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Have you considered owning a small business? If so, then creating an S-Corporation might be the choice for you. Pure’s Senior Financial Advisor, Thomas Vance, CFP®, AIF®, offers insights on becoming your own boss, detailing the tax implications, deductions, and retirement benefits associated with S-Corps. FREE GUIDE | 10 Tips for Real Estate Investors Transcript […]
Are women better investors and financial planners? Today on YMYW, three different husbands want to retire, while their wives feel they need to work longer. Can Jack and Diane, Mark and Belle, and Mike and his wife hit the slopes now, or do they need to keep wearing their suits? Joe and Big Al spitball on who’s right. Plus, should Ellie take her pension in a lump sum or in monthly annuity payments? The fellas also consider a solo 401(k) contribution strategy for self-employed types from our buddy Will.
Are you self-employed and feeling confused about tax filing? Too often, small business owners invest more time and energy into building their companies, only to overlook the intricacies of filing their taxes. Discover strategies to efficiently navigate the process and maximize your savings. In this guide, you’ll learn… Selecting a Legal Entity Estimated Payments The […]
Rob and his wife in North Carolina are 51 and 44 and would like to retire in the next 3-5 years. Are they on track, and what should they consider as far as Roth conversions are concerned once the tax brackets go back up, which they’re slated to do when that provision in the Tax Cuts and Jobs Act sunsets at the end of 2025? Is Mark in West Virginia on track to retire at age 59 and a half, and do Joe and Big Al have any pointers on how he can find the love of his life? Mike and Gina in Rhode Island are optimistic about retiring early at 61 and 58, but is their optimism delusional? Jake in rural Michigan is self-employed. Can he do Roth conversions to retire at age 60 and hang with Big Al in Hawaii? But first, the fellas spitball on a retirement and real estate strategy for Grey and Elena in Massachusetts.
Are low-cost mutual funds or ETFs better investments in a tax-advantaged account? Also, more strategizing from that SECURE Act 2.0 529 plan provision, the pros and cons of selling a rental house now or holding it until you pass, and an easy-breezy self-employed retirement account that’s better than a SEP IRA. Plus, will municipal bond income bump you into a higher tax bracket? Can you avoid capital gains tax by investing less aggressively over time?
How should your financial strategy change when your income increases dramatically? We’re talking like $450K one year to a million and a quarter the next? (If you guessed Roth conversions might be in the answer you’d be correct!) Joe and Big Al also spitball strategies for when your income is too high to make Roth contributions, and can you use capital gains to contribute to Roth? Can “Alligator Joe” afford to retire early, or does he need to keep gutting it out at his current job wrestling alligators? Should Catherine contribute to her 401(k) or buy company stock before she quits her day job to start a business? The fellas also spitball retirement planning involving structured settlements, inherited assets, and ACA credits, and they discuss transferring annuities to a CD vs. deferring the interest into another annuity.
Are there any holes in a 5 year plan to retire from the Air Force, buy a house and a plane, and become a commercial pilot? Can you claim an unpaid loan to a start-up as a tax loss, do a Roth conversion, and pay no tax? Are Roth Conversions a good idea in a low-earnings year? Does it matter if you convert to Roth before or after changing custodians? What retirement savings options do independent contractors have besides the Solo 401(k)? Does it make sense to cash out a 529 college savings plan that’s losing money? Plus, Joe and Big Al spitball a real estate strategy, and they discuss a state retirement account held at an insurance company.
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How do you determine how much you need in retirement when you factor in taxes, and how does the 4% rule apply? Has one YMYW listener spitballed retirement well enough to convince his wife that they can afford a new luxury truck? Can another YMYW listener take advantage of what seems to be a big opportunity to sell company stock, pay no capital gains tax, and do Roth conversions? Can Big Al’s high school friend do a 1031 exchange to buy a rental property, make it his primary residence in 5 or 10 years, and pay no tax when selling? Is earned income from stock trading still taxable for Social Security if your LLC is in a trust? Finally, a compliment comes in, and Joe and Big Al assume it’s for them.
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Setting up your saving and investing strategies when you’re in your 30s can put you on a good path to meeting your retirement goals. Joe and Big Al revisit their financial spitballing over the last couple of years specifically for savers and investors in their 30s and even 20s, some of whom want to retire early.
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When you retire and when you actually stop working may be two different things. How can you get a raise when you’re working for a startup in retirement? Should you do Roth conversions before or after you quit working? Plus, find out what Joe and Big Al think about a 529 and series I bond gifting strategy, and using whole life insurance to transfer wealth to the kids.
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Is there a way to get out of a bad SIMPLE IRA and stash cash in a tax-free Roth account? Can an owner of a company, that’s being sold to another company, load up a Roth account with company shares before the sale, and have a big chunk of cash happily growing tax-free? (What exactly are disqualified persons and prohibited transactions?) When designating beneficiaries of an annuity in a community property state like California, does state law or the annuity owner determine the beneficiary?
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How does Social Security work for self-employed small business owners? Is there a solo 401(k) that allows after-tax contributions? How much cold, hard cash should you keep on hand? Why do advisors suggest buying a fixed indexed annuity, and how do qualified charitable distributions work? Finally, is it a good idea to pre-pay the mortgage on a real estate investment, and how do you calculate the tax on a home you inherited?
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Spitballing retirement for a police officer turning teacher, a self-employed small business owner, an early retiree with an employee stock ownership plan (ESOP) wanting to do Roth conversions and withdraw 5 or 6% in retirement, and a pension and Social Security analysis. Plus, how many months of expenses should you save in your emergency fund? Also, you may know where Ric Edelman and Dave Ramsey stand on 15 vs. 30-year mortgages and using cash vs. credit, but what does YMYW think? Kyle Stacey, CFP® fills in with Big Al Clopine while Joe Anderson is on vacation.
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Does that 5-year Roth clock start with every Roth conversion? Plus, a Social Security, Medicare, IRMAA, Roth conversion retirement spitball, a self-employed retirement savings and tax planning spitball, and Delaware Statutory Trusts, security-based loans, charitable remainder trusts, and other charitable giving strategies explained. Also, will your portfolio grow faster with the help of a financial advisor? And if you’ve got a smokin’ hot wife 8 years your junior and you want to retire on the same day at ages 70 and 62, are there other financial considerations, or are you just bragging?
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How much company stock in your investment portfolio is too risky? Can series I savings bonds act as the cash in your portfolio? In the sequence of retirement savings, would contributing to a brokerage account instead of maxing out your 401(k) or 403(b) ever make sense? How should a 20-something self-employed couple, investing monthly in Vanguard’s Total Stock Market Index Fund (VTSAX), get retirement-ready? Is it possible to pay for the construction of a new home and keep the earned income tax credit and child tax credits? Should Roth conversion funds come from an inherited IRA, 401(k), brokerage account, or Social Security?
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