In this episode of Money to Give, Rick Peck welcomes back Randy Fox, founder of Two Hawks Family Office Services and a nationally recognized expert in charitable estate and trust planning. Together, they unpack a highly sophisticated yet underutilized planning strategy — the Balloon Charitable Lead Annuity Trust (CLAT), also known as the Shark Fin CLAT. Randy explains how this specialized trust structure reverses the more familiar charitable remainder trust model — allowing donors to give income to charity for a set period, while the remaining assets eventually pass to family members. He demystifies how the balloon structure works, why it can be paired effectively with life insurance, and how it offers both income tax deductions and long-term family benefits. With clarity and humor, Randy walks through examples showing how donors can turn liquidity events — such as a business sale or large stock payout — into meaningful charitable impact while transferring wealth to the next generation tax-efficiently. Rick and Randy also explore why CLATs, despite their power and flexibility, remain so underutilized, and how greater awareness among advisors could change that. The conversation explores: What a Charitable Lead Annuity Trust (CLAT) is — and how it differs from a charitable remainder trust How “Balloon” or “Shark Fin” CLATs work, with charitable payments deferred until later years How CLATs can offset large income events and generate 100% charitable income tax deductions Why CLATs are ideal for high-income individuals, business owners, or families experiencing liquidity events About the Guest Randy Fox is the founder of Two Hawks Family Office Services, a leading advisory firm specializing in advanced estate, tax, and charitable planning. With nearly four decades of experience, Randy is widely respected for helping families and philanthropists transform complex financial strategies into vehicles for purpose and legacy. His expertise bridges the gap between wealth transfer and philanthropy, making him a trusted educator and innovator in the field. 📧 Contact Randy: randy@twohawksfos.com 🌐 Learn more: www.twoharksfos.com Key Takeaways A Balloon or Shark Fin CLAT allows donors to defer charitable payments, enabling assets to grow and maximize both tax savings and family legacy. These trusts can generate substantial income tax deductions — often up to 100% of the contribution amount — while keeping assets working for both charity and heirs. CLATs are most effective for donors with major income or liquidity events, such as a business sale or large bonus. Proper structuring, timing, and appraisals are essential — these complex tools require experienced advisors to ensure compliance. CLATs are powerful yet underused; as Randy notes, they deserve far greater attention from advisors and philanthropically minded clients alike. Subscribe to the Charitable Giving News for You newsletter for more stories, resources, and tips: Subscribe to Charitable Giving News for You.