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Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Pivot · Dec 19, 2025

Pivot's listener mailbag tackles taxing AI, single-policy solutions, personal finance philosophies, parenting after loss, and tour life.

Eliminating Capital Gains Deductions Is a More Effective Tax Strategy Than Targeting AI

Taxing a specific industry like AI is problematic as it invites lobbying and creates definitional ambiguity. A more effective and equitable approach is broad tax reform, such as eliminating the capital gains deduction, to create a fairer system for all income types, regardless of the source industry.

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Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Pivot·2 months ago

Scott Galloway's Wealth Strategy: Match Lavish Spending with Equal Giving to Avoid Hoarding

To combat the 'virus' of wealth hoarding, Professor Scott Galloway intentionally keeps his net worth flat. He implements this by matching his substantial annual personal spending—on homes, travel, and experiences—with an equal amount in charitable donations, viewing money as something to be 'rented' and deployed, not accumulated.

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Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Pivot·2 months ago

Boys in Single-Mother Homes Are More Emotionally Vulnerable and Need Male Mentorship

Scott Galloway asserts that boys are emotionally and neurologically weaker than girls, making the absence of a male role model a critical point of failure. He argues it is especially important for single mothers raising sons to proactively involve positive male figures—like uncles, coaches, or family friends—in their lives for healthy development.

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Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Pivot·2 months ago

A Cynical Real Estate Strategy: Buy Luxury Homes in Elite Enclaves for Future Billionaires

Scott Galloway's real estate strategy is to buy and develop luxury homes in the few global locations favored by the ultra-wealthy (e.g., Aspen, London). His thesis is that worsening income inequality will create thousands of new billionaires—a homogenous group with predictable tastes—ensuring high demand for these specific properties.

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Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Pivot·2 months ago

Overturning Citizens United Solves More Systemic Problems Than Any Single Economic Policy

While economic policies like raising the minimum wage have broad benefits, campaign finance reform like overturning Citizens United is more fundamental. It addresses the root cause of political gridlock and corporate influence, which prevents many other positive social and economic changes from being implemented.

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Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Pivot·2 months ago

Witnessing a Parent's Profligacy Can Foster a Frugal Mindset in Children of Wealth

Kara Swisher explains that despite growing up with money, her mother's excessive spending and resulting financial instability made her frugal. This experience instilled a deep-seated need for financial control and a desire to always 'have enough,' demonstrating how childhood financial trauma can shape habits regardless of actual wealth.

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Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Pivot·2 months ago

Widowed Parents Should Preserve a Deceased Spouse's Memory by Maintaining Their Social Ties

Reflecting on losing her father, Kara Swisher advises that the surviving parent should actively maintain connections with the deceased's family and friends. Her mother failed to do this, forcing Swisher to rediscover her father's history on her own as an adult—a painful process her children could have been spared.

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Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Pivot·2 months ago