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#717: Clare Flynn Levy was a hedge fund manager in London in the summer of 2007, watching her trading screens turn red — every single day. Merger arbitrage spreads were widening. Investors were pulling out. She didn't yet realize she was watching the early tremors of a global financial crisis.

Clare joins us to talk about what that experience taught her about investor behavior, emotional bias, and the hidden forces that drive financial decisions.

She now runs a firm that helps professional fund managers analyze their own decision-making patterns. Her core argument: most investors aren't making rational choices. They're rationalizing them.

We get into two specific biases that cloud judgment — sunk cost fallacy and the endowment effect — and how they show up whether you're picking individual stocks or rebalancing a 529 plan.

Clare shares a personal example. After the 2024 election, she moved her kids' college funds from equities into bonds, recorded her reasoning in her calendar, and came back nine months later to review it honestly. She was wrong. Equities kept climbing. But having a written thesis let her make a clean new decision rather than doubling down out of ego.

We also walk through five investor archetypes drawn from behavioral research on fund managers. Connoisseurs let winners run. Raiders take profits too early. Rabbits freeze — or keep buying into a losing position. Hunters wait and take calculated shots. Assassins cut losses cleanly, without emotion.

Most people default to rabbit behavior when things go south. The goal is to be an assassin. Clare's practical rule: don't let any single position drag your overall portfolio down more than 1 percent before forcing yourself to reassess.

Her closing advice for long-term investors: ask yourself five simple questions before every major move, write down your reasoning, and go back and check.

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.

(00:00) 5 Ways Investors Behave When Things Go Wrong

(05:20) Clare Flynn Levy — hedge fund manager turned behavioral finance analyst

(06:50) 2008 crisis — watching screens turn red daily

(08:25) Sunk cost fallacy and the endowment effect — why investors hold losers too long

(10:25) Index funds — riskier than most people think

(17:09) Tech concentration — how indexes got warped

(27:52) Algorithmic trading — machines changing the game

(29:37) Playing the wrong game — taking cues from short-term traders

(31:22) Individual stocks — same behavioral traps apply

(35:22) Hit rate vs. payoff ratio — what actually drives returns

(44:57) Five investor archetypes — how you behave when winning and losing

(50:17) Alpha decay — when to exit a winning position

(54:22) Being an assassin — rules for cutting losses without emotion

(59:42) Decision journaling — five questions to ask before every move

(01:03:22) Quarterly snapshots — simple way to track your own patterns

(01:05:22) Closing advice — discipline, patience, and realistic expectations

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#716: When does a financial decision stop being purely about maximizing returns—and start becoming about building the life you actually want?


Karen recently inherited sizable trusts for their children and is now navigating the complicated intersection of investing, taxes, legacy planning, and future financial aid eligibility.


Matt has spent years building a solid index fund portfolio, but as retirement gets closer, he’s wrestling with a familiar investor problem: how do you know when optimizing becomes overthinking?


Kate is trying to decide whether $35,000 should go into the stock market—or into building a backyard gym that could generate income while dramatically improving her family’s day-to-day quality of life.

We’ve got a lot to unpack today, so let’s get into it.


Book by Michael J. McFall - Grind: A No-BS Approach to Take Your Business from Concept to Cash Flow

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#715: She grew up with a Goldman Sachs dad. She still ended up broke in her 20’s. Here's what changed.

Haley Sacks - known online as Mrs. Dow Jones - joins us to talk about the five-step financial framework she calls IBIZA.

Despite every advantage, she spent her twenties anxious, financially dependent, and charging dinners to her parents' credit card.

One birthday trip to a Toronto restaurant crystallized the problem: she couldn't afford the life she wanted, so she borrowed someone else's money to fake it - and spent the rest of the night avoiding her phone while her mom texted about the charge.

We talk about how money beliefs form by age seven, even when parents never say a word about finances. Haley's father had watched wealthy clients' children lose ambition and kept money out of the family conversation entirely.

The lesson Haley absorbed anyway: money comes from outside yourself.

The IBIZA framework walks through five steps - identify your earliest money memory, interrupt the patterns it created, zhuzh your mindset by replacing limiting beliefs, and act.

The final step is tactical: a 15-minute timer, one small action, and a monthly money date to review spending and set goals.

We also get into the concept of financial energy - the idea that you have a finite amount of mental bandwidth for money decisions each day.

Spending it on coupons and skipping lattes leaves nothing left for the moves that actually build wealth: negotiating a raise, automating savings, maxing out tax-advantaged accounts.

Haley also breaks down learned financial helplessness - the belief that the system is too broken to bother trying - and why pushing back against it puts you ahead of most people before you've done a single thing.

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.

(00:00) — Your Childhood Is Running Your Bank Account

(08:42) — Money beliefs form by age 7

(11:35) — Why financial independence matters

(13:00) — The Momofuku story

(17:04) — "Financial energy" — and why you're wasting it

(24:35) — The IBIZA framework, explained

(28:32) — I: Identify your money origin story

(31:07) — "If you don't control your money, it controls your life"

(32:31) — How pop culture shapes money beliefs

(46:51) — I: Interrupt old patterns

(54:24) — Learned financial helplessness

(55:59) — Z: Zhuzh your mindset

(59:06) — The Tyra Banks story

(1:02:54) — A: Act — the 15-minute starter move

(1:06:18) — The monthly money date

Resource:

Haley's book - Future Rich Person: The New Rules for Building Wealth (Even if You're Stuck, Broke, and that Billionaire Won't Text You Back...)
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#714: When you’re making big financial decisions, what matters more: optimizing for the best long-term outcome, or choosing the path that gives you the most flexibility and peace of mind right now?

Melissa retired early and now lives off rental income, but she’s considering selling one property to pay off another. The catch? Her monthly income would stay about the same—so the real question is whether giving up future appreciation is worth the simplicity and stability today.

Von is trying to better understand how real estate returns actually work—specifically, whether cap rates tell the full story for multifamily properties, or whether there’s more going on beneath the surface.

Layla is planning to retire at 50 and has built a strong portfolio—but she’s wondering if she’s leaned too heavily into Roth accounts. Should she keep maximizing a mega backdoor Roth at a high tax rate, or shift toward a taxable brokerage to better bridge the early retirement years?

We’ll get into all of that—the tradeoffs, the assumptions behind them, and how to think through each decision.

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The US economy added 115,000 jobs in April -- and the numbers look solid on the surface.

But dig a little deeper and you'll find a tech sector in freefall, a housing market frozen in place, and consumer sentiment that hit a 74-year low.

This bonus episode breaks down the May jobs report, which came out a week late because the Bureau of Labor Statistics pushed its release from the first Friday to the second Friday of the month.

The job gains were concentrated in healthcare, transportation, warehousing, and retail. Healthcare alone added 37,000 jobs, driven largely by nursing facilities and home health care services for an aging population.

Retail gains clustered in discount stores and warehouse clubs - not department stores or electronics retailers - which tells you consumers are spending more carefully.

Tech got hit hard. The information sector lost another 13,000 jobs in April and is now down 342,000 jobs - about 11 percent - from its November 2022 peak.

People working part-time because they can't find full-time work jumped by 445,000 in a single month.

Consumer sentiment is at its lowest point in 74 years of University of Michigan tracking - worse than 2008, worse than the inflation of the 1970s.

One reason: gas prices. There's a psychological outsized effect to standing at a pump watching the total climb every week, versus an invisible mortgage adjustment buried in a monthly bank statement.

The housing market didn't get its usual spring bounce. Existing home sales ticked up just 0.2 percent between March and April. Inventory rose 5.8 percent, but at 4.4 months of supply, the market still needs roughly 30 percent more inventory to reach balance.

Median sale price sits at $417,700, up less than 1 percent year over year. Homes are averaging 32 days on market - giving buyers more negotiating leverage than they've had in years.

Timestamps:

(00:00) April jobs report: 115,000 new jobs, but tech takes a hit

(02:38) Jobs data matters more than the stock market

(03:14) Where jobs grew: healthcare, transportation,warehousing, retail

(05:14) Consumer sentiment hits 74-year low

(07:46) Why gas prices hurt more than other costs

(11:20) Tech sector down 342,000 jobs from 2022 peak

(11:52) Part-time workers up 445,000 in a single month

(13:38) Housing market: no spring rebound

(15:16) Inventory up, but still 30 percent below a balanced market

(16:16) Housing market frozen - not crashing, not skyrocketing

(17:13) Golden handcuffs: why sellers aren't selling

(18:23) Why buyers have more negotiating power now

Enroll in our course, "Your First Rental Property" while the doors are open! https://affordanything.com/enroll

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