You spent decades saving for retirement, but what if the biggest risk is not how much you saved, but how you use it?
In this episode, Ryan Thacker and Tyson Thacker break down what they see most people get wrong about retirement planning, especially in the critical years right before and after retirement. They explain why saving money and planning for retirement are two very different things, and how small, uncoordinated decisions around taxes, Social Security, investments, and healthcare can quietly erode your wealth over time.
Ryan and Tyson discuss:
Why the retirement red zone is where small mistakes become costly
How taxes act as a ripple effect across Social Security, Medicare, and income
Why over 90 percent of Americans file for Social Security the wrong way
The danger of taking too many risks late in your career
How healthcare costs can derail even well-funded retirements
Why coordinated planning matters more than chasing investment returns
And more
Share Your Story or Question: What’s your biggest retirement concern? Email us at info@bossretirement.com or leave a voicemail, and we might feature your question in an upcoming episode.
One of the biggest retirement mistakes has nothing to do with how much you saved, it’s about where your income comes from once you stop working. The order you withdraw your money can quietly trigger higher taxes, bigger Medicare premiums, and unnecessary stress later in life.
In this episode, Ryan Thacker and Tyson Thacker break down why withdrawal strategy is one of the most overlooked yet impactful decisions in retirement planning, and how a single misstep can set off a chain reaction that affects your taxes, Social Security, and long-term income.
Ryan and Tyson discuss:
Why the order you pull money from IRAs, 401(k)s, Roth accounts, and brokerage accounts matters more than most people realize
How withdrawals can unintentionally increase taxes on Social Security and trigger IRMAA Medicare surcharges
Common mistakes retirees make by relying on outdated rules of thumb like the 4% rule
How delaying or mismanaging withdrawals can lead to larger required minimum distributions later
What a coordinated withdrawal strategy looks like and how it helps protect income, taxes, and peace of mind
Most people watch their account balances closely, but very few know the number that matters most in retirement: how much they will actually owe in taxes. That number can change everything about what you can spend, how long your money lasts, and the choices you get to make in the years ahead.
In this episode, Ryan Thacker and Tyson Thacker walk through the real tax challenges facing retirees and why so many families are caught off guard. They explain why taxes often rise in retirement, how different income streams are taxed, and why understanding your tax buckets can help you avoid unnecessary surprises.
Ryan and Tyson discuss:
The three tax buckets and how each one affects your retirement income
Why most retirees underestimate their future tax bill
How RMDs, Social Security, pensions, and investment income interact
The power of tax bracket management and Roth strategies
The long-term impact of delaying tax planning
How forward-looking tax analysis can help families keep more of what they saved
As the year ends, many retirees review their financial decisions in light of changing tax rules, market movement, and ongoing cost pressures.
In this episode, Ryan Thacker and Tyson Thacker outline five Smart Money Moves that can help retirees prepare for 2026. Their discussion focuses on practical steps that influence taxes, income, Social Security, investment allocation, and healthcare planning.
Ryan and Tyson cover:
How tax planning can affect long-term retirement outcomes
Ways to create income that is steady and structured
Why Social Security decisions should integrate with the rest of a retirement plan
How portfolio drift occurs after long market runs, and when rebalancing may be useful
Considerations for managing rising healthcare costs
Most retirees focus on how much they have saved, but the biggest threat to their future is often the cost they never planned for. Taxes, inflation, healthcare, and longevity can quietly increase year after year until they place real pressure on your retirement income.
In this episode, Ryan Thacker and Tyson Thacker explain how hidden retirement expenses can erode even the strongest nest eggs and what you can do right now to protect yourself.
Ryan and Tyson discuss:
Why do many retirees end up in a higher tax bracket than expected
How “stealth taxes” like capital gains and lost deductions impact your income
Why inflation makes everyday expenses harder to manage over a 20 or 30-year retirement
The rising cost of healthcare and long-term care
How longer lifespans amplify every other financial risk
The difference between tax preparation and true tax planning
Practical steps to help keep more of your savings working for you
Most people focus on investment returns, but the real threat to a comfortable retirement often hides in plain sight. Taxes can quietly drain away more of your savings than you ever expected, and the window to take control may be smaller than you think.
In this episode, Ryan Thacker and Tyson Thacker break down how today’s historically low tax rates can create a rare opportunity for pre-retirees and retirees. They explain why strategic Roth conversions may help you keep more of your money, how required minimum distributions can trigger bigger tax bills later in life, and why waiting could mean giving up one of the most valuable planning windows available.
Ryan and Tyson discuss:
Why so much retirement savings sits in tax-deferred accounts, and why that can create problems later
How expanded tax brackets in the current law may help you convert more at potentially lower rates
Why timing matters with Roth conversions and how to avoid pushing yourself into higher tax brackets
How proactive planning can help you reduce uncertainty and build more control into your retirement income
What Washington proofing your retirement really means and how to get started before year-end
Why are taxes one of the biggest retirement expenses, and how can you minimize them?
Join Ryan and Tyson Thacker for an episode of Retirement Solutions The Podcast as they discuss how taxes can take a huge bite out of your retirement savings and share strategies to help avoid it. Discover how you often have more control over taxes in retirement than any other time in life.
Ryan and Tyson delve into:
(02:54) Common misconceptions about retirement tax
(06:10) The true cost of tax-deferred savings vehicles, like 401(k)s
(15:22) Strategies for minimizing taxes through Roth conversions and life insurance
(18:34) Changes in tax brackets and how they affect your retirement taxes
(27:11) The benefits of advanced tax planning strategies for retirees
And more!
Tune in and explore how smart tax strategies can save you a substantial amount and keep more of your hard-earned savings in your pocket.
Are you making the most of your wealth opportunities, or are common financial myths holding you back?
In this episode, Tyson and Ryan Thacker chat with Tom Hegna, a renowned economist and bestselling author, to explore why the way we think about wealth might be all wrong. Together, they unravel surprising truths about building financial security and break down the top mistakes many young adults make with their money. Tom shares insights from his latest book and reveals simple strategies you can begin using today. This is a must-listen for anyone interested in securing a financially free future!
Tom discusses:
(04:02) Why understanding the Rule of 72 can be your golden ticket to wealth
(06:22) The common financial traps young adults fall into and how to avoid them
(13:12) Why focusing on income rather than just assets is crucial
(19:06) The importance of tax planning and avoiding a heavy tax burden in the future
Tom Hegna, CLU, ChFC, CASL, is an economist, author, and retirement expert. He has been an incredibly popular industry speaker for many years and is considered by many to be THE Retirement Income Expert!
As a former First Vice President at New York Life, retired Lieutenant Colonel, and economist, Tom has delivered over 5,000 seminars on his signature “Paychecks and Playchecks” retirement approach, helping Baby Boomers and seniors retire the “optimal” way. He has condensed a large chunk of his considerable knowledge into 5 books.
Tom specializes in creating simple and powerful retirement solutions. He has the unique ability to pump up a crowd, make people laugh and solve complex financial problems using easy-to-understand words, ideas and stories. He’s been featured in Business, Forbes, Money Rates, and many other leading publications. He is available to speak with businesses, government organizations, professional associations, financial professionals and their clients across the globe.
Are you ready to simplify the complexities of high-net-worth tax planning and maximize your retirement savings? Today, we unveil key strategies with our expert guest, Jeremy Green.
In this Retirement Solutions The Podcast episode, Tyson Thacker and Ryan Thacker are joined by Jeremy Green, a highly experienced advisor specializing in high net worth tax situations, estate, and business planning. Listen in as Jeremy shares his strategies for managing tax-efficient retirement income and maximizing the value of your financial assets, offering a behind-the-scenes look at how B.O.S.S. Retirement Solutions creates customized retirement plans. Discover actionable strategies for integrating your legal, financial, and tax planning matters and exploring unique opportunities available for those with highly appreciated assets.
Top discussion points include:
The benefits and implications of Roth conversions, life insurance, and other tax-free options for retirement planning
How to approach tax planning with highly appreciated stock and minimize capital gains taxes
The potential impact of upcoming tax changes and how to prepare for them with strategic planning
Examples of successful retirement strategies and the importance of early planning to maximize opportunities
Jeremy Green is a subject matter expert in high-net-worth tax, estate, and business planning with 22 years of experience. He collaborates with professional advisors, closely held business owners, and clients with significant assets to integrate and clarify their business, estate, philanthropic, tax, investment, and life insurance plans.
Over his career, Jeremy has eliminated millions of dollars in unnecessary present and future combined fees, estate, income, and capital gains taxes by restructuring how assets are owned before the sale of businesses or real estate. He has also adjusted business operating agreements to preserve otherwise lost stepped-up tax cost basis, modified the number and complexity of existing trust arrangements, optimized trust, and business-owned life insurance funding, and reduced excessive investment management expenses. Additionally, Jeremy serves as a paid expert witness, testifying on the proper design and execution of tax, wealth, and insurance planning techniques in FINRA three-judge panel arbitration and litigation in the U.S. Federal District Court.
Jeremy is admitted to practice before the IRS as an Enrolled Agent. He is also a Certified Financial Planner®, Certified Trust Financial Advisor, Certified Employee Benefit Specialist, Chartered Life Underwriter, and Accredited Estate Planner. He holds a degree from the Institute of Certified Bankers National Graduate Trust School, the American Institute of Bankers Personal Trust School, and the American College’s Master of Science in Financial Services program.
Did you know that the average retired couple could end up paying hundreds of thousands of dollars in taxes on their retirement savings?
Join Tyson Thacker and Ryan Thacker, as they introduce us to Bob and Carol—representative avatars of the thousands of families they’ve helped navigate retirement through their B.O.S.S. Retirement Blueprint. Gain insights into how personalized retirement planning can not only address but mitigate the significant tax burdens that could impact your golden years. Learn through the example of Bob and Carol’s the importance of tax planning, and how small adjustments today can save significant sums tomorrow!
Ryan and Tyson discuss:
The characters of The B.O.S.S. Retirement Blueprint, and share insights on their retirement challenges
How personal passions and family time shape retirement goals
The impact of taxes on retirement accounts and strategies to minimize them
The differences between tax preparation and tax planning
