Tag: Retirement Planning

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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:

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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:

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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:

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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.

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Understanding the Insurance Market Crisis: Higher Rates, Tougher Carriers, and Smart Moves with Gregg Knepper [Ep.174]

Understanding the Insurance Market Crisis: Higher Rates, Tougher Carriers, and Smart Moves with Gregg Knepper [Ep.174]

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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]
  • And more!

Connect with Gregg Knepper:

Connect with Larry Heller: 

About Our Guest:

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.

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5 Tax Gotchas That High-Net-Worth Individuals Overlook [Ep.173]

5 Tax Gotchas That High-Net-Worth Individuals Overlook [Ep.173]

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What tax traps could derail your retirement plans? 

In this episode, Larry Heller, CFP®, CDFA®, breaks down five major tax “gotchas” that high-net-worth retirees must navigate to protect their wealth and retirement security.

From the impact of required minimum distributions to the looming expiration of the 2017 tax cuts, Larry sheds light on often-overlooked tax challenges. He also explores strategic solutions like Roth conversions and income planning to help retirees minimize surprises and maximize financial confidence.

Key episode discussions include:

  • Required Minimum Distributions (RMDs) and their tax impact [03:09]
  • Expiration of the 2017 Tax Cuts and Job Act [04:04]
  • The “Widow Penalty” and implications for single retirees [07:37]
  • Gifting strategies and estate planning considerations [10:03]
  • The consequences of leaving large IRAs to children [11:05]
  • And more!

Connect with Larry Heller: 

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Retirement Unlocked: Managing Sequence of Returns Risk [Ep.171]

Retirement Unlocked: Managing Sequence of Returns Risk [Ep.171]

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What does it mean to face the ‘sequence of returns risk’ when you retire?

In this episode of Retirement Unlocked, Larry Heller, CFP®, CDFA®, discusses why the order of your investment returns matters as you enter retirement. Larry also breaks down this critical aspect of retirement planning and introduces strategies that can safeguard your financial future.

Key episode discussion points include:

  • The shift from “Life Unlimited” to “Retirement Unlocked”
  • How the sequence of returns can impact retirees 
  • Historical examples of sequence of returns risk
  • The reservoir strategy for mitigating those risks
  • Insights on adjusting your withdrawal strategy 
  • Behavioral finance and the psychological aspects of investing 
  • And more!

Resources: 

Connect with Larry Heller: 

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Mastering Retirement Withdrawals: Expert Tips for Smart Distribution Planning [Ep. 169]

Mastering Retirement Withdrawals: Expert Tips for Smart Distribution Planning [Ep. 169]

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Do you know the smartest way to manage your withdrawals in retirement?

In this episode of the Life Unlimited podcast, host Larry Heller, CFP®, CDFA®, shares expert strategies for managing retirement withdrawals to ensure financial stability and tax efficiency. 

Larry covers essential steps for building a smart distribution plan, emphasizing pre-retirement planning and proactive wealth management. The episode explores the benefits of Roth conversions, the impact of the Secure 2.0 Act, and critical topics such as the widow penalty, annuities, and estate planning, all supported by real client insights.

Whether you’re approaching retirement or already retired, this episode offers practical tips to help you minimize taxes, optimize withdrawals, and protect your wealth and legacy. Don’t miss this valuable guide to mastering your retirement finances!

Key episode discussions include:

  • Strategic tax planning to minimize taxes before the distribution phase
  • Understanding different income streams like Social Security, pensions, and retirement accounts 
  • Real client scenarios illustrating the impact of effective and missed strategies
  • The effects of federal and state estate taxes, plus planning for longevity
  • Integrating attorneys and other professionals for a holistic financial plan 
  • And more!

Resources: 

Connect with Larry Heller: 

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Beyond Accumulation: Mastering Your Retirement Distribution Strategy [Ep. 164]

Beyond Accumulation: Mastering Your Retirement Distribution Strategy [Ep. 164]

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Retirement isn’t just about accumulating wealth – it’s about making sure it lasts. 

In this episode, Larry Heller, CFP®, CDFA®, explores the essential elements of a well-rounded distribution strategy for retirement, including guiding you through five key areas every retiree should prioritize: income vs. total return, tax management, investment allocation, longevity, and estate planning.

Larry dives deep into the shift from accumulation to distribution, revealing strategies to help retirees sustain income, reduce taxes, and cover health expenses—all while preparing a meaningful legacy. With a focus on turning retirement into a financially secure and fulfilling stage of life, this episode provides actionable advice on balancing your immediate needs with a long-term vision.

Whether you’re entering retirement or aiming to enhance your financial strategy, this episode will equip you with the tools and mindset to enjoy a confident and comfortable retirement.

Key Points Covered:

  • Combining income sources like Social Security, pensions, and investments to balance retirement income and comfort
  • Reducing tax burdens through Roth conversions and managing required minimum distributions (RMDs) under the latest Secure Act changes
  • Using the “reservoir strategy” to balance cash, bonds, and equities for steady income and minimized risk
  • Addressing healthcare and long-term care costs to protect assets and maintain financial stability
  • Aligning estate plans with tax strategies to maximize inheritance for heirs
  • And much more!

Actionable Takeaway: Review your retirement plan to ensure it supports your lifestyle, reduces tax impacts, and aligns with your legacy goals. Consult a financial planner to tailor it to your unique needs for a fulfilling retirement.

 

Resources:

Connect with Larry Heller: