#663: We’re living through the first era in which an investor can ask a machine to read a decade of SEC filings in seconds. That sounds powerful, but also a little terrifying. Can we trust it? And how do we use it without falling for hallucinations or built-in optimism?

In this episode, we dig into the practical, real-world ways AI can strengthen our investing process while avoiding its biggest pitfalls. If you’ve ever wondered how to blend old-school fundamentals with new-school tools, this conversation will open up an entirely new mental model.

Our guest is Brian Feroldi, an investor who has spent more than twenty years doing classic, deep-dive fundamental research. He reads SEC filings for fun, and he’s embraced AI not as a stock picker, but as a force multiplier that can turn days of research into minutes.

We talk about the specific guardrails that make AI useful for fundamental investors, including restricting sources to trusted filings, designing step-by-step instructions, and assigning the AI a role so it knows how to “think.” We also explore how to stress-test optimism bias, how to analyze companies like a forensic accountant or a short seller, and how to build prompts that match your own investing personality.

Whether you’re an index-fund loyalist with a little “fun money” or a hands-on analyst, this conversation will expand the way you evaluate businesses and make decisions.

Key Takeaways

Resources and Links

Chapters

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(03:02) Pros and cons of using AI for stock research


(4:55) Why Brian invests heavily in individual stocks


(12:52) Guardrails for reducing AI hallucinations


(17:22) How to write step-by-step prompts


(24:02) Using roles to shape AI’s output


(35:57) Running Brian’s prompt on Kava


(46:22) Understanding pricing power and recession behavior


(01:00:02) Evaluating management teams


(01:06:02) Using AI to reflect your investing personality

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#662: Most teams hire for skills. The best teams hire for wiring.

What if the reason someone accelerates your organization, or quietly derails it, has more to do with their response time, processing style, or sense of mission than their résumé?

This episode dives into the hidden patterns that shape how people work, make decisions, and handle pressure; the clues we often overlook, and the tiny tells that reveal who will thrive.

We’re joined by William Vanderbloemen, whose firm has completed nearly 4,000 executive searches.

After reviewing years of candidate data, he discovered why some people create momentum everywhere they go and others struggle, even when they look perfect on paper.

We explore what “fast thinkers” and “slow thinkers” bring to a team, how to spot agility before you hire someone, and why some workers need a mission while others need a measurable win.

Along the way, we reflect on our own tendencies and how understanding them can change the way we build teams, manage energy, and make long-term decisions.

Key Takeaways

Response speed can signal mental wiring, not politeness, which makes it a powerful hiring clue.

The real interview starts long before the formal meeting, which means every informal interaction counts.

Agility shows up when plans change, so micro-tests can reveal how someone handles shifting conditions.

Many high performers are driven either by purpose or measurable progress, and knowing which matters.

Understanding our own lane helps us hire better, delegate better, and build systems that reduce friction.

Resources and Links

Simon Sinek, Start With Why https://www.youtube.com/watch?v=u4ZoJKF_VuA

Vanderbloemen Group https://vanderbloemengroup.com/

Be the Unicorn by William Vanderbloemen https://www.amazon.com/Be-Unicorn-Data-Driven-Separate-Leaders/dp/1400247101

Chapters

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(00:00) What thousands of executive searches revealed

(10:35) The nine markers of high performers

(22:01) Fast thinkers, slow thinkers, and finding your lane

(25:35) Why response time predicts performance

(25:48) Testing agility in real-world scenarios

(47:16) Why purpose matters more to younger workers

(55:13) Why curiosity is a career superpower

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#661: When your income drops, debt spikes, and a rental property starts bleeding cash, it can feel like your entire financial foundation is cracking beneath you. Veronica, our first caller, is navigating all of it at once, from a near-foreclosure to a luxury car payment that’s strangling her budget. Her question is simple but enormous, how do you rebuild when you’re overwhelmed and out of margin?

Once we work through her path forward, we shift to a listener on the opposite end of the spectrum. Daniel has maxed his Roth IRA, HSA, 401(k), and 457, and now sits on growing surplus cash. We talk about where extra money belongs when you’re aiming for early retirement and wondering whether to invest, save, or crush a low-interest mortgage.

And to close, we take on a question dominating every financial feed right now, what if AI stocks really are in a bubble? We break down what it means to short the market, whether put options are actually a “safe” bet, and how to position a portfolio if you’re worried about tech valuations.

Listener Questions in This Episode

Key Takeaways

Resources and Links

Chapters

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(0:00) Veronica’s debt crisis and rental challenges

(16:46) Cutting car costs and rebuilding cash flow

(22:28) Debt relief programs and avoiding bad actors

(28:17) Daniel’s surplus cash and retirement strategy

(37:52) Brokerage vs mortgage payoff discussion

(49:20) Can you profit from an AI bubble burst

(1:00:40) Why shorting and puts rarely pay off

(1:08:18) Safer ways to position your portfolio

Got a question: Call it in: https://affordanything.com/voicemail

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#660: Caring for an aging parent can morph into a second full-time job, and even the most financially savvy adults get blindsided. Bank accounts freeze, home sales stall, and family savings disappear faster than anyone expects.

In this episode, we dig into what really happens when you take over a parent’s financial life, from the first power of attorney to the final tax return.

We explore the emotional and logistical realities of dementia care, Medicaid, trusts, probate, and why a single smartphone setting can determine whether you can access the information you need.

Veteran financial journalist and certified financial planner Beth Pinsker joins us to share the hard lessons she learned while managing her parents’ money, housing, and estate. She opens up about the “you don’t know what you don’t know” moments that hit even experts.

We look at why almost every caregiver reaches a breaking point, the two documents that can save a year of stress and tens of thousands of dollars, how a forgotten zero-balance home equity line nearly torpedoed a real estate deal, and why phone access now belongs at the center of estate planning.

We also confront the brutal math of long-term dementia care, the real differences between Medicare and Medicaid, how to evaluate facilities beyond brochures, and what happens when a parent dies without updated paperwork. Through it all, we focus on how clear conversations about wishes and values can reduce guilt and burnout for the people left steering the ship.

Key Takeaways

Key moments

(0:00) Why financial caregiving blindsides even the experts

(05:18) The hidden home equity line that almost killed a real estate deal

(10:54) Two documents every adult in your life should have

(14:29) The critical phone setting that protects access to accounts and memories

(21:23) What Prince’s estate taught us about wills and inertia

(31:39) Planning for a decade of dementia care without going broke

(35:16) How Medicaid really works and why “running out of money” is a process

(38:46) The menu of care options from in-home help to CCRCs and nursing homes

(44:31) The “smell test” for evaluating facilities in the real world

(51:06) What to do in the first weeks after a parent dies

(54:38) Trusts, titles, probate, and how one frozen account cost $5,000 to unlock

(01:01:04) Knowing their wishes so money decisions feel like honoring, not guessing

Resources and Links

Share this episode with a friend, colleagues, and anyone who is thinking about caregiving: https://affordanything.com/episode660

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#659: Imagine that you’re at the absolute peak of your career. You’re the CEO of a prominent advertising company at the age of 36, but you feel like you’re driving in the wrong lane. It’s wrong.Then you make a hard career pivot and it works out beautifully.My guests today know exactly what that’s like. We’re joined by James Patterson, the author who has sold more than 425 million copies of his books. He has co-authored books with President Clinton, Dolly Parton, and now his latest co-author is Dr. Patrick Leddin, who also joins us to talk about disruption.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(0:00) Defining disruption versus gradual change

(5:20) Positive disruption mindset and overcoming fear

(8:12) Process for uncovering personal passions

(10:25) Patterson disrupts publishing with six books per year

(13:45) Research reveals 16 disruptive behaviors

(16:30) Academia embracing different voices and perspectives

(21:00) Mountain climber story shows gradual disruption

(24:14) Framework for navigating career transitions

(28:19) Limiting beliefs and psychological barriers

(30:55) Being open to change versus stability

(35:00) Taking ownership of disruptive choices

(41:00) Mission versus purpose distinction

(46:37) Advice for embracing positive disruption

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#658: An unusual First Friday episode because we don't have a jobs report.

However, we do know that in October, U.S. companies announced more job cuts in a single month than they have over any single month of the last 20 years. In other words, October was peak job cut month.

By contrast, private payrolls, as reported by ADP, rose by 42,000 in October, so we have a little bit of conflicting data. Some pessimistic, some optimistic. We're going to take a deeper look at that in today's episode.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) Conflicting Job Market Data

(03:40) Youth Unemployment and AI’s Impact

(10:16) Fed Rate Cuts and Housing Market

(20:23) New Job Postings Lowest in 4 Years

(20:54) Consumer Sentiment

(22:04) Social Security Payments Increase in 2026

(23:33) Rising Car Costs and Repossessions

(24:46) Good News for Prescription Drug Prices

(31:50) Government Shutdown Impacts

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#657: This week, Paula and Joe dig into a listener’s question about ETFs that track the stock trades of U.S. politicians — including the Democratic “NANC” fund and its Republican counterpart “KRUZ.” They explore whether this strategy is smart investing or just expensive entertainment.

Then, they shift gears to home ownership headaches. Another listener asks how to control ballooning maintenance costs, and Paula shares her best advice for finding trustworthy contractors, budgeting for repairs, and knowing when DIY doesn’t actually save money.

Finally, an anonymous caller wonders if starting a small business just for tax breaks makes sense. Paula and Joe explain the IRS rules — and why energy and purpose matter more than deductions.

From “fun money” investing to financial planning that actually works, this episode is all about balancing curiosity, caution, and common sense.

Key Takeaways

Chapters

Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) Should You Follow Congress’s Trades?

(06:00) The Lag Problem and Investor Bias

(10:30) The “Fun Money” Rule

(11:20) The Hidden Cost of Home Repairs

(15:00) Finding Investor-Friendly Contractors

(18:00) Planning Ahead for Repairs

(22:00) DIY vs. Opportunity Cost

(26:00) Starting a Small Business for Tax Breaks

(29:00) The IRS “3-of-5 Rule”

(32:00) Purpose Over Deductions

(34:00) Final Thoughts

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#656: What would you do if someone in authority told you to do something that felt wrong? Most of us like to think we'd speak up, push back, stand our ground. But research tells a very different story.

In fact, when Yale researchers conducted a famous experiment in the 1960s, they found that 65% of people would administer what they believed to be deadly electric shocks to another human being... simply because someone in a lab coat told them to.

Today's guest has spent over 15 years studying why humans comply with authority - even when every fiber of our being is screaming that we shouldn't. And when it comes to our money, this tendency to comply with authority figures - from financial advisors to real estate agents to car salespeople - can cost us dearly.

Dr. Sunita Sah began her career as a physician in the UK's National Health Service. During one particularly exhausting period as a junior doctor, she agreed to meet with a financial advisor who had contacted her at work. That meeting sparked questions that would shape the rest of her career: Why did she feel pressured to trust this advisor, even after learning he had a conflict of interest?

Today, she's a tenured professor at Cornell University, where her groundbreaking research on compliance and influence has been featured in The New York Times and Scientific American. She's advised government agencies, served on the National Commission on Forensic Science, and helps leaders understand the psychology behind why we say "yes" when we really want to say "no."

Whether you're meeting with a financial advisor, negotiating the price of a home, or discussing rates with a contractor, understanding the psychology of compliance could save you thousands of dollars - and help you make better financial decisions. Today's conversation isn't just about psychology - it's about protecting your wealth by learning when and how to say "no."

Resources Mentioned in the Episode:

- Website: sunitasah.com

- Newsletter: Defiant By Design | Dr. Sunita Sah | Substack

- Connect with Dr. Sunita Sah

- Follow Dr. Sah on Instagram

About Dr. Sunita Sah

Dr. Sunita Sah is a tenured professor at Cornell University specializing in organizational psychology. Her research focuses on how and why people comply with authority, even against their better judgment. A former physician in the UK's National Health Service, Dr. Sah brings a unique perspective to understanding human behavior and decision-making. Her work has been featured in leading publications including The New York Times and Scientific American, and she has served as a Commissioner on the National Commission on Forensic Science.

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#655: What would you do if, at the age of 23, you found yourself with $70,000 a year leftover after expenses? Would you pour everything into retirement and coast to financial independence, or stockpile a down payment before life gets pricier with kids, a mortgage, and maintenance costs?

This week, we dive into that real-life dilemma and explore how to strike the perfect balance between freedom now and security later.

Along the way, we question whether a 0.40% fee for automated tax-loss harvesting is really worth it, and debate if the rise of mega-corporations means small-cap value investing is dead.

Listener Questions in This Episode

Key Takeaways

Chapters

Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) Are we headed for a dystopian future

(01:48) A 23-year-old with a $125k income and a big savings gap

08:52) House price, down payment size, and the numbers that drive the split

(10:47) The savings snowball case, match protection, and timeline trade-offs

(25:14) Where to park the down payment, why cash beats stocks for readiness

(32:31) Is 0.40 percent worth it for tax-loss harvesting

(36:24) Fees versus claimed tax savings, turnover, and exit options

(50:51) Should dystopia change our portfolio

(54:36) Small-cap value beyond tech, acquisitions, and global opportunity

(1:11:02) Optimism, innovation, and why investing still assumes progress

P.S. Got a question? Leave it at https://affordanything.com/voicemail

For more information, visit the show notes at https://affordanything.com/episode655

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#654: Fights about money are common, but they're rarely about math. They're about power, shame, vulnerability, and trust. And no amount of data or fancy spreadsheets is going to fix it. What you need is a better system for fairness, more open communication, and a shared ambition.

In this candid conversation with Heather and Doug Bonaparte, we explore how two partners rebuilt confidence, handled their six-figure student loans, and designed a rhythm for money talks that actually works.

Together they share how early money stories, law school debt, and the Great Recession shaped their dynamic, plus the tools they used to find fairness at home and in their finances

Key Takeaways

Resources and Links

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