David Senra - Ivanka Trump on Building an Authentic Life

Episode Date: May 31, 2026

Ivanka Trump grew up on construction sites and in boardrooms, learning what it takes to be a builder. At just 22 years old, she started doing real estate for a Brooklyn developer. She notched small wins with construction crews and learned the trade.  Then came the launch of her own fashion brand — which reached over $800 million in annual sales — run simultaneously with the Trump Organization's real estate acquisitions. The centerpiece was the Old Post Office in Washington, D.C., a dilapidated 1890s building she personally shepherded into a thriving urban hotel.  In 2016, she went to Washington, D.C. to provide support to her father in his first term as President of the United States. During the four years in Washington, D.C., she helped in doubling the child tax credit for 40 million families, standing up the first national paid family leave plan for federal employees, passing nine pieces of legislation against human trafficking, and getting the Great American Outdoors Act signed — the largest environmental legislation since Teddy Roosevelt created the national parks. When it ended, she started over, and built again. She co-founded Planet Harvest, creating a market for the 40% of American fruits and vegetables discarded each year because they don't meet cosmetic specifications. She's building Sazan, a 1,400-hectare private island in the Mediterranean with five miles of beachfront. She's investing in founders at the frontier of AI, biotech, robotics, and space. And she's working with Elad Gil to create Alexandria AI, a project that will translate the world's great public-domain literature into every major language and give it away for free. She describes herself as mission-driven now, not achievement-driven. The difference, she says, took her decades to find. Show notes: https://www.davidsenra.com/episode/ivanka-trump Made possible by Ramp: ⁠https://ramp.com⁠ AppLovin: https://axon.ai/senra Deel: https://deel.com/senra Chapters (00:00:00) Knowing What Excites You (00:02:02) The Sazan Island Project (00:07:18) Knowing Who You Are (00:13:06) Creating Stillness (00:16:30) Finding Mentors In Books (00:17:04) Avoid Competition Through Authenticity (00:21:05) Reading As An X-Ray Of The Soul (00:21:29) Phil Knight's Shoe Dog (00:24:55) Meaning Redeemed By Hardship (00:29:39) The Call To Government (00:31:16) Handing Back The Keys (00:41:42) The Reset In Miami (00:46:25) Less And Better (00:50:13) Finding The One Thread (00:55:54) Turning Waste Into An Asset (01:03:38) Democratizing The World's Great Books (01:12:07) Marry The Right Person (01:12:47) Deciding What To Build (01:16:23) No Contract Protects A Bad Partner (01:19:08) Opportunity Where Others See Nothing (01:21:34) Backing Fragile New Ideas Learn more about your ad choices. Visit megaphone.fm/adchoices

Right now in your life today, what is the most exciting part of your work life? My work life specifically. I think I have got into 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 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. So 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. So whether it's incubating companies from for-profit to non-for-profit businesses, investing in companies and founders that are really right at the

edge of transformation, whether that be AI, biotech, neurotech, robotics, even space, really things that I think satisfy huge curiosity for me and enable me to learn and grow and expand and founders that 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, to be expanded by them is, I think, super interesting. And then I've also gotten back to my real estate routes, 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 It is. There's no power on this island. You're building everything from scratch.

Correct. It's an unbelievable, beautiful 1,400 hectare 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 islands. We went on a hike barefoot all the way up to the top and we were just captivated. And it stayed with us ever since. And 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 really the architecture has to be fully integrated into it, almost rise from it. You know, it's not even a business for me, despite the scale of it.

Not only the island, but we have five miles of beachfront directly across from the island, this beautiful peninsula with a lagoon on one side, the ocean on the other. beautiful white sand beaches. For me, this is, it feels more like a challenge than anything else. The culmination of all of my experience in real estate, all of my travel, a lot of reflection on how I want to live, how I think people increasingly are wanting to live, and trying to really build something that's a tangible manifestation of that. That requires, There's a lot of vision, the collaboration of some of the greatest masters that exist. So I was just there walking the land, really just trying to sort of be with it and experience it alongside some of the greatest living architects of our time, like true masters of their craft.

People with integrity so absolute, like there will be no compromise. And 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 or real estate, home 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 six people off camera that I fadger every gay.

That you drive absolutely crazy. But actually that's where you get to something. And part of it there's a push and pull. When you're working with an architect, you know, unless they're building a monument, right? It's 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.

So there's certain functional elements. Like, there's nothing uglier than a beautiful, non-functional space. Like, that's, to me, that's not a masterpiece because it wasn't fully thought through. So when you can combine something that is architecturally, incredibly meaningful and beautiful and intentional, with a highly functional space. And one of the things I love about real estate is, well, first, 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's years, sometimes a decade plus. It's 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. Like to build something

that you know lasts longer than your own lifetime. One of the things that I love so much, and 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 and lovingly restored it and made it useful in its modern life. It was effectively a dilapidated post office and now is a thriving urban hotel. So that was an amazing project that took a very long period of time

to bring to life and just, example, but I think the thing I love the most, not only seeing it because that's great and experiencing it and remember 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 in one of the ballrooms, their daughter's wedding. Some experience they had that was a milestone life moment that somebody chose to have that happen. in a space that I conceived alongside many other talented people. So 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. And that's what we're going to do with this project, Cézah. Yeah, how do I say it? Cézon. Cézon. Okay.

I want to go back to something you said, that's very interesting. It's one of my favorite things about you. He said, I know who I am. So you were very kind. I was chasing Dana White to get him on the show forever, and he wasn't responding. And I text you, and you're very kind. And like, you set that up immediately. But Dana has this thing, there's just like a simple genius to the way he operates his life, in my opinion, in his business. And the piece of advice that he would give to, like, young entrepreneurs is, like, if you know who you are, which is very difficult to do and it takes a long time, if you know who you are and what you want to do, it's like the rest of your life is easy. You just,

You already know who you are. You know what you want to do. You just wake up and you 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? So 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? So 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. And sometimes it's really about saying no and setting boundaries or changing course. When those decisions, regardless of how hard they are, align with your values, it always feels good. Like, 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, with those core values that

you hold. Those are the things that I think you always regret. Oftentimes people get there because they sort of forum shop decisions. They'll ask people about their life, what should I do, what should I do? And they almost make it like a process to make tough choices. And there's something very important about speaking to people who are knowledgeable

and getting perspective and feedback. But ultimately, like you can't outsource decision-making as it pertains to major decisions in your personal or professional life. You really have to like sit with it. actually, you know, Dana, I think, is a great example of somebody who he knows himself so well. He's so authentically who he is. Like, he would be wildly uncomfortable, like wearing a mask and performing is in some other role.

I think Rick Rubin, I think so many great people, Dolly Parton, I love her. She's like, is who she is, and she's always been the same, and she really owns it. And I think we're drawn as people, if you look at sort of pop up. culture, I think we're naturally drawn 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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That is ramp.com. How did you get to the point where, you know, you're 22 when you started your first company? Yeah. You didn't know yourself. Now, several years later, you do. How did you do this? Well, I think, you know, it's people will say trust your instinct, but I think instinct has to be developed. So my instinct when I was 22 is different from my instinct today because I think instinct is honed and refined over time.

I think first and foremost, you have to get started. So you have to try things. And those micro wins that felt. as big as the massive ones today. You start to develop reps and patterns and confidence, which is so important. It's really hard to, like, trust yourself or trust your gut if you're deeply insecure and you haven't developed a rhythm or you haven't had some successes. And this could be in entry-level beginning positions. You know, I started out in real estate working for a developer in Brooklyn developing shopping malls. But those little, like, wins I had with the construction

teams or, you know, times when I felt like I rose to the occasion, they 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 and text messages and emails and, like, the access the world has into like the private sanctuary of our homes and our lives just through the devices that we we carry with us. I think 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. You know, I wake up. I 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 two minutes late for the bus. We always get there on time.

But we leave two minutes later than we're supposed to. So we're currently in a moment where each of my three children like completely different breakfast, so I'm like basically a short-order chef. And I've tried to find like that one thing, that they will all eat unsuccessfully so far. It used to be easier.

I make breakfast, drop them off at the bus. They go to school quite early. So I normally have the ability right after drop off to sit by the ocean. I live here in Miami and meditate as the sun rises. And I'll pray. I'll reflect. I'll think I keep that beautiful moment in my day as sort of an anchor to both offer sort of thanks and gratitude to God and the universe, but also to reflect on what my priorities are for the day ahead.

And I found that to be incredibly important and grounding. I come back to the house. I work out. And I do all of that. And, you know, it's like an hour and a half time span, two hour time span. But to me, that routine in the morning sets me up for success through the course of the day in terms of less reactivity, more being my more proactive in terms of clear definition around what I want to accomplish that day. And then what everyone else wants me to learn about or accomplish will be secondary as long as I sort of create clarity for myself around my goal. So and then I have some version of that in the evening, a little more challenged because the kids are all home and every night is a different adventure. but really trying to sort of find stillness so I can sort of hear what the universe is telling me. Rick Rubin talks about this

in his book The Creative Act that the creator ultimately is just super attuned with what the universe is saying and that the deeper you listen, the more you hear. And part of listening is listening to oneself. And if you don't create space and time for that, then 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. But I think part of the reason that happens is because they don't have their cell phone in the shower. Like they literally, whether it's five 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 that were both voracious readers, you've given me a ton of books. We've talked about books all the time. The last three people I've recorded with before you, Rick Rubin, Dana White and Ed Catmill, founder of Pixar. And I was on the phone with you yesterday.

And what I realized that all four of you have in common, even though you work in vastly different industries and different ways, is you're essentially taking a lot of time to know yourself. And then once you did that, you're just building your... your business for you first? 100%. Noval, who is a friend of mine and of Jared's, he always says escape competition through authenticity. If you're competing, it's because you're copying.

You know, build something that fully comes from you and that will feel most right. And it's also the thing that's least replicable. I love the idea of just escaping competition through authenticity. But you have to do the hard work of knowing who. who you are. You can't be authentically somebody else, right? I think part of the reason I like to read so much is, you know, we all wrestle with the same series of hard questions that all of humanity has wrestled with. For thousands of years. And they're not that many of them. You know, there's humanity, like all of who we are, it just echoes over time with these same questions. So I love to look at books

and the reading I like to do tends to be things that take on those hard questions. You know, what are the things we're 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 they grapple with some of these tougher questions. And from each of these amazing thinkers, you know, if I extract a few pieces of wisdom, that's just like a gem I put on the chain with everything else. So, you know, to me that's very, very interesting. And then I think if you look at in business,

you have some of these people on. Obviously, your life's work is trying to understand them and know them, whether they be living or dead. But you will have somebody who will distill sometimes 80 years of a life into a 300-page book that you can buy for $30. And they'll tell you. 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 like irresponsible not to. You're close to some of the Walton family members. Yeah. And I was just with one Sam's grandson, Sam Walton's grandson at an event yesterday. Who's that? Stuart. Oh yeah. I know Stuart. Yeah. He's great. Yeah. And we were talking about that because there's actually some like, I don't even know if I should say this publicly, but. we'll see, there's some writing of the co-author that Sam had on his autobiography, because Stewart listens to my podcast founders, my other podcast founders, and he's like, I'm going to try to get this to you.

I can't use it for public consumption, but just because I'm really obsessed with Sam Walton, and I admire him greatly. And he's like, this is kind of like round out some things that you didn't know about him, which I thought. And that's one of the best business books ever. Like, talk about a person who had a vision and just meticulously. executed it over time. But it's also an active service because what's so remarkable about that book is he was writing

it when he knew he was dying. He was in great deal of pain. Cancer was all over his body. He knew he did not have, he had limited time left on his earth. And what do you do? He's like, 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.

And 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. Like this is such, this active. can not be, like, it's just super important. It's so important that they do this. I just saw Gwen 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. It's like, will you please write a book? And she's like, it's funny. You bring that up because she's had an offer for like 10 years. I was like, just like 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 the 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. Yeah. What do I reveal? I mean, great books, if you're not exposing vulnerability.

If you're not, like, really telling truth, they're not great books. So you have to be comfortable revealing yourself, the good and the bad. And obviously, there's, you see it in books. There's a little revisionist history and 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, like, amazing book. You just read by Mike. By Phil Knight. 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, 85, they write a book. And they are petrified for the launch of that book. Like, more nervous than in acquiring a baby. major company or something, you know, 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, really, like, pull out the principles. You ask a great musician how they do it.

Like, sometimes the great musicians can't teach you to play the guitar, right? It's like they don't know they just do it. So I think for a lot of people, it's like an interesting. interesting exercise in even at a late stage in their journey, kind of discovering like why what they've done has been so effective, what are the patterns over time. So some people recognize it while they're in it. Other people, it's just sort of like second nature. I'm obsessed, as you know, with people do things for a long period time. Everybody thinks I have a fetish for old people. It's not that I have a fetish for old people. It's just like,

if I sit down with a 70-year-old entrepreneur that's been building his business for 50 years, there's stuff that he, like exactly what you said, he can't explain it, but it comes out in conversations and you kind of piece it together. You read my mind with Shudaw because I just finished reading it for the third or fourth time. Yeah. And I just recorded another episode on it. It'll be out soon. That's one of like the great opening lines. What's the opening line? It was something about, you know, the pioneers. And then there was us. Like some died along some made it, some died along. And then there were, you know. So he's in Oregon in the 1960s. And he's like, you know, he thought people from Oregon, they didn't think big. So no one around

him. Everybody's, in fact, everybody around him, including his father, is saying, don't do this weird, crazy idea that you have. But he says his track coach, his teacher, the same person, and his co-founder of Nike, Bill Bowerman, took great pride in the fact that they were from Oregon because of the Oregon Trail. And they said that the cowards never started. The weak died along the way. And that leaves us. I love it.

And he believed. I remember it's been years. It's probably a decade since I read that book. But I remember that opening. I'm like, what a great entry. The opening of the book is perfect because we were just talking about this when you were at 22 when I was in my early 20s, the existential angst of a young man and women in their 20s is universal. It's like, what is my life going to be? Like, so much of everything is ahead of you.

And so he's on this run and he just feels like he's like, he's been away from his house for seven years. He's got an MBA. He's serving in the Army. And he's living in his childhood bedroom. And he's like, what am I doing with my life? I feel, I'm a grown man. I feel like a kid. Yeah. And the first opening where he's running, he's just like, I'm going to pursue this crazy idea, which turns into Nike. But it ties to what you just. said in the book talks about getting his heartbroken, talks about the death of his son, talks about the fact that he was a bad husband in the beginning. He was absent-minded. And the book ends way before peak. Like way before. At the IPO. Yeah. He's almost saying

that, okay, you know what happens next, but this is how many decades of struggle to get there. One of my favorite books that I recently reread. And it's interesting. I'm at a point now, and I'm reading a lot of new stuff, but I'm spending a lot more time revisiting things that had a profound impact on me because the act of rereading something at a different point in your life, you experience it a totally different way. So like with everything else, including you're asking me some of the things that I'm working on.

For me, it's less and better. less things, more focus, more intentionality, and the same as true of books. And it's been so beautiful at this point in my life to reread some of these great books. And one of my favorites is Man Search for Meaning by Victor Frankel. And I was thinking about it when you were talking about just like hardship and struggle. And he certainly does not romanticize struggle. I mean, he endured the most difficult of human experience. and he tells his story, Victor Frankel, of having survived the Nazi concentration camps. But the idea that meaning can often be redeemed by the struggle. You don't find meaning when things are easy. You find meaning when things are difficult. And when things are extremely difficult,

it's often that same meaning that helps you endure. And there's something so incredible about that. And I just think about it. And 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. It's amazing. I love it. She, like, 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 Warren Peace under her arm. You know, the book is like, it's like this, you know, it's like a door shop.

We should say she's 14. She's amazing. So she's got a tremendous curiosity and thirst to learn. And she also loves reading. But we were talking about this book. recently I had just given her a man's search for meaning. And this idea is so empowering that everything can be taken from you. And you know, the people in Victor Frankel himself in the concentration camp, really it feels like everything's been stripped from you, your family, everything. And yet there is a sliver of sovereignty that is how you experience that, how you react to that, how, you know, your ability to show up, your attitude in the face of enormous struggle and challenge.

And I think that's so empowering because that's such an extreme example. But he has this beautiful quote. I just emailed to her and this will be a paraphrase that 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. So it's like finding that space between stimulus and response. So he encapsulates the idea of our ability to show up in great times and also in the hardest of times.

And the ability to really control our own mindset, which is extremely powerful. I found one of my all-time favorite quotes when I was reading the book zero to one. The quote says, the single most powerful pattern I have noticed is that successful people find value in unexpected places. And they do this by thinking about business from first principles instead of formulas. That is exactly what App Loven has done with their advertising platform, Axon. Axon connects you with over a billion potential new customers inside mobile games. Axon allows you to capture undivided attention. Axon ads are full-screen video ads that are watched for an average of 35 seconds.

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And you can do that by going to axon.aI forward slash Senra. That is axon.com.com.com. A.I. forward slash Senra. What was the most difficult period of your life professionally when you were going through the most struggle or 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 it was like a hockey stick. You had a thriving business. Things were going so well. And I feel like you spent your 20s, like really setting the foundation. And then it was going. My fashion brand, we were doing over 800 million in sales annually. I was running all 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 Dural, which is 800 acres here in Miami,

I had three young children, very young in one case. My son Theo was literally like on my hip. He was six 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. You know, I mean, we lived in New York City.

Half the politicians we knew, they 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. He trusted our instincts. He trusted our intentions,

the fact that we would be honest and truthful with him, and he asked us to go. This was after he had won, around a week and a half after. And so the complete change in trajectory of our whole lives. It's like a 180. There was nothing.

Normally, when people were in for office, they sort of like set themselves up for it. They contemplated for 20 years. You know, they take on smaller challenges, state and local races. You know, my father started with the presidency, won the presidency, and then said, hey, I need you.

And I think both Jared and I in that moment, we looked at each other and we said, you know, we can stick our head in the sand and, like, continue on as we had planned in 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 to not go in? And I think we both knew, like, he's asking us for help. He's giving us an enormous opportunity to give back to a country we love so much. And even if it's

decades ahead of schedule, we should be so honored to do it. You know, I'm pretty intense. And I was like on a path. And now that path was like bearing on unbelievable fruit and I was feeling I had those reps and doing things and achieving things was just easier than it had been when I was 22. And I completely changed the trajectory of my life. So that was like 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 kind of like hand back the keys. You know, there's no, you don't have like a foot in the door and a foot out the door.

So you go through transition, you 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, like 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. And so that was an experience that was both frightening because I wasn't used to it. from when I was a little kid, I actually have recently looked back. I saw a video somewhere that somebody had sent me, and it was me at 17 looking out of at the New York City skyline.

And I'm talking about, like, how I'm going to impact this unbelievably iconic cityscape. And there was no humility about it. It's just like the confidence that you can only have when you're 17, you know. 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. And I was so, so confident in that. So I always knew what I wanted to do. And then it took me different ways. I also started, you know, 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, like, wipe clean.

So you have to then, you talk about, like, knowing yourself. The best thing I did was not just, like, reconnect old wires and do the things I'd done before because that's what I knew. So I actually made the choice not to go back to our family business, 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. So 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 at? But really, like, what do I love and how do I want to spend my time? And that's where I've been ever since, really, like, setting an incredibly high bar for the places I'll commit my energy in time. Also, because now it's like the opportunity cost is so real. I have three kids who need me very much. I have a 14-year-old daughter who I mentioned, a 12-year-old son and a 10-year-old son, and they all need me in different ways. And it's a guy with my 14-year-old, in four years, she'll be out of the house. And I think about, like, what does she need for me right now? You know, she's obviously like 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, me like, you know, rocking her to sleep every night. It's just being here, watching, listening, being available.

You know, 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. You know, they talk a little bit less as they get older. And so that's what I want to make sure I'm here to do. So 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 different challenges on, and they're no less ambitious, but I think the professional part of myself, that like drive, that hunger, that ambition, it's 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? You know, I really, like, 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, started having children relatively young.

I really had a lot of working woman energy. And now that energy, like, 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 that is like, soul project, you know, something that I'm deeply inspired by. Mission-driven, something that gives you energy, something that you can put your soul into.

For sure. I mean, Alan Watts, another one of them. He says, and I think about this all the time, because I'm always thinking about, like, how to grow, how to, become a better version of myself. And he says that you are under no obligation to be who you were two minutes ago. Yeah. And I think about that in the context that if you're not kind of a little bit embarrassed about who you were five years ago, you're not growing enough. So like I look back and be like 10 years ago like, oh, you know, that cringe. But there was nothing wrong. I was just like

in that developmental stage. And I hope that in, you know, 10 years I look back and I view the me sitting and talking to you is not evolved to the place that I am at that point in time. And maybe that's why I also interviewing, like the 80-year-old, as you're saying, they've just, they've been through it, you know, and hopefully they've emerged with perspective and context. Yeah. Yeah. There's just a lot of wisdom that, you know, you accumulate for six or seven decades of surviving. And in many cases, they were successful.

Some accumulate. There's some wisdom. And, but the people who have that, boy, can you learn a lot from them. I, 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 one of the most, my mom's mom. Okay.

But she's one of the most wise people, I know. And she really taught me about, like, love and, like, the truly, like, nurturing kind of devotion to another human being. So I learned so much from her. I learned so much from my children. Like I view everyone, including the people who, like, anger me, maybe especially the people that anger me as teachers, right? Like, if somebody triggers something, a reactive response within me,

like, I actually take the time to think about, like, what is it about that person that provoked this in me so that it's an opportunity for me to learn. But I look at my kids and I learn so much from them because they're so present in the moment. They're like, Rick. You know, they're so comfortable with who they are. You see a child, and there's an amazing phase where they're verbal,

but before the outside world has conditioned them to be anything other than themselves, right? Including parents, right? And there's this, like, magic age where they're six and they're seven. And then at eight, nine, ten, you start to see they're, like, embarrassed if you give them a kiss in front of their school friends. or, you know, this is cool. And that's not. They start to be responding to the feedback that they're receiving that's external to themselves.

But it's magic. And I still, with all human beings, I think in adults, you see it less, like, when they're in their, like, flow and they're, like, they're really, like, in their moment. You see it with great musicians, you know, when they're up on stage and you see that they're, like, lost in their craft and they're just in it. But I think with kids, you see it most clearly. And I watch, I mean, with my daughter, it's when she's around animals, specifically horses. You know, when she's out on her horse, she is so, like, complete in herself.

With my son, it's Joseph. It's when he's in nature. You know, he's out on the ocean and he just, he loses himself. And I see him just, like, staring at, you know, it's beautiful. And it's something that I learn from. Like, I actually feel myself decompressing. I'll put down my phone. I'll stop trying to take a picture of him.

experiencing this and be in it with him. 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, but like chess, poker, backgammon, dominoes,

like, you name it, we play it. So that's why we have, like, three different game tables around the house. But it's a beautiful thing to see. Go back to this period of reflection. Now it's almost like you had like a second birth, like a rebirth. You have an opportunity as a grown,

adult, a mother, very successful. Now I get to choose. Everything in my past is gone and I have a blank sheet of paper to work from, right? How long was that time period to figure out what your next move was going to be? Probably the smartest thing I did was not just like not just gravitates towards the playbook I knew. I actually wanted to really like sit with it. So I took around six months where I really was, I was extremely proactive in saying no to all partners, people had ideas. And I really wanted to just like 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. And that was one of the greatest things. I did because it allowed me to set up my life here really intentionally and build something, build a reality that I love living every single day. My brother-in-law always says, the most happy people are happy to go to work and they're happy to come home from work. Oh, Josh? Yeah. I've seen this. And I think that's 100% right. And you're as happy as your least happy child. So making sure my family was set up. And then I think I started to become curious. And part of my process is to read, to study, part of the reason I love investing is I have an insane curiosity for what's out there.

Like what could be, what is, what people are doing, what people are building. I love being surrounded by first and foremost, like, kind, good people, driven people, but also people with huge ambitions and wild imaginations and who see what the world can be. and have their finger on the pulse of that. So I think really spending time in a lot of different ecosystems that wouldn't have been necessarily natural to me coming out of a real estate and fashion background to really immerse myself in technology and robotics and biotech and even, you know, health tech,

I think there are some amazing things that are happening now where we can really like leverage information to catalyze our changes in our, our own behavior. You see all the wearables like who and other companies like that. So I really wanted to spend a lot of time just with these people learning from them and helping accelerate the businesses that I most believed in. And that put me on a beautiful path. And in some cases that took me back to the beginning, like in the case with Cizan and what we're building there, I sort of came full circle. And that project will ultimately be the culmination of all of my

experience prior in real estate and with travel. So this is one thing that I would love for you to explain your thinking on. When you shut down your business, you went into government, you resigned from like 350 things. Yeah. Now you have this. You literally sit with the Office of Government Ethics and they review your whole life. And they tell you if anything could potentially be a conflict of interest. You either have to divest of it. You have to put it into trust. So they go through everything. And they're, they just determine it. They tell you what to do. And then you go back, you've done it, you show it to them, and then they have to stamp it. It was like a wild untethering from the life you were building, you know, in like super small ways and then much

larger, you know, selling businesses and selling assets in some cases building. So it was a very unique experience. But then you're really like in it and free of all you had been doing in the past. But I can't help but think in this like new reset, this new like 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 like I feel the conversations we have, you're, you have these reoccurring themes. It's like fewer, deeper, fewer or better. For sure. Can you explain the change of decision making there? You think about moments in your life. And I think that moment was an inflection for me. And in so many ways, I emerged a very different person. But I, I think, you think about moments in your life. And I think that moment was an inflection for me. And in so many ways, I emerged a very different person. But I. But I. But I, I think one of the things that also happen is that at a time when I was like really running and really happy with the trajectory in my life was headed on, the treadmill stopped. I completely pivoted. And that afforded me the opportunity later to decide, like, which races I was going to compete in versus not.

So there's something that doesn't typically happen to somebody when they're in their early 30s. You know, that's when you're like very tethered to the path that you've charted for yourself. So I think in the end, it was a great blessing. Like, do my, I think my life would have turned out great? Sure, right? But it did give me a lot of perspective, and it gave me the ability to really, like, mark things in my mind to market, create a lot more simplicity for myself, really only commit to building things that I would be passionate about over the long term.

You know, some of the things I was working on were legacies of, like, my early 20s, where I was just getting started. And I think part of what you should be doing when you're young is like throwing a bunch of stuff against the wall and seeing what fires you up, seeing you have to have experience. And sometimes the best experiences are the horrible ones because you know that's not like the right path for you.

Some of the best bosses are the worst ones. Is you learn from them how not to treat people, right? So I think it's all good. But I think the whole experience of like detaching from everything that I had built up to that point. And then as like a more fully formed adult coming back and being super intentional was very clarifying. You know, Jared loves the book, Essentialism. And we talk about it all the time because for him, like simplicity is king.

He loves distilling complex things and ideas and systems into the most simple version. And 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. You know, there's like the famous line. I wrote a long letter because I didn't have time to write a short one. Like I think about that, it's like much harder to write something precise and to drill down why it's so challenging to write a book.

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forward slash senra. Jared keeps hounding me to do an episode of founders on the book Essentialism. Yeah. And 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. And when you identify that, I got to have lunch with Sam Zell before he died. Yeah. Because our mutual friend Rick Erson is the one that set up that lunch. And one thing that I talked to Rick about is like he was mentored by Sam for 20. five years. And he's just like, I didn't know anything. I was in my early 20s when I met him and I'd bring him a deal and I'd be like, you know, there's like 10 things we have to take care of.

And Sam would, Sam would look at it. He's like, there's one. If we take care of point number five, then everything else will work itself out. And I asked Sam about that. And he's like, I learned that from Jay Prisher, which is some people consider the best deal guy of all time. And he's like, I would used to bring him deals when I was in my early 20s. Like this whole thing is replaying. And I like, look at all these things we have to do. And Jay's like, no, you only have to do one. You have one problem here to solve and the rest? The best leaders, the best entrepreneurs, they can see clearly. They can find a signal in the noise. I think about it almost like the golden thread. There's one thread you can pull in the sweater unravels, or you can do a thousand different things. So really honing in

on what are the variables that matter most. And that's not just true of business. That's true in life. Like, what are the times that really matter that you need to be there for your kids? And are you showing up in those moments for your spouse, for your friends. And I think being able to see clearly, that's everything. So you think about these great founders, and they're solving meaningful problems oftentimes simply, right? Like they're removing a lot of friction to people's lived experiences with products or services. And then they're distributing it aggressively, right?

So it's not just the idea. The idea is becoming known and being distributed to the consumer. And then they're enduring over the hardships that will inevitably come as they build a big, meaningful business. So that ability to then do that, but do it over time with the same level of commitment, stamina, passion. And, like, fundamentally, that's what entrepreneurship is. I'm kind of obsessed now.

about this idea of this reset that you got to have, you know, because it happened after probably a great deal of pain, I would imagine. Not pain, just challenge, right? Like intensity, growth. These were amazing life lessons. Like, 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 real time. What we could get done in the third year versus the first or the fourth year versus the second 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.

I look at a lot of people. They call it Potomac fever. You know, they can't help. Once you're close to. to that level of action and power. You even see it with business leaders. They like gravitate towards it. It's very hard and you see them.

They hang around the hoop. They go into the private sector for around two weeks until they cycle back in at like a slightly higher position. But for me, it was always about being asked to surf, being honored by that request and feeling a great privilege and being able to do it, feeling really good about the body of work we were able to accomplish. Like I, you know, I personally was entrusted to work on issues. like workforce development, vocational education,

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, 40 million Americans benefited on average $2,500 a family by the expansion of the child tax credit. That is incredibly meaningful work, paid family leave, the first ever national plan.

federal employees having access to paid leave for the first time. So, you know, human trafficking, nine pieces of legislation, I champions 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. 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 for me that, you know, the first time around, I could theoretically, I could imagine it would be intense.

And I would know sort of the sacrifice my children would have to bear. I would imagine it. But, you know, 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. And 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, that's 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, that 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 plant harvest do that? Simply, it had been done that way because it had always been done that way. And there was no secondary market for any fruit or vegetable that didn't meet an exact specification in terms of size and color sometimes, even though the taste and the quality were in no way compromise. So there was just no market for it. So we said, well, that makes no sense at all. And let's stimulate the demand side and create demand so that we could support these small and medium-sized farmers. And this is, you know, going back to just like listening. I started listening during the COVID pandemic to the challenges of farmers, small and medium-sized farmers.

And that was an extreme situation because the supply chain just completely shut, right? So if you had a farm and you had a perishable product like a strawberry, suddenly all the restaurants are closed, unless you had an account with Walmart, you had nowhere to sell your produce into. And so you'd till it into the ground. As part of COVID and as part of the CARACS, I created something called the Farm Roast Family Food Box Program, where we created grants to buy this great product and surge it into communities and need,

keeping these small and medium-sized farms alive and thriving during this incredibly difficult time, saving the job of the distributors who would transport between communities and the farms and obviously feeding a lot of people who were in need. But at that time, I started looking at the business more generally and realizing, like, why isn't there a secondary market? Like, 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 cosmetic specification that's really exact? You know, it's like everything is so uniform in size. It's very different in other areas of the world in Europe. It's like organic. Things are slightly bigger or smaller. So we sought me and my partner to start to stimulate demand by working with large consumers and sharing with them the issue and getting offtake for these small and medium-sized farmers that's meaningful. So companies from Chobani,

now all of the fruit that we find in their beautiful yogurt products and smoothies is all sourced by Planet Harvest from small and medium farmers. That would have been 100% waste. It would have been tilled under. So, you know, 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 in strawberry alone that's being tilled into the earth

as opposed to going into yogurt or ivory. Why do they put it back into the earth? Well, 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 and then they would have to ship it. Okay. And 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 of 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 you go after a lettuce harvest and you look at the field, it looks like the field is full of lettuce. 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. And 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 of how do we get this into pre-made 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. So the incremental revenue to them is deeply meaningful. And 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,

and that's the type of problem that Jared says something that I think about all the time, that he loves being contrarian by being obvious. and like 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? 40% of produce grown in America doesn't leave the field and him saying, how can I help? So that's a really like mission-driven business that I'm deeply passionate about, but I think we'll 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 non-for-profit. So something that I'm really excited about came from a conversation I had with a great friend, the technology investor, who you know, Alad Gill. And we were talking, this was years ago, and we were talking about what are some of the positive use cases for AI? Like, what is the light in the force, if you will,

and that isn't being executed upon currently? And 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 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. or Marcus Aurelius' 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 that we 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 Bronte. You think about Marcus Aurelius or Hepatitis. All of these works are available in the public domain. So how can we use AI to translate them into all the world's commonly spoken languages and make them accessible for free to everyone in either text form or as an audiobook? So we're working with a lot of the large language labs to do exactly that. to both do the translations in a really great high fidelity way and most of the world's spoken languages

to make it accessible for free to everyone who has internet access and to also have audio translations. You can actually even query into the text and ask questions as you read along. So there's no reason, whether it's a high school student in Philadelphia who can't afford to buy Jane Eyre for their eighth grade class. Like there's no reason if that's in the first

public domain, they 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. I go to these websites. Obviously, I'm obsessed. I read more than almost habe-O. So I go to these websites, too, and the format's terrible. This is- They'll scan pages of a book in and upload it into the universe, but this is like a product

that's meant for a consumer. We're calling it, 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, and people will give us, feedback on each of the translations. But imagine now meditations will be translated into most of the world spoken languages. So we're covering like 95% of all languages spoken and 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 the Lod where I'm like, what are you most excited about? It's not being done. And he told me, he's like, there are so many unbelievable works by the greatest thinkers, humanity is 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 anything. Anything I can do to help on that project, obviously, you know it's close to my heart.

I would definitely, you know, volunteer if you need any help. I've been translating, using AI for the last few years, trying to translate books that are not in English to make episodes of founders on them. And the translations are getting so much better, so I think you guys are perfectly timed. 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 like, this happened 15 years ago. And the translation was so bad it's like, this happened three, five-year periods ago.

Yeah. Like, that's a funny way to say 15. Five years ago, we couldn't have done this one. Yeah. But now the large language models are so good. And generative AI is really allowing us to do it affordably. Do a way with high fidelity. The voices are amazing.

So 11 labs is helping. Have you spent time with Maddie? I have. Yeah, he's amazing. So he's helping us with the audio books that will accompany each of these. But it's amazing. And we are really like working deep into some obscure languages where people really, they don't have access. They have internet.

They won't have a library. They probably won't have a bookstore. Rural communities, but also for students. You know, right now, if you want to read Plato's Republic, you know, you go and pay a publisher $35 for something that's in the public domain that every six months they generate a new copy of and slap on a new piece of artwork on the cover and students go and they pay for it. So this to me is just a fun way to give back, to share some of the books, obviously, that have so profoundly influenced me. but 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 that there's going to be all these positive things that come out of this that you and Elad possibly could not possibly predict. We're having fun even like the first, you know, it's really hard to choose a thousand books.

And so people will say, well, you miss this. And of course we did. So even just the exercise of like what are the most meaningful books for us? what should we translate next? How big is the scale of the project? Like, you know, how many, you know, we're figuring out. The answer to that question is as big as you want to be. Exactly.

Like, there's no limit. You're not, it's not a physical library, physical space that you're restrained to 1,000 or 2,000 or even 10,000 books. But what I was saying is, like, the reason I think these kind of things are very important. I also think podcasting plays a role in this too is I'm reading Kelly Johnson, who's the most famous and most successful aircraft designer in history. And in his autobiography, he says the most, the most. One of the most important things that ever happened to him was Andrew Carnegie had the biggest impact on his life. And he never met Andrew Carnegie because Kelly Johnson grew up in exactly what you're describing.

Very poor rural community. There's no, he doesn't have electricity for God's sake because there doesn't have access to anything else. And this was when Carnegie was building all these free libraries and putting them all over the United States in these tiny communities. And Kelly would just go there and he would just live in the library. And he's like, I read every single thing about aviation. I read fiction. I read all these things that impacted me. and I used 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. You know, 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, you know, be able to learn from the amazing people who came before, even if you don't have direct mentors in your life that can expand your thinking and inspire you.

Do you know who didn't have a direct mentor? Who? Elon Musk. I remember watching this interview with him, that this guy Kevin Rose did back in 2012. And Kevin was trying to figure it's like, they're in Tesla's factory. That's where the interview's happening.

And Kevin's like, what the hell? Like you come from South Africa, you go to Canada, then you go from Canada to the Bay Area. You didn't have any money. He's like, how did you learn business? Did you have mentors? And 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 and historical context. So I thought biographies and autobiographies were helpful. And I was like, oh, 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 I say I want, I'm like deeply want to emulate every aspect of their life.

Probably nobody. Probably nobody. You know, Jared's pretty close. For me, why I say that is because there are some people who I think are brilliant in business, right? They're true visionaries and their private life is a wreck. So are they still brilliant or are they stupid? Like if you're that smart, how do you not figure out like how to create sort of a stable life for yourself and that like, you know, is good for the soul, good for the heart?

You know, thank goodness they're doing what they're doing. It's a great gift to humanity. But like I wouldn't want to emulate that because I want to raise my children. And I think that work is more important than that work. So, or you'll have people, you know, on the, it's all across the spectrum, but there are very few people I say, wow, like in every aspect of their life, their priorities feel calibrated and they're doing well, not flawless, because perfection's not possible, but, but they're doing well. And why I say Jared is he's really, you know, he can be going through the most intense experience and like the kids don't feel it. Like he's deeply present wherever he is and whenever he's doing. He's not always physically present, but he's always available.

Emotionally, telephonically, he'll drop anything he's doing it. Like he somehow has the ability to always be in the right place, regardless of what he's struggling. And that's true for his partners as well. He's a very long-term thinker in that he's, you know, 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.

You've seen you have one with him and you've seen him with others that are truly built on trust. And that's because he's more of a giver than a taker. And over time, that ends up benefiting him in all sorts of incredible ways. But that's like ancillary. You know, he doesn't come at it from a place

of thinking well over the long term, just who he is. And he's very comfortable with himself. He's just very comfortable being exactly who he is and very non-performative. So I learned 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 second now? So I'm going to have created a monster.

But that's the thing. He won't. He really has, like, almost no ego. It's to the point where, like, I'm incredulous by it. Like, I'll get upset about things for him. And he, like, doesn't care. If, like, if somebody criticizes him and he doesn't know that person, it just doesn't affect it. It doesn't mean that he won't, like, say, okay, well, that's warranted and, like, recalibrate.

But it's just not going to, you know, he cares about the opinions of those he loves. Well, we don't have to edit it because, as you just said, I spent a lot of time with him, too, and he talks about you the same way. And it's legitimate when he doesn't think I'm going to go back and obviously tell you or anything like that. And we've had a lot of dinners talking about this. So you guys- By the way, key to life, right? Marry the right person.

Yeah, for sure. Marry someone who sees you as put you up on a pedestal and sees you as I don't think I've ever heard. He sees me in a way that like I aspire to see myself. This is very rare where you two have. Like this is actually really beautiful what you just said about him because I was sitting there thinking as you were speaking

it's like very few people would describe, you know, their spouse is, you know, almost perfect in their, for lack of a better word. Like, that's actually incredible. So there's two things that we mentioned that I want to come back to, I think are super important and I'm super curious about.

So you mentioned, you mentioned essentialism. Yeah. And you mentioned opportunity cost. You have essentially in front of you unlimited opportunities on 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? Like, when you're deciding, hey, I want to meet this founder, I may invest with them. or I may want to partner with somebody in this project like Planet Harvest in the profit domain or nonprofit domain like you did with Elad.

Yeah. 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. Like, who would have thought, right? And I'm investing in tech companies and helping build these amazing businesses that are so beyond what I would have ever. imagined myself doing. Even the scope and scale and ambition of Cizan, this incredible project will

have hotels and resorts and wellness, all of it is, it's almost daunting in its size. And an apartment for me? Obviously. Well, community is like at the heart of, I think, how people want to live, right? So I'm thinking a lot about how to create great community for families, for connection, because I think that's like the currency. Like, attention, like getting somebody's attention, keeping it, and creating an enabling environment for exactly that. But anyway, but I think for me, it's, I always just try to be receptive to conversations with others and, like, what sparks something in me.

And then I go deep. So my daughter will joke with me. I mean, I have like 100 ideas a week. And I start to go into them. And she's like, what, you didn't do that? And I got all excited about it. what about this or 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 around reading. So any challenge

I'm about to take on, I become like a PhD in that subject. So with the Sazon project, I'm reading all the best Albanian writers, and I'm trying to understand the country through their eyes. Oh, it's smart. And fiction, nonfiction, all of it. And you immerse yourself in sort of the experience, the lived experience of these great observers of the truth. And then you get closer to it, right? You can't just like impose yourself upon a country or culture. You have to understand it first to do it in a beautiful and delicate and meaningful way. But that's the approach I take to everything. So I listen to a lot of people. I try to surround myself with people that 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 like being interested in the world around you. I always tell them that only boring people get bored, like there's too much to learn. But I also tell them in the context of this 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 sort of open channels for me and help me grow. And sometimes that's in a very intimate way, people who are really, like, just in touch with themselves and who can help me be a better mother, a better wife, better human being. And other times, it's great business leaders. But how do you decide who to let in?

Like, what is, what kind of person do they have to be? First and foremost, like a kind person. Like, life's too short. Like, there are a lot of successful assholes, but I'm just not interested. Like, 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. That's a buffet among her. They say that over and over it. I would do a handshake with a good person over, like, the most ironclad, you know, white shoe law firm created contract any day of the week.

So I'm just at a point of 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 people who are like kind, good people who I admire and who I can learn from. And there are so many of them. So the choice will never be for me to partner with sort of the opposite of that. So I try and find good people. I try and find people who can help me grow, who I can learn from. Then I dive deep into the subject matter through reading, through podcasts.

Like I listen to a ton of podcasts. Yours being my favorite, obviously. obviously on a variety of different people and subjects. And then you have to get going. Like a mistake a lot of people make is they get so excited about the idea. They keep on like ruminating on the idea. They keep on pitching the idea. They don't get to the point of actually like doing it.

And you learn a lot just in the early phases of bringing something to market. Like that motion can completely reorient your business, right? because you receive feedback around, like, for example, planet harvest, we were creating demand for something that there was no demand for. I mean, even the farmers weren't even taking this produce out of the field because there was no market for it. So we had to create a market. So we had to speak with the consumers and find out what would they pay for it?

And what would they get from it? They'd get the story of the small farmers they were supporting. They would get 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 to them, and then we had to hear from them, like, what was that worth of them?

I think it's really important to get that message out there. There's one of my favorite books. It's called The Banana King, I think Sam's a Murray. Or no, the fish ate the whale. I heard your episode on us. Yeah, Sam's Murray. I forgot the subtitle, but it's about the biography of Sam's a Murray. We're working with Chiquita Banana now,

which is like the largest, and helping them think about their excess and utilizing it. and I shared that episode. But he did something very similar where there's a line in the book where, you know, they were,

he started in bananas, obviously, and they were just throwing them away because they would rot in like two days and they couldn't sell them in the next two days. And so he basically, there's a line in the book that I thought of when I hear you talk about Plain Harvest.

Like he saw opportunity where others saw nothing. Yeah. And 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. In your case, you said that, you know, they just did it this way because it's the way that's always been done.

So if you just go into a new situation with fresh eyes and you're like, why, why, just keep asking why. You'll eventually get to, you know, well, that's just because how it's always been done. A hundred percent. And, like, that's the best answer in the world because that means, like, there's ready for just funding. There's innovation that you can do there. And I think that's what's so cool about doing the early stage investing that I'm doing.

Like, obviously, Affinity does later stage investing. But some of the earlier stage, it's really about you have to be a good listener. You sit down with a founder and they don't have the track record. In some cases, they haven't even begun to execute their business plan, right? They haven't commercialized it. And 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? Like you're trying to understand, does the person have 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, the leadership skills, all of these traits that you have to have or have the humility to know you don't have and supplement by hiring the right people, right? So it's an assessment of the human being sitting across from you and also of the idea that hasn't yet been proven. And in some cases, the more audacious, the better. Because I'm not interested really investing in like boring things.

I like investing in things that have the ability to be transformational. So these often tend to be big ideas, often tend to be unproven ideas. and you have to be a good listener because you don't have a lot of data to support what they're doing yet. And 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. And I think you're perfectly suited as your personality 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 fish, great entrepreneurs I've read. It's just like new ideas are so fragile.

And it's so easy to kill an idea prematurely and to not let it grow. And you just have to give it room and time for it to grow, just like a human being. Just like I think Jeff Bezos uses the idea, the analogy of like an acorn turning into an oak tree. Yeah. It doesn't happen in a week. It doesn't happen in a year. It's going to be a multiple year process that we have to understand that going into it. And you may end up at a place that's very different from where you started.

You mentioned Jeff. Like he was selling books. Right? So that's where it becomes, it's the idea, and then it's the founder. And what will that idea morph into? Very rarely is it a straight path. Most often it's something completely beyond the original aspiration. Toby, I heard him on your show. But, you know, these, so there's a certain sort of neurological flexibility, you know, that these founders have. that they can be so passionate about something, yet pivot into something else they're equally passionate about that becomes the ultimate manifestation of that original acorn. And I think your life, what you share with us so far in this conversation, is a perfect example of that because you've done that in your second act as well.

I'm honored to call your friend. Thank you very much, Ivanka, for taking the time. This was absolutely perfect. Thank you. 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.