Retirement Unlocked

When your wealth reaches tens of millions of dollars, even one financial decision can affect your taxes, investments, estate plan, and family’s future. How do you make sure every part of your financial strategy is working together to protect what you’ve built? In this episode of Retirement Unlocked, host Larry Heller, CFP®, CDFA®, kicks off a two-part series exploring the complexities...

Are you approaching retirement and wondering whether paying taxes on your IRA now through a Roth conversion could help reduce your future tax bill? A Roth conversion can be an important part of retirement tax planning, but there’s no single approach that works for everyone. The timing, amount you convert, current and future tax brackets, Medicare costs, and even what you plan to leave to your chil...

Watching a stock or business grow substantially can feel rewarding, until you start thinking about the tax bill that could come with selling it. For investors with appreciated stock, multiple account types, or proceeds from a major sale, investment decisions and tax decisions can quickly become intertwined. In this episode, Larry Heller, CFP®, CDFA®, speaks with Angela R. Berkosky, CFA®, MBA, Dire...

Are you approaching retirement and wondering whether your investments, spending, taxes, estate plan, and future goals are all working together? A retirement plan should do more than track portfolio performance. It should help you understand how your money can support the lifestyle you want, while accounting for income needs, taxes, market risk, family priorities, and changing circumstances. In thi...

How do you sell a trade business and turn decades of work into retirement income? If you’re a contractor, electrician, plumber, landscaper, HVAC professional, or another skilled-trade owner thinking about retirement, the decisions you make before the sale may affect what your business is worth, how much you keep after taxes, and how the proceeds support your retirement.  In this episode, Larry Hel...

Are you approaching retirement and wondering whether your spending, investments, taxes, insurance, estate plan, and retirement lifestyle are all working together? A retirement plan should do more than help you reach a savings goal. It should support the life you want while preparing for changing markets, rising costs, healthcare needs, and a retirement that could last 30 years. In this episode, La...

A lot of people think their estate planning is complete once the legal documents are signed. But for retirees and families with complex assets, those documents may not be enough if trusts, beneficiary designations, account ownership, and tax planning aren’t coordinated. In this episode, Larry Heller, CFP®, CDFA®, speaks with Dominick J. Parillo, JD, CFP®, Director of Wealth Transfer at Savant Weal...

What should you do after selling your business? Closing the deal is a major milestone, but it’s only the beginning of a new chapter. Without a thoughtful plan, emotional decisions, tax surprises, and a lack of direction can undermine the financial freedom you’ve worked so hard to achieve. In this episode, Larry Heller, CFP®, CDFA®, explores the most common mistakes business owners make...

Retirement today looks very different than it did even a decade ago. Managing your finances, protecting your identity, staying connected with family, accessing healthcare, and preserving your legacy are all becoming increasingly digital. While these advancements offer greater convenience and flexibility, they also introduce new risks that deserve careful planning. In this episode of Retirement Unl...

Many retirees wonder whether they can safely spend more money in retirement without jeopardizing their future. Questions about retirement income, withdrawal rates, market volatility, healthcare expenses, and the fear of running out of money often prevent retirees from enjoying the wealth they’ve accumulated.  In this episode, Larry Heller, CFP®, CDFA®, discusses the often-overlooked challeng...

Losing a spouse is one of life’s most difficult experiences, emotionally and financially. Many retirees are surprised to learn that widowhood can also create significant tax and retirement-planning challenges that may affect income, Medicare premiums, estate plans, and long-term financial security.  In this episode, Larry Heller, CFP®, CDFA®, explains why the loss of a spouse can create unexpected...

In this milestone 200th episode of Retirement Unlocked, Larry Heller reflects on the journey of building the podcast from an audio-only show into a growing multimedia platform focused on helping people make smarter retirement decisions. Joined by co-host Bill Tucker, Larry shares why the podcast was created, the lessons learned over 200 episodes, and how financial education can truly impact people...

Many retirees assume their Medicare premiums will stay consistent once they enroll. But that’s not always the case, especially for higher-income individuals. In this episode, Larry Heller, CFP®, CDFA®, breaks down IRMAA, the income-related surcharge that can increase your Medicare Part B and Part D premiums based on income from two years prior. He explains how everyday financial decisions, from IR...

Retirement is often seen as a finish line, but in reality, the years surrounding it are where some of the most important decisions get made. In this episode, Larry Heller, CFP®, CDFA®, explains the concept of the retirement “danger zone”, the five years before and after retirement when financial, tax, and lifestyle decisions can have long-term consequences. Larry discusses: Why relocating for tax...

Retirement can look solid on paper, but confidence doesn’t come from a number; it comes from how your money actually works for you. In this episode, Larry Heller, CFP® breaks down why cash flow, not net worth, is the true driver of financial confidence in retirement. He explains how multiple income sources, tax considerations, and withdrawal strategies must be coordinated to create a sustainable p...

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 doc...

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 p...

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 ph...

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 l...

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, s...

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...

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 thi...

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...

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 e...

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 em...