Success isn’t a substitute for giving. 91% of ultra wealthy households used to donate to charity, but now only 81% do. I sat down with David Roberts to address the causes and consequences of declining philanthropy. Even in an age of tremendous wealthy accumulation, modern titans of industry seem to have traded the moral weight of their ancestors for the hollow vanity of the Forbes 400. Ultimately, the path forward requires dismantling the legal loopholes that prioritize the few over the many to ensure the American dream remains more than just a relic of the past.
My recent article, Why Philanthropy is Silent in the Golden Age of Wealth
David’s recent article, A Man Who Dies Rich Dies In Disgrace
Transcription summary from NotebookLM.
0:00 - The Death of Duty
We have traded the moral weight of the first Gilded Age for a secular scorecard where wealth is the only metric that matters. Unlike Carnegie or Rockefeller, today’s titans lack the religious fervor that once commanded them to give back or face the flames of judgment. In our modern metric-oriented society, billionaires watch their ranking on the Forbes 400 like authors obsessing over subscriber counts. Wealth has become an end in itself, stripped of the historic expectation that the ultra-rich must serve as moral role models. To whom much is given, it seems, nothing is currently expected.
3:00 - Marketplaces Aren’t Miracles
Building a global marketplace or launching rockets to Mars should never be a hall pass for avoiding philanthropy. While we can applaud entrepreneurial brilliance, we must ask why that success is not twinned with behavior that serves the public good. Being a single-minded entrepreneur is one thing, but it does not automatically make someone a compass for the next generation. Wealth should not just be about personal “looks maxing” or individual attributes; it requires a sense of responsibility to the human family. True leadership demands more than just a massive payroll—it requires a soul.
4:45 - The Personal Math of Justice
Tracking your spending is not just about financial planning; it is a reflection of your values and your vision for the world. For every $2.50 spent on family, there should be a dollar dedicated to repairing the fraying edges of our society. Giving is not merely a transaction of cash; it is an investment of time, networks, and the skills built over a lifetime. This is not just charity; it is a pursuit of justice that connects us to our ancestors and our future grandchildren. When you back grassroots leaders at a local food pantry, you are not just giving money—you are fueling a more hopeful future.
11:00 - The Philanthropy Power Trap
We have entered a dangerous era where billionaires get to play God with global health and social priorities. While eradicating malaria is a triumph, the public never voted for it, and we should not rely on the whims of the ultra-wealthy to fix our world. Government triumphs like PEPFAR prove that stable, elected institutions can save millions without waiting for a donor’s permission. When the social safety net is left to private “pet causes,” we risk leaving massive holes where public funding once stood. Philanthropy is a powerful tool, but it should never be a replacement for a functioning, accountable democracy.
15:00 - Closing the Billionaire Loophole
To save the social safety net, we must dismantle the legal loopholes that allow extreme wealth to remain untaxed across generations. It is time to tax capital gains at the same rate as the hard-earned wages of every other American. Ending the “stepped-up basis” ensures that massive fortunes finally contribute to the country that made their accumulation possible. We need a federal tax system that prioritizes the many over the few to avoid a fiscal catastrophe. Paying taxes is the ultimate incentive for a society that wants to see every citizen succeed.
Question for the comments: What are some of the most frustrating parts about how government operationalizes the social safety net or nonprofits execute their missions? Is the tax system incentivizing the right actions?





