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The Retirement Playbook
Many people spend decades saving for retirement only to find themselves too paralyzed by the fear of running out of money to actually enjoy it. The Retirement Playbook was created to bridge this gap, shifting the focus from mere accumulation to confident, purposeful spending and legacy building. By combining smart tax strategies with a bold new mindset, we help Greater Boston families view retirement not as a finish line, but as a starting gun for their best life. Join us as we redefine retirement—not as a defensive retreat, but as an offensive play to fund your experiences and impact your fam...
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Épisodes
Stop Trying to Beat the Market. Start Owning It 31.10.2026 56:00
Are you nearing retirement and wondering whether to invest in individual stocks or index funds? This episode of The Retirement Playbook delves into the world of investing, where the hosts, Jon Coughlin and Kyle Hurley, share their expertise on how to make informed decisions about your retirement portfolio. With a focus on protecting your savings and outlasting your retirement, they discuss the imp...
Year-End Planning & HowTo Make The Most Of Your Retirement Savings 24.10.2026 42:48
As the year comes to a close, it's time to review and plan for the future. This episode of The Retirement Playbook is all about year-end planning, covering tax planning, investment planning, and goal planning for your finances. The hosts, Jon and Kyle, dive into the importance of reviewing your finances, investments, and tax strategies to ensure you're on track for a successful retirement. See omn...
Are You Getting Your Money's Worth From Your Financial Advisor? 17.10.2026 42:48
Are you paying your financial advisor for just a stockbroker service, or are you getting a true partner who helps you achieve your financial goals? In this episode of The Retirement Playbook, hosts Kyle Hurley and Jon Coughlin discuss the six key pillars that a great financial advisor should be hitting on with their clients. From organization to objectivity, these pillars are essential for making...
Are You Paying More in Taxes Than You Need To? 10.10.2026 42:47
Are you tired of feeling overwhelmed by taxes and unsure of how to reduce your tax bill? Do you wish you had a clear plan in place to ensure your loved ones can easily manage your finances if something were to happen to you? This episode of The Retirement Playbook is for you. Join Kyle Hurley and his special guest, Chris Nash, managing partner of Nash CPAs, as they dive into the world of tax savin...
The Financial Blind Spots You Don't Know You Have 03.10.2026 42:49
Imagine being able to enjoy your retirement without worrying about running out of money or leaving a financial mess for your loved ones. This episode of The Retirement Playbook explores the importance of holistic financial planning and how it can make a significant impact on your life. From reducing taxes to estate planning, the speaker delves into real-world examples of how they've helped clients...
How Much Cash Should You Have In Retirement 26.09.2026 42:46
The Retirement Playbook is back with a crucial discussion on cash in retirement. This week, hosts Kyle Hurley and Jon Coughlin dive into the often-misunderstood topic of how much cash to keep in retirement. They share real-life examples of clients who have struggled with this very issue, and offer practical advice on how to navigate the complexities of cash management in retirement. See omnystudio...
The Retirement Asset That No One Wants To Spend 19.09.2026 42:47
As we navigate the complexities of retirement planning, one crucial aspect often gets overlooked: real estate. In this episode of The Retirement Playbook, hosts Jon Coughlin and Kyle Hurley dive into the world of real estate and its impact on retirement. They explore the intricacies of managing real estate in retirement, discussing topics such as mortgage versus no mortgage, real estate's role in...
The Biggest Risk Retirees Aren't Thinking About 11.09.2026 42:47
Are you nearing retirement and feeling paralyzed by the fear of running out of money? You're not alone. Many people spend decades saving for retirement, only to find themselves uncertain about how to make their savings last. In this episode of The Retirement Playbook, hosts Kyle Hurley and Jon Coughlin discuss the importance of risk management in retirement planning. They share a story about a cou...
Should I Be Doing Roth Conversions? 05.09.2026 42:48
Are you considering a Roth conversion, but not sure if it's right for you? This episode of The Retirement Playbook is a must-listen for anyone looking to make informed decisions about their retirement savings. Join Jon Coughlin and Kyle Hurley as they dive into the world of Roth conversions, exploring the pros and cons, and sharing real-life examples of when it makes sense and when it doesn't. See...
Retirement Looks Simple And Then The Stock Market Fell 35% 29.08.2026 42:46
Imagine being in your mid to late 60s, ready to retire, but unsure if you've saved enough. This is the reality for many people, but with the right guidance, it's possible to achieve a secure financial future. In this episode of The Retirement Playbook, we meet a couple who came to us seeking clarity on their retirement plans. With a combined income of $300,000 and a goal to retire in two years, th...
They Had Plenty Of Money To Retire, They Just Didn't Know It 22.08.2026 42:49
In this episode of the Retirement Playbook, Kyle and Jon discuss a common scenario: a couple in their late 60s, both nurses with a combined income of over $200,000, who came to them unsure if they had enough savings to retire. Despite having a significant amount of money, they were paralyzed by fear and uncertainty. Kyle and Jon walk us through their process of helping this couple uncover their hi...
Redefining Retirement: It's Not Just About the Number 15.08.2026 42:39
In this episode, Kyle and Jon walk us through the process of helping this couple determine their retirement income number, which is not just about accumulating a certain amount of assets, but also about understanding their current take-home pay, expenses, and how retirement will change their financial situation. They also discuss the importance of painting a picture of what retirement will look li...
Redefining Retirement, One Plan at a Time 08.08.2026 42:50
Imagine having the confidence to enjoy your retirement without stressing about your finances. A recent case study on this episode of the Retirement Playbook highlights the importance of having a comprehensive plan in place. A couple in their seventies, with a significant amount of savings, realized they needed help navigating their retirement strategy. They were taking too much risk, not enough ta...
Understanding Annuities: Separating Fact from Fiction 01.08.2026 42:50
Are you considering an annuity for your retirement plan, but unsure if it's the right choice? This episode of The Retirement Playbook is a must-listen for anyone looking to navigate the complex world of annuities. Hosts Jon Coughlin and Kyle Hurley dive into the benefits and drawbacks of these often-misunderstood products, helping listeners separate fact from fiction and make informed decisions ab...
Unlocking the power of your employer stock plan 25.07.2026 42:48
This episode is all about taking control of your company stock and making the most of its potential. John and Kyle share real-life examples of how people have successfully navigated the complexities of company stock, and how having a plan in place can make all the difference. They also discuss the importance of diversifying your investments, and how to avoid the risk of having too much of your net...
Financial Motivation – The Hard Way Is the Right Way 18.07.2026 42:48
Imagine working decades to save for retirement, only to have your plans derailed by the fear of running out of money. This episode of The Retirement Playbook explores the crucial topic of risk management, and how it can make or break your retirement plans. Join Kyle Hurley and his partner Greg Munroe as they discuss the common pitfalls that many people face when it comes to managing risk in their...
The Financial Decisions That Matter Most Before Retirement 11.07.2026 42:47
As we approach the halfway point of the year, many of us are taking stock of our finances and wondering if we're on track for a secure retirement. But what if you're in your forties or fifties and feeling overwhelmed by the prospect of planning for the future? This episode of The Retirement Playbook explores the importance of taking a step back and assessing your goals, both financial and personal...
Building Your Retirement Income Stream 04.07.2026 42:46
Are you ready to enjoy your retirement without worrying about running out of money? This episode of The Retirement Playbook explores the importance of creating a reliable income stream in retirement, and how to make the most of your hard-earned savings. Join hosts John and Kyle as they discuss the challenges of transitioning from a lifetime of saving to a lifetime of spending, and how to navigate...
Leveraging Your Business to Pay Less in Taxes and Build More Wealth 27.06.2026 42:47
Are you a business owner looking to grow your wealth and reduce your tax bill? This episode of The Retirement Playbook is for you. Join Jon and Kyle as they discuss the importance of business structure, retirement planning, and succession planning in achieving your financial goals. See omnystudio.com/listener for privacy information.
The White Glove Difference: How To Implement Your Retirement Plan 20.06.2026 42:46
Imagine having a team of experts working behind the scenes to ensure your financial plan is executed seamlessly. This episode of The Retirement Playbook takes you on a journey to meet the unsung heroes of financial planning, the operations team. Daria Grady, Director of Operations at Munroe Morrow Wealth Management, shares her insights on what sets successful clients apart and how her team makes t...
Is It Worth It To Work With A Financial Advisor? 13.06.2026 42:46
In this episode of The Retirement Playbook, hosts Jon Coughlin and Kyle Hurley dive into the age-old question: is it worth it to work with a financial advisor? With the ever-changing landscape of the financial industry, many people are left wondering if paying for professional guidance is worth the cost. But what if we told you that working with a financial advisor could add up to two to five perc...
How to Enjoy Your Wealth While Helping the People You Love 06.06.2026 42:47
This week, hosts Jon Coughlin and Kyle Hurley are joined by Matt Morrow, founder and president of Munroe Morrow Wealth Management, to discuss how to make the most of your retirement and create a lasting legacy for your loved ones. With the markets having performed exceptionally well over the past decade, many people are finding themselves with more wealth than they ever expected. But with this new...
Is Social Security Going Away? 30.05.2026 42:47
Are you worried about the future of Social Security? You're not alone. Many people are concerned about the long-term viability of this vital benefit, but the truth is, it's not going away. In this episode of The Retirement Playbook, hosts Jon Coughlin and Kyle Hurley dive into the world of Social Security, clearing up common misconceptions and providing expert advice on how to make the most of thi...
Estate Planning: Protecting Your Legacy and Business 23.05.2026 42:48
Imagine leaving behind a legacy that's not only financially secure but also free from conflict and stress for your loved ones. This episode of the Retirement Playbook delves into the world of estate planning, where Mark Scandier, a state attorney, shares his expertise on how to protect your wealth, business, and family. From avoiding probate to creating a seamless transfer of wealth, Mark breaks d...
$5 Million Ain't What It Used To Be 16.05.2026 42:47
In this episode of The Retirement Playbook, hosts Jon Coughlin and Kyle Hurley dive into the realities of retirement planning. They discuss how five million dollars may not be enough to sustain the lifestyle you envision, especially with rising healthcare costs and taxes. The hosts share a real-life example of a couple who thought they were set, but found themselves struggling to make ends meet. T...
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