• The cheapest option often ends up costing the most: Jaspreet hired the cheapest property manager and contractors he could find, and paid for it with a nightmare tenant who never signed a lease, thousands lost to a contractor who vanished, and a gutted house. Licensed, insured, reliable help usually costs less in the long run.
• Compare where your hours go with your results: Jaspreet had his hardest-working employee list his five biggest time sinks and his five highest-revenue activities. The top three time sinks drove zero revenue. Working hard and producing results aren’t the same thing, and the gap is easy to miss until it’s written down.
• Wealth comes from owning, not just earning: Jaspreet’s view of how to build wealth rests on his three rules of money: it flows to investors, inflation benefits investors, and the tax code favors investors. Becoming an owner can mean starting a business or simply buying a share of one.
• Always be buying, no matter what markets do: Jaspreet’s hypothetical cousin Bunty invests $100,000 total at four of the worst market peaks in recent history, yet ends up with more than $1 million with dividends reinvested. Bunty did one thing right: he never sold. Consistent buying beats trying to time the market.
• Start with a thesis, then pick investments: Before choosing an index fund or an individual stock, Jaspreet says to decide whether you want growth, income, or wealth preservation. Then apply TRM: time is hard to change, so knowing how to build wealth faster comes down to investing more money or seeking higher returns, which means more risk.
• Look beyond AI to what it runs on: Rather than guessing which chatbot wins, Jaspreet looks at what every AI company needs: energy, data centers, cooling and semiconductors. His team goes a layer deeper, to raw materials like copper, where demand is rising faster than supply.

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Briefs Finance and Market Briefs
Jaspreet’s company, with investor research tools and the free Market Briefs newsletter.
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Anonymous (let’s call them “Maria”) asks: I’m 26 years old, living in the United States, and my net worth is roughly 10 times my annual spending. There is plenty of advice on how to work your way to financial independence, but what I can’t find is how to work after achieving it. While I haven’t reached full financial independence yet, I have enough that I am no longer motivated by money. I don’t find working on someone else’s schedule acceptable, and I want to determine what projects I work on rather than having an employer decide. It feels like I have a negotiation advantage that other employees don’t have, but potential employers can simply avoid hiring me in favor of workers who are motivated by money and forced to work on someone else’s schedule. I am not at a place in my career where entrepreneurship is a good option yet. Because of my investments, I don’t think I can accept a job doing anything other than what I want to do, which is clearly not what my coworkers are doing and not what employers expect of me. I’m starting to worry that I am becoming unemployable.

Matt asks: I have a question about target date funds. I know Joe is not a fan, and I’ve heard him rant about that many times over the years. However, several people I respect—such as YouTuber Rob Berger, Bogleheads leader John Luskin, and financial advisor Peter Lazaroff—invest most or all of their money in a target date or all-in-one fund and speak positively about them. I know Joe disagrees, but these are people I trust. I don’t invest in a target date fund myself, but I’m intrigued by the idea. I would love to hear your point of view on them.

Lucas asks: I’d love your perspective on the timing and financial risk of a career change. My wife and I are both 35. We have a two-and-a-half-year-old daughter who has special needs and a six-month-old son. My daughter will likely need lifelong support, so we’re trying to plan responsibly for future care costs that are still hard to estimate.

We both work in IT consulting at large professional services firms. Our combined compensation is about $375,000 annually, including salary, bonuses, and ESPP. We spend roughly $110,000 per year today, but we expect that number to rise to about $130,000 starting in 2027 as daycare and other kid-related expenses increase.

Over the past four or five years, we’ve paid off our mortgage and saved an average of about $5,000 to $6,000 per month into our taxable brokerage account. We still get our full 401(k) matches, max out our HSA and dependent care FSA, and have a little over $840,000 across our 401(k)s and IRAs. By the time I expect to make a career move, we think we’ll have about 12 months of necessary expenses in cash reserves, and we also plan to purchase a new vehicle before then.

The complication is that I’m considering a transition into financial planning around late summer 2027. I’m comfortable starting near the bottom of the ladder and expect my income could fall by roughly 60% initially. That would bring our household income down to around $250,000, just as we have two kids starting in daycare and our expenses are at their highest. I’m not really happy in my current role, and I feel confident that financial planning is the right long-term move for me, but I’m struggling with whether this is the responsible timing. Should I make the switch in 2027, accepting a temporary step back in income, or stay in IT consulting another year or two to build a bigger cushion?

As far as the timing of the transition, I’ve already taken major steps over the past few months to position myself for the switch, including completing a financial planning externship, networking with local CFPs to gauge the market in my area, and studying for my Series 65. I’m also taking my last block of paternity leave in January and owe my company 30 business days after returning. By that time, it will be performance discussion season, bonuses are paid out in late May, and 401(k) matches are in late June, so it’s worth staying into the summer.

What blind spots do you see, and am I accounting for the right things, especially given our children, higher near-term expenses, and the uncertainty around our daughter’s long-term care needs?

• Not chasing money can make you more employable: When I hire, I look for two things: a drive for mastery and a belief in the mission. Someone who isn’t there just to collect a paycheck is exactly who I want on my team. Money motivation would be the wrong fit.
• Small businesses reward results over seat time: Joe pointed out that big corporations often care whether you’re at your desk from 8 to 5, while small businesses care whether the work gets done. My caveat: in a tiny company, one or two personalities shape your entire experience.
• Look for founders who are humble but confident: The best small-business leaders know what they’re bad at and hire people better than them, without letting ego get in the way. A quick test before any job or career change: would you want to spend an eight-hour airport layover with these people?
• A good target date fund is harm reduction: Joe argues most people can learn to build a simple three-fund portfolio, and that many target date funds are packed with high-fee leftovers. I see a low-cost one from Vanguard, Fidelity, Schwab, or T. Rowe Price as a smart default for anyone tempted by crypto or individual stocks.
• Your savings exist for moments like this: Lucas has spent years paying off his mortgage and building a taxable brokerage account. To me, funding a career change into work he actually wants is exactly what all that saving is for. Waiting “one more year” just delays the clock.
• Make your career change while your kids are young: Joe started his financial planning career when his kids were small and says getting that pain out of the way early was worth it. Time, not money, is the bigger currency in any career change, and leaner years can still be rich ones.

Free Asset Location Guide
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Episode #709 with Keith Wargo
Planning for a child with special needs, including special needs trusts and ABLE accounts.
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Episode #755 with Rob Berger
Our interview with Rob Berger, one of the target date fund fans Matt mentions.
Listen to Episode #755

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The entrepreneur coaching program Joe recommends.
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• The best idea wins, not the boss: Ron says Steve was never the dictator people imagine. He hated malls and the name Genius Bar, then reversed himself on both once he heard the reasoning, a core trait of Steve Jobs leadership.
• Invest heavily before handing over the keys: Steve Jobs leadership meant delegating fully but investing heavily first. For about a year, Steve called Ron every night at 8 p.m. to talk family, faith, Pixar, and Apple, so Ron would know how Steve thought.
• Big goals are easier to rally behind: Ron’s high school soccer team won two games one year and made the state tournament the next, after he set an outsized goal. He argues people work harder chasing something great than chasing small improvements, and that playing it safe keeps a career moving at an ordinary pace.
• Design around service, not selling: When Ron’s team shared their best-ever service experiences, 16 of roughly 18 people named a hotel. That insight shaped the Apple Store: warm welcomes modeled on the Ritz-Carlton, and a bar that dispensed advice instead of drinks, later named the Genius Bar.
• Trust has to come before transformation: At Apple, Ron inherited trust because Steve had picked him; at JCPenney, nobody knew him, and he overhauled pricing within three months. He says the vision wasn’t what failed, but moving too fast to earn his team’s trust was.
• Cure analysis paralysis by trusting instinct: Ron says overthinking usually means relying too much on the mind and not enough on instinct. His fix is to put the spreadsheet down, take a walk, visit stores, and observe real people until that inner voice comes through.

Would you turn down $120K for work you love?
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Shop Different by Ron Johnson
Ron’s novel-style account of building the Apple Stores, with an inside look at Steve Jobs leadership:
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• Cash gives you the freedom to bet on yourself: Jared’s coworkers earned the same Wall Street paychecks, but many spent them on pricey apartments and weekend golf. Because he lived cheaply, Jared came out of the Lehman Brothers collapse with enough liquidity to skip the job he was offered and start his own newsletter instead.
• A smoother ride beats the highest return: Jared focuses on risk-adjusted returns rather than raw returns, because the S&P 500 fell 57% from 2007 to 2009 and investors who panic-sell near the bottom lock in that loss. A portfolio built to reduce volatility makes it easier to stay invested when markets drop.
• Split your portfolio five equal ways: Jared’s Awesome Portfolio holds 20% each in stocks, bonds, cash, gold, and real estate, rebalanced once a year. In backtests going back to 1971, it has returned about 9% annually, a point or two below the S&P 500, with roughly half the volatility and a worst year of −11.8%.
• Test your risk tolerance at the craps table: Jared’s gut check is to go to Vegas and notice how much you’re willing to lose before the pain makes you walk away. Despite a career trading on Wall Street, his limit is a few hundred dollars, while some friends will put $10,000 on the table.

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Jared’s research services and market newsletter.
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The Awesome Portfolio by Jared Dillian
Jared’s book on the simple five-asset strategy he built after losing $500,000 in the Lehman Brothers collapse.
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Jared Dillian on X
Follow Jared for ongoing market commentary.
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• AI changes the economy, not valuation fundamentals: AI will create winners and losers, just as the car did for saddle makers, and it makes future growth harder to model. But Rob argues the basics haven’t moved: valuation still matters eventually, even when it appears not to for a while.
• High valuations aren’t a reason to change course: Rob believes stock valuations are elevated, especially in certain sectors and in the U.S., yet he isn’t changing his asset allocation at all. He doesn’t know when a downturn will come or what will trigger it, and timing both the exit and re-entry just adds more chances to fail.
• Growth alone won’t fix the national debt: Higher productivity from AI might bring temporary relief, but Rob compares the government to a family that spends every raise. Fixing the debt and Social Security will mean higher revenue, reduced benefits, or both, and taxing only the wealthy won’t cover the gap.
• Cover necessities with guaranteed income first: For anyone nearing retirement, Rob’s approach to retirement planning starts with guaranteed income (Social Security, a pension, or a TIPS ladder) sized to cover basic expenses. The rest of the portfolio can then fund everything else, which makes market swings far easier to live with.
• Savings buy freedom long before retirement: Living below your means pays off at 30, 35, and 40, not just 65. When Rob landed in a job that wasn’t right for him, his savings let him accept a significant pay cut for a new role that became the best job he ever had.
• Money skills are more habit than information: Rob sees getting better with money as mostly psychology and routine, not information. He quit a near-daily mocha latte habit for health reasons, struggled through the first day, and three weeks later didn’t miss it, proof that people control more of their happiness than they think.

Cornerstone
Retirement worries feel overwhelming? See your whole financial picture on one page.
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Rob Berger on YouTube
Rob’s channel covering retirement planning, investing, and the questions his audience sends in most.
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Anonymous (let’s call them “Amelia”) asks: How would you define the difference between an emergency fund, sinking funds (such as for a new laptop), and medium-term savings (like a career break or a big trip within the next two years)? How should we think about and treat these pots differently, and is there a defined line or overlap between them? Additionally, some people replace the term emergency fund with opportunity fund, which adds another dimension.

Secondly, how do you create a structure to decide how to apportion discretionary money across competing goals? How should someone choose which pot or goal to prioritize or allocate the largest contribution to, versus funding each pot equally?

For context, I am 42 and based in the UK. My defined contribution pension—similar to a 401(k)—can be accessed around age 57, and with my current contributions, I expect to retire at 64. My goal is to have an eight-month emergency fund, and I currently have four months saved. I would like to start funding other goals, such as a career break, travel, and home improvements, alongside building my emergency fund. Can I start funding those other pots now, or should the emergency fund be fully funded first? Once the emergency fund is taken care of, at what point should I pivot back to bringing my retirement age forward versus funding adventures over the next two decades? How should I balance multiple goals across differing timelines and magnitudes, weighing the flexibility of cash savings against the growth of investing?

Anonymous (let’s call them “Esther”) asks: I am trying to figure out the best way to organize my finances now that I finally have the courage to take a sabbatical after listening to one of you and Joe’s previous episodes.

My partner and I are in our mid-to-late 30s. We have been DIYing our finances, so it is not the most sophisticated. Jointly, we have $392,000 in our 401(k) and $189,000 in our Roth IRAs, and we max out the Roths every year. We are considering converting our 401(k) to Roth during these low-income years. We have $394,000 in a taxable brokerage account and about $80,000 in cash. We own a paid-off home worth $315,000 and moved to a rental for the sabbatical period. I am thinking of investing half of that into the brokerage account and saving the other half for a down payment on our future home, likely after my one- to two-year sabbatical.

Most of our investments are spread between VFIAX, VIGAX, and VGIX, and I recently added some VITAX. We have no bonds, and I am worried that we lack diversification, but I am not interested in managing rentals because we love to travel. We would also love to have the option to retire early in our mid-40s or 50s.

If that is our goal, should we wait to convert our 401(k) and do it when both of us retire? Will our current portfolio be too volatile, and should I rebalance everything? What are the implications of converting during early retirement years if we also want to take advantage of the $98,000 tax-free withdrawal from our brokerage account?

Larry asks: I have a question about objectively grading the economic success of politicians at both the state and national levels. We often judge the success of politicians based on emotion or political spin. For example, when a recent jobs report showed great numbers, the opposing party claimed the data was rigged. Meanwhile, the stock market has been up, but so have inflation and home prices, meaning one indicator may look positive while another does not. Could you suggest a more objective framework or composite metric to evaluate how a president, Congress, or governor measures up regarding economic indicators? How can voters confidently assess whether an elected official has done a good job managing the economy?

• Don’t turn your emergency fund into an emergency: With four months already saved, I’d keep making small, steady contributions while also funding a career break, travel, and home projects. Joe’s test: check twice a year that it’s still growing.
• Put a price and deadline on every goal: Divide each goal’s cost by the months until you want it, and the monthly total is almost always unrealistically huge. That’s the point: now you can cut goals, shrink them, or push the timeline out.
• Earmark sabbatical money before making any other plans: Esther’s $80,000 in cash probably won’t cover a two-year career break, so I’d first set aside what the sabbatical will pull from her brokerage account. Of what’s left, half can stay invested and half becomes flexible cash for a future down payment.
• Convert to Roth now, not in early retirement: A sabbatical’s low-income years are a golden window for Roth conversions, as long as you plan for the tax bill. As Joe puts it, the sooner you stop splitting your returns with Uncle Sam, the better.
• Your all-stock portfolio’s real risk might be you: In your 30s, you have the risk capacity for zero bonds; the question is risk tolerance. Look up each fund’s standard deviation on Morningstar, translate it into real dollars, and add small-cap and international exposure for true diversification.
• Judge politicians on process, not outcomes: No single leader controls much of an economy shaped by earnings, the Fed, wars, and disasters. Like judging someone’s health by their habits rather than one checkup, ask whether the underlying policies are sound, not what this quarter’s numbers say.

Paul Merriman Financial Education Foundation
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• The 2019 rent laws made empty apartments rational: The 2019 HSTPA ended the rent reset after a tenant moves out. Owners must still renovate vacant units to current code, often a six-figure job, with no way to recoup it. So at least 60,000 apartments under rent stabilization sit empty.
• Frozen rents push costs onto someone else: When rents can’t rise to cover taxes, insurance, and water bills, costs don’t disappear. In mixed buildings, market-rate tenants absorb them. In fully regulated ones, owners defer maintenance, patching boilers and delaying elevator repairs, until the building starts to fail.
• A bargain price often comes with a warning label: Under rent stabilization, some buildings sell for $50,000 per apartment, and a few for as little as $10,000. The price is low because regulation caps future cash flow. Whether it’s a rental property or a laundromat, a cheap asset usually signals trouble with the income it can produce.
• Averages can hide the real story: Manhattan’s $5,500 median asking rent grabs headlines, but the median rent New Yorkers actually pay is closer to $1,600. Before trusting any average, whether it’s a rent report or a salary survey, ask who’s in the sample and check the median too.
• Changing the tenant doesn’t change the math: Rent stabilization has no income limit, but Kenny argues means testing wouldn’t fix it. If an apartment brings in $700 a month and costs more to run, the building loses money no matter who lives there.

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Kenny Burgos on X
Kenny’s posts on rent stabilization, vacant apartments, and New York City housing policy.
@KennyBurgosNY

New York Apartment Association (Housing NY)
Kenny leads this organization, which represents owners and managers of rent-stabilized housing in New York City. It posts weekly content, and he mentioned it on the show, noting its handle is @housingny on social media.
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Free Guide: 7 Costly Mistakes Beginner Rental Property Investors Make
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Nieves asks: I recently quit my job and moved to Madrid, Spain for a year to pursue an MBA. I received a scholarship for the program, but I had to use most of my savings for a €20,000 deposit that will be returned after I complete a six-month internship following the MBA. I also took out a €30,000 loan for living expenses for the next 12 months at an interest rate under 4%.

I’m 30 years old and have around $150,000 in my old 401(k), $50,000 in my Roth IRA, and a duplex in St. Louis, Missouri that I bought in 2021 for $240,000. The mortgage, including taxes and insurance, is about $1,500 a month, and it brings in around $3,100 a month in rent. One of the units is a midterm rental, so I have additional expenses associated with that unit.

I’ve been thinking about selling the property because my tenants have started paying late and the property needs a new roof and a few other repairs. I don’t have enough cash to replace the roof out of pocket, and managing the property from abroad has become stressful. I could likely sell the duplex for around $250,000 to $275,000, and I currently owe $180,000 on the mortgage.

How do you know when it’s okay to let go of an investment that is objectively a good long-term asset? I’m struggling with whether selling would be a smart simplification for peace of mind or if I’d be giving up a valuable long-term asset.

Mandy asks: I really loved your most recent podcast on the July jobs report that came out. I saw something recently in the news stating that 100% of the labor workforce decline was actually female, and that 100% of it was females leaving the workforce. I wasn’t sure how accurate or correct that information was, and I was curious if it is accurate, what is the reason behind it and what factors are impacting that?

James says: Hi Paula, my name is James. I’m calling regarding episode 744 with Joseph Moore, the historian that you had on, and that was one of the most interesting podcasts about finance that I’ve ever listened to. I just wanted to call and give you that accolade and to say that I will keep listening to your show on a regular basis. I’m a full-time stacker and a part-time afforder. So keep up the good work, and I look forward to listening to your episodes in the future. And also make it easier to leave a review on your website because I couldn’t figure out how to do that. So that’s why I’m leaving this message. Talk to you later. Bye.

• Don’t let temporary problems drive permanent decisions: One set of late-paying tenants is a short-term, solvable problem; if you own rentals for decades, you’ll see every kind of tenant. Before you sell rental property, I want to make sure you’re not making the right decision for the wrong reason.
• A new roof is a front-loaded investment: Every major capital expenditure buys years of not having to think about that component again. A roof can last 25 to 30 years, so before you sell rental property over one big repair, remember that your future self benefits from the payment.
• A property manager can solve what selling solves: Deciding to sell rental property gets you away from tenant headaches, but so does hiring a professional. Beyond the time savings, a good manager brings local legal expertise, handles contractors, and gives you real peace of mind, especially if you’re managing from another country.
• Compare unleveraged returns before you sell rental property: Add the property’s cap rate to its expected appreciation, then compare that to what your after-tax, after-fee proceeds could earn elsewhere, like an S&P 500 index fund. Just remember it’s not a risk-adjusted comparison, since every property has its own risk profile.
• A labor force decline isn’t the same as job losses: Labor force participation counts people who have jobs or want them. In many cases, July’s drop reflects women moving from wanting work to not wanting it, driven partly by childcare costs and return-to-office mandates, a multi-year trend among mothers of young children.
• Zoom out before you trust a single month: Women made up 100% of July’s labor force decline, but they also captured 98% of August’s net job growth and about 85% of 2026’s job gains so far. One month makes a headline; the long-term trend line tells the real story.

Episode 744 with Historian Joseph Moore
The episode James called in about, on the long historical view of money and why grounded, data-driven optimism is so hard to find.
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Joe’s Interview with Joseph Moore on Stacking Benjamins
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Bureau of Labor Statistics: Employment Situation Report
The BLS jobs data behind our discussion of labor force participation and 2026 job growth.
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• High self-worth outperforms high SAT scores: Marisa Franco’s research found that people with high self-worth and high SAT scores earned nearly double the income of people with low SAT scores. For people with low self-worth, SAT scores made almost no difference to future income at all.
• Self-esteem has a good twin and a bad twin: People with high self-esteem split into two profiles: one treats others with compassion and builds strong relationships, while the other is hostile and antagonistic, reporting worse relationships than people with low self-esteem altogether.
• Low self-worth can sabotage financial goals: As a portfolio nears a target like financial independence, people with low self-worth may pull money into safer assets prematurely — not from bad math, but from an ingrained belief that good outcomes are set to be taken away.
• High self-worth makes stagnant wages easier to leave: Research shows people with low self-worth are more likely to stay in jobs with stagnating pay, while people with high self-worth are more likely to leave — a pattern researchers link to needing the outside world to reflect an internal sense of worth.
• Feeling and doing are two separate skills: Franco defines self-worth as sensitivity (noticing even small emotions) plus responsiveness (using those emotions as information). The practice of treating every feeling as if it matters, she argues, is what builds a durable sense of self-worth over time.
• Self-worth and net worth are linked, not equal: Franco pushes back gently on the common refrain that net worth isn’t self-worth. She argues self-worth and net worth are connected — high self-worth helps people capitalize on opportunities — without self-worth needing to depend on a bank balance.

Worth: The New Science of Self-Esteem and Secure Attachment
Marisa Franco’s book, which explores the research behind self-worth and net worth featured in this episode.
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Marisa Franco’s website
Speaking engagements, articles, and more from Marisa.
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Marisa on Instagram
Follow for updates, or reach out for signed copies via Lost City Books.
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• Knowledge is now abundant, but judgment is scarce: Litowitz argues that when a resource shifts from scarce to abundant, something else becomes the new bottleneck. With AI making knowledge cheap, the scarce resource left for humans is judgment and agency — your ability to weigh evidence and act on it.
• Use AI to expand your thinking, not shrink it: Litowitz warns against asking AI for a single compressed answer, since that hands over your judgment. Instead, bring your own reasoning first, then ask AI to poke holes in it, play devil’s advocate, or point out what you missed.
• Your S&P 500 fund is one AI bet: Seven stocks now drive most of the S&P 500’s gains, and they’re all riding the same AI thesis. A supposedly diversified index fund concentrates risk on a single storyline, not five hundred independent ones.
• Hold a strong opinion, but hold it loosely: Litowitz calls this a “strong opinion, weakly held” — the best answer you have right now, tested and ready to be replaced the moment better evidence shows up. Confidence comes from how fast you adapt, not from being right the first time.
• Chase fast feedback loops, not fancy perks: Litowitz left a cushy investment banking job for trading because the feedback was instant — right or wrong, every second. He tells young people to pick jobs and environments that show them results quickly, since that’s how real learning compounds.
• A shock and a regime change aren’t the same: A shock rattles markets but fades if you can wait it out. A true regime change permanently alters what’s produced, flips what’s scarce, moves the bottleneck, and never reverses — which is how Litowitz frames AI’s arrival now.

The Adaptability Quotient by Alec Litowitz
Alec’s new book, discussed throughout this episode.
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Grit by Angela Duckworth
Referenced in this episode as a foundational read on perseverance and passion.
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