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.
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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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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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...
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....
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: ...
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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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
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...
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...
A viewer recently asked about bracket filling:
"I haven't heard you or other financial advisors say much about "bracket filling" in retirement. Is it reasonable to think that in retirement I should be filling a tax bracket up with pre-tax accounts, then using after-tax accounts for withdrawals that reach into the higher bracket? Is there a way to model this in Bolden?"
It's a great qu...
The passage of the One Big Beautiful Bill Act has brought us a number of changes to the tax laws. Some changes are "permanent," meaning it would take an act of Congress and the President to change them. Some are "temporary," meaning they expire at some point in the future. Almost all of them can affect how we plan for retirement, particularly when it comes to Roth conversion strategies, tax-gain harvesting, and ...
Here are the five questions we cover this week in Five Question Friday:
1. Should we park cash in a money market fund or a t-bill ETF?
2. Are Robo-Advisor Tax-Loss harvesting features worth it?
3. What is the Retirement Spending Smile?
4. What rate of return assumption should you use in retirement planning software?
5. Which IRA account types can be combined?
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In today's Five Question Friday we look at the following questions:
1. How should the $6,000 senior deduction affect Roth conversions?
2. Are short-term bonds a reasonable alternative to intermediate-term bonds?
3. Are tax-managed balanced funds ok in a taxable account?
4. How should I invest money I'll use to pay the rent in retirement?
5. Boldin vs ProjectionLab for Roth conversion analysis?Join...
One of the challenges of the 4% Rule is what your initial safe withdrawal rate should be. While the name of the rule suggests one should start with 4%, there are countless reasons why that start point may not be right for you. For example, you may retiree early, you may not use the same asset allocation the rule was based on, you may have concerns about future stock market returns, inflation or both.
Enter withdrawal strat...
In today's Five Question Friday (FQF), we look at the following questions:
1. TIPS Funds vs Individual TIPS--which provides the better inflation protection?
2. Is a 4% withdrawal each year with no inflation adjustment a reasonable withdrawal strategy?
3. Can tax loss harvesting reduce IRMAA payments?
4. How can you estimate the annual income of an investment portfolio?
5. How do I track my net worth?
We look at the following questions in today's Five Question Friday:
1. Are growth stocks best for Roth IRAs?
2. How should you pay taxes on retirement account withdrawals?
3. How should you invest in retirement if you are scared of the stock market?
4. What's the ideal set-it-and-forget-it retirement portfolio?
5. Should you withdrawal cash from investment accounts to create an emergency fund?
In today's Five Question Friday video we cover these questions:
1. Why has Bill Bengen gone from 4% to 5%?
2. Is it ok to put Social Security bridge money in a money market fund?
3. How do Fidelity's Zero Funds compare to Vanguard Index Funds?
4. Should cash count towards your asset allocation?
5. Should you convert Vanguard Mutual Funds to ETFs?
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I viewer named Eileen asked about how her children, who are in their twenties, should invest. Here's her question: Can you do a video on constructing a retirement account (Roth) for my 20 year old kids? They are contributing 15%. I am thinking 10% VGSLX, 10% VSIAX, 30% VTIAX and 50% either VTSAX or VVIAX. Your thoughts please.
In this video I'll walk through the 3 goals of long-term investing, evaluate Eileen&apo...
In today's Five Question Friday we look at these 5 questions:
1. Does a Market Crash Change How to Use the 4% Rule?
2. How do bond ETFs generate returns?
3. Are Timothy Funds a good option?
4. Is Fidelity HSA a solid account?
5. What's better in retirement, Schwab Intelligent Portfolios or a TDR Fund?
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In this video, I share my experience attending a free dinner investment seminar. The seminar was allegedly to help investors handle volatility in the markets. Instead, it turned out to be a sales pitch for expensive, complex investing products like a leveraged options strategy.
Here are links to the resources I mention in the video:
SPIVA Report: https://www.spglobal.com/spdji/en/res...
Concentration of SP500:...
It’s 1996 in rural North Carolina, and an oddball crew makes history when they pull off America’s third largest cash heist. But it’s all downhill from there. Join host Johnny Knoxville as he unspools a wild and woolly tale about a group of regular ‘ol folks who risked it all for a chance at a better life. CrimeLess: Hillbilly Heist answers the question: what would you do with 17.3 million dollars? The answer includes diamond rings, mansions, velvet Elvis paintings, plus a run for the border, murder-for-hire-plots, and FBI busts.
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.
The official podcast of comedian Joe Rogan.