Philanthropic giving is an essential component of many of our clients’ long-term financial plans. A well-developed philanthropic strategy involves a great deal of planning; there is upfront work to prioritize specific causes and issues, followed by decisions on optimal giving structures. Finally—in keeping with the topic of this publication—there is the choice of which assets the client will donate. Many of our clients’ first instinct is to make charitable gifts with cash. However, making an in-kind gift of highly appreciated securities can often be a better solution from an income-tax perspective. Structural Options Before discussing the advantages of gifting appreciated securities vs. cash, we should briefly review some of the primary philanthropic structural options. We generally discuss four main giving options with our clients. Direct gifts—in other words, outright donations of cash or other property directly to a charitable organization—are a relatively simple option and very common. When making an outright gift, you are generally entitled to an income tax deduction for the value of the gift (subject to income limitations). Donor advised funds, or DAFs, have become extremely popular, and for good reason. Gifts to a DAF are eligible for an immediate income tax deduction, but charitable distributions out of the account can be made gradually over time—this provides a great deal of flexibility to donors who may wish to deploy charitable assets gradually rather than all at once. Private foundations are a third option. They are particularly good options for families who want to move beyond gifting and become active in a more programmatic manner. When considering private foundations, families should understand the administrative burdens of such structures, as well as the fact that these foundations must distribute at least 5% of their assets annually. In contrast, DAFs do not have an annual distribution requirement; there have been recent conversations in Congress about instituting annual payout requirements for DAFs, but it is far too soon to speculate about whether this will come to pass. Another consideration: If you gift an interest in an operating business to a private foundation, you may face complications later with regard to taxes on income earned by that business. Finally, various trust structures can offer benefits to both the donor and the charitable recipient. Let’s say that you wish to provide an income stream to a charity for a period of time while retaining your principal for yourself or your heirs. You can create a charitable lead trust to accomplish this. Conversely, you may wish to establish an income stream from a pool of capital for yourself during your lifetime, and then bequeath that capital to a charity at your death or at some fixed future date. In this case, you would use a charitable remainder trust. Using these types of structures adds complexity to a philanthropic plan, but trusts can be highly effective for clients who want a synergistic strategy that produces positive outcomes for family and charity at the same time. We often work with clients to help them develop their philanthropic strategy, and, as mentioned previously in this publication, we find that our role in advising clients on both investment and tax matters can be quite helpful. For example, we can effectively address the need to reduce portfolio risk with a set of actions that also achieve desired charitable goals. In some cases, we work alongside the philanthropic advisors of the community foundations and other organizations that our clients wish to support, reviewing the variety of solutions that these organizations offer their donors and choosing the strategies that best fit each client’s goals and circumstances. Gifting Appreciated Assets As noted above, many people primarily think about gifting with cash, but a gift of a low-cost-basis asset can provide tangible benefits to the donor. Consider a donor who purchased stock at $20 that is currently worth $100. If the donor sold that stock, after capital gains taxes, they might have $80 or less to donate to charity. A better solution would be to gift that stock directly. The donor would be eligible for a tax deduction for the full $100 fair-market value of the stock (again, subject to income limitations). The charity could sell the stock for $100 and because it is tax-exempt would not need to pay any capital gains tax, thus benefiting from the full $100 donated. Beyond this basic equation, there are other ways we have helped clients leverage appreciated holdings for charitable purposes. For example, if a client is attached to a family legacy holding that provides a healthy dividend, they might want to place that stock in a private foundation or even a charitable lead trust and direct those dividends to charities of their choice. This would remove the risk of the concentrated position from their personal portfolio while still allowing them to use the position to accomplish philanthropic objectives. It is a privilege to help our clients make an impact in the world. By being thoughtful about each specific step in the philanthropic process, we aim to help them maximize that impact. 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