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.
8/27/26: Should you dump the corporate grind for the freedom of a side hustle, or is that itch better left unscratched? In today's episode, Jill, Mark, and special guest host Kayla Sabbagh dig into the rise of the gig economy, and maybe even make the case for corporate America.
Plus, they chat with Ben, founder of Ready Golf Club, to talk about how he's built a business on the side without blowing up his day job.
8/25/26: It’s a career advice episode!
Jill and Mark tackle the big questions: Should you follow a great mentor or stay for a bigger paycheck? When does switching fields make sense? And is owning your own business really better than being an employee?
Plus: Jill weighs in on appropriate office attire (spoiler: no shorts for men) and Mark wonders whether his wife is spending too much money on accessories.
8/20/26: Is the wealth gap really closing in America? Jill and Mark dig into new data suggesting the divide between higher and lower-income Americans may be narrowing.
Then, they respond to commenters who took issue with their takedown of Jeremy Grantham’s warning to ditch U.S. stocks and revisit Jill’s experience predicting the dot-com bubble before it burst.
Plus: TikTok’s viral “recession indicators” might be a joke, but what should you actually do to prepare for an economic downturn?
8/18/26: Jill and Mark reflect on their teenage summer jobs as teen employment hits its lowest level since the summer of 1948. What will become of American adolescence without those formative experiences scooping ice cream and lifeguarding?
Then, Katelyn asks how her college-bound oldest son can begin investing.
Plus: Jill and Mark explore the delicate dynamics of loaning money to friends and how a financial favor can change a relationship.
8/13/26: Jill and Mark discuss the rise of “helicopter parenting” in the workplace, why mom and dad need to back off.
Then, they help Marie, a caller with a newborn and a toddler, figure out how to start saving for college. They dig into whether Trump Accounts or 529s make more sense, and how to keep things fair between her children.
Plus: Are young people really spending too much money on McDonald’s?
8/11/26: Belle Burden’s bestselling memoir, Strangers, was framed as a cautionary tale about women left financially vulnerable after divorce, but it omitted a crucial detail: her substantial family wealth.
Jill and Mark explore why full financial transparency matters, what couples should understand before signing a prenup, and how to approach essential money conversations before marriage.
Plus: they help caller Megan navigate a disagreement with her husband about whether the pair can afford a bigger home.
8/6/26: Jill and Mark discuss the spectacular collapse of the Situational Awareness hedge fund and what it reveals about today's AI-fueled investing boom.
They help a caller fighting back tears figure out how to balance three competing priorities: saving for retirement, paying for her children's college, and preparing to care for her mother following the diagnosis of a degenerative illness.
Plus: a reaction to billionaire Jeremy Grantham's outrageous advice that investors should ditch U.S. stocks altogether.
8/4/26: A growing number of young Americans no longer believe that ambition and hard work lead to success.
Jill Schlesinger, Mark Talercio, and special guest host Kayla Sabbagh of Greenspring Advisors explain why that mindset can become a self-fulfilling prophecy and why believing you have agency over your future is essential to both your financial success and your mental health.
Plus: they respond to a fiery YouTube comment about inheritance, family expectations, and leaving your money to charity.