Jared asks: I am active-duty Air Force, currently serving as a major, married with two kids under 10. My wife and I rent, and we have about $2.5 million across our retirement and taxable accounts, with most of it in retirement.

My dilemma is that both of my parents were diagnosed with early-onset Alzheimer’s around age 60, but we started noticing cognitive decline in their mid-50s. Both carry an APOE 3/4 allele, which is a significant genetic risk. I have a 25% chance of inheriting the 4/4 allele, which gives me a 12-times increased risk of early-onset Alzheimer’s.

Because my window of peak cognitive health may be shorter than average, I want to be proactive. What steps should I take regarding genetic testing, and what should I do about insurance? We currently have term life insurance of $1 million each for my wife and me that runs until our kids are past college age. But what steps should I take going forward in terms of disability or long-term care insurance, given my elevated risk? We haven’t secured that insurance yet, and I haven’t done any genetic testing. We’re trying to get a collective perspective before delving into those waters.

Virginia asks: I previously called in on Episode 308 trying to figure out how to pay for travel for the first 5 to 7 years of retirement before taking Social Security. Since that call, I unexpectedly took a higher-paying position, increased my savings, and about two years later inherited approximately $400,000 (mostly in a brokerage account) from my father. Between increased savings, market growth, and the inheritance, I was able to plan for double the travel I originally wanted when retiring at 60. Then in August, at 58 years old, I was unexpectedly offered early retirement from my federal job and took it.

Now, my question involves housing during retirement. I currently own a small condo with no mortgage, but the HOA fees have increased significantly due to inflation and poor budgeting. While the condo mostly meets my needs right now, I will not be able to age in place here due to multiple factors, including having to shovel snow without a garage space. If I move to get the neighborhood and amenities I want, I will either have to rent for about $2,700 a month or take out a mortgage of $200,000 to $250,000. With monthly payments, taxes, insurance, and HOA fees, buying would cost about the same as renting. I have been a homeowner for over 30 years and do not need to make this decision immediately—probably 5 to 7 years down the road. Renting out my current place would net about $550 a month before reserves, or I would need to sell it to access the equity if I buy. How should I evaluate this rent-versus-buy decision?

Anonymous (let’s call them “James”) asks: I have a question about paying off a mortgage early. I’d welcome your thoughts on our specific situation, but I’m also curious how you think about the trade-offs more broadly.

My partner and I are in our late 30s and early 40s. We bought our first home in 2023 for $650,000, put down 20%, and have a $520,000 30-year fixed mortgage at 6%. We pay down the minimum each month and have about $500,000 left on the mortgage. Otherwise, we’re debt-free. We take home about $300,000 a year and spend around $160,000 inclusive of the mortgage. We both max out our 401(k)s, which total about $550,000. We also invest $6,000 a month in a taxable brokerage account where we have about $50,000 in broad-based index funds. We have a young child and his grandparents fund his 529. We also have about $240,000 in a high-yield savings account. While I like the idea of a healthy emergency fund, we are definitely holding a lot in cash.

We’re considering putting extra money toward the mortgage each month. At a 6% interest rate, I think of that as roughly a guaranteed 6% rate of return on that money. Is that the right way to think about it? How would you think about the trade-off between paying down the mortgage versus investing more versus some other option? And would making extra payments today have any downside if we refinance later?

• Buy insurance before you get genetic testing: If a test shows elevated risk for early onset Alzheimer’s, you have to disclose it on long-term care and disability applications. GINA, the federal genetic discrimination law, mostly covers health insurance and employment, not those policies. Get coverage first, while you truthfully have nothing to report.
• The bigger risk is living, not dying: Joe’s first question was whether $2.5 million would already support Jared’s family if he died. If it would, life insurance may matter less. With early onset Alzheimer’s, the costlier scenario is a long disability or long-term care stay, which can drain money from everyone else in the family.
• If you are at risk for early onset Alzheimer’s, start planning now: The number of choices you have today is far larger than the number you’ll have after a diagnosis. Planning ahead doesn’t make life more rigid. It lets you pivot faster when health, a layoff, or a family emergency forces your hand.
• Put the decision-making triggers in writing: Beyond a durable power of attorney, health care directive, and funded revocable trust, I want Jared to agree in writing with his spouse on the warning signs that mean she takes over the finances. With early onset Alzheimer’s, the person affected may not recognize the change.
• Run the price-to-rent ratio before you decide: Divide a home’s purchase price by a year of rent. Fifteen or below is a clear buy, and 25 or above is a clear rent. In between, your preferences, timeline, and interest rates decide. Also remember the opportunity cost of your down payment.
• Extra mortgage payments early on go furthest: Because mortgages amortize, prepaying early in the loan saves far more interest than prepaying near the end. Joe and I both favor James paying down that 6% mortgage, and extra payments won’t hurt a future rate-and-term refinance. Just avoid a cash-out refi.

Is your family covered if you can’t work?
Map your insurance, savings and retirement on one free page and find the gaps
affordanything.com/cornerstone

Stacking Benjamins
Joe Saul-Sehy’s show, Stacking Benjamins:
stackingbenjamins.com

The MILMO Show
Lacey Langford’s MILMO Show (money planning for military families):
laceylangford.com

Andrea Baumann Lustig
Our interview with estate planning expert Andrea Baumann Lustig, covering the paperwork families facing early onset Alzheimer’s need:
Episode 725

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

• Knowing about money doesn’t make investing easier: Noah worked as a bank teller and interned on a bond trading floor, yet his fear of investing still kept him on the sidelines for a decade. Avoidance is usually emotional, driven by stress and shame, not a knowledge gap.
• Make the first step too small to refuse: Rounding a $12.87 purchase up to $13 and investing the 13 cents is hard to object to. Starting tiny gets people past the fear of investing, and watching the balance grow builds the confidence to add recurring contributions.
• Automation beats willpower for long-term investing: Recurring investments, such as $5 a day or $25 a week, are the most popular feature at Acorns. Automating the habit means it runs in the background for decades, without relying on daily discipline or decision-making.
• Choose patience over prediction with your money: Prediction is thinking you can guess your way to rich quickly. Patience means a diversified portfolio and a 40-year horizon. Noah says it’s fine to play with about 10% of your money, but problems start when people confuse betting with a money strategy.
• The app you use shapes how you behave: The same $10,000 can be handled very differently depending on the platform. Products built around trading reward impulsivity, while Acorns saw low withdrawals and steady investing even during market shocks like Liberation Day in April 2025.
• A company’s business model reveals its real incentives: Acorns charges a subscription instead of profiting from trading, borrowing, or overspending. Noah argues that how a company makes money determines what it rewards, so it’s worth asking how any financial app earns its revenue before trusting it with yours.

Acorns
Noah’s advice is to start small. Open an Acorns account, invest at least $5, and get a $5 bonus investment:
affordanything.com/acorns

Are You a Money Avoider?
Avoiding money cost Noah a decade of investing. Find out if you’re an avoider here:
affordanything.com/fiire

Noah Kerner
Learn more about Noah:
acorns.com/noah

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John asks: I have a question about an executor’s responsibility during probate. My siblings and I are going through the estate process after losing our father. There are no family disputes, but the process will take months. The largest asset is a $500,000 brokerage account that’s mostly in S&P 500 index funds, representing over a third of the estate. For some of us, this money will be life-changing; for all of us, it’s important. I am the executor, and I’m agonizing over the decision of what to do with this account. On the one hand, it feels vulnerable to a major crash. On the other hand, moving it to cash could mean missing out on significant wealth creation during probate. Is liquidating to a money market fund in this moment prudent capital preservation for an executor, or is it improper market timing?

Anonymous (let’s call them “Susan”) asks: When would you choose a bond fund versus holding individual bonds? When I first started investing, I was under the impression that holding a bond fund is just as good as holding individual bonds. So when I built my portfolio, I chose a very low-fee, long-term government bond index fund, and over the last six years, I have watched my bond fund lose 38% of its value. Now is a great time to buy bonds since yields are so high, but it seems to me it is a great time to buy individual bonds. With bond funds, the yields are never locked in, and I could buy more shares while share prices are low. But the premise that a bond fund is good ballast in a portfolio was seriously brought into question during COVID when both stocks and bonds tanked. It’s nice that my bond fund is now getting a higher yield, but frustrating that it is on a smaller current value. The current value of my account is actually pretty close to the original principal from about 10 years ago, and it will take me close to 10 years at a 5% yield to make back the loss of value from the drop in NAV. Is the idea that the NAV will rebound when yields drop? I’ve read that if you’re using bonds as ballast, it is better to hold short-term bond funds because there is much less volatility in the NAV compared to long-term bond funds. Am I correct in thinking bond funds and holding individual bonds function very differently? And when, if ever, does it make more sense to own a bond fund versus individual bonds? I get that you don’t want to time the market with stocks, but since bond yields are locked in, it seems only buying individual bonds when yields are high makes a lot of sense as opposed to a fund where the yields and NAV can be variable. Or do I just need to be more patient with my bond funds? Am I missing something?

Cheryl asks: I love learning about finances, but from 23 years of running our retirement plan at work, I know that most people do not enjoy finances. Over the last 23 years, I’ve watched our 1,100 employees benefit significantly from legal changes that enabled us to default people into a Safe Harbor plan design that is best for the participant. Examples of this in recent years have been auto-enrollment, auto-escalation, and adjusting a default to something like a Vanguard target-date fund, which is our current age-appropriate default.

The vast majority of people do not take action to invest in their 401(k) plan or pay attention to how their investments are set up. Our ability as plan sponsors to set up target-date funds for people is a far better design than the old option of defaulting into a possibly inappropriately conservative fund that they would leave their money in and sub-optimize over the course of their working lives. For many people, company-sponsored 401(k) plans are their only investments, so having a low-fee Vanguard target-date fund as our default is a real benefit.

I think the target-date rant is misplaced for the vast majority of people who really just need auto-enrollment and auto-default mechanisms that are good for them in the long run. I agree with Joe that we can get into the details and become true experts at finances if we care to, but the truth is that the vast majority of people do not care to. I’m saying this based on the 1,100 people in our plan and having been the plan sponsor of a $370 million plan for three decades now. When someone new to the show hears the target-date rant—which I’ve heard on more than one episode—I think when you dig into the nuance, while there are bad target-date funds out there, plan sponsors like us who have done the research have an awesome age-appropriate lineup and achieve great defaulted outcomes. I’m definitely in Paula’s camp on this one and think behavioral economics needs to be taken into consideration in the big scheme of things.

• An inheritance’s time horizon resets at death: As the executor of an estate, you’re managing money for heirs whose time horizon may stretch out for decades. That’s why I argued that keeping a prudent, broad-market index fund invested can make more sense than moving everything to cash.
• Executors are fiduciaries for every beneficiary: Joe’s view: the executor of an estate doesn’t know every heir’s goals, so lock in what the estate is worth today and let each person decide how to invest. Many states’ prudent investor rules may protect you if the holdings are broad index funds (not legal advice).
• A hybrid approach splits the difference: Keep half in the original investments and move half to a money market fund, ideally with every beneficiary’s buy-in. Either way, set aside cash for final taxes, legal fees and debts. None of these choices count as market timing.
• Individual bonds lose value too, just quietly: When rates rise, an individual bond’s resale value drops, just like a bond fund’s NAV. The difference is that no statement rubs it in your face. Hold to maturity and you collect the coupon regardless.
• Check yield to maturity, not the coupon: Joe saw first-time bond buyers pay $1,200 for a $1,000 bond with a 6% coupon and earn far less than they expected. Yield to maturity, plus the issuer’s credit rating, tells you what you’re actually getting.
• Target date funds are a floor, not a ceiling: For people who won’t engage, I’m with Cheryl: a low-fee target date default beats cash. Joe agrees, but his point is that anyone willing to learn can build a simple three-fund portfolio and do better.

Outgrowing Your Target-Date Fund?
Here’s which account each new fund belongs in.
affordanything.com/assetlocation

Free Executor Checklist from Stacking Benjamins
A step-by-step PDF of everything the executor of an estate needs to handle. Tina at Stacking Benjamins made it after handling two estates herself, so if you’re the executor of an estate for the first time, start here.
stackingbenjamins.com/estate

Buy Treasury Bonds Directly from the Government
TreasuryDirect is where I bought 30-year Treasuries to hold to maturity.
treasurydirect.gov

Share Your Worst Investment Mistake
Joe and I want to hear about a bad investment you made and what it taught you. Leave a voicemail and it could be featured on a future episode.
affordanything.com/voicemail

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• Private business owners hold more wealth than billionaires: Roughly 3 million private business owners have a net worth of at least $5 million, averaging about $25 million each. Individually they’re nowhere near Elon Musk, but as a group they hold more than ten times the combined wealth of the Forbes 400.
• The richest Americans often run boring businesses: Beer distributors, car dealers, HVAC companies, mid-market manufacturers, dentists and lawyers fill the ranks of the top 1%. These boring businesses usually have 10 to 50 employees and $10 million to $50 million in revenue, and they drive more than half the rise in top 1% income share.
• The edge comes from years of experience: Most owners spend years learning an industry first. Larry Miller, for example, worked in a Toyota parts department before he bought dealerships. The average founder of a star business is in their late 30s or early 40s, and the typical owner is in their late 50s or early 60s.
• Retiring baby boomers are selling their businesses: A wave of baby boomer owners want to retire, and many of their kids don’t want the business. Buying one of these boring businesses means the idea is already tested, and seller financing can keep the previous owner invested in its success.
• Fund experiments with profits, not debt: Successful owners focus on profitability early and reinvest cash flow instead of borrowing, so no single failed experiment wipes them out. Reinvesting through the business also reduces taxable profits, which makes growth cheaper than pulling money out and investing it elsewhere.
• Concentration builds wealth; diversification protects it: Star business owners stay deeply concentrated in one business for years and carry a lot of idiosyncratic risk. Zidar and Zwick suggest diversifying by moving profits outside the business into retirement accounts, index funds or real estate, and keeping enough of a cushion to cover basic household needs.

Buy a retiring owner’s business or build your own?
Find the ownership path that fits your money and risk.
Find your path

The Everywhere Millionaire
Owen Zidar and Eric Zwick’s book on the private business owners and boring businesses behind most American wealth.
Get the book

The Everywhere Millionaire on Substack
More research and data from Owen and Eric.
Read the Substack

The Millionaire Next Door, by Thomas J. Stanley and William D. Danko
The classic book Paula and the guests compare with the tax-data findings in this episode.
Get the book

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Beth asks: My husband and I are in our late 30s and early 40s. He’s in tech and I’m an accountant. We have two kids—one in preschool and one in elementary school—and our day-to-day support is limited. We’re both working full-time, but we’d love more time to rest, recharge, and spend quality time with our kids while they’re little.

My husband is burned out, and work stress has been affecting his sleep and health. He has a chronic health condition, so health insurance is a huge factor in our plan. My job isn’t super stressful, but I want to keep it low-stress. I don’t want a higher-level role than I have now, and I want more flexibility. In a perfect world, one of us would stay full-time, or close to it, in a low-stress role to carry benefits for the family, and the other would work part-time to manage the home and kids, freeing up more time for both of us.

The challenge is that good part-time options are hard to find in both of our fields. We’re open to retraining, but we don’t know what to retrain into. AI is also on our minds, especially in tech, because it’s changing the work and making us question career security. We also frequently fantasize about completely changing our jobs to do something totally different from our desk-bound office lifestyles.

Here is where we are financially: Our house and cars are paid off, and we don’t plan to take on any debt going forward if we can avoid it. Together, we earn roughly $290,000 a year. We have around $100,000 in a high-yield savings account for emergencies, about $330,000 in taxable brokerage accounts, and a bit over $700,000 in retirement accounts. We save about 40% of our income on average. For the kids, we have modest 529 plans and a separate brokerage account, totaling about $40,000 saved.

We conservatively assume we will need about $100,000 a year to live on once daycare ends, which is in four years when we target our downshift. Coast FIRE appeals to us because stopping work entirely feels scary at our ages, and we want to keep a foot in the working world. The idea is to earn enough to cover our living expenses without drawing down our investments.

Are we at Coast FI now? What about in four years when we plan to downshift? If we are, what should we be thinking about as we pivot, and what careers could realistically provide benefits while allowing part-time work?

Daniel asks: I am a recent retiree from the Phoenix area, and I am now planning college for my sophomore daughter. She is a 4.0 student looking to go to a high-echelon school, maybe an Ivy League institution. I’m trying to get information regarding the college financial aid system, specifically ways to lower my 1099 income for FAFSA, since that interest is what I live off of. I’m also looking to gather information on admissions advisors and SAT tutoring.

Anonymous (let’s call them “Ezra”) asks: I am a younger millennial in my early 30s, and I’ve recently started thinking about my finances a little more seriously in a way I didn’t in my 20s. In the back of my head, I’ve always assumed I would be a homeowner by my mid-to-late 30s, which is when my parents moved into the house where I grew up. But as is the case with so many in my generation, that has started to feel like an impossible dream. Making matters worse is the fact that I live in New York City, and I love it here—it’s the greatest city in the world, and I don’t want to leave.

Do you think homeownership is still a good or even viable financial goal for folks in my generation? Is being a lifelong renter just a financial death sentence that I should avoid, or are there other ways to think of building wealth that might look a little different from how my parents did it, but fundamentally get me to the same place of financial security?

• Coast FIRE means you can stop retirement saving: My definition of coast FIRE: you have enough in retirement accounts that you no longer need to contribute to them. With $1 million invested by their early 40s, Beth and her husband could see that money double roughly every nine years at 8% returns.
• Hitting coast FIRE frees up your savings rate: Once retirement is covered, the gap between income and expenses doesn’t have to go into retirement accounts anymore. That delta can fund short-term reserves, or simply let one of you cut back hours now, while the kids are young.
• The best part-time jobs hide in tiny businesses: Below roughly 25 employees, bureaucracy fades and you get a direct line to the decision-maker. Look for W-2 roles with reduced hours, contract work with a small business, or a handful of contract clients cobbled together.
• For Ivy League aid, the CSS Profile matters most: Lowering your 1099 income won’t move the needle much. The Ivies lean on the CSS Profile, which looks at assets as well as income. Many cover some or all of tuition for families earning under roughly $200,000 to $250,000, if your assets match that income.
• Put SAT and ACT prep ahead of admissions counselors: With rampant grade inflation, standardized test scores are a better signal of preparedness than GPA, which is why testing is back in vogue at top schools. Prep resources are cheap, and a strong score matters more than polished extracurriculars.
• Let the price-to-rent ratio decide rent or buy: Divide a home’s purchase price by its annual rent. Under 15 is a slam-dunk buy; over 25 is a slam-dunk rent; 15 to 25 is a gray zone. In Manhattan, it’s over 25, so I’d rent there and own somewhere it pencils out.

Reached coast FIRE? Map where your next dollar should go
On one free page.
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Joe’s conversation with Lynda Gratton
On taking breaks and changing careers over a longer life (Stacking Benjamins SB1898).
Listen to the episode

Read This Before Planning for College
Stacking Benjamins x The College Investor.
Read the guide

The College Investor
Robert Farrington’s site.
thecollegeinvestor.com

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• 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.

Free Five Pillars Workbook
Jaspreet learned rentals, business, and investing the expensive way. Map your own path and learn how to build wealth across all five pillars, for free.
affordanything.com/fiire

Minority Mindset on YouTube
Jaspreet’s YouTube channel, with more than 2.5 million subscribers.
youtube.com/@MinorityMindset

Briefs Finance and Market Briefs
Jaspreet’s company, with investor research tools and the free Market Briefs newsletter.
briefs.co

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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
Building your own mix instead of a target date fund? See which account each fund belongs in.
Download the guide

Episode #709 with Keith Wargo
Planning for a child with special needs, including special needs trusts and ABLE accounts.
Listen to Episode #709

Episode #755 with Rob Berger
Our interview with Rob Berger, one of the target date fund fans Matt mentions.
Listen to Episode #755

Stacking Benjamins
Joe’s podcast, recorded live on YouTube on Monday afternoons.
Visit Stacking Benjamins

Strategic Coach
The entrepreneur coaching program Joe recommends.
Learn more

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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.

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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.

Free Asset Location Guide
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Jared Dillian’s Website
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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
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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.

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