Afford Anything | Get Smarter With Money
- Episódios
- 813
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- Último episódio
- 13 nov 2026
Sobre o podcast
45 million downloads. One question: what does it actually take to build wealth?
Each week, Paula Pant brings in economists, investors, business leaders, authors, and researchers to dig into the five pillars of financial freedom — financial psychology, increasing income, investing, real estate, and entrepreneurship. Deep insights rooted in economics and behavioral finance. First-principles thinking. No surface-level tips.
Follow or Subscribe to hear new episodes every Tuesday and Friday.
Get smarter with money. Build wealth.
Episódios 813
Why You Feel Broke When You’re Not, and the Risky Bets It Can Lead To, with Jill Schlesinger
Feel behind even when you're doing everything right? Get the key takeaways from this episode, including how to tell if you're actually behind or just feel that way: https://affordanything.com/episode767You can …
Notas do episódio
Feel behind even when you're doing everything right? Get the key takeaways from this episode, including how to tell if you're actually behind or just feel that way: https://affordanything.com/episode767
You can be ahead of where your parents were at your age and still feel broke. Jill Schlesinger explains why that feeling is so common right now, and why it's what pushes people toward long-shot bets.
Jill Schlesinger, CFP®, is the Emmy-winning business analyst for CBS News and host of CBS's new show Money Moves. Before media, she spent 14 years as co-owner and chief investment officer of an investment advisory firm.
In this episode, we discuss:
- Why you can feel behind even when you're ahead of where your parents were
- Why strong economic data still feels bad after a burst of inflation
- How social media keeps you feeling behind, even when you know it's baloney
- Why feeling stuck makes sports betting and meme stocks look reasonable
- How a financial plan turns money anxiety into specific next steps
- What to weigh before leaving a steady job for something new
If you're doing the right things and still feel behind, this episode will help you see where you actually stand before that feeling talks you into a risky bet.
🔗 RESOURCES MENTIONED
👉 Jill's website and where to send her your money questions: https://www.jillonmoney.com
👉 Watch or listen to Money Moves with Jill Schlesinger: https://www.cbsnews.com/money-moves-with-jill-schlesinger
👉 Jill's book on making a big life or career change, The Great Money Reset: https://www.jillonmoney.com/the-great-money-reset
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The 5 Levels of Investors, and Why Some People Never Leave Level One, with David Leiter
Which of the 5 investor levels are you? Read the key takeaways and get your one-hour action plan for leveling up here: https://affordanything.com/episode766Most investors start out as gamblers, jumping on …
Notas do episódio
Which of the 5 investor levels are you? Read the key takeaways and get your one-hour action plan for leveling up here: https://affordanything.com/episode766
Most investors start out as gamblers, jumping on whatever's going up. The danger isn't starting there. It's staying there for years while studying charts and believing you've become a professional.
David Leiter started on Wall Street at Credit Suisse First Boston in the 1990s and has invested in New York City real estate since 1998. He's the author of Stop Making Stupid Investments: 7 Rules to Avoid the Hype and Build Real Wealth.
In this episode, we discuss:
- How to tell whether you're investing or just chasing price moves
- The five levels investors move through, from gambling to living off your investments
- Why steady index fund investing is a great place to land, if hot tips don't pull you away
- What changes when you start asking yourself, "Am I feeling FOMO right now?"
- Why even experienced investors slide back down when the next hot thing shows up
- Why investing rewards temperament more than intelligence
- Seven rules to check yourself against before your next investment
Wherever you'd place yourself today, this conversation shows you what keeps people stuck at the first level, and what it takes to move past it.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(06:12) The 10% crypto offer that went to zero
(09:14) Why most investors start out as gamblers
(21:11) When a billionaire panicked, he bought more stocks
(27:35) Why a 50% loss needs a 100% gain to recover
(35:47) Why investing rewards temperament over IQ
(38:57) Coworkers called him a slumlord. He kept buying.
(52:30) Two things to demand before any private deal
(57:10) $100,000 invested, $80 a month back
(59:18) Why a falling stock doesn't mean a failing company
(1:02:04) Why he bought for cash flow, not neighborhood hype
🔗 RESOURCES MENTIONED
👉 Stop Making Stupid Investments by David Leiter: https://a.co/d/0ekcjy0y
👉 David's website: https://www.theultimateinvestor.com
👉 David's YouTube channel: https://www.youtube.com/@theultimateinvestor
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
First Friday: Stocks Crashed. Jobs Boomed. Now What?
One major tech index lost $2.3 trillion in a single day on Thursday – the biggest one-day loss on record. The S&P 500 fell 4.4 percent, the Dow dropped more than 1,800 points and the Nasdaq slid into correction …
Notas do episódio
One major tech index lost $2.3 trillion in a single day on Thursday – the biggest one-day loss on record. The S&P 500 fell 4.4 percent, the Dow dropped more than 1,800 points and the Nasdaq slid into correction territory.
👉 Join us for what happens next: affordanything.com/newsletter
The selloff started with AI stocks after the midterm elections raised questions about data center construction.
This First Friday episode covers what happened, why it dragged down the whole market and what the latest economic numbers mean for your wallet.
We explain concentration risk and what it means for your index funds. We also talk about how long-term investors can think about short-term swings.
Next, the jobs report. The U.S. added 165,000 jobs in October, nearly three times what economists expected, and unemployment dipped to 4.1 percent. The government also revised August and September up by a combined 84,000 jobs.
We compare those numbers with private payroll data from ADP, which tells a very different story about one major sector. We also look at job openings, quits and a jump in the number of people stuck in part-time work.
The Fed held interest rates steady in October in a 10-2 vote, and both dissenters wanted a hike. We also revisit a 1986 vote that left Paul Volcker on the losing side.
Inflation keeps climbing. Consumer prices rose 3.7 percent over the past year, driven largely by gas. Wages grew 3.1 percent, so paychecks still trail prices. Social Security recipients get a 3.6 percent raise in January, though higher Medicare premiums will eat into it.
The economy grew at a 3.4 percent annual rate in the third quarter. We break down what drove that growth.
Finally, bonds. Long-term Treasury yields hit their highest level in more than two decades in early October, then fell. We explain a simple rule of thumb for where the 10-year Treasury tends to trade and what today’s rate says about investors’ inflation expectations. Mortgage rates have now dipped three weeks in a row.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Q&A: I’m at High Risk for Alzheimer’s. Is $2.5M Enough to Take Care of My Family?
Most retirements in the U.S. aren’t voluntary. Layoffs, health problems or caring for a family member decide the date for most people, so real financial planning has very little to do with skipping lattes.Paula …
Notas do episódio
Most retirements in the U.S. aren’t voluntary. Layoffs, health problems or caring for a family member decide the date for most people, so real financial planning has very little to do with skipping lattes.
Paula and former financial planner Joe Saul-Sehy answer three listener questions. The first is from an Air Force major with $2.5 million saved whose parents both have early-onset Alzheimer’s. The second is from a 58-year-old early retiree deciding whether to rent or buy her next home. The third is from a couple weighing whether to pay down a 6% mortgage.
In this episode, we discuss:
- Why to buy disability and long-term care insurance before you take a genetic test
- How to plan for long-term care costs without draining the rest of your family
- Which estate documents to sign now, and the trust step most people skip
- Why the person raising your kids and the person managing their money shouldn’t be close friends
- How to use the price-to-rent ratio to decide whether to rent or buy
- Whether paying down a 6% mortgage really earns a guaranteed 6% return
- Why extra mortgage payments won’t hurt you if you refinance later
If you’ve been treating personal finance as a budgeting exercise, this episode shows what planning ahead looks like. It also shows why planning makes you more flexible, not less.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(00:00) Why most retirements aren’t your choice
(06:57) What Charlie Munger regretted at 99
(15:35) $2.5M saved and a family history of Alzheimer’s
(17:11) Why to buy insurance before a genetic test
(29:46) How to handle the sticker shock of long-term care
(32:21) Estate paperwork to sign before you need it
(38:53) Why your kids’ guardian and money manager shouldn’t be friends
(54:56) The one ratio that tells you to rent or buy
(1:07:39) Is a 6% mortgage a guaranteed 6% return?
(1:14:03) 15 families could pay off their mortgage. None did.
🔗 RESOURCES MENTIONED
IS YOUR FAMILY COVERED IF YOU CAN’T WORK? MAP YOUR INSURANCE, SAVINGS AND RETIREMENT ON ONE FREE PAGE AND FIND THE GAPS 👉 http://affordanything.com/cornerstone
👉 Joe Saul-Sehy’s show, Stacking Benjamins: https://www.stackingbenjamins.com
👉 Lacey Langford’s MILMO Show (money planning for military families): https://laceylangford.com/expert-resources/milmo-show
👉 Our interview with estate planning expert Andrea Baumann Lustig: https://affordanything.com/725-what-most-families-get-wrong-about-passing-down-wealth-with-andrea-baumann-lustig
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Acorns CEO: The Scariest Part of Investing Is the First Step, with Noah Kerner
Over half of young Americans avoid looking at their money to cope with stress, and the CEO of Acorns says he was one of them. In his twenties, even a guaranteed 2.5% return felt too scary to touch, and it cost …
Notas do episódio
Over half of young Americans avoid looking at their money to cope with stress, and the CEO of Acorns says he was one of them. In his twenties, even a guaranteed 2.5% return felt too scary to touch, and it cost him a decade of growth.
Noah Kerner is CEO and chairman of Acorns, the automated saving and investing app whose customers have invested more than $33 billion, often starting with spare change.
👉 Acorns: https://affordanything.com/acorns
In this episode we discuss:
- Why avoiding your money feels like relief, and what it quietly costs you
- How to make saving so small you can't talk yourself out of it
- Why so many people feel pessimistic about money despite a long bull market
- How the app you use can change what you do when markets drop
- Why the best investing strategy is usually the boring one
- How to tell patience from prediction when betting looks like investing
- How a founder copes when his body forces him to stop working
If you've been putting off looking at your accounts, or you're tempted by faster ways to grow your money, this conversation offers a calmer path forward.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(00:00) Over half of young people avoid their money
(03:07) Why we avoid money
(05:43) How families pass down fear
(07:54) Automate investing with spare change
(13:32) Why strong markets feel scary
(15:57) How apps shape money habits
(21:07) Why betting feels so tempting
(27:08) Patience versus prediction
(28:44) Buy now, pay later pitfalls
(31:40) Build businesses that help people
(34:56) Noah’s path to Acorns
(41:16) Give small shareholders a voice
(46:36) When health forces work aside
(51:10) Business risks and team building
(55:11) Paula’s three key takeaways
🔗 RESOURCES MENTIONED
👉 AVOIDING YOUR MONEY COST HIM A DECADE. FIND OUT IF YOU'RE AN AVOIDER TOO: https://affordanything.com/fiire
👉 Acorns: https://affordanything.com/acorns
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Q&A: I’m the Executor of Dad’s $500K Portfolio. Should I Cash It Out?
A bond fund that lost 38% feels like proof you should have bought individual bonds instead. But individual bonds would have lost value too; you just wouldn’t get a statement telling you so.Former financial …
Notas do episódio
A bond fund that lost 38% feels like proof you should have bought individual bonds instead. But individual bonds would have lost value too; you just wouldn’t get a statement telling you so.
Former financial planner Joe Saul-Sehy joins Paula to answer three listener calls. The first comes from an executor deciding whether to move his late father’s $500,000 brokerage account to cash during probate (the court process of settling an estate). The second is from an investor whose bond fund lost 38% in six years, and the third is from a 401(k) plan manager of 23 years who pushes back on Joe’s take on target-date funds.
In this episode, we discuss:
- How an executor can protect an estate’s value without market timing
- Why splitting the money 50/50 between stocks and cash can work, if every heir agrees
- Why individual bonds lose value when rates spike too, even when no statement shows it
- How a bond advertising 6% can still lose you money if you overpay for it
- When a bond fund makes more sense than individual bonds, and vice versa
- Why short-term bonds can drag down a long-term portfolio
- Whether target-date funds are a smart default or a first step to outgrow
If you’re settling a parent’s estate, second-guessing your bonds, or wondering whether your 401(k) default is good enough, this episode gives you a way to weigh the tradeoffs instead of reaching for a one-size-fits-all rule.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(00:00) Why disability insurance costs so much
(09:10) An executor’s $500K dilemma: stay invested or cash out?
(11:41) Why Joe would move the estate to cash
(15:13) The 50/50 split both hosts can live with
(24:56) Her bond fund lost 38%. Now what?
(27:33) Why individual bonds wouldn’t have dodged the loss
(32:48) How a “6%” bond can still lose money
(35:20) Why Paula bought her first bonds at 5.2%
(53:54) A 401(k) plan manager defends target-date funds
(1:05:40) Why so many people ignore their own money
🔗 RESOURCES MENTIONED
OUTGROWING YOUR TARGET-DATE FUND? HERE’S WHICH ACCOUNT EACH NEW FUND BELONGS IN 👉 https://affordanything.com/assetlocation
Free executor checklist from Stacking Benjamins 👉 https://stackingbenjamins.com/estate
Buy Treasury bonds directly from the government 👉 https://www.treasurydirect.gov
Share your worst investment mistake for a future episode 👉 https://affordanything.com/voicemail
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
3 Million Americans Got Rich From Boring Businesses. Here's How, with Owen Zidar & Eric Zwick
#761: Roughly 3 million Americans who own private businesses — car dealerships, beer distributors, dental practices — are collectively worth more than ten times the entire Forbes 400. Most of them didn't start …
Notas do episódio
#761: Roughly 3 million Americans who own private businesses — car dealerships, beer distributors, dental practices — are collectively worth more than ten times the entire Forbes 400. Most of them didn't start rich, and you've probably never heard of a single one.
Economists Owen Zidar (Princeton) and Eric Zwick (University of Chicago Booth School of Business) spent more than a decade linking anonymized tax records to the people who own America's private businesses. They share what they found in their new book, The Everywhere Millionaire.
In this episode, we discuss:
- Why owning all of a small business can rival owning a sliver of a startup
- Which unglamorous industries quietly produce the most wealth
- How to decide whether to buy an existing business or start your own
- How retiring owners and seller financing (paying the owner back over time) open doors for buyers
- How to run cheap experiments so no single failure wipes you out
- When to double down on one business versus diversify
- What the data says about whether you need to be born rich
If you're weighing a steady paycheck against owning something yourself, this conversation shows who actually takes that path, what it demands, and how often it pays off.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(02:20) Why 3 million business owners outweigh the Forbes 400
(06:13) The overlooked businesses behind America's quiet fortunes
(11:22) Why retiring owners could be your buying opportunity
(17:31) Own all of something small, not 2% of a unicorn
(21:36) Buy a business or start one?
(29:24) How to fail small without getting wiped out
(34:35) What yacht and private jet data revealed
(44:20) Most successful founders didn't grow up rich
(01:06:31) Double down or diversify once it works?
(01:18:51) Should you leave a high-paying job for this?
🔗 RESOURCES MENTIONED
👉 Buy a retiring owner's business or build your own? Find the ownership path that fits your money and risk: https://affordanything.com/fiire
👉 The Everywhere Millionaire (book): https://link.amazon/B04y1xfaU
👉 The Everywhere Millionaire on Substack: https://everywheremillionaire.substack.com
👉 The Millionaire Next Door, by Thomas J. Stanley and William D. Danko: https://link.amazon/B01HtGgHg
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Q&A: $1 Million Invested, $100K a Year to Live On. Do We Ever Need to Save Again?
#760: A couple in their late 30s and early 40s with $1 million invested may never need to save another dollar for retirement, because left alone, that money could grow to about $4 million. The harder question …
Notas do episódio
#760: A couple in their late 30s and early 40s with $1 million invested may never need to save another dollar for retirement, because left alone, that money could grow to about $4 million. The harder question isn't the money. It's which of them keeps working to carry the family's health insurance.
Paula and Joe start with Beth, an accountant married to a burned-out tech worker, who wants to know whether they can cut back on work now. Then they tackle a retiree's Ivy League financial aid questions and a New Yorker asking whether renting forever is a financial death sentence.
In this episode, we discuss:
- How to tell if you've saved enough for retirement to stop contributing
- Why one spouse should stay employed to carry the family's health insurance
- Where to find part-time work in fields that rarely advertise it
- How to turn a high savings rate into more time with young kids now
- Why lowering your income may not unlock more Ivy League financial aid
- Why test prep may matter more than hiring an admissions counselor
- Why renting in an expensive city isn't throwing money away
If you've built a solid nest egg but feel stuck working five days a week, this episode shows how to check whether you can ease off now instead of waiting for full retirement.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(06:53) $1 million by 40 and burned out: can they downshift?
(10:18) Why one spouse should keep the health insurance
(11:41) Where to find part-time work that still pays well
(14:41) Why work-life balance comes in seasons, not days
(16:49) What it really means to stop saving for retirement
(18:10) How $1 million could grow to $4 million untouched
(20:47) Turn your savings gap into time with your kids
(27:40) Why a lower income may not unlock Ivy aid
(37:12) Why test prep beats an admissions counselor
(50:32) Is renting really throwing money away?
🔗 RESOURCES MENTIONED
👉 RETIREMENT ALREADY COVERED? MAP WHERE YOUR NEXT DOLLAR SHOULD GO — ON ONE FREE PAGE: https://affordanything.com/cornerstone
👉 Joe's conversation with Lynda Gratton on taking breaks and changing careers over a longer life (Stacking Benjamins SB1898): https://www.stackingbenjamins.com/rethinking-retirement-100-year-life-1898
👉 Read This Before Planning for College (Stacking Benjamins x The College Investor): https://www.stackingbenjamins.com/collegeguide
👉 The College Investor, Robert Farrington: https://thecollegeinvestor.com
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
My Bank Account Hit Zero ... Then I Got Rich -- with Jaspreet Singh of Minority Mindset
#759: At 19, Jaspreet Singh bought a rental for $8,000. What followed was a nightmare tenant, a lawsuit, and a later house stripped of its copper, and it taught him what the real estate books leave out …
Notas do episódio
#759: At 19, Jaspreet Singh bought a rental for $8,000. What followed was a nightmare tenant, a lawsuit, and a later house stripped of its copper, and it taught him what the real estate books leave out.
Jaspreet is the founder of Minority Mindset, a personal finance YouTube channel with more than 2.5 million subscribers, and CEO of Briefs Finance. He’s also a licensed attorney who chose to build businesses instead of practicing law.
Avoid these 7 expensive rental property mistakes → https://affordanything.com/rent
In this episode, we discuss:
- How hiring the cheapest property manager can cost you the most
- Why skipping a $200 inspection led to his worst deal ever
- Why an employee who’s just coasting hurts a small team more than a weak one
- A simple two-list exercise that shows whether your hard work actually pays
- How the tax code rewards owners and investors over employees
- How a terrible market timer who never sold still turned $100,000 into more than $1 million
- Where AI’s ripple effects could create opportunities beyond the AI companies themselves
Whether you’re weighing a first rental, a business, or simply investing more consistently, this conversation shows what each path really costs and how to learn those lessons for less than Jaspreet paid.
🔗 RESOURCES MENTIONED
JASPREET LEARNED RENTALS, BUSINESS, AND INVESTING THE EXPENSIVE WAY. MAP YOUR OWN PATH FOR FREE 👉 https://affordanything.com/fiire
Minority Mindset on YouTube 👉 https://www.youtube.com/@MinorityMindset
Briefs Finance and the free Market Briefs newsletter 👉 https://www.briefs.co
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Q&A: "I’m 26 and No Longer Motivated by Money. Am I Unemployable?”
#758: Joe says that if you tell an employer you’re not motivated by money, you’re unemployable. Paula says that’s exactly the person she wants to hire. Former financial planner Joe Saul-Sehy joins Paula to …
Notas do episódio
#758: Joe says that if you tell an employer you’re not motivated by money, you’re unemployable. Paula says that’s exactly the person she wants to hire.
Former financial planner Joe Saul-Sehy joins Paula to answer a question from a 26-year-old whose net worth is already 10 times her annual spending. Then they take on two more: whether target date funds are worth it, and whether a dad of young kids should make a career change that cuts his income by 60%.
In this episode, we discuss:
- Why not being motivated by money can make you a better hire
- The two traits Paula looks for when she hires
- How to tell whether a small business is a good place to work, and when it isn’t
- A quick test for whether you’d actually enjoy your coworkers
- When a target date fund makes sense, and when it holds you back
- How to decide whether to make a big career change now or wait
- Why your savings might be meant for exactly this kind of leap
If you’ve saved enough that a paycheck no longer drives your choices, this episode will help you figure out what should.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(02:32) She’s 26 and no longer motivated by money
(07:23) What Paula looks for instead of money motivation
(12:54) The hidden risk of working at a tiny company
(24:55) The 8-hour layover test for coworkers
(33:05) Why Paula put her parents in target date funds
(40:24) Joe’s 30-minute alternative to target date funds
(51:33) Why your 401(k) target date fund may be junk
(58:33) The case for target date funds as harm reduction
(01:08:01) Should he take a 60% pay cut to switch careers?
(01:13:37) Why waiting “one more year” rarely helps
🔗 RESOURCES MENTIONED
👉 Building your own mix instead of a target date fund? See which account each fund belongs in: https://affordanything.com/assetlocation
👉 Episode #709, planning for a child with special needs, with Keith Wargo: https://affordanything.com/709-the-financial-reality-of-developmental-disability-with-keith-wargo/
👉 Stacking Benjamins, Joe’s podcast: https://www.stackingbenjamins.com/
👉 Strategic Coach, the entrepreneur coaching program Joe recommends: https://www.strategiccoach.com/
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Steve Jobs Hated the Name “Genius Bar.” How He Came Around, with Ron Johnson
#757: Ron Johnson is the creator of the Apple Stores and former CEO of JCPenney. At age 24 Ron Johnson turned down a $120,000 Goldman Sachs offer to unload trucks for $40,000, and that detour led Steve Jobs to …
Notas do episódio
#757: Ron Johnson is the creator of the Apple Stores and former CEO of JCPenney.
At age 24 Ron Johnson turned down a $120,000 Goldman Sachs offer to unload trucks for $40,000, and that detour led Steve Jobs to hire him to build the Apple Store. Years later, he took over JCPenney and watched it fail for a reason that had nothing to do with his vision.
Ron Johnson created the Apple Store and worked directly for Steve Jobs for 12 years, after bringing designer products to Target. He later served as CEO of JCPenney and is the author of Shop Different.
In this episode, we discuss:
- How to weigh a lower-paying job that teaches you more
- How to set goals big enough that people work harder
- How to persuade a team whose top priority is not getting fired
- How to change a strong-willed boss’s mind
- Why a bold plan fails without trust, and how to build trust first
- What a rush of early customers can hide about a new business
- How to get out of your head when you’re overthinking a decision
Whether you’re weighing a career risk, building a business on nights and weekends, or trying to get people behind a bold idea, this conversation shows what it takes, and what it costs to skip a step.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(02:14) Why a few columns made Steve Jobs furious
(08:44) How he talked Steve Jobs into shopping malls
(15:33) Why he turned down $120K to unload trucks
(22:10) Why big goals beat small improvements
(29:24) How to sell a risky idea to cautious coworkers
(37:02) The $30 tea kettle that caught Steve Jobs’ eye
(46:02) Why a record-breaking opening day was misleading
(56:26) How a hotel inspired the Genius Bar
(1:14:40) Why JCPenney failed: trust, not vision
(1:35:54) How to escape analysis paralysis
🔗 RESOURCES MENTIONED
👉 Would you turn down $120K for work you love? Find out what’s really driving your money choices: https://affordanything.com/fiire
👉 Ron’s Book, Shop Different: https://amzn.to/4yFA1SH
👉 Ron’s website: https://ronjohnsonshopsdifferent.com
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
How Losing $500K in ‘08 Led One Trader to a Different Kind of Portfolio, with Jared Dillian
#756: In September 2008, Jared Dillian watched about half a million dollars of Lehman Brothers stock go to zero in a single week. He wasn't allowed to sell any of it. What he built afterward is a portfolio …
Notas do episódio
#756: In September 2008, Jared Dillian watched about half a million dollars of Lehman Brothers stock go to zero in a single week. He wasn't allowed to sell any of it. What he built afterward is a portfolio designed so he never goes through that again.
Jared Dillian was a trader at Lehman Brothers from 2001 until its collapse, and ran its exchange-traded fund desk. He's the author of The Awesome Portfolio and taught finance at the university level for 13 years.
In this episode, we discuss:
- Why to sell your company stock as soon as you're allowed to
- How living below your means gave him the freedom to start a business when Lehman fell
- How to gauge your real risk tolerance with a simple Las Vegas test
- How a portfolio split five ways (stocks, bonds, cash, gold, real estate) held up in 2008
- Why a 20% cash cushion can be an advantage instead of a drag
- What long-term bond yields reveal about the economy that stocks don't
- What it would actually take to close the Social Security funding gap
If most of your money sits in an index fund or your employer's stock, this conversation will help you figure out how big a drop you could actually stomach before the next real bear market tests you.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(02:29) Walking into Lehman Brothers the day it collapsed
(04:38) The $500,000 in company stock that went to zero
(06:57) How cheap living let him start a business instead
(19:54) Why buy-and-hold hasn't faced a real crash since 2008
(22:52) The Las Vegas test for your risk tolerance
(27:07) A five-way portfolio that fell just 9.8% in 2008
(28:46) The one scenario where this portfolio struggles
(29:33) Is 20% cash too much with inflation?
(44:45) Why bond yields are the economy's warning light
(51:25) Why half of retirees claim Social Security at 62
🔗 RESOURCES MENTIONED
BEFORE YOU ADD BONDS OR REAL ESTATE FUNDS, KNOW WHICH ACCOUNT THEY BELONG IN 👉 https://affordanything.com/assetlocation
Jared Dillian's website 👉 https://www.jareddillianmoney.com
The Awesome Portfolio by Jared Dillian 👉 https://amzn.to/4ART5i4
Jared Dillian on X 👉 https://x.com/dailydirtnap
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
First Friday: AI, Debt, and a Social Security Shortfall. Should Your Money Plans Change? With Rob Berger
#755: Many retirees fear running out of money more than they fear dying. AI is reshaping the economy, the U.S. now spends over $1 trillion on interest, and Social Security faces a shortfall. Rob Berger says if …
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#755: Many retirees fear running out of money more than they fear dying. AI is reshaping the economy, the U.S. now spends over $1 trillion on interest, and Social Security faces a shortfall. Rob Berger says if you're worried about all that, it's a sign you're thinking clearly.
Rob Berger is a former securities lawyer, founder of the personal finance site Dough Roller, and host of a nearly 300,000-subscriber YouTube channel on investing and retirement planning. He started writing about money in 2007, just months before the Great Recession.
In this episode, we discuss:
How to tell whether today's high stock prices should change your plan
When to trim a stock that's grown too big, and when to let it ride
Why a booming economy can still leave so many people feeling squeezed
What a looming Social Security shortfall could mean for your retirement
How to cover your basic bills with guaranteed income, whatever markets do
How to ease into retirement instead of going from 40 hours to zero
Why daily spending habits matter more than investing knowledge
Whether you're five years from retirement or five years into your career, this episode will help you separate what's truly changing from what never does.
🔗 RESOURCES MENTIONED
RETIREMENT WORRIES FEEL OVERWHELMING? SEE YOUR WHOLE FINANCIAL PICTURE ON ONE PAGE 👉 http://affordanything.com/cornerstone
Rob Berger on YouTube 👉 https://www.youtube.com/channel/UC9C17-OMxa-7oRSaCtztObw
Rob's free weekly retirement newsletter 👉 https://robberger.com/newsletter
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Q&A: We Have $80K in Cash and Want a 1–2 Year Sabbatical. Is It Enough?
#754: Four months of savings in the bank, a goal of eight, and a career break she's excited to fund. Does everything else really have to wait? Paula and Joe's answer: don't turn your emergency fund into an …
Notas do episódio
#754: Four months of savings in the bank, a goal of eight, and a career break she's excited to fund. Does everything else really have to wait? Paula and Joe's answer: don't turn your emergency fund into an emergency.
A 42-year-old UK listener asks how to split money between an emergency fund, a career break, and retirement. Then we map out a 30-something couple's sabbatical and ask whether you can objectively grade a politician on the economy.
In this episode, we discuss:
- How to tell a true emergency from an expense you know is coming
- How to rank competing savings goals when you can't fund them all
- How to protect retirement without putting your life on hold
- How to cover a sabbatical when your cash runs short
- Why low-income years are a prime window for Roth conversions
- How to test whether you can stomach an all-stock portfolio
- How to judge a politician's economic record without the spin
If you're juggling short-term plans and long-term goals and feel pulled in every direction, this episode will help you decide what gets funded first, and what can wait.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(05:30) The real difference between emergencies and expenses
(07:28) Why a former planner never said "emergency fund"
(13:13) The monthly math that breaks most wish lists
(18:36) One question that reveals what you really want
(26:37) Why four months of savings is enough for now
(33:48) Fund the sabbatical before earmarking a down payment
(37:00) Why a career break is prime time for Roth conversions
(43:24) How to test if you can handle a 22% drop
(1:01:53) Judge politicians on policies, not short-term results
(1:09:42) Why focusing on what you control grows your influence
🔗 RESOURCES MENTIONED
👉 Emergency fund, sabbatical, retirement? See which box each dollar belongs in with this free one-page worksheet: https://affordanything.com/cornerstone
👉 Paul Merriman's free model portfolios and investing courses: https://paulmerriman.com
👉 Adventure Capitalist by Jim Rogers: https://amzn.to/4xOaEg3
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Why 60,000 New York Apartments Sit Empty in a Housing Crisis, with Kenny Burgos
#753: New York City is short roughly half a million homes, yet at least 60,000 rent-regulated apartments sit empty. Under current rules, many owners lose less money by leaving them vacant than by fixing them …
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#753: New York City is short roughly half a million homes, yet at least 60,000 rent-regulated apartments sit empty. Under current rules, many owners lose less money by leaving them vacant than by fixing them up.
Kenny Burgos is CEO of the New York Apartment Association, which represents owners of rent-stabilized buildings, and a former New York State Assemblymember from the Bronx.
In this episode, we discuss:
- How New York's rent rules work, and why they've lasted since 1969
- Why the typical New Yorker pays about $1,600 while listings ask $5,500
- Why some buildings now sell for $50,000 an apartment, and why that isn't a deal
- How a rent freeze pushes costs onto market-rate renters and delayed repairs
- Why a targeted rent freeze for seniors and disabled residents works better
- What Vienna's housing model accounts for that New York's doesn't
- What aspiring landlords should weigh before buying rent-regulated property
Whether you own rentals, hope to, or just want to understand the rent-control debate, this episode shows what happens when costs keep rising and rents can't.
🔗 RESOURCES MENTIONED
👉 Ready to buy your first rental property, or get more out of the one you already own? Join the waitlist for Your First Rental Property. You'll be the first to know when enrollment opens: courses.affordanything.com
👉 New York Apartment Association: https://housingny.org
👉 Housing New York podcast with Kenny Burgos: https://housingny.org/housingnypodcast
👉 Kenny Burgos on X: https://x.com/KennyBurgosNY
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(03:44) Why New York's 1969 emergency rent rules never ended
(04:58) The surprisingly low rent most New Yorkers actually pay
(23:33) Why buildings now sell for $50,000 an apartment
(25:12) Costs rose 4.5%. Rents were frozen at 0%.
(31:39) The rent-freeze program that actually works
(39:38) Who really pays when rents are frozen
(47:13) Why 60,000 apartments sit empty during a shortage
(01:01:53) Buyout or pressure? The $150,000 question
(01:06:52) What Vienna gets right that New York doesn't
(01:16:18) Should you buy a rental in New York?
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Q&A: I’m Tired of Managing My Rental Property. Should I Sell It?
#752: A caller's rental is performing fine, but a late-paying tenant and a roof replacement have her ready to sell it before she moves to Madrid for her MBA. Paula argues the real fix isn't selling — it's a …
Notas do episódio
#752: A caller's rental is performing fine, but a late-paying tenant and a roof replacement have her ready to sell it before she moves to Madrid for her MBA. Paula argues the real fix isn't selling — it's a hire she hasn't made yet.
This week, Joe joins Paula to help a caller decide whether to sell a rental property from abroad, then dig into new data on why women's labor force participation dropped in July while their share of new jobs surged in August.
In this episode, we discuss:
- How to tell if you're making the right call for the wrong reason
- Why a new roof or a set of windows can be a form of forced investing
- The one hire that can solve the same problem as selling your rental
- A simple way to estimate a rental property's real return
- What to weigh before selling a working investment on gut feel alone
- Why women's labor force participation fell in July even as their job gains led the year
- Why the trades are becoming a stronger bet than a four-year degree for some new grads
This one's for anyone facing a big financial decision that feels more emotional than mathematical — whether that's a rental property, a career move, or a job you're not sure is worth keeping.
⏱️ TIMESTAMPSNote: Timestamps may vary slightly depending on dynamic ad placements.
(01:45) Why she wants to sell a rental that's "objectively good"
(03:25) When it's actually okay to sell a good investment
(10:03) One hire that stops panic-selling a rental property
(14:44) The simple math to compare rental returns vs. stocks
(17:31) Paula's own confession about hating her first rental property
(22:22) Why doing what you're best at beats doing everything yourself
(30:11) 100% of last month's labor force drop was women
(31:54) The real reasons women are leaving the workforce right now
(32:18) Why women got 85% of new jobs created this year
(47:00) The industry that could fix jobs and housing at once
🔗 RESOURCES MENTIONED
👉 Torn on selling a rental? Get our free 10-day guide, which includes a deal-analysis exercise to help you decide with the numbers, not just your gut: https://affordanything.com/fiire
👉 Sign up for our newsletter (get the new site first): https://affordanything.com/newsletter
👉 Leave us a voicemail with your own money question: https://affordanything.com/voicemail
👉 Read the BLS jobs report Paula cites in this episode: https://www.bls.gov/news.release/empsit.nr0.htm
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Why Self-Worth Predicts Your Income More Than Your SAT Score Does, with Marisa Franco
#751: The belief that’s quietly sabotaging your progress might not even be true. Free worksheet to question it: https://affordanything.com/turn-it-around Two people can grow up with the exact same test scores — …
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#751: The belief that’s quietly sabotaging your progress might not even be true. Free worksheet to question it: https://affordanything.com/turn-it-around
Two people can grow up with the exact same test scores — and as adults, one of them ends up earning double the other. Psychologist Marisa Franco says the deciding factor isn't intelligence, and it isn't luck. It's whether you actually believe good things are allowed to happen to you.
Dr. Marisa Franco is a psychologist and professor at the University of Maryland, and the New York Times bestselling author of Platonic. She's back to talk about her new book, Worth: The New Science of Self-Esteem and Secure Attachment.
In this episode, we discuss:
How self-worth — not intelligence or family income — predicts how much you'll earn as an adult
Why some people quietly sabotage their own portfolio right before they hit financial independence
The difference between "good" and "bad" high self-esteem, and why one of them wrecks relationships
Why getting more love or praise than you expect can make you pull away instead of lean in
How to actually process a hard emotion instead of shoving it down
Why hitting a big financial goal can leave you feeling strangely empty once you get there
How to rebuild your sense of self after losing an identity you were attached to
Whether you've ever undermined your own progress right before a finish line, or wondered why reaching a goal didn't feel the way you thought it would, this episode gives you a framework for understanding — and changing — that pattern.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(02:05) The two very different types of high self-esteem
(04:36) Self-esteem vs. self-worth: the real difference
(05:37) Why self-worth predicts income more than SAT scores
(12:21) Sabotaging your own portfolio right before you hit FI
(14:15) The self-fulfilling prophecy behind financial fear
(23:36) Why too much love can make you pull away
(25:05) How low self-worth blocks promotions and job offers
(36:13) The memory trick that can change your brain
(46:19) Why self-worth matters most in a bad market
(1:06:10) Does self-worth actually drive your net worth?
🔗 RESOURCES MENTIONED
👉 Worth: The New Science of Self-Esteem and Secure Attachment: https://drmarisagfranco.com/worth-the-book/
👉 Marisa's website (speaking, articles, more): https://drmarisagfranco.com
👉 Marisa on Instagram (for signed copies via Lost City Books): https://www.instagram.com/drmarisagfranco/
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Your "Diversified" Portfolio Might Secretly Be One Big Bet on AI, with Alec Litowitz
#750: Free worksheet: question the belief that might be keeping you stuck — before reality forces the update for you: http://affordanything.com/turn-it-around Alec Litowitz spent three decades building one of …
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#750: Free worksheet: question the belief that might be keeping you stuck — before reality forces the update for you: http://affordanything.com/turn-it-around
Alec Litowitz spent three decades building one of the world's largest hedge funds, and he says the highest-IQ people in the room are often the last to notice the world has changed. His answer isn't more intelligence — it's the willingness to be wrong, quickly, and update before everyone else catches up.
Alec co-founded Citadel alongside Ken Griffin and later founded Magnetar Capital, one of the largest alternative asset managers in the world. His new book, The Adaptability Quotient, is out September 15.
In this episode, we discuss:
How adaptability quotient (AQ) differs from IQ and EQ — and why it matters more now
What a doomed Antarctic expedition reveals about real adaptability
Why AI makes knowledge abundant and judgment scarce
How to stop needing to be right so you can update faster
The real reason Blockbuster lost to Netflix (it wasn't a bad decision)
A 4-part test for telling a temporary shift from a permanent one
Why a "diversified" portfolio might secretly be one big bet right now
This episode is for anyone whose career, portfolio, or plans feel less certain than they used to — a way of thinking that doesn't require predicting the future, just noticing when your old model has stopped working.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
How a Blind Man and His Dog Survived 9/11 from the 78th Floor
#749: Michael Hingson was on the 78th floor of the North Tower of the World Trade Center when the first plane hit on Sept. 11. He felt the impact, but couldn’t see it. Michael has been blind since shortly after …
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#749: Michael Hingson was on the 78th floor of the North Tower of the World Trade Center when the first plane hit on Sept. 11.
He felt the impact, but couldn’t see it. Michael has been blind since shortly after birth.
Alongside his guide dog, Roselle, they descended 1,463 steps – escaping just before the South Tower, 100 yards away, collapsed. They then helped a woman who was temporarily blinded by the dust.
Michael's story answers the question – What do you do when something terrifying is happening, you don't have enough information, you cannot control the outcome, and everyone around you is beginning to panic?
Michael's answer is surprisingly practical.
1. Prepare before you need the preparation.
2. Know what you know, know what you don't know.
3. Stop mentally rehearsing outcomes you cannot control
4. Keep acting on the part that remains within your control.
He had deliberately learned the World Trade Center's exits, emergency procedures, physical layout, and systems long before Sept 11 because he believed that was part of being responsible for his office.
When the building was struck, he describes that preparation as a “mindset” that simply kicked in.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(00:00) Life before September 11
(24:34) The plane hits the North Tower
(34:03) Fear takes over in the stairwell
(1:04:01) Turning tragedy into a new career
(1:28:02) Challenging attitudes about blindness
(1:38:01) Supporting guide dog organizations
🔗 RESOURCES MENTIONED
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Q&A: My Dream Job Won't Wait If I Take a Family Gap Year — Do I Quit Anyway?
#748: The real question behind quitting a job you love or paying off debt anyway? Your money mindset. Take our free quiz to find yours: https://affordanything.com/fiire A listener with $686,000 saved and a job …
Notas do episódio
#748: The real question behind quitting a job you love or paying off debt anyway? Your money mindset. Take our free quiz to find yours: https://affordanything.com/fiire
A listener with $686,000 saved and a job she loves wants to take her family on a year-long trip — but Paula says her real question isn't about money at all. Later: a dad chooses to stop maxing his IRA to pay off a mortgage, even though the math says otherwise.
Joe joins from the road to help answer three listener questions: a family weighing a year off against a job she loves, a dad debating whether to stop maxing his IRA to pay off a house, and a longtime listener with a smarter way to save for college.
In this episode, we discuss:
- How to decide whether a job you love is worth walking away from for a family gap year
- The three factors that actually predict whether you'll love your next job
- Why "retiring early" might be the wrong goal — and what to aim for instead
- How to know if you're financially ready for a career break, and what to prep first
- Why paying off your mortgage can beat investing, even when the math says otherwise
- How to structure your mortgage term like a finance pro (and why the 30-year can win)
- Why saving in separate, labeled accounts makes it easier to actually hit your goals
Whether you're weighing a big life pivot, deciding what to do with extra cash, or just trying to make saving feel less abstract, this episode offers frameworks — not just formulas — for making the call.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(07:12) Can you afford to quit a job you love?
(11:09) Three things that actually predict job satisfaction
(17:05) Why this window with your kids won't come twice
(22:20) Why retiring often beats retiring early
(30:14) Why bad trip experiences count as good data
(34:18) Why paying off debt can beat the math
(36:49) Why coasting on your current savings pace is risky
(44:26) How to think like a CFO about your mortgage
(51:09) Why one bucket per goal makes saving easier
(53:46) Why your 401k isn't really about retirement
🔗 OTHER RESOURCES
👉 The real question behind quitting a job you love or paying off debt anyway? Your money mindset. Take our free quiz to find yours: https://affordanything.com/fiire
👉 Camp Fi, the financial independence retreats Paula and Joe swap stories about this episode: https://campfi.org
👉 Heavy Metal Money, Chris Luger's personal-finance podcast (Joe recorded this episode from his place): https://heavymetal.money
👉 Got a question of your own? Leave a voicemail for Paula: https://affordanything.com/voicemail
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
First Friday: Trouble in the Bond Market
#747: We have good news on multiple fronts to share about the job market, the stock market, the commodities market, and volatile news around the bond market. And we begin it with some great news coming out of …
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#747: We have good news on multiple fronts to share about the job market, the stock market, the commodities market, and volatile news around the bond market.
And we begin it with some great news coming out of Nepal.
Welcome to the First Friday episode for September 2026.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(00:00) Rescued workers in Nepal
(04:53) Strong August jobs report
(10:14) Conflicting employment data
(12:27) Strong jobs, weaker stocks
(17:43) Why bonds matter more
(23:17) Inflation drives Treasury yields
(29:45) Hidden risks in bonds
(36:50) Treasury buyback controversy
(43:32) Liquidity versus warning signs
🔗 RESOURCES MENTIONED
👉 Build a Life of Financial Freedom with our free workbook: https://affordanything.com/fiire
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Q&A: What Nepal Reveals About Wealth and Safety
#746: We begin today’s episode with a discussion of the disastrous flash flooding in Nepal, a personal topic for Paula given her family there. There’s both a human story, one of the resilience of the Nepalese …
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#746: We begin today’s episode with a discussion of the disastrous flash flooding in Nepal, a personal topic for Paula given her family there. There’s both a human story, one of the resilience of the Nepalese people and the strong community bonds there, and an economic story, where poor infrastructure and a lack of economic development have hindered disaster response and exacerbated the tragedies of recent events.
Listeners can donate to help the victims here:
The Prime Minister Relief Fund: https://pmdrf.nchl.com.np/
Caritas Nepal: https://www.caritasnepal.org/donate-now/
Learn more about the ongoing rescue efforts at https://help.ekantipur.com/
A caller wants to put part of her mom's $80,000 home-sale proceeds into an annuity — and it left her financial-planner co-host doing a double take. Turns out it might be the first caller in the show's history the product was actually built for.
This week's Q&A tackles two retirement questions from listeners: when it makes sense to ease off maxing out a 401k in favor of a more flexible brokerage account, and whether a guaranteed-income annuity is the right move for a retiree who isn't great at managing money on her own.
In this episode, we discuss:
How to know when to stop maxing out your 401k and start filling a taxable brokerage account instead
The real "deal" you're making with the government every time you use a tax-advantaged account
Why an insurance company can keep 100% of the money if the annuity holder dies too soon — and how to avoid it
The one type of person a guaranteed-income annuity is actually built for
A simple daily habit trick for building consistency, borrowed from a world-class choreographer
Why doing everything right doesn't guarantee a good outcome, and what that means for your own decisions
What Nepal's disaster response reveals about the real payoff of economic development
Whether you're mapping out an early-retirement bridge or helping a parent build guardrails around a windfall, this episode will help you think more clearly about the trade-offs each option carries.
🔗 RESOURCES MENTIONED👉 Not sure which investments belong in your 401k, your Roth, or your taxable account? Grab our free guide to figuring out where each one goes: https://affordanything.com/assetlocation
👉 Morgan Housel on the split-second decision that changed everything: https://affordanything.com/488-gut-instincts-and-big-decisions-with-morgan-housel/
👉 Our interview with retirement researcher Dr. Wade Pfau on annuities and retirement income: https://affordanything.com/271-retirement-planning-in-2020-with-dr-wade-pfau/
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The Four Kinds of Rich Nobody Counts -- with Sahil Bloom [GREATEST HITS]
#745: A friend once asked Sahil Bloom how often he saw his parents. About once a year, Sahil said. How old are they? Mid-60s. His friend did the math out loud. If they live to 80, you'll see them 15 more times …
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#745: A friend once asked Sahil Bloom how often he saw his parents. About once a year, Sahil said.
How old are they? Mid-60s.
His friend did the math out loud. If they live to 80, you'll see them 15 more times.
Sahil was 30, living in California and making great money at a venture fund. Within 45 days of that conversation, he quit his job, sold his house and moved across the country to be near family.
He's now managing partner of SRB Ventures, an early-stage fund backing more than 60 startups, and he writes The Curiosity Chronicle, a newsletter read by millions. His book, "The 5 Types of Wealth," is a New York Times bestseller.
His framework starts with a scoring problem. Financial wealth gets measured every day. Time, social, mental and physical wealth run in the background, unmeasured, until something forces you to look.
You'll get exercises for each. Build an energy calendar that tracks which activities charge you up and which drain you.
Map your relationships by how healthy and how frequent they are. Ask what your family and your community need from you. Define what "enough" means in dollars, then write the number down.
Sahil also walks through anti-goals — the things you refuse to sacrifice on the way to a goal — and Memento Mori, the Roman habit of keeping your own death in view.
Two questions run underneath all of it. Think about how you spent yesterday. Would your 10-year-old self be impressed? Would your 90-year-old self?
You don't experience all four seasons in a single day. Sahil argues your life runs on seasons too. Some stretches call for financial growth. Others call for family.
Find Sahil at the5typesofwealth.com.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
This Historian Says We're Living in the Best Era Ever, with Joseph Moore
#744: With about $200 and a crypto exchange, historian Joseph Moore turned himself into a legitimate billionaire — a stunt that says more about how money actually works than most financial advice does. It's …
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#744: With about $200 and a crypto exchange, historian Joseph Moore turned himself into a legitimate billionaire — a stunt that says more about how money actually works than most financial advice does. It's also a preview of the 300-year argument he makes in this episode: that almost everything we're told about money is newer, and far less permanent, than we think.Joseph Moore, PhD, is a historian and the national bestselling author of How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn't). His own self-experiments with historical money strategies helped him become financially independent in his mid-40s.
In this episode, we discuss:
- How "never save your money" used to be completely reasonable financial advice
- Why bonds quietly beat stocks for nearly all of the 1800s
- How to spot when today's "obvious" financial rules are about to expire
- Why real estate booms always show up right alongside inflation spikes
- Why young people's unemployment is outpacing everyone else's — and what history says to do about it
- Why economic optimism and economic data have stopped matching up
- Why building more housing is the only housing-crisis fix that's ever actually worked
This one's for anyone who feels like the rules of money keep changing under them — because they do, and always have. Understanding that pattern is the first step to building wealth in whatever era you happen to be living in.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(05:18) How a runaway slave built his own legal currency
(06:52) How he legally declared himself a crypto billionaire
(13:22) Why a fifth of the Smithsonian's money collection is fake
(15:52) The bestselling book that told readers to commit fraud
(20:10) The decades when bonds quietly beat stocks
(26:04) How his grandfather secretly became a bond millionaire
(31:09) Why that "$10K in 1929" chart is misleading
(48:02) Why wages are up 50% and nobody believes it
(1:06:39) Why most Americans once owned one shirt
(1:23:48) The rent control law that backfired for renters
🔗 RESOURCES MENTIONED
👉 Build a Life of Financial Freedom with our free workbook: https://affordanything.com/fiire
👉 Joseph Moore's site — his book, essays, and more: https://www.josephmoorebooks.com
👉 Your Money or Your Life by Vicki Robin & Joe Dominguez: https://vickirobin.com/your-money-or-your-life/
👉 The Latte Factor by David Bach: https://www.simonandschuster.com/books/The-Latte-Factor/David-Bach/9781982120245
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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 …
Notas do episódio
#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 Mimetic Desire in Everyday Life. He returns to the show to talk about his new book, The One and the Ninety-Nine.
In this episode, we discuss:
- Why having too much easy community can be just as damaging as having none at all
- How to tell whether your beliefs are actually yours — or something you inherited without ever examining it
- Why cutting people off has quietly become the default response to conflict
- How to stop shrinking yourself just to keep other people comfortable
- The zero-tolerance rule Luke enforces at his own company to kill passive-aggressiveness before it starts
- How Luke actually decides who to trust, hire, and build relationships with
- What an existential crisis at 29 — and five humbling years training for the priesthood — taught a successful entrepreneur about identity
This episode is for anyone who feels the pull between fitting in and standing out — in your family, your workplace, or your online life. Luke offers a way to build an identity solid enough to hold up under pressure, without giving up on real community.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(7:42) Two competing drives wired into every human being
(10:11) Why group pressure breaks some people and not others
(17:39) Why cutting people off replaced working through conflict
(19:39) The real number of close friends you actually need
(26:51) Where your beliefs actually came from
(32:00) You're not responsible for how someone else feels
(36:09) The zero-tolerance workplace rule against passive-aggressiveness
(41:22) How to actually tell who you can trust
(53:33) The existential crisis that sent an entrepreneur toward the seminary
(55:39) The humbling lesson hidden in a vending machine
🔗 RESOURCES MENTIONED
👉 This free 10-day workbook helps you trace your money habits back to whether they're actually yours — starting with your own money mindset — https://affordanything.com/fiire👉 Luke's website (books, newsletter, and more) — https://lukeburgis.com
👉 Luke's new book, The One and the Ninety-Nine: Forging Identity in the Age of Social Contagion — https://www.amazon.com/One-Ninety-Nine-Forging-Identity-Contagion/dp/1250373034
👉 Paul Graham's essay "Cities and Ambition," on how the place you live shapes what you want — https://paulgraham.com/cities.html
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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 …
Notas do episódio
#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 questions: hiring your first accountant amid a complicated tax situation, whether to pay off a mortgage or retire early once you've already hit your number, and why one half of the show won't touch a popular alternative investing strategy.
In this episode, we discuss:
- How to tell the difference between a CPA, an EA, and a tax attorney — and which one you actually need
- Why software can't keep up once your tax situation gets complicated
- How to interview and choose an accountant with confidence
- How to know if "one more year" at work is a smart plan or a sign of fear
- Why loving your job can change the entire math on early retirement
- Why a former financial planner still won't recommend risk parity investing
- What four well-known investing philosophies get right — and where they disagree
Whether you're hiring your first accountant, staring down an early retirement decision, or trying to make sense of competing investment philosophies, this episode will help you separate genuine progress from comfortable procrastination.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(04:02) Why software can't handle a messy tax situation
(08:02) The three types of tax pros — and who you actually need
(12:46) How to interview and choose the right accountant
(24:42) She hit her $1.4M goal three years early
(32:22) The hidden fear behind "one more year" at work
(38:29) Why loving your job changes the retirement math
(49:39) Why a former advisor won't touch risk parity
(53:46) Four investing legends who all disagree with each other
(59:35) The historian's warning: history doesn't repeat itself
(1:07:57) The cooking analogy that explains your portfolio
🔗 RESOURCES MENTIONED
👉 Not sure which investments belong in your Roth vs. your taxable account? Grab our free one-page guide to where each type of investment should sit: https://affordanything.com/assetlocation
Karsten Jeske ("Big ERN"):
👉 "How to Lie with Personal Finance – Part 4: Risk Parity": https://earlyretirementnow.com/2026/07/29/risk-parity-lies/
👉 "Can We Increase the Safe Withdrawal Rate with Risk Parity? – SWR Series Part 64": https://earlyretirementnow.com/2026/07/27/risk-parity-swr-series-part-64/
👉 #548: Is Your Retirement Safe in Today's Economy?: https://affordanything.com/548-is-your-retirement-safe-in-todays-economy-with-dr-karsten-jeske-big-ern/
👉 #643: LIVESTREAM: A Former Fed Economist Reveals What's Really Happening: https://affordanything.com/643-livestream-a-former-fed-economist-reveals-whats-really-happening-with-karsten-jeske-big-ern/
Nick Maggiulli:
👉 #375: The 2X Rule (and Other Wealth-Accelerating Advice): https://affordanything.com/375-the-2x-rule-and-other-wealth-accelerating-advice-with-nick-maggiulli/
👉 #629: The Wealth Ladder Has Six Rungs (and Most People Never Climb Past Four): https://affordanything.com/629-nick-maggiulli-the-wealth-ladder-has-six-rungs-and-most-people-never-climb-past-four/
Frank Vasquez:
👉 #618: How to Retire at 50 While Supporting Aging Parents: https://affordanything.com/618-how-to-retire-at-50-while-supporting-aging-parents-with-frank-vasquez/
👉 His podcast, Risk Parity Radio: https://www.riskparityradio.com
JL Collins:
👉 #624: JL Collins Part 1 – The Simple Path vs. The "Optimal" Path: https://affordanything.com/624-jl-collins-part-1-the-simple-path-vs-the-optimal-path/
👉 #625: JL Collins Part 2 – What Happens When You Don't Need to Work Anymore?: https://affordanything.com/625-jl-collins-part-2-what-happens-when-you-dont-need-to-work-anymore/
Paul Merriman:
👉 #550: Paul Merriman – The 4-Fund Strategy That Beats the S&P 500: https://affordanything.com/550-paul-merriman-the-4-fund-strategy-that-beats-the-sp-500/
👉 #590: Small Cap Showdown! Paul Merriman vs. Dr. Karsten Jeske: https://affordanything.com/affordanything-com-small-cap-value-debate/
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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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 …
Notas do episódio
#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 choice, not a trap
How to tell if you're staying in a job for the right reasons, or just fear
Why the same decision can be exactly right at 24 and wrong at 34
What actually helps when comparison and "falling behind" turn into apathy
How he turned $6,000 into $400,000 trading a stock bubble, then gave much of it back
Why hitting your number rarely feels like the finish line people expect
Two questions worth asking before you spend years on something that isn't working
This one's for anyone who feels behind, stuck, or unsure if their current path is a smart trade-off or just fear in disguise — Jack's way of thinking about money and time might be the reset you need.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(02:00) He liked his boss on a dating app
(06:57) Two very different ways to spend your twenties
(17:56) Why grad school became his built-in sabbatical
(19:16) Why 30 gets judged harder than 24
(34:12) The real cause of career apathy
(39:20) His best fix for feeling stuck
(46:27) Same decision, right at 24, wrong at 34
(01:01:43) What's really keeping you in a job you hate
(01:14:12) Why more money doesn't fix stress
(01:17:56) Turning $6,000 into $400,000 in a stock bubble
🔗 RESOURCES MENTIONED
👉 Take the free 10-day FiiRE money-mindset workbook: if "I make too much to quit" sounds familiar, this helps you find out if that's actually true. → https://affordanything.com/fiire
👉 Jack's new book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties → https://jackraines.blog/book
👉 Nick Maggiulli's The Wealth Ladder, the six-level wealth framework Paula references → https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039
👉 Freedom, the app Jack and Paula both use to block social media and protect focus time → https://freedom.to
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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 …
Notas do episódio
#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, we discuss:
- How to build a bucket strategy so you can retire early and still stay aggressive with your portfolio
- The real markers that tell you it's time to go back to work — not just a number
- How one listener turned a marketplace side hustle into a $5,500 day
- When to leave a stable paycheck for a growing side business, and when to wait
- Why a popular plan to gift a winning stock to your kids usually backfires
- Whether it's worth paying taxes now to raise your stock's cost basis
- Where a single winning stock belongs — taxable, Roth, or a solo 401(k)
Whether you're weighing an early exit from a stable career, deciding if your side hustle is ready to become your main hustle, or holding a stock that's grown far beyond what you expected, this episode will help you think through the tradeoffs before you act.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(00:00) Why a winning stock can turn into a tax trap
(02:23) A $1.2M portfolio and a plan to retire by 45
(07:45) Why an aggressive portfolio needs a cash cushion first
(16:49) The real signal your plan isn't working
(24:25) A side hustle that made $5,500 in one day
(33:51) Quit now or wait — two strong arguments
(39:51) The book that could save a new business
(54:09) A $200 stock that grew into $25,000
(01:01:08) The tax rule that blocks gifting stock to your kids
(01:12:59) A hidden tax that kicks in above $250,000 income
🔗 RESOURCES MENTIONED
👉 Grab the free Asset Location Made Simple guide to see exactly which investments belong in your taxable, Roth, and pre-tax accounts: https://affordanything.com/assetlocation
👉 Frank Vasquez's risk parity portfolio, explained in depth on episode #618: https://affordanything.com/episode618
👉 Profit First by Mike Michalowicz, the book Joe recommends for setting up your business finances the right way from day one: https://amzn.to/3Sf7Tpo
👉 Julie Wainwright's interview on the Stacking Benjamins podcast, on rebuilding after Pets.com to found The RealReal: https://www.stackingbenjamins.com/from-business-idea-to-execution-julie-wainwright-1703
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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 …
Notas do episódio
#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 that seems to contradict itself
- What actually happens when you buy a 30-year Treasury bond
- Why bond yields hitting a two-decade high matters for your money
- Why mortgage rates are climbing again, and what that means for housing
- Why home prices are surging in some states while crashing in others
- Why gold is quietly staging a comeback
- What the new government-seeded kids' accounts actually do
Whether you're deciding where your next dollar should go, watching mortgage rates before a purchase, or wondering if your kid needs a new account this year, this episode gives you the full economic picture in one sitting.
⏱️ TIMESTAMPS
Note: Timestamps may vary slightly depending on dynamic ad placements.
(00:00) Why the jobs report shocked economists this month
(03:24) How jobs can drop while unemployment drops too
(08:03) Why Paula just bought her first bond ever
(09:35) A crash course on why bond yields are spiking
(25:34) Why unemployment claims just hit a 55-year low
(27:57) Why young job seekers have it harder than everyone else
(35:23) Why mortgage rates just hit a one-year high
(51:28) Why gold is rebounding, and who's buying it
(57:47) What the new 530A investment accounts mean for your kids
🔗 RESOURCES MENTIONED
👉 Wondering which account should actually hold that bond (or gold, or index fund) you just bought? Grab our free cheat sheet showing exactly where each investment belongs: https://affordanything.com/assetlocation
👉 Chat about this episode with the community: affordanything.com/community
👉 TreasuryDirect, where Paula opened her account to buy the bond: treasurydirect.gov
👉 CME FedWatch Tool, for tracking the market's odds of a September rate hike: https://www.cmegroup.com/markets/interest-rates/cme-fedwatch-tool.html
Learn more about your ad choices. Visit podcastchoices.com/adchoices
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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 …
Notas do episódio
#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, originally released in June 2025, in honor of his sudden passing this year and the practical security knowledge he left behind.
In this episode, we discuss:
-How to spot a phishing scam before you click the link
-Why turning on two-factor authentication blocks almost every account takeover
-The simple bank alert setting that can stop a fraudulent transfer
-Why cybersecurity experts sometimes recommend paying a ransomware demand
-How AI-cloned voices are powering a new wave of grandparent scams
-What your phone's app permissions reveal about who's tracking you
-Why "it won't happen to me" is exactly what scammers count on
This episode is for anyone who assumes hackers only go after big companies — because the reality is scammers are counting on you to think that. You'll walk away with concrete, five-minute changes that close the gaps most people don't know they have.
⏱️ TIMESTAMPSNote: Timestamps may vary slightly depending on dynamic ad placements.
(03:41) Why you're an easier target than a big bank
(06:46) Why cryptocurrency theft is nearly impossible to reverse
(10:59) How one password can move half your savings
(17:35) The fake unpaid-toll text that's made scammers millions
(21:55) Why paying the ransom is sometimes the smart move
(29:05) How AI clones your kid's voice for scams
(37:58) The one thing to never hand a child
(54:57) Why you should mask your location online
(01:16:18) The setting that blocks almost every account hack
(01:18:45) The bank alert that can undo fraud fast
🔗 RESOURCES MENTIONED
👉 See your full financial picture — income, debt, safeguards, and goals — in one place with our free one-page worksheet: https://affordanything.com/cornerstone
👉 Dr. Eric Cole's firm, Secure Anchor Consulting: secure-anchor.com
👉 Signal, the encrypted messaging app Dr. Cole recommends for sensitive conversations: https://signal.org
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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Aqui estão os 40 episódios mais recentes de 813. Os mais antigos estão no feed do podcast.
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