Bootstrapping your way to the top is a myth

Americans love stories of self-made people who pulled themselves up by their bootstraps. But many successful people actually had a head start

Credit: Nathan Dumlao and Unsplash

Have you ever looked out at the world and wondered why people who don’t seem very different from you are wildly more successful?

This happened to me often when I was in my twenties. I was proud of clawing my way into an entry level job at a small local newspaper, but baffled that people my own age somehow already had book deals and big houses and a menagerie of friends in high places.

Some of those people were just very good at what they do. They pulled themselves up by the bootstraps¹.

But I’ve been surprised to learn over the years how many people actually get a head start. Despite the popularity of the bootstrapping myth, many successful people lean on their family’s intergenerational wealth, connections, or both. And while everyone probably knows this is true of the rich and famous, intergenerational advantages are an important factor even for achieving a middle class life.

The rich and famous often get a head start

Let’s look first at some of the biggest names in tech, where the bootstrapping idea is especially popular. As this useful Twitter thread pointed out, there’s a tendency to romanticize the founding of tech companies, so it sounds like a lowly guy (it’s almost always a man in these stories) has a flash of genius while working in his garage.

But that’s rarely accurate. As that thread points out, Bill Gates succeeded early on, for example, because his mom — the president of United Way — helped Microsoft get a contract with IBM. Mark Zuckerberg went to a private high school that costs almost $60,000 a year, and had private tech tutoring to boot. Jeff Bezos’ parents gave him hundreds of thousands of dollars² to prop up Amazon in the company’s early days.

When you look at a list of the richest people in the world, these kinds of stories are extremely common. Warren Buffet is the son of a congressman. Elon Musk is the son of a professional model and wealthy engineer. Several of the richest people in the US are second generation members of the Walton family, which owns Walmart.

There are analogous examples in other industries. For instance, in Hollywood the Coppola family includes not only famed director Francis Ford Coppola and daughter Sofia Coppola, but also Nicolas Cage and Jason Schwartzman. And Francis himself was the son of a musician who also worked in the entertainment industry.

I’ve tried to find data on how many famous actors come from famous, rich, or well-connected families. I haven’t found anything definitive, probably because “fame” and “good connections” are hard to quantify.

But the list of people in show business who come from show business families is long: Jennifer Aniston, Drew Barrymore, Alexander Skarsgård, Kate Hudson, Gwyneth Paltrow, Angelina Jolie, Charlie Sheen, Carrie Fisher and many others³. The Fonda, Sutherland, and Howard families have been in the business for multiple generations. And sometimes there’s crossover between different industries; tech billionaire Larry Ellison is the father of Meg Ellison, a prominent Hollywood producer. Actor-director Olivia Wilde comes from a family of prominent journalists.

Speaking of journalism, CNN’s Chris Cuomo is the brother of (now embattled) New York Gov. Andrew Cuomo, both of whom are the sons of a prior New York governor. Anderson Cooper is a member of the Vanderbilt family.

None of this is to disparage what these public figures have accomplished. They may have had a head start, but not everyone with famous relatives became Jennifer Aniston. Not everyone who had private tutoring founded Facebook.

The point, rather, is that we love the stories of scrappy and bootstrapping individualists but perhaps under-appreciate how many success stories begin with family connections and advantages.

Financial head starts are important, and increasingly common, even among the middle class

I’ve been citing examples of actors and tech moguls because they’re the easiest to see, but intergenerational opportunity isn’t just for the rich and famous.

For example, in 2018 researchers at Harvard found that parents reduce the barriers to homeownership by simply giving their kids cash to help with their down payments⁴. A 2017 paper further found that homeownership is one of the most important ways people build intergenerational wealth⁵. And recent research seems to indicate that it’s becoming more and more common for would-be homeowners to receive financial assistance from their families when cobbling together a down payment⁶ ⁷.

All of which is to say, people who get a financial head start from their families have an advantage even when it comes to achieving basic middle class milestones like buying a house. Intergenerational opportunity isn’t always measured in the billions of dollars. Sometimes it’s just a few grand.

One response to this reality is to try to dismantle it. If they work correctly, things like wealth and estate taxes potentially chip away at entrenched power. And there’s no question we need to address structural inequality that disproportionately benefits privileged white Americans while leaving everyone else behind. If bootstrapping is a myth generally, that’s especially true for members of communities that have historically (and continue to) experience discrimination. Let’s change that.

But I also don’t think you’re ever going to completely eliminate advantages for families that work together over multiple generations. Most of the people I mentioned above benefited from family networks, rather than cash handouts (though I’m sure some got those too). How do you tax or regulate that?

Researchers have additionally found that acquiring knowledge, as well as lifestyle choices such as getting an education or delaying having kids, can be more important to building wealth than inheritances or cash gifts⁸. And even when very wealthy people give away their money, their family members still have invaluable connections. Warren Buffet’s kids may not inherit his billions⁹ but they’ll still inherit a vast network of opportunity that will give them a head start toward making their own billions.

So what are we supposed to do about all of this?

The bootstrappring myth and the concept of the nuclear family go hand in hand. They both center on the idea that individuals are responsible for their own success. Each generation starts anew. In my world, many people I’ve known see being “self-made” as somehow living the most virtuous life.

But as I’ve argued in previous posts, the nuclear family is poorly serving us at this point. And the idea of being self-made starts to crumble when you look at how much assistance many successful people have. These concepts are melting down.

I think a better approach is to abandon these myths and adopt an intergenerational mindset¹⁰. Parents already save, for example, to help their kids go to college. But with childcare and homeownership increasingly out of reach for many, and with wages in a multi-decade decline, more parents probably need to think more deeply about what role they’ll play in their kids’ lives over a longer term. I’ll delve more into how I think about this in my own life in a future post, but in short family may need to play an increasingly prominent role in career development, childrearing, and housing decisions.

Many people already have this attitude. But it’s also rare in some circles, and cuts against the individualistic ethos we Americans love so much. The problem with holding onto that ethos, though, is that it means you’re unwittingly competing against people who were on third base while you were still sitting in the dugout.

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1. Here’s a little history on the origin of the phrase “pull yourself up by the bootstraps.”

2. “Jeff Bezos got his parents to invest nearly $250,000 in Amazon in 1995 — they might be worth $30 billion today.” CNBC. Zameena Mejia. Aug 2 2018.

3. I’ve seen this kind of thing play out first hand. When I was in my 20s I played in several bands that were part of the same music scene as pre-fame Imagine Dragons. Imagine Dragons at that time was a talented group, but so were a lot of other bands in that scene. So why did Imagine Dragons end up making it while so many others didn’t? Well, it probably didn’t hurt that the lead singer’s brother manages The Killers.

4. “How many young homebuyers get support from their parents and how much of a difference does that make?” Hyojung Lee. Nov. 28, 2018

5. “Generations of Advantage. Multigenerational Correlations in Family Wealth.” Soc Forces. 2018 Jun; 96(4): 1411–1442. Fabian T. Pfeffer and Alexandra Killewald.

6. “Here’s how many millennials got money from their parents to buy their homes.” Emmie Martin. CNBC. March 12, 2019.

7. “Ugh, I can't afford this house: First-time homebuyers get help with down payments from family and friends.” Paul Davidson. USA Today. Feb. 3, 2021.

8. “The lasting effect of intergenerational wealth transfers: Human capital, family formation, and wealth.” Social Science Research. 68 (2017) 1e14. Richard A. Benton and Lisa A. Keister.

9. “7 billionaires who won’t leave their fortunes to their kids.” CNBC.

10. There have been a number of pieces in recent years in the New York Times, Huffington Post and other publications arguing against the boostrapping idea. Many of these pieces are descriptive, arguing (as I have here) that the idea of being self-made is often a myth. But my hope here is to over time work out some other, more effective framework. I see that framework as hinging on an intergenerational, rather than nuclear, approach to family.