Retirement often changes how your wealth is structured, distributed, and taxed, potentially exposing estate planning gaps that were easy to overlook during your working years.
In this episode, Larry Heller, CFP®, CDFA®, explores why retirement is a new phase of estate planning and what families, especially those with higher net worth, should be reviewing now.
Larry discusses:
Why signed estate documents are not the finish line once you retire
How beneficiary designations can override your will
Common mistakes with outdated beneficiaries, minor children, and second marriages
Why asset titling and TOD/POD accounts must align with your estate plan
Key considerations for high-net-worth families, including New York’s estate tax cliff
The importance of revisiting trusts, executors, and family communication
Most people think life insurance is only about what happens after they are gone. But what if part of your coverage could support you during a serious health event while you are still living?
In this episode, Larry Heller, CFP®, CDFA®, sits down with Richard “Big Daddy” Salgado to explore how life insurance has evolved beyond the traditional death benefit. Drawing from his experience working with professional athletes, Rich shares how career-ending disability coverage and life insurance with living benefits are designed to protect income, earning potential, and financial stability when the unexpected happens.
Richard discusses:
The difference between traditional life insurance and policies with living benefits
How career-ending disability insurance protects future income
What health events may trigger living benefit payouts
Why policy reviews are essential as your life and finances change
Common misconceptions about life insurance and protection planning
About Our Guest: Richard “Big Daddy” Salgado is an insurance professional with more than 25 years of experience specializing in career-ending disability coverage and life insurance with living benefits. He has worked extensively with professional athletes, helping them protect future earnings and financial stability in the event of injury or serious health challenges. Rich focuses on education-first conversations, policy reviews, and ensuring clients understand how protection planning fits into their broader financial picture.
Why Taxes Often Go Up in Retirement, and What Planning Ahead Can Change (Ep. 194)
Many people enter retirement expecting their taxes to decline, but for many retirees, the opposite happens.
In this episode, Larry explains why retirement income often becomes more taxable over time and how a lack of coordination can quietly increase stress, healthcare costs, and long-term tax exposure.
In this episode, Larry Heller, CFP®, CDFA®, discusses:
Why retirement is often not a low-tax phase of life
How required minimum distributions, Social Security, and taxable accounts interact
Common tax mistakes retirees make when planning starts too late
Why tax planning should be ongoing, not a once-a-year conversation
How income decisions can affect Medicare premiums and overall cash flow
Ways proactive planning may help retirees reduce surprises and stay in control
Why does investing feel so emotional, even when the plan is solid? This episode explores how psychology, and not just numbers, shapes the way investors react to markets.
In this episode, Larry Heller, CFP®, CDFA®, CPA, is joined by Scott Bosworth, CFA, Head of Speakers Bureau and Vice President at Dimensional Fund Advisors, to discuss how investor behavior and common behavioral biases influence long-term investment outcomes. Scott explains why emotions often feel more powerful than logic during market swings and how those reactions are deeply rooted in human psychology, not a lack of intelligence or discipline.
The conversation also explores the tension between efficient markets and behavioral finance, and why understanding both is essential to staying invested through market cycles. Throughout the episode, Scott shares practical analogies and real-world examples that help investors better recognize their own biases and make more resilient decisions over time.
Scott discusses:
What behavioral finance is and why it matters for investors
The most common biases that affect decision-making, including overconfidence and hindsight bias
Why market headlines and media narratives can increase anxiety
How diversification and discipline help investors stay grounded during uncertainty
The role advisors play in helping clients navigate emotional market cycles
Scott Bosworth, CFA, is Head of Speakers Bureau and Vice President at Dimensional Fund Advisors. He has been with the firm since 1996 and brings decades of experience as a portfolio manager, institutional and advisory consultant, and trusted resource for advisors navigating market behavior and long-term investing principles.
Starting the Year With the Right Retirement Questions (Ep. 192)
The start of a new year is one of the most valuable planning moments for retirees, not because everything needs to change, but because the right questions can shape better decisions all year long.
In this episode, Larry Heller, CFP®, CDFA®, walks through the key January questions retirees should be asking, covering taxes, withdrawals, cash management, portfolio alignment, and lifestyle planning, so small adjustments now can help reduce stress later.
Larry discusses:
Why it matters which accounts you withdraw from in retirement, not just how much you take
How tax-efficient withdrawal planning can help manage future tax brackets
When Roth conversions may still make sense during retirement
How much cash do retirees want on hand to avoid selling investments during market downturns
Why portfolio alignment should support spending needs, inflation, and peace of mind
The importance of reviewing beneficiaries, estate documents, and healthcare cost planning
How planning builds confidence to enjoy retirement without overspending or underspending
Selling a business is one of the biggest financial decisions an owner will ever make, and the right preparation can shape both the outcome and the next chapter of life.
In this episode, Larry Heller, CFP®, CDFA®, speaks with Gregg Schor, CEO of Protegrity Advisors, about what business owners need to understand before entering the mergers and acquisitions process. Gregg shares practical, experience-based insights into how different buyer types approach transactions and how sellers can position themselves well ahead of a sale to improve both financial and non-financial outcomes. Together, they walk through the typical Mergers & Acquisitions timeline and key decision points business owners should be prepared to navigate from early planning through closing.
Gregg discusses:
The different types of buyers in today’s market, including strategic buyers, private equity firms, and family offices
How seller goals influence deal structure, timing, and buyer fit
The role of cash at closing, earnouts, and rollover equity in a transaction
Why the best time to consider selling is often when the business is performing well
What preparation really looks like, from financials and contracts to reducing owner dependency
How the M&A process typically unfolds, from early planning through closing
Gregg Schor is the CEO of Protegrity Advisors and has over 25 years of experience managing mergers and acquisitions, corporate development, legal, and human resources for companies of all sizes in a wide range of industries. He has previously held senior management positions at companies that have been acquired by IBM, Microsoft, and EMC, including Deputy and General Counsel, Senior Vice President of Corporate Development, Senior Vice President of Human Resources, and Director of European Operations. As a result, he brings a very unique perspective to Protegrity clients, having been on all sides of M&A transactions and in a variety of roles.
Over the years, he has developed an extensive network of national and international relationships with public and private companies, private equity firms, family offices, search funds, and serial entrepreneurs, looking for businesses to acquire. He is on the boards of the Exit Planning Institute and the Alliance of Merger & Acquisition Advisors, and is a member of the Exit Planning Exchange (Long Island Chapters).
Gregg received a J.D. from St. John’s University School of Law and a Diploma on International and Comparative Law for study in Russia and Poland from the University of San Diego School of Law. He also completed the Mergers and Acquisitions Executive Education Program at the Wharton School of the University of Pennsylvania and the Certificate Program in Family Business Leadership and Governance from Cornell University.
Key Decisions to Get Right in Your 60s for a Confident Retirement (Ep. 190)
Planning for retirement in your sixties involves a series of decisions that shape the rest of your life. Many retirees and pre-retirees are unsure how Social Security, healthcare, taxes, investments, and estate planning all work together, and this uncertainty can lead to costly missteps.
In this episode, Larry Heller, CFP®, CDFA®, breaks down the most common mistakes he sees people make during this decade and explains how thoughtful planning can help you approach retirement with clarity and confidence. He highlights real-world scenarios where timing, income needs, and coordination across financial decisions can make a meaningful difference for retirees and their families.
What to expect:
The Social Security mistakes many people make at ages 62 to 67
How income needs, longevity, and spousal benefits affect the right claiming strategy
Why knowing your spending is one of the most powerful pieces of retirement planning
Healthcare planning essentials, including Medicare, IRMAA, and long-term care
Managing investments in your sixties without becoming too conservative too quickly
Missed tax opportunities such as Roth conversions and withdrawal sequencing
Emotional preparation and lifestyle planning for a fulfilling retirement
Why updated estate documents and beneficiary designations matter
Retirement planning for Northwell Health employees involves understanding a range of unique benefits and making strategic financial decisions. Many employees across all tiers and roles are unsure how these pieces fit together as they approach retirement.
In this episode, Larry Heller, CFP®, CDFA®, speaks with Belinda Tsui, CFP®, about how strategic planning can help employees understand what they have, what they may be leaving unclaimed, and how each decision affects retirement planning goals.
They explore common scenarios for physicians, nurses, administrators, and other employees navigating their retirement plan options. The message is clear: knowing your benefits early, coordinating income sources, and avoiding costly timing mistakes can make a meaningful difference for Northwell employees when it’s time to retire.
What to expect:
The most common benefits Northwell employees might miss
Key decisions employees face as they approach age 65
Northwell pensions, cash balance plans, and deferred compensations
How Heller Wealth Management has helped their Northwell clients that are nurses, administrators, & physicians to set up for a successful retirement
Belinda Tsui, CFP® approaches wealth management the same way she undertakes any other discipline in her life. She has many clients that are working for Northwell Health or have retired from Northwell Health with her help. With laser focus, cool reserve, steely resolve and unwavering adherence to the principals and fundamentals that foster success and lead – ultimately – to mastery of the craft. The ‘craft’ in this case being comprehensive financial and investment planning. The finer points of which include designing customized portfolios, plan implementation, portfolio rebalancing, customizing asset reports and operations management. Skills acquired and finely honed over 20 years of advising, counselling and creating financial resilience for high net worth individuals, family trusts, foundations, corporate executives and business owners.
What You Can Still Do to Cut Your 2025 Tax Bill with Jonathan Niyazov (Ep. 188)
Year-end tax season doesn’t have to catch you off guard. With the latest tax law updates now in effect, there are new windows of opportunity, but also new limitations, especially for high-income earners and business owners.
In this episode, Larry Heller, CFP®, CDFA®, sits down with Jonathan Niyazov, CPA, to unpack how the 2025 tax code changes are reshaping financial planning conversations. From expanded SALT deductions and personal exemptions to permanent bonus depreciation and R&D credits, the 2025 tax code changes are reshaping planning conversations. The real challenge? Knowing how and when to act before December 31st to keep more of what you’ve earned.
What to expect from this release:
How income thresholds impact the new deduction and exemption limits
Strategic planning moves for high earners, senior taxpayers, and business owners
The power of Roth conversions, tax-loss harvesting, and retroactive refund claims
Why choosing the right business structure may help reduce your tax bill in 2025 and beyond
Jonathan Niyazov is an accomplished Certified Public Accountant (CPA) with a wealth of experience assisting mid-size to large businesses and high-net-worth individuals with their tax needs. With a distinguished career spanning prestigious international accounting firms, he brings an acute understanding of the tax code that is crucial for any growing business and its owners. Jonathan’s expertise extends to assisting overseas companies in establishing a business presence in the United States and providing guidance to US companies expanding abroad.
He leverages his commercial tax expertise to deliver high-quality tax services to a diverse portfolio of clients across many industries and sectors. His experience and expertise is centered around tax management, consulting, and compliance, with a focus on S corporation, partnership, corporate, and individual taxation.
Later-in-Life Marriages: What You Need to Protect (Ep. 187)
When love finds you later in life, what happens to your legacy?
With over 1,300 stepfamilies forming every day, later-in-life relationships are more common than ever, but so are the financial complexities that come with them.
Whether you’re remarrying, cohabiting, or just exploring the next chapter, decisions around Social Security, estate planning, asset titling, and medical directives can be emotionally and financially loaded.
We’re laying out what you need to think through before you say “I do” (or move in). Because when assets, families, and emotions all intersect, proactive planning is what brings peace of mind.
What to expect:
The critical age 60 rule that can impact your Social Security survivor benefits
How to protect your kids from a previous marriage, even if you trust your new spouse
What happens to your home if you’re unmarried and pass away first?
Why adult children need to be part of your planning conversations
