Sitting on Highly Appreciated Stock? How a Charitable Remainder Trust Works (with Dr. Roger Silk)
Holding highly appreciated stock, crypto, real estate or a business interest? A charitable remainder trust (CRT) can help you diversify, defer capital gains taxes and maximize income for your family, even if giving isn't your main goal. Jennifer Dazols, CFP®, founder of Modern Family Finance, sits down with Dr. Roger Silk, founder and CEO of Sterling Foundation Management. Roger has been helping families at the intersection of wealth and philanthropy since 1998. They cover how CRTs work, who they're a good fit for, when to start planning around an IPO or acquisition, and what happens if your life changes after you fund the trust. In this episode: The biggest misconception about charitable remainder trusts How a CRT lets you sell low-basis stock without an immediate capital gains bill A $10 million example comparing selling outright with selling inside a trust How much income you can take out, and how to set the payout Minimum amounts for public stock, private businesses and real estate Planning for pre-IPO stock and why timing matters What to do if you need the money later Chapters 0:00 Intro 1:30 What Sterling Foundation Management does 3:50 How Roger got into philanthropy and private foundations 5:00 Who charitable giving tools are for 7:00 The tax problem with low-basis stock in California 9:30 How a charitable remainder trust works 13:30 A $10M example: trust vs. selling outright 20:00 How much income can you take from a CRT? 23:30 Balancing payout, deferral and family goals 26:30 Who is a good fit for a CRT 30:30 Pre-IPO stock: when to start planning 33:00 Do CRTs help with RSU or compensation income? 34:00 The biggest misconception about CRTs 35:30 Risks, regrets and how to get money out 37:30 How CRT assets are invested 40:30 Next steps and how to reach Roger Resources Modern Family Finance: https://www.modernfamilyfinance.com/ Sterling Foundation Management: https://www.sterlingfoundations.com Subscribe for more conversations on money, career and life for modern families.
