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Do Roth conversions in early retirement increase your sequence of returns risk? Does it take decades before the cost of a Roth conversion can pay off? Are Roth conversions really nothing more than a big gamble? I'll cover these questions in today's video. Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

In today's Five Question Friday (FQF) video, we look at these five questions: 1. What are the best financial tools for retirees? 2. What happens if my HSA balance exceeds my medical receipts? 3. Do dividends count toward my annual withdrawal rate? 4. Should the way we invest change when we retire? 5. Why does Warren Buffett think cash and bonds are bad investments? Resources Budget Apps: https://robberger.com/best-budgeting-... Retirement Planners: https://robberger.com/best-retirement... Boldin: https://go.robberger.com/boldin/yt-fqf ProjectionLab: https://go.robberger.com/projectionla... Empower: https://go.robberger.com/empower/yt-fqf Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

After recording this video, the S&P Dow Jones decided not to change its rules related to Megacap companies. As a result, SpaceX must wait at least a year to join the S&P 500 index, and maybe longer thanks to profitability requirement: https://www.youtube.com/live/PUhK1c0MSVQ Resources: CRSP Total US Market: https://www.crsp.org/crsp-market-inde... Nasdaq-100: https://indexes.nasdaqomx.com/docs/20... S&P 500: https://www.spglobal.com/spdji/en/doc... SpaceX Form S/1: https://www.sec.gov/Archives/edgar/da... Morningstar Article: https://www.morningstar.com/stocks/ho... Investment News Article: https://www.investmentnews.com/practi... **Elon Musk is preparing to take SpaceX public around June 12th**, and many investors are worried about how this massive IPO will impact their index funds. In this video, we break down exactly when SpaceX will enter major indexes, how index rules have recently changed, and whether you need to adjust your investment strategy. Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

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In today's episode,  we learn about one viewer's experience with an advisor and cover 9 topics to find out if the advice was good or bad. Resources From Video https://www.annuity.org/annuities/ann... https://opensocialsecurity.com/ Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

This week on Five Question Friday (FQF): Question 1: Has AI fundamentally changed the stock market, and does market history still matter? Question 2: If you retire a few years before claiming Social Security, how does the 4% rule apply during that gap? Question 3: If you roll a long-held Roth 401(k) into a brand-new Roth IRA, do you still have to wait five years to withdraw earnings? Question 4: Can you use traditional IRA funds to pay for long-term care and deduct the cost? Question 5: Can you build a fixed 50/50 portfolio by splitting money between Vanguard's 40/60 and 60/40 LifeStrategy funds? Resources mentioned in the episode: Schwab on the Roth 5-year rules: https://www.schwab.com/learn/story/wh... IRS Publication 502 (Medical and Dental Expenses): https://www.irs.gov/publications/p502 Vanguard LifeStrategy Funds: https://investor.vanguard.com/investm... Boldin (retirement planner): https://go.robberger.com/boldin/yt-fq... ProjectionLab: https://go.robberger.com/projectionla... Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

Cash has outperformed bonds for more than a decade. This outperformance has caused many to wonder if they should give up on bonds and put all of their fixed income into cash. In this episode, we'll look back over the past 100 years to see when cash has outperformed bonds, and when bonds have outperformed cash. Then will apply this to a 60/40 portfolio to see what we should be doing today in 2026. Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

Can a few straightforward tax moves actually improve your retirement plan? In this episode, I take one retirement plan and optimize it, then put the optimized plan next to the base plan so you can see exactly what changed and by how much. ProjectionLab: https://go.robberger.com/projectionla... Newsletter subscribes can get a promo code for 10% off. Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

Scammers are sending emails pretending to be me. In this episode, I explain several fake Rob Berger email addresses listeners have reported, along with examples of the messages being sent. Some of them start with a friendly note about a YouTube comment. Some pitch questionable investment opportunities. Some try to move the conversation to WhatsApp or Telegram. One even claims a 10% weekly return. My only real email address is: [email protected] If you receive an unexpected email from another address claiming to be me, it is not me. I will not track down your email from a YouTube comment. I will not send you an unsolicited investment opportunity. I will not ask you to move a conversation to WhatsApp, Telegram, the phone, or any other messaging app. The purpose of this video is simple: be careful, check the sender, and do not reply to these messages. If you receive one from a Gmail account, you can report it to Google. I included the reporting link below. Resources mentioned in the video: Gmail abuse report form: https://support.google.com/mail/conta... Gmail phishing help: https://support.google.com/mail/answe... Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

Sam and his wife are two years from early retirement, sitting almost entirely in cash because they think the market is too overvalued to buy. Here's why waiting for the obvious crash is harder than it looks, and a no-forecasting plan to get from all-cash to a portfolio you can actually hold. Resources in Video Boldin: https://go.robberger.com/boldin/yt-ma... ProjectionLab: https://go.robberger.com/projectionla... Note: if you subscribe to my free newsletter (link below), be sure to use the 10% discount code for ProjectionLab Shiller CAPE ratio: https://www.multpl.com/shiller-pe SGOV (iShares 0-3 Month Treasury ETF): https://www.ishares.com/us/products/3... Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

Are individual bonds safer than bond funds? After my last video on cash versus bonds, a lot of you pushed back with the same argument: with an individual bond or a bond ladder you can hold to maturity and get your money back, and a bond fund can't do that. In this video I put that idea to the test with real numbers. I start with the one thing we have to understand first, the difference between a bond's maturity and its duration. Duration is what tells us how much a bond or a bond fund moves when interest rates change. Then I look at how the funds actually did. Vanguard's Total Bond Market (BND) and an iShares 7-10 year Treasury ETF both got hit hard in 2022. Next we look at a single 10-year Treasury from the start of 2022, the kind you can hold to maturity, and track what really happened to it once you factor in inflation. Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

This week on Five Question Friday (FQF): Question 1: Is Fidelity or Vanguard the better place to keep your cash? Question 2: Is a 1.25% AUM fee reasonable? Question 3: What's the best way to preserve capital once you're in your 70s? Question 4: Should your cash bucket be a fixed dollar amount or a percentage of your portfolio? Question 5: Is it safe to share your personal finances with AI? Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

Resources in Episode Morningstar: https://go.robberger.com/morningstar/... Fidelity Article: https://www.fidelity.com/viewpoints/r... Kitces Article: https://www.kitces.com/blog/retiremen... Spend Safely in Retirement Article: https://robberger.com/spend-safely-in... Fidelity HSA App: https://apps.apple.com/us/app/fidelit... Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

This week in Five Question Friday (FQF): mega IPOs, sequence of returns risk, RMDs from a bonds-only IRA, Roth conversions after 59 1/2, and VT versus VTI plus VXUS. Question 1: Will the giant IPOs coming in 2026 drain money from the market and depress stock prices? Question 2: Is 20% to 30% in bonds enough protection against sequence of returns risk? Question 3: If you move your IRA entirely into bonds, will RMDs force you to sell bonds when they're down? Question 4: If you're over 59 1/2, why not make every IRA withdrawal a Roth conversion? Question 5: Is "VT and chill" costing you 0.7% a year compared to holding VTI and VXUS separately? Resources mentioned in the video: SpaceX IPO pricing: https://www.npr.org/2026/06/11/nx-s1-... S&P 500 buyback data: https://www.spglobal.com/spdji/en/cor... Money market fund assets: https://www.ici.org/research/stats/mmf Bengen's original 1994 paper: https://www.financialplanningassociat... Kitces/Pfau rising equity glidepath: https://www.kitces.com/blog/should-eq... IRS RMD FAQs: https://www.irs.gov/retirement-plans/... IRS Publication 590-B (Roth and IRA distribution rules): https://www.irs.gov/publications/p590b RMDs come out before conversions: https://irahelp.com/new-rule-all-ira-... The two Roth 5-year rules: https://www.kitces.com/blog/understan... The VT vs VTI/VXUS articles in question: https://princetonasset.com/2026/05/25... Elm Wealth on VT vs VTI/VXUS: https://elmwealth.com/vt-vs-vti-vxus/ Bernstein on the rebalancing bonus: https://www.efficientfrontier.com/ef/... Foreign tax credit basics: https://www.bogleheads.org/wiki/Forei... Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...

In today's video we discuss if we should try to find investments that consistently beat the S&P 500. Resources From Video    • You Can’t Win With Money While Your Life I...  https://www.spglobal.com/spdji/en/res... https://www.morningstar.com/funds/xna... https://www.morningstar.com/funds/xna... https://www.morningstar.com/etfs/arcx... Join the Newsletter. It's Free: https://robberger.com/newsletter/?utm...