Legacy Planning

Charitable Giving in Retirement & Smart Tax Strategies to Maximize Your Impact with Joshua Chadajo (Ep. 182)

By Retirement Unlocked | August 20, 2025

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How can you give more to the causes you care about while keeping more of your hard-earned money?

Charitable giving isn’t just a personal act of generosity; it’s also a strategic financial opportunity.

In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, sits down with philanthropy professional Joshua Chadajo, CEO of JEC Philanthropy, to explore how intentional giving strategies can help you reduce your tax burden, maximize your impact, and build a legacy that reflects your values. Joshua shares how tools like donor-advised funds, qualified charitable distributions, and bunching donations can make your giving both intentional and tax-efficient.

Key insights include:

How to turn appreciated assets into bigger gifts while avoiding capital gains taxes
Why donor-advised funds offer convenience and flexibility for both donors and charities
Ways to bunch donations to maximize deductions under today’s tax rules
When foundations make sense for larger-scale or multi-generational giving
Why giving during your lifetime can be more rewarding and impactful than waiting
And more!

Connect with Joshua Chadajo:

Connect with Larry Heller:

About Our Guest:

Joshua E. Chadajo is the founder and CEO of JEC Philanthropy. His fundraising leadership has resulted in more than $100 million of charitable donations. What he enjoyed most during his thousands upon thousands of conversations with and about donors is uncovering what motivates each individual to give charity, clarifying what each person hopes to accomplish with their support, and determining how best to achieve these goals. Joshua formed JEC Philanthropy to share his passion for charitable giving with individuals and families who can benefit from his wealth of experience.

Joshua was the longest-tenured Executive Director, North America at the Pardes Institute of Jewish Studies in Jerusalem. He was the first alumnus to hold the position, which he did for more than 18 years. Joshua earned a reputation for getting things done and achieving a high level of excellence, all while exhibiting a persistent positive attitude, a strong sense of humor and a distinct lack of jargon.

Joshua spent the last 25 years working at three different nonprofit organizations, holding executive positions in two of them, and serving on multiple nonprofit boards. He has extensive experience in fundraising, strategy, finance, operations, communication and relationship-building.

Joshua earned an MBA at the Yale School of Management, which he attended as a Wexner Graduate Fellow. After graduation, he spent a year learning at the Pardes Institute. A native of Boston, MA, Joshua currently lives in Miami Beach, FL with his family. He still roots, however, for the correct sports teams.

Breaking the Health Insurance Mold: The New Health Plan Playbook with Louis Bernardi [Ep. 176]

By Retirement Unlocked | May 21, 2025

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Health insurance is one of the largest expenses for many businesses, but are you getting what you’re paying for?

In this eye-opening episode, Larry Heller, CFP®, speaks with Louis Bernardi of BrightPath Benefit Advisors about the outdated and opaque nature of most employer-sponsored health insurance plans. Louis reveals how major carriers prioritize shareholder profits over actual care and explains how his PLAN system and data-driven strategies are helping employers cut costs while providing better healthcare options for employees.

From skyrocketing pharmacy costs to hidden MRI fees, Lou unpacks the waste baked into the system and provides actionable strategies to fix it. This is a behind-the-scenes look at an advanced strategy most employers haven’t even heard of.

Key discussions in this release include:

Why traditional health insurance models are broken
The hidden data behind skyrocketing healthcare costs
How Lou’s PLAN system (Prioritize, Leverage, Align, Navigate) helps optimize benefit design
Real-world savings on pharmacy and imaging costs
Options for companies of all sizes
And more!

Connect with Louis Bernardi:

Connect with Larry Heller:

About Our Guest:

Louis Bernardi is the Founder & Benefit Optimization Officer of BritePath. Lou is the innovator behind BritePath, the benefit strategy that flattens the curve on health insurance costs. BritePath helps benefit decision makers reset their expectations with advanced analytics & insights that make them and their members more informed health care consumers capable of changing the trajectory of the cost and quality of their employer-sponsored health insurance plan. Pay More, Get Less is replaced by a High-Performance Health Care Plan that allows them to finally start winning.

Lou is proud to be among the first 150 advisors accepted into Health Rosetta; an eco-system of forward-thinking advisors and solution partners that share his passion for helping people and businesses customize health plans that enhance benefits, improve outcomes and reduce costs.

Lou is also involved with Aspirational Healthcare, Free Market Medical and is a Forbes Business Council member.