The Rob Berger Show

The Rob Berger Show

Personal finance for smart people by the host of the Dough Roller Money Podcast. Rather than forcing you into a one-size-fits-all financial plan, we discuss the tools, resources, and strategies that will empower you to make the best money decisions for you and your family.

Episodes

April 24, 2026 29 mins

In today's Five Question Friday (FQF) video, we cover these questions: 

1. Floor & Enjoy Retirement Strategy
2. Target Date Funds
3. Paying Taxes on Roth Conversions
4. Vanguard’s New BondBuilder ETFs
5. Boldin vs. Empower

Resources From Video
Empower: https://go.robberger.com/empower/yt-fqf
Boldin: https://go.robberger.com/boldin/yt-fqf
https://longevity.stanford.edu/wp-con......

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In this Five Question Friday (FQF) video, we cover these questions:

1. How to teach your significant other to manage the investments? (The Spouse Financial Survival Kit)
   1. Start with a One-Pager
      a. Accounts
      b. Key Professionals
      c. Withdrawal Order
      d. Financial Overview Doc: https://docs.google.com/document/d/1W...
   2. Financial Love Letter
https://docs.google.com/d...

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In this episode, I'll answer the following question from a viewer:

"I would like to ask if you can do a video on the current specific funds you are invested in? You did a video a while back about your 6 funds, but now you mentioned in a recent video that you simplified and are down to 3 or 4 funds. I was thinking of mirroring your 6 fund plan but now I see you have simplified, which is why I am asking if you can ...

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In today's Five Question Friday (FQF) video, we cover these questions:

1. Where is the best place to park cash today?
2. Should you invest or pay off student loans?
3. Are Schwab’s Target Date Retirement Funds a solid option?
4. When should you start spending your IRA money?
5. Should a TIPS ladder be part of a retirement portfolio?

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February 3, 2026 25 mins

In this episode,  we cover my Ultimate Retirement Checklist:

1. Healthcare

2. Start learning about Medicare

3. Understand IRMMA brackets

4. Track Expenses

5. Calculate Your Burn Rate

6. Calculate Your Guaranteed Income Ratio

7. Plan for large expenses

8. Plan when to take Social Security

9. Cash

10. Create a Tax-Efficient Withdrawal Strategy

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In today's Five Question Friday (FQF) video, we cover these questions: 

1. How do you protect your portfolio as you near retirement?
2. How does asset location work if you must draw from taxable accounts?
3. Should you automatically reinvest dividends?
4. How can I diversify away from the S&P 500?
5. What is the safe withdrawal rate for a 20 year retirement?


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In today's Five Question Friday (FQF) video, we cover these questions:

1. What Happens To Bond Funds When the Fed Cuts Rates?
2. Where to Invest If Stocks Are a No-go
3. How are Mutual Fund Sales Taxed?
4. Should Annuities Replace Bonds?
5. Brokerage Account vs Roth IRA

Resources

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In this 2025 Year-End Investment Portfolio Review we cover the following topics:

1. Asset Allocation
    a. Diversification / changes
    b. Rebalancing
2. Simplification
3. Beneficiaries
4. Performance
5. Tax Loss or Gain Harvesting
6. Fees
    a. Fund fees
    b. Advisor fees
7. Evaluate Your Performance
    a. Did you buy/sell anything
    b. What worried you during the ye...

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In today's Five Question Friday (FQF) video, we look at these five topics:

1. 10% yield on bonds
2. Where to hold bonds
3. Co-signing a mortgage
4. Paying taxes on a Roth conversion
5. Asset allocation of real estate investments
Bonus: Cost of long-term care calculator

Resources:
https://www.carescout.com/cost-of-care

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In today's Five Question Friday (FQF) video, we look at these five questions:

1. Have we been lied to about our Social Security break-even age?

2. Is it ok to restart the 4% rule if the market goes up in early retirement?

3. I am nervous about the run up in AI stocks . . . Could it be a good idea to consider diversifying from VTI to an “equal-weighted index fund like Invesco S&P Equal Weight ETF ...

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October 21, 2025 28 mins

In today's Five Question Friday (FQF) video, we cover these questions:

1. How to invest $15 million?

2. For the 4% withdrawal rate devised by Bill Bengen, what measure of inflation did he use?  Are there other measures that you think might be more appropriate?

3. If you have a retirement portfolio with a 6% yield does the 4% rule apply?

4. Is a 7-year MYGA a better deal than a 7-year Treasur...

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In today's Five Question Friday (FQF) video, we cover this questions:

1. Can you recommend a detailed tax estimator?
2. How to plan Roth conversions without a fancy retirement planner?
3. Should you pay off a mortgage early or invest the money?
4. Are identity theft protection services worth the cost?
5. How does reinvesting vs spending dividends affect return assumptions for retirement planning?
 ...

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September 26, 2025 128 mins

Get free guidance on Medicare from Chapter, a company I've partnered with, by calling 410-220-5494. If you call Chapter, please let me know about your experience.

It's Not That Complicated https://drive.google.com/file/d/1Hqs4v7wLCjhh5ohWVVSNTs2HsGz9nufD/view

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https://robberger.com/newsletter/?utm...

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In this episode, we'll walk through resources you can use to get free help with Medicare. The Resources are broken into three categories:

1. Free online educational content
2. Free Medicare guidance from SHIP
3. Free Medicare guidance from insurance brokers

Resources
Medicare: https://www.medicare.gov/
CMS: https://www.cms.gov/
KFF: https://www.kff.org/topic/medicare/
SHIP: https://www...

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In this episode, we'll walk through 7 things you must know about Medicare's annual open enrollment period.

Resources
It's Not That Complicated (pdf): https://drive.google.com/file/d/1Hqs4...
Medicare & You 2026 (pdf): https://www.medicare.gov/publications...
2025 Medicare Parts A & B Premiums and Deductibles: https://www.cms.gov/newsroom/fact-she...
Medicare Part A Costs: https://www....

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In this episode, we'll walk through the key differences and pros and cons of Original Medicare vs Medicare Advantage plans.

Resources
It's Not That Complicated (pdf): https://drive.google.com/file/d/1Hqs4...
Medicare & You 2026 (pdf): https://www.medicare.gov/publications...
2025 Medicare Parts A & B Premiums and Deductibles: https://www.cms.gov/newsroom/fact-she...
Medicare Part A Costs: ...

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A viewer asked me to suggest some tools he could use to evaluate his investment portfolio and asset allocation. So in this video we looked at three of my favorite investment tools:

1. Empower: https://go.robberger.com/empower/yt-3...
2. Kubera: https://go.robberger.com/kubera/yt-3-...
3. Google Sheets: https://robberger.com/investment-trac...

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https://robberger.com/n...

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In today's Five Question Friday (FQF) video, we cover the following questions:

1. What are the best finance apps for those with a learning disability?
2. Is 3% SWR the new 4%?
3. How do you model tax-free income in Boldin?
4. In what account type should you hold cash you plan to spend in the first few years of retirement?
5. What inflation rate should you assume in retirement?

Resources

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In today's video, we discuss how Income-Related Monthly Adjustment Amount (IRMAA) payments are calculated and 8 strategies to reduce or even eliminate the payments.

Resources from the Video
Reddit Forum Post: / strategies_to_reduce_irmaa_costs_medicare 
2025 IRMAA Brackets: https://www.humana.com/medicare/medic...
IRMAA MAGI Calculation: https://secure.ssa.gov/poms.nsf/lnx/0...
SSA-44 Form: https://ww...

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August 15, 2025 29 mins

In today's Five Question Friday (FQF), we cover five great questions and one tax calculator:

1. What is the Tax Triangle? (Traditional, Roth, and taxable accounts)
2. Is the Withdrawal Amount in FICalc the same as spending?
3. When should you sell an investment that's at a loss?
4. How far into the future should we plan?
5. When and how quickly should you change asset allocation as you near retire...

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