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.
7/30/26: Most Gen Z and millennials say the cost of raising a child feels financially out of reach and many don't believe they can start a family within the next five years.
Jill offers a reality check: if you want kids, don't let fear stop you. Joined by special guest host Kayla Sabbagh of Greenspring Advisors, Jill and Mark explain why raising kids in this economy is more achievable than you think.
Plus: 23-year-old Brianna, who still lives with her parents, calls in for guidance.
7/28/26: A 29-year-old who's been out of work for four years says he no longer believes in the American dream, or the stock market. Jill and Mark offer a reality check, a pep talk, and practical advice for getting back on track.
Plus: Jill and Mark dismantle the advice of "small business acquisition specialist" BenKellyOne, who instructs his followers to borrow money to buy an accounting firm without a CPA license as a way to generate extra income.
7/23/26: Jill and Mark discuss a $50 million Ponzi scheme that ensnared dozens of investors with promises of big, risk-free returns. Then, they break down the emotional manipulation tactics scammers use to gain your trust and how to protect yourself as AI makes fraud more sophisticated and hard to spot than ever.
Plus: A burned-out caller is desperate for a career reset and wonders how long she can afford to coast on her savings before figuring out her next move.
7/21/26: Dating has become another casualty of inflation. A new study finds Millennials spend an average of $252 per date and Gen Z spends $205. Meanwhile, half of singles say they’re going on fewer dates or choosing cheaper activities.
Plus: A 30-year-old single woman is daunted by the exorbitant cost of freezing her eggs, and TikTok investor Raoul Pal dismisses the S&P 500’s 11% average annual return in favor of investing in Bitcoin.
7/16/26: Half of American adults under 30 are now living with their parents. Is this the new normal, or just a temporary consequence of today’s housing market? Regardless, Jill advises young adults living at home to at least offer to chip in financially.
Plus: Mark explains why obsessing over minimizing taxes can lead to costly investing mistakes, and Jill shares her thoughts on how friends with different income levels should approach splitting the cost of dinners, vacations, and group outings.
7/14/26: Cassandra and her husband made headlines after leaving New York City to buy a home in rural Italy for just $13,000. She breaks down what motivated the move, how she’s adjusted to life in a tiny mountain town, embraced a lower-cost lifestyle, and whether trading the conventional American dream for a simpler life abroad was worth it.
Plus: Jill and Mark explain what SpaceX’s inclusion in Nasdaq index funds actually means for investors, and why one TikToker’s recommended tax loophole is complete nonsense.
7/9/26: “Dopamine sites” are on the rise in South Korea, allowing people to simulate the thrill of online shopping or food delivery without spending any actual money. Could this be the fix for compulsive spenders?
Plus: Jill helps caller Danielle navigate a financial crossroads: after taking a pay cut to make work and life more manageable, she’s now facing higher-than-expected college costs for her child while trying to stay on track for retirement.
7/7/26: Starter homes now cost a million dollars in many parts of the country, leaving younger generations wondering whether homeownership is still a realistic goal. Jill asks whether buying a house should remain a cornerstone of the American dream, or if the idea itself has become outdated.
Plus, caller questions: Dorian is feeling the financial strain of wedding season as travel costs, gifts, and pricey trips pile up. And Andrew, a brand-new dad, wants to know whether now is the right time to buy term life insurance.
7/2/26: Caller Aaron has a family mess on his hands: his cousin bought a house with a girlfriend, they broke up, and now his cousin's credit is still tied to the property while the ex continues living there and refuses to refinance. Jill explains exactly what to do before buying a major asset with someone you're not married to.
Plus: Jill breaks down the new student loan landscape effective July 1, 2026, how parents and prospective students should navigate the new rules, and why taking on debt for college may not be worth it anymore.
6/30/26: Bad news for the people hoping their parents die soon.
Americans have been anxiously awaiting the so-called "great wealth transfer," where trillions of dollars are expected to pass down from Baby Boomers to their kids, but people are living longer and holding onto their assets.
Plus, caller questions: Toby asks whether sterling silver jewelry is actually a worthwhile investment, and Dave wants to know whether taking a pay cut to improve his quality of life is financially realistic.