Scott Searles
Retirement Toolbox
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
Podcast website
Latest episode
Nov 6, 2025
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Episodes
Is Your Portfolio Infected With A Virus? 24.03.2020 23:59
We'll take a look at the Coronavirus' impact on the financial markets, the economy and our personal retirement plans. Scott will help us try to put it all in perspective and figure out where we go from here. Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www.skyboxasset.com Call: 888-742-0111
Your Desire To Retire 19.03.2020 23:14
Different people have different levels of desire when it comes to finding their retirement date. Let’s explore these different levels of desire, as indicated by the statements people might make, and discuss how we’d help someone at these different levels. Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www.skyboxasset.com Call: 888-742-0111
All You Need To Know About Roth Conversions 05.03.2020 21:27
The idea of a Roth conversion is intriguing to a lot of people, and for some people it can be a great strategy to enact. Let’s explore the concept on this episode. Plus, we'll answer some Social Security questions from one of our listeners. Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www.skyboxasset.com Call: 888-742-0111
Where To Find Bias In Financial Media 20.02.2020 29:13
It’s always good to keep yourself up to date with what’s going on in the financial world. But it’s also important to understand that the information you get from the media isn’t completely unbiased. Let’s talk about some of the problems with the financial media. Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www.skyboxasset.com Call: 888-742...
Lies You Learn In Broker School 06.02.2020 25:53
A lot of financial professionals say things that just aren’t true. And it’s not that they’re intentionally trying to mislead, it’s just that they’ve been trained to use certain talking points, which they might even believe to be true themselves. Let’s talk about the statements you should be cautious of if you hear them from a financial advisor. Show Notes & Info: Tax Free Toolkit: https://5p7b1gd...
Managing Debt & Retirement Planning 16.01.2020 23:08
Do you believe you need to be completely debt free to retire successfully? Or are you okay carrying some balances beyond your working years? There are many opinions about the best way to handle debt and retirement planning, so we’ll tackle them all on today’s show. Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www.skyboxasset.com Call: 888-...
Must-Have Traits Of A Financial Advisor 02.01.2020 23:44
Trustworthy. Likeable. Problem-solving. Good listener. We should be describing your financial advisor or a potential advisor if you’re in the process of finding one. On today’s show, we’ll talk about why it’s so important for your advisor to embrace these kinds of characteristics. That’s the easy part. But we’ll also tackle the harder part and discuss some tangible ways how you can determine if an...
Avoiding Critical Estate Planning Mistakes 19.12.2019 28:51
There are some people who don’t care at all about leaving a financial legacy, but for those who do, it’s important to eliminate some of these common estate planning mistakes… Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www.skyboxasset.com Call: 888-742-0111
Top 5 Social Security Misunderstandings 05.12.2019 30:18
Myths, rumors, and misunderstandings are pervasive in the world of Social Security. On this show, we’ll look to clear up the top 5 misunderstandings about Social Security. Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www.skyboxasset.com Call: 888-742-0111
How To Live A Retirement Without Regret 21.11.2019 28:14
Simple mistakes can sometimes lead to larger regrets in retirement. On today’s show, we’ll explore some of the things you can do to avoid living with regret in retirement. Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www.skyboxasset.com Call: 888-742-0111
It’s Good To Have Awkward Conversations In Financial Planning 07.11.2019 23:48
Sometimes being a good financial advisor means having uncomfortable conversations. We’ll take a look at how advisors should help clients navigate various tricky situations. If you’re going to be working with a financial advisor, make sure they’re pushing you to address these kinds of topics. Show Notes & Info: Tax Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Skybox Website: https://www...
What The Next Market Crash Will Look Like 17.10.2019 27:38
Some people think we’re on the cusp of the next stock market crash. Others predict that we’re just due for a minor correction. And another camp thinks we’ll continue an upward trend. We don’t know who is right or when any of those options will occur. But let’s talk about what the next market crash might look like, even if we don’t know when it will come. Show Notes & Info: Tax Free Toolkit: https...
Even Responsible Savers Make These Mistakes 03.10.2019 26:15
Even for people who have been very responsible with their money over the years, entering retirement can still be a challenge because it’s such a different stage of life. Let’s talk about some of the missteps that even responsible savers can make. Tax Free Toolkit https://www.skyboxasset.com/blog
Is Playing The Blame Game Holding You Back Financially? 19.09.2019 23:43
Have you ever had financial trouble? And we’re not just talking about the direst of situations like going bankrupt. Do you think a divorce is to blame for messing up your finances? Do you tend to think the system is rigged against the little guy? Did a former broker “do you wrong”? On today’s podcast, we’ll look at some of the common things that people might blame for their financial planning trou...
3rd & 4th Quarter Planning To-Do List 05.09.2019 24:13
As we get into the 2nd half of 2019, there are several planning items you might want to run a quick checkup on to make sure you’re still on the right financial track. Especially if you’re a retiree, or pre-retiree. Are you focusing on the right things? Listen to today’s podcast to find out. We'll also answer a question from Howard about dividend-paying stocks. https://www.skyboxasset.com/blog
You Need To Avoid These Portfolio Disasters 15.08.2019 27:13
Between wildfires, hurricanes, tornados and floods, there’s always a natural disaster making news headlines. And while life and limb aren’t at stake when it comes to your portfolio, experiencing a financial disaster can still have a catastrophic effect on your life in retirement. Let’s discuss some portfolio disasters that we’ve seen and how to avoid them...
What Does Financial Security Mean To You? 01.08.2019 25:06
“Financial Security” might mean different things to different people, but for nearly everyone, making sure that they achieve their own definition of security is the most important part of their retirement plan. So, how do you define financial security? On today’s show, we’ll cover some of the popular responses we hear from clients during the planning process.
Learning Financial Lessons From Popular Proverbs 18.07.2019 22:13
There are plenty of proverbs and axioms that aren’t meant to be about money, but we can easily learn a financial lesson from them anyway. We’ll show you the hidden money meanings behind some of these popular sayings. We have a great question from Roberta putting her entire 401(k) into company stock. And where would Scott go if we kicked him out of North America? We'll find out the answers to that...
How "Fake News" Impacts Your Finances & That Time Scott Got In Big Trouble 03.07.2019 27:15
We all probably did something that got us in big trouble when we were kids. Just wait until you hear what kind of mischief Scott was up to when he was little. Plus, did you know you're probably being exposed to financial "fake news" on a daily basis? We'll look at some common headlines that qualify as "fake news" and teach you how to spot other problematic headlines. And Jim has a question on the...
Goat Yoga, Stretch IRAs & How To Get "Unstuck" From Difficult Financial Decisions 20.06.2019 27:26
Goat Yoga... That's actually a thing these days. And it somehow comes up on today's podcast when we answer a question from Arnold about a "Stretch IRA". You won't want to miss that conversation. We'll also switch gears and talk about how for some people, the biggest problem with their financial planning isn’t that they make the wrong decisions. It’s that they often fail to make decisions at all. B...
Planning For Summer Vacation & Retirement Are A Lot Alike 06.06.2019 25:41
If you’re heading out on a road trip this summer, there’s a long checklist of items that you want to be sure you haven’t forgotten. And in retirement planning, some of those exact same items need to be addressed. Let’s look at some of the items that should appear on both your road trip checklist and your retirement planning checklist. We'll also answer a question from Jeff about retiring early at...
Conventional Wisdom Isn't Always So Wise 16.05.2019 26:20
Let's discuss a few examples where following conventional wisdom might lead you astray. We'll also answer a question from Mary about the consequences of making a mistake while rolling over a 401k. And if Scott had to be an animal, what kind would he be? https://www.skyboxasset.com/blog
Facing The 4 Realities Of Retirement Planning 02.05.2019 24:10
The realities of retirement planning are different than they were even a decade ago. Let’s talk about some of the realities that affect how you need to plan. We'll also answer a question from Lou about assuming you'll be in a lower tax bracket in retirement. And was Scott once known to wear parachute pants? We'll find out on this episode. https://www.skyboxasset.com/blog
5 Dangerous Mindsets That Could Sink Your Retirement Future 18.04.2019 24:12
In many phases of life our attitudes and mindsets can have big impacts on where we go and what we do. Retirement planning is no different. Let’s look at the five dangerous mindsets that can quickly sink your retirement if you’re not careful to guard against these, sometimes, natural instincts. https://www.skyboxasset.com/blog
Getting To Know Scott Searles 04.04.2019 18:29
We'll get know Scott a little better on this first show. We'll find out why he got into the financial industry, what stirs his passion for helping people plan for retirement, and how he and the team at Skybox Asset Management approach their relationship with clients. https://www.skyboxasset.com/blog
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