For close to 10 years, SHP Financial co-founders Derek Gregoire, Matthew Peck and Keith Ellis have been hosting this weekly talk radio show with the mission of empowering today's retirees and pre-retirees, so you can make better financial decisions for your future. Each week you'll hear timely financial news and topics, along with local and national guest interviews, all geared towards helping you get to and through retirement. Click here to learn more. This page is sponsored by SHP Financial and does not reflect iHeartMedia, its employees or other advertisers.
Connect With SHP Financial
092: The Emergence of Private Equity, Private Credit & Alternatives with BlackRock's Jon Diorio
091: Estate Planning Essentials: How Trusts & Gifting Protect Your Legacy with Attorney David Chaves
For many families, estate planning creates a feeling of anxiety, which is a big reason why they put it off for another day. From probate costs to nursing home spend-downs, failing to plan can leave loved ones vulnerable to unnecessary taxes, legal fees, and stress.
In this episode, SHP's Laura Russo is joined by returning guest Attorney David Chaves to share actionable tips and strategies for reducing estate taxes. Dave discusses how his real-life experiences shaped his commitment to helping families secure their financial futures and preserve what they've worked for.
Together, they unpack the differences between revocable and irrevocable trusts, how often an estate plan should be updated, and effective ways to reduce your estate's value through gifting and education savings.
Whether you're protecting a family home or simply hoping to pass more to your loved ones, this episode will give you the clarity to take action now—before it's too late.
In this podcast interview, you'll learn:
- Why wills often guarantee probate and how trusts can help your family avoid it.
- The key differences between revocable and irrevocable trusts.
- How the Massachusetts estate tax exemption has changed and what it means going forward.
- The benefits of A-B trusts and how they preserve more of your wealth.
- How Charitable Remainder Trusts and gifting strategies can reduce taxes while building your legacy.
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
090: Going Beyond the Portfolio: Transitioning Into Retirement with Confidence with Kyle Britton
For most of your life, retirement planning has likely centered around saving and building wealth. But what happens when the paychecks stop and it's time to start replacing your income withdrawing from your retirement savings and investments?
In this episode, SHP Financial Co-Founder Derek Gregoire is joined by Kyle Britton, Lead Advisor at SHP Financial. Together, they explore what it truly means to go beyond the Xs and Os of investing and step into retirement with purpose, clarity, and confidence.
You'll hear Derek and Kyle talk about how the biggest retirement challenges are often psychological, not financial. They discuss why so many retirees struggle to give themselves permission to spend what they've earned, and how purpose and identity—two things often tied to careers—must be redefined as we enter this next phase of life.
Drawing from real client stories and recent research, Kyle highlights what truly drives happiness in retirement and how to create a plan that supports both your finances and your fulfillment.
In this podcast interview, you'll learn:
- Why retirement planning goes far beyond investments and tax strategies.
- The biggest psychological hurdle retirees face: giving themselves permission to spend.
- How to shift your mindset from "Do I have enough?" to "What's possible?" in retirement.
- The four key ingredients of a fulfilling retirement, according to a recent MassMutual study.
- How to redefine your purpose and legacy in the next chapter of your life.
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
Matt's Markets on the Move Q3: October 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 SHPfinancial.com/podcast
Connect With Us on Social
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 SHPfinancial.com/podcast
Connect With Us on Social
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 SHPfinancial.com/podcast
Connect With Us on Social
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 SHPfinancial.com/podcast
Connect With Us on Social
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 SHPfinancial.com/podcast
Connect With Us on Social
084: Examining the Big Beautiful Tax Bill & What it Means for Your Retirement with Alina Osokhovska
The "One Big Beautiful Bill Act" has just become law, bringing sweeping tax changes that will directly impact retirees and pre-retirees. From changes to itemized deductions and charitable giving to updates on Social Security taxation and estate planning, the impact is far-reaching.
Today, Matthew Peck is joined by one of SHP Financial's Certified Financial Planners™, Alina Osokhovska. As one of SHP's top planning advisors, Alina brings a wealth of knowledge and expertise to the complexities of this new legislation. They'll unpack how the bill alters standard deductions, reinstates the importance of itemizing, and introduces income-sensitive thresholds that could significantly affect your tax strategy.
In this conversation, you'll walk away with a clearer understanding of what's changing now and what's coming in the years ahead. Whether it's properly timing your Roth conversions, navigating the new SALT caps, or optimizing charitable contributions, this episode will help inform your decisions to maximize tax efficiency in retirement.
In this podcast interview, you'll learn:
- Why itemized deductions are back on the table and how to know if they benefit you.
- How changes to the SALT deduction cap can impact high-income households.
- What the new rules mean for Social Security taxation.
- Why retirees over 65 may benefit from an additional tax deduction and how to qualify.
- How charitable giving rules are shifting, both for itemized and standard filers.
- Financial planning opportunities that exist today before parts of the bill phase out in 2029.
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