’s nice to have that sometimes. That’s the biggest thing I gained from Jujitsu is getting
3:06:06 my ass kicked, which is the humbling. And it’s nice to just get humbled in a very clear way.
3:06:11 Sports in general are great for that. I think surfing probably, because I can imagine just,
3:06:17 you know, yeah, face planting, not being able to stay on the board, it’s humbling.
3:06:23 And the power of the wave is humbling. See, just like your mom, you’re an adventurer.
3:06:28 Are there, your bucket list is probably like 120 pages.
3:06:34 Is there things like just popped to mind that you’re like thinking about,
3:06:39 especially in the near future, just anything? Well, I hope it always is long. You know, I hope I’ve
3:06:44 never like exhausted exploring all the things I’m curious about. I always tell my kids whenever
3:06:50 they say, you know, “Mom, I’m bored.” Only boring people get bored. There’s too much to learn.
3:06:55 There’s too much to learn. So I’ve got a long one. I, you know, I think obviously there are some like
3:07:01 immediate tactical, you know, interesting things that I’m doing. I’m incubating a bunch of businesses.
3:07:06 I’m investing in a bunch of companies that hopefully I’ll always can continue to do that.
3:07:11 Some of the fun things I’m doing in real estate now. So those are all on the list of things I’m
3:07:17 passionate and excited about continuing to explore and learn. But in terms of the like the ones that
3:07:23 are more pure sort of adventure or hobby, I think I’d like to climb Mount Kilimanjaro. Actually,
3:07:28 I know I would. And I, the only thing keeping me from doing it in the short term is I feel like
3:07:34 it’d be such a great experience to do with my kids. And I’d love to have that experience with them.
3:07:38 I also told at Herbella, we were talking about this archery competition that happens in Mongolia,
3:07:43 and she loves horseback riding. So I’m like, I feel like that would be an amazing thing to experience
3:07:51 together. I want to get barreled by a wave and learn how to play Texas Flood. I want to see the
3:08:00 northern lights, like I want to go and experience that. I feel like that would be really beautiful.
3:08:09 I want to get my black belt like you have. I asked you, how long did it take? But so I want to get
3:08:13 my black belt and jiu jitsu. That’s like, that’s going to be a longer term goal, but within the
3:08:22 next decade. Yeah, a lot of things. You know, I’d love to go to space. Not just space. I think
3:08:29 I’d love to go to the moon. Like step on the moon. Yeah. Or float, you know, in close proximity,
3:08:38 like that famous photo. Yeah, just you and the space dude. I feel like Mars is at this point
3:08:45 in my life. Well, the moon’s like four days feels more manageable. But the sunset on Mars is blue.
3:08:50 It’s the opposite color. I hear it’s beautiful. It might be worth it. I don’t know. You negotiate
3:08:56 with Theo. Yeah. Let me know how it goes. Let me know how it goes. I think actually just even
3:09:02 go into space, we can look back on Earth. Yeah. I think that just to see this little
3:09:10 pale blue dot, pale blue dot, just all the stuff that ever happened in human civilization is on
3:09:16 that and to be able to look at it and just be in awe. I don’t think that’s the thing that will go away.
3:09:22 I think being interplanetary, my hope is that that heightens for us how
3:09:28 rare it is what we have, like how precious the Earth is.
3:09:36 I hope that it has that effect. Because I think there’s a big component to
3:09:45 interplanetary travel that kind of taps into this kind of manifest destiny inclination,
3:09:54 like the human desire to conquer territory and expand the footprint of civilization
3:10:02 that sometimes feels much more rooted in dominance and conquest than curiosity, wonder.
3:10:11 Obviously, I think there’s maybe an existential imperative for it at some point,
3:10:21 or a strategic and security one. But I hope that what feels inevitable at this moment,
3:10:26 I mean, Elon Musk and what he’s doing with SpaceX and Jeff Bezos and others,
3:10:33 it feels like it’s not an if, it’s a when at this point. I hope it also underscores the need
3:10:40 to protect what we have here. Yeah. I hope it’s the curiosity that drives that exploration,
3:10:45 and I hope the exploration will give us a deeper appreciation of the thing we have
3:10:50 back home. And the Earth will always be home, and it’s a home that we protect and celebrate.
3:10:57 What gives you hope about the future of this thing we have going on, human civilization,
3:11:03 the whole thing? I think I feel a lot of hope when I’m in nature. I feel a lot of hope when
3:11:12 I am experiencing people who are good and honest and pure and true and passionate,
3:11:19 and that’s not an uncommon experience. So those experiences give me hope.
3:11:21 Yeah, other humans. We’re pretty cool.
3:11:29 I love humanity. We’re awesome. Not always, but we’re pretty good species.
3:11:34 Yeah, for the most part, on the whole, we do all right. We do all right. We create some beautiful
3:11:39 stuff, and I hope we keep creating, and I hope you keep creating. You have already
3:11:44 done a lot of amazing things, build a lot of amazing things, and I hope you keep building
3:11:52 and creating and doing a lot of beautiful things in this world. Ivanka, thank you so much for talking
3:11:58 today. Thank you, Lex. Thanks for listening to this conversation with Ivanka Trump. To support
3:12:03 this podcast, please check out our sponsors in the description. And now, let me leave you with
3:12:12 some words from Marcus Aurelius. “Dwell on the beauty of life. Watch the stars and see yourself
3:12:29 running with them.” Thank you for listening. I hope to see you next time.
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