Retirement Road Map

Hosted by Derek Gregoire, Keith Ellis, and Matthew Peck

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Episodes

129

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Oct 2026

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About the show

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!

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60 recent

November 6, 2026Episode 11522 min

115: Medicare Mistakes That Could Cost You Thousands in Retirement with Mark Kenney

You could have a well-funded retirement portfolio, a solid investment strategy, and plenty of money saved, yet still be paying thousands more than necessary for healthcare. The problem? Medicare isn't as straightforward as many retirees think. What you pay for coverage can depend on decisions you made years earlier, including when you retire, how much income you withdraw, and which accounts you take that money from. And some of the biggest surprises don't show up until it's too late to easily correct them. In this episode, I'm joined by SHP Financial's Mark Kenney to discuss some of the Medicare mistakes that can quietly eat away at your retirement savings. We'll explore why your Medicare premiums could increase even after your income drops, what Medicare doesn't cover that many retirees assume it does, and how the loss of a spouse can create an unexpected financial burden for the surviving partner. For specific information and updates around Medicare please visit: Medicare & You 2027 Medicare Costs In this podcast interview, you'll learn: Why Investment Planning Alone Isn't Enough Understanding Medicare Parts A And B Medicare Advantage Vs. Medigap Coverage Do You Need Medicare At 65? How RMDs Can Increase Medicare Premiums What Medicare Doesn't Cover For Long-Term Care Planning For Potential Long-Term Care Costs How Income Affects Your Medicare Premiums When You Can Appeal Higher Medicare Premiums The Hidden Financial Risks Of Losing A Spouse How Roth IRAs Can Reduce Medicare Costs The Tax Trap Of Inherited IRAs Why Retirement Planning Must Connect Everything 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

October 21, 2026Episode 11437 min

114: The Real Reason Your Investing Strategy Should Change Before You Retire with Mike Guthrie, CIMA®

The investment strategy that helped you build your retirement savings may not be the same strategy you need once you retire. When you're working and consistently contributing to your portfolio, growth is typically the primary goal. But once those contributions stop and withdrawals begin, market volatility can have a very different impact on your financial future. In this episode, SHP Financial co-founder Matthew Peck is joined by Mike Guthrie, to discuss the shift from accumulating wealth to distributing it in retirement. They explain why investors should start preparing for this transition several years before leaving the workforce, how sequence-of-returns risk can affect a retirement portfolio, and why an investment strategy that once made sense may need to evolve as retirement approaches. Matt and Mike also break down the roles of safety, income, and growth within a retirement portfolio and how each can help give retirees more options when markets fluctuate. Ultimately, the right mix will look different for everyone, which is why your investments should be built around your spending needs, income, risk tolerance, longevity, and broader retirement plan. In this podcast interview, you'll learn: Why investing for retirement is different from investing during retirement. When you should start repositioning your portfolio before retirement. How sequence-of-returns risk can impact your retirement savings. Why your current 401(k) may carry more risk than you realize. How safety, income, and growth can serve different roles in retirement. Why your investment strategy should be built around your broader financial plan. 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

October 9, 202642 min

Matt's Market on the Move- October 2026

Join SHP Financial Co-Founder Matt Peck, CFP®, CIMA®, and CFA® Zach Perkins as they discuss current market trends and their potential impact on your financial future.

October 7, 2026Episode 11345 min

113: The Growth Opportunities Private Markets Have That Traditional Investors Are Missing Out On with Raphael Hanna

When you think about investing for retirement, stocks, bonds, mutual funds, and ETFs probably come to mind first. But those public markets are only one part of the investment landscape. Private equity, private credit, real estate, infrastructure, and venture capital offer another universe of investment opportunities that many investors may know very little about. In this episode, SHP Financial co-founder Matthew Peck is joined by Raphael Hanna to break down the differences between public and private markets and explain why private investments have become increasingly accessible to individual investors. They discuss the different types of private investments, how they can potentially add another layer of diversification to a portfolio, and some of the important tradeoffs investors need to understand. Ultimately, having more investment options doesn't mean every option belongs in your portfolio. Matthew and Raphael explain why factors like liquidity, fees, risk tolerance, income needs, and time horizon should all be considered before investing in private markets and why every investment decision should start with your broader financial plan. In this podcast interview, you'll learn: The key differences between investing in public and private markets. How private equity differs from venture capital, private credit, and private real estate. Why more and more companies are staying private for longer durations. How private investments can provide another source of portfolio diversification. What investors should understand about fees, liquidity, and holding periods. Why your time horizon and risk tolerance matter when considering private 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

September 23, 2026Episode 11225 min

112: The Tough Retirement Conversations You Need to Have Before You Retire with Aidan Arone, CFP®

When you think about preparing for retirement, it's easy to focus on whether you've saved enough, when to claim Social Security, or how your investments will generate income. But some of the most important retirement decisions have very little to do with the numbers. What will you do with your time? How will your relationships change? And what happens if retirement arrives sooner than you expected? In this episode, SHP Financial co-founder Derek Gregoire is joined by Aidan Arone, CFP®, to discuss the emotional and logistical side of retirement planning that families often overlook. They explore why it's important to think about what you're retiring to, not just what you're retiring from, and why conversations about purpose, family, healthcare, spending, and your future lifestyle should happen well before your last day of work. Ultimately, a successful retirement isn't just about having enough money. Derek and Aidan share why couples and families should have the difficult conversations now, how planning for your life beyond work can make the transition easier, and why having a clear sense of purpose and community can be just as important as having a strong financial plan. In this podcast interview, you'll learn: Why retirement planning needs to go beyond the numbers. How losing your career can affect your identity and sense of purpose. Why maintaining social connections is so important after leaving work. Which retirement conversations couples should have before their last day of work. Why families should discuss healthcare, caregiving, and legacy plans in advance. How an unexpected event can force you into retirement before you're ready. 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

September 9, 2026Episode 11140 min

111: How Spousal Planning Creates Greater Confidence in Retirement with Nick Nelson

As couples approach retirement, their biggest question is typically whether they've saved enough to cover their expenses and enjoy the retirement they've worked so hard for. But what happens when one spouse passes away? The decisions you make today will undoubtedly affect the surviving spouse's income, taxes, investments, and overall financial security. In this episode, SHP Financial co-founder Matthew Peck is once again joined by Nick Nelson, VP of Advisory Solutions, to discuss why spousal planning is such an important (and often overlooked) part of retirement planning. They explain why both spouses should be involved in the financial planning process and how preparing in advance can provide greater confidence and continuity when the unexpected happens. Ultimately, spousal planning is about preparing for the difficult questions before you're forced to answer them under duress. Matt and Nick share how planning ahead can provide greater confidence that both spouses understand the plan, know what to do when the unexpected happens, and have the right people in place to help guide them through it. In this podcast interview, you'll learn: Why both spouses should understand the basics of their financial plan. How Social Security and pension decisions can affect a surviving spouse. Why expenses may not decrease significantly after one spouse passes away. How losing a spouse can dramatically change your retirement tax strategy. Why inherited IRA decisions require careful planning for surviving spouses. How beneficiaries, trusts, and proper account titling can help avoid costly mistakes. 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

August 26, 2026Episode 11033 min

110: The Benefits Of Your Tax & Financial Planning Teams Working Together with Lauren Bakken, CPA

Retirement isn't only about leaving your career behind. It's also about knowing what you're retiring to and making sure the financial decisions you make along the way support the life you want to create. And when taxes, investments, estate planning, and retirement income begin overlapping, trying to navigate everything on your own can become complicated quickly. In this episode, SHP Financial Lead Advisor Laura Russo sits down with recently retired CPA, Lauren Bakken, to discuss the lessons Lauren learned throughout her career serving individuals and small business owners. Lauren shares her own transition into retirement, why she believes your CPA, financial advisor, and attorney should be working together. In this podcast interview, you'll learn: How meaningful work and purpose can make retirement more fulfilling. The importance of understanding the tax consequences before taking retirement distributions. How your CPA, financial advisor, and attorney can work together. Why minimizing taxes isn't always the best financial decision. How small business owners can better prepare themselves for retirement. Why both spouses should understand the family's financial picture. 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

August 12, 2026Episode 10924 min

109: Retirement Income Strategies That Create Confidence and Peace Of Mind with Chris Willis, CFP®, CTS™

One of the most common questions that we hear from our clients isn't whether they've saved enough; it's whether their savings can actually provide the income they need to live the retirement they've envisioned. Building wealth during your working years is one challenge, but turning those assets into a reliable paycheck is where a comprehensive retirement plan becomes essential. In this episode, Keith Ellis Jr. is joined by Certified Financial Planner (CFP®) and Certified Tax Specialist (CTS™), Chris Willis, to discuss how retirement income planning goes far beyond simply withdrawing money from an investment portfolio. They explain how understanding your expenses is the foundation of every retirement plan, how different income strategies can fit different personalities and goals, and why no single approach works for every retiree. They also break down the strengths and tradeoffs of guaranteed income, dividend-focused investing, and SHP's bucket strategy for generating retirement income. You'll also learn how income planning fits into SHP's comprehensive retirement strategy that includes investments, taxes, healthcare, and estate planning. In this podcast interview, you'll learn: Why retirement income planning begins with understanding your lifestyle expenses. How guaranteed income, dividend investing, and bucket strategies each serve different goals. Why there's no one-size-fits-all approach to generating retirement income. How balancing safety, income, and growth creates a more resilient retirement plan. Why tax planning should influence your retirement income strategy. How a personalized retirement plan can help you retire with greater confidence. 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

July 29, 2026Episode 10829 min

108: The Biggest Regrets For Retirees (And How to Avoid Them) with Kyle Britton

Retirement is often viewed as a financial milestone, but many retirees discover that their biggest challenges have little to do with money. Many wish they had retired sooner, spent more confidently, prepared for the emotional transition away from work, or started important planning conversations with their families earlier. The good news is that these lessons don't have to be learned the hard way. In this episode, Keith Ellis Jr. is joined by Kyle Britton to share insights gathered directly from retired clients who reflected on what they would do differently if they could start retirement over again. Together, they discuss the most common regrets they've heard from retirees, including delaying retirement, underspending despite having enough savings, losing a sense of purpose after leaving work, and overlooking important tax, estate, and legacy-planning opportunities. They also discuss why retirement planning extends far beyond investments, how a comprehensive retirement plan helps pre-retirees make more confident decisions, the value of gifting assets during your lifetime, and why having meaningful conversations with family can help preserve both wealth and relationships for future generations. In this podcast interview, you'll learn: Why many retirees wish they had stopped working sooner. How a comprehensive retirement plan creates confidence to enjoy your money. Why purpose and routine are essential after leaving your career. How proactive tax planning can preserve more wealth for your family. Why gifting during your lifetime may benefit both you and your heirs. How healthcare and legacy planning shape long-term retirement success. Why open family conversations can prevent future estate conflicts. 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

July 10, 202637 min

Matt's Markets on the Move Q2: July 2026

Join SHP Financial Co-Founder Matt Peck, CFP ® , CIMA ® , and Lead Advisor, Laura Russo as they discuss current market trends and their potential impact on your financial future.