The Stacking Benjamins Show

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 With
Dana'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 happens
Why most people wait until months before retirement to do serious planning -- and the specific things you can only fix if you start far enough out
The JP Morgan research showing 20% volatility in retirement spending year over year -- and why that makes flexibility a more important goal than optimization
Why Dana recommends recalibrating your retirement plan every year rather than building a 30-year model that's guaranteed to be wrong by year five
The 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 behaviorally
The 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 suggests
The 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 five
The 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 covers
The 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 after
Why 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 risk
Why This Matters Now
The 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 Basement
Dana 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 Mentioned
Living 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.com
MarketWatch -- "I'm 66 and have $85,000 in my HSA. When should I start spending it?" by Beth Pinsker
My Mother's Money by Beth Pinsker -- previous Stacking Benjamins appearance linked at stackingbenjamins.com
Stacking Benjamins Basics Guide -- stackingbenjamins.com/basicsguide
Stacking Benjamins YouTube channel -- OG and Anna basics series; youtube.com/stackingbenjamins
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
Stacking Benjamins Community -- stackingbenjamins.com/basement

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SpaceX raised $75 billion in the largest IPO in history -- more than all 71 other IPOs combined so far this year. Shares jumped nearly 20% on day one. Elon Musk became the world's first trillionaire. And if you're a regular investor asking whether you missed out, Joe and OG have a very specific answer: the life-changing money was already gone before the ticker symbol appeared. Here's how IPOs actually work, who really wins, and why your index fund is probably going to own SpaceX anyway.
What You'll Walk Away With
Why the 20% first-day pop was largely an illusion for retail investors -- and what actually happened to the price between $135 and the moment you could buy it
The auction mechanics behind IPO pricing: why institutional investors with early access capture most of the return before the stock hits public markets
Why OG argues that even putting a million dollars into SpaceX at the IPO price and making 20% isn't life-changing -- and why that math actually makes the risk harder to justify, not easier
The sobering stat: 71 other IPOs happened this year before SpaceX, raising a combined $36 billion between them
How SpaceX could still end up in your portfolio without you doing anything -- and which indexes will add it faster than others under new fast-entry provisions
Why S&P 500 investors will have to wait: the three criteria any company must meet before joining, and why SpaceX's profitability timeline makes one of them complicated
The six new space-themed ETFs Wall Street created in the past three months -- and what that pattern always signals
OG on why the person who got rich on SpaceX put money in before you knew it existed, and why you wouldn't have done it either
Why being wrong on a small speculative position might be the most valuable financial education available -- and OG's Thanksgiving pan story
OG and Anna on college planning: how to calculate your actual funding gap, why FAFSA still matters even if you won't qualify for need-based aid, and the high school glide path that protects your savings from market timing risk in the final four years

Why This Matters Now
Every few years a story like SpaceX comes along and makes every investor feel like they missed the trade of a lifetime. The real question isn't whether you missed SpaceX -- it's whether you have a plan that captures the next one automatically, without you having to call your shot.
From the Basement
Joe and OG dig into the SpaceX IPO mechanics, the FOMO math, and why index fund investors may own it soon anyway without lifting a finger. OG and Anna deliver the penultimate episode of their financial basics series with a full college planning walkthrough including the gap calculator, FAFSA, and the glide path strategy for the four years before tuition is due. Doug arrives with Meryl Streep trivia. The show introduces Scout, a new AI assistant built specifically for the Stacking Benjamins guides that only answers from the guides themselves -- and tells you when it doesn't know. Congratulations go out to Stacker Melissa, who finished her last day of work.
Resources Mentioned
Stacking Benjamins Guides -- college planning, tax, and workplace benefits guides with new Scout AI assistant; stackingbenjamins.com/guides
Stacking Benjamins Basics Guide -- stackingbenjamins.com/basicsguide
Stacking Benjamins Scorecard -- stackingbenjamins.com/scorecard
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
The College Investor -- Robert Farrington; collaborator on the college planning guide; thecollegeinvestor.com
Granola AI -- meeting notes tool; granola.ai/sb
Stacking Benjamins Community -- stackingbenjamins.com/basement

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Everyone inherited financial wisdom from somewhere -- a parent who clipped coupons at three different grocery stores, a first job, a financial guru, or just the culture you grew up in. Some of those beliefs serve you. Some of them quietly hold you back. Chris Hill of Money Unplugged joins Joe, Paula Pant, and OG to share the money habits they've had to unlearn -- and then the whole group plays a round of In or Out on some of personal finance's most popular rules.
What You'll Walk Away With
Why Paula's childhood coupon-clipping ritual wasn't really about frugality -- it was about an unstated belief that your time is worth nothing, and how that belief shapes everything
Chris Hill's 20-year belief that dividend-paying stocks are for old people -- and the specific Apple moment in 2012 that finally broke it
OG's admission that despite the math argument, he's never once seen someone actually execute the "invest the difference" 30-year vs. 15-year mortgage strategy in real life
Why "more money will fix this" is the belief most people never fully unlearn -- and OG's honest accounting of what he thought at $17,000, $170,000, and beyond
The In or Out verdict on five popular financial rules: everyone should own a home, pay off debt before investing, never carry a mortgage into retirement, you need a budget to build wealth, and whether financial independence is mostly behavior or math
Paula's anti-budget framework -- why it works when there's a wide enough gap between income and spending, and the one scenario where a real budget actually becomes necessary
Chris Hill on why surrounding yourself with people who aren't impressed by your success might be the most underrated risk management tool in your financial life
The Isaac Newton problem applied to successful people: why brilliance in one area creates a false confidence in all areas -- and why guardrails matter more the more successful you get
Why OG argues that if the leverage-your-mortgage math truly worked reliably, you'd be using the same logic in your Schwab account -- and why almost nobody does
What Melissa from Detroit did this week that every Stacker listening should know about
Why This Matters Now
The most expensive financial decisions are often the ones you've never questioned because someone you trusted taught them to you early. This episode is the permission slip to stress-test those beliefs.
From the Basement
Chris Hill joins Joe, Paula Pant, and OG to dig into the money habits and inherited beliefs they've each had to unlearn -- before the whole group debates whether five of personal finance's most popular rules actually survive contact with real life. Doug arrives with Lou Gehrig trivia and makes everyone do inflation math from 1939. Chris plays for Team Jesse Cramer. The gap between first and second place closes considerably.
Resources Mentioned
Money Unplugged podcast -- Chris Hill; recent episodes featuring Joe Saul-Sehy and Paula Pant; available wherever you listen to podcasts
Afford Anything podcast -- Paula Pant; upcoming episode on how to think through business decisions with a Harvard professor and longtime practitioner
Surfshark VPN -- surfshark.com/stackingb; code stackingbee for four extra months
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
OG financial planning calendar -- stackingbenjamins.com/og
Stacking Benjamins Community -- stackingbenjamins.com/basement

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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 intelligence
Ben'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-old
The wrong lesson an entire generation learned from 2008 -- and why everyone preparing for the last crisis missed the next seventeen years of bull market
Why 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 assume
The behavioral reason complex investment strategies are easy to sell and nearly impossible to hold through a downturn -- while simple strategies survive the pain
Why 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 there
The Beanie Babies divorce court story that perfectly captures what every bubble looks like from the outside
Anna 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 investors
The 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 retirement
Why 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 sold
Animal Spirits podcast -- Ben Carlson and Michael Batnick; available wherever you listen to podcasts
Ritholtz Wealth Management -- referenced for prior guests Barry Ritholtz, Josh Brown, and Nick Maggiulli
Where Are the Customers' Yachts? by Fred Schwed -- referenced for the famous quote on the emotional experience of losing money
Paul Merriman's research on asset allocation -- paulmerriman.com
Stacking Benjamins Vault -- stackingbenjamins.com/vault
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
Stacking Benjamins voicemail line -- stackingbenjamins.com/yelldownstairs
Stacking Benjamins Community -- stackingbenjamins.com/basement

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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 it
The difference between using AI to expand your thinking and using it to execute decisions -- and why only one of those is dangerous
How AI agents eliminate the friction that protects you from your own worst financial impulses -- and why that's exactly how consumer debt gets worse
Joe's four-question framework for knowing when an AI agent is actually helping versus when it's just automating overspending
Why Doug's experience building computer systems made him more skeptical of AI agents, not less -- and what changed
The 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 goes
Why the debt snowball versus avalanche debate has a cleaner answer than most people think -- and when the math genuinely doesn't matter
The 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 arrives
Why 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 looks
Why 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 something
Why 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.com
The College Investor with Robert Farrington -- referenced for prior deep dive on AI financial advice accuracy
Stacking Benjamins Guides -- college planning, tax planning, and HR benefits guides with new AI component; stackingbenjamins.com/guides
Stacking Benjamins Basics Guide -- season one and season two workbooks free at stackingbenjamins.com/basicsguide
Stacking Benjamins Scorecard -- stackingbenjamins.com/scorecard
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
Field Kit Finance -- fieldkitfinance.com
Stacking Benjamins BAD Groups -- stackingbenjamins.com/bad
Stacking 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.