Podcast
The Stacking Benjamins Show
Hosted by Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP · EN
Named Best Personal Finance Podcast by Bankrate.com and Kiplinger — and the only podcast the Plutus Awards retired from competition after winning twice — The Stacking Benjamins Show is personal finance that doesn’t put you to sleep.
Hosts Joe Saul-Sehy (former 16-year financial advisor, ex-WXYZ-TV “Money Man”) and Josh “OG” Bannerman, CFP (Certified Financial Planner, Bannerman Wealth) sit around the card table in Joe’s mom’s half-finished basement in Texarkana and talk money with the smartest guests in personal finance, investing, and behavioral economics. As Fast Company wrote, the show “strikes a great balance of fun and functional.”
Every Monday, Wednesday, and Friday: expert guests, real headlines, listener questions, and Doug’s trivia. Topics include investing, retirement planning, budgeting, real estate, behavioral finance, taxes, and financial independence — for anyone who wants to be smarter about money without being talked down to.
Subscribe to The 201 — the free newsletter that goes deeper than the show — at stackingbenjamins.com/201
248episodes
Episodes
Newest firstAll episodes
8 Signs You're Winning With Money SB1854
3d ago01:04:05Summary readyYou 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.
SummaryHelping Mom With Money Before It's Too Late (SB1853)
5d ago01:15:51Summary readyOne 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.
Summary59% of Retirees Left the Workforce Earlier Than Planned -- Are You Ready If It Happens to You? SB1852
1w ago00:59:48Summary readyMost people plan their retirement like they control the date. The data says they don't. A new Society of Actuaries study found that 59% of retirees stopped working earlier than expected -- and for most of them, the decision wasn't theirs. Health setbacks, job loss, caregiving demands, and plain old job dissatisfaction all showed up before the spreadsheet said it was time. Joe and OG dig into what the numbers actually mean, who's most at risk, and the specific steps that create real flexibility before retirement finds you. OG and Anna follow with a full walkthrough of equity compensation -- RSUs, ESPPs, and stock options -- including the tax surprise that catches most people off guard.What You'll Walk Away WithWhy 59% of retirees left the workforce earlier than they planned -- and why only 6% left laterThe income gap nobody talks about: how high earners retire early mostly because they wanted to, while lower earners are pushed out by health and job lossWhy Coast FIRE math falls apart the moment your income stream stops before you planned -- and what that means for how aggressively you should be saving right nowThe one manager change that can end a 20-year career overnight -- and why keeping your network warm is one of the most underrated retirement prep moves availableThe 30-year mortgage paid like a 15-year analogy: why building financial margin now means retirement can happen on your terms, not someone else'sHow to prepare for the emotional side of early retirement -- including the identity shift, the relationship changes, and the pent-up demand that makes the first year unexpectedly wildRSUs versus stock options versus ESPPs: what each one actually means, how they're taxed differently, and why getting a grant without a strategy is the most expensive mistake in equity compThe 5-10% concentration rule: how much of your net worth should be tied to company stock -- and why your paycheck counts in that mathThe RSU tax trap: why your company withholds at 22% but you might actually owe 37% -- and why spending all your RSU money on a pool before April is a terrible ideaStacker Kiki's accountability letter: the complete list of what she's cutting, what she refuses to cut, and why the gamification of frugality is more powerful than white-knuckling itWhy This Matters NowYou may not get to choose your retirement date. But you do get to choose how prepared you are for the day it arrives. The people in this study who retired early by choice had one thing in common: they'd built enough margin that the choice was actually theirs.From the BasementJoe and OG dig into a USA Today piece on the surprising frequency of unplanned early retirement -- and what to do about it before the decision gets made for you. OG and Anna deliver episode five of their financial basics series with a full equity compensation walkthrough, including the tax withholding gap that sends people to April with surprise bills. Doug arrives with Mickey Mantle trivia. A community poll on how often Stackers check their portfolios during headlines produces results that are more honest than most people expected. Stacker Kiki writes a detailed letter about her intentional spending cuts, and OG quietly admits he's been burning through hotel shampoo samples all year.Resources MentionedSociety of Actuaries Retirement Risks Survey -- released May 2026; linked at stackingbenjamins.comUSA Today -- "Most of Us Retire Earlier Than Planned. Here Are the Top Reasons." by Daniel DeVise; linked at stackingbenjamins.comStacking Benjamins Basics Guide -- season one and season two workbooks free at stackingbenjamins.com/basicsguideStacking Benjamins Scorecard -- stackingbenjamins.com/scorecardStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201; Kevin Bailey's hot take on this week's pieceStacking Benjamins YouTube channel -- full OG and Anna equity comp series; youtube.com/stackingbenjaminsStacking Benjamins BAD Groups -- meetups in Boston, Seattle, Twin Cities, Mankato, Tucson, and more; stackingbenjamins.com/badStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking 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.
SummaryWhy High Earners Still Feel Broke (And What to Do About It) SB1851
1w ago01:04:56Summary readyYou're making more money than you ever have. Your net worth on paper looks great. And yet somehow, there's still too much month left at the end of the money. Joe, OG, Paula Pant, and Jesse Cramer dig into why high earners feel financially squeezed -- and why the answer is almost never what you think it is. Spoiler: it's usually not the lattes, it's not too many accounts, and it might not even be a spending problem at all.What You'll Walk Away WithWhy lifestyle inflation doesn't feel like inflation -- it feels like deserved progress, and why that's exactly what makes it so hard to catchThe crucial difference between feeling like you didn't save enough and actually not saving enough -- and why OG's take on this is the most useful thing in the episodePaula's one big fixed cost audit: why making a single large decision beats constantly making small DoorDash decisionsWhy tracking your spending is the calorie counting of personal finance -- only useful short-term, but powerful for getting an honest snapshot before you make any changesThe paper wealth trap: why a high net worth and strong portfolio can coexist with genuinely tight monthly cashflow and why people conflate themJesse's one-line-item challenge: find one thing on last month's credit card statement you wish you hadn't spent, cut it, and see what happens to your motivationWhy OG's advice to "just decide not to feel squeezed anymore" is less dismissive than it sounds -- and the number of times the actual math completely contradicted a client's feelingsThe boats conversation: why a good financial advisor's job isn't to tell you whether to buy the boat but to show you what it costs in terms of your actual goalsWhy comparing your savings rate to the FIRE community can make you feel terrible about saving an objectively impressive amount of moneyThe goal clarity test: if you can't articulate what you're saving toward in specific, time-bound, dollar-denominated terms, the squeezed feeling probably has nothing to do with your budgetWhy This Matters NowHousing, food, and transportation costs are genuinely higher. That part is real. But for a meaningful chunk of the people who feel financially squeezed, the math and the feeling are pointing in different directions. This episode is about figuring out which one you're actually dealing with -- and what to do differently once you know.From the BasementJoe, OG, Paula Pant, and Jesse Cramer work through the Wall Street Journal's reporting on why so many Americans feel financially squeezed even at high income levels -- and whether the problem is real, psychological, or both. OG is recording from a conference adjacent to Disney World and has opinions about wood delivery, boats, and people who feel bad about saving $87,000 a year. Paula gets the giggles. The trivia competition features a man who mowed Steve Wozniak's lawn and had the license plate to prove it. OG wins with suspicious precision. Ronald Wayne, who sold his 10% of Apple for $800 twelve days after founding the company, has a worse story than anyone on this podcast.Resources MentionedFinancial Samurai -- referenced for the lifestyle inflation quote; financialsamurai.comAfford Anything podcast -- Paula Pant; Joe joins most Tuesdays for listener Q&APersonal Finance for Long-Term Investors -- Jesse Cramer; current series: 14 risks in retirement, Charlie Munger inversion framework; two-part series now completeStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201OG financial planning calendar -- stackingbenjamins.com/ogStacking Benjamins Community -- stackingbenjamins.com/basementGo to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
SummaryRetire by 30: Cody Berman on Building Financial Freedom Faster Than You Think (SB1850)
2w ago01:19:13Summary readyCody Berman had the $80,000 corporate job straight out of college, the four-hour daily commute, and the career path everyone said he should want. He hated all of it. By 25, he was financially free -- not because he stumbled into crypto or built a unicorn startup, but because he obsessively maximized the gap between what he made and what he spent, tried 30 different side hustles until a few of them worked, and built a life around what he actually valued. His new book is called Retire by 30. This episode is the conversation behind it.What You'll Walk Away WithWhy the title Retire by 30 is deliberately misleading -- and what Cody says the book is actually aboutThe gap: why the spread between income and expenses matters more than your investment returns, especially at the beginningHow Cody's co-host Justin hit financial freedom at 30 without a single side hustle -- just strategic corporate moves, index funds, and a 75-80% savings rateThe house hacking math: why living in a multi-family property created a $3,000+ monthly swing compared to friends paying Boston rentWhat happened when Cody tried to sell Lauren on FIRE using a spreadsheet -- and the reframe that actually workedWhy the big three (housing, transportation, food) move the needle infinitely more than cutting lattes and canceling NetflixThe 30-side-hustle graveyard: which ones were the worst, which one was the most ridiculous, and the one breakout that still generates income todayPurple's story: how someone retired on $500,000 and now has $1.1 million without adding another dollar to the pileThe surprising thing financial freedom actually teaches you about yourself -- and why it's never a money problem after you hit the numberWhat AI is actually good at for personal finance -- and why the more you already know, the better its answers getWhy This Matters NowWhether you're 25 or 55, the math Cody lays out is the same: find the gap, protect the gap, invest the difference, and build a life you don't need to escape from. The age you start determines the timeline, not the framework. This episode is the one to send to anyone in their 20s who hasn't started -- and anyone in their 40s who thinks it's too late.From the BasementCody Berman joins Joe and OG -- who is recording from inside Hollywood Studios at Coach Con -- to walk through the Retire by 30 framework, the 30 side hustles he actually tried, and the case studies from the book that prove it works in wildly different ways. The USA Today AI financial advice headline gives OG a full platform to explain where AI is genuinely useful, where it confidently hallucinates IRS codes, and why it apparently tried to blackmail a corporate email server. Doug arrives with Trader Joe's trivia after discovering the hard way that cider contains alcohol. Stacker Molly gets her HYSA cleared of all charges.Resources MentionedRetire by 30 by Cody Berman -- retireby30book.com; also available wherever books are soldCody Berman -- Financial Independence Show podcast; co-hosted with JustinA Purple Life blog -- referenced as a case study; apurplelife.netUSA Today -- "Half of Americans get financial advice from AI, but is it any good?" by Daniel DeViseAcquired podcast -- recommended for Trader Joe's, Coca-Cola, and Mars episode deep divesThe College Investor with Robert Farrington -- referenced for prior AI financial advice accuracy testingStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Scorecard -- stackingbenjamins.com/scorecardStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins BAD Groups -- stackingbenjamins.com/badStacking 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.
SummaryHow to Add 1% to Your Portfolio Without Taking on More Risk (The Systems) SB1849
2w ago00:57:03Summary readyMost DIY investors spend their energy optimizing investments. The wealthiest investors optimize systems. According to Vanguard, a great advisor can add roughly 3% to your portfolio -- not by picking better stocks, but by keeping you from wrecking what you already have and by making the boring structural decisions most people skip. Joe and OG walk through the return boosters that actually move the needle, none of which involve a single exotic investment. OG and Anna follow up with the retirement withdrawal sequence that turns a good tax strategy into a great one.What You'll Walk Away WithWhy staying invested is the single highest-return move available to most investors -- and the Wall Street Journal archive experiment that proves it better than any chartHow news addiction creates the three portfolio killers: panic selling, market timing, and the constant feeling that today is the day to make a moveWhy your investment policy statement is a shock absorber between your emotions and your account -- and why advisors often beat DIY investors not by picking better funds but by being harder to reach on bad daysAsset location: the quiet return booster that moves money into the right tax shelter without changing a single investmentWhy tax loss harvesting is widely marketed to the wrong people -- and who actually has a strong use case for itSocial Security timing as a portfolio decision: why "I don't have to decide today" is sometimes the most financially sophisticated answer availableThe sequence of return risk trap that turns retirement into a constant anxiety loop -- and the simple margin of safety that makes it irrelevantThe lightning round: concentrated stock, leverage, crypto yield products, options trading, rebalancing, and tax efficiency -- return or trouble?OG and Anna on the distribution ladder: how to sequence withdrawals from pre-tax, brokerage, and Roth accounts to minimize taxes in retirementWhat IRMAA is, why it shows up two years after the decision that caused it, and why Roth conversions need to happen in November -- not MarchWhy This Matters NowIf you've been dollar-cost averaging into index funds and calling it a day, this episode is the next conversation. The gap between a well-built system and a random pile of investments isn't measured in which funds you chose -- it's measured in taxes paid, sequence of returns survived, and whether you had a plan when everything felt uncertain.From the BasementJoe and OG dig into the return boosters that have nothing to do with picking better investments -- recorded while OG is already inside Hollywood Studios at 4 AM trying to figure out the Lightning Lane math. OG and Anna deliver episode four of their financial basics series with a full walkthrough of tax-efficient withdrawal sequencing, including the IRMAA trap, Roth conversion timing, and why the tax triangle you built in season one is the whole point. Doug arrives with Studebaker trivia. The community delivers an anonymous car buying post that may be the most actionable 200 words the basement has produced all year. And the Stacking Benjamins Inner Circle scam gets called out by name.Resources MentionedStacking Benjamins Scorecard -- stackingbenjamins.com/scorecard; free tool to evaluate your current financial positionStacking Benjamins Basics Guide -- season one and season two workbooks free at stackingbenjamins.com/basicsguideStock Market Maestros episode -- linked at stackingbenjamins.com; on the habits of the world's best investorsStacking Benjamins YouTube channel -- youtube.com/stackingbenjamins; full OG and Anna basics seriesStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins Community (The Basement) -- stackingbenjamins.com/basementStacking Benjamins Meetups (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.
SummaryStop Treating Every Financial Decision Like It's Mount Everest SB1848
2w ago00:57:53Summary readyMost of the financial decisions keeping you up at night are two-way doors. You can change them. You can undo them. The real one-way doors -- the decisions that actually lock you in -- are rarer than you think, and the problem is we're spending the same emotional energy on both. Joe, OG, Paula Pant, and Jesse Cramer take Simone Stolzoff's uncertainty framework from Wednesday and run it straight through real financial life: career changes, portfolio risk, entrepreneurial pivots, and the moment you finally flip the kill switch on something that isn't working.What You'll Walk Away WithThe one-way door versus two-way door framework applied to real decisions -- and why automating your savings contributions is the most underrated version of this ideaJesse's anchor: why life insurance changed everything about how he sleeps at night now that there are passengers in the car with himPaula's anchor: why avoiding debt entirely is the entrepreneurial version of keeping your burn rate survivable when revenue gets unpredictableOG's anchor: long-term belief in human ingenuity as a financial strategy -- and why short-term geopolitical noise is actually an opportunity for investors who aren't panickingWhy selling assets in a taxable brokerage account to cover business payroll is a two-way door -- until enough time passes and it quietly becomes a one-way doorThe kill criteria conversation: how Jesse built an 18-to-24-month runway into his career change before he ever made the leapWhy the Everest turnaround time is the most important financial planning concept most people have never applied to their own goalsOG's client story: when the right risk tolerance isn't the mathematically correct one -- it's the one that lets you sleep at night without calling your advisorPaula on the pivot strategy: keep iterating the broad direction until you find the product-market fit, because the version that works might look nothing like what you started withWhy a career shift becomes more of a one-way door the longer you wait -- and what Rocky Mark's electrical engineer to content creator question reveals about timingWhy This Matters NowThe worst financial decisions happen when people treat reversible choices as permanent ones and freeze -- or treat permanent choices as reversible and act too fast. This episode gives you a framework for telling the difference before the emotion hits, which is the only time it actually helps.From the BasementJoe, OG, Paula Pant, and Jesse Cramer take Simone Stolzoff's Wednesday framework and apply it to the messy real world of careers, portfolios, entrepreneurship, and retirement identity. The trivia competition takes a dramatic turn when OG margin calls Jesse on a Mount Everest question -- and the full margin call rule set gets read aloud for the first time in recorded history after Dottie in Wichita makes a call nobody wanted to receive. Jesse wins the point. OG loses one. The coalition closes the gap.Resources MentionedAfford Anything podcast -- Paula Pant; Joe joins most Tuesdays for listener Q&A; youtube.com/affordanythingPersonal Finance for Long-Term Investors -- Jesse Cramer's podcast; current series: 14 biggest risks in retirement, Charlie Munger-inspired inversion frameworkStacking Benjamins Wednesday episode -- "Why Uncertainty Is an Opportunity" with Simone Stolzoff; stackingbenjamins.comStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking 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.
SummaryWhy Uncertainty Is an Opportunity (and some Wall Street players don't want you to know that) SB1847
3w ago01:01:36Summary readyThe five highest global uncertainty readings since the 1980s have all occurred in the last five years. And yet the answer Wall Street keeps selling -- products that promise upside without downside -- is mathematically impossible and provably underperforms over time. Simone Stolzoff, author of How to Not Know, spent years studying how people, companies, and investors navigate uncertainty well. His findings are the opposite of what the financial industry is selling you right now.What You'll Walk Away WithWhy our tolerance for uncertainty is declining -- and the specific role smartphones and real-time data have played in making investors more anxious and worse at decision-makingThe anchor framework: how certainty in some areas of your life makes it dramatically easier to hold uncertainty in others -- and what that means for how you build a financial planThe Slack origin story -- how a gaming company at the peak of its success chose to shut down and pivot into the unknown, and what that teaches about staying open to what might emergeWhy Warren Buffett and the best venture capitalists actively seek uncertainty -- and how confusion between uncertainty and danger costs most investors real moneyThe kill criteria concept borrowed from mountain climbing -- and how pre-committing to rules before the emotion hits is the only reliable way to prevent catastrophic decisionsOne-way doors versus two-way doors: the Jeff Bezos framework for knowing when to agonize over a decision and when to just actWhy buffer ETFs are mathematically required to underperform broad index funds over time -- and the one question that exposes every "downside protection" pitch instantlyOG's case for looking at your portfolio as rarely as possible -- and the surprising thing that happened when he checked his mortgage balance after months awayWhy building a financial plan around your actual goals makes the daily market headlines genuinely irrelevant -- not as a coping strategy, but as a logical outcomeKathy's story: what a special education teacher who maxed her Roth IRA every year from 1998 to 2024 has in her account todayWhy This Matters NowMarkets will always be uncertain. Headlines will always be alarming. The question isn't how to make that stop -- it's how to build a life and a plan sturdy enough that it doesn't matter. This episode is the clearest case we've made for why your financial plan is more important than your portfolio, and why the two are not the same thing.From the BasementSimone Stolzoff joins Joe and OG to unpack the psychology of uncertainty -- including a couple who took a year apart to figure out if they wanted to stay married, a software engineer who programmed an app to make all his life decisions, and the monk who said not knowing is the most intimate thing of all. The Investment News headline about clients wanting "headline-proof portfolios" gives OG a full platform to explain why buffer ETFs are a product designed for the advisor's book of business, not your retirement. Doug arrives with Wild Bill Hickok trivia. Kathy from the community sends a note that should be required reading for every Gen X stacker who thinks they're behind.Resources MentionedHow to Not Know: The Value of Uncertainty in a World That Demands Answers by Simone Stolzoff -- available wherever books are sold; early readers receive an invitation to an exclusive event with Michael LewisSimone Stolzoff -- simonestolzoff.comInvestment News -- "Advisors say more clients are seeking to headline-proof their portfolios" by Greg Greenberg; linked at stackingbenjamins.comStacking Benjamins Episode 1840 -- "Why 67% of Americans Fear Running Out of Money More Than Dying"; stackingbenjamins.comStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking 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.
SummaryHow Much Should You Really Save Without Hating Your Life? SB1846
3w ago01:06:57Summary readyEveryone wants to know the magic savings number. Is it 10%? 15%? Half your paycheck while eating ketchup packets in the woods?In this Memorial Day basement hangout, Joe, OG, Doug, and Len Penzo cut through the personal finance nonsense and tackle the real question:How much should YOU actually save?Instead of guilt trips and impossible rules, the crew breaks down how real people build wealth while still enjoying life along the way. From automation tricks to lifestyle creep to using raises strategically, this episode is packed with practical ways to grow your savings without becoming financially miserable.Plus:Why most savings advice completely falls apart in real lifeThe easiest way to increase your savings rateHow automation quietly builds wealthWhy your income matters more than coupon clippingThe surprising power of “future you”Estate planning basics you absolutely should not ignoreWhy beneficiary forms matter more than your willDoug learns what “intestate” means… and thankfully it’s less gross than he thoughtWhether you’re just getting started or trying to level up your financial plan, this episode helps you stop chasing perfect numbers and start building momentum.Key TakeawaysWhy there’s no “perfect” savings rateHow to increase savings without wrecking your lifestyleThe psychological mistake that keeps people from savingWhy small automated habits beat big dramatic changesThe best places to find extra money fastHow raises can supercharge wealth buildingThe truth about lifestyle creepEstate planning basics everyone needsWhat happens if your beneficiaries are outdatedWhy trusts aren’t just for wealthy people Resources Mentioned in This EpisodeFeatured Tools, Guides & ResourcesThe Vault Budgeting App Simplify budgeting, subscriptions, spending, and automation. 👉 stackingbenjamins.com/vaultBenjamins After Dark (BAD) Groups Meet other Stackers in your area for accountability, networking, and money conversations. 👉 stackingbenjamins.com/BADStacking Benjamins Basics Guide Free guide covering financial basics, estate planning, tax planning, and more. 👉 stackingbenjamins.com/basicsguideLen Penzo’s Blog & Book Len’s financial writing and his book True Money Stories. 👉 lenpenzo.comRetirement Calculators The crew strongly recommends experimenting with retirement calculators to understand how compound growth changes your future savings needs.AI Tools for Financial Organization OG discusses using AI tools like Perplexity to:Review leasesAnalyze property tax appealsOrganize financial documentsBuild research promptsArticles, Topics & Concepts ReferencedFIRE Movement (Financial Independence Retire Early)Lifestyle CreepAutomation & Auto-Investing401(k) Auto-Increase StrategiesEstate PlanningBeneficiary AuditsTrusts vs. WillsProbate BasicsHealthcare DirectivesDurable Power of AttorneyTax-Smart Retirement WithdrawalsSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
SummaryWhere Are You Drawing the Line? How Smart Spenders Decide What to Cut and What to Keep (SB1845)
3w ago00:55:49Summary readyPrices are up. Budgets are tighter. And people are making some surprising choices about what stays and what goes. The woman skipping the new laptop and the graduation dress is still booked for a Disney cruise, a Bruno Mars concert, and a trip to Lake Erie. It turns out inflation doesn't just squeeze your wallet -- it forces a conversation about what you actually value. Joe, OG, Paula Pant, and Doc G dig into where people are drawing the line, why experiences outlast stuff in the happiness research, and what each of them refuses to give up no matter what.What You'll Walk Away WithWhy people cut the easy stuff first -- and why that strategy relieves anxiety without actually solving the budget problemThe research behind experiences vs. stuff: why the memory of a trip gets rosier over time while objects depreciate in more ways than oneDoc G's spending happiness continuum -- from stuff to experiences to becoming a better version of yourself, and why the last one costs the leastWhy OG's DoorDash experiment was a two out of ten in year-to-date success -- and why four people pulling the rudder in the other direction mattersThe "build from zero" budget reframe that feels more empowering than cutting from the top downOne roundtable member's rule that nothing is ever truly off the table when cash gets tight -- including the house and the private schoolWhat each panelist will never go cheap on -- and one answer involving prescription medications that lands differently than you'd expectThe expenses that are dead to each of them -- and where Joe, OG, Paula, and Doc G land on first class flights and DoorDashWhy the client who cut all Christmas spending had the best holiday season of their lifePapa John's quarterly earnings data that tells you exactly how inflation is changing behavior at the menu levelWhy This Matters NowIf you're in your 40s and you've started quietly trimming things -- streaming services, delivery apps, clothing budgets -- but haven't touched the bigger stuff, this episode names what's actually happening. The question isn't whether to cut. It's whether the things you're cutting are the ones that matter least. That's a values conversation, not a math conversation, and this roundtable is one of the better ones the basement has had.From the BasementJoe, OG, Paula Pant, and Doc G dig into a Wall Street Journal piece on how Americans are changing their spending habits -- and the conversation quickly becomes about what money is actually for. OG reports that his attempt to eliminate DoorDash from the family budget has been going poorly. Doc G went to Bali in coach. The year-long trivia competition takes a dramatic turn as OG's precise mathematical reasoning leads everyone to the wrong answer -- and Doc G wins by going lower. Johnny Carson's guest host strategy turns out to be the missing variable nobody accounted for.Resources MentionedWall Street Journal -- "Where Americans Are Drawing the Line on Price Increases" by Rachel Wolff; linked at stackingbenjamins.comAfford Anything podcast -- Paula Pant; Joe joins most Tuesdays for listener Q&AEarn and Invest podcast -- Doc G (Jordan Grumet); recent episode with Carrie Jorn Grimes on The Joy of MoneyStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking 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.
Summary