A collage of two men shaking hands over the background of money.


The Self-Made Billionaire Is a Myth

When Americans like Kylie Jenner and Jeff Bezos downplay their advantages—and the media follows suit—it prevents us from dealing with the truth about income inequality, opportunity access, and classism.

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In the past few months Twitter has been abuzz with debates over what does and doesn’t constitute being “self-made.” Can you really call Jeff Bezos “self-made” when his parents gave him $300,000 to start Amazon? And how could Kylie Jenner, who grew up on a reality-TV show, in a wealthy family, possibly be considered self-made just because she thought it might be cool to have a line of lip-plumping glosses? Her sister claims that she and her siblings are all “self-made,” in fact, because they’ve never depended on their parents financially. It’s hard to believe that baby Kim was paying for her own diapers, but I digress.

What these debates miss is that behind all of these self-proclaimed bootstrapped billionaires is not just their parents’ cash but also the soft assets, or what sociologists call “social capital,” that come along with being raised in and around wealth.

America’s 242-year boner for the self-made man makes most Americans today—men and women—slow to see or acknowledge any amount of, oh God here it comes, the p-word: privilege. Even people who might roll their eyes at the idea of a “meritocracy” in America are often slow to divulge that their parents gave them money for a down payment on a house, or paid their college tuition, or helped float their business when they were starting out. If they won’t admit that a bit of free money helped them out, they sure as hell aren’t going to acknowledge the more qualitative benefits of growing up in a particular class. That doesn’t mean it doesn’t matter. And in fact ignoring its value is directly harmful to those without these assets because it feeds into the idea that each individual is 100 percent directly responsible for their own success. It also makes it easy to justify not funding social programs that aim to close the wealth gap because hey, if class doesn’t matter, no one needs or deserves help. 

“The advantages of social class and social advantage that are traditionally discussed in sociology are things like being able to be articulate, to have a background of real-world knowledge that seems impressive, to be sensitive to the demands of hierarchy, those kinds of things, which we also like to think just go along with the advantages of good parenting, going to good schools, and more generally the advantages that multiply the advantages of birth,” explains Lee Ross, a professor of social psychology at Stanford University.

Ross’s research has been the inspiration for many a Malcolm Gladwell book, and he talks about how his own kids benefitted from these sorts of soft assets too. “We’re often unaware of the role that being in the right place at the right time confers,” Ross says. “This is particularly relevant to Silicon Valley. It’s an enormous advantage to have grown up—as my kids did— around people who are talking that talk and walking that walk.”

Because his kids grew up in Palo Alto in the 1970s and ’80s, Ross says, and were able to meet his students and colleagues who were getting into tech, they learned about the industry during its formative years, were able to score valuable internships and, most importantly, grocked early on how tech companies worked and what they valued.

Meeting certain types of people or having particular sorts of summer jobs available to you is the sort of thing that we Americans often brush aside as no big deal. But it’s exactly these sorts of things that tend to compound both the advantages and the disadvantages we’re born with. “I remember once sharing with someone that I felt embarrassed that, as a college student paying my own way, I’d worked at a restaurant chain that demeans women,” says Sarah Smarsh, journalist and author of the memoir Heartland. “He said, ‘If your dad had been an attorney, you would have worked in his office for the summer.’ In other words, it wasn’t something about me that led to an unfortunate job but something about my situation. The most under-acknowledged soft asset in professional realms is your own family’s socioeconomic station. That is the foundation from which we arise in a country of nuclear households, without much sense of the village. For members of the middle and upper classes, their politics, networks, choice of college, savings funds and even choice of industry probably have a lot to do with who raised them.”

According to Ross, many people do acknowledge how the lack of certain soft assets affect those not born with them. “We, interestingly, are sometimes sensitive to the fact that other people seem to lack them and be at a disadvantage and we may even make allowances for it,” he says. “But typically we don’t fully appreciate how much we’re at an advantage and we therefore tend to take a little more credit for our success and self-presentation. Most people will say ‘I was lucky, I had great parents or great teachers and mentors,’ but maybe not, ‘Oh, I was very fortunate because I had the opportunity to see my parents interact with very important people, and in seeing how they responded to both subordinates and higher-ups, I learned a lot. That’s not something you’d think about.”

It’s what social psychologist Tom Gilovich describes as the “headwinds-tailwinds bias.” In a nutshell: “Headwinds” are those things that make it difficult for us or others to get ahead, and “tailwinds” make it easier to make progress toward goals—we are pretty aware of and sensitive to the winds blowing in our face (headwinds), but not so much to the winds at our backs (tailwinds).

In the U.S., because of the constant downplaying of social capital, we often don’t even see the lack of it as a headwind for ourselves. I have a friend, for example, who grew up fairly poor, a fact that reveals itself when she mispronounces words like “cortado” or “caprese.” As a smart, hardworking person and a quick learner, she’s managed to do well in her career but only to a certain point. When the promotions stopped coming, she suspected gender discrimination, but it may very well be classism at work.

“I suspect classism is one of the most under-acknowledged -isms in workplaces,” says Antonio García Martínez, a former Goldman Sachs and then Facebook staffer-turned-columnist at Wired and author of the best-selling Silicon Valley expose Chaos Monkeys. Martinez grew up in an upper middle-class family, but says that as immigrants and baby boomers his Cuban parents didn’t necessarily see the changes happening in the country as he was coming of age. “They were raised in the Midwest in Eisenhower’s America, total solid Midwest values, which gel pretty well with Cuban bourgeois values, so within one leap they made the transition to the U.S.,” he says. “But then they sort of got stuck in that version of America, which by the time I was leaving home just was not the way things were any more.”

While different parents might have encouraged their high-achieving son to go to an Ivy League school or head west to Stanford, Martinez’s parents shepherded him toward the path they had both taken: a good, solid, Midwestern state school. “I basically went to grad school at Berkeley and Stanford to make up for this modest undergrad that didn’t fit with the expectation in tech at the time,” he says. But that also delayed his entry to the tech industry significantly, so by the time he started working, his peers had nearly a decade on him. “The amount of wealth and income lost, due to my and my parents’ cluelessness, that’s the key thing,” he says. “If you’re with the elite, even if you’re not in the economic elite, but if you’re raised in those values and surrounded by those people, then, you know, humans are herd animals. If that herd happens to go from Stanford straight into the product manager program at Google, that’s what you do. There are a lot of people who were just on the assembly line from Stanford to Google to some little startup they sold for $50 million and that’s it. That track was just laid out for them, they just got on the treadmill and went down the assembly line and I don’t think most people understand how that works.”

Did that kid who went to Stanford and then on to Google and a startup bust his or her ass in high school? Probably. Did they work long hours at Google? Almost definitely. Does that mean they were “self-made” or that they shouldn’t help pay it forward to someone without the opportunities they were born with? Duh, no.

Being “with the elite”—or not—is also something that is often determined by race. “I remember thinking it was really unfair that some neighborhoods had the nice schools and good restaurants and others didn’t, and realizing there was a racist component to that as a kid,” Randi Pink, a fifth-generation Birmingham, Alabama, resident tells me. “But I always had this attitude line ‘that’s just how it is,’ and I even thought for a long time that my grandparents chose to live where they did because they just wanted to be with other Black people. I was so dumb to think that.”

Pink has spent the past year researching the impact of redlining in Birmingham, from lasting segregation to the emergence of food deserts in predominantly Black neighborhoods (which you’ll hear more about later this year in DAME’s podcast The 51). “It’s not just ‘how it is’ or because of where people chose to live,” she says. “It was designed that way.”

Centuries of institutional racism have kept African-American and Latinx communities from attaining anywhere near the wealth of white families. According to the U.S. Census Bureau, Black families earn $57.30 for every $100 earned by white families. For every $100 in white family wealth, Black families have accrued just $5.04.

That disparity is about more than just money, it equates to a whole different set of connections, networks, exposure to various things, access to certain types of jobs, the list goes on. The continued ignorance—or willful lack of awareness—of that fact leads to the persistence of the meritocracy myth in the U.S., the idea that with the right mix of talent and hard work, anyone can accomplish anything, that we all have equal access to opportunities. Martinez jokes that Silicon Valley is more of a “mediocrity” than a meritocracy. “They use meritocracy as the story to cover the ugliness of the fact that there’s actually not a lot of merit there,” he says. “If you took one of these Stanford treadmill people and stuck them into a ghetto in Richmond or whatever, they’re not gonna end up as a product manager at Google, no they’re not. Who are they kidding? Of course not!”

But, he says, that doesn’t stop many in the tech world from feeling like they deserve their lot in life. “This class has created and perfected the art of failing up. It’s obviously a mediocrity, but you talk to these people and it requires this almost evangelical faith that they are a part of the firmament and the universe has conspired to configure itself in such a way to keep them in Peninsula real estate and Whole Foods their whole lives. Like that’s just the way the world works.”

That lack of awareness often also leads to another extremely valuable soft asset: confidence. “I think the most important thing is for a founder to be confident in general,” says Maxine Kozler, co-managing director of LDR Venture Partners. “Confidence that they belong in that room, that they are creating something wonderful, that they are giving the investors an opportunity to get in on something great.”

Kozler helps coach founders from diverse backgrounds to gain that confidence, that comfort “in the room” with VCs and other potential investors, so it is something that can be learned, with the right mentor.

Arlan Hamilton, founder of venture fund Backstage Capital, says “blinding confidence” is the number-one advantage that people born into a wealthy family tend to come into tech, and that few see how advantageous it is. “Money is the principal, and confidence is the dividend,” she says. “Those in tech who didn’t grow up with wealth walk into rooms at a disadvantage. As a tech outsider originally, I was able to see this very quickly. So I’ve been siphoning this confidence for the past three years, and using it for something I call Augmented Privilege (AP).”

There are hidden advantages to being born with fewer assets, too, which is something Hamilton’s firm specifically focuses on, looking for what she calls “underestimated founders.” Hamilton’s journey, and her approach to investing, are the subject of season seven of the Startup podcast, but the Cliff’s Notes version is that she went from being homeless to starting a venture fund in a few years—she really is the self-made success that Forbes‘ proclaimed Jenner to be, and she believes she got there utilizing the grit and hustle and skills she learned as an underestimated founder herself. Her business edge, then, is to invest in the underestimated, because they’re bound to make your money go twice as far.

Smarsh, too, says that the grit and determination she needed to create a career in journalism is a big part of how she’s succeeded. “When I left home for college and the profession world, I didn’t realize the extent to which connections, family, and the class tiers of social structure affect who receives opportunities,” she says. “I spent my twenties working myself ragged to make up the difference, and that often paid off; my résumé and skills were excellent, and I did manage to break into professional spaces usually inaccessible to people with my background. I could fixate on what I didn’t get along the way due to my being a socioeconomic outsider, whether it’s award nominations or invitations to whisper networks like the “Shitty Media Men” list. But in most cases I don’t think those omissions are intentional or malicious—they’re just a symptom of my occupying a different circle than the one where that stuff is handed out. When I look at the many years I spent having my work rejected, the main difference between me and others with similar goals is perhaps that I kept going. If the publishing or media world told me “no,” I didn’t save the rejection or look back at it once. I kept going, until after many years the no turned into a yes.”

None of which is to say that “hard work” is something only the working class does, either. As one Silicon Valley investor who asked to remain anonymous put it to me, “A lot of progressives talk about privilege as ‘not earning what you have.’ But this conflicts with experiences like mine where you did work really hard and most wealthy people you know also worked really hard (on the road constantly, nights/weekend, stress, etc.) ,” he says. “Yes there are trust funders. And granted there are lots of parents working two jobs with more stress and more hours than anyone should work. But there are also a lot of working class people who work a straight 40 hours per week, nine-to-five, Monday-to-Friday in a pretty low-stress job. They have different stresses of course. But there is a disconnect when we talk about ‘working hard’ in this country.”

Ultimately it’s not an either-or formula. “It is about the scope of the reward, the advantages you had to get that reward (ability to take risk, connections, and so forth) as well as what kind of societal opportunities you want to create,” the investor tells me. “But telling people ‘you are privileged’ can get translated to ‘you don’t/didn’t work hard’ which is usually neither true nor the point, and just makes people defensive.”

It’s not just the assets you’re born with or just the work you put in that determine any one person’s success, but a complex mix of both those factors and a whole bunch of others that—and here’s the part we may hate the most as Americans—are beyond our control; things like the year you’re born, or the particular location. Perhaps if we could dig into the details of the “privilege” debate, have that conversation with some nuance, we might just get more people to see some of their tailwinds and encourage them to shepherd someone else through a particularly strong headwind.

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