

Jill on Money with Jill Schlesinger
Audacy
Host Jill Schlesinger, CFP®, tackles sometimes uncomfortable and even controversial money and investing issues, without the financial jargon, to get to the heart of what’s important for anyone to know. Jill takes listener phone calls and interviews informative and entertaining guests each week to uncover surprising insights and provide actionable information so you can make the most of your money. Have a question you want us to answer on the show? Head to Jillonmoney.com and click the "Contact Us" button.
Episodes
Mentioned books

14 snips
Jun 11, 2025 • 20min
Can I Buy That Dream Retirement Home?
The discussion kicks off with practical tips on setting financial goals and earning cash back through savvy credit card use. A listener's journey towards buying her dream retirement home unveils insights into her financial readiness amidst rising housing prices. The podcast also delves into the investment strategies of a young adult, tackling job market challenges and savings options. Listeners learn about the importance of customizing cash flow strategies and exploring retirement decisions, including transitions from traditional 401ks to Roth IRAs.

12 snips
Jun 10, 2025 • 22min
Retired With Various Streams of Income
Marie, a retired small business owner from Connecticut, dives into her journey of managing retirement income and assets. She shares how her rental properties sustain her lifestyle and discusses the potential tax implications of converting her IRAs. The conversation explores the intricacies of real estate investments, including a commercial property and a vacation rental. Marie emphasizes the importance of careful budgeting, emergency funds, and estate planning as she navigates her new financial landscape while adapting to retirement.

15 snips
Jun 9, 2025 • 15min
Life Insurance With Long-Term Care Rider
Explore the world of life insurance with a long-term care rider and its pros and cons. Hear insights on retirement income strategies from a financial-savvy couple. Delve into the complexities of long-term care insurance and understand the importance of professional advice for better asset protection. Discover potential investment strategies that suit varying financial portfolios, helping you navigate your financial landscape with confidence.

Jun 6, 2025 • 44min
How Not To Invest
Today we're joined by Barry Ritholtz, co-founder, chairman, and chief investment officer of Ritholtz Wealth Management LLC, to discuss his recently released book, How Not To Invest: The ideas, numbers, and behaviors that destroy wealth - and how to avoid them.
The goal of the book is to show you a few simple tools and models that will help you avoid the most common mistakes people make with their money.
Learn these, and you are ahead of 98% of your peers. Make fewer errors, end up with more money.
Have a money question? Email us here
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Jun 5, 2025 • 22min
A Money Reset With Pension Options
I am leaving my current employer of 24 years for a new company without a pension. Should I take the lump sum or monthly payments beginning as early as 60?
Have a money question? Email us here
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Jun 4, 2025 • 18min
To PLOP or Not to PLOP?
With a bunch of pension options on the table, which one should we choose?
Have a money question? Email us here
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Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Jun 3, 2025 • 16min
I’m Getting Tired and Want to Enjoy Life
All my work comes from word of mouth and my phone never stops ringing. I'm starting to get tired and want to enjoy life. Do I have enough money to retire?
Have a money question? Email us here
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YouTube: @jillonmoney
Instagram: @jillonmoney
Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Jun 2, 2025 • 18min
Worried About Portfolio Construction
With a ton of money tied up in the business, I'm starting to worry about the overall construction of our portfolio.
Have a money question? Email us here
Subscribe to Jill on Money LIVE
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YouTube: @jillonmoney
Instagram: @jillonmoney
Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

May 30, 2025 • 17min
39 and Want to Retire
Can we stop saving for retirement and basically let about $2,100,000 and our rental home values grow without contributing more?
Have a money question? Email us here
Subscribe to Jill on Money LIVE
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YouTube: @jillonmoney
Instagram: @jillonmoney
Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

May 29, 2025 • 22min
Retired and Have a New Mortgage
With a new mortgage in retirement, one that has a high interest rate, are we okay to pay it off in the next year or so?
Have a money question? Email us here
Subscribe to Jill on Money LIVE
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YouTube: @jillonmoney
Instagram: @jillonmoney
Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices