The Trump Card: Playing to Win in Work and Life

Read an Excerpt

—HENRY FORD

In business, as in life, nothing is ever handed to you.

That might sound like a line coming from someone with a back-story like mine—and a load!—but if you know me and my family, you’ll understand that I come by these words honestly. Yes, I’ve had the great good fortune to be born into a life of wealth and privilege, with a name to match. Yes, I’ve had every opportunity, every advantage. And yes, I’ve chosen to build my career on a foundation built by my father and grandfather, so I can certainly see why an outsider might dismiss my success in our family business as yet another example of nepotism.

But my parents set the bar high for me and my brothers. They gave us a lot, it’s true, but they expected a lot in return. And you can be sure we didn’t rise to our positions in the company by any kind of birthright or foregone conclusion. My father is definitely not the kind of guy who’d place his children in key roles within his organization if he didn’t think we could surpass the expectations he had for us. You see, in the Trump household, it was never just about meeting the expectations of others. It was about exceeding them. It was about surprising people. And being the best. Anything less was second-rate, which probably explains one of my biggest worries starting out—that I would merely be competent at my job in the Trump Organization. Good enough, and nothing more.

I can still remember how anxious I felt, how completely out of my element, when I was appointed to the board of directors of Trump Entertainment Resorts, the parent corporation of our casino operations in Atlantic City. Realize, this was no closely held family business. It was a public company, so there was enormous pressure to prove that I belonged. Some of that pressure was real, and some of it was imagined—but that didn’t make it any less terrifying. I can still remember walking over to my first board meeting at the law offices of Weil, Gotshal & Manges, feeling incredibly nervous the whole way. It was just a five-minute walk, but that was more than enough time to think through every worst-case scenario. It didn’t help that just before I left my office someone pointed out that I was about to become the youngest director on the board of a publicly traded company in the United States; I had enough to worry about already. I was twenty-five years old, just a year or so into my tenure at Trump, about to sit around a conference table with a group of middle-aged men—some of whom, I’m sure, would be wondering what the hell I was doing there. On some level I knew that I’d been tapped to represent the voice of a younger generation and to represent my family’s interests in the company that bore our brand. But on another, I worried that I’d be exposed as a kid in over her head. My formal appointment was still subject to board approval, and I still had to apply for a gaming license and gain other clearances, but I vowed on that uneasy walk that I would never give these people a reason to question the value I brought to the table.

The whole way over to that meeting, it felt to me as if my appointment to the board was stacked all the way against me: I was young and inexperienced; I was a woman; and I was Donald Trump’s daughter. (It might appear as if this last would be a plus, but I didn’t see it counting for a whole lot in my favor; if anything, it might have given the impression that I had been tapped only for some vague public relations value.) Growing up with two brothers, I’d watched enough baseball to know that you get only three strikes, so I might have counted myself out before I even stepped to the plate. But then I realized that what some people might regard as a negative, others might see as a strength. Maybe my relative youth and inexperience would help me offer a fresh take. Maybe the board needed a young woman’s perspective. Maybe the fact that I was Donald Trump’s eyes and ears on the board, as I was at the Trump Organization and on his reality television show, would make me uniquely qualified to offer insights and strategies for positioning the three Trump-branded casinos that were the primary assets of the company.

In any case, it was overwhelming. Intimidating. So how did I handle it? I dug in, breathed deep, and vowed to do whatever it took to show my new colleagues on the board and the company’s management team that I added real value. And merely belonging wouldn’t quite cut it, in my estimation. I was determined to play an integral role. I might be nervous, but I wouldn’t show it. I might be intimidated, but I wouldn’t show it. I might even be a bit overmatched, in my first few meetings, but I’d get up to speed before long. And sure enough, that’s just what happened. By the end of that first meeting, most of my anxieties fell away, and I walked back to my office in Trump Tower feeling as if I had made a contribution, after all. As if I would make an even greater contribution going forward.

Let’s face it, when you come from a place where good enough is not quite good enough, you’re bound to push yourself. You’re disinclined to take anything for granted. And you’re not about to be dismissed just because someone might think you’ve had an unfair advantage. These days, I try not to let it bother me when someone jumps to conclusions about my abilities. I have a tough skin and enough confidence not to worry too much about being underestimated because of my last name, my relative youth, or my modeling background. It comes with the territory. I’ve reached the point where I know I’m no lightweight. I’m perfectly capable of separating my colleagues and associates from this type of snap judgment when it comes up—which happens less and less these days, I’m happy to report.

The message I put out to people who are prepared to write me off before even meeting with me: get over it. It’s the same message I used to give to myself whenever I spent too much time worrying what people would think of me or how I’d risen to my position in the company or what attributes I brought to the table. I’d catch myself agonizing along these lines and think, Just get over it, Ivanka. Or, It’s not your problem, it’s theirs. After all, I eventually realized, we’ve all got our own baggage. Whatever we do, whatever our backgrounds, we’ve all had some kind of advantage somewhere along the way. Some break that might have gone to someone else. Some edge or inside track we couldn’t have counted on.

As long as I’m on that inside track, I might as well work that metaphor a bit more to make my point. That perceived lead I might have had starting out? It’s like the stagger you see in a middle-distance event at a track meet. You know, where the runners line up in a stepping-stone way in their separate lanes, the runner in the outside lane well ahead of the field before the starting gun goes off, the runner in the inside lane well behind. It’s set up that way so that each runner covers the same ground before she reaches the first straightaway, but it has the appearance of being an advantage. In truth, the only advantage is psychological; each runner ends up covering the same ground by the end of the race. With me, it probably looked as if I were in the outside lane, way ahead of the rest of the pack before the race even started. But I still had to run the distance. I still had to go to school, learn the basics, develop my own style, make and support my own decisions, and on and on.

What a lot of people don’t realize is that this all-too-common mis-perception usually runs hand in hand with another. It took me a while to recognize this, but there’s definitely a flip side to how other people might see you, way out there in life’s outer lane with that apparent jump start. On the one hand, you get the idea that my success is purely a by-product of privilege, proximity, or favoritism—or, relatedly, that Donald Trump’s daughter could not possibly have ascended to the role of vice president of his real estate company for any reason but filial devotion. People assume that I’m not smart enough or driven enough or savvy enough to have made it on my own. On the other, it’s just the opposite. People build it up in their heads that just because I’m Donald Trump’s daughter, it must mean I have an inherent understanding of all things related to real estate and finance.

(I guess it could be worse!)

I used to get this a lot when I was at Wharton, as an undergraduate at the University of Pennsylvania, where my classmates would turn to me whenever a professor posted a challenging question. In their minds, because I’d spent so much time with my father and shared the same genes and mind-set, I must know the answer automatically. And truth be told, I still get this kind of deferential treatment. People sometimes approach me tentatively or suspiciously because of my father’s reputation as a world-class negotiator, as if they think I’m about to take advantage of them. As if I know something I’m not letting on. It can be a big disadvantage, especially going into a negotiation, when I’d much rather be underestimated. My brothers tell me that the same thing happens to them all the time, so we just deal with it and move on.

I get it from both sides, the good and the bad. Positive and negative. And I’ve learned to ignore it. To rise above it. I refuse to let the opinions of others define how I see myself, how I carry myself, how I get through my days. It’s just not relevant to me. If I got upset every time someone suggested that I was coasting on my last name, my looks, or the silver spoon that might or might not have been lodged in my mouth at birth, I’d be a basket case. And if I pumped myself up and found an ego shot in every tossed-off bit of undeserved praise, my head would be too big to get through my office door.

And so: get over it. Go ahead and bring it up if you feel you must. Acknowledge the elephant in the room. But then move on. Move on, because I’m way past it. Move on, because even though those who believe that my success is a result of nepotism might be right, they might also be wrong. Try as I may—and try as my critics may—there’s just no way to measure the advantage I’ve gained from having the Trump name, just as there’s no way to know if the person sitting across from you in a job interview or a negotiation is there on his or her own merits or with an assist of one kind or other.

What I do know is this: I’m incredibly and endlessly proud of what my family has accomplished. It starts with my father, I suppose— but then, he’d probably tell you it starts with his father, my grandfather. And there’s also my mother to factor in. She’s played a big role in my development as a businesswoman: her strength, her discipline, her character. (She’d probably put some of that on her parents as well.) My brothers, too, have had a hand in my success, just as I hope I’ve had a hand in theirs. I’ve come to realize that we bring something to one another, so that the whole is greater than the sum of its parts. We’re a wellspring of individual talents and perspectives, and I drink from it all. We drink from it all. So rather than worrying about what other people think or how they calibrate or credit our attributes and achievements, my focus is to ensure that these successes continue for the next generation of Trumps. After all, we Trumps don’t play to perceptions. We play to win.

Gosh, I sound like my father, don’t I? But that’s what you get from this particular Daddy’s girl.

The perceived edge, the stagger, the loaded or backhanded compliments, the unearned deferential treatment—it all takes me in a round-about way to the book you now hold in your hands, a business memoir, shot through with life lessons and hard-won insights for young women looking to jump-start their own careers. Yes, from the pen of a former model. Yes, from an entrepreneur who’s built her reputation on her family name—in the family business, no less. But you can’t judge a book by its cover, right? There’s a reason the phrase has become a cliché: it’s true. Okay, so I’ve had a bit of an edge getting in the door, but that doesn’t mean I haven’t developed an edge of my own now that I’m all the way in the room.

A word, first, on the title: The Trump Card. It’s meant to signal that we’ve all been dealt a winning hand and that it’s up to each of us to play it right and smart. In bridge, of course, the trump card is the one that prevails, no matter what, and as a strategy it’s usually held in reserve for when it’s most needed. I’ve played it here because I like the metaphor and the way it shows how I’ve tried to play my own winning hand.

Lately, I’ve been playing that hand in a family business that would be all but unrecognizable to my grandfather, who started out building and operating affordable rental housing in the New York City boroughs of Brooklyn, Queens, and Staten Island in the 1930s. Now, as executive vice president in the Trump Organization, I’m on the front lines of such seismic change at our company that even I don’t recognize the offices I used to visit every day after school. Already I’ve played an integral role in developing more than seventy real estate projects around the world, including buildings in New York, Chicago, and Dubai. That role has very little to do with who my grandfather was or who my father is and quite a lot to do with what I’ve learned along the way. At one point, I might have been in just a bit over my head and pushed along before I was ready, but now my days are filled with meetings and decisions and prospects. I might talk over a potential branding deal with a developer in Indonesia in the morning and just a few hours later visit a construction site to negotiate price with a concrete contractor from the Bronx. I’ll sit down at a conference table with a group of bankers and lawyers to work out the financing for a new hotel, then return to the same table six months later with a group of architects and interior designers to define what that hotel will actually look like. I once flew to South America to meet with a developer and then spent several tense days negotiating the terms of a partnership relating to a 2.6-million-square-foot property, coming home with a deal my father called one of the best he’d ever seen. Or I’ll work with my jewelry design team to put the finishing touches on a magnificent new collection.

No one day is like another, and they’ve all added up to a wealth of experience. My experience. I’ve been exposed to a level of responsibility that’s very rare for someone my age. My responsibility. While most young people in business spend their twenties enduring the growing pains and lowly paper-pushing assignments that come with earning your stripes, I’ve been able to bypass (mostly) that sort of grunt work and have been part of upper management from very early in my career.

Have I had an advantage? Absolutely. Have I safeguarded the trump card I’ve been dealt in my winning hand for when I needed it the most? Again, absolutely. Does that mean I can’t play that card or build on those advantages and take away some insights and strategies that might help other would-be entrepreneurs from gaining an edge of their own? Absolutely not. In fact, one of the biggest advantages has come in a once-removed sort of way, and I hope to pass it along in these pages. You see, I’ve had tremendous access to some of the most creative, freethinking minds in business—much of it thanks to my parents’ friends and associates. But contacts are only that. A point of connection. A place to start. It’s what you do with those contacts that counts, and here I’ve tried to take what these accomplished people have given—sometimes freely, sometimes grudgingly—and then ask for a little bit more besides. I’ve learned firsthand from some of the most successful people on the planet, in all walks of life.

Over the years, so many remarkable people have taken the time to answer my questions and share their philosophies with me, and not just the boldface, CEO-type names. I’ve learned just as much from equally impressive and influential people who operate under the public radar. I take every opportunity I can to talk with these market leaders, the hardworking, hard-charging people who’ve been over some of the same roads I’m looking to travel, so I can see how their minds work and recognize the traits we have in common as well as where we differ. In the end, it’s what we can glean from our mentors, role models, and fleeting acquaintances that sets us apart.

So I’ll include some of these strategies in these pages, to reinforce the critical point that we learn not just by doing but by listening in on and reaching out to the successful people we meet in our lives, to learn what we can from their struggles and their triumphs. You’ll hear from some of my most influential and innovative friends and contacts in between chapters in segments I’m calling “Bulletins from My BlackBerry,” for the way it reminds us that these points of connection are available to all of us. Hopefully, these shared insights will offer you a feel for what it’s like to be on the receiving end of so many powerful lessons from so many inspiring individuals—and the encouragement and inspiration to access the authoritative viewpoints within reach in your own lives.

The message I take in from the people who inspire me is that success isn’t something that happens to you; you happen to it. Confidence is key, and there was always plenty of that to go around in our house. Forget the silver spoon and the storybook upbringing. This is the single most important asset I’ve inherited from my parents: confidence. (Perseverance runs a close second, by the way.) Without it, I couldn’t work as a developer in a field dominated by older men. And without it, I couldn’t have launched a jewelry business in such an uncertain economic climate.

Did I grow up with every advantage? Well, maybe not every advantage but some. Did I have an edge, getting started in business? No question. But get over it. And read on. Together, we’ll figure out a way to hold onto the trump cards we’ve been dealt until we can put them to the best possible use.

I’m fully aware of the favorable hand I’ve drawn in life. And profoundly grateful for it. I also get that there’s something inherently condescending about any twenty-seven-year-old trying to give people advice—especially this particular twenty-seven-year-old, who still has so much to learn. It doesn’t matter how many deals I’ve done or how many captains of industry I can get to return my phone calls. I’m still just a couple of years out of school, still just a couple of years into my career. But that’s precisely the point. We young guns have a lot to offer one another in a comparing-notes sort of way. When I reach for a book to help me past a hurdle or two in my business life, I don’t go looking for a dry manual written by some sixty-year-old male, reflecting on a long career. I want to hear from someone who still knows what it was like to stay up all night cramming for an exam. Who can still taste the anxiety of speaking up for the first time in a big meeting. Who still gets goose bumps when she opens a box of new business cards after her first promotion. Who finds her way to the office on a Sunday morning after being out half the night dancing with her friends.

Like it or not, that’s me. Believe it or not, that’s me. Despite my title, my pedigree, and my responsibilities, I’m just like any other young woman in the workplace. I question my role in life. I struggle to find the right balance between work and play. I go to the movies or out with my friends, but I also make my work a priority. And even though I think I’m close to getting it right, I’m still searching for a style that’s appropriate for someone in my professional position, a style that expresses my spirit and sass and seriousness all at once. Basically, I’m looking for the same things as a lot of young women just starting out in business—and, trust me, we’re not only deferring to wizened old boardroom veterans for advice on what to wear to work, how to prepare for a key meeting, or when to seize an opportunity. We’re looking to one another, just as we might have reached out to a friend from home who was a year ahead of us at school or an older sister.

Why write a book at all at this stage of my career? One word: television. If I hadn’t joined the cast of my father’s reality show, The Apprentice, we wouldn’t even be having this discussion. The show has been a huge hit, at one point drawing more than 50 million viewers each week. And it’s changed just about everything for me. Despite my very public upbringing, I’d always been a very private person, and up until I joined the show I was able to go about my business and do my thing in a stealthy sort of way. I liked that. Nobody paid much attention to me beyond the transactions themselves. I was able to make my presence known around a conference table or on a construction site, but if we weren’t dealing with each other directly you wouldn’t have recognized me. I was a private person, working out of range of the public eye. Television changed all that, right away. I’m not even the star of the show, just a supporting player, but I started to get tons of mail from viewers, starting with my very first appearance. Reality television is such an intimate genre, people can’t help but see you as you are—and they seemed to respond to me. Now that I was something of a celebrity, they appeared to like that I was cut a little differently than other successful young women of my generation, that I seemed more focused on building a career and making my family proud than on partying and hamming it up in front of the cameras. I heard from mothers, thanking me for setting such a positive example for their daughters. And I heard from those daughters, asking for advice on how to make it in the business world.

I thought that was pretty cool. Unexpected but pretty cool. And the more I thought about it, the more it made sense. After all, my brothers and I were the original “apprentices.” We’d spent most of our lives learning the ins and outs of business from our parents. No, Donald Trump couldn’t fire us—not until we started working for him, at least—but in every other respect it was a full-on apprenticeship.

Millions of people had turned to him for advice and inspiration over the years, so it was inevitable that a new generation of aspiring entrepreneurs would look to us for our own takes on the Trump formula. At first I tried to respond to as many of the letters and e-mails as I could—but ultimately that was impossible. So I approached the situation the same way I would have tackled any other dilemma: I came at it from a new angle. I thought, How can I reach out to all these young women in a more efficient way?

One more word to explain my inspiration to write a book. Actually, one name: Oprah. I’d been invited onto her show to promote my new jewelry line—my first solo venture outside our core family business. I was terrifically excited, because I’d always been a huge Oprah Winfrey fan. During our interview, she complimented me for managing to avoid the traps that ensnare many other children of privilege and for staying focused on making my own mark in the world. It was such an honor to hear her say that. But there was an even bigger thrill. She was wearing a stunning pair of my earrings—O-shaped, of course—from the Ivanka Trump Collection. I’d given them to Oprah as a thank-you gift for having me on the show, but I’d never expected her to wear them while I was on the set. It was such a gracious gesture, I thought.

A few days after the taping, I received a lovely handwritten letter from Oprah, thanking me for the earrings and congratulating me on my various accomplishments. She even called me a role model for the twenty-first-century woman. It was another gracious gesture, but it was more than the letter itself that touched me. It was what Oprah had to say. Her words meant so much that I had the letter framed and keep it on my office desk.

I hope Oprah won’t mind that I’m sharing so much with you, because she’s one of my role models. I think she’s the most influential businesswoman in the world, so I took her words as a kind of charge— to share my own insights and experiences with anyone who cared to sign on for the ride. Therefore, a book: one that I hope can be a resource for young women starting their careers or perhaps looking to rejuvenate them, in today’s incredibly challenging economic environment. And it’s not just the business landscape that’s so challenging for young women. It’s our personal path, as well. There are so many choices out there for us, so many opportunities, so many twists and turns that we can hardly anticipate. It’s all too easy to take one tiny misstep in the wrong direction and end up on a completely wrong road.

And so I set about it.

RUSSELL SIMMONS—Record producer, hip-hop mogul

I talk to a lot to people who are in struggle, a lot of kids who don’t have a lot of faith, and I try to get them to realize that they already have everything they need. Everybody is given everything they need, all the time. We know that because it’s in every scripture. And the real truth is, when you’re comfortable with what you have, you attract other things. Think of the most successful people you know. They go to work, they say they need to work, but they really don’t need anything. That’s why things like them. They attract success. It’s basic: when you go to work from a place of abundance and you operate from a place where you already have everything, you work harder and smarter because your mind is clear and your focus is strong.

So I’m always telling young people to count their blessings. Start from a place of strength. Get up in the morning, and decide what you’re going to give. All that taking stuff is secondary. It’s giving. I mean, you’ve got to give to get, right? Good givers are great getters. That’s the reason you’re here. You need to become a great servant, first and foremost. Everything else will follow. And it’s not as if we have to change the way we are. Most of the young people I work with, they wake up in the morning, they want to be servants. It’s in us already. We want to give something back, put something out there. If you’re a record producer, you come across a hot record, you start to think, Wait till they hear this! You’re not thinking about the money you’ll make, although the money will come. You’re thinking, Wait until they hear this record! You’re excited. You want to share it. If it’s clothing, you’re thinking, Wait till they try on this shirt! It’s hot! Anything creative, it’s like that. Any service.

In business, we should always be looking to give something that brings lasting happiness. Something we believe in. You want to be proud of your product, proud of what you’re giving your customers. That’s what will make your product or service stand out, because people can feel that. Your commitment to excellence, to strength, to purpose, it all shines through. That’s where you find your success.

You don’t trick the world, you feed the world.

© 2009 Ivanka Trump