Ivanka Trump on Building an Authentic Life

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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02David Senra?

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

• 0:08Speaker 01

  My work life specifically.

• 0:11Speaker 01

  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 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. 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,

• 0:55Speaker 01

  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

• 1:39Speaker 01

  is, I think, super interesting. And then 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.

• 1:55David Senra?

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

• 1:57Speaker 01

  Yes, it is.

• 1:58David Senra?

  There's no power on this island. You're building, you're building everything from scratch. Correct?

• 2:02Speaker 01

  Well, 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.

• 2:46Speaker 01

  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.

• 3:25Speaker 01

  That requires a lot of vision, the collaboration of some of the greatest masters that exist. So I was just, 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.

• 3:55David Senra?

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

• 4:01Speaker 01

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

• 4:19David Senra?

  Are you guys hearing this? There's like six people off camera than a bad driver.

• 4:26Speaker 01

  Then you drive absolutely crazy. But actually, that's where you get to something, you know? 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

• 5:06Speaker 01

  beautiful and intentional with a highly functional space. And one of the things I love about real estate is it's, 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.

• 5:32David Senra?

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

• 5:38Speaker 01

  Oh, yeah.

• 5:39David Senra?

  Like, to build something that you know lasts longer than your own lifetime.

• 5:43Speaker 01

  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 DC 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 one 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

• 6:29Speaker 01

  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...

• 6:44Speaker 01

  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. So, and that's what we're going to do with this project, Cezanne.

• 7:15David Senra?

  Yeah, how do I say it?

• 7:17Speaker 01

  Cezanne.

• 7:18David Senra?

  Cezanne, 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." 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 you set that up immediately. But Dana has this thing, this is like a simple genius to the way he operates his life, in my opinion, and his business. And the piece of advice that he would give to young entrepreneurs is like, 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, 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?

• 8:00Speaker 01

  I was 22.

• 8:03David Senra?

  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?

• 8:12Speaker 01

  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.

• 8:45Speaker 01

  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.

• 9:30Speaker 01

  And there's something very important about, you know, 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 as 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.

• 10:12Speaker 01

  And I think we're drawn, as people, if you look at sort of pop 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.

• 10:39David Senra?

  I want to tell you about the presenting sponsor of this podcast, Ramp. I have been reading a lot about SpaceX lately. SpaceX is one of the most valuable private businesses in the world. And one of the main themes in the history of SpaceX is constantly attacking and questioning your costs. Ramp helps many of the most innovative businesses in the world do exactly that. The median company running on Ramp cuts their expenses by 5%. And one thing SpaceX has demonstrated is that a religious dedication To controlling costs can help actually increase revenue because you can pursue opportunities you couldn't otherwise. And we see that in the Ramp data, too. The media and company running on Ramp also grows their revenue by 16%. So when you're running your business on Ramp and your competitors are not,

• 11:22David Senra?

  you have a massive competitive advantage that compounds over time. Ramp is the only platform designed to make your finance team faster and happier. Many of the top founders and CEOs I know run their business on Ramp. I run my business on Ramp and you should too. Go to ramp.com to learn how they can help your business save time, save money, and grow revenue. That is ramp.com. How did you get to the point where, you know, you're 22, you started your first company?

• 11:48Speaker 01

  Yeah.

• 11:48David Senra?

  You didn't know yourself. Now, several years later, you do. How did you do this?

• 11:54Speaker 01

  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,

• 12:39Speaker 01

  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 device. That we we carry with us. I think it requires a tremendous amount of discipline to create stillness.

• 13:23Speaker 01

  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. This is great. So we're currently in a moment where each of the three, each of my three children like completely different breakfasts. So I'm like basically a short order chef.

• 14:07Speaker 01

  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'm 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 I'll think. I keep that beautiful moment in my day as sort of an anchor to to both offer sort of thanks and gratitude to God and 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.

• 14:51Speaker 01

  I come back to the house, I work out, and I do all of that in, 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 much more proactive and 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 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.

• 15:35Speaker 01

  But but really trying to sort of find stillness so I can I can sort of hear what the universe is is telling me. Rick Rubin talks about this in 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 I listen to so many people and they have these eureka moments in the shower, which I do, too.

• 16:16Speaker 01

  But I think part of the reason that happens is because they don't have their cellphone in the shower. Like they literally, whether it's five minutes or 20 minutes, they're there alone with their thoughts. And suddenly, the ideas start to come in.

• 16:30David Senra?

  You mentioned the creative act. One thing that you and I have bonded over the last several years that we're 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 Catmull, 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 you're essentially taking a lot of time to know yourself. And then, once you did that, you're just building your business for you first.

• 17:04Speaker 01

  100%. Naval, 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 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.

• 17:47David Senra?

  For thousands of years.

• 17:48Speaker 01

  And there are not that many of them. You know, there's humanity, like, all of who we are, it just echoes over time with 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.

• 18:33Speaker 01

  So, you know, to me, that's very, very interesting. And 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 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 everything they've learned, everything they've experienced. I think there's just so much value in opening that book and listening to them.

• 19:07David Senra?

  It's silly not to. Yeah, I think, I really do think it's irresponsible not to. You're close to some of the Walton family members. And I was just with one, Sam's grandson, Sam Walton's grandson, at an event yesterday.

• 19:20Speaker 01

  Who's that?

• 19:21David Senra?

  Stuart.

• 19:22Speaker 01

  Oh, yeah. I know Stuart. He's great.

• 19:25David Senra?

  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...

• 19:33David Senra?

  Writing of the co-author that Sam had on his autobiography, because Stuart listens to my podcast founders, my other podcast founders. And he's like, I'm going to try to get this to you. Just I can't use it for like, public consumption. But just because you, I'm really obsessed with Sam Walton. I admire him greatly. And he's like, this is kind of like, round out some things that you didn't know about him.

• 19:50Speaker 01

  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.

• 20:01David Senra?

  But it's also an act of 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 pain, cancerous all over his body. He knew he did not have, he had limited time left on his earth. And what did he do? He's like, hey, I had 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 act of service cannot 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. So will you please write a book?

• 20:46David Senra?

  And she's like, it's funny you bring that up, because she's had an offer for like, 10 years. I was like, you have such a unique lived experience working on one of the most important companies in the world.

• 20:56Speaker 01

  Yeah.

• 20:56David Senra?

  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.

• 21:05Speaker 01

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

• 21:09David Senra?

  Yeah.

• 21:10Speaker 01

  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.

• 21:19David Senra?

  Yeah.

• 21:20Speaker 01

  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, there's a little revision of 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.

• 21:37David Senra?

  You just read by mind.

• 21:38Speaker 01

  By Phil Knight. Then you're really putting it out there and leaving it out there. And, 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 major company or something. You know, because there's something.

• 22:02Speaker 01

  So vulnerable about doing it. Plus, it takes a tremendous amount of discipline to distill the wisdom accumulated in our 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? Like, it's like they don't know, they just do it. So I think for a lot of people, it's like an 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.

• 22:42David Senra?

  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 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 Shoe Dog because I just finished reading it for the third or fourth time. And I just recorded another episode on it. It'll be out soon.

• 23:06Speaker 01

  That's one of like the great opening lines. What's the opening line? It was something about, you know, the pioneers and

• 23:11David Senra?

  Okay, so

• 23:12Speaker 01

  And then there was us. Like, some died along the, some made it, some died along, and then there were

• 23:17David Senra?

  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, is 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. That leaves us.

• 23:45Speaker 01

  I love it, yes.

• 23:46David Senra?

  And he believed.

• 23:47Speaker 01

  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.

• 23:53David Senra?

  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 and woman in their 20s is universal. It's like, what is my life going to be? What, like, so, so much of everything's 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 served in the army and he's living in his childhood bedroom and he's like, what am I doing in my life? I feel I'm a grown man, I feel like a kid.

• 24:19Speaker 01

  Yeah.

• 24:19David Senra?

  And the first opening where he's running, he's just like, I'm gonna pursue this crazy idea, which turns into Nike. But it ties to what you just said. In the book, talks about getting his heart broken, talks about the death of his son, talks about the fact that he was a bad husband in the beginning. He was absent minded.

• 24:37Speaker 01

  And the book ends way before peak.

• 24:40David Senra?

  It ends at the IPO, at the IPO.

• 24:42Speaker 01

  He's almost saying that, okay, you know what happens next? But this is how many decades.

• 24:48David Senra?

  The struggle.

• 24:49Speaker 01

  Struggle to, to, to get there. One of my, one of my favorite books that, um, that I recently reread and I'm, it's interesting. I'm, I'm at a point now and I'm, I'm, 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, 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, and the same is true of books. And it's been so beautiful at, at this point in my life to reread some of these great books.

• 25:32Speaker 01

  And one of my favorites is Man's Search for Meaning by Viktor Frankl. And, you know, 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, of human experiences. And he tells his story, Viktor Frankl, 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.

• 26:16Speaker 01

  And, and, and I just think about it and I'm, I've been talking to my, 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, I love it. She like blows me away.

• 26:28David Senra?

  That's a gift.

• 26:29Speaker 01

  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.

• 26:37David Senra?

  Oh, my God.

• 26:38Speaker 01

  You know, the book is like this, you know, it's like a doorstop.

• 26:41David Senra?

  We should say she's 14.

• 26:42Speaker 01

  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 Viktor Frankl 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.

• 27:27Speaker 01

  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,

• 28:10Speaker 01

  which is extremely powerful.

• 28:13David Senra?

  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 AppLovin 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. That is retention that blows other ad platforms out of the water. You can launch on Axon in minutes. You set the goal and Axon achieves it.

• 28:56David Senra?

  There's no complex setup, no expertise needed, and Axon scales quickly. They can put your ads in front of over a billion potential customers. Other businesses have seen immediate results, have scaled to hundreds of thousands of dollars of spend per day and increased their revenue by millions. So you want to get started quickly before all your competitors are on Axon. And you can do that by going to axon.ai/cenra. That is axon.ai/cenra. What was the most difficult period of your life professionally? When you were going through the most struggle or pain or indecision?

• 29:37Speaker 01

  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.

• 29:53David Senra?

  You had a thriving business.

• 29:54Speaker 01

  Things were going so well, and I feel like you spent your twenties 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 Doral, 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?

• 30:39Speaker 01

  I mean, we lived in New York City. Half the politicians we knew, they were Democrats who would come annually to, 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. It was, there was nothing. Normally, when people run for office, they sort of like set themselves up for it. They contemplated it for 20 years.

• 31:23Speaker 01

  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 ourself 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 like decades ahead of schedule, we should be so honored to do it.

• 32:08Speaker 01

  You know, I'm pretty intense, and I was like on a path. And now that path was like bearing 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,

• 32:53Speaker 01

  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 over the New York City skyline. And I'm talking about like how...

• 33:22Speaker 01

  I'm going to impact this unbelievably iconic cityscape. And there was no humility about it. It was 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, 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.

• 34:05Speaker 01

  When you leave, everything's all of a sudden like wiped 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?

• 34:50Speaker 01

  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 having, setting an incredibly high bar for the places I'll commit my energy and 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.

• 35:20David Senra?

  And it's got to go by like that?

• 35:21Speaker 01

  Yeah. It's, I mean, with my 14-year-old, in four years, she'll be out of the house. And I think about like, what does she need from 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,

• 36:06Speaker 01

  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.

• 36:30David Senra?

  Was it all work when you were 20?

• 36:32Speaker 01

  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.

• 36:53David Senra?

  Yeah.

• 36:53Speaker 01

  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.

• 37:13David Senra?

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

• 37:17Speaker 01

  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.

• 37:34David Senra?

  Yeah.

• 37:34Speaker 01

  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 at me like 10 years ago and 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 also interviewing like the 80 year old, as you were saying, they've just, they've been through it, you know, and hopefully they've

• 38:12David Senra?

  Just further down the path.

• 38:13Speaker 01

  With perspective and context.

• 38:15David Senra?

  Yeah.

• 38:15Speaker 01

  Yeah.

• 38:16David Senra?

  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.

• 38:22Speaker 01

  Some accumulate. There's, 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 interests, but she is one of the most

• 38:39David Senra?

  This is your mom's mom, Kirk?

• 38:40Speaker 01

  My mom's mom.

• 38:41David Senra?

  Okay.

• 38:41Speaker 01

  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.

• 39:21Speaker 01

  They're like, Rick, you know, they're, they're, 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.

• 39:40David Senra?

  Yeah.

• 39:40Speaker 01

  Right? There's, and there's this like magic age where they're six and they're seven. And then at eight, nine, 10, 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, and I watch, I mean, with my daughter,

• 40:23Speaker 01

  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, and it's, it's something that I learned 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, 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.

• 41:07Speaker 01

  So that's why we have like three different game tables around the house, but it's a beautiful thing to see.

• 41:12David Senra?

  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, blank sheet of paper to, to work from. Right? How long was that time period till you figured out what your next move was gonna be?

• 41:35Speaker 01

  Probably the smartest thing I did was not just, like, not just gravitate 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 old partners, people had ideas and, 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.

• 42:18Speaker 01

  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."

• 42:36David Senra?

  Oh, Josh?

• 42:37Speaker 01

  Yeah.

• 42:37David Senra?

  I've seen this.

• 42:38Speaker 01

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

• 42:56David Senra?

  I was gonna go here next.

• 42:57Speaker 01

  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, 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, in technology and robotics and, and biotech and, and even, you know, health tech.

• 43:40Speaker 01

  I think there are some amazing things that are happening now where we can really like leverage information to catalyze our changes in our own behavior. You see all the wearables like Woo 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, and that put me on a beautiful path. And in some cases, that took me back to the beginning, like in, in the case with Sazan and, and, and what we're building there. I sort of came full circle and, and that project will ultimately be the culmination of all of my experience prior in, in real estate and, and with travel.

• 44:21David Senra?

  So this is one thing that I would love for you to explain your thinking on. When you shut down your business.

• 44:27Speaker 01

  Yeah.

• 44:27David Senra?

  You went into government, you resigned from like 350 things.

• 44:30Speaker 01

  Yeah.

• 44:30David Senra?

  Now you have this.

• 44:32Speaker 01

  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, buildings. So it was a very unique experience, but then you're really like in it and free of, of all you had been doing in the past.

• 45:16David Senra?

  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? Cause like I feel the conversations we have, you're, you have these reoccurring themes. It's like fewer, deeper, fewer, better.

• 45:33Speaker 01

  For sure.

• 45:33David Senra?

  Can you explain the change of decision making there?

• 45:36Speaker 01

  You just think about moments in your life. And I think that moment was an inflection for me in, in so many ways. I emerged a very different person. But I think one of the things that also happened is that at a time when I was like 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 like which races I was going to compete in versus, 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.

• 46:20Speaker 01

  Like do I think my life would have turned out great? Well, 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, to market, create a lot more simplicity for myself. Really only commit to building things that I would be passionate.

• 46:40Speaker 01

  About over the long term. You know, some of the things I was working on were legacies of like my early twenties, 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 because you learn from them how not to treat people, right? So I think it's all, 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.

• 47:23Speaker 01

  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, when you're able to do that. And it's, 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 if you're distilling complicated ideas, a complicated life story into 300 pages with clear takeaways.

• 48:09David Senra?

  Deal is how the best founders turn the world into their talent pool. I've been studying how history's greatest founders operate for a decade. And one thing they all have in common is they understand that recruiting and hiring the very best talent is your most important priority. A players recognize other A players, which is why top companies like Ramp, Shopify, 11 Labs, Uber and DoorDash all use Deal. Many of the top founders I know have personally invested in Deal after using their product. And what they discovered is that Deal is the best company in the world at building infrastructure for global hiring. Deal will help your business hire, pay and manage any worker anywhere in the world so you can retain the best talent anywhere and spend the rest of your time focusing on what you do best, delivering value to your Customers, the founder of Eleven Labs has a great description of the value Deal can

• 48:54David Senra?

  give your company. He said, "We built Eleven Labs to break down language and communication barriers. With Deal enabling us to hire and support exceptional talent anywhere, we can accelerate our innovation and bring more voices, stories, and ideas to every corner of the world." Deal is trusted by over 40,000 businesses. Learn how they can help your business today by going to deal.com/cenra. That is deal.com/cenra. Jared keeps hounding me to do an episode of Founders on the book Essentialism.

• 49:24Speaker 01

  Yeah.

• 49:24David Senra?

  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.

• 49:33Speaker 01

  Yep.

• 49:33David Senra?

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

• 49:36Speaker 01

  Yeah.

• 49:36David Senra?

  Because our mutual friend Rick Uerson 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 25 years. And he's just like, I would, I didn't know anything. I was in my early twenties 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 Zell would look at it. He's like, there's one.

• 49:54Speaker 01

  Yeah.

• 49:54David Senra?

  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 Prissler.

• 50:01Speaker 01

  Yeah.

• 50:02David Senra?

  Which was 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 twenties. Like, 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 one. You have one problem here to solve and the rest.

• 50:13Speaker 01

  The best leaders, the best entrepreneurs, they can see clearly. They can find the signal in the noise. I think about it almost like the golden thread. There's one thread you can pull and 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, for your spouse, for, 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

• 50:56Speaker 01

  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 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 fundamentally, that's what entrepreneurship is.

• 51:37David Senra?

  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.

• 51:47Speaker 01

  Not pain, just challenge. Right? Like intensity, growth. These were amazing life lessons. Like, we went to DC 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 third year versus the first or the fourth year versus the second was a different game.

• 52:21David Senra?

  What was the feeling when it ended? Relief?

• 52:26Speaker 01

  For me, this had not been my life plan.

• 52:28David Senra?

  Yeah.

• 52:28Speaker 01

  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, they, once you're close 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 serve, 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, I choose like workforce development,

• 53:10Speaker 01

  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. Forty 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 championed

• 53:49Speaker 01

  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. 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,

• 54:34Speaker 01

  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,

• 55:15Speaker 01

  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 that need this healthy and nutritious produce and that has tons of environmental externalities associated with that amount of waste.

• 55:54David Senra?

  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?

• 56:00Speaker 01

  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 compromised. 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.

• 56:43Speaker 01

  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'd know where to sell your produce into. And so you'd till it into the ground. As part of COVID and as part of the CARE Act, I created something called the Farm Roast, a family 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 job of the distributors who would transport

• 57:24Speaker 01

  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.

• 58:09Speaker 01

  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 ice cream.

• 58:45David Senra?

  Why do they put it back into the earth?

• 58:47Speaker 01

  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.

• 58:54David Senra?

  Okay.

• 58:54Speaker 01

  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. 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. 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

• 59:39Speaker 01

  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 for and and super beneficial for for these farmers who have a very tough job to begin with. So the incremental revenue to them is is 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.

• 1:00:25Speaker 01

  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? Forty percent 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 will scale in a very, very meaningful way while doing a lot of good. You know, on the other side, I'm working on incubating a bunch of non-for-profits.

• 1:01:06Speaker 01

  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 Gil.

• 1:01:15David Senra?

  Yep.

• 1:01:16Speaker 01

  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 forest, 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 and 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.

• 1:02:01Speaker 01

  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 Epertitus. 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?

• 1:02:44Speaker 01

  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 Janair for their eighth grade class. Like, there's no reason, if that's in the public domain, they shouldn't be able to have access to it in a beautiful, accessible way.

• 1:03:26Speaker 01

  And some of this stuff you can find online, but it's not for consumption.

• 1:03:31David Senra?

  No, I go to these websites. Obviously, I'm obsessed, I read more than almost everybody else. So I go to these websites too, and the format's terrible.

• 1:03:37Speaker 01

  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's 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 a lot. Where I'm like, what are you most excited about that's not being done?

• 1:04:21Speaker 01

  And he told me, he's like, there are so many unbelievable works by the greatest. Thinkers humanities 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.

• 1:04:36David Senra?

  Yeah, anything I can do to help on that project. Obviously, you know, it's like 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 was like, this happened three, five year periods ago.

• 1:05:06Speaker 01

  Yeah.

• 1:05:07David Senra?

  Like, that's a funny way to say 15.

• 1:05:09Speaker 01

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

• 1:05:10David Senra?

  Yeah.

• 1:05:11Speaker 01

  But now the large language models are so good. And generative AI is really allowing us to do it affordably.

• 1:05:20David Senra?

  The voices.

• 1:05:21Speaker 01

  With high fidelity. The voices are amazing. So 11 Labs is.

• 1:05:25David Senra?

  I was gonna say, have you, have you, have you spent time with Matty?

• 1:05:27Speaker 01

  I have, yeah. He's amazing.

• 1:05:28David Senra?

  Yeah.

• 1:05:29Speaker 01

  So he's helping us with the audio books that will accompany each of these. But it's amazing. And, and, and we are really like working deep into some obscure languages where people really, they don't have access. They, 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, and students go and they pay for it. So, so this to me is just a fun way to, to give back, to share some of the books, obviously,

• 1:06:12Speaker 01

  that have so profoundly influenced me. But to create a holding place for some of this really important information produced by humanity.

• 1:06:23David Senra?

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

• 1:06:31Speaker 01

  We're having fun even like the first, you know, it's really hard to like choose a thousand books.

• 1:06:34David Senra?

  Yeah.

• 1:06:35Speaker 01

  And so people will say, well, you missed this. 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?

• 1:06:48David Senra?

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

• 1:06:50Speaker 01

  Exactly.

• 1:06:51David Senra?

  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, 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.

• 1:07:23Speaker 01

  Yeah.

• 1:07:23David Senra?

  There's no, he doesn't have electricity, for God's sake, because he 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 of these things that impacted me. And I've used my career many decades in the future. And I think you're going to hear a ton of examples like that when you guys do this project as well.

• 1:07:49Speaker 01

  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.

• 1:08:07David Senra?

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

• 1:08:09Speaker 01

  Who?

• 1:08:09David Senra?

  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, huh, maybe I should start reading more autobiographies and biographies. Turns out you can find mentors in historical context.

• 1:08:46Speaker 01

  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.

• 1:08:53David Senra?

  Probably nobody.

• 1:08:54Speaker 01

  Probably nobody.

• 1:08:55David Senra?

  Yeah.

• 1:08:56Speaker 01

  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. Yeah, exactly. And I think that work is more important than that work.

• 1:09:39Speaker 01

  So, or you'll have people, you know, on the flight, 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, 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 whatever he's doing. He's not always physically present, but he's always available emotionally, telephonically. He'll drop anything he's doing.

• 1:10:20Speaker 01

  Like he somehow has the ability to always be in the right place regardless of, of what he's juggling. 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 notice, actually, you've seen, you have one with him and, 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

• 1:11:05Speaker 01

  he is. And he's very comfortable with himself. He's just very comfortable being exactly who he is and very not 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 gonna have to, I'm gonna have to pull back. Can we edit this whole second out? Because I'm gonna 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. Like, 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 like say, okay, well, that's warranted and like recalibrate.

• 1:11:49Speaker 01

  But it's just not gonna, you know, he cares about the opinions of those he loves.

• 1:11:54David Senra?

  Well, we don't have to edit it because I, as you just said, I spend 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 gonna go back and obviously tell you or anything like that. And we've had a lot of dinners talking about this. So you guys-

• 1:12:07Speaker 01

  By the way, key to life, right? Marry the right person.

• 1:12:09David Senra?

  Yeah.

• 1:12:09Speaker 01

  Marry someone who sees you as, puts you up on a pedestal and sees you as-

• 1:12:16David Senra?

  I don't think I've ever-

• 1:12:17Speaker 01

  In a way that I, he sees me in a way that like I aspire to see myself.

• 1:12:22David Senra?

  This is very rare, what 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 spouses, you know, almost perfect in their eyes, 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 we mentioned, you mentioned essentialism?

• 1:12:44Speaker 01

  Yeah.

• 1:12:45David Senra?

  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 in, with them. Or I may want to partner with somebody on this project, like Planet Harvest, in the profit domain or nonprofit domain like you did with Elad.

• 1:13:10Speaker 01

  Yeah.

• 1:13:10David Senra?

  How are you making this decision?

• 1:13:12Speaker 01

  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, you know, 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, even the scope and scale and ambition of Cezanne, this incredible project, will have hotels and resorts and wellness, all of it, is, it's almost daunting in its size.

• 1:13:46David Senra?

  And an apartment for me.

• 1:13:47Speaker 01

  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 and keeping it, and creating an enabling environment for exactly that. But, anyway. But I think, for me, it's, 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, and what about this?

• 1:14:32Speaker 01

  What about that? I'm like, 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 any challenge I'm about to take on, I become like a PhD in that subject. So with the, with the Cezanne project, I'm reading all the best Albanian writers, and I'm trying to understand the country through their eyes.

• 1:14:55David Senra?

  Oh, it's spark.

• 1:14:56Speaker 01

  And fiction, nonfiction, all of it. And you immerse yourself in sort of the experience, the lived experience of these great observers of, 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, and meaningful way. But that's, that's the approach I take to everything. So I, I listen to a lot of people, I try to surround myself with people that help. Facilitate growth in in different areas. I ask them a lot of questions. I actually tell my kids. They they laugh at me.

• 1:15:40Speaker 01

  In addition to what we were saying before about reading all the time and 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 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 gonna sort of open channels for me and help me grow. And 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.

• 1:16:19David Senra?

  But how do you decide who to let in? Like, what is, what kind of person do they have to be?

• 1:16:23Speaker 01

  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.

• 1:16:41David Senra?

  That's a buffet of anger. They say it over and over again.

• 1:16:43Speaker 01

  No contract, baby. But 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 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 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.

• 1:17:23Speaker 01

  Like, I listen to a ton of podcasts, yours being my favorite, obviously, obviously, on on a variety of 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.

• 1:18:08Speaker 01

  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 to them?

• 1:18:35David Senra?

  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 Zemiri, or no, The Fish Ate the Whale.

• 1:18:44Speaker 01

  I heard your episode on that.

• 1:18:45David Senra?

  Yeah, Sam Zemiri. I forgot the subtitle, but it's about this biography of Sam Zemiri.

• 1:18:49Speaker 01

  We're working with Chiquita Banana now, which is like the largest and helping them think about their access and utilizing it. And I shared that episode.

• 1:18:57David Senra?

  Well, he did something very similar where there's a line in that 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'm, that I thought of when I hear you talk about Planet Harvest, like, he saw opportunity where others saw nothing.

• 1:19:18Speaker 01

  Yeah.

• 1:19:18David Senra?

  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. And in your case, you said that, you know, they just did it this way because it's the way it's always been done. So if you just go into a new situation with fresh eyes and just 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.

• 1:19:37Speaker 01

  100%. And like, that's the best answer in the world. Because that means like, there's ready for disruption.

• 1:19:43David Senra?

  There's innovation that you can do there.

• 1:19:44Speaker 01

  And I think that's what's so cool about doing the, 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

• 1:20:28Speaker 01

  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 boring things. I like investing in things that have the ability to be transformational.

• 1:21:10Speaker 01

  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.

• 1:21:34David Senra?

  And I think you're perfectly suited, it's your personality, to be a champion for these new but fragile ideas. The reoccurring theme in all these biographies that I've read, the 400-plus biographies of business 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. 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 analogy of like an acorn turning into an oak tree.

• 1:22:01Speaker 01

  Yeah.

• 1:22:01David Senra?

  That does not happen in a week, does not happen in a year. It's going to be a multiple-year process that we have to understand that going into it.

• 1:22:08Speaker 01

  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. Yeah. You know, these, so there's a certain sort of neurological flexibility, you know, that, that these founders have, that they can be so passionate about something, yet pivot it into something else they're equally passionate about,

• 1:22:52Speaker 01

  that becomes the ultimate manifestation of that original acorn.

• 1:22:57David Senra?

  And I think your life, what you've shared 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 you a friend. Thank you very much, Emeka, for taking the time. This was absolutely perfect.

• 1:23:08Speaker 01

  Thank you.

• 1:23:08David Senra?

  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.