077: Estate Planning Essentials to Help Protect Your Assets and Legacy with Matthew Karr, ESQ
Release Date: 04/09/2025
091: Estate Planning Essentials: How Trusts & Gifting Protect Your Legacy with Attorney David Chaves
Retirement Road Map
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...
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090: Going Beyond the Portfolio: Transitioning Into Retirement with Confidence with Kyle Britton
Retirement Road Map
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...
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Matt's Markets on the Move Q3: October 2025
Retirement Road Map
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089: The Future of Fannie Mae and Freddie Mac and What Privatization Could Mean for Homebuyers with Nathan Hartseil
Retirement Road Map
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...
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088: The Importance of Retirement Planning for Women and Widows with Alina Osokhovska, CFP®
Retirement Road Map
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...
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087: How Death Doulas Help Families Navigate End-of-Life with Love & Compassion with Aimee Yawnick
Retirement Road Map
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...
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086: Career Insights for New Grads Aspiring to Become Financial Advisors with Raphael Hanna
Retirement Road Map
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...
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085: How Donor-Advised Funds Simplifies Charitable Giving And Maximizes Tax Benefits with Kyle Casserino
Retirement Road Map
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...
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084: Examining the Big Beautiful Tax Bill & What it Means for Your Retirement with Alina Osokhovska
Retirement Road Map
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,...
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Matt's Markets on the Move Q2: July 2025
Retirement Road Map
Co-Founder, Matt Peck, CFP®, CIMA®, and Investment Analyst, Zach Perkins CFA®, team up to deliver the market update for Q2. Matt and Zach discuss what's currently going on in the markets — where we've been, where we're headed, and how tariffs and the “Big Beautiful Bill” may impact the economy. They'll also address key questions submitted by our clients. During times of uncertainty, our priority is to keep you informed and help ensure you feel supported every step of the way. If you have any questions or concerns, please don’t hesitate to reach out to your...
info_outlineEstate 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 SHPfinancial.com/podcast
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