Tag: Charitable Giving
Advanced Charitable Giving Strategies for Wealthy Families with Frank D. Paolini (Ep. 18)

Advanced Charitable Giving Strategies for Wealthy Families with Frank D. Paolini (Ep. 18)

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Should you use a donor-advised fund or a private foundation? How can you give appreciated stock more tax efficiently while creating a lasting family legacy? As charitable planning becomes more sophisticated, choosing the right strategy starts with understanding your goals, not just the available tools.

Samuel Diarbakerly is joined by Frank D. Paolini, Partner in the Private Wealth Group at Neil Gerber & Eisenberg, for a practical conversation about advanced charitable giving strategies for wealthy families. Together, they explain the differences between donor-advised funds, private foundations, and charitable trusts, how highly appreciated stock and estate tax planning influence giving decisions, and why financial advisors, attorneys, and CPAs should work together to build a charitable plan that reflects your family’s long-term goals and values.

What to expect:

  • How to choose between a donor-advised fund and a private foundation
  • When charitable trusts like CRATs, CRUTs, CLATs, and TCLATs may fit your family’s goals
  • How highly appreciated stock and estate tax planning can influence charitable giving
  • Why coordinated planning between your financial advisor, CPA, and attorney matters
  • How philanthropy can help build a lasting family legacy across generations
  • And more!

Connect with Sam Diarbakerly: 

Connect with Frank D. Paolini:

About our Guest:

Frank D. Paolini is a Partner in the Private Wealth Group at Neil Gerber & Eisenberg. He works with ultra-high-net-worth families, family offices, business owners, and advisors on complex estate, charitable, and tax planning, as well as multi-generational wealth strategies.

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How to Manage a Concentrated Stock Position Without Losing Your Edge (Ep. 8)

How to Manage a Concentrated Stock Position Without Losing Your Edge (Ep. 8)

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Concentrated stock positions can supercharge wealth creation or quietly threaten it. Rex and Sam break down the proven strategies that help you diversify smartly and protect your financial plan.

In this episode of the G360 Wealth Podcast, hosts Rex Berger and Samuel Diarbakerly unpack one of the most common and complex challenges for corporate executives and high-net-worth families: managing a concentrated stock position. Sam shares how these positions form, the risks they create, and the smart, tax-efficient strategies clients can use to diversify without losing hard-earned gains.

Through real-world examples and expert insights, Rex and Sam explore techniques like direct indexing, hedging, exchange funds, and charitable gifting to help listeners turn a concentrated holding into a more balanced and resilient portfolio. It’s an essential guide for anyone with significant equity exposure who wants to de-risk strategically and preserve long-term wealth.

What to expect:

  • The biggest risks of holding a concentrated stock position
  • How to diversify tax-efficiently using direct indexing and hedging
  • When exchange funds or charitable giving strategies make sense
  • Why planning first (before selling) can protect more than returns
  • And more!

Resources:

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Connect with Rex Berger: 

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Charitable Giving with a Plan: Smarter Giving Strategies for Investors and Business Owners (Ep. 6)

Charitable Giving with a Plan: Smarter Giving Strategies for Investors and Business Owners (Ep. 6)

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Giving Smarter: Real Strategies for Tax-Efficient Philanthropy

If you’re donating cash to charity, you might be missing out on major tax benefits.

In this episode of the G360 Wealth Podcast, Sam Diarbakerly sits down with Kyle Casserino of Fidelity Charitable to talk about a smarter way to give: donor-advised funds. These accounts let you make a charitable contribution, get an immediate tax deduction, and give to your favorite nonprofits over time, all while avoiding capital gains on appreciated assets.

Kyle breaks down how donor-advised funds actually work, why cash isn’t always the best gift, and how to think about giving if you’re a business owner, crypto investor, or just want a simpler way to support the causes you care about.

What to expect:

  • How donor-advised funds give you flexibility and control
  • Why donating stock or private business shares might save you more
  • Tools that make giving as easy as sending money on your phone
  • A behind-the-scenes look at Fidelity’s Private Donor Group for larger gifts

This conversation is about giving with intention, and with less friction.

Resources:

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Connect with Kyle Casserino:

About Our Guest:

Kyle Casserino is a Vice President and Planning Consultant at Fidelity Charitable. With more than a decade of experience, he helps advisors and donors use charitable tools to align their giving with their goals—whether it’s a one-time gift or a legacy plan.

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