Month: September 2025

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)

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:

Connect with Sam Diarbakerly:

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.

The Business Owner’s Edge: Smarter Retirement Planning with Jason Whitney (Ep. 5)

The Business Owner’s Edge: Smarter Retirement Planning with Jason Whitney (Ep. 5)

Most business owners think of retirement plans as something their payroll provider sets up, and that’s where the missed opportunity begins.

In this episode, Sam Diarbakerly talks with Jason Whitney, President of Whitney Pension Associates, about what really goes into building a smart retirement plan and why it matters more than people realize. They walk through how business owners, consultants, and board members can use 401(k)s, profit sharing plans, and cash balance plans not just to save, but to reduce taxes in a big way.

From a family business origin story to six-figure savings examples, Jason explains what a TPA actually does and how the SECURE Act 2.0 is making these strategies more accessible, especially for small businesses.

You’ll hear about:

  • How 1099 income, board pay, and side gigs can be turned into tax-free retirement savings
  • Why coordination between your CPA, advisor, and TPA is key to getting the most from your plan
  • Real client stories, including one who cut a $400K tax bill with the right plan design
  • The important window for setting up a retirement plan that still applies to last year’s taxes

Resources:

Connect with Sam Diarbakerly:

Connect with Jason Whitney:

About Our Guest:

Jason Whitney is the President of Whitney Pension Associates, a second-generation firm focused on retirement plan design. He joined the family business in 2007 after a career pivot that took him from a grad school degree to helping grow the firm’s national reach. Based in Vermont, Jason is also a Corporator for Mascoma Bank and a passionate New England sports fan. When he’s not helping clients with tax strategy, you’ll find him on the golf course, ski slope, or spending time with his wife and three kids.