Winning Retirement Radio

We touch on Tom Cruise’s latest Mission: Impossible, and his intent to never retire, then shift to Warren Buffett’s advice to invest in a low-cost S&P 500 index fund. While that might work for younger investors, Greg and Kristin warn retirees to be cautious. Market drops can seriously impact income in retirement! Their takeaway: don’t follow headlines blindly. Build a plan wi...

Greg and Kristin dive into a pressing issue affecting more families than ever before: the increasing need for long-term care in America. You’ll hear a personal caregiving experience, a journey that has become common among friends, neighbors, and loved ones. But here’s the catch: traditional long-term care insurance is disappearing, and the few policies still available are often too exp...

Greg and Kristen discuss tipping trends and why some people tip less with digital prompts. They also break down Required Minimum Distributions (RMDs): when to take them, how they’re taxed, and strategies to avoid costly mistakes.   Unsure if you’re on track for retirement? Fill out this short form for a FREE consultation .   See omnystudio.com/listener for privacy information...

After discussing the differences between being frugal and being cheap, Greg and Kristin highlight why many retirees find it challenging to begin spending their money. In addition to having an investment and income plan, creating a spending plan is essential. Retirement represents a significant life change that many people fail to recognize, and transitioning from saving to spending from your portf...

We recap Uber's weird lost and found items and share a tale of a misfortune-stricken philanthropist. Then explore the rewards of generosity. Kristin will also provide us with an update on the latest developments at Dare For More , one of her beloved charities.   Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit to help you get organized:  See...

After discovering that Greg and Kristin work and exercise together, we shift our focus to family matters. We examine the various reasons why retirees sometimes provide financial assistance to their adult children. Listen for stories that shed light on both sides of this important issue.    Wondering if you’re on track for retirement? Fill out this short form for a FREE consultation...

Google searches for " how to reduce stress " have reached a record high. With the markets responding to tariff news, many individuals with retirement funds on Wall Street are feeling uneasy. Greg and Kristin discuss the importance of having a plan that considers challenging times so that your income isn’t dependent on the uncertainties of the market!   🤔 Wondering if you’re on tr...

This week, we're discussing everyday things that make us feel unsettled or uncomfortable. One topic that stands out is Math Anxiety. This issue can create significant challenges during retirement. If memories of Geometry and Algebra are causing you to avoid your financial and retirement planning, remember that you don’t have to tackle it all by yourself! Greg and Kristin talk about “do...

The world has changed dramatically in just the past 10 years! This is especially true for Greg and Kristin as the school season comes to a close. In this episode, we reflect on various aspects of life, from movies and music to customer service and everything in between. We discuss how we approach different parts of our lives much differently than we did just a few years ago. Planning for retiremen...

Did you know pure gold (23-24 karat) is safe to consume in small quantities? You might have seen advertisements about investing in precious metals. That's why we're exploring gold as an asset class for individuals who are in or approaching retirement as part of a diversified portfolio. This is especially relevant now, with market volatility! Also, listen to learn how much of a creature of habit Gr...

Are you feeling overwhelmed when it comes to making money decisions? You’re not alone. A recent survey shows that 53% of Americans feel stuck, overwhelmed, or unsure about their finances. Greg and Kristin discuss the importance of avoiding "paralysis by analysis" and how collaborating with a fiduciary financial advisor can alleviate some of those feelings. Additionally, they emphasize the ne...

Are you feeling overwhelmed when it comes to making money decisions? You’re not alone. A recent survey shows that 53% of Americans feel stuck, overwhelmed, or unsure about their finances. Greg and Kristin discuss the importance of avoiding "paralysis by analysis" and how collaborating with a fiduciary financial advisor can alleviate some of those feelings. Additionally, they emphasize the ne...

Americans do a lot of giving, and often, that giving mindset doesn’t change when you stop working. In retirement, there are efficient ways to give that some take advantage of. In fact, Kristin shares how one woman made her qualified charitable distribution (QCD) goals from her retirement accounts come to life  despite some paperwork obstacles.  Need a little help getting organized?...

Retirement can be a challenging transition. This week, we discuss how to tailor your retirement plans to your unique situation, considering your budget, portfolio, income, and more. We'll also explore the "normal" expectations of retirement and share stories of people enjoying their unique retirement lifestyles.    Wondering if you’re on track for retirement? Fill out this short fo...

In this episode, Greg and Kristin dive into the world of annuities, breaking down the key differences, including their advantages and disadvantages, to help you navigate retirement income concerns. 📸  Plus, the interesting story behind the first-ever selfie and when it was taken! Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Retirement Kit to help get...

This week's episode covers encouraging economic news regarding Americans and debt, the significance of maintaining an emergency fund as you approach or enter retirement, and advice for those worried about market volatility and risk exposure.   Unsure if you’re on track for retirement? Fill out this short form for a FREE consultation . See omnystudio.com/listener for privacy information.

From investing to spending, budgeting, and even charitable giving, maintaining open communication about finances is crucial for couples. 👩‍❤️‍👨 Greg and Kristin share how they avoid money miscommunications, and how they encourage the families they help to do the same. Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit to help you get organized....

We discuss tax season and what you need to know if you're approaching age 73 and preparing to take Required Minimum Distributions (RMDs). We'll cover important topics such as how much you need to withdraw, penalties and fees to avoid, and the benefits of Qualified Charitable Distributions (QCDs). By the end of this episode, you should have a clearer understanding of your future tax obligations in...

Does your advisor address how you’ll use your money in retirement? Have they helped you create a plan to be tax-efficient with your portfolio when you stop working? Hear insight into those questions, plus Greg’s “why” on this week’s episode.    Wondering if you’re on track for retirement? Fill out this short form for a free consultation . _____________...

Did you know you could become a marketing target if the probate process enters your world? Greg and Kristin aren’t attorneys, but legacy and estate planning conversations are consistent with retirement planning. Listen as they share why being “sold” any product isn’t a good idea.  Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Re...

We all take different paths in life. For example, women are more likely than men to pause their careers to care for their families. As a result, they typically work fewer years and contribute less to retirement accounts, leading to lower savings in their investment portfolios. Greg and Kristin discuss these challenges and how to tackle them with effective retirement planning.  Need a little h...

A recent survey showed Americans would rather do homework than do their taxes, and some would rather take the SATs! Tax season is important, but Greg and Kristin explain why retirement tax strategies are essential for future portfolio planning. Wondering if you’re on track for retirement? Fill out this short form for a FREE consultation .   See omnystudio.com/listener for privacy inform...

This week Greg shares his approach to tackling holiday credit card debt along with tips on how to pay off debt in general... and stay motivated . Plus, an answer to a common retirement question: Should your mortgage be paid off before you stop working?  Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Retirement Kit to help get organized. ___________...