The Stacking Benjamins Show

Americans are sitting on more home equity than ever -- and more of them are tapping it. Not because they're struggling, but because they locked in ultra-low mortgage rates and they're not giving those up. So instead of refinancing, they're turning to HELOCs and home equity loans. Joe and OG walk through the math, the psychology, the questions most people never think to ask, and the specific situations where borrowing against your home equity actually makes sense -- and the ones where it quietly destroys a plan that was working.What You'll Walk Away WithWhy home equity borrowing is surging right now -- and why keeping a 3% mortgage while opening a HELOC at 7.5% might still be the smarter moveThe Oreo problem: why having a HELOC open "just in case" is the financial equivalent of leaving a sleeve of Oreos on the counter and expecting not to eat themOG's CEO versus CFO framework: how to separate the decision of whether to do the project from the decision of how to finance itThe rate math you should actually run before choosing between a HELOC, a home equity loan, and a full refinance -- including current Bankrate benchmarksHome improvements, credit card consolidation, college costs, business startup, and investing: OG's honest take on each use case, including the ones that are just bad ideasThe questions nobody asks before getting a HELOC -- including when the rate adjusts (spoiler: faster in one direction), what happens to the draw period, and whether the bank can pull the line at any timeWhy using home equity as a third-tier emergency fund sounds clever but has a fatal flawWhat happens if home prices fall and you've borrowed heavily against the equity -- and why Texas has the 80% ruleOG and Anna wrap up season two of the financial basics series -- including why financial planning is an ongoing activity, not a document, and what's coming in season threeThe one open question OG wants Stackers to send him before season three beginsWhy This Matters NowHome prices are up. Mortgage rates are still elevated. The people most tempted to tap their equity are often the ones who built it most carefully -- and that's exactly when the guardrails matter most.From the BasementJoe and OG dig into the HELOC decision with specifics: math, psychology, use cases, and the questions banks don't volunteer. OG and Anna close out season two of the financial basics series with a reflection on why everything in a financial plan connects to everything else -- and a preview of what's coming in season three. Doug arrives with Bernie Madoff trivia. The guides get a Scout upgrade and the college planning guide gets a refresh just in time for back to school.Resources MentionedStacking Benjamins Guides -- workplace benefits, tax planning, and college planning with Scout AI; stackingbenjamins.com/guidesStacking Benjamins Field Kit -- stackingbenjamins.com/fieldkitStacking Benjamins Basics Guide -- season one and season two; stackingbenjamins.com/basicsguideStacking Benjamins voicemail -- stackingbenjamins.com/yelldownstairs; leave a question for the next Q&A episode with AnnaOG financial planning calendar -- stackingbenjamins.com/ogStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Americans are in the middle of the largest wealth transfer in history. Trillions of dollars are moving between generations right now. But what do you actually do when half a million dollars lands in your account? And on the other side of that question: when it's your turn to give, do you leave it when you die or give it while you're alive? Do you split it equally or based on need? And what about the inheritance that has nothing to do with money at all? Joe asks Paula Pant, OG, and Doc G to answer all of it honestly.What You'll Walk Away WithWhat Paula, OG, and Doc G would each do before noon on the day they found out -- and why OG's first move is to make a list of questions while Paula immediately calls her accountantWhy Doc G, currently in the decumulation phase, would give some away and consider lending money to his son for a property before investing a dollarOG's 40/20/40 framework for any unexpected windfall: 40% to investing, 20% to guilt-free spending, 40% to debt payoff or a medium-term goal -- and why it works for $1,000 checks and $500,000 checks alikeThe grief factor: why Paula says the first thing she thinks of when she hears the word inheritance is grief -- and why emotional cloudiness is the most underestimated risk in how people handle inherited moneyWould you tell anyone? All three guests have different answers -- and the reasons matterGive it while you're alive or leave it when you die: what the King Lear scenario has to do with your estate plan, and why Paula's answer depends entirely on her end-of-life care riskPay for college or leave an inheritance: Doc G picks college, OG picks experiences, and the reasoning behind each choice reveals two completely different theories of compoundingEqual inheritance versus needs-based inheritance: why Doc G has already had the conversation with his kids and why he's not apologizing for unequal parentingWhat people at the end of life actually want to leave behind -- Doc G's hospice experience in one of the most memorable moments of the episodeThe non-financial legacy each panelist is trying to leave -- and Doug's surprisingly moving answer about where joy actually comes fromWhy This Matters NowThe wealth transfer is already happening. Whether you're on the giving end or the receiving end, the decisions made in the first days after money changes hands tend to be the ones people regret most. This episode is the conversation to have beforehand.From the BasementPaula Pant, OG, and Doc G work through the full inheritance question -- tactics, emotions, purpose, and legacy -- in one of the more wide-ranging Friday conversations this show has produced. Paula tries to win the trivia competition for the first time in longer than anyone cares to admit, immediately hoping she gets to thank the Academy. Doug closes with something nobody saw coming.Resources MentionedEarn and Invest podcast -- Doc G (Jordan Grumet); upcoming episode with Dr. Jaspal Singh on the case for ambitious careers; wherever you listen to podcastsAfford Anything podcast -- Paula Pant; recent episode with Dr. Julia Garcia on five habits of hope; wherever you listen to podcastsStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201OG financial planning calendar -- stackingbenjamins.com/ogStacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Most retirement planning focuses on accumulation -- how to save enough. Dana Anspach of Sensible Money has spent her career on the other side of that equation: what happens when it's time to actually spend the money. In her new book Living Off Your Acorns, she breaks retirement into four distinct phases -- pre-go, go-go, slow-go, and no-go -- and argues that the decade before you retire may be the most important planning window of all. CFP and MarketWatch columnist Beth Pinsker also stops by to flag an HSA inheritance problem that almost nobody sees coming.What You'll Walk Away WithDana's four-phase retirement framework -- pre-go, go-go, slow-go, and no-go -- and why the pre-go years (the 10 years before you stop working) are where the most valuable planning actually happensWhy most people wait until months before retirement to do serious planning -- and the specific things you can only fix if you start far enough outThe JP Morgan research showing 20% volatility in retirement spending year over year -- and why that makes flexibility a more important goal than optimizationWhy Dana recommends recalibrating your retirement plan every year rather than building a 30-year model that's guaranteed to be wrong by year fiveThe income ladder approach: how having bonds and CDs maturing each year means you never have to sell investments at a loss to cover spending -- and why it also helps behaviorallyThe fundedness concept: why the safe withdrawal rate was calculated assuming the Great Depression starts the day you retire, and why dynamic go-go spending gives you more room than the 4% rule suggestsThe retirement red zone -- the five years before and the first year after leaving work -- and why Dana starts shifting portfolios toward conservatism 10 years out, not fiveThe long-term care reality check: why only about 15% of people incur a catastrophic care cost, why home equity is Dana's preferred reserve asset, and what insurance actually covers versus what people hope it coversThe HSA tax problem Beth Pinsker uncovered: why a non-spouse beneficiary who inherits your HSA takes the entire balance as ordinary income in a single year -- and why you should spend it before your Roth, not afterWhy power of attorney paperwork at each individual financial institution matters more than most people realize -- and the specific authentication vulnerabilities that put retirees at fraud riskWhy This Matters NowThe decumulation phase requires a completely different strategy than accumulation -- and most people don't start thinking about it until they're months away from leaving work. Dana's case is simple: the earlier you start building flexibility into every decision, the more options you have when life doesn't go according to plan. And it almost never does.From the BasementDana Anspach joins Joe and OG for a deep dive into Living Off Your Acorns, covering everything from her grandpa feeding squirrels in retirement to the very specific paperwork every financial institution needs before they'll honor your power of attorney. Beth Pinsker makes a headline segment appearance to explain the HSA inheritance tax problem her MarketWatch piece uncovered. Doug arrives with World Cup trivia. The community shares reactions to the 59% unplanned retirement episode, including Shep's 30-year story of gradually bumping his savings rate and a 37-year-old Stacker leaving the workforce in two weeks for baby number four.Resources MentionedLiving Off Your Acorns: Your Guide to the Four Phases of Retirement by Dana Anspach -- available on Amazon; search "Living Off Your Acorns" or "Dana Anspach"Sensible Money -- Dana Anspach's financial planning firm; sensiblemoney.comMarketWatch -- "I'm 66 and have $85,000 in my HSA. When should I start spending it?" by Beth PinskerMy Mother's Money by Beth Pinsker -- previous Stacking Benjamins appearance linked at stackingbenjamins.comStacking Benjamins Basics Guide -- stackingbenjamins.com/basicsguideStacking Benjamins YouTube channel -- OG and Anna basics series; youtube.com/stackingbenjaminsStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Thanks to Surfshark for sponsoring the show. Go to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN!You might not look rich on Instagram. That doesn't mean you're behind. Joe, Paula Pant, Jesse Cramer, and Anthony Weaver from About That Wallet work through eight real signs that your financial life is on track -- covering stability, behavior, and mindset -- and spend just as much time on why we're all so bad at recognizing the wins we've already had.What You'll Walk Away WithWhy a $1,000 emergency fund puts you in the top 40% of Americans -- and what Jesse's registered nurse versus Uzbek architecture professor framework tells you about how big yours actually needs to beThe debt-to-income ratio question nobody asks: would you rather have a 10% DTI and zero savings, or $1 million invested and a 45% DTI? Paula and Anthony work out their actual answers liveWhy someone making $250,000 and living paycheck to paycheck is less financially trustworthy than someone making $60,000 with a two-month buffer -- and what that reveals about the real gameAnthony's dream walk framework: the questions he asks clients to make sure their day-to-day financial habits are actually pointed toward what they say they wantWhy the trend matters more than the number -- and the one thing Jesse tracks monthly that most people miss when they're focused only on net worthThe peace of mind problem Paula names that most personal finance conversations skip entirely: there is very little correlation between the numbers in your accounts and your actual anxiety levelWhy Jesse thinks prioritizing stress reduction over optimization might actually produce better long-term outcomes than squeezing every percentage pointThe Instagram tell that almost none of the visible wealth you're comparing yourself to is real -- and the Tai Lopez rental strategy that proves itAnthony's story about the client who needed permission to sell investments to feed her kids -- and why money as a tool looks completely different at every income levelWhy money is the easiest possible scorecard -- and how that ease is exactly what makes it so dangerous as a proxy for self-worthWhy This Matters NowThe comparison pressure has never been higher and the metrics have never been more visible. This episode is a reminder that the signs of real financial health are mostly invisible on the internet -- and that you might already be further along than you think.From the BasementJoe, Paula Pant, Jesse Cramer, and Anthony Weaver from About That Wallet work through eight signs of financial progress from a wisdom.com piece while talking about drone footage FOMO, Tai Lopez's rental Lamborghinis, and why somebody in Florida held a half-eaten grilled cheese sandwich for ten years before selling it on eBay.Resources MentionedAbout That Wallet podcast -- Anthony Weaver; available wherever you listen to podcastsAfford Anything podcast -- Paula Pant; recent episode with Dr. John La Puma on why going outside improves health and productivityPersonal Finance for Long-Term Investors (FILTI) -- Jesse Cramer; recent AMA episode on retirement planning questionsFreedom app -- referenced by Paula for blocking Instagram; freedom.toSurfshark VPN -- surfshark.com/stackingbee; code stackingbee for four extra monthsStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins Community -- stackingbenjamins.com/basementStacking Benjamins BAD Groups -- stackingbenjamins.com/badSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

One day you're comparing Roth IRA options. The next you're helping Mom navigate long-term care paperwork, fighting with a bank over a power of attorney document, and wondering how anyone manages all this without losing their sanity.Welcome to the world of financial caregiving.Today, certified financial planner and financial journalist Beth Pinsker joins us to share the lessons she learned while helping manage her mother's finances during a health crisis. From powers of attorney that don't always work when you need them to the surprising warning signs that an aging parent may need help, Beth offers practical advice every family should hear before an emergency arrives.Then in our headline segment, a blast from the financial past: unconventional mortgages are making a comeback. Are these products helping qualified borrowers who don't fit the traditional mold—or are we seeing early warning signs of the next lending problem?Plus, Doug celebrates the legacy of Ray Charles with today's trivia challenge.In Today's EpisodeWhy financial caregiving is far more complicated than most families expectThe paperwork Beth wishes she'd completed before her mother's medical emergencyHow power of attorney works—and why it may not work as smoothly as you thinkWarning signs that a parent may be struggling financially or cognitivelyThe surprising problems created by passwords, two-factor authentication, and modern banking systemsWhy trusted contacts, healthcare proxies, and emergency document folders matterCommon family conflicts that emerge during caregiving and estate settlementWhether today's unconventional mortgages should worry homebuyersThe important differences between today's lending environment and 2008Ray Charles trivia from DougOur GuestBeth PinskerBeth Pinsker is an award-winning financial journalist, Certified Financial Planner™, and author of My Mother's Money: A Guide to Financial Caregiving. Through both her professional expertise and personal experience, Beth helps families prepare for the financial realities of caring for aging loved ones.Mentioned In Today's ShowMy Mother's Money: A Guide to Financial Caregiving by Beth PinskerLong-term care insuranceFinancial power of attorneyHealthcare proxy documentsTrusted contactsEstate planning basicsNon-conforming mortgagesRay CharlesDoug's TriviaWhich Ray Charles hit became an official state song?Better Call Saul...Sehy & OGWhat financial caregiving preparations have you already completed—and which ones are still sitting on your to-do list?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Thirty years ago Beth Kobliner wrote the book that a generation of financial planners handed to their clients' kids. The core advice still holds. But the world around it has changed dramatically -- frictionless spending, gambling apps disguised as investment platforms, and a housing market where the average first-time buyer is now 40. Beth comes back to the basement with an updated edition of Get a Financial Life and a clear-eyed take on what's harder now, what's easier, and what was always just common sense.What You'll Walk Away WithWhy the shift to invisible, frictionless money has made spending harder to track -- and the two-week experiment that fixes it without turning into a second jobThe yours, mine, and ours account system for couples where one person saves and one person spends -- and why autonomy is the key to avoiding money resentmentWhy putting a price tag on your goals changes your spending behavior more than any budget ever willThe biggest mistake first-time home buyers make right now -- and the math on why a 10% down payment often beats waiting for 20%Used versus new car: the $20,000 gap that makes the decision simple -- and the negotiation script that puts you in control at the dealershipStudent loan reality check for 2026 -- what's changing by July, where to run the numbers, and who qualifies for public service loan forgiveness now that it's actually workingWhy paying off a 22% credit card is mathematically equivalent to earning 22% guaranteed -- and what that means for how you prioritize your moneyThe gambling platform statistic that should alarm every parent of a 20-something: 25% of Gen Z and millennials consider online gambling an investmentThe annuity conversation most advisors won't have honestly -- what they're actually selling, what the fees really cover, and the two use cases where they might actually make senseWhy an annuity inside an IRA is, in OG's words, an abomination -- and the three questions to ask before signing anythingWhy This Matters NowWhether you're in your 40s and wishing you'd read this at 22, or you're handing it to someone who just graduated, the fundamentals Beth laid out three decades ago are still the fastest path to financial stability. What's changed is the noise around them -- and the sophistication of the products and platforms designed to get in the way.From the BasementBeth Kobliner joins Joe and OG to walk through the 30th anniversary edition of Get a Financial Life -- covering homes, cars, student loans, debt, and the new financial traps that didn't exist in 1996. The headline segment digs into a CNBC piece on why retirees are thinking about annuities wrong, which turns into one of the more honest annuity conversations the basement has had. Doug arrives with Spice Girls trivia that everyone over 35 finds embarrassingly easy. The meatloaf debate breaks out at the end and resolves nothing.Resources MentionedGet a Financial Life by Beth Kobliner -- 30th anniversary edition available wherever books are soldBeth Kobliner -- bethkobliner.comstudentaid.gov -- loan simulator and repayment plan optionsEdmunds and Kelley Blue Book -- invoice price research before car negotiations; edmunds.com, kbb.comCARFAX -- used car history reports; carfax.comCarvana, Autotrader, CarGurus -- used car shopping platformsCNBC annuities article by Greg Iacurci -- linked at stackingbenjamins.comJP Morgan Guide to the Markets -- referenced in discussion; search "JP Morgan Guide to the Markets"Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Meetups -- stackingbenjamins.com/meetupStacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What if the reason your investment decisions feel so hard isn't the market -- it's how you're wired to think about outcomes? Annie Duke spent years as a professional poker player winning over $4 million in tournaments, then devoted the next chapter of her career to understanding why smart people consistently make bad decisions. The answer has nothing to do with intelligence and everything to do with how we confuse results with quality. She brings the full framework down to the basement today.What You'll Walk Away WithWhy certainty is the enemy of good decision making -- and the mindset shift that makes uncertainty feel like an advantage instead of a threatThe Pete Carroll problem: how tying the outcome of a decision to the quality of the decision is quietly wrecking how you evaluate your investmentsWhy being smarter actually makes this bias worse -- and how intelligent people spin data to confirm what they already believe more effectively than anyone elseThe difference between wanting to be right and wanting to be accurate -- and why that single distinction changes everything about how you process new informationHow to hold your beliefs as "works in progress" rather than positions to defend -- and why that opens you up to information that actually improves your decisionsWhy the stock market's short-term volatility is almost never the signal investors treat it as -- and what a 40-year Berkshire Hathaway chart actually tells youThe poker table parallel to long-term investing -- and why you can make all the right moves and still lose, which means a bad outcome never proves a bad decisionWhat the Philly Special play reveals about how we reward boldness only when it works -- and what that tells you about how you judge your own financial choicesA listener question on market-cap weighted index funds -- why the s and p is built the way it is and what you'd actually need to do to weight it differentlyThe best personal finance and business books the crew is reading right now -- including picks from OG that go well beyond the usual recommendationsWhy This Matters NowFor Stackers in their 40s watching a volatile market and second-guessing decisions that were perfectly sound six months ago, this episode is a direct intervention. The temptation to call a good decision bad because the market moved against you -- or to abandon a long-term strategy because of a short-term result -- is exactly the bias Annie Duke has spent her career studying. The framework she brings today doesn't just apply to poker. It applies to every financial decision you'll make for the rest of your life.From the BasementAnnie Duke joins Joe and OG to walk through the decision-making framework behind her book Thinking in Bets -- including the Super Bowl story that reframes how most people evaluate every financial move they've ever made. The headline segment tackles parents spending six figures on kids' extracurriculars and what the trade-off actually looks like for retirement savings. Doug arrives with poker-themed trivia about the all-time tournament earnings leader, gets it mostly right, and declares victory anyway. Whether the basement poker tournament ended in anyone's favor is a matter of some dispute.Resources MentionedThinking in Bets by Annie Duke -- available wherever books are soldAnnie Duke's website and weekly newsletter -- annieduke.comAnnie Duke on Twitter -- @AnniedDukeThe Truth About Money by Ric Edelman -- recommended by JoeSet for Life by Scott Trench -- recommended by JoeBroke Millennial by Erin Lowry -- recommended by JoeHow to Be a Financial Grownup by Bobbi Rebell -- recommended by JoeThe Behavior Gap and The One-Page Financial Plan by Carl Richards -- recommended by OGFooling Some of the People All of the Time by David Einhorn -- recommended by OGBuilt to Sell by John Warrillow -- recommended by OGThe E-Myth by Michael Gerber -- recommended by JoeThe Goal by Eliyahu Goldratt -- recommended by JoeStacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ever wish you had a second chance with your money? Billy B. hoped he'd get one. After being convicted and sent to prison after the death of his friend, Billy went through some serious soul searching, and the end result of that is on display on today's show. Not taking any opportunity for granted, working hard to find solid financial (and life) footing, and the value of surrounding yourself with good friends and mentors are just three of many themes we'll talk about in this fantastic discussion with Billy (who now also blogs at WealthWellDone.com). We originally aired this show in 2018, but the lessons Billy learned are truly timeless. Read the rest of the original show notes below:In our headlines segment, a new software program means that some of your advisors may be expendable….or maybe not. We’ll discuss the hot topic of humans versus AI on today’s show. Plus, Warren Buffet just wrote his annual letter to investors. What are some of the takeaways? One publication listed their favorites and we’ll review and discuss them. As always, Mr. Buffet doesn’t fail to use the English language as a weapon while talking about investing, value, and evaluating risk.We’ll of course have more from the world of financial planning, throw out the Haven Life line to lucky listener Luke, who wonders about investing to beat inflation without taking too much risk. For a five year goal, what investment works best? Are stocks too risky? Should he use junk bonds? We’ll shine a light on that topic (and maybe one we can’t talk about here), as well. We also answer a letter from Jon, who asks about asset allocation. What is a great way to manage your money and diversify correctly? You’ll have to listen to find out!Of course, we’ll still score with some of Doug’s delightful trivia, and more. Learn more about your ad choices. Visit podcastchoices.com/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.