Tag: Retirement Planning
Direct Indexing and Tax-Loss Harvesting with Angela R. Berkosky (Ep. 209)

Direct Indexing and Tax-Loss Harvesting with Angela R. Berkosky (Ep. 209)

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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, Director of Investment Strategy at Savant Wealth Management, about incorporating taxes into portfolio decisions. They explore how different investments may fit within taxable accounts, traditional IRAs, and Roth IRAs, along with approaches for managing highly appreciated positions. Angela also covers direct indexing, tax-loss harvesting, charitable gifting, exchange funds, and long/short equity strategies that may be considered following a business sale or other significant liquidity event.

Larry and Angela discuss:

  • How taxes can influence investment selection and placement across different account types
  • Ways to address highly appreciated stock while considering diversification and taxable gains
  • How direct indexing may create additional opportunities to capture investment losses
  • Options such as charitable gifting and exchange funds for managing concentrated holdings
  • How long/short equity strategies may help address gains associated with a business sale
  • And more!

Connect with Angela Berkosky:

Connect with Larry Heller: 

About Our Guest:

Angela Berkosky serves as director of investment strategy, working out of our Lancaster and Wyomissing, Pennsylvania, offices. She has more than 25 years of experience in the financial services industry, with a career rooted in disciplined investment strategy and long-term client outcomes.

Angela began working at Savant in 2023 when Domani Wealth joined the firm. At Domani, she served as partner and chief investment officer beginning in 2010. She led portfolio strategy and investment decision-making across client relationships. Earlier in her career, she worked as an investment officer at a trust company and began her professional path as an associate at a boutique investment bank.

She holds the Chartered Financial Analyst (CFA®) designation and remains actively involved in the profession as a member of both the CFA Institute and the CFA Society of Philadelphia. Her work reflects a commitment to rigorous analysis, thoughtful risk management, and aligning investment strategy with client goals and cash flow needs.

Angela also maintains strong ties to higher education. She serves on the advisory council for the Wood Honors College at Shippensburg University in Pennsylvania, where she mentors honors students and helps guide curriculum and program development. She also serves as secretary of the congregation council at St. John’s Evangelical Lutheran Church in Boyertown, Pennsylvania.

She earned a bachelor’s degree in business administration from Shippensburg University and a Master of Business Administration (MBA) from Lebanon Valley College in Annville, Pennsylvania.

An accomplished pianist, Angela lives in eastern Pennsylvania with her husband, Tom, and their family. They enjoy traveling, attending live concerts, and spending time with their collie, Samson.

Heller Wealth Management is now part of Savant Wealth Management. Savant is a Registered Investment Advisor. This content is provided for informational and educational purposes only and should not be construed as personalized investment advice.

Effective March 31, 2026, Heller Wealth Management joined Savant Wealth Management (“Savant”). A copy of Savant’s current written disclosure Brochure discussing our advisory services and fees is available at www.savantwealth.com/disclosure-brochures/

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From Portfolio Performance to Purposeful Retirement Planning (Ep. 208)

From Portfolio Performance to Purposeful Retirement Planning (Ep. 208)

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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 this episode, Larry Heller, CFP®, CDFA®, explains how to build a retirement plan around the life you want rather than letting investment returns drive your decisions. He shares how cash flow, time horizons, risk tolerance, tax planning, estate planning, and investment decisions can work together to support both near-term needs and long-term priorities.

Larry discusses:

  • Why retirement planning should begin with your goals, priorities, and vision for the years ahead
  • How different time horizons can influence the way short-term and long-term assets are invested
  • How creating a regular retirement paycheck can make the transition away from employment income feel more familiar
  • Why taxes, Roth conversions, beneficiary designations, insurance, and estate planning need to be coordinated
  • How retirement progress can be measured by lifestyle, financial flexibility, family priorities, and long-term goals
  • And more!

Connect with Larry Heller: 

Heller Wealth Management is now part of Savant Wealth Management. Savant is a Registered Investment Advisor. This content is provided for informational and educational purposes only and should not be construed as personalized investment advice.

Effective March 31, 2026, Heller Wealth Management joined Savant Wealth Management (“Savant”). A copy of Savant’s current written disclosure Brochure discussing our advisory services and fees is available at www.savantwealth.com/disclosure-brochures/
200 Episodes of Retirement Unlocked: The Lessons That Matter Most (Ep. 200)

200 Episodes of Retirement Unlocked: The Lessons That Matter Most (Ep. 200)

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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’s lives. 

In this episode, Larry explores how he has always aimed to make financial planning more understandable as he continues to stay ahead of constant changes in tax laws, and retirement strategies. He expresses gratitude to his listeners, clients, and guests who have helped the podcast grow to nearly 50,000 YouTube views as it continues into its next chapter. 

Larry Heller, CFP®, CDFA®, discusses:

  • How Retirement Unlocked has changed over the years
  • Why retirement planning is more about cash flow than net worth
  • How taxes can become more complicated in retirement
  • Why financial planning should evolve as life changes
  • And more!

Connect with Larry Heller: 

Heller Wealth Management is now part of Savant Wealth Management. Savant is a Registered Investment Advisor. This content is provided for informational and educational purposes only and should not be construed as personalized investment advice.

Effective March 31, 2026, Heller Wealth Management joined Savant Wealth Management (“Savant”). A copy of Savant’s current written disclosure Brochure discussing our advisory services and fees is available at www.savantwealth.com/disclosure-brochures/
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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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.