Charitable Planning | Giving With Intention | Intentional LLC

Charitable Planning

The tax benefit is real.
But it is not the
point.

People come to charitable planning from every direction. Some come because a liquidity event created a tax problem worth solving. Some come because something happened that changed how they see the world. All of them leave with more than they came for, if they are open to it.

Start the conversation

The financial tools are straightforward. Finding what you actually want to give toward is the harder work.

Where giving actually comes from

Something has to happen
first. Then the giving
becomes real.

The research on high-net-worth philanthropy consistently shows that personal values are the stated primary driver of charitable giving. The 2025 Bank of America Study of Philanthropy found that 68% of affluent donors cite their personal values and beliefs as the top factor in where they choose to give. 87% say they find giving personally fulfilling.

In practice, the conversation often starts somewhere else. A business sale is coming and the tax bill is significant. Someone mentioned a Donor Advised Fund. They want to understand what is possible before the deal closes. That is a legitimate and common entry point. There is no judgment in it. The tax tools are real and the savings can be substantial.

What I have found, though, is that the people who walk in asking about deductions and walk out having found something they actually care about are the ones whose giving changes them. Not just their tax return. Them. That shift does not happen in every conversation. But when it does, it is the most meaningful work I do.

And on the mechanics: cash is one of the least efficient gifts a high-net-worth individual can make. Appreciated securities, concentrated positions, and sophisticated structures like Charitable Remainder Trusts and Charitable Lead Trusts can accomplish far more for the cause and for the donor simultaneously. Whether you come to this conversation for tax reasons or for personal ones, the strategy deserves to be built around what actually serves both.

"Charitable giving, if done the right way, can impact you more than you can ever impact it."

James Roberts, Founder, Intentional LLC

What the Wealth Identity Assessment reveals about giving

The Wealth Identity Assessment surfaces a great deal about how a person relates to giving before we ever discuss charitable vehicles. A Type 2 may give compulsively and need help distinguishing generosity from self-depletion. A Type 1 may want their giving to be morally pure and need permission to act before they have found the perfect cause. A Type 8 may give fiercely and protectively, building things for the people they love rather than institutions they do not control.

Understanding your type and your pattern around giving changes the charitable planning conversation entirely. It tells us whether you need to be given permission to prioritize yourself first. Whether your giving impulse is connected to something real or something conditioned. Whether the cause you think you want to support is genuinely yours or one you inherited from someone else's expectations.

That is not a soft conversation. It is the most important one we have.

A personal note

The closest feeling I have had
to hitting a big shot.

I grew up playing basketball. There was no better feeling in my life than hitting a huge shot in a packed gym at the most intense moment. The noise, the elation, the joy, the unity of it. I lost my last high school game in an upset to a team we should have beaten. I had not considered anything after basketball. I sat there with tears down my face. I had been the basketball player for as long as I could remember. When that was gone, I did not know who I was without it.

Years later, a close family member was diagnosed with blood cancer. I did not have large financial resources to throw at it. So I dedicated my time, sacrificed my body, and signed up to raise money while competing in a triathlon. I wrote a blog during that training, whatever came to mind, and much of it ended up being a description of how my life was being empowered at a moment when I felt the weakest.

People were moved. They were inspired. And what I felt during that period was the closest thing I have experienced to hitting that shot in a packed gym. That unity. That sense of being part of something larger than myself.

My family member has been cancer free since one month after that diagnosis. And what I learned from that season is something I bring into every charitable planning conversation I have with a client. The financial tools are real. But the feeling of genuinely embracing a cause that is larger than your own needs and your own life, that is not something you can manufacture with a tax strategy. It has to be found. And it is worth finding.

James Roberts, Founder, Intentional LLC

The financial tools

The vehicles that make
giving more effective.

01
Donor Advised Funds

A DAF allows you to make a tax-deductible contribution now and distribute grants to specific charities over time. Particularly powerful in high-income years, including the year of a business sale or liquidity event. You receive the deduction when you fund the DAF, not when the grants are made.

02
Charitable Remainder Trusts

A CRT allows you to contribute appreciated assets, receive an income stream, and have the remainder pass to charity at the end of the trust term. Particularly effective for concentrated positions with a low cost basis. Must be established before a liquidity event closes to be most effective.

03
Gifts of appreciated securities

Contributing appreciated stock or other securities directly to a charity or DAF allows you to avoid capital gains tax on the appreciation while taking a deduction at fair market value. One of the most tax-efficient ways to give, and one of the most underused by people who write checks instead.

04
Private foundations

For clients with significant philanthropic goals and the desire for more control over their giving, a private foundation offers flexibility in how grants are made, the ability to involve family members, and a lasting institutional structure for a family's charitable legacy. Requires more administration than a DAF but offers greater control.

05
Charitable Lead Trusts

A CLT is the inverse of a CRT. The charity receives the income stream for a period of time, and the remainder passes to your heirs at the end of the term. Particularly useful for clients who want to reduce estate taxes while supporting a cause they care about during their lifetime.

06
Qualified Charitable Distributions

For clients over 70 and a half, QCDs allow direct transfers from an IRA to a qualified charity, satisfying required minimum distributions without the transfer being counted as taxable income. A simple and often overlooked tool for clients whose giving strategy has not been integrated with their retirement account planning.

Keep reading

Related topics worth
understanding.

Liquidity Events

What happens before, during, and after the deal closes

Pre-Transaction Planning

The work that has to happen before the letter of intent is signed

Mattering

Why the need to matter shapes every financial decision you make

Common questions

What people ask about
charitable planning.

  • Charitable planning is the process of structuring philanthropic giving in a way that aligns with your financial situation, your tax position, and your values. For high-net-worth individuals, charitable planning often involves vehicles like Donor Advised Funds, Charitable Remainder Trusts, private foundations, or direct gifts of appreciated assets. The financial benefits are real and significant. But the most effective charitable planning starts not with the tax code but with a clear understanding of what the client actually wants their giving to mean.
  • A Donor Advised Fund, or DAF, is a charitable giving account that allows you to make a tax-deductible contribution now and distribute the funds to specific charities over time. You receive the tax deduction in the year of the contribution, even if the grants to charities happen years later. DAFs can accept cash, securities, and in some cases other assets. They are one of the most flexible and tax-efficient charitable giving tools available, and they are particularly valuable in years when income is unusually high, such as the year of a business sale or liquidity event.
  • A Charitable Remainder Trust, or CRT, is an irrevocable trust that allows you to contribute assets, receive an income stream for a period of time, and then have the remaining assets pass to a charity at the end of the trust term. Contributing appreciated assets to a CRT allows you to avoid the immediate capital gains tax that would result from a sale, receive a partial charitable deduction, and generate income. CRTs are particularly effective for concentrated positions with a low cost basis, and they work best when established before a liquidity event closes.
  • Charitable planning can reduce the tax impact of a business sale in several ways. Contributing appreciated shares to a Donor Advised Fund before the sale closes allows you to take a deduction at fair market value while avoiding capital gains tax on the contributed shares. Establishing a Charitable Remainder Trust before the sale can defer and partially reduce capital gains tax while generating income. The key in all cases is that the planning must happen before the deal closes. Once the transaction is final, most of these options are no longer available. Learn more about pre-transaction planning.
  • Giving out of obligation is transactional. It checks a box, reduces a tax bill, or fulfills a social expectation. There is nothing wrong with it. But it rarely produces the feeling people are actually looking for when they give. Giving with intention means connecting your philanthropy to something that genuinely moves you, a cause that emerged from your own experience, a mission that feels personal rather than performed. When that connection is real, giving stops being a line item in a financial plan and becomes one of the most significant sources of meaning in a person's life. Learn more about mattering and why it shapes financial decisions.
  • The best time to establish charitable planning vehicles is before a liquidity event, a large income year, or a significant capital gains realization. Donor Advised Funds can be established relatively quickly and funded before a transaction closes. Charitable Remainder Trusts require more lead time but can be significantly more powerful when set up in advance. If you are thinking about selling your company or expect a large income event in the next one to three years, the conversation about charitable planning should be happening now. Learn more about liquidity event planning.

Start the conversation

The financial tools are
straightforward. Finding what
you want to give toward
is the harder work.

If you are approaching a liquidity event or asking what your wealth is actually for, charitable planning is one of the most meaningful conversations we have. Schedule a conversation with James.

Schedule a conversation

30 minutes. No pitch. No pressure.