In this insightful episode of Money to Give, Rick Peck welcomes back Randy Fox, founder of Two Hawks Family Office Services and a leading voice in charitable estate planning. Together, they explore an often-overlooked concept that can have major implications for business owners and philanthropists alike — personal goodwill. Randy explains the difference between enterprise goodwill (the reputation and systems tied to a business itself) and personal goodwill (the value that comes from an individual’s reputation, relationships, and expertise). He illustrates how, in many closely held businesses, personal goodwill represents an asset of significant — yet frequently unrecognized — value. The conversation dives deep into how identifying and valuing personal goodwill can unlock powerful charitable planning opportunities. Randy and Rick discuss how, by separating this goodwill from other business assets during a sale, owners can potentially avoid capital gains, claim charitable deductions, and even fund tools like donor-advised funds, charitable remainder trusts, or pooled income funds. Throughout the discussion, Randy highlights real-world examples and emphasizes that understanding goodwill isn’t just an accounting concept — it’s a pathway to aligning business success with philanthropic purpose. The conversation explores: The distinction between enterprise goodwill and personal goodwill How business owners can identify and appraise their personal goodwill Why goodwill can be treated as a capital asset — and its tax implications How to donate personal goodwill to charitable vehicles like donor-advised funds, CRTs, or pooled income funds About the Guest Randy Fox is the founder of Two Hawks Family Office Services, a nationally recognized expert in advanced estate, tax, and charitable planning. With nearly four decades of experience, he advises families, entrepreneurs, and philanthropists on how to structure gifts that maximize both impact and efficiency. Randy is known for translating complex financial strategies into meaningful acts of generosity that benefit donors and the causes they care about. Contact Randy:
[email protected] Learn more: www.twohawksfos.com Key Takeaways: Personal goodwill is the value tied to your reputation, relationships, and expertise — and it can often be separated from your business in a sale. This intangible asset can be donated to charitable vehicles to avoid capital gains and create lasting philanthropic impact. Transactions must be carefully structured — ideally before signing a binding letter of intent. Proper valuation is critical; use qualified appraisers familiar with goodwill assessments. Strategic planning can turn business success into ongoing charitable influence while optimizing tax outcomes. Subscribe to the Charitable Giving News for You newsletter for more stories, resources, and tips: Subscribe to Charitable Giving News for You.
