Jackpot

1. The American Dream is the Jackpot Fantasy.

We dream of being whisked from the toil of the rat race into a socioeconomic realm that will end our daily grind, solve our most pressing problems, and mark the start of a fabulous new adventure.

The collective fantasy. The notion of striking it rich, the "jackpot," is deeply ingrained in the American psyche, dating back to the first colonists searching for gold. This dream persists, with over four out of five college students rating "being very well off financially" as essential or very important.

• $81 billion spent on lottery tickets in 2019 (more than the GDPs of two-thirds of nations).
• More than ten times the amount spent on books.

A desperate hope. In an era of increasing inequality, the wealth fantasy is tinged with desperation. It promises freedom from debt, limits, bosses, and deadlines, offering a seemingly blissful escape from the daily grind and financial stress that burdens most Americans.

Unforeseen complications. However, this fantasy rarely includes contemplating the social, psychological, and societal complications that come with great affluence. Wealth can be a Pandora's box, bringing unexpected sorrows, strained relationships, and a sense of disconnection from others.

2. Hitting the Jackpot brings unexpected complications and anxieties.

Anyone who hits the jackpot will quickly discover that necessity is straightforward, but choices are complicated.

Sudden wealth shock. For those who experience a sudden windfall, like Netscape employees becoming "Mozillionaires" or lottery winners, the initial euphoria is often quickly replaced by anxiety and bewilderment. Managing incomprehensible wealth is stressful.

• Netscape employees didn't know what to do with their sudden millions.
• A lottery winner with $104 million after taxes was "freaked out."

Social disruption. New wealth alters social dynamics, attracting opportunists and creating rifts with old friends and family members who may feel resentful or entitled. Even simple acts of generosity can cause unexpected pain.

Existential crisis. When financial necessity is removed, many struggle with a loss of purpose and identity. The question of "What do I do now?" becomes profoundly difficult, leading some to feel lost or unmoored without the structure and motivation of needing to work.

3. Superlative wealth requires a dedicated "entourage" and becomes a job.

Great wealth is a job no matter what you do with it.

A demanding child. Managing extreme wealth is a full-time responsibility, akin to parenting a demanding child. It requires constant attention, nurturing, and worrying, consuming significant time and emotional energy.

• Yachts, properties, and investments require upkeep and management.
• Tax season becomes exceedingly complicated.

The entourage. Wealthy individuals delegate responsibilities to an entourage of professionals: lawyers, accountants, money managers, and family office staff. However, oversight is crucial to prevent mismanagement or theft.

• One lottery lawyer was indicted for allegedly defrauding clients.
• An estate lawyer noted clients often struggle to admit their net worth.

Emotional toll. Dealing with wealth triggers complex emotions like guilt, responsibility, and self-consciousness. The pressure to manage it properly, coupled with the difficulty of discussing finances openly, leads many to rely on their paid entourage for emotional support, blurring professional boundaries.

4. Money buys access and exclusivity, creating bubbles and isolation.

Most of all, it enables the twin obsessions of the superwealthy: privacy and exclusivity.

Beyond the velvet rope. Vast sums of money open doors to exclusive experiences, prominent people, and exotic places, enabling the wealthy to separate themselves from the general population. This is signaled through luxury goods and services.

• $1,500 cocktails, $500 sneakers, $12,000 suits.
• Bespoke items designed for specific clients.

Luxury segregation. High-end real estate in exclusive zip codes like Atherton, California, offers privacy and security, often featuring gates and lush screening to keep neighbors at bay. Absentee ownership is common, leading to a lack of community.

• Median home price in Atherton exceeded $7 million.
• Many homes have alarms connected directly to police.

The bubble effect. Living in affluent enclaves can lead to losing touch with how normal people live, creating a sense of estrangement and making it difficult to relate to those with different financial realities. This isolation can foster distrust and a "them vs. us" mentality.

5. Wealth influences values and behavior, often negatively.

Money throws gas on your values.

Extrinsic pursuits. Wealth often fuels a focus on extrinsic values like material possessions, social status, and financial success, which research links to lower life satisfaction, increased anxiety, depression, and poorer relationships compared to intrinsic values like community and meaningful relationships.

• Wealthy individuals are more likely to exhibit entitlement and narcissistic behavior.
• Higher social class predicts increased unethical behavior in experiments.

Less compassion. Studies suggest wealthier individuals are less attuned to social context and exhibit less compassion for the suffering of others compared to those with fewer resources. This correlates with a reduced willingness to help strangers.

Justifying inequality. Successful people, regardless of their actual advantages, tend to attribute their success to hard work and merit, while viewing less fortunate people as deserving of their lack of success. This mindset helps justify economic inequality and makes it seem equitable.

6. Wealth perpetuates itself through systems favoring the rich (taxes, inheritance, access).

The snow ball will grow as it rolls.

Rigged game. The economic system is rigged to favor those who already have wealth, making it easier for them to accumulate more. This is evident in tax policies, access to capital, and inheritance laws.

• The wealthiest 1% own 56% of all equities.
• Tax policies favor investment gains over wages.

Tax avoidance. Wealthy individuals and families employ sophisticated strategies and expensive professionals to minimize their tax burden, often paying a lower effective tax rate than the middle class.

• Pass-through deductions overwhelmingly benefit the wealthy.
• Carried interest allows fund managers to pay lower capital gains taxes.

Intergenerational transfer. Tax laws, like the estate tax exemption and dynasty trusts, facilitate the transfer of vast fortunes across generations, perpetuating economic aristocracy and compounding advantages for the already rich.

• $68 trillion expected to transfer within 25 years.
• Dynasty trusts can shield assets from inheritance taxes forever.

7. Inequality is systemic, not just about individual effort (race, gender, opportunity).

This is not a talent issue, but an access issue.

Unequal playing field. Despite the myth of meritocracy, systemic barriers based on race, gender, and socioeconomic background create profound opportunity gaps, making it significantly harder for certain groups to accumulate wealth and power.

• Median white household wealth is 10x that of Black households.
• Women hold only 7.4% of Fortune 500 CEO positions.

Historical disadvantages. Policies like slavery, Jim Crow laws, and discriminatory housing practices (redlining) actively suppressed wealth creation for Black Americans and other minorities, while programs like the Homestead Acts disproportionately benefited white families.

• Only 4,000-5,000 Black families received land under Homestead Acts vs. 1.6 million white families.
• Banks refused loans to single women without a male cosigner until 1974.

Ongoing barriers. Even today, disparities persist in access to quality education, capital, and professional networks. Wealthy families can afford advantages like private schools, tutors, and college counselors, while others rely on under-resourced public systems.

• Elite colleges enroll more students from the top 1% than the bottom 50%.
• Legacy admissions favor children of alumni.

8. Philanthropy is complex and often reinforces inequality.

Philanthropy is commendable, but it must not cause the philanthropist to overlook the circumstances of economic injustice which make philanthropy necessary.

Not always selfless. While some wealthy individuals are genuinely altruistic, philanthropy can also serve as a "legitimation project" or "reputation-laundering exercise," distracting from how wealth was acquired or reinforcing the donor's status.

• Sackler family's donations to cultural institutions amid the opioid crisis.
• Walmart's foundation focusing on hunger while paying low wages.

Donor priorities. Wealthy donors often direct their giving towards institutions that benefit themselves or their peers, such as universities, hospitals, and cultural organizations, rather than focusing on basic needs or social change initiatives.

• 60% of "big bets" (>$10M) went to universities, hospitals, and cultural institutions (excluding Gates).
• Few foundations focus on diseases primarily affecting minorities, like sickle cell anemia.

Taxpayer subsidies. Charitable giving is heavily subsidized by taxpayers through deductions and tax-exempt status for foundations and donor-advised funds. This disproportionately benefits the wealthy, who receive larger tax breaks for their donations.

• The federal charitable deduction costs taxpayers over $50 billion/year.
• Wealthy donors receive a larger subsidy per dollar donated than middle-class donors.

9. The wealth gap is widening, creating a precarious society.

The farther apart you stretch a society economically, the farther apart the rungs of the ladders of opportunity are stretched, and the farther one must travel inside that social construct to feel successful.

Exponential growth at the top. Wealth accumulation at the very top of the economic ladder has become exponential, particularly since the 1980s, while wages for the bottom half have stagnated or declined when adjusted for inflation.

• Average wealth of the top 0.01% is over $1.8 billion per adult.
• Average wealth of the bottom 40% is $199 per adult.

Diminished American Dream. Absolute upward mobility (earning more than your parents) is no longer assured for most Americans. The widening gap means fewer people can achieve a middle-class life, leading to profound stress and insecurity.

• Only half of adults born in 1984 earned more than their parents, down from 92% in 1940.
• 165 million Americans live with startlingly little income and declining life expectancy.

Societal breakdown. Extreme inequality erodes social cohesion, breeds distrust, and contributes to political polarization and instability. The concentration of wealth translates into concentrated political power, further entrenching the advantages of the elite.

• Wealthy individuals' policy preferences strongly influence outcomes.
• Wealthy Democrats are less likely to support policies reducing inequality.

10. Changing the system requires acknowledging complicity and sacrificing privilege.

What am I, personally, willing to give up in order to make things better?

Beyond giving back. Simply donating money after accumulating vast wealth is not enough to address systemic inequality. True change requires confronting the policies and practices that create the wealth gap in the first place.

• Tax avoidance and lobbying efforts by the wealthy undermine public good.
• The system is designed to route resources to the top.

Acknowledging complicity. Many wealthy individuals, particularly those from privileged backgrounds, struggle to acknowledge the role of luck and systemic advantages in their success, preferring a narrative of being "self-made." This denial hinders progress.

• Wealthy whites often resist acknowledging their privilege.
• "Self-made" is often a narcissistic conceit that ignores the efforts of others.

Sacrifice is key. Making things better requires those with privilege to sacrifice some of their advantages, whether it's advocating for higher taxes on themselves, supporting campaign finance reform, or giving up exclusive access and opportunities.

• Some wealthy individuals are joining groups advocating for systemic change.
• True freedom comes from shedding the need to hoard wealth and status.

Last updated: May 3, 2025