Most generous people give the same way every year: they write a check. In a recent episode of Mark Perlberg's show, Phoenix Hafen, Director of Advisor Solutions at UI Charitable, made the case that a check is often the most expensive way to give.
Mark works with high-income earners who already give to their churches and communities. He invited Phoenix to walk his audience through donor-advised funds from the ground up, and the conversation covered everything from appreciated stock to business sales to a rundown school building.
About the Show
Mark Perlberg is a CPA and the founder of Prosperl CPA, a firm focused on advanced tax reduction for high-income earners, business owners, and real estate investors. On his YouTube channel, he sits down with specialists to break down strategies his clients can put to work. His guiding idea came up more than once in this episode: the best way to lower a tax bill is to start with something you already want to do, then find the incentive that lines up with it.
Episode Highlights
Phoenix described UI Charitable as a philanthropic back office for donors and financial advisors, built around two questions: Are you reaching the charitable outcomes you care about, and are you giving in the most tax-efficient way? From there, the conversation covered:
Why cash is the least tax-efficient gift. Phoenix used a simple example. Stock bought at $100 and now worth $200 can go into a donor-advised fund for a $200 deduction, with no capital gains tax when it sells inside the fund. Selling it first and giving the cash leaves less for both the donor and the charity.
A school building turned community center. One donor wanted to restore a rundown school building in his town. Instead of selling about $1 million in securities and paying the capital gains, he bought the building from his donor-advised fund, where the sale created no tax liability.
Charitable bunching. A couple who gives $20,000 a year to their church may never get past the standard deduction. By putting five years of giving, $100,000, into a donor-advised fund in one year, they can itemize that year and still grant $20,000 a year to the church.
Giving before a business sale. Phoenix spends much of the year with owners preparing to sell. Donating part of the business to a donor-advised fund before the sale avoids capital gains on that portion and offsets income in a high-income year.
Clearing hard-to-sell assets. One donor gave greenhouses he could not find a buyer for. Another gave venture fund interests he doubted he could sell at their appraised value. Both took the deduction and let the fund handle the sale.
Fiscal sponsorship. For people who want to do charitable work themselves, Phoenix explained how they can run a program under UI Charitable's existing 501(c)(3) and start raising tax-deductible donations right away, instead of waiting six months to a year for their own status.
Key Takeaways
Decide what to give, then look at your balance sheet. Once you know the dollar amount, your most appreciated assets are usually the best candidates to give.
Separate the deduction from the decision. A donor-advised fund lets you take the deduction in the year it helps most and choose your charities over time. Meanwhile, the balance can be invested and grow tax-free.
Timing matters. A high-income year, an upcoming business sale, or a pattern of steady annual giving are all reasons to plan a gift ahead of time.
Think about all three parts of a fund. Phoenix described three areas to plan: what goes in, how it is invested while it waits (including impact-focused options), and which organizations receive grants.
Why It Matters
This conversation reflects how UI Charitable works every day. We help donors and their advisors give more effectively, so more of each gift reaches the causes they care about. Whether it is a family tithing to their church, a founder preparing to sell, or someone ready to launch their own charitable program, the goal stays the same: more generosity, structured well.
Listen and Learn More
Watch the full episode: If You Give to Charity You Need to Know This Tax Strategy
Learn more about Mark Perlberg: ProsperlCPA.com
Learn more about UI Charitable or schedule a call: uicharitable.org/learnmore
