Afford Anything | Make Smart Money Choices
Afford Anything is a podcast about making smarter decisions with money, time, energy, and attention. Host Paula Pant explores the psychology of money and critical thinking, interviewing experts and answering listener questions. The show aims to help listeners think from first principles and make better choices in life and finance.
Episodes
Everyone Wants a Piece of You. Here's How to Stay Whole -- with Luke Burgis
#743: Everyone talks about a loneliness epidemic — but Luke Burgis argues the opposite problem is just as real: we now have so much easy, frictionless community that we never have to develop a solid sense of who we actually are.
Luke Burgis is a professor of business at The Catholic University of America and the founder of the Cluny Institute, and the bestselling author of Wanting: The Power of M
Q&A: I Reached Financial Independence Three Years Early … Now What?
#742: A listener hit her $1.4 million early-retirement goal three years ahead of schedule — and now she's stuck deciding whether paying off a low-interest mortgage is smart, or just fear in disguise. Later, a former financial planner explains why he still won't recommend one of the most talked-about "safer" investing strategies in the FIRE community.
This week's Q&A tackles three listener questio
You Can't Buy Back Your 20’s — with Jack Raines
#740: Jack Raines turned $6,000 into $400,000 trading blank-check stocks during the 2020–2021 bubble — and he says it was some of the least fun money he's ever made.
Jack Raines is a writer and investor at Slow Ventures, and the author of the new book Young Money: A Field Guide to Wealth and Purpose in Your Twenties.
In this episode, we discuss:
Why "golden handcuffs" are almost always a
Q&A: Should We Retire in Our 40s With $4 Million and an 80% Stock Portfolio?
#740: Paula and Joe rarely butt heads — but a caller's side hustle, which pulled in $5,500 in a single day, sparked their most heated disagreement in months.
This week's mailbag: a couple weighing an early retirement built on $1.2 million, a wedding-dress side hustle deciding whether to go all in, and a listener whose small stock investment turned into a $25,000 tax puzzle.
In this episode,
First Friday: We Lost 23,000 Jobs, Yet Somehow Unemployment is Down?!?!
#739: The U.S. just lost 23,000 jobs — and unemployment fell anyway. The numbers were strange enough that Paula broke a years-long, all-stocks habit and bought her first bond, ever.
In this month's First Friday economic roundup, Paula breaks down the jobs report, the bond market, mortgage rates, gold, and a new kind of account for kids.
Topics include:
How to make sense of a jobs report th
Hackers Waited 3 Months for This Couple's $1.2 Million Deal, with Dr. Eric Cole [GREATEST HITS]
#738: Hackers broke into a real estate closing company's servers and waited three months for the right deal — then intercepted a wire and stole $1.2 million from a couple who did everything right, right down to the closing table.
Dr. Eric Cole was a former CIA hacker, Cybersecurity Commissioner under President Obama, and longtime security advisor to Bill Gates. We're resharing this conversation,
She's Researched Money for 30 Years—and Never Seen It This Bad for Young People, with Beth Kobliner
#737: Beth Kobliner has covered personal finance for people in their 20s and 30s for over three decades — and she says this is the hardest she's ever seen it. One in four young people now believe that betting on gambling sites and prediction markets counts as investing.
Beth Kobliner is a personal finance journalist and New York Times bestselling author of Get a Financial Life, who served on Pres
Q&A: Would You Spend $60,000 on a Wedding Knowing It Could Be $800,000 Someday?
#736: A bride wants to spend $60,000 on her wedding — money that could grow to $800,000 in 40 years if she invested it instead. This week, three very different listener questions all boil down to the same fight: what the math says versus what actually makes you happy.
👉 Figure out your own money mindset — free FiiRE Playbook: https://affordanything.com/fiire
This week, Paula and Joe tackle three
He Tried 30+ Side Hustles Before 3 Actually Paid Off, with Cody Berman
#735: Cody Berman failed at more than 30 side hustles — from a disc golf manufacturing company to sweaty bike deliveries in the Australian heat — before three of them got him to financial independence at 25.
Cody is the bestselling author of Retire by 30, who reached financial independence at 25 by stacking income from real estate, digital products, and the stock market.
In this episode, we
Q&A: Her Brother Owns 3 Houses — Is That Why We Have a 'Housing Shortage'?
#734: Depending on which source you ask, the U.S. is short somewhere between 1.2 million and 10 million homes — and the reason for that wild range says as much about who's counting as it does about the shortage itself.
👉 Free cheat sheet: which investments belong in which account: https://affordanything.com/assetlocation
This week, Paula and Joe tackle three listener questions: whether the
The Hidden Math Behind Every Venture Capital Fund, with former Wharton Prof. David Bell
#733: Venture fund managers can collect years of fees before a single dollar comes back to investors — and the bar to hand over your money is lower than you'd think.
David Bell spent 20 years as a chaired professor at Wharton before co-founding the venture firm Idea Farm Ventures, where he's backed early-stage brands like Bonobos, Warby Parker, and Jet.com.
In this episode, we discuss:
How v
Your Zip Code Is Quietly Deciding What You Buy, with former Wharton Prof. David Bell
#732: Where you live is already deciding what you'll buy today, before you've even made up your mind. And it turns out the customers your local stores ignore completely are often a brand's most valuable ones.
David Bell spent twenty years as a Wharton marketing professor before becoming one of the earliest investors in Warby Parker, Bonobos, and Diapers.com. He's now co-founder of the consumer ve
Is AI Making You Dumber? With Lorraine Marchand
#731: What if the best way to test a new hire wasn't a resume, but a two-hour breakfast? One CEO built his entire hiring process around it — and it worked.
Lorraine Marchand spent three decades in leadership roles at companies like IBM, Bristol-Myers Squibb, and LabCorp, and interviewed more than 120 CEOs for her book on what actually makes teams innovate. Now she teaches at Wharton and Columbia
Q&A: We Have $1.5 Million. Can We Stop Now?
#730: What does it actually mean to have "enough" — and how do you know when it's time to stop optimizing and start living?
AVOIDING THE REAL ESTATE MISTAKES IN THIS FREE GUIDE COULD SAVE YOU $10,000 OR MORE 👉https://affordanything.com/mistakes
In today's episode:
Jax, a longtime listener, has hit a mindset shift — prioritizing sabbaticals and shared experiences over pure accumulation. He
First Friday: Jobs Are Cooling, Prices Are Climbing, and NYC is Freezing the Rent
#729: The U.S. added 57,000 jobs in June. Economists expected 115,000.
Meanwhile, inflation hit a three-year high. The Personal Consumption Expenditures index - the Fed's favorite inflation gauge - jumped 4.1 percent year-over-year.
That combination creates a problem. Weak jobs usually push the Fed to cut rates. Hot inflation pushes them to hike. In this First Friday episode, we break down w
Q&A: What $2.4 Million at 37 Actually Looks Like (It's Not What You Think)
#728: What do you do when you suddenly have $850,000 and no idea what to do with it?
GET TOTAL CLARITY ON WHERE EVERY DOLLAR BELONGS 👉 https://affordanything.com/cornerstone
On today’s Q&A, one caller recently inherited $850,000 from his mother. He's already wealthy, earns over $500K a year, and has a solid net worth — but he's anxious, lost, and doesn't want to make a decision he can't undo
Hope Isn't a Feeling. It’s a Skill. - with Dr. Julia Garcia
#727: Not sure what your next money move should be? Start with the free FiiRE Playbook 👉 https://affordanything.com/fiire
Dr. Julia Garcia is a psychologist, behavioral researcher, and author of The Five Habits of Hope — and she's spent years studying why smart, hardworking people stay stuck.
What if the biggest thing standing between you and your financial goals isn't your income, your de
Q&A: She Has $884K Saved — So Why Can't She Retire?
#726: Hey, we're mixing it up today with a super deep dive. We normally go fairly deep on this show, but today we're going even deeper and turning one caller's question into a case study.
Download the Four Cornerstone Worksheet to follow along: www.affordanything.com/cornerstone
An anonymous caller is reevaluating their finances after a series of health challenges, caregiving responsibilit
What Most Families Get Wrong About Passing Down Wealth, with Andrea Baumann Lustig
#725: Most people assume their financial advisor is legally required to put their interests first. That's not always true.
Andrea Baumann Lustig, a wealth advisor with 30 years of experience, joins us to walk through the blind spots she sees most often in legacy planning -- the deeply held beliefs that quietly undermine people's financial futures.
We start with something most people never th
Why Does Every Good Idea Die in a Meeting? – with HBS Prof Linda Hill and Jason Wild
#724: Linda Hill, a Harvard Business School professor, and Jason Wild, an innovation consultant who has led projects in 40 countries, join us to break down how organizations innovate.
Linda and Jason have spent decades studying companies that consistently produce breakthroughs - from Pixar to Delta Airlines to Cleveland Clinic - and they've identified three leadership roles that matter most: th
Six Levels of Wealth, with Nick Maggiulli [GREATEST HITS]
#723: This episode originally aired in July 2025.
Here's the thing about personal finance advice: what works when you have $10,000 won't work when you have $1 million.
Yet most financial guidance treats everyone the same, whether you're scraping together a $1,000 emergency fund or deciding whether to upgrade to business class.
Nick Maggiulli, author of "The Wealth Ladder," joins us to b
Q&A: Why Do I Still Feel Anxious When I’m Clearly Doing Well?
#722: Free lesson: affordanything.com/mistakes
Ask us a question: affordanything.com/voicemail
What happens when your financial plan is technically working — but emotionally, it still doesn’t feel secure?
Caitlin and her husband have their core expenses covered, but her side hustle brings in an extra $600 a month. With young kids, daycare costs, and long-term retirement goals all compet
First Friday: Fed Rate Hike Coming? Jobs & Housing News
#721: The US economy showed robust job growth in May, adding 172,000 new jobs, exceeding expectations. This suggests a broadening of economic recovery beyond essential services.
Treasury yields have climbed significantly, reflecting investor concerns about inflation.
Inflation remains a significant concern, driven largely by surging energy costs.
And there's good news emerging in prescri
Q&A: When the "Right" Decision Feels Harder Than The Math
#720: At what point does making the “right” financial decision start to feel emotionally harder than the math itself?
Rebecca: is wondering whether the Rule of 72 means she can ease up on retirement contributions—or whether continuing to max out her Roth 401(k) is still the smarter move despite multiple mortgages, car loans, and college savings goals.
Kate: feels trapped between the math and
Your Office Is Making You Sick, with Dr. John La Puma
#719: Most of us spend 93 percent of our time indoors, and it's making us sicker, more tired, and less productive than we realize.
Dr. John La Puma is a physician and researcher who studies what happens to the human body when it's indoors too much.
He joins us to explain the science behind what he calls the indoor epidemic: the chronic diseases, burnout, insomnia, and cognitive decline that ste
Q&A: The Goalposts Moved — Is That Actually a Problem?
#718: What happens when the financial strategy that once felt obvious suddenly becomes a lot more complicated?
Les is approaching financial independence but has realized there’s one thing missing from the traditional FIRE equation: how do you continue meaningful charitable giving after you stop earning a paycheck?
Jaime has built a sizable retirement portfolio, but now he’s wondering whether
The 5 Ways Investors Behave When Things Go Wrong, with Clare Flynn Levy
#717: Clare Flynn Levy was a hedge fund manager in London in the summer of 2007, watching her trading screens turn red — every single day. Merger arbitrage spreads were widening. Investors were pulling out. She didn't yet realize she was watching the early tremors of a global financial crisis.
Clare joins us to talk about what that experience taught her about investor behavior, emotional bias, an
Q&A: Your Kids Just Inherited $350,000 Each. Now What?
#716: When does a financial decision stop being purely about maximizing returns—and start becoming about building the life you actually want?
Karen recently inherited sizable trusts for their children and is now navigating the complicated intersection of investing, taxes, legacy planning, and future financial aid eligibility.
Matt has spent years building a solid index fund portfolio, but
Mrs. Dow Jones: Your Childhood Is Running Your Bank Account
#715: She grew up with a Goldman Sachs dad. She still ended up broke in her 20’s. Here's what changed.
Haley Sacks - known online as Mrs. Dow Jones - joins us to talk about the five-step financial framework she calls IBIZA.
Despite every advantage, she spent her twenties anxious, financially dependent, and charging dinners to her parents' credit card.
One birthday trip to a Toronto restaurant
Q&A: Should I Sell One Property to Pay Off Another?
#714: When you’re making big financial decisions, what matters more: optimizing for the best long-term outcome, or choosing the path that gives you the most flexibility and peace of mind right now?
Melissa retired early and now lives off rental income, but she’s considering selling one property to pay off another. The catch? Her monthly income would stay about the same—so the real question is w
BONUS: The Economy Added 115,000 Jobs. Consumer Confidence Just Hit a 74-Year Low. Let’s Unpack This.
The US economy added 115,000 jobs in April -- and the numbers look solid on the surface.
But dig a little deeper and you'll find a tech sector in freefall, a housing market frozen in place, and consumer sentiment that hit a 74-year low.
This bonus episode breaks down the May jobs report, which came out a week late because the Bureau of Labor Statistics pushed its release from the first Friday t
Why Smart People Still Sabotage Their Own Money, with Tiffany Aliche
#713: Tiffany Aliche spent her 30th birthday in her childhood bedroom, $300,000 in debt, unemployed, and freshly foreclosed on.
Sixteen years later, she's generated over $50 million in gross revenue as a business owner.
She joins us to talk about what actually happened in between.
Aliche - known as The Budgetnista - built her personal finance platform almost by accident. After a friend stole
The Rental Strategy That Survived Every City Crackdown, with Jeff Hurst
#712: Jeff Hurst, CEO of Furnished Finder, joins us to break down what midterm rentals are, who they're for, and why now might be the best time to get in.
A midterm rental is a furnished unit rented for 30 days or longer - longer than a hotel stay, shorter than a traditional lease. Cities have been regulating Airbnb-style short-term rentals out of existence, leaving a wave of furnished properties
Is a Computer Science Degree Still Worth the Debt?, with Ron Lieber
#711: A computer science degree used to feel like a sure thing. Job placement rates topped 90 percent. Starting salaries cleared $80,000. You could do the math on your student loans before you enrolled.
That math doesn't work the same way anymore.
New York Times "Your Money" columnist Ron Lieber joins us to walk through what families actually need to know before borrowing for college.
He
Q&A: He Wants to Die With Zero – Here’s How to Spend $1M Without Running Out
#710: What does it really look like to balance financial optimization with real-life tradeoffs—whether that’s choosing meaningful work, spending down your savings, or deciding where your next dollar should go?
Mike is planning to retire at 60 with $1 million saved and a clear goal: spend it all during his lifetime. He wants to know how to structure his withdrawals so he can maximize income no
The Financial Reality of Developmental Disabilities, with Keith Wargo
#709: Keith Wargo has spent decades navigating one of the most daunting financial planning challenges a family can face: raising a child with a developmental disability. He joins us to share what families need to know.
The financial stakes are significant. Keith, who is the CEO of Autism Speaks, estimates lifetime care costs for a person with a developmental disability can run between $1.4 and $2
Q&A: My Mom Is 73. She Has a House — But It Doesn’t Pay the Bills. Now What?
#708: What’s the smartest way to handle big financial transitions—when the stakes are high and the “right” answer isn’t always obvious?
Anonymous “Cyndi Jr.” is helping their 73-year-old mother relocate across the country and needs to decide how to use the proceeds from a home sale to balance long-term housing security with inflation protection.
Anonymous is trying to figure out how to handle qu
Q&A LIVE from Texas A&M Texarkana
#707: Joe and I traveled to the campus of Texas A&M University-Texarkana for a very special live recording. We were joined by Jay Davis, the Executive Director of Financial and Entrepreneurship Engagement, to answer questions from an incredible audience of students. Whether you’re just starting your career or looking to "reset" your habits, this episode covers the essential transition from the cla
Q&A: The Case for NOT Paying Off Your Student Loans
#706: When the numbers look straightforward—but the rules, timing, and future are uncertain—how do you decide what to do next?
KJ has $90,000 in student loans, a recent inheritance, and a lot of uncertainty around changing repayment policies, and is trying to decide whether to pay down debt now or hold onto cash in case future payments become unaffordable.
Anonymous (let’s call her Andr
What to Fix First When Everything Feels Stuck, with former Lyft COO and Tesla President Jon McNeill
#705: Jon McNeill, former president of Tesla and COO of Lyft, starts with a simple problem: his teenage son is about to start driving, and he’s worried about texting behind the wheel.
Instead of setting rules, he builds a solution. That idea becomes TruMotion, a company that uses smartphone sensors to track driving behavior. You hear how the app figures out whether someone is actually in the driv
Q&A: Should I Quit My Job to Be a Stay-at-Home Dad
#704: How do you make smart financial decisions when you’re balancing debt, investing, and big life changes … all at the same time?
Today, Brigham and his wife, ages 25 and 23, wonder: can they buy a $500,000 home AND still support a stay-at-home parent?
Next, JVR asks how to balance high-interest credit card debt, student loans, and a large cash reserve while planning for a future home pur
First Friday: Jobs Are Up. So Why Does the Economy Feel Worse?
#703: April’s jobs report comes in much stronger than expected, with 178,000 jobs added and unemployment ticking down to 4.3 percent. That headline deserves a closer look, especially when other labor data still points to a slower, lower-hiring environment.From there, we break down what the latest Fed decision means, why mortgage rates remain elevated, and how a sudden spike in oil and gas prices c
Q&A: Why 3 Years Is a Weird Timeline for Money
#702: Olivia is saving for a specific three-year goal and wants to know whether a money market fund is the right place to store that cash, or if a traditional savings account would be safer.
Robert is planning to retire early in the next few years and is trying to decide whether to prioritize building taxable investments or continuing to grow Roth accounts.
And finally, we’ll hear from a listene
What Retirement Planning Gets Wrong, with Jamie Hopkins
#701: Forget the idea that you need a magic number to retire.
Jamie Hopkins is a certified financial planner, professor of taxation at the American College of Financial Services, director of the New York Life Center for Retirement Income, and Top 40 Under 40 financial services professionals from InvestmentNews.
His take on retirement planning will make you rethink a few things.
We start with
Q&A: A $30K Promotion Near FI, Learning Put Options, and Scaling a 16-Unit Portfolio
#700: Today we’re tackling three different financial questions from our listeners.
First, we’ll hear from Melanie, who is deciding whether to pursue a promotion that would increase her salary by $30,000 but may add more stress, even though she’s already close to financial independence.
Next, Ami wants to learn how options trading works and is wondering how to find legitimate training without fal
Nir Eyal: The Four Questions That Can Change Any Belief
#699: You've probably heard that mindset matters. But what does that actually mean, and is there science behind it?
Nir Eyal, author of Beyond Belief, joins us to break down the research.
Eyal, who writes about the intersection between psychology and technology and taught at Stanford Graduate School of Business, opens with a counterintuitive claim:
Motivation has nothing to do with rewa
Q&A: Should You Pause Retirement to Buy a Bigger Home?
#698: We explore financial decision-making at different stages of life:
A high-earning federal couple debates whether to pause retirement contributions to accelerate a $200,000 down payment.A part-time healthcare provider seeks clarity on balancing a 401k and a traditional IRA.And a longtime listener asks a more personal question: Is there anything we’re still figuring out ourselves?
We examine
Bill Gurley: The Biggest Career Regret Most People Have
#697: Most people regret the things they never tried.
Venture capitalist Bill Gurley says that pattern shows up again and again in research on end-of-life regrets — including regret about the careers people never pursued.
In this episode, Gurley joins us to talk about how people actually discover work they enjoy - and why the cliché to “follow your passion” sends people in the wrong direction.
Q&A: Should Your Emergency Fund Be Invested?
#696:
(01:50) Jeremy has been a careful budgeter for years, but a surprise car repair has him tapping his emergency fund. With rates falling, he’s wondering if cash is enough or if he should try bonds or a CD ladder to keep up with inflation.
(22:22) A listener in Canada has a DIY portfolio but is tempted by Dimensional Funds, which requires a pricey advisor. At the same time, she’s thinking ab
First Friday: Jobs Fell by 92,000. But the Economy Is Still Growing?
#695: The U.S. lost 92,000 jobs in February, pushing unemployment to 4.4 percent.That result contradicts a different report released two days earlier showing 63,000 jobs added, leaving economists trying to square the circle. Many agree that we're in a "low hire, low fire" jobs environment.We walk through several major economic stories using a three-layer framework: the household economy, markets a
Job Titles Don’t Mean What They Used To (And That Affects Your Pay) — with Dr. Ben Zweig (Part 2 of 2)
#694: There are about 90 million unique job titles in the U.S. labor market.
Ninety million.
If you are trying to negotiate a raise, switch companies or launch a side hustle, that number has consequences.
If titles do not line up, you cannot easily compare pay, scope or seniority. You might be doing the same work as someone with a higher title and higher salary - and never see it.
That proble
AI, Layoffs, and the Future of Your Career — with Dr. Ben Zweig (Part 1 of 2)
#693: AI learns your job in weeks … and you start wondering if you still have one.
That question shapes our conversation with Dr. Ben Zweig, CEO of Revelio Labs, a workforce data company that uses AI to build large employment databases and study labor market shifts. He also teaches a class on The Future of Work at NYU Stern School of Business. He holds a PhD in economics from CUNY Graduate Center
My Brother-in-Law Wants to Buy a Rental in Mexico. Good Idea?
#692: Anonymous (02:01) is excited about early retirement and family time but worried about his brother-in-law, who just returned from a vacation in Mexico with a bold plan: sell everything, move there, and buy an Airbnb to live in one unit and rent out the others. He wants to support him without watching him get in over his head. How can he navigate this tricky mix of family loyalty and financial
Your IQ Won't Save Your Career. Your AQ Might. – with Liz Tran
#691: Your IQ used to be your biggest career asset.
Then AI scored in the 99th percentile on the LSAT, the SAT, and the MCAT — and suddenly the cognitive skills that once set you apart became something anyone can access for free.
Executive coach Liz Tran joins us to talk about what actually drives career success and earning power now.
Her answer: AQ, or agility quotient — your capacity to han
Q&A: Should My Teen Go to College?
#690: Blanca (01:28): Blanca, an immigrant mother raising a 14-year-old, wants her son to think critically about college—not just as an experience, but as a financial decision. With the rising cost of higher education, she’s wondering how families can assess whether an undergraduate or graduate program is likely to pay off over time.
Brandon (30:05): Brandon in his forties, recently left full-tim
Your Brain Is Your Most Important Asset, with Dr. Majid Fotuhi, MD, PhD
#689: Most people think forgetting a name means their brain is failing.
Dr. Majid Fotuhi, a neurologist who taught at Johns Hopkins and Harvard, sees thousands of patients convinced they have Alzheimer's – only to discover they're dealing with poor sleep or stress.
Dr. Fotuhi joins us to break down the difference between cognitive decline, dementia and Alzheimer's disease. He explains why chron
Q&A: I'm Burned Out But Not Quite Ready to Retire
#688: Anonymous: "Anonymous Sheryl" is 38, mortgage-free and exhausted after 15 years of teaching. She’s torn between pushing a few more years toward FIRE or switching to relief teaching now for better work-life balance. How do you trade speed to FIRE for sustainability without blowing up the plan?
Anonymous : "Anonymous Ray" hired a bank portfolio manager but isn’t sure how to judge the results
First Friday: The Retirement Rules That Changed While You Weren't Looking
#687: Your tax refund might be $300 to $1,000 bigger this year, and that's just the beginning of what's changing with your money.
The Tax Foundation estimates most Americans will see significantly larger refunds thanks to seven major tax cuts. The child tax credit increased by $200. The standard deduction jumped by $750 for individuals or $1,500 for couples. The state and local tax deduction cap
Q&A: Are AI Stocks About to Crater?
#686: Rachel: Rachel is new to investing and has noticed the stock market being dominated by AI companies. She wants to make sure her portfolio is balanced without overexposing herself.Should she rethink her index fund strategy to protect against a potential AI bubble?
Sarah: Sarah just turned 65, owns her home outright, and has been relying on credit cards since losing her job last year. She’s w
10 Rules for Building a Portfolio That Actually Works for Your Life, with Cullen Roche
#685: You're not an investor. You're a saver.
That's the first of 10 principles Cullen Roche shares in this conversation about building what he calls "the perfect portfolio."
Roche, the founder and chief investment officer of Discipline Funds, argues that when you buy stocks on the secondary market, you're not actually funding companies or making investments in the traditional economic sense. Y
Why You Should “T-Bill and Chill” Instead of Using a Savings Account, with Cullen Roche
#684: Most people search for the perfect portfolio — the one allocation that works in every market, at every age, for every goal. This interview starts by explaining why that portfolio does not exist.
We talk with Cullen Roche, founder and chief investment officer of Discipline Funds, about why copying someone else’s portfolio can backfire, and why portfolio design works better when it starts wit
How to Teach Kids About Money, with Dr. Stephen Day
#683: Candy now — or a toy later? You slide play money across the table and let your kid choose.
That moment kicks off this episode, where Dr. Stephen Day joins us to talk about building a “mini economy” at home.
Dr. Day is the director of the Center for Economic Education at Virginia Commonwealth University. He also holds a PhD in social studies and economics curriculum and instruction. His wo
52 Tiny Improvements in 2026 [GREATEST HITS]
#682: Grab the FREE handbook: affordanything.com/financialgoals
For 76 years, the British cycling team lost — every season, without exception. Then they changed how they approached improvement, focusing on tiny gains instead of dramatic overhauls.
In today's episode, we unpack how they became champions – and apply those same tactics to our financial life.
This episode originally aired in
How NOT to Invest, with Barry Ritholtz
#681: Barry Ritholtz's mom sold real estate. Those dinner table conversations about mortgages helped him spot the 2008 crash before most of Wall Street did.
Now he runs Ritholtz Wealth Management and joins us to explain why we're often our own worst investment enemy.
He breaks investing mistakes into three categories: bad ideas, bad numbers, and bad behavior.
Here's what stood out. Research sho
Q&A: I Want to Retire Early Without Selling My Stocks in a Crash
#680: Mia: Mia and her husband are planning early retirement and want to draw down their taxable brokerage accounts for the next decade. She’s considering a securities-backed line of credit to defer taxes during market downturns.
Can a securities-backed line of credit smooth taxes in early retirement, or are there hidden risks?
Jean: Jean, a freelance creator, wants to take a self-made sabbatica
Why AI Taking Your Job Isn't the Real Problem, with Fmr. OpenAI Exec Zack Kass
#679: Will you still have a job in five years? Zack Kass, former OpenAI executive and 16-year AI veteran, joins us to tackle the question that keeps knowledge workers up at night.
Most people worry about the economics — who can pay the bills if AI takes their job? Kass flips the question: What happens when work no longer defines who you are? He argues we're heading for an identity crisis bigger
Q&A: We Want to Save Senior Dogs … But Should We Sell Our Rental to Do It?
#678: Anonymous (01:52): "Victoria" is 51, single, and still enjoying their W2 job while building a side business from a passion hobby. They’re thinking about heavy Roth conversions, planning for retirement, and wondering how much traditional money to leave untouched. Should Alex prioritize tax efficiency, or focus on growth and flexibility?
Anonymous (34:29): "Gwyneth" and her husband moved to
First Friday: What 2026 Means for Your Money
#677: Happy New Year! We're kicking off 2026 with a reality check on where your money stands right now.
The Good News: Gas prices dropped below $3/gallon. Inflation cooled to 2.7%. The Fed cut rates again. GDP grew 4.3% (surprisingly strong). Gold hit $4,500 an ounce. And 19 states raised minimum wages.
The Not-So-Good: Health insurance jumped 10-18%. Unemployment ticked up. Mortgage rates are s
Q&A: Should You Keep Part of Your Money Outside the U.S.?
#676: Ally:How can I optimize my asset allocation and Roth contributions now that I’m over $1 million in assets?
I’m 45, single, never married, with about $1.2 million in assets. Roughly $100,000 is in stocks, which might scare some people.
Here’s my breakdown:
Vanguard brokerage account: VTSAX $132,000, ISCV $5,000, VOO $5,000
Vanguard Rollover IRA: VTSAX $65,000, IVV $25,000, VOO $62
[E] The Myths We Believed About Startups [GREATEST HITS]
#675: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.
Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth.
____
In this episode,
[R] Remember When Inflation Was High and Rates Were Rising? [GREATEST HITS]
#674: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.
Today's letter R stands for Real Estate. This episode originally aired in May 2022, but the insights on long-distance investing remain just as relevant for anyone feeling priced out of their local market.
We tackle the five biggest challenges of investing far from home – from fear of the unknow
[I] Why Young Investors Focus on the Wrong Things [GREATEST HITS]
#673: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.
Today's second letter I stands for Investing. This episode originally aired in April 2022, but the framework remains one of the most practical guides we've shared for building wealth at any age.
Nick Maggiulli joins us to reveal why most young investors obsess over the wrong metrics — and share
[I] The Hidden Information That's Costing You Money [GREATEST HITS]
#672: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E.
Today's letter I stands for Increasing Your Income. This episode originally aired in August 2024, but the strategies are more essential than ever.
Jeff Wetzler, Ed.D., reveals why the people around us withhold crucial information — and how asking better questions can transform your negotiation
[F] Why Your Brain Sabotages Your Money [GREATEST HITS]
#671: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E.
Today's letter F stands for Financial Psychology. And we're diving deep with a conversation that changed how thousands of our listeners think about money.
This episode originally aired in November 2022, but the insights feel more relevant than ever. Dr. Daniel Crosby reveals why your brain is y
Are Credit Card Rewards Really Worth It in 2026?
#670: As we close out 2025, premium credit cards are more expensive and more complicated than ever. It’s fair to ask whether the points game is still worth the effort.
We sit down with Chris Hutchins, host of All the Hacks, to talk about what’s changed in credit card rewards, and how to decide whether to stick with travel points, switch to cash back, or run a hybrid strategy that keeps your lif
44 Years Old, $2 Million Saved – Why They're Still Hesitant to Downshift
#669: Slade (01:43) - Slade, 44, and his wife plan to downshift careers in the next five to seven years while raising their 11-year-old daughter. They want to know how to reallocate their $685K brokerage account and plan withdrawals to make the transition financially smooth.
David (21:50) - David has a high school senior and is deciding how to pay for college. Should he tap the $60K 529 plan now
Why Taking a Year Off Might Be Your Smartest Money Move, with David Bach
#668: We’re joined in-studio by David Bach, bestselling author of The Automatic Millionaire and The Latte Factor. He’s updated his most popular book (over two million copies sold) and this is his last big launch as he heads into retirement.
Together, we wrestle with a problem our listeners know well: what happens when you’ve built the habit of saving, investing, optimizing … and then feel weird
Should You Ever Get a 50 Year Mortgage? — with Dr. Karsten Jeske
#667: Home prices have outpaced wages for more than a decade, and first-time buyers are stretching further every year. Now a new idea is entering the conversation, the 50-year mortgage. It promises lower monthly payments, yet it reshapes everything from equity growth to long-term risk.
In this episode we sit down with Karsten Jeske, PhD, CFA from Early Retirement Now, a former Federal Reserve
First Friday: The Strange Economics of Feeling Poor While Spending More Description:
#666: In this First Friday economic update, we explore the paradox defining our current economy: record-breaking retail numbers alongside plummeting consumer confidence.
In this First Friday economic update, we explore the paradox defining our current economy: we're spending more than ever, while feeling worse about money than we have in years.
The Bureau of Labor Statistics hasn't released job
Q&A: How Much Insurance Is Enough When You’re Protecting Your Wealth
#665: If you’ve ever stared at an insurance quote and wondered, “Is this really worth it?”, you’re not alone. Liability and umbrella policies can feel like an expensive mystery, especially when your net worth is growing and your risks are shifting.
In today’s episode, we dig into a listener’s dilemma about soaring liability and umbrella insurance costs, and we explore how to think clearly about p
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