Category: Financial Education

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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:

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.

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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)

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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.

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Estate Planning Made Simple: Where to Start and Why It Matters (Ep. 4)

Estate Planning Made Simple: Where to Start and Why It Matters (Ep. 4)

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What happens when families avoid the estate planning conversation? 

In this candid and insight-packed episode, host Sam Diarbakerly sits down with estate planning attorney Crosby Elliott to uncover the often-overlooked truth: the greatest gift you can give your loved ones is clarity.

Together, they walk through the emotional, legal, and financial consequences of not having key documents like trusts, healthcare proxies, or powers of attorney in place. From avoiding probate court chaos to navigating guardianship for minor children, Crosby makes a complex topic feel human and manageable, with a touch of humor, too.

Here’s what you can expect from this release:

  • A breakdown of why revocable trusts are often preferable to wills
  • Real-world stories of what can go wrong without a plan
  • Guidance on choosing the right healthcare proxy and guardian
  • A checklist of critical documents to get in place now
  • And more!

Connect with Sam Diarbakerly: 

Connect with Crosby Elliott:

About Our Guest: 

Attorney Crosby Elliott is a partner at the firm and assists individuals and families in all aspects of estate planning and trust and estate administration. Crosby’s experience in both planning and administration allow him to expertly advise clients through their many stages of life. Crosby prides himself on building relationships with clients to help simplify what can often be an overwhelming experience.

Crosby’s practice focuses on how best to minimize or avoid Massachusetts or federal estate taxes, avoid probate, shield assets from the cost of long-term care, and protect assets for beneficiaries. Crosby accomplishes these goals by employing sophisticated and comprehensive estate planning techniques, including the use of revocable trusts and various irrevocable trusts. Crosby also prepares federal gift tax returns.

A significant portion of Crosby’s practice also involves counseling clients through the administration of a loved one’s trust or estate. In doing so, Crosby regularly prepares and files both Massachusetts and federal estate tax returns, petitions with the probate court, and assists in dispute resolution between parties. Crosby also hosts presentations at businesses, organizations, and clubs on the importance of estate planning.

Outside of the office, Crosby enjoys spending time with his family, friends, and his dog. During the non-winter months, Crosby spends his free time either in Kennebunkport, Maine, hiking along the Appalachian Trail, or just generally enjoying the outdoors.

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Unlocking Private Markets with Phil Huber of Cliffwater (Ep. 3)

Unlocking Private Markets with Phil Huber of Cliffwater (Ep. 3)

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Everyone has a private markets fund, what goes into selecting the best managers??

Phil Huber, Head of Portfolio Solutions at Cliffwater, joins the G360 Wealth Podcast to break down how private equity and credit can become practical investments for more than just the ultra-wealthy. 

He explains how interval funds are changing access, structure, and expectations for investors. This episode is a must-listen for anyone who wants to understand the next evolution of portfolio building.

Key Points:

  • How interval funds reduce the barriers to entry for investors with lower net worth by using accredited investor standards instead of qualified purchaser thresholds [00:02:40]
  • The size, structure, and risk profile of the $1.7 trillion direct lending market, and how it offers floating-rate, senior-secured loans with low interest rate exposure [00:08:11]
  • Why private equity-backed firms prefer direct lending—valuing speed, flexibility, and privacy over traditional bank lending—and how this justifies a yield premium [00:13:00]
  • How Cliffwater’s Direct Lending Index has shown consistent historical returns around 9.5%, with a 300–400 basis point premium over high-yield bonds [00:15:07]
  • The operational simplicity, lower minimums, daily NAV updates, and 1099 tax reporting advantages of interval funds over traditional private equity funds [00:25:12]
  • And more!

Resources:

Connect with Rex Berger: 

Connect with Phil Huber: 

About Our Guest: 

Phil is a Managing Director and Head of Portfolio Solutions for Cliffwater, based in their Chicago office. In this role, Phil leverages his prior experience as a wealth management CIO to produce and curate investment research, advise on product strategy and positioning for the firm’s growing platform, and help establish and strengthen relationships with the nation’s leading wealth management firms.

Prior to joining Cliffwater, Phil was the Chief Investment Officer for Savant Wealth Management. He earned a bachelor’s degree in finance from the Kelley School of Business at Indiana University. He is a CERTIFIED FINANCIAL PLANNER™ professional, has attained his Chartered Financial Analyst® (CFA®) designation, and is a member of the CFA Society of Chicago.

Phil has been featured in a number of notable media outlets, including The Wall Street Journal, The New York Times, InvestmentNews, CityWire RIA Magazine, and Bloomberg TV. From 2018-2020, he was named one of Investopedia’s Top Financial Advisors. Phil was also named CIO of the Year by RIA Intel in 2023.

Phil and his wife Christie live in the north suburbs of Chicago where they enjoy staying active and spending time with their two young children, Hannah and Owen. He is also a lifelong, die-hard professional wrestling fan.

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Generational Investments featuring CIO Steve Kolano (Ep. 2)

Generational Investments featuring CIO Steve Kolano (Ep. 2)

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There’s a quiet revolution reshaping how investors build wealth—and it’s not about chasing headlines or hype.

Why are fewer companies going public, and what does that mean for you? What’s really happening under the surface in private credit and equity markets?

In this episode, Rex Berger, Private Wealth Advisor of Generation Capital Advisors, sits down with Steve Kolano, Chief Investment Officer at Integrated Partners, to break down the realities of public versus private investing, why simplification beats complexity, and how private markets are evolving. Together, they unpack what it takes to construct portfolios designed to last for generations.

Key Takeaways:

  • Why most alpha should come from tax and estate planning rather than trying to beat the market [00:10:14]
  • How their “core and explore” philosophy balances efficient index investing with selectively vetted alternatives [00:13:20]
  • The dramatic drop in publicly listed companies since 2000 and the resulting rise of private market opportunities [00:14:40]
  • How market conditions and rising interest rates are forcing private equity firms to focus on long-term operational value over quick exits [00:19:38]
  • The importance of manager selection and due diligence in navigating the private credit and equity space [00:22:00]
  • And more!

Resources:

Connect with Rex Berger: 

Connect with Steve Kolano: 

About Our Guest: 

Steve Kolano brings a deep passion for both financial markets and people to his role, ensuring that every investment strategy he oversees is custom-built to align with each client’s personal vision of success.

He understands that financial markets are complex, dynamic systems, constantly adapting and evolving. People are no different. Each investor carries unique beliefs, perspectives, and goals that shift over time.

Steve’s mission is rooted in understanding the individual first. What drives them? What informs their decision-making? What is their “why”? By uncovering these insights, Steve crafts investment portfolios that are not only tailored to the person but also integrated with their broader financial plans and strategies.

Throughout his career, Steve has come to embrace a critical truth: there is no magic bullet in investing. No secret formula. No one-size-fits-all portfolio.

What sets Steve apart is his process, beginning with a deep understanding of the client and then applying the art and science of investing in pursuit of their specific goals.

In the end, Steve believes the closest thing to a magic bullet in investing is a well-designed, disciplined plan—and the commitment to stick with it.

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Generation Capital Advisors: A better way to manage wealth (Ep. 1)

Generation Capital Advisors: A better way to manage wealth (Ep. 1)

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Most wealth problems are not caused by one bad investment; they come from complexity that never gets cleaned up.

In this episode, Matt Ackerman hosts a conversation with Samuel Diarbakerly to talk about why “simplification is the ultimate form of sophistication,” and what it actually takes to make wealth management feel clear, coordinated, and human. Samuel Diarbakerly shares how Generation Capital Advisors was built to deliver family-office-level coordination without the typical ultra-high minimums. They walk through the firm’s planning-first process, why most people cannot even find their existing financial plan, and how the right team can quarterback tax, estate, investments, insurance, and client service as one connected strategy. The conversation also covers the “core and explore” portfolio structure, using technology and selective AI thoughtfully, and building a generational firm culture rooted in partnership and kindness.

What to expect:

  • Why simplification can be a competitive advantage in wealth management
  • The difference between investment management and holistic planning leadership
  • “Core and explore” portfolios, endowment-style simplicity, and purposeful complexity
  • How strong advisors coordinate CPA, estate attorney, and planning conversations
  • The generational question families quietly worry about most
  • Where technology, cybersecurity, and AI fit, and where they should not
  • Why Integrated Partners became the operational backbone for Generation Capital’s growth
  • And more!

Connect with Sam Diarbakerly: 

Connect with Matt Ackerman:

About our Guest:

Matt Ackerman is a leader at Integrated Partners and the episode host. He guides a candid conversation with Samuel Diarbakerly on how modern advisory firms can combine high-touch service, thoughtful technology, and disciplined planning to help families simplify complexity and stay focused on what matters most.

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