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Latest Episodes:

Q&A: When Being Good With Money … Isn't Good Enough Jul 22, 2025

Show notes

#627: Jlyn and her husband are 20 years from retirement, but they’ve got their eye on a second home they’ll live in when the time comes. Should they make the purchase now, or keep saving?

Reese was recently laid off, and she’s struggling to choose between two financially responsible paths. Should she continue her long-term disability insurance? Or is it wiser to save money?

Kip’s youngest has finally graduated from college, and he’s looking forward to an early retirement. But, with the eyewatering costs of long-term healthcare, is this still a viable path?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

P.S. Got a question? Leave it here.

Resource mentioned:

Reese's original question in Episode 417

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The Hidden Psychology Behind Failed Dreams, with Yale’s Dr. Zorana Ivcevic Pringle Jul 18, 2025

Show notes

#626: A software programmer and an accountant walk into retirement planning. Are they being creative? Dr. Zorana Ivcevic Pringle, a senior research scientist at Yale University's Center for Emotional Intelligence, says absolutely.

Pringle defines creativity as something that's both original and effective, whether you're solving an accounting problem or planning an unconventional retirement.

We explore the gap between having ideas and actually implementing them. You have this brilliant vision for starting a business, changing careers, or retiring early, but somehow you never take the first step. Pringle calls this the implementation gap, and she explains why it happens.

The conversation centers on a hypothetical couple: both 55 years old, one a programmer, the other in middle management. They want to retire at 57 and travel the world. Pringle uses this example to illustrate how creative problem-solving works in real life.

She explains that creativity requires comfort with uncertainty. When you're doing something new, you don't have a blueprint or checklist. There's always the risk that your early retirement plan could fail spectacularly — imagine having to return to work at 59 after the market tanks and your portfolio gets crushed.

Here's the key insight: you don't need full confidence to start. Pringle compares creative confidence to fuel in a car. You don't need a full tank — you can start with just a quarter tank and refuel along the way. Each small success builds more confidence for the next step.

The bottom line? Innovation happens through constant iteration. Your final destination might change throughout your career and retirement, and that's completely normal.

Resources Mentioned:

https://www.zorana-ivcevic-pringle.com/

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) Implementation gap intro

(1:00) Creativity beyond arts

(2:00) Original plus effective

(3:00) Ideas to action gap

(5:00) Retirement as creativity

(7:00) Openness drives creativity

(8:00) Problem finding process

(10:00) Big Five traits

(12:00) Openness and creativity

(15:00) Traits can change

(18:00) Uncertainty creates risk

(20:00) Courage versus comfort

(23:00) Self-efficacy challenges

(25:00) Quarter tank confidence

(28:00) Creative failure recovery

(32:00) Creative blocks

(36:00) Pivoting versus quitting

(39:00) Emotions as information

(42:00) Metrics versus intuition

(50:00) Implementation strategies

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JL Collins Part 2: What Happens When You Don't Need to Work Anymore? Jul 15, 2025

Show notes

#625: What do you do when you've reached financial independence? JL Collins says it depends entirely on your spending rate, not just your net worth.

Collins joins us for part two of our conversation about what happens after you reach financial independence. He tackles the question of whether you should invest differently once you've "won the game."

Someone with $5 million spending $100,000 per year sits in a completely different position than someone with the same amount spending $200,000 per year. The first person can afford to stay aggressive with stocks. The second person needs bonds to smooth the ride.

Collins walks through his withdrawal strategy using his daughter as an example. She stepped away from corporate life in her early thirties and now follows an 80-20 stock/bond allocation.

She pulls dividends from both funds into her checking account, covering about 2.5 percent of her target 4 percent withdrawal rate. Vanguard automatically sells shares to cover the remaining 1.5 percent.

We cover Collins' thoughts on the 4 percent rule, which he calls extraordinarily conservative. He references Bill Bengen's research showing that 5 percent withdrawals succeed 86 percent of the time.

Collins would take those odds to escape a soul-crushing job, especially since most financially independent people end up accidentally making money anyway.

We discuss the tension between frugal habits that build wealth – and learning to spend money once you have it. Collins flies first class, but he drives a basic car.

Collins explains why financially independent people often stay engaged with work — the problem was never work itself, but working without agency.

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) Intro

(2:00) Investing when you've won the game

(5:30) Spending rate versus total wealth

(8:00) Three-year versus ten-year timelines

(11:00) Adding bonds gradually or all at once

(14:00) Why 4 percent is extraordinarily conservative

(17:00) Soul crushing jobs and 5 percent risk

(24:16) Withdrawal frequency and dividends

(27:16) Automatic share sales setup

(31:16) Starting business while financially independent

(36:16) Accidentally making money after retirement

(47:09) Agency versus having to work

(50:09) Spending advice for frugal philanthropists

(54:09) Charity auction magnifying effect

Resources Mentioned:

https://affordanything.com/377-how-i-discovered-the-4-percent-retirement-rule-with-bill-bengen/

https://affordanything.com/bill-bengen-created-the-4-rule-now-he-thinks-we-can-withdraw-more/

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JL Collins Part 1: The Simple Path vs. The "Optimal" Path Jul 11, 2025

Show notes

#624: JL Collins, author of "The Simple Path to Wealth" — the guy synonymous with VTSAX and chill — joins us for Part 1 of a two-part series where we skip the basics and dive straight into the complex stuff.

We ask him whether his simple approach actually beats more sophisticated strategies, and his answer might surprise you.

He says that Paul Merriman's four-fund portfolio probably outperforms his one-fund approach mathematically. But Collins argues that execution trumps optimization every time.

Most people can't stick with complex strategies for 20 years, he says, especially when those strategies require selling winners to buy losers – something that goes against human nature.

Collins prioritizes what works in real life over what looks good on paper. He calls index funds "self-cleansing" because they automatically rotate out failing companies and sectors while rotating in the new winners. You don't need to predict which companies will dominate next – you'll own whatever rises to the top.

The episode covers his thoughts on VTSAX versus VTI, international diversification, and why he'd rather put Tabasco than Cholula on his eggs — his quirky way of explaining personal preferences in nearly identical investment options.

Resources Mentioned: Episode 31, Interview in 2016 with JL Collins

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) Intro

(1:00) The efficient frontier

(2:00) Simple vs optimal but complex paths

(4:30) Paul Merriman's four-fund portfolio vs VTSAX

(6:00) JL says Merriman's approach is mathematically superior but not behaviorally

(7:30) Risk parity investing discussion

(8:30) Sequence of returns risk and retirement bonds

(12:30) JL's birthday email from Jack Bogle

(15:00) VTSAX vs VTI

(17:00) Total stock market funds across brokerages

(23:30) Mag 7 concentration risk

(27:00) Sears story and self-cleansing index funds

(30:30) International diversification and US dominance

(39:00) World funds versus separate international

(45:00) When to shift to world fund

(47:30) Bond allocation timing strategies

(48:30) Target date funds

(50:30) One-fund vs two-fund approach

(52:00) Historical diversification and Nifty 50

For more information, visit the show notes at https://affordanything.com/episode624

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Q&A: “Help! My Mom’s Financial Crisis Is Becoming Mine!” Jul 08, 2025

Show notes

#623: An anonymous caller feels trapped in a no-win situation with her financially reckless mother. She has the means to bail her out, but it doesn’t feel right. What should she do?

Shannon is excited about investing in several companies overseas. But she can only access them using American Depository Receipts. What are they, and how do they work?

Jennifer calls back with an update on putting a vacation on a credit card and playing the rewards game.

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

P.S. Got a question? Leave it here.

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First Friday: Why Americans Are More Pessimistic Than Ever Jul 04, 2025

Show notes

#622: #622: The headlines said America added 147,000 jobs in June. The reality? Private companies actually cut 33,000 positions.

Grad students just lost access to unlimited borrowing. Parent PLUS loans now cap at $65,000. And tariffs are about to jump as high as 70 percent.

Everything is changing at once — taxes, tariffs, student loans, and immigration policy. And data from the University of Michigan says that consumers feel more pessimistic than they did six months ago.

Welcome to the 4th of July First Friday episode. On America's 249th birthday, we unpack these economic stories.

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) Introduction

(1:19) Historical trivia about the Declaration of Independence

(2:28) Three presidents died on July 4th — statistical improbability explained

(4:24) Trump signs domestic policy bill extending 2017 tax cuts

(6:13) Student loan changes — borrowing caps and repayment plan eliminations

(8:53) Tariff pause expires July 9th, new rates announced

(12:00) Original tariff rates and Lesotho example breakdown

(16:26) June jobs report headlines versus private sector reality

(22:54) ADP reports private job losses while government hiring grows

(26:46) Consumer confidence drops 18 percent since December

(30:59) Inflation expectations versus actual 2.4 percent rate

(34:19) Fed takes wait-and-see approach amid policy uncertainty

(36:58) Labor market stagnation mirrors Federal Reserve strategy

For more information, visit the show notes at https://affordanything.com/episode622

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Q&A: Which Investments Should Go Into Which Accounts? Jul 02, 2025

Show notes

DOWNLOAD the FREE Cheat Sheet: ASSET LOCATION MADE SIMPLE at affordanything.com/assetlocation

#621: Jared is attracted to the favorable terms of the annuity plan that his employer offers, but he’s hesitant to pay the opportunity cost of locking up his money now. What should he do?

An anonymous caller is struggling to find the efficient frontier with only three funds to choose from in his Thrift Savings Plan. Is there any hope for him?

Jack feels great about the funds in his portfolio, but he’s losing sleep over how to apportion them between his taxable, pre-tax and Roth accounts. What’s the best tax strategy for him?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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

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The Hidden Cost of Replacing You at Work, with “Money with Katie” host Katie Gatti Tassin Jul 01, 2025

Show notes

#620: You probably think your value to your employer equals your paycheck. Katie Gatti Tassin has news for you — you're worth way more than that.

The host of "Money with Katie" recently joined us to break down a framework that could change how you negotiate forever. Her formula is simple: Your worth equals your market rate plus what it costs to replace you, raised to the power of your unique skills.

Most people focus only on market rate — what similar jobs pay in your area. You can find this through salary transparency laws, LinkedIn data, or job postings. But that's just the starting point.

The real eye-opener? Replacement costs. When you leave, companies face recruiting fees, interview time, onboarding expenses, and lost productivity. For mid-level roles, recruiters charge 15 to 25 percent of your first-year salary. Senior positions cost even more — headhunters for executive roles charge 25 to 35 percent of total compensation.

A company replacing an $80,000 employee might pay $20,000 just in recruiter fees. For a $200,000 executive, that jumps to $70,000. Add training time and the productivity gap while they search, and replacement costs can hit 50 to 200 percent of annual salary.

Then there's your "special sauce" — the unique value you bring. Maybe you have deep client relationships, specialized skills, or institutional knowledge that would take months for a replacement to develop.

Katie learned this framework through her own career pivots. She started as an ad copywriter but shifted into user experience writing after working closely with a UX designer who told her the pay was much better. That internal pivot positioned her for an external move that doubled her compensation from $70,000 to $140,000.

Katie had to catch a flight — she visited our New York studios during her book launch tour — but the conversation covers practical tactics for earning more and building wealth.

For more information, visit the show notes at https://affordanything.com/episode620

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Q&A: My Company Is Going Public and I Have No Idea What to Do – Plus, Should I Fire My Advisor? Jun 24, 2025

Show notes

#619: Dave is no longer happy with his financial advisor, but he’s nervous about switching over to self-management after being completely hands-off for so long. What should he do?

An anonymous caller keeps hearing about the benefits of Cost Segregation for investment property. What is it? And should he apply this strategy to his recently acquired duplex?

Another anonymous caller is eagerly anticipating a windfall from his employer’s upcoming IPO. How should he prepare for this, and what happens if it fails?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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

For more information, visit the show notes at https://affordanything.com/episode619

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How to Retire at 50 While Supporting Aging Parents, with Frank Vasquez Jun 20, 2025

Show notes

DOWNLOAD the RISK PARITY PORTFOLIO CHEAT SHEET at affordanything.com/riskparity

______________

#618: Frank Vasquez watched his parents, ages 91 and 96, struggle financially in retirement.

They were immigrants. His dad was a physician. They raised five kids. They retired in the early 1990’s. But by 2009, they ran out of money.

When Frank was 45, in 2009, his parents would call asking for money to help make ends meet.

This reality hit Frank hard and sparked a decade-long quest to crack the code on sustainable retirement withdrawals.

At age 45, Frank set an ambitious goal: retire in his early 50’s while still supporting his parents financially.

The problem? Most financial experts simply told people to spend less rather than optimize their portfolios for higher withdrawal rates. Frank wasn't satisfied with that answer.

You'll hear how Frank discovered that many retirees leave money on the table by holding too much cash or following overly conservative allocation models.

Through extensive research, he found a sweet spot for stock allocation that maximizes safe withdrawal rates — something most traditional advisors miss entirely.

Frank walks us through his approach to portfolio construction, explaining why he believes in balancing growth and value stocks while keeping bonds limited to US treasuries for recession protection.

He breaks down the math behind safe withdrawal rates and reveals why property taxes pose a hidden threat to retirement security as home values climb.

You'll learn about risk parity strategies, macro allocation principles, and why diversification across uncorrelated assets creates more stability than traditional 60/40 portfolios.

The conversation covers Frank's Golden Ratio Portfolio, a structured approach to asset allocation designed specifically for the retirement drawdown phase.

Frank figured out how to fix what went wrong with his parents' retirement. His approach could help you avoid the same mistakes.

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) Introduction

(01:04) Frank's parents' financial struggles

(05:21) Finding a sustainable retirement portfolio

(10:19) Learning from market crashes

(13:25) Different types of investments

(25:10) Building the perfect portfolio

(32:25) Frank's real-world example

(39:24) Property taxes and retirement goals

(44:21) Safe withdrawal rate basics

(45:22) How much to put in stocks

(51:03) Why bonds matter

(54:23) Adding alternative investments