Modern Family Finance Podcast

Jennifer Dazols

Welcome to the Modern Family Finance podcast, hosted by Jennifer Dazols, a CERTIFIED FINANCIAL PLANNER™. On this show, Jenni invites guests to share their wisdom on finances, careers, and life. She focuses on the specific challenges and opportunities that Women and LGBTQ individuals encounter in today’s ever-changing landscape. Whether you're managing your career, starting a business, or preparing for retirement, Jennifer's guests offer practical advice and support. Tune in for insightful conversations that feel like chatting with trusted friends. More at www.ModernFamilyFinance.com

  1. Sep 29

    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 trustsHow a CRT lets you sell low-basis stock without an immediate capital gains billA $10 million example comparing selling outright with selling inside a trustHow much income you can take out, and how to set the payoutMinimum amounts for public stock, private businesses and real estatePlanning for pre-IPO stock and why timing mattersWhat 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.

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About

Welcome to the Modern Family Finance podcast, hosted by Jennifer Dazols, a CERTIFIED FINANCIAL PLANNER™. On this show, Jenni invites guests to share their wisdom on finances, careers, and life. She focuses on the specific challenges and opportunities that Women and LGBTQ individuals encounter in today’s ever-changing landscape. Whether you're managing your career, starting a business, or preparing for retirement, Jennifer's guests offer practical advice and support. Tune in for insightful conversations that feel like chatting with trusted friends. More at www.ModernFamilyFinance.com