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.
Think you’ve done everything right for retirement? One overlooked tax detail could cost you thousands.
In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, welcomes Rob Premselaar, CPA and founder of Premselaar CPA LLC, to shed light on the hidden tax pitfalls that can derail even the most carefully crafted retirement plans.
They explore the real impact of Required Minimum Distributions (RMDs), the surprise taxation of Social Security benefits, and the often-misunderstood IRMAA Medicare surcharge. Rob also shares proactive strategies for minimizing taxes in retirement, including qualified charitable distributions (QCDs), the pros and cons of Roth conversions, and key planning opportunities for business owners approaching or entering retirement.
Discussions in this release include:
The income thresholds that quietly increase your Medicare premiums (IRMAA)
Why Roth conversions are often misunderstood and underutilized
How to navigate RMD timing and avoid excise penalties
How Medicare surcharges can catch retirees off guard and what to do about them
Advanced planning opportunities using cash balance plans
Rob is the Owner of Premselaar CPA LLC, managing a portfolio of small-to-medium sized businesses and high-net-worth individuals, providing tax planning, tax strategy, tax filing, and CFO business services. Premselaar CPA LLC provides outstanding service to its clients because of its dedication to the three underlying principles of quality, professionalism, and responsiveness.
How Much Cash Should You Have in Retirement? (Ep. 179)
Are you holding too much, or too little cash in retirement?
Finding the right amount of cash to keep on hand is one of the most important decisions you’ll make when creating a retirement income strategy. The wrong decision could lead to stress, missed growth opportunities, or even long-term financial instability.
In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, breaks down how much cash retirees should have in their portfolio, and why it matters more than you might think. He introduces his “retirement cash reserve strategy,” designed to help you generate steady income while protecting against market volatility.
What to expect in this episode:
A breakdown of bear vs. bull markets since 1945 and what they teach us about cash reserves
How to calculate 24–36 months of protected cash for downturns
The role of risk tolerance and income modeling in reserve planning
How to build a personal “cash reservoir” that keeps retirement stress low
Outsourcing your bookkeeping isn’t just a cost-saving move; it could be the smartest strategic decision your business makes this year.
In this episode, Larry Heller, CFP®, CDFA®,sits down with Cheri Giglia, Owner and Managing Director of Supporting Strategies on Long Island, to explore why more small businesses are turning to virtual bookkeeping for efficiency, clarity, and peace of mind.
Cheri shares how outsourced financial support can streamline operations, enhance internal controls, and deliver timely insights that empower business owners to make better decisions, whether they’re planning for growth, managing cash flow, or preparing for an audit. With real client stories and tech-forward best practices, this episode is packed with value for any business owner looking to scale smarter.
What to expect from this episode:
The top reasons businesses are turning to virtual bookkeeping
How cloud-based systems streamline accounting operations
Real client scenarios where bookkeeping impacted business decisions
Tips for choosing the right outsourced financial team
Accounting and bookkeeping are services that many businesses on Long Island need to manage more effectively. Business owners struggle to find professionals who they trust to manage these important aspects of their operations. This is where Cheri Giglia and her company, Supporting Strategies on Long Island, come in. Her professional team removes owners’ headaches and improves efficiencies.
As an accountant and former Financial Director for a public company, Cheri has expertise working in many different industries. She understands the pressure and stress that business owners face when it comes to gaining greater financial control of their operations. She uses her more than two decades of experience in accounting and financial management to create strategies to improve efficiencies and reduce costs.
Cheri’s team of skilled accounting professionals accomplishes this by leveraging technology, allowing clients to easily outsource accounts payable management, billing/accounts receivables, financial/management reporting, HR and payroll support, bookkeeping and monthly financial statements/reports, and controller services. Outsourcing these services allows businesses to focus on growth and other profit-making activities. The way Cheri’s team operates permits them to offer competitively priced professional services and attention that competitors are unable to offer.
Cheri recognizes that there are many choices when it comes to selecting a professional or firm to provide accounting, bookkeeping, and controller services. Business owners and managers choose to work with her because of her experience, personal commitment, and her ability to rapidly provide the financial information they need to make critical business decisions.
The market is unpredictable; your retirement plan shouldn’t be.
In this episode of Retirement Unlocked, host Larry Heller, CFP®, CDFA®, breaks down six of the most common (and costly) mistakes people make when planning for retirement. From underestimating how much you can spend to failing to optimize your Social Security benefits, Larry shares why these pitfalls occur and how a process-based retirement plan can help you avoid them.
Whether you’re approaching retirement or already there, this episode provides actionable strategies to help you invest wisely, reduce emotional decision-making, and stay aligned with your long-term financial goals.
Key conversations in this week’s release include:
The importance of knowing how much you can truly spend in retirement [00:00:47]
Why creating a total return strategy beats relying solely on income [00:03:20]
The pitfalls of being too conservative with your investment portfolio [00:07:02]
When to start withdrawing from your retirement accounts—not just when RMDs kick in [00:10:32]
How to optimize Social Security for the best possible outcome [00:13:17]
The critical need for a comprehensive estate plan [00:15:51]
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.
Your 5-Year Retirement Countdown: Key Steps to Take Now [Ep.175]
What are some steps you should be taking 5 years before your retirement?
This question sets the stage for an engaging episode with Larry Heller, CFP®, CDFA ®, where we delve into the crucial five-year countdown to retirement.
Larry emphasizes the importance of timely planning and actionable strategies to ensure a smooth shift into this new life phase. From building up cash reserves to maximizing 401(k) contributions, Larry walks us through a comprehensive guide tailored to those nearing retirement.
Larry covers topics such as:
Building cash reserves and why they’re crucial for a stable retirement [00:01:06]
Strategies to maximize your 401k contributions, especially for those over 50 [00:02:33]
Tax-efficient withdrawal strategies and their significance in your retirement plan [00:06:23]
The concept of a ‘Retirement Lifestyle Dry Run’ to mentally and financially prepare for life after work [00:10:34]
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.
