Retirement Toolbox

Hosted by Scott Searles

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Episodes

151

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Nov 2025

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About the show

Welcome to Retirement Toolbox, the podcast designed to help you build a strong financial foundation and navigate retirement with clarity and confidence. Hosted by Scott Searles, financial advisor and founder of Skybox Financial Group, this show offers straightforward, practical insights to help you protect what you’ve earned, grow your wealth for the future, and reduce your lifetime tax burden. Whether you’re approaching retirement or already enjoying it, tune in for education on income planning, tax-smart strategies, investment decisions, and more. Subscribe now and never miss an episode! For more information, visit https://www.skyboxfinancialgroup.com or call 888-742-0111.

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60 recent

November 6, 2025Episode 15013 min

Fidelity’s Latest Data: Health Care in Retirement Is More Expensive Than Ever

Fidelity just released their 2025 Retiree Health Care Cost Estimate. The number is staggering: $172,500 for a 65-year-old retiring today. The bigger problem? One in five Americans haven’t even thought about health care costs in retirement. Today we’ll break down what this means, why it matters, and how to prepare. Resources: Our website: https://skyboxfinancialgroup.com/ Phone: 888-742-0111 Contact our team: https://skyboxfinancialgroup.com/contact-us/ Schedule your no-cost consultation: https://skyboxfinancialgroup.com/schedule/ Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Check out our other no-cost financial resources here: https://skyboxfinancialgroup.com/blog-2/ Facebook: https://www.facebook.com/skyboxfinancialgroup/ LinkedIn: https://www.linkedin.com/in/scottsearles/ X: https://x.com/skyboxfinancial

August 28, 2025Episode 1497 min

Are You Retirement Ready? Take The Quiz!

The kids may be heading back to class, but it’s a perfect time for adults to crack open the books too, especially when it comes to retirement. In this episode, Scott puts listeners to the test with a series of essential retirement planning questions every retiree should know. Here are your pop-quiz questions: ✏️ At what age can you receive full Social Security benefits if born after 1960? ✏️ What is the IRA contribution limit for those 50 or older in 2025? ✏️ Which retirement accounts require RMDs? ✏️ What does the 4% rule refer to in retirement planning? ✏️ What financial risks do many retirees face? Resources: Our website: https://skyboxfinancialgroup.com/ Phone: 888-742-0111 Contact our team: https://skyboxfinancialgroup.com/contact-us/ Schedule your no-cost consultation: https://skyboxfinancialgroup.com/schedule/ Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Check out our other no-cost financial resources here: https://skyboxfinancialgroup.com/blog-2/ Check us out on YouTube: https://www.youtube.com/channel/UCsO-3BlgeTmU-I2OPfvH6SQ Facebook: https://www.facebook.com/skyboxfinancialgroup/ LinkedIn: https://www.linkedin.com/in/scottsearles/ X: https://x.com/skyboxfinancial

August 7, 2025Episode 1483 min

Don't Fall For These Big Beautiful Bill Myths

Big tax law changes always bring big rumors. But before you assume Social Security is now tax-free or that you’re getting a $40K deduction just for breathing, let’s set the record straight on what this new bill didn’t actually do. In this episode, Scott busts the biggest myths surrounding the recent “Big Beautiful Bill,” breaking down the fine print behind headline-grabbing claims. Here’s some of what we discuss in this episode: 💸 What the Social Security changes actually mean 🧾 The truth behind the “everyone gets a tax cut” myth 🏛️ Why “permanent” tax rules aren’t really permanent 📜 Estate taxes aren’t dead in every state 🚗 The car loan deduction is temporary and restricted Resources: Our website: https://skyboxfinancialgroup.com/ Phone: 888-742-0111 Contact our team: https://skyboxfinancialgroup.com/contact-us/ Schedule your no-cost consultation: https://skyboxfinancialgroup.com/schedule/ Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Check out our other no-cost financial resources here: https://skyboxfinancialgroup.com/blog-2/ Check us out on YouTube: https://www.youtube.com/channel/UCsO-3BlgeTmU-I2OPfvH6SQ Facebook: https://www.facebook.com/skyboxfinancialgroup/ LinkedIn: https://www.linkedin.com/in/scottsearles/ X: https://x.com/skyboxfinancial

July 31, 2025Episode 1478 min

What The “Big Beautiful Bill” Means For Your Retirement Plan

You’ve probably heard about the “Big Beautiful Bill,” but what does it actually mean for your retirement plan? In this episode, Scott breaks down the real implications of the new legislation, beyond the headlines and political noise. He walks you through what changed, what didn’t, and the planning opportunities that smart retirees should be acting on now, while the tax rules are favorable. Here’s some of what we discuss in this episode: 📊 Tax brackets are staying lower- for now 🎁 New deduction for seniors 65+ 🔁 Roth conversions are still a major planning opportunity 🏗️ 100% bonus depreciation for business owners and landlords 🚨 Some of these breaks expire in 2028- act while you can Resources: Our website: https://skyboxfinancialgroup.com/ Phone: 888-742-0111 Contact our team: https://skyboxfinancialgroup.com/contact-us/ Schedule your no-cost consultation: https://skyboxfinancialgroup.com/schedule/ Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/ Check out our other no-cost financial resources here: https://skyboxfinancialgroup.com/blog-2/ Check us out on YouTube: https://www.youtube.com/channel/UCsO-3BlgeTmU-I2OPfvH6SQ Facebook: https://www.facebook.com/skyboxfinancialgroup/ LinkedIn: https://www.linkedin.com/in/scottsearles/ X: https://x.com/skyboxfinancial

April 17, 2025Episode 14622 min

Key 2025 Tax Breaks & Adjustment Opportunities

Tax season is here, but filing your 2024 return is just one piece of the puzzle. Now is also the perfect time to take advantage of new tax rules for 2025—before the year gets away from you. With higher standard deductions, increased retirement contribution limits, and updated HSA rules, there are plenty of opportunities to lower your tax bill and boost your savings. In this episode, we’ll break down the key changes and how you can start planning now to make the most of them. Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

April 3, 2025Episode 14522 min

April Fool’s: Beliefs That Fool Retirement Savers The Most

April Fool’s Day is all about jokes and pranks, but when it comes to retirement planning, getting fooled can cost you real money. Today, we’re uncovering the beliefs that fool retirees and pre-retirees into making bad financial moves. Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

March 20, 2025Episode 14422 min

Presidential Wisdom For Your Retirement Plan

Presidents aren’t just leaders of a nation. They’re decision-makers who navigate uncertainty, make tough calls, and plan for the future. Today, we’re looking at how the leadership lessons of some of America’s greatest presidents can help you build a smarter, more secure retirement plan. Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

March 6, 2025Episode 14326 min

What Do Proposed Tariffs Mean For Your Portfolio?

The day President Trump took office, he announced plans to implement a 25 percent tariff on goods from Mexico and Canada. Additional tariff conversations have exploded since that day. How might this impact your personal finances and the economy? Today, we’ll explain a bit of the backstory of tariffs and discuss these new tariffs. Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

February 20, 2025Episode 14223 min

The Snowbird Retirement: Is a Seasonal Move Right for You?

Brrr, it’s cold out there! Winter has a lot of people thinking about warmer weather. For some, that just means an annual vacation down south. But for certain retirees, they choose to live elsewhere through the brunt of winter, becoming “snowbirds.” Is snowbird life for you? Let’s talk about what motivates people to take up temporary residence elsewhere, where they go, and if it’s worthwhile. Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

February 6, 2025Episode 14127 min

5 Financial Mistakes to Avoid in Your 60s

Financial mistakes can happen at any age, but they can have a particularly significant impact in your 60s. This episode offers five common financial blunders to avoid during this pivotal decade. Show Notes & Info: Schedule A Call With Scott: talkwithscott.net Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/