Month: September 2026
Is It Worth It To Convert Your IRA To A Roth?

Is It Worth It To Convert Your IRA To A Roth?

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Should you convert your traditional IRA to a Roth IRA? In this YSR FAQ episode, Dennis O’Keefe breaks down the pros and cons of Roth conversions and explains why the answer depends heavily on your tax situation.

Dennis discusses how Roth conversions are taxed, the importance of understanding tax brackets, and why many investors benefit from a multi-year conversion strategy rather than making one large move. He also examines some of the common misconceptions surrounding Roth conversions and why generic online calculators can sometimes produce misleading results.

For those thinking about tax-efficient retirement income or leaving assets to the next generation, this episode provides valuable insight into when a Roth conversion may, or may not, be beneficial.

Key takeaways:

  • How Roth conversions work
  • Why tax brackets are critical to the decision
  • Potential tax pitfalls to avoid
  • Multi-year conversion strategies
  • The estate planning benefits of Roth assets
  • And more!

Connect with Dennis O’Keefe: 

All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.
How Often Should I Check My 401(k)?

How Often Should I Check My 401(k)?

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How closely should you monitor your retirement accounts? 

In this YSR FAQ episode, Dennis O’Keefe explains why both neglecting your 401(k) and obsessively checking it can create problems.

Using examples from his own experience and lessons from past market cycles, Dennis discusses the importance of reviewing account allocations, maintaining proper diversification, and periodically rebalancing your portfolio. He also shares a story from the early days of online 401(k) trading and explains why constantly reacting to market movements can be counterproductive.

If you’re unsure how often you should review your retirement savings or what you should actually be looking for when you do, this episode offers a practical framework.

Key takeaways:

  • How often to review your 401(k)
  • The importance of monitoring asset allocation
  • When rebalancing may be necessary
  • Why daily account watching can be harmful
  • How market volatility should influence your review process
  • And more!

Connect with Dennis O’Keefe: 

All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.
How to Buy Your Next Car Without Overpaying (Ep. 143)

How to Buy Your Next Car Without Overpaying (Ep. 143)

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Thinking about buying a car? It can feel overwhelming, especially when prices, financing, trade-offs, and dealership tactics all compete for your attention. 

How do you know you’re paying a fair price, and what steps can help you avoid expensive mistakes before you sign?

In this episode, Dennis O’Keefe shares practical strategies to help you make more confident car-buying decisions. He explains why keeping your current vehicle longer can often save more than upgrading, how thorough research changes negotiations, considerations when evaluating a lease, and why buying used may offer meaningful advantages. Dennis also walks through negotiating over the phone, comparing total ownership costs instead of monthly payments, and researching rebates before stepping into a dealership.

Key takeaways:

  • Why keeping your current vehicle longer can often reduce long-term ownership costs and financial stress.
  • How researching pricing, reliability, recalls, and ownership costs changes your buying position.
  • What lease agreements often hide beyond the advertised monthly payment and why it matters.
  • Why buying a used vehicle can reduce depreciation and avoid early ownership headaches.
  • How negotiating remotely and verifying incentives helps compare offers more accurately.
  • And more!

Connect with Dennis O’Keefe: 

All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.