The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
  • 4.4 (2K)
  • Investing
  • Updated Semiweekly

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

  1. 1d ago

    Isaac Newton Lost 80% of His Fortune in a Bubble -- What That Teaches Every Investor (SB1856)

    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! Isaac Newton was one of the smartest humans who ever lived. He also bought into the South Sea Bubble, sold for a profit, watched it keep climbing, bought back in out of pure FOMO, and rode it all the way down to an 80% loss that haunted him until he died. Ben Carlson, co-host of the Animal Spirits podcast and one of the sharpest minds at Ritholtz Wealth Management, joins Joe and Anna to walk through centuries of market history -- bubbles, crashes, and the psychology that makes smart people do dumb things with money. Anna also helps a Stacker named Louie untangle his 401(k) sources and figure out whether it's finally time to bring in a professional. What You'll Walk Away With Why Isaac Newton's South Sea Bubble loss still ranks among history's most instructive investing failures -- and why it had nothing to do with intelligenceBen's framework for why risk means something completely different depending on where you are in your life cycle -- and why a market crash genuinely doesn't matter the same way to a 25-year-old and a 55-year-oldThe wrong lesson an entire generation learned from 2008 -- and why everyone preparing for the last crisis missed the next seventeen years of bull marketWhy Japan's three-decade stock market bubble is the best real-world case for diversification -- and why it doesn't translate as cleanly to the US as people assumeThe behavioral reason complex investment strategies are easy to sell and nearly impossible to hold through a downturn -- while simple strategies survive the painWhy Ben's firm discovered that the hardest financial transition isn't saving for retirement -- it's actually learning to spend the money once you get thereThe Beanie Babies divorce court story that perfectly captures what every bubble looks like from the outsideAnna and OG's take on Louie's four-source 401(k): why it's simpler to manage than it looks, and why "move everything to Roth" is the wrong instinct for most DIY investorsThe Roth conversion icing-on-the-cake strategy: how to use pre-tax and Roth buckets together to manage your tax bracket year by year in retirementWhy one financial pro has a surprisingly negative take on HSAs at death -- and the timing problem that makes spending one down in retirement genuinely tricky Why This Matters Now Every market cycle feels unprecedented while you're living through it. Understanding the actual constant -- human psychology, not headlines -- is the difference between riding out volatility and becoming a cautionary tale, smart as you might be. From the Basement Ben Carlson joins Joe and Anna to walk through centuries of bubbles, crashes, and the psychological wiring that makes both geniuses and ordinary investors do the same dumb things. Doug arrives with Statue of Liberty trivia tied to America's upcoming 250th anniversary. A Stacker calling himself Louie -- and getting Anna instead of OG, much to his surprise -- asks for help simplifying his 401(k) and figuring out his Roth conversion strategy, and gets a reminder that he's already doing better than he thinks. Resources Mentioned Risk and Reward: How to Handle Market Volatility and Build Long-Term Wealth by Ben Carlson -- available wherever books are soldAnimal Spirits podcast -- Ben Carlson and Michael Batnick; available wherever you listen to podcastsRitholtz Wealth Management -- referenced for prior guests Barry Ritholtz, Josh Brown, and Nick MaggiulliWhere Are the Customers' Yachts? by Fred Schwed -- referenced for the famous quote on the emotional experience of losing moneyPaul Merriman's research on asset allocation -- paulmerriman.comStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins voicemail line -- stackingbenjamins.com/yelldownstairsStacking Benjamins Community -- stackingbenjamins.com/basement See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1 hr

  2. 3d ago

    AI Agents Want to Trade Your Stocks and Shop With Your Credit Card -- Here's Why That's a Problem (SB1855)

    Robinhood just launched agentic trading -- an AI that can execute stock trades and purchases on your behalf using criteria you set in advance. There's also a new agentic credit card that can shop for you automatically. Joe and Anna dig into why handing execution over to a machine is fundamentally different from using AI as a thinking partner -- and why the people most excited about AI agents for their money are often the same people who would never trust a human advisor with it. What You'll Walk Away With Why the psychology of trusting AI with money while distrusting human advisors doesn't hold up -- and what's actually driving itThe difference between using AI to expand your thinking and using it to execute decisions -- and why only one of those is dangerousHow AI agents eliminate the friction that protects you from your own worst financial impulses -- and why that's exactly how consumer debt gets worseJoe's four-question framework for knowing when an AI agent is actually helping versus when it's just automating overspendingWhy Doug's experience building computer systems made him more skeptical of AI agents, not less -- and what changedThe debt sequencer framework from OG and Anna: how to rank every debt by interest rate, add an honest emotional layer, and decide where the next dollar actually goesWhy the debt snowball versus avalanche debate has a cleaner answer than most people think -- and when the math genuinely doesn't matterThe one thing that happens to almost every client's bonus money if they don't have a pre-decided allocation plan -- and how to fix it before the money arrivesWhy paying off a 3% mortgage might be the right call even when the spreadsheet says it isn't -- and the taxes-and-insurance math that makes the house payment conversation more complicated than it looksWhy the Stacking Benjamins guides now have an AI component that only draws from the guide itself -- and why it tells you when it doesn't know somethingWhy This Matters Now Every time a company makes it easier to spend or trade without thinking, it's not because they want you to make better decisions. Understanding where AI genuinely helps -- thinking, organizing, comparing -- versus where it hurts -- executing, spending, trading -- is one of the most important financial literacy questions of the next decade. From the Basement Joe and Anna dig into Robinhood's new agentic trading and credit card features and work out where the line between useful and dangerous actually sits. OG and Anna follow with the debt sequencer -- a framework for ranking every debt you have and deciding where the next dollar goes, with room for both math and emotion. Doug arrives with kite-flying trivia that connects to one of the most famous names in American history. Anna is back without OG, which Doug predicts will produce the highest ratings in show history. Resources Mentioned CNBC -- "Your AI agent can now trade for you on Robinhood and buy stuff with your credit card, too"; linked at stackingbenjamins.comThe College Investor with Robert Farrington -- referenced for prior deep dive on AI financial advice accuracyStacking Benjamins Guides -- college planning, tax planning, and HR benefits guides with new AI component; stackingbenjamins.com/guidesStacking 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/201Field Kit Finance -- fieldkitfinance.comStacking Benjamins BAD Groups -- stackingbenjamins.com/badStacking Benjamins Community -- stackingbenjamins.com/basement See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1h 2m

  3. 6d ago

    8 Signs You're Winning With Money SB1854

    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 With Why 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 Now The 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 Basement Joe, 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 Mentioned About 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/bad See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1h 4m

  4. Jun 10

    Helping Mom With Money Before It's Too Late (SB1853)

    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 Episode Why 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 Doug Our Guest Beth Pinsker Beth 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 Show My Mother's Money: A Guide to Financial Caregiving by Beth PinskerLong-term care insuranceFinancial power of attorneyHealthcare proxy documentsTrusted contactsEstate planning basicsNon-conforming mortgagesRay Charles Doug's Trivia Which Ray Charles hit became an official state song? Better Call Saul...Sehy & OG What 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.

    1h 16m

  5. Jun 8

    59% of Retirees Left the Workforce Earlier Than Planned -- Are You Ready If It Happens to You? SB1852

    Most 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 With Why 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 Now You 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 Basement Joe 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 Mentioned Society 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/basement See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1 hr

  6. Jun 5

    Why High Earners Still Feel Broke (And What to Do About It) SB1851

    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'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 With Why 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 Now Housing, 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 Basement Joe, 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 Mentioned Financial 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/basement See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1h 5m

  7. Jun 3

    Retire by 30: Cody Berman on Building Financial Freedom Faster Than You Think (SB1850)

    Cody 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 With Why 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 Now Whether 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 Basement Cody 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 Mentioned Retire 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/basement See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1h 19m

  8. Jun 1

    How to Add 1% to Your Portfolio Without Taking on More Risk (The Systems) SB1849

    Most 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 With Why 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 Now If 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 Basement Joe 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 Mentioned Stacking 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/BAD See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    57 min
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4.4
out of 5
1,950 Ratings

About

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

Information

  • Creator
    Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
  • Years Active
    2013 - 2026
  • Episodes
    1.5K
  • Rating
    Clean
  • Copyright
    © SB Podcast LLC | Gamut Podcast Network
  • Show Website
    The Stacking Benjamins Show

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