The Retirement Ready Show

Hosted by Tony Drake, CFP® (Drake & Associates, LLC)

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Episodes

252

Latest episode

Nov 2026

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About the show

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.

Listen to episodes

60 recent

November 7, 202638 min

Is $1 Million Enough to Retire? The Answer Might Surprise You

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.

October 31, 202635 min

Ep.215 - The Retirement Paycheck Predicament

October 5, 202638 min

Ep.213 - Leaving a Legacy, Not a Headache

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.

September 26, 202638 min

Ep.212 - Managing Debt in Retirement

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.

September 19, 202639 min

Ep.211 - Building a Partnership to Help Secure Your Financial Future

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.

September 12, 202639 min

Ep.210 - Building the Income Your Retirement Demands

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.

August 29, 202638 min

Ep.209 - Retirement Mistakes That Could Cost You More Than a Market Crash

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.

August 22, 202639 min

Ep.208 - 7 Tough Financial Truths Every Soon-to-Be Retiree Needs to Hear

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.

August 15, 202638 min

Ep.207 - New Fed Leadership: What Rate Changes Mean for Retirement Income

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.

August 3, 202639 min

Ep.206 - When Should You Claim Social Security? Solving the Timing Puzzle

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.