Scott Searles

Retirement Toolbox

Business EN ↓ 151 episodes

Financial and retirement planning guidance from Scott Searles of Skybox Asset Management, serving the greater Cleveland area and Bradenton, Florida. If you want a clear view of your financial situation then this is the podcast for you.

Author

Scott Searles

Category

Business

Latest episode

Nov 6, 2025

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Episodes

Crash Course: The Psychology of Investing in the Wake of Historic Market Crashes 18.05.2023

Have you ever wondered why you handle money the way you do? It turns out your financial behaviors can be traced back to your formative memories. In this episode, we explore how historic market crashes have left a lasting impact on our relationship with money. We’ll also contrast them with the way more recent crises have shaped our financial views and decisions in the short term.   Show Notes & Inf...

A Comprehensive Dismantling Of 2023’s Top Social Security Myths 04.05.2023

Have you ever wondered if the Social Security system will run out of money before you retire? Or if claiming benefits as soon as you're eligible is the best decision for your financial future? In this episode, we'll be debunking common myths about Social Security and answering the questions you've been curious about.   Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax-Fre...

Fore Your Retirement: What Golf Teaches Us About Financial Planning 20.04.2023

Are you a golfer? Even if you're not, the game of golf can teach us valuable lessons about retirement planning. For example, hitting a hole-in-one might be thrilling, but it won't necessarily guarantee your overall success. And just like you need different clubs in your golf bag to play a round, you need a well-balanced approach to your investments in retirement. But perhaps the most important les...

Retirement Expenses For Which You Forgot To Plan 06.04.2023

Are you preparing for retirement but feeling confident that you have covered all the expenses? Well, think again… It turns out that many retirees overlook some crucial expenses that can leave them financially vulnerable. In this episode, we explore the retirement expenses that most people tend to forget, including skyrocketing medical bills, unexpected travel costs, taxes, and much more. We'll dis...

Top Ten Tax Questions For Retirees In 2023 16.03.2023

Retirement can come with a lot of tax questions and concerns. From understanding the tax implications of withdrawing from your retirement accounts to minimizing taxes on investment income, it can be overwhelming. On today’s episode, we’ll break down the top ten tax questions retirees are asking in 2023. Before you file your 2022 taxes and plan ahead for the rest of the year, make sure to listen to...

Four Ways The SECURE Act 2.0 Might Impact You 02.03.2023

After being discussed in Congress for nearly a year and a half, the SECURE Act 2.0 passed in January. Listen to today’s episode to see what you need to know and learn four ways the new changes might impact you. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.infusionsoft.net/

Rookie Mistakes Even Experienced Investors Make 16.02.2023

Even if you’ve been saving your money and investing for a long time it’s easy to make rookie mistakes. On this episode, we’ll cover some of the top rookie mistakes we see people make, illustrate how to avoid them or how to fix them if you’re already made some mistakes in your financial life. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm...

2023 Edition: 10 Point Checklist For Retirement Preparedness 02.02.2023

Another year is upon us and it’s a great time to ask yourself 10 questions to assess how ready you are for retirement to kick off 2023. If you’re retiring this year, it’s essential to have some concrete answers to these questions. If you’re still a few years from the milestone, tune in so you can start thinking about these critical conversations. Show Notes & Info: Schedule A Call With Scott:  htt...

The Top 5 401(k) Mistakes You Need To Avoid 19.01.2023

Saving in your 401(k) can be an easy and painless way to build your retirement savings. But because it’s so easy and painless, it can also be easy to ignore for long periods of time, which often leads to mistakes. We’ll cover at least the top 5 mistakes people make in their 401(k)s. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.in...

The Financial Therapist: When It’s OK If A Visit To Your Advisor Feels Like Counseling 05.01.2023

Sometimes it might seem like talking to your financial advisor feels like talking to a therapist, and that’s ok. Let’s discuss some scenarios where it’s almost inevitable that a talk with your advisor seems like a counseling session. https://www.youtube.com/watch?v=sTFVMMCwsss Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.infusion...

Is There Greener Grass On The Other Side? 15.12.2022

Sometimes you need to find a new financial advisor. Other times, you might think you need a new advisor, but really, you’re just guilty of thinking that the grass is greener on the other side. Let’s discuss some common scenarios and whether they’re legitimate reasons for leaving your advisor. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gd...

Making Smart Decisions During Major Life Events 01.12.2022

Let’s explore some of the things you should be thinking about to make smart financial decisions when you encounter some of the most significant events in your life. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.infusionsoft.net/

Most Common Retirement Planning Questions About Taxes 17.11.2022

As we approach the end of the year, saving money on taxes becomes a bigger focus for many people. But let’s broaden the scope out for this particular episode and focus on some of the most common retirement planning questions about taxes. We’ll talk about mistakes to avoid and how a proper plan can make a significant difference in someone’s tax savings. Show Notes & Info: Schedule A Call With Scott...

The Money Gridiron: What Football Teaches Us About Retirement Planning 03.11.2022

At this time of year, you can find football on TV almost every night of the week. So, let’s take some concepts from the game of football and apply them to our retirement planning. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.infusionsoft.net/

Getting It Right: Irreversible Financial Decisions 20.10.2022

There are plenty of decisions that you’ll make in the retirement planning process that can’t be undone, so you want to make sure that you make the right call. On this episode, we’ll explain why these decisions are so important and can’t be undone. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.infusionsoft.net/

How Money Ads Catch Your Attention 06.10.2022

We’re bombarded with ads each day in all forms of media. But have you ever taken a closer look at these messages? If we unpack some of these headlines and ads a little bit more, we’re able to clearly understand what emotions they’re trying to elicit. More importantly, we can figure out what companies are trying to sell us. For this episode, we just perused the internet for a couple of hours and ke...

Should You Follow These Popular Retirement Rules of Thumb? 15.09.2022

You’ve most likely heard plenty of “rules” you’re supposed to follow to retire successfully. Some of these rules are stated so confidently, you’d be crazy not to immediately accept them as fact. But we don’t mind the threat of being called crazy, so let’s dive into some of the most popular retirement “rules of thumb” to see if they truly lead us down the path of good financial guidance or run a ch...

What Hurricanes Teach Us About Retirement Planning 01.09.2022

Weather enthusiasts and retirement planning worlds collide… Each Fall we spend a lot of time watching and listening to the news and the Weather Channel getting reports of developing hurricanes and are treated to lots of updated graphics to bring us a refresher on how hurricanes work. So, let’s take the opportunity to see what we can learn about retirement planning from a discussion about hurricane...

Can You Get An A+ On Our Retirement Planning Quiz? 18.08.2022

Don’t dread this as much as you hated hearing these words as a kid, but it’s time for a pop quiz! We’re putting retirement planning preparedness under the microscope with 5 critical questions to which you need to know the answers. So sharpen those pencils and let’s see how ready you are for retirement. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https...

Tough Topic: Retirement & Divorce 04.08.2022

Going through a divorce at any age is difficult, but doing it near or in retirement adds all sorts of additional complications. On this episode, we’ll talk about some of the financial mistakes we see people make in the midst of a divorce. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.infusionsoft.net/

Why Retirement Planning Ain’t What It Used To Be 21.07.2022

In some ways, retirement planning was easier for past generations. Let’s explore how a good financial advisor helps people overcome the additional challenges of today. Our parents and grandparents may not have had to face these things, so just relying on the experiences of family members might not be enough to help us achieve our own financial success. Link: https://www.youtube.com/watch?v=YvT_gqs...

Investor Beware: Spotting Red Flags When Picking An Advisor 07.07.2022

Do you know what red flags, but also some good signs, to be on the lookout for when you’re searching for an advisor to work with as you prepare for retirement? On this episode, we’ll give you some red flags to be aware of, teach you how to spot them and illustrate the difference between an advisor who does the bare minimum versus one who goes above and beyond to work in your best interests. Show N...

Secret To Retirement Success: Get Out Of Your Own Way 16.06.2022

There are plenty of external factors that often negatively influence our chances of having a successful retirement. But often, failure comes from within. On this episode, we’ll talk about some of the common ways people get in their own way when it comes to financial planning. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.infusions...

What To Do As You Count Down The Days To Retirement 02.06.2022

We've assembled a list of 7 priorities to keep in mind as you count down the days to retirement. We'll discuss things like getting and staying healthy, taking advantage of opportunities to save more, post-retirement careers, and much more. Show Notes & Info: Schedule A Call With Scott:  http://talktoscott.com/ Tax Free Toolkit:  https://5p7b1gdm.pages.infusionsoft.net/

Reasons You SHOULD Get Life Insurance 19.05.2022

Sure, life insurance is one of the more boring topics to cover on a podcast. And a lot of what you hear is going to warn you why you should NOT get various types of life insurance. But our goal on this episode is to focus on the positive and analyze the reasons why you should get life insurance, or at least consider it. Many people think that once the kids are out of the house, you don’t need insu...

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