Afford Anything | Get Smarter With Money

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.

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.

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

(02:39) How fear cost him a decade of investing

(04:44) Why money feels more taboo than sex

(11:12) Why saving 13 cents beats saving nothing

(13:54) Why people feel broke during a long bull market

(17:48) Same $10,000, different app, different behavior

(22:54) Why the best investing is boring

(28:49) Patience vs. prediction: how wealth really grows

(46:48) When his body forced him to stop working

(54:20) Living with the odds that most businesses fail

🔗 RESOURCES MENTIONED

👉 AVOIDING YOUR MONEY COST HIM A DECADE. FIND OUT IF YOU'RE AN AVOIDER TOO: https://affordanything.com/fiire

👉 Noah Kerner: https://www.acorns.com/noah

👉 Acorns: https://www.acorns.com

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

#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.

#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.

#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 https://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.

#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 https://podcastchoices.com/adchoices

#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 https://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.

#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 https://podcastchoices.com/adchoices

#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 https://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.

#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 https://podcastchoices.com/adchoices

#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 https://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.

#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 https://podcastchoices.com/adchoices

#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 https://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.

#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 https://podcastchoices.com/adchoices

#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 https://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.

#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 https://podcastchoices.com/adchoices

#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: https://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 https://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.

#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: https://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 https://podcastchoices.com/adchoices

#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.

⏱️ TIMESTAMPS

Note: 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 https://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.