Charitable Investing: How To Compound Your Generosity Without The Grief And Grift
Americans gave $617 billion last year to a system only 18.3% of us trust.
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Dear Friend, Subscriber, and Category Pirate,
This mini-book is for three types of people.
If there’s an American baby in your life, there is a $1,000 bill right in front to pick up.
If you want to get started in generosity, keep reading for ten simple ways to start.
If generosity is already who you are, read this to make your giving compound.
This is a shorter mini-book, pirate.
To make it faster for you to get to the Buried Treasure.
The Case for Generosity
Generosity feels great.
Right?
Some of you are nodding your head, as this is a core belief of your identity and what you practice regularly. You’ve seen your generosity have a positive impact and bless many people. And you want to keep giving.
But some of you are shaking your head as you feel the pressure to provide for yourself and your family with limited resources. You’d love to give more, but it makes sense to deal with debt and build up your safe and smart investments first.
And sadly. Some of you still bear scars of generosity gone bad. Maybe a well-intentioned gift backfired. Maybe a gift came with strings attached. Or maybe over the last few years you discovered that some international NGOs (Doctors Without Borders, we’re talking to you) you’ve supported for years is more ‘suss’ than previously thought (as the kids say).
Generosity is legendary, in the right context, for the right people at the right time.
What if we told you it wasn’t about generous or selfish people?
What if current charity doesn’t work because of a fundamental category flaw?
What if charity avoided waste, unintended consequences, and corruption?
What if Category Design could fix it?
Imagine a world where generosity felt less risky and exponentially more good. Where everyone experiences the blessing of giving and receiving.
We call it Charitable Investing. It is exponentially more exciting, enduring, efficient, and radically different than Charitable Giving.
Hey Ho, Let’s Go.
What You Get When You Give
Giving feels good.
Everybody knows that. What most people do not know is how much of it science has actually measured. The reward is real and it shows up in the brain, your mood and even your bloodstream.
Your Brain Likes Giving
Put someone in an fMRI scanner and move their money to a food bank, and the brain’s reward circuitry lights up.
Not the part of the brain that handles duty. Not the part that handles obligation. The reward system.
The same circuitry that responds to food and to money coming in. And when the person chooses to give rather than being made to, the response gets stronger.
Your brain experiences giving as a gain.
Researchers have run this experiment many times over. Hand people money. Tell one group to spend it on themselves. Tell the other to spend it on someone else. Ask everyone at the end of the day how they feel.
The people who spent it on someone else came out happier.
The effect is modest, but it keeps holding up. Spending on other people does more for you than spending on yourself. Think about how much of the economy is built on the opposite assumption.
Your Blood Pressure Likes Giving
In 2016, researchers took seventy-three older adults who had been diagnosed with high blood pressure. They randomly assigned them to spend money on other people or on themselves.
The group giving to others finished with lower systolic and diastolic blood pressure than the group spending on themselves.
The researchers put the size of that effect in the same range as blood pressure medication or exercise.
Your Body Likes Giving
The University of Michigan went into the Wisconsin Longitudinal Study found that regular volunteers had a significantly lower mortality rate than non-volunteers.
However, this longevity boost occurred only for those who volunteered out of genuine compassion for others. Those volunteering for self-serving reasons saw no survival advantage. Ultimately, the body’s protective, stress-buffering biological response is triggered by true empathy.
What Must Be True to Feel the Benefit of Giving
The research is clear that the reward arrives under three conditions.
Choose it. Voluntary giving produces a stronger response than obligated giving. Write the check because you want to, not because someone put you on a list. (This is why you feel angry paying taxes and feel great helping your niece buy her first car.)
Connect to it. The reward is bigger when there is a human being on the other end of it. Give to people, not to abstractions.
See it land. In one study, participants who gave to a cause that showed them exactly what their money bought got happier the more they gave. Participants who gave to a large, general fund got no measurable lift at all.
If you cannot see what your money did, your brain cannot pay you for it.
We were taught that giving is something you do for other people, and that the personal cost is what makes it noble.
The evidence says otherwise.
Giving is one of the highest return uses of a dollar you will ever find. It moves your mood. It moves your blood pressure. It moves your years.
The generous were never sacrificing.
They were compounding.
The Fundamental Flaws of Charitable Giving
Americans gave approximately $617 billion in 2025 to US charities.
This is more than the GDP of most countries. In high-tax nations across Europe and Asia, the government is the sole provider of social welfare, and citizens outsource their compassion to the state.
The US did something different. By combining an aggressive tax-deductible framework with deep-seated traditions of giving, we created a brand new category: Incentivized Private Philanthropy.
Sadly, both systems to move money to those who need it are deeply flawed.
The government’s bucket leaks like crazy.
The Justice Department’s 2025 National Health Care Fraud Takedown charged 324 defendants with $14.6 billion in intended losses, the largest such action in its history. The 2026 takedown charged 455 more.
CMS estimates $3.5 billion in hospice and home care fraud in Los Angeles County. In Minnesota, claims to a Medicaid autism program grew from $600,000 in 2018 to more than $400 million by 2025.
They are programs we fund specifically to care for the elderly, the sick, and the disabled.
Private philanthropy sucks money in, but doesn’t dole out much.
Donor advised funds held $326 billion in assets in 2024 and took in nearly $90 billion more that year.
The donor claims the tax deduction the moment the money goes in. There is no legal requirement that it ever comes out. Average payout runs around 24% a year, which sounds fine until you notice that a meaningful share of accounts distribute nothing at all while the sponsor collects fees on the balance.
Private foundations at least have a rule.
They must pay out 5% of assets annually. The Institute for Policy Studies found that among the 144 US private foundations with endowments over $1 billion, the median payout rate was 5.1%. Private foundations are hoarding charity so they can grow.
Then there are the middlemen.
The Tampa Bay Times and the Center for Investigative Reporting spent a year auditing professional fundraisers and found the worst charities in America were paying solicitors more than 90 cents of every dollar raised. Kids Wish Network collected roughly $128 million over a decade and sent about $110 million of it to fundraisers. Around 2.5% reached a child.
This is why 18.3% of Americans say they have high trust in the charitable sector.
Read that twice. We gave a record $617 billion to a system we openly do not believe in.
None of these were bad donors. Every one of them was bad Category Design.
Kind of makes you feel like this.
The Church is a Paradox of Giving
The church is both the worst and best example of charity and giving.
The Catholic church sits on the world’s most idle real estate and also built the world’s most enduring way of helping and healing billions. It’s the same church with the same balance sheet, but two radically different outcomes.
Did you know the Catholic Church owns more land than the size of Texas?
The Catholic Church owns about 277,000 square miles of land. The estimated value of the land is $350 billion dollars.
Much of the $350 billion dollars of real estate is largely used one day out of a week.
We’re not saying this is all a waste. We are saying let’s confront the structural design flaws that create waste. And apply Category Design to re-invent a new form of charity that is more powerful and productive.
Does it seem like fantasy land that the Catholic church could do this? Nope. We just need to go back to the future.
The Catholic church helped create the category of modern hospital as we know it.
In about 370 AD, the Catholic church created St. Basil the Great’s hospital complex near Caesarea. It was so vast that contemporaries called it a “new city.” It had isolation units for lepers, housing for the poor and elderly, and systematic care on a scale never seen before.
St. Benedict said, “the care of the sick is to be placed above and before every other duty, as if indeed Christ were being directly served by waiting on them.”
Today the Catholic Church manages 5,377 hospitals, 13,895 outpatient clinics/dispensaries, and a total of 103,951 health, charity, and assistance institutions worldwide (including homes for the elderly and disabled, orphanages, and nurseries).
It is estimated that the Catholic church represents 26% of the world’s healthcare facilities. In the US, one in seven patients are seen in a Catholic hospital.
If hospitals were purely a charity, they would not have enough money to endure. If hospitals were purely a business, the mission of saving lives would miss the mark. Hospitals aren’t perfect, but imagine a world without any hospitals or modern healthcare.
Charity plus capitalism is what has helped the category called Hospitals endure for centuries.
A New Law Changed the Category of Giving
In July 2025, Congress passed the One Big Beautiful Bill Act. Buried inside it were two changes that almost nobody has connected.
The first change made donating money worth less.
Starting in 2026, if you itemize your taxes, the first half-percent of your income no longer counts as a deduction. Make $400,000 and your first $2,000 of donations gets you nothing back. Separately, the highest earners now get capped at a 35% benefit instead of 37%, so a $10,000 gift that used to save $3,700 in taxes now saves $3,500.
Small numbers. Clear direction. Washington just made the old category slightly less rewarding.
The second change created something that didn’t exist before: a tax-advantaged investment account for every American child, that anyone can contribute to.
One law. It made Charitable Giving a little worse and made Charitable Investing possible. We don’t think anyone planned it that way. We think it’s the most useful accident in the history of American philanthropy.
Charitable Investing is Legendary
There are two obvious ways to help people who need it.
Give them a fish. Or teach them to fish.
The first way doesn’t last past the first fish. The second way still requires giving time and requires mastery to keep getting fish.
The third non-obvious way is to give someone stock in a fishing company, that compounds over time and grows. While you sleep. So you can buy the fish you want for yourself and others, possibly into perpetuity.
That is Charitable Investing.
A genuinely new category that came to life on July 4th 2026.
530A accounts. Originally conceived as Invest America accounts by Brad Gerstner of Altimeter Capital.
Every American child born between 2025 and 2028 receives a $1,000 government seed contribution invested in a broad market index fund. Families can add up to $5,000 a year. The money is structured like an IRA for a minor, so the child takes control at 18 under retirement account rules.
And for the first time in American history any person can make a direct tax advantaged gift into a capital account for any American child.
Direct. Person to person. Into an ownership account that compounds for 18 years.
Pirate Christopher and his wife are shifting 50% of their giving to direct charitable investing.
The Five Conditions Where Charitable Investing Works.
Charitable Investing looks most promising where these five conditions are present.