Retirement Road Map

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!

091: Estate Planning Essentials: How Trusts & Gifting Protect Your Legacy with Attorney David Chaves 11/12/2025

090: Going Beyond the Portfolio: Transitioning Into Retirement with Confidence with Kyle Britton 10/29/2025

Matt's Markets on the Move Q3: October 2025 10/10/2025

089: The Future of Fannie Mae and Freddie Mac and What Privatization Could Mean for Homebuyers with Nathan Hartseil 10/08/2025

089: The Future of Fannie Mae and Freddie Mac and What Privatization Could Mean for Homebuyers with Nathan Hartseil The housing market has undergone significant changes in recent years, leaving many homeowners and prospective buyers feeling uncertain about its future direction. Interest rates have risen from historic lows, making affordability a pressing issue, and discussions about the possible privatization of Fannie Mae and Freddie Mac are sparking new concerns about the future of housing and mortgages in America. In this episode, we welcome back Nathan Hartseil of Main Street Home Loans. Nate explains the complex role of Fannie Mae and Freddie Mac in the housing market, including how they provide liquidity and stability, why they have remained under government conservatorship since 2008, and what could happen if they were to transition to private control. From the potential impact on interest rates and borrowing standards to how privatization could shape opportunities for first-time buyers, investors, and empty nesters, Nate shares his thoughts and insights into how this shift could affect anyone who may need mortgage financing in the near future. Whether you’re considering buying your first home, refinancing, or making a change in retirement, this conversation sheds light on a pivotal topic that could redefine the housing landscape for years to come. In this podcast interview, you’ll learn: Why Fannie Mae and Freddie Mac were placed under government conservatorship in 2008 and their role in stabilizing the housing market. How privatization could impact mortgage rates for both borrowers with healthy and unhealthy credit scores. The effect of higher interest rates on affordability, refinancing, and downsizing decisions. What the return and popularity of non-qualified mortgages means for today’s lending environment. The innovation and challenges that competition from private investors could bring to the mortgage industry. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/38450730

088: The Importance of Retirement Planning for Women and Widows with Alina Osokhovska, CFP® 09/24/2025

088: The Importance of Retirement Planning for Women and Widows with Alina Osokhovska, CFP® Losing a spouse is one of life’s most painful experiences, and in the midst of grief, surviving partners are often faced with overwhelming financial decisions. From settling estates to adjusting to changes in income, the process can feel like an impossible burden to carry alone. Without a plan in place, surviving spouses may find themselves vulnerable to financial missteps at a time when clarity is hardest to find. In this episode, SHP Financial’s Derek Gregoire is joined by Planning Advisor Alina Osokhovska, CFP® to explore the critical importance of financial planning for widows. With years of experience guiding families through difficult transitions, Alina explains how proper planning can bring stability, reduce stress, and provide widows with the confidence to focus on healing rather than paperwork. In this conversation, Derek and Alina unpack the key financial considerations after the loss of a spouse, from estate settlement and tax bracket changes to Social Security benefits and cash flow adjustments. They also discuss proactive strategies for couples to ensure that if the unthinkable happens, surviving spouses are not left unprotected. Whether you are preparing for the future or currently walking through loss, this episode offers compassionate guidance and practical steps to ease the burden during one of life’s most difficult transitions. In this podcast interview, you’ll learn: Why women are statistically more likely to become widows and the financial challenges that come with it. The critical first steps when settling an estate after the loss of a spouse. How income and cash flow change when pensions, Social Security, or other benefits are reduced or lost. The hidden tax consequences widows often face and how proactive planning can help mitigate them. Advanced planning strategies for couples, including estate exemptions, step-up in basis, and inherited IRA considerations. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/38300515

087: How Death Doulas Help Families Navigate End-of-Life with Love & Compassion with Aimee Yawnick 09/10/2025

087: How Death Doulas Help Families Navigate End-of-Life with Love & Compassion with Aimee Yawnick Death is one of life’s certainties, yet it remains one of the hardest subjects to talk about. Many families avoid end-of-life conversations out of fear, discomfort, or superstition. Unfortunately, this avoidance can lead to increased stress, resentment, and regret when the time comes to make critical decisions. So how do we make the process smoother, less overwhelming, and more meaningful? In this episode, Matthew Peck is joined by Aimee Yawnick, a practicing death doula and founder of Leaving in Love. Drawing from her personal journey, Aimee shares what it means to “hold space” at the end-of-life, how to navigate powerful emotions such as grief, guilt, and even relief, and why these conversations are the greatest gift we can give to loved ones. We also discussed Aimee’s six-week course, What Matters Most, which guides participants through a process of envisioning their final 90 days. From legacy letters and videos to healing old relationships, Aimee explains how facing mortality can change the way we live — and not just how we prepare to die. Whether you’re in retirement, caring for an aging loved one, or looking for ways to get started with end-of-life planning, this conversation has a ton of valuable insights that will help you and others navigate this challenging aspect of life and death. In this podcast interview, you’ll learn: What a death doula is and the value they add for families. Why avoiding conversations about death often creates a bigger burden for loved ones. How “holding space” provides comfort and calm during life’s most difficult moments. The importance of legacy planning through letters, videos, and rituals. How the What Matters Most course helps people align values with end-of-life decisions. Why planning early and before a crisis leads to greater peace of mind. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/38097085

086: Career Insights for New Grads Aspiring to Become Financial Advisors with Raphael Hanna 08/20/2025

086: Career Insights for New Grads Aspiring to Become Financial Advisors with Raphael Hanna Graduation marks an exciting new chapter for young professionals, but for those eyeing a career in financial planning, the path forward can feel uncertain. What are the skills that investment firms are looking for? Which licenses and designations matter most? And how do you land that first opportunity in a highly competitive field? Today, Matthew Peck welcomes back returning guest Raphael Hanna to share his journey from Stonehill College to SHP Financial. Drawing from his own early experiences, Raphael reveals how internships, networking, and a willingness to adapt shaped his career path. He also explains the difference between independent advisory firms and other industry models, why relationship-building is as important as technical skills, and how to decide where you want to specialize. In this conversation, you’ll learn the difference between independent advisory firms and other industry models, why relationship-building is as important as technical skills, and how to decide where you want to specialize. Whether you’re a recent grad, a career changer, or simply curious about what it takes to thrive in financial planning, this episode provides a blueprint to start off on the right track and build a career that lasts. In this podcast interview, you’ll learn: Why networking can make or break your early career. The important licenses every new advisor should consider obtaining. How to choose the right firm for your career goals. The pros and cons of independent vs. traditional advisory models. How professional designations like the CFP® can set you apart. The best ways to explore career paths within financial services. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/37851855

085: How Donor-Advised Funds Simplifies Charitable Giving And Maximizes Tax Benefits with Kyle Casserino 08/06/2025

085: How Donor-Advised Funds Simplifies Charitable Giving And Maximizes Tax Benefits with Kyle Casserino Many retirees want to give back—but aren’t sure how to do it in a way that’s financially savvy and tax-efficient. If you’ve ever wondered how to streamline your charitable giving, take advantage of smart tax strategies, or leave a lasting legacy without the administrative burden, we have the perfect guest to help with those important decisions. Today, Matthew Peck is joined by Kyle Casserino, VP of Charitable Planning at Fidelity Investments. With years of experience in philanthropic financial strategies, Kyle walks us through the fast-growing world of Donor-Advised Funds (DAFs) and how they can help individuals make a greater impact while minimizing taxes. From understanding the history and purpose of DAFs to exploring real-life scenarios where they make the most sense, Kyle explains why this tool is increasingly popular among charitably inclined investors. In this conversation, you’ll learn how Donor-Advised Funds compare to private foundations, how to give appreciated assets like stocks instead of cash, and why these accounts are especially valuable for high-income earners, business owners, and those with large tax events. Whether you’re already giving or planning to give in the future, you’ll walk away with actionable strategies to make your charitable dollars go further. In this podcast interview, you’ll learn: Why Donor-Advised Funds are a flexible, low-maintenance alternative to private foundations. How giving appreciated stock can help you avoid capital gains taxes. The advantages of funding a DAF in high-income years to "pre-pay" future giving. Why Donor-Advised Funds can help simplify record-keeping and tax filing. How DAFs support legacy planning, including multi-generational giving. The biggest differentiators of foundations versus Donor-Advised Funds Why timing, tax brackets, and estate size matter when planning charitable gifts. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/37656205

084: Examining the Big Beautiful Tax Bill & What it Means for Your Retirement with Alina Osokhovska 07/23/2025

Matt's Markets on the Move Q2: July 2025 07/11/2025

083: Smart Tax Planning Strategies to Keep More of Your Retirement Income with Mike Guthrie 07/02/2025

083: Smart Tax Planning Strategies to Keep More of Your Retirement Income with Mike Guthrie Most retirees are surprised to learn just how differently their income is taxed once they stop working. From Social Security to pensions, IRAs, dividends, and even rental income, retirement brings a complex new tax landscape that can catch even the most financially savvy off guard. This episode is here to help you stay ahead of the curve. Joining SHP Financial's Matthew Peck is returning guest and financial advisor Mike Guthrie. With over 25 years in the industry, Mike breaks down the different sources of retirement income and how each is taxed—from qualified accounts, such as 401(k)s and IRAs, to brokerage accounts, Roth IRAs, and beyond. He highlights the common pitfalls people often fall into and why proactive planning is essential to avoid unpleasant tax surprises. By the end of this conversation, you’ll have a clearer understanding of how tax buckets work, which withholding tax strategies make sense, and how tax laws can impact everything from Social Security to capital gains. Whether you're planning for retirement or already there, this conversation will help you navigate retirement income with more confidence, control and peace of mind. In this podcast interview, you’ll learn: Why not all retirement income is taxed the same—and how to plan accordingly. How interest, dividends, capital gains, and Roth withdrawals differ in tax treatment. What you can (and can’t) withhold taxes from in retirement. The importance of proactive tax planning in avoiding April surprises. How strategies like Roth conversions, gifting, and timing Social Security can reduce your tax burden. Why personalized advice is critical because no two retirees face the same tax situations. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/37156100

082: How SMAs Help Optimize Tax Efficiency In Your Portfolio with Cam Iarrobino 06/18/2025

082: How SMAs Help Optimize Tax Efficiency In Your Portfolio with Cam Iarrobino Perhaps you’ve heard of Separately Managed Accounts (SMAs) but aren’t quite sure how they work or if they’re only suitable for high-net-worth investors. In this episode, we’ll break down the truth behind SMAs and why more investors are turning to them as a way to gain control, improve tax efficiency, and tailor their portfolios to their unique financial goals. In today’s podcast, SHP Financial’s Matthew Peck is joined by Cam Iarrobino, Investment Analyst to explain how SMAs differ from traditional mutual funds and ETFs, and why they’ve gained traction in today’s complex market environment. They’ll walk you through the key benefits of SMAs—including transparency, customization, and after-tax yield—and how they can be used to align investment strategies with a client’s overall retirement plan. In this conversation, you’ll learn the key benefits of SMAs—including customization and after-tax yield—and how they can be used to align investment strategies with a client’s overall retirement plan. You’ll also learn the importance of rebalancing, direct indexing your investments, and how to know when SMAs are (or aren’t) the right fit for you. In this podcast interview, you’ll learn: How SMAs offer greater customization and control compared to mutual funds and ETFs. The increased flexibility and efficiency of direct indexing and tax-loss harvesting with SMAs. The advantages of incorporating municipal bonds with SMAs and why their favored by SHP Financial. The value of tax efficiencies and after-tax yield benefits of SMAs, especially for high-net-worth investors. The difference between SMAs, ETFs and mutual funds with minimums, fees and flexibility. How SHP Financial evaluates how to implement SMAs into their client portfolios. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/37019210

081: How the 2025 Social Security Reforms Will Impact Retirees with Chase Reardon 06/04/2025

080: How Financial Plans Help Navigate Volatile Markets and Create Peace of Mind with Kyle Britton 05/21/2025

080: How Financial Plans Help Navigate Volatile Markets and Create Peace of Mind with Kyle Britton In times like these, when there's market volatility and financial insecurity, it's more important than ever to have a financial plan to know that you can weather the storm and wild swings in the markets. It's the difference between having a plan vs just having a portfolio. In today's episode, Derek Gregoire is joined by SHP Financial's Lead Advisor, Kyle Britton, to discuss how they're helping their clients navigate the emotions of investing during bear markets. While many people would assume that the phones are ringing off the hook with clients filled with panic, you'll hear why that might be the exception rather than the rule because of the methods SHP Financial uses to build comprehensive financial plans that help their clients prepare for these very moments. In this conversation, they discussed how SHP helps clients determine their risk score and how they stress test portfolios to demonstrate the outcomes of down years. They'll explain what sequence of returns risk means and how important it is for investors to understand it as they approach retirement. They'll also discuss how bear markets create opportunities for those who have time on their side to weather the storm and take full advantage when the recovery happens. In this podcast interview, you’ll learn: What sequence of returns risk is and how SHP helps to calculate risk in your portfolio The benefits of using tools like Riskalyze to analyze the risk in your portfolio. How the news and media can make market volatility feel worse than it is by leaning on the chaos and negativity. The three bucket strategy that SHP uses to protect your annual income and long-term growth investments. How quickly market recoveries happen and the opportunities that bear markets can create. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/36634090

079: How Practicing Gratitude Builds Deeper Connections and Relationships with John Israel 05/07/2025

079: How Practicing Gratitude Builds Deeper Connections and Relationships with John Israel Many people nearing retirement focus on their portfolios but neglect one of the most important components of a fulfilling life—genuine human connection. Especially in today’s world, where negativity dominates the headlines and technology often replaces personal interactions, gratitude can help us build more meaningful relationships and improve our well-being. In this episode, SHP Financial’s Derek Gregoire and Matthew Peck welcome keynote speaker, author, and professional gift giver John Israel—also known as Mr. Thank You. After launching a social experiment in which he hand-wrote five thank-you cards a day for a year, John uncovered profound insights into how deeper human connections are all about feeling seen, safe, and supported. His Mr. Thank You Project has since inspired thousands of people and companies to create cultures of gratitude and authenticity. In our conversation, you’ll hear the science behind why it’s easy to focus on the negative, how vulnerability leads to stronger relationships, and how you can use gratitude—even in tough times—to unlock personal and business growth and foster deeper connections. John offers a refreshing perspective on the little things that can make a huge impact. In this podcast interview, you’ll learn: Why gratitude is a learned skill—and how to practice it daily How handwritten thank-you notes transformed John’s personal and professional life The hierarchy of human connection and cornerstones of deeper relationships How to find meaning and purpose—even in life’s most painful experiences The ways SHP builds authentic, long-lasting client relationships through service and care Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/36446420

078: Tax-Efficient Financial Planning Strategies for High-Net-Worth Investors with Alina Osokhovska 04/23/2025

077: Estate Planning Essentials to Help Protect Your Assets and Legacy with Matthew Karr, ESQ 04/09/2025

077: Estate Planning Essentials to Help Protect Your Assets and Legacy with Matthew Karr, ESQ Estate planning is arguably the most important of the five areas of financial planning. When protecting your legacy, having a comprehensive financial plan is only half the battle. Without the proper legal documents—wills, trusts, powers of attorney—you risk leaving behind confusion, the lengthy probate court process, and unintended tax burdens for your loved ones. Today’s episode features “Two Matts” as SHP Financial co-founder Matthew Peck welcomes Matthew Karr back to the podcast. Matt Karr is the founder and principal attorney of the Heritage Law Center in Woburn, Massachusetts, who’s been a tremendous resource and ally for us and our clients for many years. With more than 15 years of experience in estate planning and elder law, Matt Karr has helped countless families ensure their wishes are fulfilled and their wealth and legacy are protected. You’ll hear Matt Karr break down the differences between wills and trusts, the benefits of using irrevocable trusts for asset protection, and actionable tips to help your beneficiaries avoid probate court when planning your estate. You’ll also learn valuable insights for safely and securely storing your estate documents and why working with an attorney will help your loved ones settle your affairs the way you intended. In this podcast interview, you’ll learn: The key differences between wills and revocable vs. irrevocable trusts—and when each is appropriate. How irrevocable trusts can help protect your assets from lawsuits, creditors, and nursing home costs. Why the 30 day waiting period is necessary prior to starting the estate process. How unsecured debts that credit card bills and some medical bills are treated in an estate without sufficient assets. The importance of retaining original copies of estate documents and tips for storing them in a secure but accessible way. Why reviewing and updating your estate plan regularly is essential as laws, assets, and life circumstances evolve. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/36030725

Matt's Markets on the Move: April 2025 04/04/2025

076: How The AI Revolution Is Transforming Business, Investing and Daily Life with BlackRock’s Jay Jacobs 03/26/2025

076: How The AI Revolution Is Transforming Business, Investing and Daily Life with BlackRock’s Jay Jacobs Artificial Intelligence (AI) is no longer a futuristic concept—it’s here, and its transforming industries, investments, and daily life. Despite the advantages in processing and productivity, many still have concerns about using AI in their everyday lives at home and in business. This begs the question: Should AI be something we fear, or is it just new technology that we should embrace? Here to help answer those questions is Jay Jacobs. Jay is BlackRock’s Head of Thematic and Active ETFs, where he oversees the overall product strategy, thought leadership, and client engagement for the firm’s thematic and active ETF businesses. We’re thrilled to tap into his expertise to break down the evolution of AI and LLMs (Large Language Models), how it’s impacting the investment landscape, and what the future looks like in the AI and digital world. In our conversation, we discussed the rapid development of artificial intelligence and its potential to revolutionize sectors like finance, healthcare, and even customer service. You’ll also hear Jay describe how AI has evolved into a race toward Artificial General Intelligence (AGI), its ability to increase our productivity on a personal level, and whether the fears surrounding AI’s risks are warranted. In this podcast interview, you’ll learn: How AI has evolved from Clippy in Microsoft Word to ChatGPT and other LLMs. Why research and investing in AI is accelerating and what’s fueling its rapid growth. Why access to data, computing power, and infrastructure are the new competitive advantages in the AI arms race. How businesses are leveraging AI to boost efficiency and customer service. The race to AGI (Artificial General Intelligence)—what it means and how close we really are. How synthetic data and virtual environments are shaping the next frontier of AI development Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/35826100

075: Tips and Strategies for Navigating the Loss of a Spouse with Laura Russo 03/12/2025

074: Tax Planning Strategies to Help Preserve Your Money in Retirement with Peter Roache, CPA 02/26/2025

073: Small Estate Planning Mistakes That Have a Massive Impact On Your Legacy with Keith McManus 02/12/2025

072: Navigating the Emerging Asset Class of Bitcoin and Digital Assets with Ryan Lessard 01/29/2025

072: Navigating the Emerging Asset Class of Bitcoin and Digital Assets with Ryan Lessard Bitcoin and digital assets are among the most debated, complex, and controversial asset classes on the market today. Despite being a polarizing topic, nobody can deny their growing importance in global finance and even in Trump's administration in the White House. That's why we're thrilled to have Ryan Lessard, a Digital Asset Strategist from Fidelity, on the podcast today. Ryan shares his expertise in this emerging asset class to unpack Bitcoin's unique characteristics, including its capped supply of 21 million coins, the blockchain technology behind it, and how it compares to traditional assets like gold. In our conversation, we discussed why Bitcoin has primarily appealed to younger investors and is particularly relevant in countries with economic instability and hyperinflation. We also explored Bitcoin's potential to diversify portfolios while addressing the challenges, the rapid pace of technological advancements, and the importance of staying curious and continually learning about this evolving space. Disclaimer: The information included in this material is for informational purposes only. SHP will not be held responsible for any detrimental reliance you place on this information. It is agreed that use of this information shall be on an "as is" basis and entirely at your own risk. In this podcast interview, you’ll learn: How Bitcoin combines decentralization and blockchain technology. How a capped supply ensures Bitcoin’s scarcity and ultimately, its value. Why younger investors are more likely to invest in digital assets. How Bitcoin offers stability in volatile economies. Crypto investing requires knowledge and caution and regulation is key for trust and growth. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit Connect With Us on Social /episode/index/show/retirementroadmap/id/35037685

071: A New Years Resolution to Retire With a Plan with Matthew Peck and Keith Ellis Jr. 01/15/2025

Matt's Markets on the Move: January 2025 01/10/2025

070: How Proactive Healthcare Planning Could Help Save Thousands in Retirement with Scott Hokanson 12/27/2024

069: Preparing for College Education: Making Sense of Student Loans, 529 Accounts and FAFSA with Mark Kenney 12/11/2024

068: Post-Election Market Update: What SHP Financial is Keeping an Eye On with Matthew Peck 11/27/2024

067: How Roth Conversions Help Reduce Income Taxes in Retirement with Nick Nelson 11/13/2024

066: How to Change the World in Retirement with Matt Glynn 10/30/2024

Retirement Road Map

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