Retirement Road Map

Derek Gregoire, Keith Ellis, and Matthew Peck
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Welcome to the Retirement Road Map by SHP Financial—a podcast empowering today's retirees and pre-retirees to make well-informed financial decisions that will help you spend more time living and dreaming, than worrying and wondering. Join SHP Financial Co-Founders Derek Gregoire, Keith Ellis, and Matthew Peck, CFP® CIMA®, as they share actionable financial strategies and insights, as well as interview top thought leaders in the world of finance, accounting, and estate planning. The SHP trademarked Retirement Road Map is a holistic planning process that focuses on the 5 key areas of retirement planning: Income planning, investment planning, tax planning, health care planning, and legacy planning. The Retirement Road Map is your guide to financial freedom and will prepare you for the retirement you've always dreamed of and deserve!

  1. 21 HRS AGO

    The Retirement Planning Mistakes That Could Cost You Thousands in Taxes with Alina Osokhovska

    Without a comprehensive financial plan that accounts for taxes, income strategies, and long-term goals, it's easy to overlook opportunities that could significantly impact your financial future. The reality is that even strong investment returns can be undermined by inefficient planning, leading to unnecessary taxes, missed opportunities, and less control in retirement. In this episode, Derek Gregoire is joined by Alina Osokhovska, Certified Financial Planner™, to explore the true role of financial planning and why it goes far beyond portfolio management. With deep expertise in tax strategies and long-term planning, Alina shares how thoughtful, proactive planning can help clients align their investments with their goals while navigating an ever-changing financial landscape. Together, they break down the different types of tax-advantaged accounts, including pre-tax, Roth, and after-tax strategies, and explain how each can play a role in building a more efficient retirement plan.  They also discuss the importance of tax diversification, how accounts like 401(k)s, IRAs, 529 plans, and HSAs fit into a broader strategy, and why ongoing planning is essential to adapt to changes in tax laws and personal circumstances.  In this podcast interview, you'll learn: Why financial planning goes far beyond investments and serves as the foundation for reaching your long-term goals. How pre-tax, Roth, and after-tax accounts differ and how each impacts your taxes in retirement. Why tax diversification is critical to maintaining flexibility and minimizing unnecessary taxes over time. How inefficient tax planning can reduce your retirement income just as much as market losses. The role of accounts like 401(k)s, 529 plans, and HSAs within a comprehensive financial strategy. Why financial planning is an ongoing process that must adapt to changes in tax laws, income, and personal goals.  Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

    31 min

  2. APR 22

    How to Maximize Your 401(k) and Avoid Common Mistakes in Retirement with Raphael Hanna

    For many people, investing money into a 401(k) is the foundation of their retirement. Unfortunately, most investors don't fully understand how these plans work or how to take full advantage of them. From contribution limits to employer matches and tax strategies, small decisions made today can have a significant impact on your long-term financial future. Without a clear understanding, it's easy to miss opportunities and make costly mistakes that could affect your income in retirement. In this episode, SHP co-founder Matthew Peck is once again joined by SHP's Raphael Hanna to break down the fundamentals of 401(k) planning. With years of experience helping clients navigate retirement strategies, Raphael shares practical insights into how these plans function and how to approach them with a long-term perspective. Together, they walk through the key components of a 401(k), including how to determine your contribution amount, how employer matching and vesting schedules work, and the differences between pre-tax and Roth contributions. They highlight common pitfalls to avoid and how proactive planning can help you maximize your retirement savings, giving you greater confidence as you approach retirement. In this podcast interview, you'll learn: The importance of fully understanding your 401(k) as it has replaced traditional pensions for many people. How to determine the right contribution amount based on your income, expenses, and long-term goals. How employer matching and vesting schedules work and why leaving early could mean losing valuable benefits. The key differences between pre-tax and Roth 401(k) contributions and how each impacts your taxes over time. Why tax diversification across pre-tax, Roth, and after-tax accounts can provide more flexibility in retirement. What to consider when rolling over a 401(k) or using in-service distributions to gain more control over your investments. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

    38 min

  3. APR 8

    Matt's Markets on the Move Q1: April 2026

    SHP Financial Co-Founder, Matt Peck, CFP®, CIMA®, and Lead Advisor, Laura Russo, sit down for their quarterly market update. Matt and Laura will take a look back at Q1, discuss the current state of the markets, where we are headed, and what this means for your future and finances. They'll also address key questions submitted by our clients. Visit shpfinancial.com for more information!

    31 min

  4. APR 8

    Financial Planning Tools & Strategies For Every Stage of Life with Chris Willis

    Financial planning is a lifelong process that evolves with each stage of life. Yet many people either start too late or focus on the wrong priorities and miss key opportunities that could significantly impact their long-term financial success. Without a clear roadmap, it's easy to overlook critical strategies that compound over time. Today, Derek Gregoire is joined by SHP Financial Advisor Chris Willis to walk through the financial priorities everyone should consider at each stage of life. From early investing habits to retirement income strategies, Chris shares practical insights drawn from both his own experience and working with clients across multiple generations. Together, they discuss several key strategies, including leveraging compound interest early, optimizing tax efficiency in your 40s and 50s, and navigating critical retirement milestones such as Social Security, Medicare, and required minimum distributions. Throughout the conversation, they highlight the importance of proactive planning at every stage, which helps build wealth, reduce stress, and create a more confident path as you approach retirement. In this podcast interview, you'll learn: Why investing early creates a massive long-term advantage and how small monthly contributions can grow into significant wealth over time. Why investing in yourself can increase your long-term earning potential. The key financial priorities to focus on in each stage of life. The importance of life insurance and estate planning to protect your family's future. Why tax planning becomes critical in your 40s and 50s and the importance of diversifying your assets from a tax perspective. How Social Security timing impacts your overall retirement plan and strategies to reduce taxes on retirement income and distributions Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

    34 min

  5. MAR 18

    The Most Important Lessons We've Learned After 20+ Years of Financial Planning

    With over 20 years of financial planning experience and having helped thousands of retirees and pre-retirees successfully plan for retirement, we've learned which planning mistakes can derail retirement and which strategies help clients retire with confidence and peace of mind. In this very special episode, SHP Financial's co-founders Derek Gregoire, Keith Ellis Jr., and Matthew Peck reflect on the biggest lessons they've learned after 100 podcasts and all the years of building a successful wealth management firm.  From evolving investment strategies to the growing importance of tax planning and behavioral finance, they share insights from both their professional experience in the industry and in conversations with past guests. They discuss how retirement planning has shifted from focusing solely on income to a comprehensive approach that includes tax efficiency, risk management, healthcare, estate planning, and charitable giving. They also offer practical advice on avoiding mistakes, handling market volatility, and building a retirement plan that ensures financial security and peace of mind. In this podcast interview, you'll learn: How retirement planning has evolved beyond just income strategies. Why understanding and managing investment volatility is critical in retirement. The importance of tax diversification across pre-tax, Roth, and after-tax accounts. Lessons retirees often learn too late about required minimum distributions and taxes. How behavioral biases like overconfidence can impact long-term investment success. Why comprehensive planning is more powerful than managing investments alone. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

    39 min

  6. MAR 4

    Smart College Planning Strategies for Parents and Grandparents with Laura Russo

    Planning for retirement doesn't always stop with your own financial future. For many families, helping children or grandchildren afford a college education has become one of the biggest priorities facing retirees and pre-retirees.  With rising tuition costs, evolving financial aid rules, and widespread misconceptions around 529 plans and FAFSA, families with great intentions can unknowingly make costly mistakes without the right strategy in place. In this episode, Matthew Peck is joined by SHP Financial Advisor Laura Russo to break down the increasingly complex world of college planning. Laura explains how parents and grandparents can support their family's education goals in ways that remain tax-efficient and how ownership structures, gifting strategies, and early planning decisions can influence outcomes for both students and families. Together, they share practical strategies such as direct tuition payments, 529 and ABLE accounts, and recent FAFSA rule changes that significantly impact financial aid eligibility. Ultimately, this conversation emphasizes how education planning is done proactively, it can reduce financial stress, preserve family wealth, and create opportunities for future generations without compromising retirement security. In this podcast interview, you'll learn: How grandparents can help fund college in a tax-efficient way. Why 529 plan ownership now matters more than ever. How recent FAFSA changes impact financial aid eligibility. The differences between direct tuition payments and 529 strategies. Why student-owned assets can unintentionally reduce aid opportunities. How ABLE accounts support education planning for individuals with disabilities. Why early financial conversations help families make smarter college decisions. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

    43 min

  7. FEB 18

    New Estate Planning Laws and Trends You Need to Know in 2026 with Keith McManus

    Planning for the future doesn't stop once your estate documents are signed. As laws change, family dynamics evolve, and asset values grow, outdated estate plans can create unintended consequences. In this episode, Keith Ellis Jr. is joined by estate planning attorney Keith McManus to discuss current estate planning trends, common misconceptions, and the real risks families face when plans aren't properly reviewed. With over 30 years of experience, Keith McManus explains why estate planning is never a one-and-done decision and why proactive updates matter more than most people realize. Together, they explore how blended families, beneficiary designations, and state-specific tax laws can dramatically impact outcomes, along with why trusts don't all work the same way. Keith also addresses the growing trend of DIY and AI-generated estate plans and the costly mistakes that often follow. In this podcast interview, you'll learn: The importance of reviewing estate plans every three to four years. How blended families create unique estate planning challenges. What the Massachusetts estate tax exemption means for retirees. How beneficiary designations can override trusts. Why long-term care planning should be factored into your estate planning. Reasons why DIY and AI-generated estate plans can create serious risks. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

    26 min

  8. FEB 4

    The Most Common Questions Pre-Retirees Have About Retirement with Mike Guthrie

    Mentally preparing for retirement often generates more questions than answers. From wondering if you've saved enough to figuring out when you can finally stop working, many pre-retirees feel uncertain about what comes next. And then you add concerns around taxes, healthcare, Social Security, and market volatility, and it's easy to feel overwhelmed without a clear plan in place. In this episode, Keith Ellis Jr. is joined by SHP Financial Advisor Mike Guthrie to tackle the most common questions they've heard from clients over the years. With decades of combined experience, Keith and Mike walk through real-world scenarios and explain why there's rarely a one-size-fits-all answer—but there's always a better, more informed way to make decisions. They discuss how to determine whether you truly have enough to retire, how income planning provides clarity and confidence, and why understanding where your money comes from—and where it goes—is critical in retirement. You'll also hear how concepts like the 4% rule and income buckets help retirees move from uncertainty to control. Ultimately, Keith and Mike emphasize the importance of proactive planning—especially around taxes and withdrawal strategies—so retirees can protect their lifestyle, reduce unnecessary risk, and enjoy the years they've worked so hard for. In this podcast interview, you'll learn: How to determine whether you truly have enough money to retire. Why income planning is the foundation of a confident retirement. When it may—or may not—make sense to retire earlier than expected. How to think about cash reserves, income buckets, and long-term growth. What to consider when deciding when to claim Social Security. Why proactive tax planning can significantly impact retirement success. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

    34 min
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About

Welcome to the Retirement Road Map by SHP Financial—a podcast empowering today's retirees and pre-retirees to make well-informed financial decisions that will help you spend more time living and dreaming, than worrying and wondering. Join SHP Financial Co-Founders Derek Gregoire, Keith Ellis, and Matthew Peck, CFP® CIMA®, as they share actionable financial strategies and insights, as well as interview top thought leaders in the world of finance, accounting, and estate planning. The SHP trademarked Retirement Road Map is a holistic planning process that focuses on the 5 key areas of retirement planning: Income planning, investment planning, tax planning, health care planning, and legacy planning. The Retirement Road Map is your guide to financial freedom and will prepare you for the retirement you've always dreamed of and deserve!

Information

  • Creator
    Derek Gregoire, Keith Ellis, and Matthew Peck
  • Years Active
    2021 - 2026
  • Episodes
    116
  • Rating
    Clean
  • Copyright
    © 2021 SHP Financial
  • Show Website
    Retirement Road Map

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