Advertise on podcast: The Retirement Ready Show
Rating
5from
This podcast has
250 episodes
Language
EnglishExplicit
No
Date created
2018/11/28
Latest episode
2026/10/05
Average duration
40 min.
Release period
13 days
Description
Can you afford to retire — and will your money last as long as you do? Every week, CERTIFIED FINANCIAL PLANNER™ Tony Drake and the advisors at Drake & Associates answer the questions that decide your retirement: when to claim Social Security, how to pay less tax in retirement, whether a Roth conversion makes sense this year, how to turn savings into income that lasts, and how to protect what you've built with estate planning done right. Practical, plain-English retirement planning from the team behind Milwaukee's Retirement Ready radio show, heard Saturdays and Sundays on WTMJ. New episodes weekly. Want to see if we're the right fit? Schedule a complimentary 15 minute phone call here: go.oncehub.com/scheduleacomplimentaryconsultation Investment advisory services provided by Drake and Associates, LLC and SEC Registered Investment Advisor. Insurance products are offered through a separate company, Loft Financial Advisory Group, LLC. Wisconsin Insurance Agency clients are under no obligation to purchase any recommended insurance products. The information provided is for illustrative purposes only and does not constitute investment, tax, or legal advice. While we believe the information in the show is reliable, we cannot guarantee its accuracy. Neither Drake and Associates or Loft financial Advisory group accepts any liability for the use of the information discussed. Opinions expressed are subject to change without notice and are not intended as investment advice or a solicitation for the purchase or sale of any security. Please consult your financial professional before making any investment decision.
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Podcast episodes
Check latest episodes from The Retirement Ready Show podcast
Ep.213 - Leaving a Legacy, Not a Headache
2026/10/05
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away
at RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.212 - Managing Debt in Retirement
2026/09/26
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at
RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.211 - Building a Partnership to Help Secure Your Financial Future
2026/09/19
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at
RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.210 - Building the Income Your Retirement Demands
2026/09/12
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at
RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.209 - Retirement Mistakes That Could Cost You More Than a Market Crash
2026/08/29
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at
RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.208 - 7 Tough Financial Truths Every Soon-to-Be Retiree Needs to Hear
2026/08/22
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at
RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.207 - New Fed Leadership: What Rate Changes Mean for Retirement Income
2026/08/15
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at
RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.206 - When Should You Claim Social Security? Solving the Timing Puzzle
2026/08/03
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at
RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.205 - Will I Outlive My Retirement Savings
2026/07/25
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at
RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.204 - The Roth Conversion Window: Why Your Early Retirement Years Matter Most
2026/07/24
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.203 - Inflation: A Potential Time Bomb
2026/06/13
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.202 - Don't Wait and See
2026/05/16
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.201 - Your Retirement Marathon Not Outliving Your Money
2026/05/02
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.200 - Helping Secure Womens Financial Futures
2026/04/25
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Ep.199 - The Retirement Balancing Act
2026/04/11
Each week on the Retirement Ready Show, certified financial planner Tony Drake and guests break down the most important topics in retirement planning—helping you create a roadmap for confidence and security in your golden years. From tax reduction strategies and Roth conversions to charitable giving and investment planning, our episodes bring you up-to-date insights on changing laws, smart year-end moves, and holistic approaches to managing your wealth. Whether you’re near retirement or already enjoying it, tune in for practical advice, recent updates, and tips for making the most of your savings—including how new tax rules could affect you and how to take advantage of unique opportunities. Educational workshops, resources, and friendly guidance are just a click away at RetirementReadyShow.com.
The Retirement Ready Show with Tony Drake, CFP® — Social Security, taxes, Roth conversions, and retirement income, every week from Drake & Associates. Saturdays 12pm & Sundays 7am on WTMJ 620 AM / 103.3 FM Milwaukee. Talk with us: go.oncehub.com/scheduleacomplimentaryconsultation. If the show has helped you, leave a rating on Apple Podcasts or Spotify — it's how new listeners find us.
Podcast reviews
Read The Retirement Ready Show podcast reviews
dseebrown 2019/02/11
Working towards my retirement
Tony and Brad present great information that is broken down in an easy to understand format. I’m able to walk away with great takeaways from each epis...
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