Category: Estate Planning
How to Avoid a Tax Time Bomb in Retirement (Ep. 185)

How to Avoid a Tax Time Bomb in Retirement (Ep. 185)

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Roth conversions may be one of the most overlooked tax planning opportunities in retirement, and the cost of waiting could be staggering. 

With recent legislative changes, longer life expectancies, and compressed inheritance timelines for your heirs, it’s never been more important to get this right.

In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, explains how to spot your best conversion window, why many people miss it, and the strategic tools that can make the move pay off. He also reveals how proactive planning can help reduce Medicare surcharges, reduce the tax burden passed on to your family, and give you far more flexibility in retirement.

If you’re between the ages of 60 and 75, or experiencing a few low-income years before required minimum distributions (RMDs) begin, you could be in a prime window to convert pre-tax retirement savings into tax-free Roth dollars, without triggering a future tax time bomb.

Beyond personal savings, this strategy can also help protect the next generation from inheriting a massive tax liability. But timing, income coordination, and strategic use of tools like Social Security deferral and partial conversions all play a role in whether a Roth move will actually benefit you.

What you can expect from this release:

  • Why accountants often overlook this opportunity, and how a CFP® can model your long-term tax impact
  • The ideal timeline to explore Roth conversions, especially in the “donut hole” between retirement and RMDs
  • How Roth IRAs can minimize Medicare surcharges, reduce required withdrawals, and increase future flexibility
  • The multi-generational benefits of converting, including how to shield your heirs from 10-year withdrawal rules
  • And more!

Connect with Larry Heller: 

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Our recommended title: How to Exit Your Business on Your Terms with Paul Cronin (Ep. 184)

Our recommended title: How to Exit Your Business on Your Terms with Paul Cronin (Ep. 184)

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You’ve built a business with care, grit, and vision. But what happens when the finish line is in sight and you realize you’re not ready to cross it? 

For business owners nearing retirement, the decision to sell is about far more than spreadsheets and valuations. It’s personal. It’s strategic. And it can be overwhelming.

In this episode of Retirement Unlocked, Larry Heller sits down with Paul Cronin, a seasoned entrepreneur and M&A advisor with Touchstone Advisors, to walk through how and when to start planning for your exit, on your terms.

What you can expect from this release:

  • The real (and often underestimated) timeline for selling a business
  • Why your business must be ready to sell before you are
  • The “Holy Trinity” of trusted advisors to involve early
  • Common mistakes that derail deals and how to avoid them
  • And more!

Resources: 

Connect with Paul Cronin:

Connect with Larry Heller: 

About Our Guest:

Paul Cronin has over 30 years of professional experience in sales, management, consulting, and entrepreneurship. He has owned three businesses, including a data analytics business, a golf training business, and an exit planning/consulting business. He has been part of the M&A world since 2009, initially in the exit planning field before moving to transactional work at several firms. Paul joined the M&A practice at Touchstone Advisors in 2025

Paul’s background includes being part of the team that grew Eden Toys, a small NY-based toy manufacturer, into a $100 million company serving thousands of US retailers, including TJX, Macy’s, and Nordstrom. Paul led a team of 16 salespeople (both field reps and inside sales reps,) generating $20 million/year and serving 6,000 customers.

As a speaker, Paul has presented at law firms, CPA societies, professional associations, and colleges such as Harvard Business School, Northeastern University, Babson College, Bentley University, Wheaton College (MA), Emerson College, Wellesley College, and Salem State University (MA).

Paul has a Bachelor of Science from the D’Amore-McKim School of Business at Northeastern University in Boston. Paul is an avid golfer, splits his time between Boston and Cape Cod, and is married with two adult daughters.
SIMPLE IRA vs. 401(k): What’s Best for Your Business? (Ep. 183)

SIMPLE IRA vs. 401(k): What’s Best for Your Business? (Ep. 183)

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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
  • And more!

Resources:

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

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

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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.
What Should You Do with Your 401(k) When You Retire? (Ep. 181)

What Should You Do with Your 401(k) When You Retire? (Ep. 181)

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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.

Resources: 

Connect with Larry Heller: 

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Top Retirement Tax Pitfalls to Avoid with Rob Premselaar (Ep. 180)

Top Retirement Tax Pitfalls to Avoid with Rob Premselaar (Ep. 180)

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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
  • And more!

Connect with Rob Premselaar:

Connect with Larry Heller: 

About Our Guest:

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)

How Much Cash Should You Have in Retirement? (Ep. 179)

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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
  • And more!

Resources: 

Connect with Larry Heller: 

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More Time, Less Stress: Why Smart Businesses Are Outsourcing Their Bookkeeping with Cheri Giglia (Ep. 178)

More Time, Less Stress: Why Smart Businesses Are Outsourcing Their Bookkeeping with Cheri Giglia (Ep. 178)

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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
  • And more!

Connect with Cheri Giglia:

Connect with Larry Heller: 

About Our Guest:

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 6 Retirement Mistakes To Avoid (Ep. 177)

The 6 Retirement Mistakes To Avoid (Ep. 177)

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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]
  • And more

Connect with Larry Heller: 

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

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

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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.