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Episode Archive

Oct. 4, 2025

Government Shutdown: What You Need To Know! | Retire Hour

In this episode, Joshua Cicora and team talk about the government shutdown and how that affects Social Security, Medicare, and the Stock Market. Go to RetirementHelp.com to learn more #retirement #podcast #show #money #financ...
Sept. 27, 2025

Gambling Away Your Retirement? | Retire Hour

In this episode, Matt Goolsby and team discuss safe vehicles vs stocks, Social Security benefits for survivors, and taxes on gambling. Go to RetirementHelp.com to learn more #retirement #podcast #show #money #finance #stockma...
Sept. 19, 2025

Risky Business | Retire Hour

In this episode, Matt Goolsby leads the team through a discussion on risk aversion, extra perks that come with Medicare Advantage, and the IRS going after false tax credit claims inspired by Social Media ads. Go to Retirement...
Sept. 13, 2025

A Moving Target Fund | Retire Hour

In this episode, Matt Goolsby and team discuss Japanese history, target funds, and the labyrinth that is Medicare. Go to RetirementHelp.com to learn more #retirement #podcast #show #money #finance #stockmarket #taxes #estatep...
Sept. 6, 2025

A Maximum Wage? | Retire Hour

In this episode, Matt Goolsby and team talk about tax history, maximum wages, communism, and special considerations for Large Estates. Go to RetirementHelp.com to learn more #retirement #podcast #show #money #finance #stockma...
Aug. 30, 2025

Can I Retire Yet? | Retire Hour

In this episode, Matt Goolsby and team discuss Qualified Charitable Donations, nervousness about retirement, and a new tax scam that's going around. Go to RetirementHelp.com to learn more #retirement #podcast #show #money #fi...
Aug. 23, 2025

Watch Out: IRS Scam! | Retire Hour

In this episode, Matt Goolsby and team discuss Qualified Charitable Donations, nervousness about retirement, and a new tax scam that's going around. Go to RetirementHelp.com to learn more #retirement #podcast #show #money #fi...
Aug. 16, 2025

Grief-Brain And Tax Harvesting | Retire Hour

In this episode, Matt Goolsby and team tackle the topics of the day including tax harvesting, grief-brain, rising Medicare costs, and the One Big Beautiful Bill and how it affects your taxes. Go to RetirementHelp.com to learn...
Aug. 9, 2025

Roth Confusion | Retire Hour

In this episode, Matt Goolsby and team talk about OB3, reviewing Medicare plans, and the confusion about Roth Conversions. Go to RetirementHelp.com to learn more #retirement #podcast #show #money #finance #stockmarket #taxes ...
Aug. 2, 2025

24% Cut In Social Security | Retire Hour

In this episode, Matt Goolsby and team discuss losing out on almost a quarter of Social Security, tax deductions, and dealing with your spouse's estate. Go to RetirementHelp.com to learn more #retirement #podcast #show #money...
July 19, 2025

A Million-Dollar Mistake | Retire Hour

In this episode, Matt Goolsby and team talk about OB3 bills effect on gamblers, unintended automatic enrollment into Medicare, and a Million-Dollar Mistake. Go to RetirementHelp.com to learn more #retirement #podcast #show #m...
July 12, 2025

It's Big And It's A Bill, But Is It Actually Beautiful? | Retire Hour

In this episode, Matt Goolsby and team dive into the "One Big Beautiful Bill" and look at some negatives you should be aware of. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplanning #medicare #health...
July 5, 2025

Disaster Struck | Retire Hour

In this episode, Matt Goolsby and team discuss disaster striking, last-minute estate planning, and retirement planning when you own a small business. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplann...
June 28, 2025

Taxes Are Getting Worse | Retire Hour

In this episode, Matt Goolsby and team discuss how taxes could get worse as you age, IRMAA, and mid-year tax withholdings. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplanning #medicare #healthcare B...
June 21, 2025

Estate Planning From The ICU | Retire Hour

In this episode, Matt Goolsby and team talk about long-term health risks, a 94-year old woman and her daughter, as well as estate planning from the ICU. #retirement #podcast #show #money #finance #stockmarket #taxes #estatepl...
June 14, 2025

A Sad Widow's Story | Retire Hour

In this episode, Matt Goolsby and team discuss a sad widow story, TrOOP, and why you can't send checks into the IRS anymore. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplanning #medicare #healthcare...
June 7, 2025

Losing My Spouse | Retire Hour

In this episode, Joshua Cicora and team discuss Social Security, losing a spouse, and Tax Form 5498 that you might have gotten in the mail recently. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplanni...
May 24, 2025

Big Beautiful Bill | Retire Hour

In this episode, Matt Goolsby and team discuss forgotten risks, Cancer diagnoses, and the Big Beautiful Bill in Congress. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplanning #medicare #healthcare #t...
May 17, 2025

My Rich Uncle Died | Retire Hour

In this episode, Matt Goolsby and team talk about special opportunities for those on Medicare before age 65, retiring when you own your business, and the proverbial Rich Uncle. #retirement #podcast #show #money #finance #stoc...
May 10, 2025

Rising Prices? | Retire Hour

In this episode, Matt Goolsby and team discuss rising prices, 401K beneficiaries, and retirees worried about running out of money. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplanning #medicare #heal...
May 3, 2025

Are They Going To Get Rid Of Taxes On Social Security? | Retire Hour

In this episode, Matt Goolsby and team talk about market volatility, home office tax deductions, and protecting assets when your spouse needs nursing home care. #retirement #podcast #show #money #finance #stockmarket #taxes #...
April 26, 2025

Are Medicare Premiums Going Up? | Retire Hour

In this episode, Matt Goolsby and team discuss recession fears, RMD penalties, and Medicare Supplement premiums rising at higher than average rate. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplannin...
April 19, 2025

Are We Already In A Recession? | Retire Hour

In this episode, Matt Goolsby and team discuss the stock market swinging wildly, handwritten wills, and tax extensions. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplanning #medicare #healthcare #tar...
April 12, 2025

We're In Tariff Country Now | Retire Hour

In this episode, Joshua Cicora and team discuss Tariffs, Tariffs, Tariffs, and how they affect your retirement plans. #retirement #podcast #show #money #finance #stockmarket #taxes #estateplanning #medicare #healthcare #tarif...