Afford Anything

#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/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

#624: JL Collins doesn't know what the efficient frontier is. The author of "The Simple Path to Wealth" — the guy synonymous with VTSAX and chill — admits this right off the bat when we challenge him with advanced investing concepts. Collins joins us for Part 1 of a two-part series where we skip the basics and dive straight into the complex stuff. We grill him on whether his simple approach actually beats more sophisticated strategies, and his answer might surprise you. He concedes 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, 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) JL admits he doesn't know the efficient frontier (2:00) Simple vs optimal but complex paths (4:30) Paul Merriman's four-fund portfolio vs VTSAX (6:00) JL concedes Merriman's approach is mathematically superior (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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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/episode619https://affordanything.com/episode619 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 (1:00:14) The Golden Ratio Portfolio (1:12:11) Investment strategies for retirement (1:15:44) Taking money out of your portfolio (1:18:31) Taxes on withdrawals (1:21:14) Where to put your investments (1:23:35) Keeping it simple (1:26:07) How much cash to hold (1:28:20) Market timing risks (1:34:38) Giving back in retirement Learn more about your ad choices. Visit podcastchoices.com/adchoices

#617: Austin and his wife are worried about moving to a single-income household while supporting two kids. Should they free up cash flow by paying off a car loan, or tighten up and stay the course? Paul has been retired for seven years, but still can’t shake his anxiety about not having enough. Is there a good way to know when he’s finally escaped the dreaded sequence of returns risk? Jonathan wants to build up his taxable brokerage account, but he’s having trouble letting go of the tax benefits of a Roth IRA. How does he get past his psychological hurdles? 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#616: Two school teachers in Ohio saved their entire lives for one dream — buying a farm. When they inherited $1.3 million and found the perfect property for $1.2 million, everything seemed perfect. Five days before closing, they received what looked like a legitimate email from their closing company with wire transfer instructions. They sent the money and showed up at closing, only to discover they'd been scammed. The email was fake, sent by hackers who had infiltrated the closing company's servers for months, waiting for exactly this type of high-value cash deal. That story comes from cybersecurity expert Dr. Eric Cole, who joins us to explain why ordinary people have become prime targets for cybercriminals. Cole, a former CIA hacker who served as cybersecurity commissioner under President Barack Obama and advises high-profile clients including Bill Gates' personal estate, has a message: if you think you're too small to be targeted, you're wrong. While billion-dollar companies deploy teams of 60 cybersecurity professionals, you have virtually no protection. Criminals know this. They're not trying to steal $100 million from one person anymore — they're stealing $50 from thousands of people every month. You probably won't notice the small amounts vanishing from your accounts. Cole calls it "death by a thousand cuts," and it's happening right now. We talk through the most common attacks targeting your money. Bank hacking is simpler than most people realize. All criminals need is your account number — printed on every check you write — and your password. With that information, they can often perform electronic fund transfers of up to 50 percent of your account balance without triggering alerts. Cole explains how phishing schemes have evolved beyond simple email scams. Criminals now use artificial intelligence to mimic voices, calling grandparents with their grandchild's actual voice asking for bail money. Ransomware has become a massive business operation. Cole describes a company in Russia with 700 employees whose entire business model is encrypting people's files and demanding payment. Cole advocates for going old-school on major financial transactions. When buying real estate, he meets face-to-face, brings certified checks, and refuses to trust email wire instructions. For daily security, he recommends turning on two-factor authentication for every account, setting up instant notifications for any account activity, and dramatically reducing the number of apps on your devices. We also cover the China-TikTok connection, secure messaging options, and why Cole helped configure President Obama's smartphone to connect to fake cell towers that masked his actual location. Cole's bottom line: cybersecurity isn't just for tech companies anymore. Criminals are targeting ordinary people because we're easier prey than heavily protected corporations. Your money is under threat. Here's how to protect it. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#615: Emily is nervous that buying their first home will derail her family’s journey to financial independence. What’s the smartest way to deploy their savings and stay on track? Based on cap rate calculations, Paul’s real estate investments have appreciated beyond their sensible holding point. Should he sell his assets, or is there more to consider here? Mike is recently retired while his wife still works. With a paid-off home and healthcare already taken care of, what are best practices for drawing down an investment portfolio? 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. For more information, visit the show notes at https://affordanything.com/episode615https://affordanything.com/episode615 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#614: The US just added 139,000 new jobs in May. That beat expectations. But the real story isn't in the job numbers — it’s in the bond market. Something unusual is happening in bonds. Treasury yields are spiking. The dollar is weakening. That combination almost never happens together. And it's signaling concerns about future inflation. Trade wars continue on. A federal court just struck down some tariffs. The administration will appeal. Meanwhile, the EU has until July 9 to cut a deal. If they don't, 50 percent tariffs kick in. As a result, many companies are playing defense instead of growing. The debt situation keeps getting worse. We owe $36.2 trillion. That's more than we owed at the end of World War II as a percentage of our economy. Moody's just downgraded our credit rating. We're not alone — Britain's bonds just hit their highest levels since 1998. The accredited investor rules could finally change. Right now you need an income of $200,000 ($300,000 as a couple) or $1 million in net worth to access private markets. Those numbers haven't changed since they were written in 1982, even though adjusted for inflation, that $200,000 would be $662,000 today. The SEC might start loosening enforcement of the accredited investor rules. That could open up more investments to people who've been locked out for decades. Crypto is finding its footing. The SEC dropped cases against Coinbase. They're backing away from treating most crypto like securities. Bitcoin sits near all-time highs. The US keeps building its strategic Bitcoin reserve. The House just passed what's being called the "One Big Beautiful Bill." It extends 2017 tax cuts. Eliminates taxes on tips and overtime. The Congressional Budget Office says it'll add $2.4 trillion to the deficit over 10 years. That's sparked debate between deficit hawks and growth advocates — including one particularly high-profile debate that has been plastered across the headlines. Consumer sentiment stays stuck at 2022 lows. People expect 6.6 percent inflation. The actual rate is 2.3 percent. That gap between what the data says and what people feel shows up everywhere. We cover all of this in today’s First Friday economic update. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#613: Rachel Rodgers graduated from law school with $330,000 in student loans. Her starting salary? Just $41,000. Most people would have accepted this crushing debt-to-income ratio. They'd slowly chip away at payments for decades. Rodgers had a different plan. She deferred her loans and started her own virtual law practice in 2008 — during the recession, when jobs were scarce and most lawyers were struggling to find work. Her mom thought she was crazy. Her first year, she made around $65,000 in gross revenue with only $300 in overhead costs. By year two, she was earning $300,000. The key to her success wasn't cutting expenses or living on rice and beans. Rodgers focused entirely on earning more money. We talk about the practical steps she took to scale her business. She waited until hitting $250,000 in annual revenue before bringing on her first full-time employee — an administrative assistant who immediately paid for herself by responding to client inquiries faster than Rodgers could manage alone. Rodgers also shares insights from a CEO's perspective on what employees should know when asking for a raise. Understand your company's goals. Know your boss's pain points. When you spot a problem, bring three solutions — not just the issue. She usually goes with whatever option her team recommends. "You are the asset," she explains. This mindset applies whether you're an entrepreneur or an employee trying to maximize your career potential. Our interview covers her transition from solopreneur to multimillion-dollar business owner, her approach to leading employees, and her philosophy on building wealth through entrepreneurship rather than cost-cutting. 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 (2:00) Rachel's $330,000 debt with $41,000 salary (5:35) Why earning more beats cutting expenses (6:40) Starting solo law practice during 2008 recession (9:13) Hitting $300,000 revenue in year two (11:00) Debt payments versus business reinvestment (14:20) Small Business Bodyguard digital product success story (21:00) Virtual law offices and perfect timing decisions (24:30) Taking calculated risks (39:00) Financial independence and Fat FIRE goals (46:00) When to hire employees (53:00) Why opportunity costs matter more than expenses (57:00) Being invaluable employee from boss POV (1:11:00) Salary negotiation tactics (1:19:00) Building relationships with remote team members (1:21:00) Launching adult kids into financial independence Learn more about your ad choices. Visit podcastchoices.com/adchoices

Grant Sabatier never worked in retail, never worked in a bookstore, and had no idea what he was doing when he opened Clintonville Books in Columbus, Ohio. But that's exactly the point. The experiment required 1,200 hours of solo work — measuring spaces, moving 40,000 books, and navigating city regulations. But it taught him something crucial: even experienced entrepreneurs face steep learning curves when they try something new. The serial entrepreneur and author of "Inner Entrepreneur" joins us to share his unconventional journey from online businesses to brick-and-mortar retail. He also explains why he believes everyone will become an entrepreneur within the next decade — whether they want to or not. We dive deep into Sabatier's framework for the four stages of entrepreneurship. The first stage is experimental — you're figuring out how entrepreneurship feels and testing ideas with minimal risk. Most people skip the crucial research phase and invest too much money too quickly. The second stage focuses on building sustainable systems as a solopreneur. Thanks to AI and modern tools, Sabatier launched a new website in 10 minutes recently — something that would have taken two weeks just five years ago. Stage three involves intentional growth. Sabatier warns against the common trap of scaling rapidly without considering how you want entrepreneurship to fit into your life. The final stage is empire entrepreneurship — using cash flow from successful businesses to acquire other companies rather than investing in traditional assets like stocks or real estate. Throughout our conversation, we explore the most common reasons businesses fail, how to avoid fragmented attention, and why Sabatier believes your story is your competitive advantage in an AI-driven world. 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 (01:15) Grant opens bookstore with zero retail experience (03:45) Four stages of entrepreneurship framework (05:20) Creative lease negotiation and getting the space (08:30) Why entrepreneurs invest too much money too early (10:45) Stage two solopreneur and building systems (13:20) Stage three growth and avoiding scaling traps (17:15) Three main reasons businesses die (21:45) Stage four empire building and holding companies (28:30) Four types of holding company structures (32:15) Managing multiple businesses without losing focus (48:20) Why everyone should try entrepreneurship (59:30) Three business types products services productized services (01:04:45) Sell to people with money Learn more about your ad choices. Visit podcastchoices.com/adchoices

#611: With the state of the world changing so rapidly, Lesley is struggling to accept that “this time isn’t different.” Does the past still reliably inform the present in the face of major decisions today? An anonymous caller and her husband want to achieve financial independence through real estate within 10 years. Is it better to pay off existing mortgages or prioritize buying more rentals? Melanie feels duped by the FICO credit scoring system. She’s doing all the right things, but her credit score is still moving in the wrong direction. What’s going on here? 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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In 2005, Sebastien Page nearly died from a mysterious bacterial infection that doctors couldn't diagnose for a week. A single observant physician noticed cuts on his toes from running in wet terrain and connected the dots. The experience forced Page to confront mortality — and completely changed how he thinks about goals. Page, the chief investment officer at T. Rowe Price and author of The Psychology of Leadership, joins us to share why traditional goal-setting might be sabotaging your happiness. He explains how 80 percent of millennials say they just want to get rich, and 50 percent want to become famous. But research from Harvard's 80-year longitudinal study reveals something surprising: people who climbed the social ladder weren't meaningfully happier than those who struggled financially. The real predictor of long-term happiness? The quality of your relationships with others. We explore the dark side of goals through a concept called "goal-induced blindness." Page uses Mount Everest as an example — climbers have a 4 percent chance of dying, the same odds as eating four poisoned gummies out of 100. Yet people still attempt the summit because they become blinded by the goal itself. Page shares his own experience with goal-induced blindness during his demanding career in money management. The relentless travel and pressure contributed to his near-fatal infection in 2005. He learned that working less actually made him more productive. We dive into Page's framework called the "three Cs": core beliefs, curves, and control theory. Core beliefs are the filters through which you interpret the world — like whether you trust people or believe money should be spent versus saved. Curves refer to stress management, based on research showing optimal performance doesn't happen at zero stress. Control theory teaches you when to exercise "strategic patience" versus making quick decisions. Page also introduces the PERMA framework from positive psychology: positive emotions, engagement, relationships, meaning, and accomplishment. He calls the last four "proteins for your soul," while positive emotions are more like a sugar high. The discussion covers practical applications for everything from hiring decisions to relationship choices, using mathematical concepts like net present value to make better life decisions. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Eva is approaching financial independence, but she’s worried about messing up the transition. How does she set her portfolio up for success during the drawdown years of early retirement? Former financial planner Joe Saul-Sehy and I deep-dive into this question in today’s episode. Enjoy! P.S. Got a question? Leave it here. Episodes about the Efficient Frontier: https://affordanything.com/577-qa-the-efficient-frontier-was-perfect-until-hr-got-involved https://affordanything.com/357-practical-investing-and-the-efficient-frontier-with-joe-saul-sehy https://affordanything.com/380-ask-paula-how-to-optimize-your-investments-along-the-efficient-frontier-if-you-dare https://affordanything.com/episode597 https://affordanything.com/episode567 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#608: At age seven, Robert Rosenkrantz made a decision that would shape his entire life: he would take full responsibility for his future.As a child, Rosenkrantz watched his parents struggle financially. His father was unemployed for two years, and his mother worked as a drugstore clerk.Their financial insecurity was painfully obvious to young Robert. He never knew if the electricity or telephone service would be shut off.But rather than seeing this as an obstacle, he saw it as a path to self-reliance.By age 14, Rosenkrantz was managing investments for his family. By 35, he had amassed $400,000 — equivalent to about $4 million today. Then came the pivotal moment that changed everything: a negotiation with wealthy entrepreneur Joe Mailman.When Mailman expressed concerns about traditional investment structures that created a "heads you win, tails I lose" scenario, Rosenkrantz made a bold counter-offer. He put his entire liquid net worth at risk in exchange for a 50/50 profit split with no carried interest."First deal, we lost $100,000. The second one, we made $100 million," Rosenkrantz says during the interview. "So it averaged out."Now 82, Rosenkrantz joins us to discuss his book, "The Stoic Capitalist," and the principles that guided his career.For over 35 years, he's carried the same negotiation card from "Getting to Yes" in his wallet — a reminder that negotiation isn't about winning, but solving problems together.We talk about his counterintuitive investment philosophy: look for companies that require minimal specialized talent, like laundromats or self-storage facilities. He says these often make better investments than those needing exceptional management, like restaurants.This principle guided his first major success, a lawn and garden products business that essentially put dirt in bags — a simple operation that became a regional monopoly and eventually sold for $100 million.Today, Rosenkrantz funds scientific research on longevity and hosts debate programs that present balanced perspectives on contentious issues. His philanthropy includes backing a groundbreaking study that has extended worm lifespans from 15 days to over 250 days — potentially the longest lifespan extension ever achieved in any organism.When asked about retirement, he responds: "How do you spell that?"His advice for decision-making comes straight from stoic philosophy: focus only on what you can control — the present and future, not the past. This means disregarding sunk costs completely when making decisions and using reason to regulate emotions. For Rosenkrantz, counting the zeros — focusing only on opportunities with enough potential impact — helps prioritize time and delegate effectively. At 82, he still practices these principles daily, considering himself "biologically more like 70 and getting younger." Learn more about your ad choices. Visit podcastchoices.com/adchoices

#607: George is a worried baby boomer, wondering if today’s generation is drowning in the noise of today’s financial landscape. How does one find a balance between information and overload? Heather is stunned by the notion that renting could make more financial sense than buying. Where she’s from, the numbers seem to always swing in favor of owning. What’s she missing? Former financial planner Joe Saul-Sehy and I tackle these questions in today’s episode. Enjoy! P.S. Got a question? Leave it at https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices

#606: Hospice nurse and end-of-life educator Suzanne O’Brien joins us to discuss the financial realities of dying in America — and they might surprise you. Remember Aretha Franklin? Her handwritten will was found in her couch cushions after she passed away. Despite her substantial wealth, this simple document was legally upheld. It's a powerful reminder that having any form of will is better than none at all. But there's more to worry about than just having a will or trust. The costs of aging and dying can add up fast. Long-term care costs can quickly deplete even substantial savings. Suzanne shares a story about a couple with over $5 million who were shocked to learn how quickly 24/7 care for dementia would consume their nest egg. Traditional funerals average between $7,000-$11,000, but there are much more affordable alternatives: Home wakes and natural burials can cost just a few hundred dollars Water cremation offers an environmentally friendly option Whole body donation to medical institutions costs nothing while contributing to education Planning ahead gives you control over these decisions and spares your loved ones additional stress. Multi-generational living arrangements can also reduce caregiving costs and address concerns like isolation and safety for aging family members. Suzanne also shares stories about the emotional side of dying. Did you know some people seem to choose when they go? She tells us about a 99-year-old woman in a coma who somehow held on for days until she turned 100, then passed away that very night. Resources Mentioned: Anatomical Board of the State of Florida » College of Medicine » University of Florida US Programs » Anatomical Board of the State of Florida » College of Medicine » University of Florida NATIONAL HOME FUNERAL ALLIANCE - Home Learn more about your ad choices. Visit podcastchoices.com/adchoices