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

Combatting Popular Excuses For Poor Financial Decision-Making 06.06.2024

Very often, we see people who know that the financial decisions that they’re making aren’t the best decisions, but they try to create excuses or explanations for why they’re doing what they’re doing. Let’s talk about why these excuses usually don’t hold water.   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

Your Financial Wellness Check-Up 16.05.2024

Just like an annual checkup is important for maintaining good health, performing regular financial checkups is an essential part of planning for a healthy and successful retirement. By regularly assessing your budget, goals, and progress, you can make informed decisions to keep your finances on track. Although financial wellness is going to look different for everyone, we’ll share some areas you s...

Steering Clear of Retirement Stress 02.05.2024

Psychologists have determined that retirement is one of the most stressful events that some people will experience in life. In this episode, we’ll look at the ways to proactively deal with the stress surrounding the retirement process.   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

Finance Fortress: Practical Strategies for Retirees Against Scams & Fraud 18.04.2024

As much as any other threat, recognizing and avoiding scams has become a necessary skill for today’s retirees to develop. Join us as we explore crucial steps you can take to safeguard your financial well-being against the growing tide of scams and identity theft. Learn from real-life stories and gain practical advice to keep your finances secure in this digital era, all from the perspective of a s...

How Is Technology Redefining Retirement Planning? 04.04.2024

Unpack the toolbox of technology that's promising to redefine retirement planning, but does it deliver? This episode takes a critical look at the wave of innovations, from personal finance management software to online calculators, and questions whether they truly simplify the planning process or introduce new complexities.   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax...

Retirement Planning Is Different For Women: Here’s Why 21.03.2024

With International Women’s Day in March, it’s the perfect time to reflect on the progress women have achieved in the financial realm over the past century. Despite this, the path to retirement is not without its unique challenges for women, and it’s important to recognize the financial hurdles that they continue to face. In this episode, we’ll share some eye-opening statistics and actionable advic...

Retirement Bracketology: Money Lessons While Filling Out Your March Madness Bracket 07.03.2024

March Madness is upon us, and as you fill out your bracket and watch the NCAA Tournament this year, there are a few retirement planning lessons that you can learn along the way…   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

Will These Apocalyptic Predictions Ever Come True? 15.02.2024

We’ve all heard the apocalyptic predictions about social security, the national debt and other major issues that are supposed to sink the economy. Do any of these predictions have merit in the years ahead? On this episode, we’ll try to separate sensationalism from reality.   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.n...

With Higher Interest Rates, Is “Lazy Money” Still A Concern In 2024? 01.02.2024

Is 'Lazy Money' still a concern in 2024's higher interest rate landscape? In this episode, we explore this question, examining how the recent rise in interest rates affects the money sitting in savings accounts, CDs, and conservative investments. We'll discuss the new dynamics of managing your funds in a world where traditional saving methods are seeing better returns. Are these options now a viab...

The Questions You Must Ask Your Financial Advisor 18.01.2024

Have you ever wondered what questions to ask your financial advisor, or why those questions are crucial? In today’s episode, we’re tackling exactly that. We're discussing the vital questions that bring transparency and depth to your financial advisory relationship. It's about getting clarity on how advisors work, what they specialize in, and how they align with your financial goals. These are the...

Strategic Planning for Retiree Healthcare 04.01.2024

In today's episode, we're focusing on a critical aspect of retirement planning: healthcare costs. How well prepared are you to handle medical expenses after you retire? We'll discuss everything from Medicare complexities to strategies for managing unexpected health-related expenses. Tune in as we break down the essentials of healthcare financial planning for retirees.   Show Notes & Info: Sche...

Easy Wins in Personal Finance 21.12.2023

It’s important to eventually get a comprehensive financial plan for yourself, but sometimes even just a few minor adjustments in your portfolio can make a big difference. Let’s discuss a few easy places to start.   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

How To Successfully Climb The Retirement Mountain 07.12.2023

Ready for an adventure? Think of retirement planning as climbing a mountain. It's not just about the climb up; it's about preparing wisely, tackling the ups and downs, and even planning your way back down. We're talking about setting milestones, dealing with market surprises, and making sure your hard-earned savings last through your entire retirement journey. Join us as we gear up with some smart...

Financial Resolutions 21.11.2023

As the year comes to a close, we thought it would be a good idea to revisit a previous two-part episode on financial resolutions. This series was recorded a couple of years ago, but the show still has some great tips that can help you start your year off right.   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

Money Mistakes You’ll Regret and How to Avoid Them 09.11.2023

“Learn from the mistakes of others. You can’t live long enough to make them all yourself.” – Eleanor Roosevelt… Ever wish you could foresee financial missteps before they happen? In today’s episode, explore some real-life stories of regret and arm yourself with the essential dos and don'ts to ensure your money works for you, not against you.   Show Notes & Info: Schedule A Call With Scott: tal...

Navigating Finances After Losing a Spouse: Strategies & Mistakes to Avoid 19.10.2023

Losing a spouse is an unimaginably tough life event, but the financial implications can add another layer of stress to the grieving process. In this episode, we delve deep into the most common financial issues faced by widows and widowers, from dealing with income gaps to navigating tax changes as a single filer. We explore actionable strategies to address these problems, such as the importance of...

Getting To Know You: Food Edition 05.10.2023

We have a special edition of the podcast today! If you've been listening to the show for a while, you know that Scott and Walter talk about food quite often, so we thought it would be a fun idea to compile a few getting to know you questions from past episodes that were food related. We will get back to the financial talk next episode, so sit back and enjoy something a little different this time a...

Exposing Retirement Planning Complaints 21.09.2023

In this episode, we tackle the common complaints and fears about financial situations during retirement. We'll discuss which concerns are well-founded, which are based on misconceptions, and offer insight on how retirees can best navigate their financial future.   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/  

Building An Estate Plan With No Regrets 07.09.2023

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 the common estate planning mistakes. In this episode, we cover topics ranging from poor expense planning to outdated beneficiary designations and family conflict triggers. We also shed light on some misconceptions about transferring real estate and explain the imp...

Spotting Problematic Personalities of Rogue Advisors 17.08.2023

Finding a trustworthy and competent financial advisor is essential for securing your financial future. After all, they play a vital role in helping you make informed decisions about your money, investments, and long-term financial goals. But how can you separate the wheat from the chaff? How can you identify problematic personalities that might indicate an advisor isn't the right fit for you? We’l...

Mastering Retirement Cash Flow (Part 2): Understanding Income 03.08.2023

Get ready for part two of our Retirement Cash Flow series! This time, we're diving into the income side of the equation. In part one, we tackled the ins and outs of your expenses in retirement. Now, it's all about understanding the crucial role of income analysis. We'll uncover the secrets of guaranteed income versus the uncertain stuff and shed light on the consequences of retiring without a clea...

Counterintuitive Advice: Why You Should NOT Invest In A 401(k) 20.07.2023

Don’t get us wrong. In many cases, your 401(k) can be your best investment vehicle, offering numerous benefits and tax advantages and many times a 100% return on some of your contributions (also known as an employer match). However, it's important to recognize that it might not always be the optimal choice for everyone. Join us in this thought-provoking episode as we dissect the reasons why someon...

Mastering Retirement Cash Flow (Part 1): Understanding Changing Expenses 06.07.2023

In this episode, we’ll explore many of the expenses in your life that might drastically change (one way or another) in retirement. We’ll break those expenses down further to see which ones are the top priorities and analyze some of the other factors that impact your cash flow in retirement.  Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pag...

Retiring With Honors: Financial Planning Lessons From The Classroom 15.06.2023

From time to time, we like to look at issues faced by people in other professions outside of the financial world and see what kind of retirement planning lessons we can learn from these other professions. Today, we’re seeing what we can learn from teachers and the issues they face.   Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusions...

Trust The Experts? Breaking Down Commentary Surrounding The String Of 2023 Bank Collapses 01.06.2023

Silicon Valley, Credit Suisse, and First Republic are just a few banks that have experienced either incredible turmoil or complete collapse in the past few months. How should the average American respond with their money? Do you pull it all out in cash and store it under your bed? Should you throw all your money into depressed bank stocks in hopes of riding a wave back up in case a recovery occurs...

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