What seems like a small business decision, choosing between a SIMPLE IRA and a 401(k), can quietly shape everything from your personal retirement strategy to your firm’s employee retention.
The truth? It’s not just about cost. It’s about control, flexibility, and future-proofing your business and your finances.
Whether you’re a solo entrepreneur or managing a team, your retirement plan structure says a lot about your growth mindset.
In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, explores the practical trade-offs business owners face when deciding how much control they want, how much complexity they can handle, and how much opportunity they may be unknowingly leaving on the table.
Here’s what you can expect from this release:
How contribution limits and tax credits differ between SIMPLE IRAs and 401(k)s
How Safe Harbor rules can protect owners from compliance headaches
Why profit sharing and vesting can impact employee loyalty
The often-overlooked role of plan design in talent retention
Why cost-saving now may cost you more later, financially and culturally
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
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.
What Should You Do with Your 401(k) When You Retire? (Ep. 181)
Your 401(k) could be your largest retirement asset, but are you making the most of it?
In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, shares the essential steps to take with your 401(k) as you approach retirement. From rollover decisions and Roth conversions to income generation and estate planning, Larry covers the strategies that can help you avoid costly mistakes and keep more of what you’ve earned.
Key Topics Include:
When to consider rolling over your 401(k) to an IRA
How Roth conversions can reduce your lifetime tax bil
What to know about fees, investment choices, and employer stock
How to build a tax-efficient withdrawal strategy
The importance of naming the right beneficiaries
And more!
Whether you’re retiring soon or planning ahead, this episode is your guide to making smart 401(k) decisions so you can step into retirement with confidence.
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
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.
Understanding the Insurance Market Crisis: Higher Rates, Tougher Carriers, and Smart Moves with Gregg Knepper [Ep.174]
Wildfires. Hurricanes. Cyber Attacks. How are today’s biggest threats reshaping the insurance industry—and what can you do to stay protected?
In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, sits down with Gregg Knepper, President of Integrated Coverage Group, to break down the rapidly changing insurance landscape. With more than 15 years of experience in risk management and personal insurance, Gregg shares expert insights into how natural disasters, inflation, and digital threats are driving up premiums—and what you can do about it.
From rising home and auto rates to the hidden gaps in your umbrella and cyber insurance, this conversation is packed with practical tips for protecting what matters most.
Key discussion points include:
Understanding personal insurance market challenges [01:00]
Impact of national disasters on local insurance premiums [02:45]
Adjusting policies with higher deductibles for cost efficiency [10:30]
The role of umbrella coverage and uninsured motorist protection [18:15]
The rise of cyber threats and the necessity for cyber insurance for individuals and businesses [24:00]
Gregg Knepper is an experienced Insurance Adviser specializing in helping businesses and individuals limit their risk. As the President of Integrated Coverage Group, a rapidly growing insurance brokerage, Gregg brings over 13 years of expertise in the industry. Unlike traditional brokers who work for specific insurance carriers, Gregg is dedicated to working solely for their clients, ensuring that each client receives a solution tailored to their unique needs.
With a focus on reducing risk, Gregg works closely with clients to craft personalized insurance strategies across a wide range of areas, including workers’ compensation, employee benefits, and cyber insurance. Known for their trustworthiness, knowledge, and honesty, Gregg partners with clients every step of the way to ensure that their risks are managed effectively.
Specializing in supporting quickly growing businesses with sophisticated insurance and risk management needs, Gregg has extensive experience in serving industries such as technology firms, medical practices, real estate, manufacturing, and restaurants and hospitality.
Whether a client is a small startup or a large, complex organization, Gregg Knepper provides the expertise and dedication to meet their specific insurance needs.
5 Tax Gotchas That High-Net-Worth Individuals Overlook [Ep.173]
What tax traps could derail your retirement plans?
In this episode, Larry Heller, CFP®, CDFA®, breaks down five major tax “gotchas” that high-net-worth retirees must navigate to protect their wealth and retirement security.
From the impact of required minimum distributions to the looming expiration of the 2017 tax cuts, Larry sheds light on often-overlooked tax challenges. He also explores strategic solutions like Roth conversions and income planning to help retirees minimize surprises and maximize financial confidence.
Key episode discussions include:
Required Minimum Distributions (RMDs) and their tax impact [03:09]
Expiration of the 2017 Tax Cuts and Job Act [04:04]
The “Widow Penalty” and implications for single retirees [07:37]
Gifting strategies and estate planning considerations [10:03]
The consequences of leaving large IRAs to children [11:05]
What does it mean to face the ‘sequence of returns risk’ when you retire?
In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, discusses why the order of your investment returns matters as you enter retirement. Larry also breaks down this critical aspect of retirement planning and introduces strategies that can safeguard your financial future.
Key episode discussion points include:
The shift from “Life Unlimited” to “Retirement Unlocked”
How the sequence of returns can impact retirees
Historical examples of sequence of returns risk
The reservoir strategy for mitigating those risks
Insights on adjusting your withdrawal strategy
Behavioral finance and the psychological aspects of investing
Do you know the smartest way to manage your withdrawals in retirement?
In this episode of the Life Unlimited podcast, host Larry Heller, CFP®, CDFA®, shares expert strategies for managing retirement withdrawals to ensure financial stability and tax efficiency.
Larry covers essential steps for building a smart distribution plan, emphasizing pre-retirement planning and proactive wealth management. The episode explores the benefits of Roth conversions, the impact of the Secure 2.0 Act, and critical topics such as the widow penalty, annuities, and estate planning, all supported by real client insights.
Whether you’re approaching retirement or already retired, this episode offers practical tips to help you minimize taxes, optimize withdrawals, and protect your wealth and legacy. Don’t miss this valuable guide to mastering your retirement finances!
Key episode discussions include:
Strategic tax planning to minimize taxes before the distribution phase
Understanding different income streams like Social Security, pensions, and retirement accounts
Real client scenarios illustrating the impact of effective and missed strategies
The effects of federal and state estate taxes, plus planning for longevity
Integrating attorneys and other professionals for a holistic financial plan
Retirement isn’t just about accumulating wealth – it’s about making sure it lasts.
In this episode, Larry Heller, CFP®, CDFA®, explores the essential elements of a well-rounded distribution strategy for retirement, including guiding you through five key areas every retiree should prioritize: income vs. total return, tax management, investment allocation, longevity, and estate planning.
Larry dives deep into the shift from accumulation to distribution, revealing strategies to help retirees sustain income, reduce taxes, and cover health expenses—all while preparing a meaningful legacy. With a focus on turning retirement into a financially secure and fulfilling stage of life, this episode provides actionable advice on balancing your immediate needs with a long-term vision.
Whether you’re entering retirement or aiming to enhance your financial strategy, this episode will equip you with the tools and mindset to enjoy a confident and comfortable retirement.
Key Points Covered:
Combining income sources like Social Security, pensions, and investments to balance retirement income and comfort
Reducing tax burdens through Roth conversions and managing required minimum distributions (RMDs) under the latest Secure Act changes
Using the “reservoir strategy” to balance cash, bonds, and equities for steady income and minimized risk
Addressing healthcare and long-term care costs to protect assets and maintain financial stability
Aligning estate plans with tax strategies to maximize inheritance for heirs
And much more!
Actionable Takeaway: Review your retirement plan to ensure it supports your lifestyle, reduces tax impacts, and aligns with your legacy goals. Consult a financial planner to tailor it to your unique needs for a fulfilling retirement.
Interest rates may be falling, but your financial strategy doesn’t have to follow. Learn how to stay ahead in today’s ever-changing financial landscape.
Larry Heller, CFP®, CDFA®, breaks down how these shifting rates impact everything from mortgages to retirement plans. Whether you’re buying a home, optimizing investments, or planning for your financial future, Larry offers actionable insights to help you navigate today’s economic landscape. Covering the rise and fall of interest rates and their effects on borrowing, saving, and investing, he provides strategies for adapting your financial plan across asset classes to protect your wealth.
Key Points Covered:
The Federal Reserve’s interest rate cut and its broader economic implications
How shifting rates impact mortgage costs, housing availability, and borrowing strategies
Key adjustments to retirement planning, including withdrawal rates and asset allocation in a low-rate environment
Adapting your savings strategy with CDs and treasuries (while considering the current inverted yield curve!)
Effective investment approaches across bonds, stocks, and real estate in the face of rate fluctuations
Opportunities in private equity and private credit investments as interest rates decrease
The importance of a diversified strategy and proactive communication, as emphasized by Heller Wealth Management
