In Jackson Hole, philanthropy isn’t just something we do—it’s woven into who we are. Teton County, with a population of just 23,000, is home to more than 200 nonprofits. Whether serving lunch at the Senior Center, saving lives with Search and Rescue, or volunteering as a board member, nearly everyone here is rolling up their sleeves and getting involved.

Of course, financial support is the lifeblood of these organizations—and Jackson delivers. Last year, our local 5K, Old Bill’s Fun Run, raised over $23 million. That’s nearly $1,000 for every resident.

As a wealth advisor and an active Board member in the Jackson Hole community, I’m often asked about the most effective—and tax-efficient—ways to give back with greater impact. It’s a high-class problem, but once contributions exceed a few hundred dollars, practical questions emerge: What are the tax implications of different giving methods? Which options offer the most impact for the least complexity or cost?

I created a straightforward starting point to navigate these decisions: a matrix comparing common charitable giving strategies side-by-side. While not comprehensive, examining key factors—tax treatment, cost, and ease of use—can help you identify approaches that might align with your giving goals and values.

Source: Bootpack Financial Partners, LLC

For friends and clients, my go-to recommendation for most gifts over $500 is using a Donor Advised Fund (DAF).

Phil DeMuth's terrific new book, "The Tax-Smart Donor: Optimize Your Lifetime Giving Plan," succinctly describes them: "Donor-advised funds are experts in turning appreciated stock into cash that any charity will be able to digest easily…..DAFs function as a waystation for your charity dollars. In this holding tank, you can park and invest money indefinitely before passing it through to the ultimate destination charities you select."

These accounts combine the immediate tax benefits of charitable giving with the flexibility to distribute funds over time, all while making the asset donation process as straightforward as shopping on Amazon.

Come tax time, a DAF also consolidates your charitable giving into a single year-end tax document, whether you give cash, stock, or other appreciated assets.

In addition, DAFs are particularly valuable for donors who don't typically itemize their tax returns. By 'bunching' multiple years of charitable giving into a single tax year—say, contributing $15,000 to your DAF instead of giving $5,000 annually—you can exceed the standard deduction threshold and itemize that year while still distributing the funds to charities over time. This strategy allows you to maximize your tax benefits without changing your actual giving pattern, essentially getting the best of both worlds: immediate tax savings and flexible distribution timing.

Our family maintains two complementary DAFs. One is a Schwab account for stock transfers and broader investment options. The other is a Community Foundation of Jackson Hole account for longer term planned giving and where the administrative fees support local initiatives. Both charge a reasonable ~0.60% per year for administration and grantmaking.

Here's a real DAF process example: Last quarter, for my annual Board Member contribution to the Grand Teton Music Festival (GTMF), I transferred appreciated Google stock through my Schwab DAF instead of writing a check.

1) I initiated the stock transfer from my brokerage account to my DAF through Schwab Charitable's website.

2) Once the shares arrived in my DAF the next day, I recommended a grant to GTMF.

3) Schwab handled the stock liquidation and sent the funds to GTMF within 5 business days.

The benefits were substantial:

• Avoided capital gains tax on the appreciated stock.

• Received a full market-value tax deduction.

• GTMF received 100% of the proceeds, with no need to handle stock transfers.

• All tax records (cost basis, fair market value, date) are centralized in Schwab’s portal.

For gifts over $500K or complex estate planning needs, strategies like Charitable Remainder Trusts or Private Foundations may offer additional benefits. For most giving situations, DAFs provide the best balance of impact, simplicity, and tax efficiency.

Strategic philanthropy can be straightforward with the right tools and thoughtful planning. Whether you’re considering your first major gift or refining an existing strategy, tools like Donor Advised Funds can help you maximize your impact while remaining aligned with your values.

If you’re curious where to begin, the charitable giving matrix offers a helpful starting point and I'm happy to discuss how these strategies fit your giving goals and financial situation.