The Capitalist Investor - Episode 91

Diamond Hands D and Tony The Tiger discuss several questions that both retirees and non-retirees get wrong when thinking about taxes. Derek and Tony further discuss what tax changes could be coming and what it means for everyone’s retirement, and what we can do now to prepare.

Outline of This Episode

[3:50] When you retire, will your taxes be higher or lower than when you were working? Should I be putting all my money into a Roth IRA because it isn’t taxable?

[7:20] Are my Social Security benefits taxable?

[11:04] Can you contribute to an IRA after you retire?

[12:10] Are withdrawals from IRA tax-free once you are retired?

[13:15] Are post-retirement rollovers from a 401(k) plan to a traditional IRA tax-free?

[14:56] Is the income you receive from an annuity you own taxable?

[15:50] At what age must holders of traditional IRAs and 401(k)s start taking required minimum distributions (RMDs)?

[18:35] Are RMDs calculated the same way for distributions from multiple IRAs and multiple 401(k) plans?

[19:56] Do you have to take your first RMD by December 31 of the year you turn 72?

[21:17] If your spouse dies and you get a big life insurance payout, will you have to pay tax on the money?

[21:43] How valuable must an individual’s estate be at death to be hit by federal estate taxes in 2021?

[23:00] If you’re over 65, can you take a higher standard deduction than other folks are allowed?

[24:00] BONUS: Should you pay off your mortgage before you retire?

Connect with Derek Gabrielsen

Connect With Mark Tepper

Send your questions and comments to us at

Subscribe to The Capitalist Investor

Keep Listening to The Capitalist Investor:
Episode 15:
Spending Strategies in a Bear Market, Ep #15
Episode 31:
Handicapping the 2020 Election, Ep #31
Episode 47:
11 Investments in Your Home That Pay Off, Ep #47
Episode 63:
Jeff Bezos and Amazon: Past, Present, and Future Ep #63
Episode 79:
7 Ways Biden Plans to Tax American Families (Part II), Ep #79
Episode 95:
5 Beaten Down Stocks to Buy on the Dip, Ep #95
Episode 111:
Special Episode – Talking Energy with Daniel Turner, Ep. #111
Episode 127:
Retail Earnings Tank & What The Heck is Greenflation? Ep. #127