Ivanka Trump on Building an Authentic Life

Right now in your life today, what is the most exciting part of your work life?

My work life, specifically. I think I have gotten to a place where I know myself, I know what I love, I know what I'm good at, I know what excites me, and where I can sustain this excitement over a long period of time, which is critical because I've really lived so many different lives. So now, everything I apply myself to, I can do it with a lot of vigor, but also a lot of confidence that this is something I'm passionate about.

The things I'm doing right now that I really love and that I spring out of bed each morning to do are super mission-driven. Whether it's incubating companies, from for-profit to nonprofit businesses, investing in companies and founders that are really right at the edge of transformation—whether that be AI, biotech, neurotech, robotics, or even space—these are things that satisfy a huge curiosity for me and enable me to learn, grow, and expand, alongside founders who are taking on meaningful problems.

What inspires me is people really swinging for things. I love individuals with huge imaginations and huge ideas. The ability to learn from them, to spend time with them, and to be expanded by them is super interesting. I've also gotten back to my real estate roots, which has been a lot of fun, and I'm working on an incredible project with my husband in the Mediterranean. It's massive in scale.

I think that's an understatement. Can you explain?

Yes, it is very.

I mean, there's no power on this island.

Yeah.

You're building everything from scratch. Correct?

Well, it's an unbelievable, beautiful, 1,400-acre private island in the middle of the Mediterranean. We were on a friend's boat, and we stopped for a swim. Effectively, that's how we found it. We swam to the island, went on a hike barefoot all the way up to the top, and we were just captivated. It stayed with us ever since.

Over the course of many years, we developed the opportunity to help realize its potential and transform it, but with a lot of restraint and care because the land is so beautiful that the architecture has to be fully integrated into it, almost rise from it. It's not even a business for me, despite the scale of it. Not only do we have the island, but we have 5 miles of beachfront directly across from it: this beautiful peninsula with a lagoon on one side, the ocean on the other, and beautiful white-sand beaches.

For me, it feels more like a challenge than anything else. It's the culmination of all of my experience in real estate, all of my travel, and a lot of reflection on how I want to live, how I think people increasingly want to live, and trying to really build something that's a tangible manifestation of that. That requires a lot of vision and the collaboration of some of the greatest masters that exist.

I was just there walking the lands, really trying to be with it and experience it alongside some of the greatest living architects of our time—true masters of their craft, people with integrity so absolute, there will be no compromise. That's something we want to create there. So we're very excited.

What does that mean? People with integrity so complete there's no compromise in their vision? Is that what you mean?

When you work with real artists, regardless of their medium, whether it's a canvas, real estate, a home, or music, they don't compromise. Their integrity is precise and absolute, and they'll push themselves; they'll push everyone around them.

Are you guys hearing this?

There's like 6 people off camera that I badger every day.

That you drive absolutely crazy. But actually, that's where you get to something. Part of it is a push and pull. When you're working with an architect, unless they're building a monument, right, they're building a space that people have to interact with, not just observe like a canvas. They have to live in it. They have to get married in it. If it's a hotel, it's their home.

There are certain functional elements. There's nothing uglier than a beautiful, nonfunctional space. To me, that's not a masterpiece because it wasn't fully thought through. When you combine something that is architecturally incredibly meaningful, beautiful, and intentional with a highly functional space, you create something special.

One of the things I love about real estate is that it's tangible in a world where increasingly everything is not. You see the result of years of work, and really, to bring a project to life, it takes years—sometimes a decade-plus.

It also must feel good because many of the buildings that you've been involved in, this new project—you know it's going to outlive you.

Oh, yeah.

To build something that you know lasts longer than your own lifetime.

One of the things that I love so much is that I've worked on a lot of incredible projects. The Old Post Office in Washington, D.C., was my baby. We acquired this incredible building, built in the 1890s, lovingly restored it, and made it useful in its modern life. It was effectively a dilapidated post office, and now it's a thriving urban hotel.

That was an amazing project that took a very long period of time to bring to life, and it's just one example. But I think the thing I love the most is not only seeing it, because that's great, and experiencing it, and remembering every decision you took through the design and development process, but also that people will stop me and tell me the story of a child's christening—

Mm.

—in one of the ballrooms, or their daughter's wedding. Some experience they had, a milestone life moment, that somebody chose to have happen in a space that I conceived alongside many other talented people. That, to me, is something really beautiful. That's something very, very unique and special about being a builder. You're building the stage for people's lives and the realization of their dreams. That's what we're going to do with this project, Sazan.

Yeah. How do I say it?

Sazan.

Sazan. Okay. I want to go back to something you said that's very interesting. It's one of my favorite things about you. You said, "I know who I am."

Mm.

I was chasing Dana White to get him on the show forever, and he wasn't responding. I texted you, and you were very kind and set that up immediately. Dana has this thing—a simple genius to the way he operates his life, in my opinion, and his business. The piece of advice that he would give to young entrepreneurs is: if you know who you are, which is very difficult to do and takes a long time, if you know who you are and what you want to do, he's like, "The rest of your life is easy."

You already know who you are. You know what you want to do. You just wake up and get after that goal. You started companies early. How old were you when you first started your first company?

I was 22.

You didn't know who you were at 22, correct?

Yeah.

Can you talk about the process that you went through to now say truthfully that you know who you are?

Well, I think if you don't know who you are, the world will tell you, and it may not be an answer you want, right? The world is noisy, especially when you have a certain level of visibility. It projects onto you as much as it receives you. So I think you have to do the work of really getting to know yourself and what feels right.

Some of the hardest decisions I've taken are really about saying no, setting boundaries, or changing course. When those decisions, regardless of how hard they are, align with your values, it always feels good. It's hard. It can be difficult, but you never question it. You never second-guess, and you don't look back and wonder, "What if?"

It's the decisions you take that don't fully feel right, that don't align with your true self and those core values that you hold, that I think you always regret.

Yes.

Oftentimes, people get there because they forum-shop decisions. They'll ask people about their life: "What should I do? What should I do?" They almost make it a process to make tough choices. There's something very important about speaking to people who are knowledgeable and getting perspective and feedback. But ultimately, you can't outsource decision-making as it pertains to major decisions in your personal or professional life. You really have to sit with it.

Actually, I think Dana is a great example of somebody who knows himself so well. He's so authentically who he is. He would be wildly uncomfortable wearing a mask and performing in some other role. I think Rick Rubin—I think so many great people, Dolly Parton.

Mm-hmm.

I love her. She is who she is, she's always been the same, and she really owns it. I think we're drawn, as people, if you look at pop culture, to people who are extremely authentic, especially over time. I think if somebody's in the public eye for a long period of time, and yet so many people I know are really afraid to be themselves, the reality is you're going to get criticized either way. You might as well be the best version of you possible.

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How did you get to the point where, when you were 22 and started your first company, you didn’t know yourself, and now, several years later, you do? How did you do this?

I think people will say, “Trust your instinct,” but instinct has to be developed.

Mm-hmm.

My instinct when I was 22 is different from my instinct today because I think instinct is honed and refined over time. First and foremost, you have to get started. You have to try things, and those micro-wins that felt as big as the massive ones do today help you develop reps and patterns and confidence, which is so important.

It’s really hard to trust yourself or trust your gut if you’re deeply insecure and you haven’t developed a rhythm or had some successes. This could be in entry-level, beginning positions.

Mm-hmm.

I started out in real estate working for a developer in Brooklyn, developing shopping malls, but those little wins I had with the construction teams, or times when I felt like I rose to the occasion, set the foundation for my instincts and for the confidence that would come later.

I also think—and I think this is increasingly true, especially the more demands there are on you and your time, and all of us have this to some degree with social media, text messages, and emails, and the access the world has into the private sanctuary of our homes and our lives through the devices that we carry with us—that it requires a tremendous amount of discipline to create stillness.

I have to be much more intentional about creating a contemplative routine than I did maybe 20 years ago. There’s just a lot more coming at me, so I have to create a lot of boundaries for myself in my day. I wake up and cook the kids’ breakfast. Jared and I cook the kids’ breakfast. They prefer it when he does, in which case I’m the one pushing them out the door. They like his pancakes better.

Your team, by the way, witnessed us running, as always, roughly 2 minutes late for the bus. We always get there on time, but we leave 2 minutes later than we’re supposed to.

This is great.

So we’re currently in a moment where each of my 3 children likes completely different breakfasts, so I’m—

Oh, no.

—I’m basically a short-order chef. I’ve tried to find that one thing that they will all eat, unsuccessfully so far. It used to be easier.

Yeah.

I make breakfast, drop them off at the bus, and then they go to school quite early. I normally have the ability right after drop-off to sit by the ocean. I live here in Miami, and I meditate as the sun rises. I’ll pray, reflect, and think.

I keep that beautiful moment in my day as an anchor to offer thanks and gratitude to God and the universe, but also to reflect on what my priorities are for the day ahead. I’ve found that to be incredibly important and grounding.

I come back to the house, work out, and do all of that in an hour-and-a-half to 2-hour time span. To me, that routine in the morning sets me up for success through the course of the day in terms of less reactivity and being much more proactive, with a clear definition around what I want to accomplish that day.

What everyone else wants me to learn about or accomplish will be secondary, as long as I create clarity for myself around my goals. Then I have some version of that in the evening—a little more challenging because the kids are all home and every night is a different adventure—but I’m really trying to find stillness so I can hear what the universe is telling me.

Rick Rubin talks about this in his book, The Creative Act: the creator ultimately is just super-attuned to what the universe is saying, and the deeper you listen, the more you hear. Part of listening is listening to oneself. If you don’t create space and time for that, I find that it’s very easy to just be on the hamster wheel and be a lot less creative in your pursuits.

It’s funny. I listen to so many people, and they have these eureka moments in the shower, which I do, too.

Mm-hmm.

I think part of the reason that happens is because they don’t have their cell phone in the shower.

No.

Whether it’s 5 minutes or 20 minutes, they’re there alone with their thoughts.

Yeah.

And suddenly the ideas start to come in.

You mentioned The Creative Act. One thing that you and I have bonded over the last several years is that we’re both voracious readers. You’ve given me a ton of books. We talk about books all the time.

The last 3 people I’ve recorded with before you were Rick Rubin, Dana White, and Ed Catmull, the founder of Pixar. I was on the phone with you yesterday, and what I realized is that all 4 of you have in common, even though you work in vastly different industries and in different ways, is that you’re essentially taking a lot of time to know yourself. Then, once you did that, you’re just building your business for you first.

100%. Naval, who is a friend of mine and of Jared’s, always says, “Escape competition through authenticity.” If you’re competing, it’s because you’re copying. Build something that fully comes from you, and that will feel most right. It’s also the thing that’s least replicable.

I love the idea of escaping competition through authenticity, but you have to do the hard work of knowing who you are. You can’t be authentically somebody else, right?

I think part of the reason I like to read so much is that we all wrestle with the same series of hard questions that all of humanity has wrestled with, right?

For thousands of years.

And there aren’t that many of them. Humanity—all of who we are—just echoes over time with these same questions.

I love to look at books, and the reading I like to do tends to be things that take on those hard questions. What are the things worth sacrificing for? What are the gems of wisdom and insight that can be extracted from some of the most brilliant minds across so many fields?

I love philosophy because philosophers grapple with some of these tougher questions. From each of these amazing thinkers, if I extract a few pieces of wisdom, that’s just a gem I put on the chain with everything else. To me, that’s very, very interesting.

Then I think if you look in business, you have some of these people—and obviously, your life’s work is trying to understand them and know them, whether they’re living or dead—but you have somebody who will distill sometimes 80 years of a life into a 300-page book that you can buy for $30. They’ll tell you everything they’ve learned, everything they’ve experienced.

I think there’s just so much value in opening that book and listening to them.

It’s silly not to. I really do think it’s irresponsible not to. You’re close to some of the Walton family members.

Yeah.

And I was just with one of Sam Walton’s grandsons at an event yesterday.

Who’s that?

Steuart.

Oh, yeah.

Yeah.

I know Steuart.

Yeah.

He’s great.

Yeah. We were talking about that because there’s actually some writing from the co-author Sam had on his autobiography. Steuart listens to my other podcast, Founders, and he’s like, “I’m going to try to get this to you. I just can’t use it for public consumption, but just because I know you’re really obsessed with Sam Walton and admire him greatly.”

Yeah.

He’s like, “This will round out some things that you didn’t know about him,” which I thought was—

And that’s one of the best business books ever. Talk about a person who had a vision and just meticulously executed it over time.

But it’s also an act of service, because what’s so remarkable about that book is that he was writing it when he knew he was dying.

Yeah.

He was in a great deal of pain. Cancer was all over his body. He had limited time left on this earth, and what did he do? He said, “Hey, I had a 60-year experience as an entrepreneur. I learned some stuff. I’m going to put it into this book and then push it down the generations.”

Then people like Jeff Bezos happened to pick up the book and use some of those ideas to build Amazon, which made your life better and my life better.

This act of service cannot be overstated. It’s just super important. It’s so important that they do this.

I just saw Gwynne Shotwell yesterday, and I was like, “Listen, I know you don’t know me, but I know you. I’ve read every single book on the history of SpaceX. I’ve read every single biography of Elon.” I was like, “Will you please write a book?”

Mm.

And she’s like, “It’s funny you bring that up,” because she’s had an offer for 10 years. I was like, “First, you have such a unique lived experience working on one of the most important companies in the world. And don’t do it right now. Wait after they appeal, but you should write a memoir detailing your experiences, because it’s not just for her and her family. It’s for everybody else that comes after her.”

It’s a really hard thing to do. I mean, it’s like an X-ray of the soul. What do I reveal?

Great books—if you’re not exposing vulnerability, if you’re not really telling the truth—they’re not great books. So you have to be comfortable revealing yourself, the good and the bad. Obviously, you see it in books.

Yeah.

There’s a little revisionist history and—

Yeah.

—a little shaping and smoothing of the edges. But if it’s really going to be great—

Actually, Shoe Dog is a great one, another amazing book by Phil Knight.

You just read my mind.

Then you’re really putting it out there and leaving it out there.

And I know some incredibly successful people who have built enormous businesses, and then at 80 or 85, they write a book and are petrified for the launch of that book.

More nervous than when acquiring a major company?

Yeah, because there’s something so vulnerable about doing it. Plus, it takes a tremendous amount of discipline to distill the wisdom accumulated in a life into an understandable, relatable way and really pull out the principles. You ask a great musician how they do it. Sometimes great musicians can’t teach you to play the guitar, right?

Yeah.

It’s like they don’t know. They just do it.

Yeah.

So I think for a lot of people, it’s an interesting exercise, even at a late stage in their journey, to discover why what they’ve done has been so effective. What are the patterns over time? Some people recognize it while they’re in it. For other people, it’s just second nature.

I’m obsessed, as you know, with people who do things for a long period of time. Everybody thinks I have a fetish for old people. It’s not that I have a fetish for old people. It’s just that if I sit down with a 70-year-old entrepreneur who’s been building his business for 50 years, there’s stuff that, exactly as you said, he can’t explain. It comes out in conversations, and you kind of piece it together.

You read my mind with “Shoe Dog” because I just finished reading it for the 3rd or 4th time.

Yeah.

And I just recorded another episode on it. It’ll be out soon.

That’s one of the great opening lines. What’s the opening line? It was something about the pioneers: “And then there was us.” Some made it, some died along the way, and then the rest.

Yeah. So he’s in Oregon in the 1960s, and he thought people from Oregon didn’t think big, so no one around him did. In fact, everybody around him, including his father, was saying, “Don’t do this weird, crazy idea that you have.”

But he says his track coach and teacher—the same person—and his co-founder of Nike, Bill Bowerman—

Mm-hmm.

—took great pride in the fact that they were from Oregon because of the Oregon Trail.

Mm.

And they said, “The cowards never started. The weak died along the way.”

“And that leaves us.”

“That leaves us.”

I love it. Yes.

And he believed it.

I remember. It’s been years, probably decades, since I read that book, but I remember that opening. I thought, “What a great entry.”

The opening of the book is perfect because we were just talking about this. When you were 22, when I was in my early 20s, the existential angst of a young man or woman in their 20s is universal.

Yeah.

It’s like, “What is my life going to be?” So much of everything is ahead of you. He’s on this run, and he feels like he’s been away from his house for 7 years. He has an MBA, he served in the Army, and he’s living in his childhood bedroom. He’s thinking, “What am I doing with my life? I’m a grown man. I feel like a kid.”

Yeah.

In the opening, where he’s running, he’s thinking, “I’m going to pursue this crazy idea,” which turns into Nike.

Yeah.

But it ties to what you just said. In the book, he talks about getting his heart broken. He talks about the death of his son and the fact that he was a bad husband in the beginning, that he was absent-minded. The book ends way before the peak, way before the peak.

It ends at the IPO.

Yeah, at the IPO. He’s almost saying, “Okay, you know what happens next, but this is how many decades—”

The struggle.

—the struggle to get there.

One of my favorite books that I recently reread—and it’s interesting, because I’m at a point now where I’m reading a lot of new things, but I’m spending a lot more time revisiting things that had a profound impact on me. The act of rereading something at a different point in your life means you experience it in a totally different way.

As with everything else, including some of the things you’re asking me about what I’m working on, for me, it’s less and better: fewer things, more focus, more intentionality. The same is true of books, and it’s been so beautiful at this point in my life to reread some of these great books. One of my favorites is “Man’s Search for Meaning.”

Mm.

By Viktor Frankl. I was thinking about it when you were talking about hardship and struggle. He certainly does not romanticize struggle. He endured the most difficult of human experiences, and Viktor Frankl tells his story of surviving the Nazi concentration camps.

But the idea is that meaning can often be redeemed by struggle. You don’t find meaning when things are easy; you find meaning when things are difficult. When things are extremely difficult, it’s often that same meaning that helps you endure, and there’s something so incredible about that.

I’ve been talking to my children a lot about this book. I just gave it to my daughter, who’s as voracious a reader as I am.

Mm.

It’s amazing. I love it. She blows me away.

That’s a gift.

She goes to the bookstore probably once a week to pick up something new, and she’ll come back. She just came back with “War and Peace” under her arm.

Oh, my God.

The book is like this—it’s like a doorstop.

We should say she’s 14.

She’s 14. She’s amazing. She has a tremendous curiosity and thirst to learn, and she also loves reading.

We were talking about this book recently. I had just given her “Man’s Search for Meaning,” and this idea is so empowering: everything can be taken from you. The people in the concentration camps, and Viktor Frankl himself, really felt like everything had been stripped from them—their families, everything.

And yet there is a sliver of sovereignty in how you experience that, how you react to that, and your ability to show up—your attitude in the face of enormous struggle and challenge.

Mm.

I think that’s so empowering because that’s such an extreme example. But he has this beautiful quote. I just emailed it to her, and this will be a paraphrase: “Between stimulus and response, there’s a space. In that space lies the freedom to respond and react, and in that reaction is your freedom and growth.”

It’s about finding that space between stimulus and response. He encapsulates the idea of our ability to show up in great times and—

Mm.

—also in the hardest of times, and the ability to really control our own mindset, which is extremely powerful.

What was the most difficult period of your life professionally, when you were going through the most struggle, pain, or indecision?

I think probably when I made the choice to go into government. It was incredibly challenging because I hadn’t been planning to, and I was finally at that place where things were like a hockey stick.

You had a thriving business.

Things were going so well.

Yeah.

I feel like you spend your 20s really setting the foundation, and then it was going so well. My fashion brand was doing over 800 million in sales annually. I was running all of the real estate acquisitions and development for the Trump Organization, so I was building the Old Post Office at the same time as I was building Trump Doral, which is 800 acres here in Miami.

I had 3 young children, very young in 1 case. My son, Theo, was literally on my hip.

Mm-hmm.

He was 6 months old. And then my father won the presidency, and he said, “I need you.” He’d never spent a night in Washington until his first night in the White House, and he didn’t know anyone.

Yeah.

I mean, we lived in New York City. Half the politicians we knew were Democrats who would come annually to fundraise and introduce themselves. So he really knew no one. He was going to a new city, and he trusted my ability and Jared’s ability. He trusted our judgment, our instincts, and our intentions—the fact that we would be honest and truthful with him—and he asked us to go.

This was around a week and a half after he had won. It was a complete change in the trajectory of our whole lives.

It’s like a 180.

There was nothing. Normally, when people run for office, they set themselves up for it. They contemplate it for 20 years, and they take on smaller challenges, like state and local races.

My father started with the presidency, won the presidency, and then said, “Hey, I need you.” I think both Jared and I, in that moment, looked at each other and said, “We can stick our heads in the sand and continue on as we had planned, developing our own lives and businesses.”

But would the 80-year-old version of ourselves look back and be proud of that choice—proud of the decision not to go in? I think we both knew he was asking us for help. He was giving us an enormous opportunity to give back to a country we love so much. Even if it was decades ahead of schedule, we should be so honored to do it.

You know, I’m pretty intense, and I was on a path, and that path was bearing unbelievable fruit. I felt I had those reps, and doing things and achieving things was just easier than it had been when I was 22. I completely changed the trajectory of my life.

That was an adjustment, but an unbelievable period of growth for me. I think another period of growth for me was actually when I left government and you hand back the keys. You don’t have a foot in the door and a foot out the door. You go through the transition, hand back the keys, and you’re done.

But now we’re in a new city. We had left our old lives, and suddenly I’m at this point in my life where I have a lot of lived experience—a crazy amount of lived experience, when you think about it, in the private sector and in government service—but the slate is completely clean for me. That was an experience that was both frightening, because I wasn’t used to it, and incredibly exciting.

I’ve recently looked back to when I was a little kid. I saw a video somewhere that somebody had sent me, and it was me at 17, looking out over the New York City skyline and talking about how I was going to impact this unbelievably iconic cityscape. There was no humility about it.

Yeah.

It was just the confidence that you can only have when you’re 17.

Yeah.

It’s like before you actually start working and realize, “Hey, this is pretty hard.” But I just knew, and I was so sure my whole life that I would be a builder, that I would build incredible projects—towers, hotels, resorts—and alongside these great masters. I was so, so confident in that.

I always knew what I wanted to do, and then it took me different ways. I also started my fashion brand, and I had a bunch of tech ventures. So it took me in a lot of unexpected places, but I felt like I had a clear path.

When you leave, everything’s all of a sudden wiped clean. You have to talk about knowing yourself. The best thing I did was not just reconnect old wires and do the things I’d done before, because that’s what I knew.

I actually made the choice not to go back to our family business and not to restart my fashion brand, because I wanted a new adventure and a new experience, and I was a different person. I had been so expanded by those years.

That was frightening and incredibly exciting: to really say, “Okay, well, now I’m building for the next portion of my life. What did I enjoy? What was I great at? What did I feel uniquely capable of? But really, what do I love, and how do I want to spend my time?”

That’s where I’ve been ever since, really, setting an incredibly high bar for the places I’ll commit my energy and time. Also, because now the opportunity cost is so real. I have 3 kids who need me very much: a 14-year-old daughter who I mentioned, a 12-year-old son, and a 10-year-old son. They all need me in different ways.

And it’s going to go by like that.

Yeah. I mean, with my 14-year-old, in 4 years she’ll be out of the house.

4 years.

I think about what she needs from me right now. She’s obviously at that age as a teenage girl where me being home with her upstairs and the door closed is as important as when she was a baby and I was rocking her to sleep every night.

Yeah.

It’s just being here, watching, listening, and being available.

Yeah.

A friend of mine said to me recently, “When teenage girls start talking, drop everything you’re doing. It doesn’t matter what you’re doing. Drop everything you’re doing and listen,” because they don’t talk that often.

Mm-hmm.

They talk a little bit less as they get older.

Yeah.

That’s what I want to make sure I’m here to do. When she feels like telling me what’s on her mind, when she feels like talking, I have the capacity to really listen.

I think the me right now that’s taking on different challenges—they’re no less ambitious—but I think the professional part of myself, that drive, that hunger, that ambition, is much more fully integrated into me as a human being than it was when I was 20.

Was it all work when you were 20?

I really identified with achievement and success, and I got a lot of motivation from having these wins. So I wouldn’t necessarily say that, because I was always very family-oriented. I got married pretty young and started having children relatively young. I really had a lot of working-woman energy.

Yeah.

Now, that energy—I’m still as driven, but I feel like I’m much more aligned within myself. The need to achieve does not drive me in any meaningful way. Everything I’m doing is because it’s something like a soul project, something that I’m deeply inspired by.

Mission-driven, something that gives you energy, something that you can put your soul into.

For sure. Alan Watts says—and I think about this all the time, because I’m always thinking about how to grow and how to become a better version of myself—that “you are under no obligation to be who you were 2 minutes ago.”

Yeah.

I think about that in the context that if you’re not a little bit embarrassed about who you were 5 years ago, you’re not growing enough. I look back at me 10 years ago and think, “Oh, that’s cringe.” But there was nothing wrong. I was just in that developmental stage.

I hope that in 10 years I look back and view the me sitting and talking to you as not evolved to the place that I am at that point in time. Maybe that’s why also interviewing the 80-year-old, as you were saying. They’ve been through it, and hopefully, they’ve emerged—

They’re just further down their edge—

—with perspective and context.

Yeah.

There’s just a lot of wisdom that you accumulate over 6 or 7 decades of surviving, and in many cases, they were successful.

Some accumulate. There’s some wisdom. But the people who have that—

Yeah.

Boy, can you learn a lot from them.

You know, I think my grandmother—she lives with me. She’s 99, and she’s amazing. She’s very different. She has no business interest, but she is—

This is your mom’s mom, correct?

My mom’s mom.

Okay.

But she’s one of the wisest people I know, and she really taught me about love and the truly nurturing kind of devotion to another human being. So I learned so much from her.

I learn so much from my children. I view everyone, including the people who anger me—maybe especially the people who anger me—as teachers. If somebody triggers a reactive response within me, I actually take the time to think about what it is about that person that provoked this in me, so that it’s an opportunity for me to learn.

I look at my kids, and I learn so much from them because they’re so present in the moment. They’re like Rick. They’re so comfortable with who they are.

You see a child, and there’s an amazing phase where they’re verbal, but the outside world hasn’t yet conditioned them to be anything other than themselves.

Yeah.

Right? Including parents.

Yeah.

There’s this magic age where they’re 6 and 7, and then at 8, 9, and 10, you start to see that they’re embarrassed if you give them a kiss in front of their school friends. They start responding to the feedback that they’re receiving that’s external to themselves.

But it’s magic. With all human beings, I think in adults you see it less, like when they’re in their flow and they’re really in their moment. You see it with great musicians when they’re up on stage and you see that they’re lost in their craft, and they’re just in it.

Mm.

But I think with kids, you see it most clearly. I watch—I mean, with my daughter, it’s when she’s around animals, specifically horses. When she’s out on her horse, she is so complete in herself.

Mm-hmm.

With my son Joseph, it’s when he’s in nature. He’s out on the ocean, and he just loses himself. I see him staring at it. It’s beautiful, and it’s something that I learn from.

I actually feel myself decompressing. I’ll put down my phone, stop trying to take a picture of him experiencing this, and be in it with him.

Yeah.

And then my youngest son, Theo, it’s when he’s playing games—any kind of game. I think it’s because he’s the third. He likes the undivided attention.

Chess, poker, backgammon, dominoes—you name it, we play.

Mm-hmm.

That’s why we have 3 different game tables around the house.

Yeah.

It’s a beautiful thing to see.

Go back to this period of reflection. Now it’s almost like you had a second birth, like a rebirth.

Mm.

You have an opportunity as a grown adult, a mother, and a very successful person. Now I get to choose. Everything in my past is gone, and I have a blank sheet of paper—

Yeah.

—to work from, right? How long was that time period until you figured out what your next move was going to be?

Probably the smartest thing I did was not just gravitate toward the playbook I knew. I actually wanted to really sit with it. So I took around 6 months where I was extremely proactive in saying “no” to old partners. People had ideas.

Mm-hmm.

I really wanted to just be in the moment. I wanted to create and build a new life for my family here in Miami, which meant developing new routines and new habits, finding after-school activities that interested them, really connecting with them, and connecting with our new environment.

That was one of the greatest things I did, because it allowed me to set up my life here really intentionally and build something—a reality that I love living every single day.

My brother-in-law always says, “The happiest people are happy to go to work, and they’re happy to come home from work.”

Oh, Josh?

Yeah.

I’ve seen this.

I think that’s 100% right. You’re as happy as your least happy child, so making sure my family was set up. Then I think I started to become curious.

Part of my process is to read and study. Part of the reason I love investing—

Yeah, I was going to go here next.

—I have an insane curiosity for what’s out there: what could be, what is, what people are doing, and what people are building. I love being surrounded by, first and foremost, kind, good, driven people, but also people with huge ambitions and wild imaginations who see what the world can be and have their finger on the pulse of that.

I think spending time in a lot of different ecosystems that wouldn’t necessarily have been natural to me, coming out of a real estate and fashion background, allowed me to really immerse myself in technology, robotics, biotech, and even health tech. There are some amazing things happening now where we can really leverage information to catalyze changes in our own behavior. You see all the wearables, like WHOOP and other companies like that.

I really wanted to spend a lot of time with these people, learning from them and helping accelerate the businesses that I most believed in, and that put me on a beautiful path. In some cases, that took me back to the beginning, like in the case with Sazan and what we’re building there. I sort of came full circle, and that project will ultimately be the culmination of all of my prior experience in real estate and with travel.

Yeah. This is one thing that I would love for you to explain your thinking on. When you shut down your business—

Yeah.

—you went into government. You resigned from 350 things.

Yeah.

Now you have this—

You literally sit with the Office of Government Ethics, and they review your whole life and tell you if anything could potentially be a conflict of interest. You either have to divest of it or put it into a trust. They go through everything, determine it, and tell you what to do. Then you go back, show them that you’ve done it, and they have to stamp it.

Yeah.

It was a wild untethering from the life you were building, in super-small ways and then much larger ones—selling businesses and selling assets, in some cases buildings. It was a very unique experience, but then you’re really in it and free of everything you had been doing in the past.

But I can’t help but think that in this new reset, this new rebuilding of your life post-White House down in Miami, you wouldn’t even be involved in 350 things today. Am I wrong about that? Because I feel, in the conversations we have—

Yeah.

—you have these recurring themes. It’s like fewer, deeper; fewer, better.

For sure.

Can you explain the change in your decision-making there?

You think about moments in your life, and I think that moment was an inflection point for me in so many ways. I emerged as a very different person, but I think one of the things that also happened is that, at a time when I was really running and really happy with the trajectory my life was headed on, the treadmill stopped. I completely pivoted, and that afforded me the opportunity later to decide which races I was going to compete in and which I wasn’t.

Mm.

That’s something that doesn’t typically happen to somebody when they’re in their early 30s. That’s when you’re very tethered to the path that you’ve charted for yourself. So, in the end, I think it was a great blessing.

Do I think my life would have turned out great? Sure. But it did give me a lot of perspective, and it gave me the ability to really mark things in my mind and create a lot more simplicity for myself, and really only commit to building things that I would be passionate about over the long term. Some of the things I was working on were legacies of my early 20s, when I was just getting started.

I think part of what you should be doing when you’re young is throwing a bunch of stuff against the wall and seeing what fires you up. You have to have experience, and sometimes the best experiences are the horrible ones, because you know that’s not the right path for you. Some of the best bosses are the worst ones, because you learn from them how not to treat people, right? So, I think it’s all good.

The whole experience of detaching from everything that I had built up to that point and then, as a more fully formed adult, coming back and being super intentional was very clarifying. Jared loves the book Essentialism, and we talk about it all the time because, for him, simplicity is king. He loves distilling complex things, ideas, and systems into the simplest version.

I think you can find a lot of peace in your life when you’re able to do that, and it’s hard. It’s a very hard thing. There’s the famous line, “I wrote a long letter because I didn’t have time to write a short one.” I think about that. It’s much harder to write something precise and drill down on why it’s so challenging to write a book, because you’re distilling complicated ideas and a complicated life story into 300 pages with clear takeaways.

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Jared keeps hounding me to do an episode of Founders on the book Essentialism.

Yeah.

The more I talk to him about it, the more I think it’s related to why he’s so good at doing deals, because he’s searching for the most important thing, the essential thing.

Yep.

Once you identify that, I got to have lunch with Sam Zell before he died.

Yeah.

Our mutual friend Rick Gerson was the one who set up that lunch, and one thing that I talked to Rick about is that he was mentored by Sam for 25 years.

Mm.

He was like, “I didn’t know anything. I was in my early 20s when I met him, and I’d bring him a deal. I’d be like, ‘You know, there are 10 things we have to take care of.’” Sam Zell would look at it and say, “There’s 1.”

Yeah.

“If we take care of point number 5, then everything else will work itself out.” I asked Sam about that, and he said, “I learned that from Jay Pritzker,” whom some people considered the best deal guy of all time. He said, “I used to bring him deals when I was in my early 20s. This whole thing is replaying, and I’m like, ‘Look at all these things we have to do,’ and Jay’s like, ‘No, you only have to do 1. You have 1 problem here to solve, and the rest—’”

The best leaders and the best entrepreneurs can see clearly. They can find the signal in the noise. I think about it almost like the golden thread: there’s 1 thread you can pull, and the sweater unravels. Or you can do 1,000 different things.

Really honing in on the variables that matter most isn’t just true of business; it’s true in life. What are the times that really matter, when you need to be there for your kids? Are you showing up in those moments for your spouse and your friends? I think being able to see clearly is everything.

You think about these great founders, and they’re solving meaningful problems, oftentimes simply. They’re removing a lot of friction from people’s lived experiences with products or services. Then they’re distributing it aggressively. It’s not just the idea; the idea is becoming known and being distributed to the consumer. Then they’re enduring the hardships that will inevitably come as they build a big, meaningful business.

The ability to do that over time, with the same level of commitment, stamina, and passion—that’s fundamentally what entrepreneurship is.

I’m kind of obsessed now about this idea of the reset that you got to have, because it happened after probably a great deal of pain—

Mm.

—I would imagine.

Not pain, just challenge, right? Intensity and growth. These were amazing life lessons. We went to D.C. completely green, including my father. We put a lot of lead on the board, and we left that experience really proud of what we had accomplished. But we were drinking water through a fire hose. We were learning everything in real time.

What we could get done in the 3rd year versus the 1st, or the 4th year versus the 2nd, was a different game.

What was the feeling when it ended? Relief?

For me, this had not been my life plan.

Yeah.

But I think I responded in a way that I’m proud of to the moment. Now I look at a lot of people—they call it Potomac fever. Once you’re close to that level of action and power, you even see it with business leaders: they just gravitate toward it.

Mm-hmm.

It’s very hard, and you see them; they hang around the hoop. They go into the private sector for around 2 weeks until they cycle back in at a slightly higher position.

For me, it was always about being asked to serve, being honored by that request, and feeling a great privilege in being able to do it. I feel really good about the body of work we were able to accomplish.

I personally was entrusted to work on issues like workforce development, vocational education, and apprenticeship expansion—all things that are incredibly and increasingly meaningful in light of the disruptions that are coming with AI. Doubling the child tax credit meant that 40 million Americans benefited—on average, $2,500 a family—from the expansion of the child tax credit. That is incredibly meaningful work.

Paid family leave—the first-ever national plan—gave federal employees access to paid leave for the first time. On human trafficking, there were 9 pieces of legislation I championed that were passed into law to combat child exploitation and human trafficking. Environmental stewardship with the Great American Outdoors Act, which was the largest piece of environmental legislation passed since the creation of the national parks by Teddy Roosevelt.

By Teddy Roosevelt.

So, it was this unbelievable piece of legislation to help protect and be good stewards of our incredible national park system, and on and on in areas that I found to be deeply important and meaningful.

But now, I’m in a new section of my life, and I know that, for me, the first time around, I could theoretically imagine it would be intense. I would know, sort of, the sacrifice my children would have to bear. I would imagine it. But now, I know how intense it is. I know that you can’t dabble, and I know that my children really need me there for them, and I’m not willing to make them bear the sacrifice of serving again.

I’m extraordinarily inspired by the ability to impact positive change in the private sector. So, most of the things I’m building, whether it’s a company like Planet Harvest, which I co-founded with my good friend Melissa Ackerman, are helping find use for the 40% of fruits and vegetables we grow in this country every single year that don’t even make it out of the field. They get plowed under because they don’t meet a cosmetic specification that relates to size and shape.

So, perfectly nutritious food that we literally plow into the ground—that’s zero revenue for the farmer after they’ve spent all the money to bring it to the point where it’s about to be picked; that’s not going into communities that need this healthy and nutritious produce, and that has tons of environmental externalities associated with that amount of waste.

So, how do you take something that was a waste product and turn it into an asset or something that’s actually usable? How does Planet Harvest do that?

It had been done that way because it had always been done that way. There was no secondary market for any fruit or vegetable that didn’t meet an exact specification in terms of size and color, even though sometimes the taste and the quality were in no way compromised. So, there was just no market for it.

We said, “Well, that makes no sense at all. Let’s stimulate the demand side and create demand so that we could support these small and medium-sized farmers.” This goes back to just listening. I started listening during the COVID pandemic to the challenges of small and medium-sized farmers, and that was an extreme situation because the supply chain just completely shut down, right?

So, if you had a farm and you had a perishable product like a strawberry, suddenly all the restaurants were closed. Unless you had an account with Walmart, you had nowhere to sell your produce, and so you tilled it into the ground. As part of COVID and as part of the CARES Act, I created something called the Farmers to Families Food Box Program, where we created grants to buy this great product and surge it into communities in need, keeping these small and medium-sized farms alive and thriving during this incredibly difficult time, saving the jobs of the distributors who would transport between communities and the farms, and obviously feeding a lot of people who were in need.

At that time, I started looking at the business more generally and realizing: Why isn’t there a secondary market? Why aren’t these great strawberries going to a juicer if they can’t be displayed in the fresh aisle at Walmart because they don’t meet the very exact cosmetic specification? Everything is so uniform in size. It’s very different in other areas of the world. In Europe, it’s organic.

Yeah.

Things are slightly bigger or smaller. So, my partner and I sought to stimulate demand by working with large consumers, sharing with them the issue, and getting meaningful offtake for these small and medium-sized farmers.

So, companies like Chobani—now, all of the fruit that we find in their beautiful yogurt products and smoothies—

Oh, yeah, because—

—is all sourced by Planet Harvest—

You can just mix it in.

—from small and medium-sized farmers. That would’ve been 100% waste. It would’ve been tilled under.

So, it’s an amazing thing that in America, we don’t have a lack of produce being grown. We have an enormous amount of produce being wasted: 400 million pounds of strawberries alone—

Oh, geez.

—that’s being tilled into the earth as opposed to going into yogurt or ice cream.

Why do they put it back into the earth?

Because they can’t even afford to give it away. That would mean somebody would have to pick it, and they would have to package it—

Okay.

—and then they would have to ship it.

Okay.

So, there’s no incentive to do anything other than to look at its size and then throw it into a ditch, which also means more fertilizer. Oftentimes, the crops have to be sprayed more because the flies will be attracted to the waste that’s left in the field.

My partner today is with Fresh Express in Salinas, California, and it looks like, after you go after a lettuce harvest, you look at the field and it looks like the field is full of lettuce. But how little of what’s being grown is actually being taken and served to communities, and how much of it is being wasted, is horrific.

Once you start to educate people on the problem, they want to be part of the solution. So, we’re now partners with Chiquita Banana. We’re partners with Chobani. We’re working with large-scale restaurants and grocers, and everyone who wants to be part of the solution: How do we get this into premade food, into food service, into grocery stores, in a way that’s sustainable and super beneficial for these farmers who have a very tough job to begin with?

The incremental revenue to them is deeply meaningful. Oftentimes, it’s the difference between a third-generation farm becoming a fourth-generation farm or not. So, that’s work I’m really passionate about. Jared says something that I think about all the time: He loves being contrarian by being obvious.

This is such an obvious waste, and there should be a market for this beautiful produce, and yet it’s being discarded. So, I love solving problems that are obvious. I love talking with people like Hamdi from Chobani and saying, “Did you know this was happening? Forty percent of produce grown in America doesn’t leave the field.” And him saying, “How can I help?”

So, that’s a really mission-driven business that I’m deeply passionate about, but I think will scale in a very, very meaningful way while doing a lot of good.

On the other side, I’m working on incubating a bunch of nonprofits. Something that I’m really excited about came from a conversation I had with a great friend, the technology investor who you know, Elad Gil. This was years ago, and we were talking about some of the positive use cases for AI. What is the light in the Force, if you will, that isn’t being executed upon currently?

We started talking about how so much of history’s great works of information and literature are not accessible to so many people around the globe due to a lack of access. Maybe they don’t have a library in close proximity. Maybe they can’t afford to buy a $30 book from Simon & Schuster on the Stoics and/or Marcus Aurelius’s “Meditations.” Maybe they live in a country where there’s no translation for that work in their native tongue.

So, we started thinking about how AI—specifically now that generative AI has gotten so good—could create high-fidelity translations of these incredible literary works that are in the public domain anyway. So, you think about Dostoevsky. You think about the Brontës. You think about Marcus Aurelius or Epictetus. All of these works are available in the public domain.

How can we use AI to translate them into all the world’s commonly spoken languages and make them accessible for free to everyone, either in text form or as an audiobook? So, we’re working with a lot of the large language model labs to do exactly that: to do the translations in a really great, high-fidelity way in most of the world’s spoken languages, to make them accessible for free to everyone who has internet access, and to also have audio translations.

You can actually query the text and ask questions as you read along. There’s no reason that a high school student in Philadelphia who can’t afford to buy “Jane Eyre” for their eighth-grade class shouldn’t be able to have access to it in a beautiful, accessible way. And some of the stuff you can find online, but it’s not for consumption, right?

No, I go to these websites. Obviously, I’m obsessed. I read more than almost anybody else, so I go to these websites too, and the format’s terrible.

They’ll scan pages of a book in and upload it into the universe. But this is a product that’s meant for a consumer. We haven’t launched yet, but we’re about to launch with the first 1,000 works, and we’re going to learn a lot. People will give us feedback on each of the translations.

But imagine now “Meditations” will be translated into most of the world’s spoken languages. We’re covering 95% of all languages spoken, and it will be available for free if you have internet access.

So, we're democratizing access to this incredible knowledge. We're calling it Alexandria. But that's just a really fun project, and that came out of a conversation that I had with Elad, where I'm like, “What are you most excited about that's not being done?”

He told me, “There are so many unbelievable works by the greatest thinkers humanity's ever produced that just still aren't accessible, and that doesn't need to be true.” So, I've been helping him realize this dream of making it available.

Yeah, anything I can do to help on that project. Obviously, it's close to my heart. I would definitely volunteer if you need any help. I've been using AI for the last few years to translate books that are not in English to make episodes of Founders on them.

Mm.

The translations are getting so much better, so I think you guys are perfectly timed.

Yeah.

Because I was doing this a few years ago, and I remember I translated one—I think it was from German. I remember the one line was supposed to be, “This happened 15 years ago,” and the translation was so bad, it was, “This happened three five-year periods ago.”

Yeah.

That's a funny way to say 15.

Five years ago, we couldn't have done this well.

Yeah.

But now, the large language models are so good, and generative AI is really allowing us to do it affordably—

And the voices.

—to do it with high fidelity. The voices are amazing. So, ElevenLabs is helping—

I was going to say—

Yeah.

Have you spent time with Mati?

I have, yeah.

Okay.

He's amazing.

Yeah.

So, he's helping us with the audiobooks—

Oh, perfect.

—that will accompany each of these.

Yeah.

But it's amazing, and we are working deep into some obscure languages where people really don't have access. They have internet. They won't have a library. They probably won't have a bookstore. Rural communities, but also students.

Right now, if you want to read Plato's Republic, you go and pay a publisher $35 for something that's in the public domain, that every 6 months they generate a new copy of and slap on a new piece of artwork on the cover. Students go and pay for it.

So, this, to me, is just a fun way to give back, to share some of the books that have so profoundly influenced me, but also to create a holding place for some of this really important information produced by humanity.

And these are huge forms of leverage for future generations. There's going to be all these positive things that come out of this that you and Elad could not possibly predict.

We're having fun. It's really hard to choose 1,000 books. People will say, “Well, you missed this and you missed that.” Of course we did. Even just the exercise of asking, “What are the most meaningful books for us? What should we translate next? How big is the scale of the project?”

The answer to that question is, as big as you want it to be.

Exactly.

There's no limit. It's not a physical library or a physical space that restrains you to 1,000, 2,000, or even 10,000 books.

But what I was saying is, the reason I think these kinds of things are very important—and I also think podcasting plays a role in this, too—is that I'm reading Kelly Johnson, who's the most famous and most successful aircraft designer in history. In his autobiography, he says one of the most important things that ever happened to him was that Andrew Carnegie had the biggest impact on his life.

He never met Andrew Carnegie, because Kelly Johnson grew up in exactly what you're describing: a very poor, rural community. He doesn't have electricity, for God's sake. He doesn't have access to anything else. This was when Carnegie was building all these free libraries and putting them all over the United States in these tiny communities.

Kelly would just go there, and he would live in the library. He said, “I read every single thing about aviation. I read fiction. I read all of these things that impacted me, and I've used them in my career many decades in the future.” I think you're going to hear a ton of examples like that when you guys do this project as well.

How do we take this wealth of knowledge and make sure that kids all over the world, and adults, are able to have the same experience he did? To be able to learn from the amazing people who came before, even if you don't have direct mentors in your life who can expand your thinking and inspire you?

Do you know who didn't have a direct mentor?

Who?

Elon Musk. I remember watching an interview with him that Kevin Rose did back in 2012. Kevin was trying to figure it out. They're in Tesla's factory—that's where the interview is happening—and Kevin's saying, “What the hell? You come from South Africa, you go to Canada, then you go from Canada to the Bay Area. You didn't have any money. How did you learn business? Did you have mentors?”

Elon said something that changed my life, because then I started reading biographies. He goes, “No, I didn't have a lot of mentors. I looked for mentors in historical context. So, I thought biographies and autobiographies were helpful.”

I was like, “Huh, maybe I should start reading more autobiographies and biographies.” Turns out you can find mentors in historical context.

There are very few people I look at and say, “I deeply want to emulate every aspect of their life.”

Probably nobody.

Yeah. You know, Jared's pretty close.

For me, the reason I say that is because there are some people who I think are brilliant in business. They're true visionaries, and their private life is a wreck. So, are they still brilliant, or are they stupid? If you're that smart, how do you not figure out how to create a stable life for yourself that's good for the soul, good for the heart?

Thank goodness they're doing what they're doing. It's a great gift to humanity. But I wouldn't want to emulate that, because I want to raise my children.

Yeah, exactly.

And I think that work is more important than that work. You'll have people all across the spectrum, but there are very few people where I say, “Wow, in every aspect of their life, their priorities feel calibrated, and they're doing well.” Not flawless, because perfection is not possible, but they're doing well.

The reason I say Jared is that he's really—he can be going through the most intense experience, and the kids don't feel it. He's deeply present wherever he is and whatever he's doing. He's not always physically present, but he's always available emotionally, telephonically. He'll drop anything he's doing. He somehow has the ability to always be in the right place, regardless of what he's juggling.

That's true for his partners as well. He's a very long-term thinker, and he's outcome-oriented, so he's highly pragmatic and solution-oriented. But that doesn't mean he's transactional. He builds deep friendships, and you know this, actually.

Yeah.

You have one with him, and you've seen him with others that are truly built on trust. That's because he's more of a giver than a taker. Over time, that ends up benefiting him in all sorts of incredible ways, but that's ancillary. He doesn't come at it from a place of thinking well over the long term. That's just who he is.

He's very comfortable with himself. He's just very comfortable being exactly who he is and very nonperformative. So, I learn so much from him all the time.

Although, given the fact that I know he's going to listen to this, I'm going to have to pull back. Can we edit this whole section out? Because I'm going to have created a monster.

Well, but he talks—

But that's the thing: he won't. No, he really has almost no ego. It's to the point where I'm incredulous by it. I'll get upset about things for him, and he doesn't care. If somebody criticizes him and he doesn't know that person, it just doesn't affect him.

It doesn't mean that he won't say, “Okay, well, that's warranted,” and recalibrate. He cares about the opinions of those he loves.

Well, we don't have to edit it because, as you just said, I spend a lot of time with him too, and he talks about you the same way. It's legitimate when he doesn't think I'm going to go back and tell you or anything like that.

Yeah.

And we've had a lot of dinners talking about this.

By the way, key to life: marry the right person.

Yeah, for sure.

Marry someone who puts you up on a pedestal—

I don't think I've ever heard—

He sees me in a way that I aspire to see myself.

This is very rare, what you two have. This is actually really beautiful, what you just said about him, because I was sitting here thinking as you were speaking. Very few people would describe their spouse as almost perfect in their eyes, for lack of a better word. That's actually incredible.

There are 2 things that we mentioned that I want to come back to, that I think are super important and that I'm super curious about. You mentioned essentialism, and you mentioned opportunity cost.

You essentially have unlimited opportunities in front of you in terms of who you can spend time with and what you work on. How do you make this decision? Is this intuition? Is this just energy? Is this vibes?

When you're deciding, “Hey, I want to meet this founder. I may invest with them,” or, “I may want to partner with somebody on this project,” like Planet Harvest in the profit domain or a nonprofit like you did with Elad, how are you making this decision?

Well, I think first you have to be receptive to the inputs all around you. I joke with my partner, I'm like, “I'm a farmer.” Who would've thought, right? I'm investing in tech companies and helping build these amazing businesses that are so beyond what I would've ever imagined myself doing.

Even the scope, scale, and ambition of Sazan, this incredible project—we’ll have hotels and resorts and wellness, all of it. It’s almost daunting in its size. Community is at the heart of how people want to live, right? So I’m thinking a lot about how to create a great community for families and connection, because I think that’s the currency: getting somebody’s attention, keeping it, and creating an enabling environment for exactly that.

But anyway, for me, I always try to be receptive to conversations with others and to what sparks something in me, and then I go deep. My daughter will joke with me. I have 100 ideas a week, and I start to go into them, and she’s like, “Wait, you didn’t do that? I got all excited about it. What about this? What about that?” I’m like, “No, no, no, that’s my process.”

I explore a lot of things, and then I go deeper and deeper. I do a tremendous amount of reading, so with any challenge I’m about to take on, I become like a PhD in that subject.

Mm-hmm.

With the Sazan Project, I’m reading all the best Albanian writers, and I’m trying to understand the country through their eyes.

Oh, that’s smart.

Fiction, nonfiction, all of it. You immerse yourself in the lived experience of these great observers of the truth, and then you get closer to it, right? You can’t just impose yourself upon a country or culture. You have to understand it first to do it in a beautiful, delicate, and meaningful way.

But that’s the approach I take to everything. I listen to a lot of people. I try to surround myself with people who help facilitate growth in different areas. I ask them a lot of questions. I actually tell my kids—they laugh at me—in addition to what we were saying before about reading all the time and being interested in the world around you, that only boring people get bored.

Yeah.

There’s too much to learn. But I also tell them in this context all the time that you never learn anything while you’re talking. You only learn when you’re listening and when you’re observing. So I really try to surround myself with people who are going to open channels for me and help me grow.

Sometimes that’s in a very intimate way: people who are really in touch with themselves and who can help me be a better mother, a better wife, and a better human being. Other times, it’s great business leaders.

But how do you decide who to let in? What kind of person do they have to be?

First and foremost, a kind person. Life’s too short. There are a lot of successful assholes, but I’m just not interested. The worst thing in the world is when you partner with somebody who’s not a good person. There is no contract in the world that will protect you from a bad partner.

Yeah, that’s Buffett and Munger. They say it over and over again.

I would do a handshake with a good person over the most ironclad, white-shoe-law-firm-created contract any day of the week. So I’m just at a point in my life where I want to do good, important things. I want to be an additive force in the world. I want to be surrounded by kind, good people whom I admire and can learn from, and there are so many of them.

The choice will never be for me to partner with the opposite of that. So I try to find good people. I try to find people who can help me grow, whom I can learn from. Then I dive deep into the subject matter through reading and through podcasts. I listen to a ton of podcasts—yours being my favorite, obviously—

Thank you.

—on a variety of different people and subjects. Then you have to get going. A mistake a lot of people make is that they get so excited about the idea, they keep ruminating on the idea. They keep pitching the idea. They don’t get to the point of actually doing it.

You learn a lot just in the early phases of bringing something to market. That motion can completely reorient your business, right? Because you receive feedback around it. For example, with Planet Harvest, we were creating demand for something for which there was no demand. Even the farmers weren’t taking this produce out of the field because there was no market for it, so we had to create a market.

We had to speak with the consumers and find out what they would pay for it and what they would get from it. They’d get the story of the small farmers they were supporting. They would get a diversified supply chain in terms of what was going into their product. They’d get the same caliber of product. But we had to go and explain it to them, and then we had to hear from them what that was worth to them.

I think it’s really important to get that message out there. One of my favorite books is *The Fish Ate the Whale*, about Sam Zemurray, the Banana King.

I heard your episode on that.

Yeah, Sam Zemurray.

It’s brilliant.

I forgot the subtitle, but it’s a biography of Sam Zemurray.

We’re working with Chiquita Banana now, the largest banana company, and helping them think about their excess and utilizing it.

Which is fun.

He did something very similar. He started in bananas, obviously, and they were just throwing them away because they would rot in 2 days, and they couldn’t sell them in the next 2 days.

There’s a line in the book that I thought of when I hear you talk about Planet Harvest: he saw opportunity where others saw nothing.

Yeah.

I think just being perceptive of the world around you—there’s unlimited opportunity around us that people are just jumping, skipping over, or ignoring.

Yeah.

In your case, you said that they just did it this way because it’s the way it’s always been done. So if you go into a new situation with fresh eyes and ask, “Why? Why?” just keep asking why. You’ll eventually get to, “Well, that’s just how it’s always been done.”

100%.

That’s the best answer in the world, because that means it’s ready for disruption.

There’s innovation they can do there.

I think that’s what’s so cool about doing the early-stage investing that I’m doing. Obviously, Affinity does later-stage investing, but with some of the earlier-stage investments, it’s really about being a good listener.

You sit down with the founder, and they don’t have the track record. In some cases, they haven’t even begun to execute their business plan. They haven’t commercialized it. In some cases, they have; in some cases, they haven’t. Either way, they’re in the earliest innings of their company.

So you’re listening: What’s the idea, and what’s the jockey like? You’re trying to understand whether the person has what it takes to build this thing, this concept, this product. Will they be in it for the long run? Do they have the flexibility, the mentality, the perseverance, the grit, the vision, and the leadership skills—all of these traits that you have to have, or the humility to know you don’t have and to supplement by hiring the right people?

It’s an assessment of the human being sitting across from you, and also of the idea that hasn’t yet been proven. In some cases, the more audacious, the better, because I’m not interested in investing in boring things. I like investing in things that have the ability to be transformational.

These often tend to be big ideas and often tend to be unproven ideas. You have to be a good listener because you don’t have a lot of data to support what they’re doing yet. So I think especially in the venture space, you have to have a lot of humility, and you have to be very interested in people and ideas.

I think, given your personality, you’re perfectly suited to be a champion for these new but fragile ideas. The recurring theme in all these biographies that I’ve read—the 400-plus biographies of history’s greatest entrepreneurs—is that new ideas are so fragile. It’s so easy to kill an idea prematurely and not let it grow.

You just have to give it room and time to grow, just like a human being. I think Jeff Bezos uses the analogy of an acorn turning into an oak tree.

Yeah.

That doesn’t happen in a week. It doesn’t happen in a year. It’s going to be a multiyear process that we have to understand going into it.

You may end up at a place that’s very different from where you started. You mentioned Jeff—he was selling books, right?

Yeah.

So that’s where it becomes, “It’s the idea,” and then, “It’s the founder.” What will that idea morph into? Very rarely is it a straight path. Most often, it’s something completely beyond the original aspiration. Tobi—I heard him on your show.

Yeah.

There’s a certain sort of neurological flexibility—

Mm-hmm.

—that these founders have, where they can be so passionate about something yet pivot it into something else they’re equally passionate about. That becomes the ultimate manifestation of that original acorn.

I think your life, and what you’ve shared with us so far in this conversation, is the perfect example of that, because you’ve done that in your second act as well. I’m honored to call you a friend. Thank you very much, Ivanka, for taking the time. This was absolutely perfect.

Thank you.

I hope you enjoyed this episode. Please remember to subscribe wherever you're listening and leave a review, and make sure you listen to my other podcast, Founders. For almost a decade, I've obsessively read over 400 biographies of history's greatest entrepreneurs, searching for ideas that you can use in your work. Most of the guests you hear on this show first found me through Founders.