Best Jim Cipriotti Podcasts (2025)

1
From Denial to Done: Your Retirement Plan Starts Here 23:09

1d ago23:09

23:09

In this episode of Freedom to Retire, Jim Cipriotti breaks down the critical steps to secure your future before it’s too late. From “deniers” to “planners,” discover which retirement mindset you fall into and why it could make or break your golden years. Jim shares real-life stories and powerful insights that drive home one truth: retirement isn’t …

1
Think Your Roth IRA Is Safe? Think Again. 23:48

5d ago23:48

23:48

In this eye-opening episode of Freedom to Retire, retirement strategist Jim Cipriotti exposes the hidden risks lurking in your Roth IRA. With Washington eyeing tax reforms, the “tax-free” promise may not be as bulletproof as you think. Jim unpacks the misunderstood five-year rules, the threat of required minimum distributions, and why delaying acti…

1
The Retirement Tax Mistake That Could Cost You 24:20

15d ago24:20

24:20

Are hidden tax traps threatening your retirement? In this episode of Freedom To Retire, Jim Cipriotti exposes costly 401(k) withdrawal mistakes and overlooked tax strategies that could derail your financial future. If you're in your 50s or 60s, now is the time to take control. Learn how smart tax planning and proactive financial decisions can prote…

1
Missed the Dip? Here’s What You Can Still Do 30:41

19d ago30:41

30:41

What if a market dip could be your golden opportunity? In this episode of Freedom to Retire, Jim Cipriotti breaks down how Roth conversions during downturns can be a powerful tax-saving strategy. He explains why most investors miss the chance to “buy the dip” and how converting assets when values are low can lead to long-term, tax-free growth. Jim …

1
Is Your Retirement Money Hiding in Plain Sight? 24:15

22d ago24:15

24:15

What if you had thousands of dollars sitting in a forgotten 401(k) and didn’t even know it? In this episode of Freedom to Retire, Jim Cipriotti uncovers the surprising truth about lost retirement accounts and how to reclaim them. From real-life stories to practical tools like unclaimedretirementbenefits.com and missingmoney.com, Jim walks listeners…

1
Your 401(k) Is Growing—So Are the Risks 26:07

26d ago26:07

26:07

What if the tax-free promise of your Roth IRA isn’t as ironclad as you think? In this episode of Freedom to Retire, Jim Cipriotti tackles the growing concern about potential changes to Roth taxation and why now might be the smartest time to act. From misunderstood five-year rules to the looming impact of required minimum distributions, Jim breaks d…

1
From 59½ to 73: The Milestones That Matter Most 25:47

29d ago25:47

25:47

What if the key to a confident retirement lies in knowing just a few critical age milestones? In this episode of Freedom to Retire, Jim Cipriotti breaks down the essential ages that shape your retirement journey—from catch-up contributions at 50 to RMDs at 73 and beyond. Learn how Social Security timing, Medicare enrollment, and income strategies l…

1
A Love Letter Through Legacy: Planning Beyond the Numbers 23:48

1M ago23:48

23:48

What kind of legacy will you leave behind? In this heartfelt episode, Jim Cipriotti reflects on the life and legacy of George Wendt—not just as a public figure, but as a reminder of what it means to plan with purpose. Jim dives into how legacy planning is more than numbers—it’s a lasting love letter to your family. From often-overlooked beneficiary…

1
Social Security Shake-Up: What Retirees Need to Know Now 29:22

1M ago29:22

29:22

Is Social Security About to Change Forever? What Every Retiree Needs to Know! With 27 years of experience, Jim Cipriotti breaks down a potentially game-changing proposal: the possible elimination of taxes on Social Security benefits. What could this mean for your retirement income? Jim also takes a hard look at the current state of Social Security …

1
Navigating Financial Decisions in Your 50s and 60s 24:20

1M ago24:20

24:20

Jim Cipriotti emphasizes the critical role of tax planning in retirement, highlighting common mistakes individuals make, particularly regarding 401k withdrawals and the implications of taxes on retirement income. The discussion also covers the importance of financial planning for those in their 50s and 60s, addressing key decisions that can impact …

1
The Risks of Market Timing 27:30

1M ago27:30

27:30

Jim Cipriotti delves into the complexities of retirement planning amidst market fluctuations, emphasizing the importance of having a solid financial strategy. He discusses the risks of trying to time the market, the variety of financial instruments available for safety, and the necessity of professional management. This episode also highlights the …

1
Long Term Planning to Avoid Low-Interest Returns 25:46

2M ago25:46

25:46

In this conversation, Jim Cipriotti discusses various aspects of retirement planning, focusing on market reactions to tariffs, investment strategies, tax planning techniques, and the importance of annuities and income planning for retirees. He emphasizes the need for a diversified portfolio and the significance of understanding one's financial inst…

1
Psychology of Money and Market Fluctuations 28:19

2M ago28:19

28:19

Jim Cipriotti explores the current economic climate, focusing on the implications of tariffs, recession predictions, and their effects on retirement planning. Jim delves into the psychology of money, the importance of understanding market risks, and the need for strategic financial planning, especially as individuals approach retirement. The discus…

1
Retirement Planning in Uncertain Times 27:35

2M ago27:35

27:35

Jim Cipriotti delves into the impact of market volatility on investments, particularly in light of recent tariffs imposed by President Trump. Jim discusses the emotional responses of investors, the importance of maintaining a long-term perspective, and strategies for navigating retirement planning amidst financial uncertainty. The discussion also h…

1
The Truth About Bonds and Retirement 28:45

3M ago28:45

28:45

In this episode, Jim Cipriotti discusses the current state of retirement planning amidst market volatility, focusing on the implications of bond market trends, the role of target date funds, and the increasing popularity of annuities. He emphasizes the importance of making informed financial decisions rather than emotional ones and provides insight…

1
Strategies for Maximizing Social Security 27:20

3M ago27:20

27:20

On this episode of 'Freedom to Retire', Jim Cipriotti discusses essential strategies for retirement planning, focusing on Social Security benefits, the importance of financial planning, and the advantages of Roth IRAs. He emphasizes the need for individuals to understand their options regarding Social Security, including when to claim benefits and …

1
Planning for Longevity: Financial Strategies for the Future 35:53

3M ago35:53

35:53

Jim Cipriotti explores the rising costs of lottery tickets and the importance of strategic retirement planning. It emphasizes the need for individuals to prepare for longevity in retirement, the significance of tax planning, and the benefits of utilizing Roth IRAs. The discussion also highlights the necessity of understanding income taxes related t…

1
The Risks of Conventional Financial Wisdom 37:20

4M ago37:20

37:20

Jim Cipriotti delves into the complexities of financial planning, particularly focusing on retirement income strategies, the importance of personalized advice, and the implications of market volatility and taxes on investment decisions. Jim emphasizes the need for tailored financial strategies rather than one-size-fits-all solutions, highlighting r…

1
Understanding Risk, Market Fluctuations, and The Role of Financial Advisors 25:55

4M ago25:55

25:55

Jim Cipriotti delves into the complexities of retirement planning, focusing on risk tolerance, market volatility, and the importance of financial advisors. The discussion highlights how market conditions can influence individuals' perceptions of risk and the potential dangers of not understanding one's risk tolerance. Strategies for protecting reti…

1
Navigating Retirement: Strategies for a Smooth Transition 25:57

4M ago25:57

25:57

Jim Cipriotti discusses the challenges retirees face when transitioning from a steady paycheck to relying on savings. He emphasizes the importance of understanding investment risks, particularly in volatile markets, and the necessity of effective tax planning to maximize retirement savings. Jim also highlights the benefits of utilizing Roth account…

1
The Future of Social Security: What You Need to Know 24:38

4M ago24:38

24:38

Jim Cipriotti discusses the complexities of retirement planning, focusing on the challenges posed by Social Security taxation, the importance of diversified income streams, and the impact of market volatility on retirement savings. He emphasizes the need for individuals to take control of their retirement planning and explore various financial inst…

1
The five-year clock started on January 1st! 25:03

4M ago25:03

25:03

Jim Cipriotti delves into the complexities of Roth IRAs, conversions, and the importance of comprehensive financial planning. Jim clarifies common misconceptions about the five-year rule for Roth accounts, discusses the tax benefits of Roth conversions, and emphasizes the need for a holistic approach to retirement planning that includes tax strateg…

1
You can create your very own pension. 27:18

5M ago27:18

27:18

Jim Cipriotti discusses the importance of creating a personal pension for retirement, especially in the absence of traditional pensions. The discussion covers various income sources, including social security, annuities, and 401(k) plans, emphasizing the need for a strategic financial plan. Jim also touches on estate planning, highlighting insights…

1
How should I structure my withdrawals? 26:41

5M ago26:41

26:41

Jim Cipriotti delves into the complexities of managing inherited IRAs, particularly focusing on tax implications and withdrawal strategies. The discussion highlights the importance of understanding individual circumstances when it comes to tax brackets and the timing of withdrawals. It also emphasizes the necessity of consulting with financial advi…

1
Strategies for Sustainable Income in Retirement 29:31

5M ago29:31

29:31

Jim Cipriotti explores the financial behaviors and concerns of Baby Boomers as they approach retirement. It discusses their reluctance to spend their amassed wealth, the importance of tax planning, the risks associated with market fluctuations, and strategies for ensuring sustainable income during retirement. The speaker emphasizes the need for a c…

1
Handling Unexpected Windfalls 29:48

5M ago29:48

29:48

Jim Cipriotti discusses various aspects of retirement planning, including how to handle unexpected financial windfalls, investment strategies, estate planning, and the importance of creating a sustainable income for retirement. He emphasizes the need for a comprehensive financial plan that considers longevity, social security, and the lack of pensi…

1
The Risks of Bond Funds 28:41

5M ago28:41

28:41

Jim Cipriotti discusses the evolving landscape of retirement planning, emphasizing the importance of understanding alternative investments, tax strategies, and the risks associated with traditional bond funds. He highlights the need for comprehensive planning to ensure that retirement savings last through increasing life expectancies, while also ad…

1
Stocks for growth, bonds for income, cash for safety. 30:08

6M ago30:08

30:08

Jim Cipriotti discusses the evolving landscape of retirement planning, emphasizing the importance of understanding alternative investments, the challenges posed by traditional bond funds, and the necessity of planning for longevity in retirement. He highlights the significance of financial advisors in navigating these complexities and ensuring a st…

1
Exploring Annuities: Pros and Cons 26:42

6M ago26:42

26:42

Jim Cipriotti delves into the critical aspects of retirement planning, emphasizing the necessity of having a solid income strategy. It highlights the common pitfalls that retirees face, such as living too frugally or being overly cautious with their savings. The discussion also explores the concept of the 'Great Retirement' and the challenges many …

1
The Bond Market: What You Need to Know 27:47

6M ago27:47

27:47

Jim Cipriotti discusses the importance of setting financial goals for the new year, the current market trends, and the role of bonds in investment strategies. He emphasizes the need for guaranteed income in retirement and explores the benefits of annuities as a solution for securing a stable income stream. The conversation highlights the challenges…

1
Understanding the American Dream in Today's Economy 26:47

7M ago26:47

26:47

Jim Ciprioti discusses the complexities of Social Security, the challenges of achieving the American dream, and the importance of comprehensive retirement planning. He emphasizes the need for personalized financial advice and the significance of understanding Social Security benefits, retirement income strategies, and tax implications. Listeners ar…

1
You can still transfer some of that 401k 27:33

7M ago27:33

27:33

Jim Cipriotti discusses the current state of retirement planning amidst market volatility, the importance of understanding financial instruments, and the benefits of annuities. He emphasizes the need for individuals to take control of their retirement accounts and explore options that can provide security and growth. The conversation also highlight…

1
Understanding the fees associated with retirement accounts 50:36

7M ago50:36

50:36

Jim Cipriotti discusses the current state of retirement planning, market predictions for 2025, and the importance of understanding fees associated with retirement accounts.The conversation also addresses the challenges of inheritance and the potential tax burdens on heirs, urging listeners to consider Roth IRAs as a tax-efficient option for passing…

1
Understanding Annuities: A Modern Approach 40:51

8M ago40:51

40:51

Jim Cipriotti discusses the essential components of retirement planning, emphasizing the importance of guaranteed income, the evolution of annuities, and the critical role of tax planning. He shares insights on market trends, investment strategies, and the significance of structured notes. Catch Freedom To Retire with Jim Cipriotti, powered by Reti…

1
You can add another super catch up 49:54

8M ago49:54

49:54

Jim Cipriotti discusses the current state of the market, the importance of strategic retirement planning, and the new rules regarding 401k contributions. He emphasizes the need for individuals nearing retirement to consider their investment strategies carefully, especially in light of market highs and potential risks. The conversation also highligh…

1
The Future of I Bonds: What You Need to Know 41:42

8M ago41:42

41:42

Jim Cipriotti discusses various aspects of retirement planning, focusing on the current economic landscape, the performance of I bonds and bond funds, and the importance of cash flow and tax planning for retirees. In this conversation, Jim discusses the importance of understanding market trends, and the risks associated with retirement investments.…

1
Navigating the 4% Rule: A Retirement Guide 25:10

8M ago25:10

25:10

Jim Cipriotti discusses the 4% rule for retirement withdrawals and its alternatives, emphasizing the importance of personalized financial planning. He shares insights on navigating retirement income, tax strategies, and preparing for future tax changes, particularly in light of the potential expiration of the Trump tax cuts. The conversation highli…

1
Navigating Year-End Financial Chaos 22:55

8M ago22:55

22:55

Jim Cipriotti discusses the importance of year-end financial planning as 2024 comes to a close. He emphasizes the need for listeners to check off their financial chores, such as maximizing contributions to 401ks and HSAs, and exploring tax strategies like tax loss harvesting. Jim also highlights the current interest rate environment and the benefit…

1
The Impact of Elections on Investments 33:12

9M ago33:12

33:12

Jim Cipriotti discusses the current state of the markets, the importance of strategic retirement planning, and how upcoming elections may impact investment decisions. Jim also highlights the significance of staying invested in the market despite political uncertainties and offers insights into optimizing cash flow for a more secure retirement. Catc…

1
The Impact of Market Conditions on Retirement 46:11

9M ago46:11

46:11

Jim Ciprioti discusses the intricacies of retirement planning, focusing on withdrawal rates, market conditions, and the importance of having a solid financial strategy. The discussion also covers the current economic climate, interest rates, and the various financial instruments available to retirees, highlighting the importance of consulting with …

1
Tax Strategies for a Secure Retirement 29:41

9M ago29:41

29:41

Jim Ciprioti discusses the current state of the market, the importance of comprehensive financial planning, and effective tax strategies for retirement. He shares insights on market trends, client case studies, and the necessity of having a financial advisor to navigate the complexities of retirement planning. The conversation emphasizes the need f…

1
Inherited IRAs: What You Need to Know 30:10

9M ago30:10

30:10

Jim Ciprioti discusses various aspects of retirement planning, including the impact of political events on finances, the implications of early withdrawals from retirement accounts, and the importance of tax planning. He emphasizes the need for a comprehensive financial strategy to navigate required minimum distributions (RMDs) and manage debt effec…

1
Understanding the Impact of Fed Rate Cuts 30:54

10M ago30:54

30:54

Jim discusses the current landscape of retirement planning, focusing on the recent Federal Reserve interest rate cuts and their implications for retirement savings. He emphasizes the importance of long-term financial strategies, particularly in a fluctuating interest rate environment. He also covers Social Security benefits, including strategies fo…

1
Professional Guidance in Financial Health 17:21

10M ago17:21

17:21

Jim Cipriotti discusses the complexities of retirement planning, emphasizing the importance of having a comprehensive financial strategy. He highlights the challenges faced by retirees who manage multiple financial advisors and the need for a one-stop solution for financial guidance. Jim shares insights on retirement income, tax strategies, and the…

1
Federal Reserve's Interest Rate Cuts and Economic Outlook 29:57

10M ago29:57

29:57

Jim Cipriotti delves into the recent interest rate cuts by the Federal Reserve and their implications for the economy and investment strategies. Financial advisors play a crucial role in helping individuals maximize returns while minimizing risks, especially as they approach retirement. The conversation emphasizes the need for a strategic approach …

1
Current Market Trends and Interest Rates 26:26

10M ago26:26

26:26

Jim highlights the significance of strategic retirement planning, considering the prevailing market trends and interest rates. He underscores the necessity for individuals to comprehend their retirement income requirements and to explore different investment strategies, such as annuities, to ensure a steady income throughout retirement. Catch Freed…

1
Transitioning Investments for a Secure Retirement 24:46

10M ago24:46

24:46

Jim Cipriotti from Retire Ready Financial Group emphasizes the significance of shifting investments to those tailored for retirement, providing insights into various investment alternatives. He discusses the dangers of depending solely on 401(k) investments and underscores the importance of exploring other accounts that provide monthly income. Addi…

1
Managing Finances in a Volatile Economy 25:17

11M ago25:17

25:17

Jim Cipriotti addresses the current economic climate and the effects of inflation on retirement planning. He recommends managing your finances by seeking higher interest rates for short-term savings and making informed investment choices. Additionally, he highlights the necessity of preparing for retirement costs and aligning retirement funds with …

1
Considering Tax Brackets in Inheritance Planning 15:46

11M ago15:46

15:46

Jim explains the significance of taking tax brackets into account during inheritance planning and recommends transitioning to a Roth account as a strategy to potentially reduce tax liabilities. Catch Freedom To Retire with Jim Cipriotti, powered by Retire Ready Financial Group every Saturday at 9:00 AM and Sunday at 5:00 PM ET on WPHT. For more inf…

1
Preparing for Market Downturns and Weathering the Storm 27:06

11M ago27:06

27:06

Recent stock market fluctuations have impacted retirement savings. Jim Cipriotti stresses the importance of remaining calm and adhering to one's investment strategy, while also underscoring the necessity of being prepared for possible market downturns. Catch Freedom To Retire with Jim Cipriotti, powered by Retire Ready Financial Group every Saturda…

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