Shows / Winning at Life with Gregory Ricks
Winning at Life with Gregory Ricks
Join Gregory, CEO & Wealth Advisor of Gregory Ricks Total Wealth, as he discusses a wide range of financial topics, providing education, insights, and helpful information for your financial journey.
Whether you’re interested in retirement strategies, market trends, or general financial wellness, this show is designed to keep you in the know!
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Episodes
- Winning at Life with Gregory Ricks
Episode 1377: IRS Form 5498 and Its Importance to Roth Conversions | S1E26 Winning at Life
In this episode, Gregory explains IRS forms 5498 and 8606 and their importance when it comes to Roth conversions. The episode also discusses the 60-day…
- Winning at Life with Gregory Ricks
Episode 1376: Roth Conversion Considerations Pt. 2 | S1E25 Winning at Life
In this episode, Gregory Ricks continues his series with part 2 on Roth Conversions Considerations, emphasizing long-term tax planning, tax diversification…
- Winning at Life with Gregory Ricks
Episode 1375: Roth Conversion Considerations | S1E24 Winning at Life
In this episode, Gregory Ricks continues his series on Roth Conversions, emphasizing long-term tax planning, tax diversification, and beneficiary impacts. He…
- Winning at Life with Gregory Ricks
Episode 1374: The Fall Roth Conversion Checklist | S1E23 Winning at Life
In this episode, Gregory Ricks explains how Roth contributions and conversions can create tax-free retirement income and enable long term compounding. He goes…
- Winning at Life with Gregory Ricks
Episode 1373: Demystifying Roth Conversions: What You Need To Know | S1E22 Winning at Life
In this episode, Gregory Ricks explains what it means to move money from a traditional IRA or 401(k) into a Roth IRA, and why timing and strategy matter…
- Winning at Life with Gregory Ricks
Episode 1372: Planning for Social Security Part 2 | S1E21 Winning at Life
In this episode, Gregory Ricks continues his series on planning for Social Security, focusing on Social Security taxation, claiming strategies, spousal and…
- Winning at Life with Gregory Ricks
Episode 1371: Planning for Social Security | S1E20 Winning at Life
In this episode, Gregory Ricks presents an overview of Social Security planning, emphasizing that claiming age and strategy can materially affect lifetime…
- Winning at Life with Gregory Ricks
Episode 1370: Does Your Spouse Know What To Do When You Pass? | S1E19 Winning at Life
In this episode, Gregory discusses how surviving spouses can manage finances and estate matters after a partner's death. Gregory emphasized that both spouses…
- Winning at Life with Gregory Ricks
Episode 1369: Common Misconceptions About Annuities | S1E18 Winning at Life
In this episode, Gregory Ricks talks about how retirement planning should blend market investments with fixed annuities rather than relying on anti-annuity…
- Winning at Life with Gregory Ricks
Episode 1368: The Mid Year Financial Checklist | S1E17 Winning at Life
Gregory Ricks provides a mid-year financial checklist to help individuals and business owners assess their goals, savings, and preparedness. He outlines…
- Winning at Life with Gregory Ricks
Episode 1367: Blending Investments and Annuities | S1E16 Winning at Life
Gregory Ricks discusses a new Investopedia study regarding the benefits of blending market investments with annuities to mitigate retirement risks. Gregory…
- Winning at Life with Gregory Ricks
Episode 1366: A Deeper Dive Into Trump Accounts Pt. 2 | S1E15 Winning at Life
Are Trump accounts the right move for your child’s future or your family’s financial goals? In this episode, Gregory Ricks takes a deeper dive into Trump…
- Winning at Life with Gregory Ricks
Episode 1365: The Business of Land Acquisition | S1E14 Winning at Life
Gregory Ricks hosts the Winning at Life podcast, featuring Pat Huber from First South Farm Credit. They discuss the benefits of buying land, including…
- Winning at Life with Gregory Ricks
Episode 1364: A Deep Dive into Trump Accounts | S1E13 Winning at Life
Gregory Ricks discusses the complexities of Trump accounts, a new tax-deferred savings vehicle for children. Contributions include a one-time $1,000 seed from…
- Winning at Life with Gregory Ricks
Episode 1363: How Social Security Calculates Retirement Benefits | S1E12 Winning at Life
How Does Social Security Calculate Your Retirement Benefit? Confused about how Social Security figures out your benefits? Gregory breaks it down in simple…
- Winning at Life with Gregory Ricks
Episode 1362: The Color of Money: Why Asset Allocation Matters | S1E11 Winning at Life
In Episode 11 of the Winning at Life Podcast, Gregory Ricks explores why your investment success depends more on strategic asset allocation than trying to time…
- Winning at Life with Gregory Ricks
Episode 1361: Finance Tips For Life & Business From a CPA | S1E10 Winning at Life
In Episode 10 of Winning at Life, Gregory Ricks sits down with Jude Heath, CPA and owner at J. Heath & Co. Together, they dive into real-world finance…
- Winning at Life with Gregory Ricks
Episode 1360: The 4% Rule: Guidelines for Retirement Income | S1E9 Winning at Life
If you have questions or would like to discuss your unique financial situation, schedule your no-obligation, 15 minute consultation with Gregory Ricks Total…
- Winning at Life with Gregory Ricks
Episode 1359: Roth IRA Playbook for Tax-Free Retirement | S1E8 Winning at Life
Curious if tax-free retirement is actually possible? This week on Winning at Life, Gregory Ricks sits down with Wealth Advisor Mason Goynes to break down the…
- Winning at Life with Gregory Ricks
Episode 1358: Get the Most from Your Old 401(k) | S1E7 Winning at Life
If you have questions or would like to discuss your unique financial situation, schedule your no-obligation, 15 minute consultation with Gregory Ricks Total…
- Winning at Life with Gregory Ricks
Episode 1357: The Rubber Duck Rule and Tax Planning | S1E6 Winning at Life
Are you sure you’re asking the right questions about your retirement tax plan? On this week’s episode of Winning at Life, Gregory Ricks explores the “Rubber…
- Winning at Life with Gregory Ricks
Episode 1356: Retirement Regrets You Can AVOID | S1E5 Winning at Life
Are you ready to avoid some of the most common mistakes in retirement planning? In this episode of Winning at Life, Gregory Ricks explores the essentials of…
- Winning at Life with Gregory Ricks
Episode 1355: A Deep Dive Into Annuities | S1E4 Winning at Life
If you have questions or would like to discuss your unique financial situation, schedule your no-obligation, 15 minute consultation with Gregory Ricks Total…
- Winning at Life with Gregory Ricks
Episode 1354: Common Risks to Your Ideal Retirement | S1E3 Winning at Life
On this episode of the Winning at Life Financial Podcast, wealth advisor and CEO Gregory Ricks discusses strategies for sustainable retirement income…
- Winning at Life with Gregory Ricks
Episode 1353: Invest 50/50 Rule: Balancing Risk in a Healthy Portfolio | S1E2 Winning at Life
In this episode of Winning at Life, Gregory Ricks explains why working with a financial advisor can help you reach your goals while avoiding costly missteps…
- Winning at Life with Gregory Ricks
Episode 1352: Finding Purpose in Financial Planning | S1E1 Winning at Life Podcast
Watch the full episode on the Gregory Ricks Total Wealth YouTube Channel: https://youtu.be/zbgqW0a7q9Y In the first episode of the Winning at Life podcast…
- Winning at Life with Gregory Ricks
Episode 1351: The Weekly Wrap 03.14.26
In this episode, Gregory Ricks discusses the importance of timely financial decisions, like rollovers and IRA contributions, to avoid tax penalties. For…
- Winning at Life with Gregory Ricks
Episode 1350: The Weekly Wrap 02.28.26
In this episode, Gregory Ricks and Mortgage Gumbo's Dwayne Stein discuss mortgage rates reaching 3 year lows and what this could mean for homebuyers this…
- Winning at Life with Gregory Ricks
Episode 1349: The Weekly Wrap 02.21.26
In this episode, Gregory Ricks is joined by Wes Blanchard, of WJ Blanchard Law, to discuss the process behind estate planning and the importance of having a…
- Winning at Life with Gregory Ricks
Episode 1348: The Weekly Wrap 01.31.26
In this episode, Gregory Ricks is joined by Wes Blanchard of WJ Blanchard Law to discuss common mistakes that can ruin your estate plan and the importance of…
- Winning at Life with Gregory Ricks
Episode 1347: The Weekly Wrap 01.17.26
In this episode, Gregory Ricks is joined by Jude Heath of J. Heath and Co., CPA, to discuss tax planning for this upcoming 2026 tax season. Then, Gregory…
- Winning at Life with Gregory Ricks
Episode 1346: The Weekly Wrap 12.20.25
In this episode, Gregory Ricks is joined by Dwayne Stein, host of Mortgage Gumbo, to preview the 2026 housing market as well as potential changes coming from…
- Winning at Life with Gregory Ricks
Episode 1345: The Weekly Wrap 12.13.25
In this episode, Gregory Ricks is joined by Attorney Wes Blanchard of WJ Blanchard Law, LLC., to discuss estate litigation issues including Usufruct and Powers…
- Winning at Life with Gregory Ricks
Episode 1344: The Weekly Wrap 11.15.25
In this episode, Gregory Ricks is joined by Dwayne Stein, host of Mortgage Gumbo, to discuss why waiting to buy a home could end up costing you more and what a…
- Winning at Life with Gregory Ricks
Episode 1343: The Weekly Wrap 11.1.25
In this episode, Gregory Ricks is joined by Wes Blanchard of WJ Blanchard Law, LLC, to discuss the importance of estate planning, emphasizing the need for…
- Winning at Life with Gregory Ricks
Episode 1342: The Weekly Wrap 10.25.25
This episode features Gregory Ricks and Dwayne Stein of Mortgage Gumbo discussing new opportunities within the housing market. Then Jude Heath of J. Heath and…
- Winning at Life with Gregory Ricks
Episode 1341: The Weekly Wrap 10.11.25
This episode, Gregory Ricks discusses the financial and economic impacts of the recent government shutdown. He also emphasizes the importance of long term…
- Winning at Life with Gregory Ricks
Episode 1340: The Weekly Wrap 09.20.25
This episode, Gregory Ricks explains how spousal and survivor benefits can impact your Social Security as well as tax efficient ways to sell your business or…
- Winning at Life with Gregory Ricks
Episode 1339: The Weekly Wrap 09.27.25
This episode features Gregory Ricks and Dwayne Stein, host of 'Mortgage Gumbo', discussing how to build wealth through Real Estate. Jude Heath, CPA with J…
- Winning at Life with Gregory Ricks
Episode 1336: The Weekly Wrap 07.12.2025
Dwayne Stein from Mortgage Gumbo joined the show to discuss a 40% year-over-year jump in mortgage applications, steady interest rates, and the potential impact…
- Winning at Life with Gregory Ricks
Episode 1335: The Weekly Wrap 06.28.25
In this episode of "Winning at Life," Gregory Ricks discusses the critical importance of proactive estate planning with Wes Blanchard, highlighting how…
- Winning at Life with Gregory Ricks
Episode 1334: The Weekly Wrap 06.14.25
On this week's episode of Winning at Life, Gregory Ricks and Dwayne Stein cover rising mortgage rates, real estate pitfalls, and how global tensions may…
- Winning at Life with Gregory Ricks
Episode 1333: 06.07.25 Weekly Wrap - 15th Anniversary Episode!
In this special 15th anniversary episode of Winning at Life with Gregory Ricks, Gregory reflects on the journey of building a financial radio show and firm…
- Winning at Life with Gregory Ricks
Episode 1332: The Weekly Wrap 05.31.25
In this week’s episode, Gregory Ricks dives into the unexpected risks of not having your estate planning in place—with expert insight from estate planning…
- Winning at Life with Gregory Ricks
Episode 1331: The Weekly Wrap 05.17.2025
In this week's episode of Winning at Life, Gregory Ricks is joined by CPA Jude Heath for a deep dive into smart tax planning strategies for 2025 and beyond…
- Winning at Life with Gregory Ricks
Episode 1330: The Weekly Wrap 05.10.25
Winning at Life with Gregory Ricks | The Weekly Wrap 05.10.25 He’s back! Gregory Ricks has returned to Winning at Life after a brief break—refreshed and ready…
- Winning at Life with Gregory Ricks
Episode 1329: The Weekly Wrap 03.29.25
In this comprehensive episode of "Winning at Life® with Gregory Ricks," host Gregory Ricks tackles a wide range of critical financial topics, from the latest…
- Winning at Life with Gregory Ricks
Episode 1328: The Weekly Wrap 03.22.25
In this episode, Gregory covers Investment strategies and diversification, Medicare, Tax implications of Social Security benefits, and Strategies for managing…
- Winning at Life with Gregory Ricks
Episode 1326: The Weekly Wrap Replay 03.08.25
In this episode of Winning at Life® with Gregory Ricks, Gregory discusses government spending, concerns about national debt, the need to reduce deficit…
- Winning at Life with Gregory Ricks
Episode 1325: The Weekly Wrap 2.8.25
In this episode of Winning at Life® with Gregory Ricks, Gregory is joined by Jude Heath, CPA, and Janae Bridges, Wealth Advisor at Gregory Ricks & Associates…
- Winning at Life with Gregory Ricks
Episode 1324: The Weekly Wrap 2.1.25
In this episode of Winning at Life®, host Gregory Ricks dives into the latest updates on the Social Security Fairness Act and how it will impact retirees. He's…
- Winning at Life with Gregory Ricks
Episode 1323: The Weekly Wrap 1.11.25
Tax Season Strategies, Social Security Changes, and Retirement Planning Insights! In this jam-packed episode, host Gregory Ricks welcomes Jude Heath, a CPA…
- Winning at Life with Gregory Ricks
Episode 1321: The Weekly Wrap 12.21.24
In this comprehensive episode of "Winning at Life® with Gregory Ricks," host Gregory Ricks tackles a wide range of critical financial topics, from the latest…
- Winning at Life with Gregory Ricks
Episode 1320: The Weekly Wrap 12.7.24
Gregory Ricks and Jude Heath discussed financial planning and tax preparation strategies. They emphasized the importance of proactive tax planning, especially…
- Winning at Life with Gregory Ricks
Episode 1319: The Weekly Wrap 11.23.24
Gregory Ricks and Wes Blanchard discusses the importance of estate planning, emphasizing the need for wills and powers of attorney. They highlight the risks of…
- Winning at Life with Gregory Ricks
Episode 1317: The Weekly Wrap 11.9.24
Gregory Ricks and Jude Heath discussed the future of taxes, focusing on the potential impact of the new administration. They highlighted the importance of tax…
- Winning at Life with Gregory Ricks
Episode 1316: The Weekly Wrap 11.2.24
On this week's episode of Winning at Life with Gregory Ricks, Gregory discusses the upcoming time change, emphasizing the importance of being proactive with…
- Winning at Life with Gregory Ricks
Episode 1315: The Weekly Wrap 10.26.24
Gregory Ricks and Dwayne Stein discuss the current state of the mortgage market, emphasizing the importance of understanding the difference between federal…
- Winning at Life with Gregory Ricks
Episode 1314: The Weekly Wrap 10.12.24
Gregory Ricks and his guest Wes Blanchard discuss various financial and estate planning topics on this weeks episode of Winning at Life with Gregory Ricks…
- Winning at Life with Gregory Ricks
Episode 1313: The Weekly Wrap 10.5.24
Gregory Ricks and his guest Jude Heath, CPA discuss tax strategies and financial planning on his radio show Winning at Life with Gregory Ricks. They highlight…