812 episodes
The 5 Levels of Investors, and Why Some People Never Leave Level One, with David Leiter
10/11/2026 | 1h 13 mins.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.- 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?
03/11/2026 | 1h 12 mins.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.
👉 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. - 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.
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About Afford Anything | Get Smarter With Money
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.
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