
Jill on Money with Jill Schlesinger
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.
Latest episodes

Jul 4, 2025 • 27min
An American Story With Ken Langone
Ken Langone, a legendary financier and co-founder of Home Depot, shares his inspiring journey from a working-class background to becoming a business titan. He reflects on the value of education, the mentors who guided him, and the challenges of discrimination in the finance industry. Langone discusses the revolutionary inception of Home Depot and its impact on the market. He also dives into the complexities of capitalism and income inequality, emphasizing how upward mobility is attainable through hard work and smart decisions.

4 snips
Jul 3, 2025 • 20min
I Don’t Want to Work Until I’m 70!
As retirement approaches, listeners ponder the feasibility of leaving work at 65. The discussion dives into the impact of social media on financial independence and exploring inclusive financial conversations. A listener shares plans to relocate to California, prompting a look at housing costs and health considerations in retirement. Strategies for balancing health and finances are shared, emphasizing the importance of assessing financial stability and planning for future expenses. The hosts encourage proactive financial mapping and seeking assistance.

5 snips
Jul 2, 2025 • 15min
Any Benefit to Actively Managed 401(k)?
Listeners learn about the pros and cons of actively managed 401(k) plans and the potential returns they promise. The hosts dissect a financial advisor's claims and explore the hidden costs of management fees. Strategies for maximizing Social Security benefits and retirement planning are also discussed, including the advantages of delaying claims and considering Roth conversions. Additionally, valuable insights are shared on supporting family during transitions, emphasizing the importance of legal advice in financial decisions.

7 snips
Jul 1, 2025 • 23min
Are We Okay to Build a New House?
Listeners explore the highs and lows of building a new home, including the rising costs that often surprise homeowners. A couple navigates their finances while considering family needs and educational commitments. A retired teacher shares their transition to real estate, gaining valuable insights for financial planning. Discussions on construction loans, savings strategies, and the emotional rollercoaster of home financing are intertwined with lighthearted local traditions, making the serious topic more relatable.

13 snips
Jun 30, 2025 • 15min
Possible Early Retirement Readiness
The podcast dives into the critical topic of early retirement, particularly for federal employees. Listeners hear valuable insights on financial planning, especially for someone at 54, and how personal circumstances impact retirement decisions. There’s an exploration of key assets like thrift savings plans and the advantages of inherited IRAs post-legislation changes. The conversation highlights pension benefits and the essential strategies for achieving desired income levels. Early financial planning and the value of consulting a fee-only advisor are also emphasized.

13 snips
Jun 27, 2025 • 21min
Is the Annuity Too Good to Be True?
This discussion dives into the allure of annuities as a means to generate guaranteed income during retirement. A couple shares their initial skepticism but considers expert advice while evaluating their unique financial situation. The host critiques a financial planner's proposal, exploring the potential benefits and drawbacks of annuities versus alternative investment strategies. Misconceptions about annuities are addressed, emphasizing the importance of informed financial planning and the value of getting a second opinion from a knowledgeable advisor.

10 snips
Jun 26, 2025 • 23min
Hubby Hates Job, Can He Quit?
Minnie Mouse from Pennsylvania shares her husband's struggles with job dissatisfaction. They delve into the possibility of him taking a lower-paying role while still aiming for a comfortable retirement by age 55. The conversation covers essential financial strategies, including investment options and the emotional impacts of career transitions. They also explore the pros and cons of lump sum pensions versus steady income, all while sprinkling in delightful Disney memories to lighten the discussion.

10 snips
Jun 25, 2025 • 16min
Convincing Hubby We're Okay
The emotional journey of buying a home in California highlights the crucial role of realtors for first-time buyers. Dive into the couple's contrasting views on financial security as they navigate complex retirement plans. Explore the math behind savings and the importance of having a cash cushion. The discussion also covers sustainable income strategies, social security benefits, and how aligned financial goals can strengthen relationships. Tune in for valuable insights on achieving peace of mind in your financial future!

15 snips
Jun 24, 2025 • 16min
Should I Collect Social Security Early?
This discussion tackles the dilemma of when to collect Social Security, weighing the pros and cons of early versus delayed benefits. Listeners share personal experiences that highlight financial shortfalls and concerns over means testing. The conversation also shifts to homeownership, exploring whether it's a worthwhile investment compared to renting, and delves into effective strategies for balancing savings and investments. The importance of informed decision-making in navigating retirement and housing options is emphasized throughout.

12 snips
Jun 23, 2025 • 27min
Saving for Retirement vs College Funding
This discussion tackles the delicate balance between saving for retirement and funding a child's college education. They explore strategies for boosting retirement contributions while managing family expenses, highlighting the importance of 529 plans for education funding. Humor adds levity as they navigate the complexities of financial aid and debt management. Additionally, there's a focus on effective estate planning and ensuring families are prepared for future financial changes, making the often daunting tasks of saving feel more manageable.