11/5/26: Jillionaire Dylan is 23, lives at home, works two jobs, and has managed to save $100,000. So, what should he do with it?
Jill and Mark weigh in on whether he should buy property, invest his cash, or keep saving, and why buying real estate just for the sake of owning it might not be the smartest move.
11/3/26: Traveling with friends anytime soon? You might want to have “the money talk” before hand…
In today’s episode, Jill and Mark are breaking down the must-have conversations you should have before you plan your group travel.
Plus, callers Anna and Nick are suffering from burnout, what’s next?
10/29/26: It’s open enrollment season, gang!
If you’re anything like Producer Emma, choosing your healthcare plan and benefits might make your head spin. Good news: Jill and Mark are breaking down everything you need to know when choosing a plan.
10/27/26: How do you plan for not just one retirement, but two? In today’s episode, Jill and Mark break down the financial planning every age-gap couple needs to consider.
Plus, when should you fire your financial planner?
10/22/26: It’s time for a history lesson, gang!
Personal finance has changed a lot over 300 years of American history, but some beliefs about money and markets may be timeless. On today’s episode, Jill and Mark are breaking format for a special interview with historian and author, Joseph Moore. You won’t want to miss Joseph’s unexpected insights!
10/20/26: Could you pass the AP Personal Finance exam? In today’s episode, Jill, Mark, and special guest AJ Ayers put their financial knowledge to the test with sample exam questions to find out.
Plus, how many bank accounts do you need? Let’s break it down.
10/15/26: We’ve got a special guest today, gang!
AJ Ayers, author of Creative Money: New Financial Rules for Artists, Innovators, and Misfits, joins Jill and Mark to share practical money advice for anyone who feels the financial system wasn’t built for them.
You won’t want to miss this episode, or AJ’s book!
10/13/26: Is a $400K tuition bill really worth it for four years of partying? In today’s episode, Jill and Mark break down how to get the most value out of your college degree, and when it might not be worth the price at all.
Plus, caller Michael wants to know whether he can realistically afford the home renovation he’s been eyeing.
10/8/26: Is the American Dream getting more expensive? Or is Gen Z just more sensitive?
Everyone wants to ditch Corporate America for the “content creator” lifestyle these days, but it may not be as easy as it sounds. In today’s episode, Jill and Mark break down the pros and cons of the creator economy, and all the ups and downs that come with it.
Plus: What’s all this drama about iced coffee in job interviews? Jill and Mark have the scoop, and lots more to say about corporate etiquette.
10/6/26: Is the American Dream getting more expensive? Or is Gen Z just more sensitive?
In today’s episode, Jill and Mark break down the data to settle the generational debate once and for all: Which generation is actually better off financially? Place your bets!
Plus, a TikTok takedown featuring some financial advice from a reality TV star. You don’t see that every day.
10/1/26: In today’s episode, “CBS Mornings" co-host and former NFL player Nate Burleson joins Jill and Mark once again, this time to break down how to avoid workplace-based scams and phishing.
Plus, do you really need FIVE streams of income?!
9/29/26: Today, Jill and Mark are breaking format to sit down with "CBS Mornings" co-host and former NFL player, Nate Burleson. Nate talks about his journey from the football field to television, and the financial decisions that shaped his second act.
9/24/26: Why are Jill and Mark doing a deep-dive on Margaritaville? Well, three years have passed since Jimmy Buffett died, and his family is still fighting over a $275 million estate. In today’s episode, Jill and Mark explain why estate planning is essential, and why you don’t need to be rich to need a trust.
Plus, how did caller Sam accumulate 370k by age 30 on a 95k salary!?
9/22/26: How does Costco’s $4.99 rotisserie chicken manage to defy inflation? In today’s episode, Jill and Mark break down the economics of loss leaders, and debate whether they’re willing to serve a cheaper chicken.
Plus, caller George has reached his long-term savings goal at age 37. Can he afford a lifestyle change?
9/17/26: Artificial intelligence is on everyone’s lips these days, but what does it actually mean for your wallet? Jill and Mark are breaking down what you need to know about AI and your portfolio, including how to protect yourself from potential market turmoil.
Plus, Jill and Mark help caller Cody prepare for a major career shift.
9/15/26: Do you really need an MBA? Well, it depends. In today’s episode, Jill and Mark break down when an advanced degree is actually worth the price tag, and when it might not be.
Plus, they help caller Cory navigate a big retirement decision: Should he take the pension and give up some flexibility?
9/10/26: It’s an age-old question: Should you keep renting, or bite the bullet and buy your home? Today, Jill and Mark try to help caller Alan answer that very question, and the answer may be more complicated than you think!
Plus, is anybody hitting the town anymore? As the price of a cocktail rivals the price of your lunch, Jill makes the case for staying in.
9/8/26: You heard that right: Jill is rooting for a market crash. In today’s episode, Certified Financial Planner Kayla Sabbagh joins Jill and Mark to explain why Jill might be onto something, and how, in some cases, a market crash can be good for your wallet.
Plus, Jill and the gang help caller Jessica make a financial plan for her move across the country.
9/3/26: Caller Brittany's family business has left her and her husband financially underwater. Jill, Mark, and special guest host Kayla Sabbagh help her decide if selling their house is the fresh start she needs, or just a temporary fix.
Plus, out-of-office emails: what yours really says about you, and when the details cross the line from professional into TMI.
9/1/26: Should Botox be a line item on your budget? Special guest host and Certified Financial Planner, Kayla Sabbagh, joins Jill and Mark to discuss the rise in cosmetic procedures among young people, and how to manage your face and your finances.
Plus, can you guess the price of private school in Indiana? Jill, Mark, and Kayla counsel caller Rachel on whether or not she can afford to pay to send her kid to private preschool.